What sissy outfit do you want the most?

    So i LOVE questions like this because they get my pathetic wittle sissy brain going AND i get to go shopping!

    So I feel like there’s a few stereotypical outfits every sissy gurl should have:

    The Sissy Maid


    This one’s cute, but the neckline is a bit too high and conservative for me. I do like the mixture of frills and satin though!


    This one is more my style, a bit sluttier, but still has the satin and frills.

    The Sissy Schoolgirl


    I really like this one, it’s SUPER slutty and plays the stereotype well, and that ‘fuck me’ skirt just screams “Bend me over and take me anywhere, sir!”

    The Sissy Cheerleader


    This one is nice, but obviously is in the wrong color....

    The Sissy Baby


    Isn’t this one adorable?? It’s like someone said “I want to make a dress that looks like diapers, for someone that WEARS diapers!”

    So what do we do? Which one to pick?

    I feel like I want one that encompasses all the stereotypes, is cute, and slutty all at the same time.


    That’s why i picked this cute one! It has a little bit of everything!


    But then I came across this one! And I love the idea of someone bending me over, hiking up my skirt, and unbuttoning my onesie to fuck/spank/use me. So this one, this is the winner!

    Thank you so much for the ask and giving me something to occupy my last 3 hours! :)

    The Boss’ Baby - Part 14 “Desperation”

    Part 1 here


    Jesus, how many times did they do it last night?!

    I contemplated sorrowfully as i squeezed the contents of the 4th used condom into the tiny bowl.

    It had been a week since the dinner that officially turned my life upside down. Where I was forced to watch as my Boss pounded my wife into oblivion. He had been staying over—and sleeping in my marital bed—ever since.

    I discarded the remnants of the 4th condom and added it to the pile on the tray of the new high chair i was sitting in. Apparently, in addition to being muscular, athletic, and Boss of a successful company, Charles was also a carpenter on the side. He took the liberty of building a large, oversized high chair for me to eat all of my ‘meals’ at home in. Anything to further emasculate me in my wife Amy’s eyes. Apparently it was working too, because Amy deemed it necessary that the highchair be painted a bright pink and stamped with flowers.

    My meals consisted of mostly pureed foods. I had forgotten what it was like to chew. But my morning breakfast always consisted of the previous night’s ‘leftovers’ from Charles’ escapades with my wife.

    “Is your breakfast ready sweetheart?” Amy asked cheerfully as she sipped her morning coffee in nothing but a bath robe. She didn’t even bother tying it closed, knowing the hint of her nakedness only helped to drive me crazy inside my chastity cage.

    “Yes Mommy...” i said dejectedly. She had insisted on me calling her that permanently. Calling her ‘honey’ or even ‘Amy’ was strictly forbidden now.

    “Oh! Almost forgot!” She said, reaching between her legs and pulling another used condom from her vagina. “I was keeping this one warm for you!!” She beamed, placing it on the tray.

    Charles chuckled behind the newspaper at the table in front of me. Not even sparing me a glance as he flipped the page.

    I whimpered as i picked up the 5th rubber sack of jizz, noticing it was knotted. I looked up at Amy, smiling at me expectantly. I knew I had to get the splooge in the bowl, and the only way for me to open the condom was to break it open with my teeth.

    I could taste her juices as I bit at the bulbous tip. After a few unsuccessful chews, the reservoir finally popped open. Squirting some of the penis juice out the side of my mouth and down my chin before i could aim it into the almost full bowl.

    “Oops! Wooks wike the wittle baby needs her bib!” Amy exclaimed in her patronizing Mommy voice.

    She reached behind the high chair and pulled out a large, pink bib that read “Little Princess” in big, feminine writing. After she clasped it around my neck she used it to dab the sticky jizz dribbling down my chin and redirect it back to my mouth.

    Amy had always despised cum. Never letting me finish in her mouth back when she was giving me blowjobs, even stopping as soon as there was the first hint of pre-cum. So i knew how disgusted she was to handle all of this thick, sticky Charles-spunk. But she had no problem with grabbing a tiny baby spoon, and scooping a gooey helping to feed to me.

    “Open up baby!!” She cooed, “here cummmsss the airpwane!!!”

    After shovelling every last spoonful of disgusting, salty baby-batter into my mouth, and making sure to catch and refeed every last drop that seeped out the sides, she plopped the spoon down into the empty bowl and reached under the tray between my legs. Pinching my diapered crotch.

    “Awww! Someone is SUPER soggy this morning!” She giggled. Poking my saturated pink princess pampers.

    “Why don’t you go get your morning spankies from Daddy, then come upstairs and Mommy will change your diaper and get you ready for work!” She smiled. Pinching me playfully on the cheek like I were an infant. Unlocking the tray, and helping me off the chair as if i needed it.

    It was hard to decide what had become my least favorite part of my day since my new routine started, but this was definitely up there. Getting down on my hands and knees, and crawling over to the man now fucking my wife, sitting up so that my saggy diaper drooped to the floor and having to say: “Daddy, can i please have my spankies now?” In a pathetic, high-pitched, sissy baby voice.

    Charles glanced up from his paper as if noticing me for the first time. He sighed, chuckled, sipped his coffee, then pushed his chair back, already unbuckling his belt.

    “You know what to do.” He said firmly as he stood up and pulled his belt through his loops.

    I whimpered softly as i bent over the dining table. The same way i did one week ago when Charles pelted me right in front of my wife. Apparently she had enjoyed it so much she decided to make it a daily thing. She carefully pulled my floppy, drenched diaper down around my calves. I stayed stock still. Last time i flinched too hard and broke the tapes i got extra swats for it.

    I could hear the wind whistle as Charles reared back and snapped the belt across my bare cheeks with a THWACK!

    I bit down on my thumb to keep from squealing as the assault began. Amy stayed and watched lash after lash until i was in tears. She rubbed my head softly as if i were nothing more than a disobedient pet receiving its punishment, then gave Charles a long, passionate kiss before heading upstairs. Knowing she’d still be able to hear my squeals from the bedroom.

    After my ass and thighs were painted red, Charles tossed the belt on the table and sat down to catch his breath. My only mercy being that he didn’t want to get all sweaty in his suit before work. I sniffled and dabbed my damp eyes, knowing it was appropriate for me to stand up and carefully pull my cold, wet diaper over my flaming hot asscheeks.

    “Before you go...” Charles said as i made to head upstairs, “why don’t you take care of something for me.” He reached under the table and unzipped his zipper.

    Really? I wanted to say. Now? Have you not cum enough in the past 12 hours?!

    But it wasn’t about cumming for him. People in power are in power because they crave it so. They relish any opportunity they can to establish dominance over those they’re superior to. That’s what they get off on.

    I thought of how much my life would be different if I was one of those types. An alpha, a power-hungry, dominant, aggressive man that took what he wanted. But instead, i had to take his dick in my mouth, under the table, while he read the paper and finished his breakfast.

    “You know...” he said nonchalantly, “your wife sucks better dick than you.”


    It had been almost a whole month since i’d cum. I was becoming desparate.

    Almost all of my daily thoughts centered around something sexual and perverted. And, to my chagrin, my brain often defaulted to the sexual encounters of my wife and Charles.

    She had come up to the office almost every day before lunch. Spending an hour or so inside, behind locked doors, while i was forced to wait at my cubicle and imagine what they were doing. At lunch time, Amy would come out, hair disheveled, face flushed, carrying tupperware of whatever pureed slop she had for me that day, then hand me a used condom to frost my lunch with. After spoonfeeding the cummy mush to me, she’d pinch me on the cheek, check my diaper (but never change it) and then head back home.

    Because Charles was getting sex regularly, he rarely needed me to please him anymore. Which meant he hadn’t fucked my ass in over a week. I hated how much i was starting to miss it. To crave it. Anything to help release the building pressure in my balls and prostate as i leaked from a good pounding.

    I had tried using my fingers. Lubing them up with my saliva and sneaking them into my diaper at my desk or at home in the closet during times i was supposed to be cleaning in my french maid outfit. All it did was make me even hornier.

    I remembered seeing in my sissy porn (the same one that landed me in this situation in the first place) that certain girls could achieve what was called a “sissygasm”. Which was where they were able to cum from only anal stimulation of their prostate. I decided to try it using a cucumber. I would have used the big black dildo Amy had bought when she was fantasizing about Charles, but it was tucked away in their room. My room. Or what used to be ours.

    I used a little Crisco as lube and hid away in the closet to pound myself with the cucumber. After 20 minutes of shoving it in and out of my hole, i was unsuccessful at achieving anything but a small bit of leakage. When i came out of the closet, Amy and Charles were waiting for me. Arms crossed. Charles proceeded to blister my ass while Amy shoved the cucumber in my mouth and forced me to eat the entire thing.

    I decided my only hope was to find someone around the office to bang me. It made me feel like such a thirsty slut to be hunting for dick to fuck me in my ass.

    Obviously if Charles wouldn’t fuck me, my next hope would have to be Dave from IT.


    I made my way down the hall to his office. It was tucked away in a pretty private corner of the floor. So it was unlikely anyone would hear us moaning.

    I knocked on the door. I could hear a rustling and scampering. “Just a minute!” Came his voice.

    The blinds of his window creaked open. When he realized it was me, he heaved a sigh.

    The door opened. I walked in, but he didn’t even say ‘hi’ or even acknowledge me. Just hurried back to his desk and back in his chair. The screen of his computer illuminating a big, white, rubber dildo sticking straight up off his desk.

    “Sorry about that, sir!” He said in a high-pitched voice. But he wasn’t talking to me. He was talking to his screen.

    “That’s ok, slut!” Came a gruff voice from the monitor. “Now get that dick back in your mouth!”

    “Yes sir!!” Dave said. And started jamming the head of the 8 inch rubber cock into his mouth.

    “There’s a good, slut!!” Said the voice, “suck it good! Daddy’s gonna cum soon!”

    I moved to the side of Dave’s desk and saw a window on the screen with some big, fat, naked white guy stroking his cock. It took me a second to realize this was who Dave was talking to.

    Dave’s eyes were on me while he bobbed up and down on the fake cock while the strange man stroked harder on the screen. “Ohhh yeaaaa! I’m gonna cum from watching you, you little faggot!!” He said.

    “What the fuck is this?” I whispered quietly. But apparently it wasn’t quiet enough.

    “Is someone there?!” The man on the screen asked.

    Dave stopped sucking. Glanced at me, then back at the screen as he pulled the cock from his mouth.

    “No no it’s just—“ Dave tried to say, but the video feed clicked off, and the fat white guy was replaced with a black screen that read ‘Connection Lost’.

    “God DAMN IT!” Dave yelled. Smacking his desk so hard that the dildo swayed back and forth. “What the fuck, Tom?! That was one of my most important clients!! And he was about to cum!! Now he may never come back!!”

    He looked like he was about to cry.

    I didn’t know what to say. “I...i’m sorry i...i didn’t know what...”

    “What the fuck do you want anyway?!” He asked. Obviously frazzled and frustrated by whatever was going on.

    “Well i was hoping that ummm...” but it all sounded so stupid now. Maybe it sounded stupid before? “You see...i haven’t cum in a while, and i was hoping you could umm...”

    “What? You want me to make you cum too?” He asked. Suddenly perking up like a hobo offered crack. “Whatta ya want? A blowjob? I’ve gotten pretty good! I’ll just have to video it if you don’t mind...”

    “Well uh...i don’t think that’d work see...on account of i’m in chastity and all...” i said, tapping my diapered crotch so that the hard metal could be heard above the crinkle. “So i was hoping maybe you could...fuck my ass instead?”

    It was one of the weirdest conversations i’d had in my life. Dave studied me for a second, then laughed.

    “Sorry bud...” he said, “but i’m in the same boat.”

    He stood up and undid his belt buckle. Dropping his pants down and showing his big, pink, princess diaper. He shuffled forward and peeked the front of his diaper open, allowing me to look inside and see his 7 inch dick tucked tightly in a cage only slightly bigger than mine.

    “Stephanie locked me in it after that awful date we had where I molested her.” He said, his voice cracking a bit. “She said the only way for me to get unlocked was to make 30 guys cum.” He wiped away a tear, “i have to show her video evidence of every fucking person i get to jack off for me. Turns out it’s a lot harder than you’d think. I’m only at 18 so far. And you just ruined my chance at 19.”

    I didn’t know what to say. All this time Dave had been fighting the same problems I was facing. Well, minus the whole boss-fucking-your-wife thing.

    “ you mind if maybe i borrow that dildo for a bit?” I asked sheepishly.

    “What? So you can fuck your own ass with it and give it back for me to suck on?!” He asked incredulously. “I don’t think so buddy! You’re gonna have to find your dick somewhere else...and i wouldn’t recommend the internet or chatrooms...”


    On my way back down the hall to my cubicle, I passed by a coworker named Brian. I stopped for a second, thought about it, sighed, turned and said: “Hey Brian...”

    He did a double-take. Probably wondering why I was speaking to him for maybe the third time in three years. He raised his eyebrows in perplexity.

    “Uhh...” i stammered, “You’re gay right?” I asked. Immediately regretting the brashness of my question.

    Again he looked confused, but nodded. “Yea...”

    “Well...i was just thinking...” i said, sweating, “maybe you and I in the bathroom some time...” I cringed at my pathetic attempt to proposition him. I hoped he didn’t find it as crude as it felt.

    But he did.

    “So let me get this straight...” he said after a long while. Stroking his beard and looking at me quizzically. “You think because i’m a gay man, i’m willing to just have sex with any guy that invites me on the wonderful prospect of ‘meeting them in the bathroom’ —of all places??”

    He looked like he was about to hit me. Clenching and unclenching his fist. Breathing hard. I squinted and waited for the blow to come. But it never did. When i peeked one eye open, he was gone.

    “Someone’s getting a little horny aren’t they?” said a voice behind me. I turned to see Stephanie, the secretary, smiling wickedly at me.


    “Save it.” She said. “If you really want to be a little slut and beg for cock around the office, I have the perfect prospect for you.”

    I hated how pathetic it was that a beautiful woman like her was helping me find dick to satisfy me. Like i was some kind of crackhead desperate for a fix.

    “You know Steve, over in Accounting?” She asked.

    I shook my head, hoping I wasn’t thinking of the big, fat, balding guy that was always dripping sweat every time he walked over to the water cooler.

    “He’s the big, fat, balding guy that’s always dripping sweat every time he walks over to the water cooler.” She said as if reading my thoughts. “He’s also a virgin.” She said with a wink before walking off. Probably headed towards Dave’s office to check on his progress of making 30 men cum.


    Steve’s cubicle was not exactly as secluded as I would have liked it to have been. But i was too horny to care.

    I tapped on the plaster next to the gap that represented his doorway.

    “Hey there, Steve is it?” I said. Trying to sound casual.

    Steve’s chair screeched under his weight as he turned around.

    “Yes?” He said gruffly. His multiple chins furrowing as he tried to decipher who I was and why I was there.

    “I’ve got a proposition for you...” i said, hoping i sounded like one of those smooth guys who pick up chicks.

    “What is it?” He asked impatiently, wiping the spittle from the side of his mouth and dabbing the sweat from his forehead with the back of his hand.

    “Well, i’m just gonna come right out and say it, Steve: word on the street might be a that true?” I said. Casually playing with a pen i’d found on his desk.

    “Uh...” Steve’s suspicious nature switched to that of mild embarrassment, followed by feigned fortitude, “i guess that is technically true...”

    “Well i think i can help you with that Steve...” i said.

    He shifted in his chair, which groaned like a banshee under his massive weight. His shirt coming untucked from his wide hanging belly and already saturated with pit stains. I tried to hide my disgust.

    “Oh yea?” He asked, chuckling awkwardly. Trying to downplay how excited he was getting. “You got a girl lined up for me?”

    “Not exactly, Steve...” i said, continuing to fidget with the pen, “you see, there are can take. Maybe from someone’s...backdoor...instead.” I said. Hoping he caught my drift.

    “I don’t follow.” He said.

    I reached out and covered his hairy hand with mine. Trying to sound like one of those thirsty girls at the bar. “I’m talking about me, Steve.”

    He snatched his hand away as if i’d burned him. “Uh...sorry...” he stammered, “I...i’m not into guys. I’m into girls!!!” He exclaimed. As if trying to convince a crowd that wasn’t there.

    “But are girls into you?” I asked.


    30 minutes later the door to the broom closet opened. I honestly didn’t think he’d show up. But there he was.

    “Alright...” he said as he closed the door, looking around nervously. “Let’s get this over with...”

    He tried to act nonchalant and confident, but i could tell he was actually nervous and sweating even more than usual.

    I smiled and walked up to him, wondering if i should kiss him or something to make this more romantic. Then i realized i’d never kissed a guy before and how weird that would be, so i just got down on my knees so I could suck his dick instead.

    After unbuckling his pants and dropping the massive amount of fabric to the floor, i expected his dick to be ready and poking me in the face. But even with his pants down, I couldn’t see it at all from my vantage point. It was hiding under his flab. He graciously lifted up his tummy as his breathing quickened in anticipation.

    Underneath his folds and forest of unkempt pubic hair was a tiny nub about 3-and-a-half inches long. It was purple and dripping already. I cringed as I closed my eyes, amazed at how far i’d fallen. How low i’d go just to get what I needed. I took his tiny dick into my mouth, feeling like I was sucking on my thumb as my diaper crinkled beneath my slacks.

    The goal was to get him lubed up so he could get it in my ass. Though I doubted he needed much to fit into my hole. Unfortunately, after only two sucks with my mouth, he was already cumming.

    “Mmmphh!!” I said with his prick still in my mouth. Taking all the cum and swallowing it out of habit. “What the fuck was that?!” I barked after I gulped it down. “You came already?!”

    “S-sorry i...” Steve said, turning a deep shade of purple. “J-just keep going...i can get hard again...” he said, sounding more and more pathetic.

    I sighed. Wanting to storm out and be on my way. But I was so desparate. So i kept sucking. Slurping his tiny cock that was now shriveling up to less than an inch.

    Finally, after about 10 minutes of licking and sucking his salty balls, his cock started to stiffen. I didn’t waste any more time lubing it up. Just stood up, turned around, and started pulling down my pants with renewed vigor.

    “What the fuck is that?!” He asked after seeing my soaking wet diaper that i carefully pulled down.

    “Don’t worry about it. Just shut the fuck up and let’s get this over with...” i said, bending over and spreading my asscheeks for him.

    He seemed very reluctant. I guess the shock value of it all was finally hitting him. But i didn’t give him time to hesitate as i backed my ass up into him, and he snapped out of his reverie to stuff his cock into my hungry hole.

    It felt good to have something in there, but I was immediately disappointed by how little he was able to fill me. I’d grown accustomed to having Charles’ python snake its way through my intestines, but Steve’s tiny member left me feeling like I was just getting fingered.

    Regardless, I was going to make the best of it. I slowly started building a rhythm, and was surprised how good it was starting to feel as Steve managed to hit my spot. He was helpless, his inexperience showing. I was like the sluttly cheerleader having to show him the ropes.

    “There...right there...yes! YES!” I moaned, “oh god! I’m actually close! Please don’t cum yet!”

    But just like all those times with me and Amy when she would say the same thing, I felt a warmth start filling my insides. Steve had cum. And i didn’t get my orgasm.

    “S-sorry...” he said.


    “So how was your day, baby?” Amy asked as she turned the water off to the tub. She had insisted on bathing me lately. Saying it helps to make me feel like a ‘helpless baby’.

    She was absolutely right.

    “It was fine...” i said, attempting to entertain myself with a rubber ducky and a toy boat.

    I tried not to get turned on as she started rubbing me down with a sudsy loofah. But i was trapped in a constant state of arrousal.

    “Maybe we should take this off so we can get it clean?” She said, tapping my caged cock. “With how messy your diaper was earlier, there’s probably all kinds of bacteria in there now...”

    My heart leaped. Was she finally going to let me cum?! I couldn’t contain my excitement as she pulled the tiny key off of her necklace and slid it into the lock. I felt like a prisoner getting their chains broken as she slid the tubing off, allowing my dick to breathe for the first time in weeks.

    “Now don’t get too excited...” she said as she noticed my instant erection. “You won’t be cumming in the tub today...”

    My mind was moving a million miles a minute dissecting her every word. So i won’t be cumming in the tub, or i won’t be cumming today...? I thought.

    I tried to control myself as she sensually rubbed my entire body down with the loofah.

    After she drained the water and had me stand up so she could dry me off with a pink unicorn towel, she still hadn’t put my cage back on. She stood up off of the toilet she was sitting on while bathing me, and I couldn’t help but stare longingly at that too. When was the last time I’d used one of those?! I thought, genuinely unable to remember being able to do something so simple as pee in a toilet and flush it all away without having to wear my warmth around for the next few hours.

    “Awww!” Amy cooed, following my gaze, “somewon misses the big girl potty don’t they?!”

    I nodded and sniffled.

    “Awww...well...why don’t you get in front of it...” she said.

    Again my heart leaped. Was i really gonna get to cum and use the potty in the same day? How lucky was I?! I thought as I scurried over in front of it. Feeling like a real man with my cock out standing over a toilet again. But before i knew it she was knocking my legs forward so that my knees buckled.

    “Babies like you don’t stand in front of the potty!” She said. “This is for GROWN UPS!” She barked. “In fact...why don’t you bow down and kiss it! Kiss the toilet and tell it how much you miss it!”

    I whimpered as I obeyed her command, placing my lips on the lip of the bowl where the seat was up. Apparently Charles had poor aim, or i did a really poor job of cleaning it yesterday because it was dirtier than i would have liked.

    “Look at you! So pathetic! And your fucking dick is STILL hard!” She laughed. “Put it on the toilet!” She commanded.

    I was terrified, but after all this,maybe she was gonna finally let me pee, just on my knees like a loser. I placed my hard cock on the lip of the bowl where i just kissed. Trying to mentally switch my cock from “horny” mode to “pee” mode.

    But Amy slamming the seat down on to my cock switched it immediately to holy-shit-that-fucking-hurt mode.

    “I didn’t say ‘pee’!” She yelled. Keeping the seat on my cock. “I want you to fuck it! Fuck the toilet while you tell it how much you miss it!”

    You’ve got to be kidding me. I thought. I felt so ridiculous. So humiliated as i started working my dick back and forth in the tiny space between the seat and the bowl. It was not comfortable, but at this point I would take anything.

    “Oh...potty...” i whimpered, “how much i’ve missed you! I wish i could use you so bad! Well know...i...oh i just miss using you!” I hated how stupid i sounded as Amy cackled laughing at me, but i could feel myself getting close to cumming. My excitement building.

    Only for it to be ruined abruptly by Amy stomping down on the seat, hard. Pinching my cock painfully.

    “Did i fucking say you could cum?!” She hissed while i writhed in pain. “Now let’s get your cage back on, potty-fucker, before you get too excited and spew your wittle load after only 20 seconds!”


    I spent the next few days in further frustration and agony. Steve and I would keep sneaking away to the broom closet at work, only for him to cum in a measely 30-45 seconds. Not nearly enough time for me to achieve an orgasm or even so much as a few dribbles.

    As much as it pained me to admit it, I really missed Charles’ cock up my ass. But he and Amy were so busy doing it with each other that he hadn’t even let me suck his dick in a while.

    That didn’t stop them from feeding me the loads though. I was getting so sick of the taste of dick sweat and salty semen from a used condom. But after that night it would all change.

    “I’ve got a surprise for you tonight.” Amy said as she changed my diaper after i got home. She had a coy look on her face that I couldn’t tell if it was more sinister or mischevious.

    “What is it?” I asked. Trying not to get my hopes up, but my horny brain couldn’t help itself while she wiped me down.

    “You’ll see!” She winked, sliding my super soggy diaper out from under me and rolling it up.

    “Can i have a hinty hint?” I said, in my toddler voice. Knowing it was more likely to win me points.

    “Let’s just say you’ll get a chance to cum in a warm, wet pussy tonight.” She said, winking.

    I spent the next few hours trying to decipher what that meant. Was she finally going to let me fuck her? Surely not. But that didn’t stop me from picturing it. Remembering how it felt to be inside her. The warmth and wetness of her pussy as I was able to pound her with my fully erect penis.

    But my cage snapped me out of my reverie as my cock attempted to get hard again.

    Amy and Charles were on the couch cuddling and watching TV when I came in after finishing up the dishes.

    “Are you ready for your surprise?” Amy asked, lifting her head off Charles prominent chest.

    I nodded. Quivering under their gaze.

    “Okay...” Amy said, climbing off of Charles, “Meet me in the bedroom in 5 minutes.” She said seductively as she sashayed by. Leaving me and Charles in the living room.

    I stood there awkwardly for what felt like forever. Unsure what to say. I thought about just leaving the room and waiting in the kitchen. As i turned to go, his voice came.

    “I don’t know what she has planned for you.” He said without taking his eyes off the TV “But if she wants you to have sex with her, you will refuse.”

    “I...what?” I said in disbelief, “but that’s my wife! I have every right to have sex with her!”

    “And you belong to ME now!” He roared. Finally turning his head to me. “And you will do as I say and I command! Or i will make life MUCH worse for you! Do i make myself clear?!”

    I cowered in fear. I wanted to be strong. To stand up for myself. But this man had broken me. I felt a sudden rush of warmth in my diaper. I had just wet myself. I cringed at how pathetic i’d become. I nodded in compliance “y-yes sir...”


    I knocked on the door to the bedroom.

    “Come in” said Amy softly.

    The room was dim when i entered. The only light coming from a few dozen candles she had lit. She was laying on the bed in nothing but a sexy black lingerie outfit.

    “Hi honey!” She cooed. “Come on in...”

    I tiptoed in hesitantly. Standing at the edge of the bed and trying to keep my cock from busting through my cage at the sight of her.

    “Do you know what tonight is?” She asked. Rubbing her hands along her half naked body and fiddling with her hair.

    “N-no...” i said. Shaking my head.

    “It’s our anniversary!” She smiled. A bit taken aback. I couldn’t believe i’d forgotten. With all this stuff going on and my world being upside down, i guess it slipped my mind. “It’s also been exactly one month since you’ve been caged. You’ve gone a whole month without cumming! Like we’d originally planned! Today’s the day you get released!”

    She pulled at the chain from around her neck, the tiny key dangling between her vuluptuous breasts.

    Before i knew it, she had the tiny lock off my cage, and my dick was breathing cool, fresh air.

    She giggled at my instant erection.

    “Awww! Is somewon ready for their warm wet pussy?!” She teased. Shifting around on the bed so that she was right in front of me. Legs spread. Pussy glistening.

    I couldn’t believe this was happening. After all this time i was finally going to get to have sex again. How i longed to be in there. But Charles’ threat loomed in the back of my mind.

    “I...l’m sorry honey...” i squinted as i forced myself to say it “but i...i can’t...”

    She stared incredulously. “Can’t what?”

    “I can’t have sex with you...”

    With that, she tilted her head back and roared with laughter. “Ohh sweetie! You thought i was going to fuck you?! You thought I was going to let you in MY pussy?! Oh sweetheart...i could never go back to your tiny dick after Charles! You think i got dressed up like this for you?! It’s for HIM!”

    She reached behind her back and pulled out something. Plopping it on the bed between her legs. It was one of my soaking wet diapers from earlier, rolled up into a little tunnel with the letters “P-U-S-S-Y” written across it in sharpie.

    This is what you’ll be fucking tonight!” She said.

    My heart sank. I don’t know why I got my hopes up. I don’t know why I even let myself think I had a chance. But i guess at least i wouldn’t have had to turn her down the way Charles intended.

    “But there are rules” she said after she managed to stop cackling, “for every hump you make inside that pissy ‘pussy’, you will spend one week in chastity.”

    I groaned. Conflicted. It was like every aspect of tonight was a double-edged sword.

    “Well?” She asked after what must have been a while. “Do you want to cum? Or should i just put you back into your cage indefinitely?”

    I shook my head. Trying to hide my shame as I aimed my 4 inch dick into the small opening at the front. It actually slid in pretty easily. It was still warm and wet from earlier. But it wasn’t exactly pleasant.

    Still. I started humping. Trying to make quality strokes. Trying not to think about the weeks that were ticking by with each pathetic hump.

    “That’s one month...” Amy said after 4 strokes, “now 2...”

    Already i was up to 10 weeks. I thought i was going to die after being locked for the last 4. How had my life come to this?!

    Just then the door creaked open behind me.

    “Oh hi, Charles!” Amy smiled genuinely, “Come to watch the show?”

    “Just wanted to see what ya’ll were up to...” Charles chuckled, sounding a bit relieved.

    “Tom just racked up 3 months in the cage so far...” Amy explained.

    Tears streamed down my face at the gravity of the situation. I still was nowhere close to cumming with everything going on.

    I stopped.

    “What’s the matter Tommy?” Amy asked, “do you not like your pussy?”

    I sobbed. Shaking my head no. I hit my knees, and did the only thing i could think of.

    “Will...will you let him fuck me instead?” I pleaded. Staring up at my gorgeous wife.

    “You want Charles to fuck you in the ass? Instead of fucking your little wet diaper?” She clarified. A bit taken aback.

    I nodded pitifully.

    They both laughed. Amy pondered. “Hmm..i’ll agree as long as you wear your cage. I don’t want your little dick hanging freely and you getting any ideas. But you will also need to ask Daddy...”

    I turned. Accepting my shame. Accepting what my life had now become. And trying to milk any bit of satisfaction i could get from it.

    “Daddy...” i said, looking up at his smug fucking face, “will you please...please fuck my ass. Please. I need it... I so desperately need it.”

    Again they both laughed at my expense. Charles looked from me to my wife. Then back at me, and nodded. Dropping his pants.

    Amy got my dick back in the stupid cage while I took Charles cock in my mouth to serve as lube.

    Before i knew it I was turned around and bent over the bed, my head in Amy’s lap. She stroked my hair like an affectionate mother as Charles pressed the head of his cock to my hole.

    Already I could feel the difference between his dick and Steve’s as he pressed inside me. The initial entry was always painful, but after just a few seconds, that pain turned to ecstasy as he filled me up, and started pounding.

    My eyes rolled in the back of my head. I buried my head in Amy’s legs to hide my look of pleasure, but Amy lifted me up and stared at my gaping ‘O’ face.

    “I can’t believe what a sissy slut you are!” She said, shaking her own head.

    I ignored her and just focused on the big, fat dick inside my hole. I don’t remember it ever feeling this good. Steve would have came 3 times by now. Leaving me unsatisfied. But Charles—Daddy—just kept going. Right into my P-spot.

    “Ohhh yes!! Daddy!!” I moaned. “Yesss!! YES!! Ohhhh i’m gonna cum!! Yes! Please! Don’t stop!! YESSSS!!!”

    The pressure built from inside. Rising to levels i’d never felt. Then erupted in pure bliss as my dicklet erupted inside my cage. Spewing my sissy goo all over the bed and floor.

    “Oh my...” Amy gasped. She probably had never seen anything like this before. “ looks like we won’t be needing to take that cage off in three months, or even 12 months, after all, huh?”

    To be continued

    The Boss’ Baby - Part 13 Dinner

    If you Need Start from the Beginning, Click Here to Read Part 1

    Click Here to read Part 12 

    I was sucking and licking every part of his cock. Head, shaft, balls, the space between, and the space underneath. Anything to see if I could get a hint of a taste of my wife’s pussy on his dick.

    Amy had just left. She had taken me to the bathroom to change my diaper on the floor. Ironically in the same spot Stephanie the secretary does. She spoonfed me mushy peas and carrots. Then squeezed the front of my diaper, kissed me on the cheek and said “Have a good day! Tonight’s gonna be a big night!”

    Shortly after I was resuming my daily duty of blowing Charles. It was the most paranoid i’ve ever been while giving him a blowjob. What if i taste some of her juices? What if she’s actually fucking him?!

    I continued to slurp and suck. Not tasting anything other than the slightly salty, fleshy meat of his big black cock.

    “Something wrong?” He asks. As if my sour face is any different than the other time i suck his dick.

    He continues to smirk at me, as if knowing the internal struggle i’m facing.

    “Did you fuck her?” I say. More aggressively than i thought possible. “Did you fuck my wife?”

    He smiles down at me for a long while in silence. Obviously taking pleasure in the fact that every second makes my insides churn in anticipation.

    He chuckled and didn’t say anything else. Just pushed my head back down on his dick and made me continue sucking.


    When I got home Amy already had something going in the kitchen. The sizzling sound and aroma got me hungry for a meal other than mushy peas and carrots, but then I remembered who all that cooking was for. 

    Amy was sauntering through the kitchen, sashaying her hips as she whistled a bouncy tune. I hadn’t seen her this excited to be cooking dinner in years. 

    “Oh hi honey!” she said. Pecking me on the cheek. “How was the rest of your day?”

    Well I sucked off my boss to try to see if I could taste you on his dick was probably not the best way to answer. Still, I was sure they had been up to something in the office before I came in.

    She was already dressed in a short, sexy mini dress. With a skirt that furled out in the breeze of her strutting back and forth through the kitchen. Her makeup and hair were flawless and her red lipstick stained the side of the wine glass she was sipping.

    “Do you need me to change your diaper before Charles gets here?” she asked nonchalantly. Like she was asking as simple of a question of if I grabbed the mail today. Not even bothering to turn away from the stove to look at me.

    I wriggled in my moist diaper. “Umm...yes i do...” I said. 

    She smacked her lips and sighed. Turning around to squeeze between my legs in an annoyed fashion. As if I were interrupting her cooking show for an inconvenience.

    “You’re barely even wet...” she said, rolling her eyes as she flipped me around. Peeking with a finger into the back of my pants “and you don’t even have poo poo! What the fuck would you need a change for?!” she asked. Scoffing and returning to her work.

    “Now go set the table! Charles will be here any minute!”


    The doorbell rang about an hour later. Amy jumped at the sound and her expression changed from concentration of getting the centerpiece just right, to sheer joy as she realized who was at the door.

    “He’s here!” she smiled. Darting past me and rushing to the door.

    “Oh hi Charles!” she said, barely containing the excitement in her voice.

    Charles was grinning from ear to ear on the front porch behind a beautiful bouquet of flowers. “Hello Amy! These are for you!”

    Her face turned deep red as she smiled in glee and sniffed the flowers. They leaned in to kiss...each other on each cheek. But my heart plummeted in that moment. They almost looked like a romantic couple that had to physically restrain themselves from kissing on the lips out of habit.

    “Tom, how are you this evening?” Charles asked as he shook my hand with a firm grip. His smile never leaving his face as he looked down on me like the wicked superior he was.

    “Dinner smells fantastic!” he said. Shifting his gaze back to Amy who couldn’t seem to decide what to do with her feet as she shifted back and forth frantically.

    “Thank you!” she said, finding a vase to put the flowers in as Charles sat down at the head of the table, usually my spot, but he didn’t seem to notice or even care. 

    I sat catty-corner to him as Amy came in with three plates of Filet mignon. She put the plates down in front of each of us and I noticed mine had the steak already cut up into tiny little bites. As if for a 3 year old to eat. I expected her to sit right next to me, furthest from Charles. But instead she sat across from me, also catty-corner to Charles.

    “Oh! I forgot! Can I get you anything to drink, Charles?” she asked as soon as she sat down, “That was so rude of me i’m sorry i--” but Charles stopped her as she made to get back up.

    “That’s okay Amy!” He said smiling, “Tom will get it.”

    Who the fuck was this guy? Coming into my house and ordering me around? Who the fuck do you think you are? I wanted to say. But I didn’t. I was too scared of what he might do to me in front of Amy if I disobeyed. I almost even muttered out ‘yes sir’ as I snaked out of the table and went to grab the bottle of wine.

    When I came back they were already chatting. Amy laughing hysterically and practically ignoring me as I filled her wine glass and then Charles’. 

    “Ummm! Not for you!” Amy said through laughter as I went to pour my own glass. “Yours is already in the fridge!” she smirked.

    I sighed as I went to the fridge and, sure enough, there was a glass of wine already poured and waiting inside. Not in an actual wine glass, mind you. Instead it was sitting inside of a much shorter, clear hard plastic cup. It looked like a sippy cup with the top removed.

    I flushed in shame as I headed back to the table, where Charles and Amy were sill talking as if I weren’t even around. Amy was leaning on her elbow in his direction, barely even sparing me so much as a glance as I sat down.

    “ then I said: ‘Tom! That’s not the Beuterman file! You need to be a ‘Better man’ about this!” Charles chuckled and Amy laughed exaggeratedly.

    “Hahaha yes well, Tom could really do with being a much better man some times!” she chided.

    I didn’t say anything. Just stared down at my plate. Taking an undersized bite of steak and sipping my wine through my little plastic cup. Which I suddenly realized wasn’t even wine, it was just grape juice. She smirked at the face I made expectantly. She was babying me in front of Him without deliberately doing so.

    “Hahaha well he has his faults but he can be good for...some things...” Charles said, winking at me as he sipped his actual wine. It was like each were in on their own inside joke with me. Thinking neither was the wiser. Charles knowing i’m his personal office slut and Amy knowing i’m her personal baby. Well, Charles knew it all, but Amy didn’t. Unless he told her?

    They continued chatting and laughing and practically flirting right in front of me like I wasn’t even there. I could feel the anger building inside me. The one i’d bottled up over the past few days at the idea of them fucking each other behind my back.

    “Are you two sleeping together?!” I blurted out before I could contain it.

    They both stopped mid-laugh. Amy’s fork clanked against the plate. They both stared blankly for a second, then glanced at each other.

    Amy hesitated for words. Stuttering and stammering a bit. I felt like the answer was what I expected.

    “No.” Charles finally said.

    It caught me off guard. I was so sure of it. I...

    “B-but then...who were you with last night?” I asked Amy.

    “I told you, Tommy.” Amy said, flipping through her phone, “I was with my girlfriends. Callie, Courtney and Renee”

    She showed me her phone and started flipping through pictures of her and the girls at various clubs in the same dress she wore last night. Charles’ look of confusion seemed to confirm that he had no idea what I was talking about.

    “I...b-but...i thought...”

    “Honestly, i’d be lying if I hadn’t thought about it.” Amy said. Nodding at my plate with the cut up food and sippy cup of juice as if that told me everything I needed to know without her deliberately having to say i’m not exactly turned on by all your diapers i’ve been changing recently. “But I would never cheat on my husband.” She said definitively.

    That was when Charles let out the most evil, wicked laugh i’d ever heard him use. He sounded like a movie villain.

    “Hahaha that’s funny!” He said, continuing to guffaw. “Because I don’t think Tom here shares those same values as you do, Amy...”

    It was like he had punched me in the stomach. I couldn’t breathe. My life literally depended on what his next words would be.

    “Because you see...Tom has been cheating on you all along, Amy.” He said.

    Amy’s expression changed. She looked back and forth from me to Him frantically. “Wh-what? What do you mean?! It couldn’t be! He couldn’t have...he he’s...”

    “Locked in chastity?” He finished. Amy’s jaw dropped.

    Charles laughed again. “Yes, how would I know that? Hmm?” He was grinning from ear to ear as he grabbed his briefcase and set it on the table. Unfastening the clips, opening it up, and pulling out a manila folder. I thought my heart might beat out of my chest.

    “About 2 months ago we found several hits to our work servers coming from Tom’s IP address for pornographic material. ‘Sissy sucks cock’, ‘sissy cumshots’ and ‘sissy cuckold’ all being searched most frequently.”

    Charles pulled a list of all the terms I’d used to search (in what I thought was incognito mode) on my work computer. Each one more incriminating than the last. Amy’s eyes and mouth widened as she read through them all.

    “So I called Tom into my office, and spoke with him about the pornographic content.” He looked at me and smiled “that’s when Tom first came onto me.”

    “That’s not true I—”

    “Quiet!” Amy barked. Glaring at me. Her face was flushed. She turned back to Charles for more, as if his word were more trustworthy than mine.

    Charles pulled several photos of me in lingerie out of the folder. Laying them out on the table for Amy to see. “He tried to use these to seduce me...” he lied. In reality, those pictures came days later after Charles had started blackmailing me. But there was nothing I could say to make Amy believe that.

    “I’ll admit,” Charles explained, “that I was a weak. Lonely man at the time.” He said shaking his head. He even made to look like he was wiping away a tear! “So i hesitate to show you these next pictures...”

    There, in a full page photograph, was me on my knees. Charles’ cock filling my mouth. Then another one of me smiling (reluctantly, for fear of getting spanked) with a load of his cum on my face.

    Amy burst into tears.

    “Amy it’s not true! I didn’t like it! He made me! Please!!” I tried to beg. But the look of betrayal in her eyes was paramount.

    “Unfortunately,” Charles continued, “Tom couldn’t be satiated by just me...” and he showed her more photos from the folder showed me sucking off Dave from IT.

    “He even tried hitting on my Secretary Stephanie.” Charles said, “even went so far as to asking her to diaper him. She sent me this video...”

    He clicked his phone and a video played. All i could hear was my pathetic voice saying “Please Stephanie...will you please change my diapurr?!”

    Amy looked shocked. “S-so...that’s why he was wearing diapers that day. Not because he wanted me to have a ‘baby’. Because he wanted people to treat him like one for his own perverted needs!!”

    “Eventually he became so insatiable” Charles went on, as he showed a video of me begging Stephanie to let me cum in my poopy diaper “that Stephanie suggested he get a chastity device”

    “And he made me think it was his idea” Amy’s tears were dried now. This weird, fucked up story was all making sense in her head. Even if it was...mostly...untrue. Her betrayed brain made her believe it to be so.

    “Oh come on honey!” I exclaimed, “are you really gonna believe this shit?!”

    “WHAT DID YOU JUST SAY?!” Charles roared. His tone and volume startled Amy and I both. More so me, because I knew when the lion was angry it was hard to put back in its cage. “You will NOT speak to her like that!” He growled.

    What little resolve I had was quickly deflated. I was left cowering and crinkling in my chair as Charles stood up.

    “Bend over!” He commanded.

    “N-n-no please! I’m sorry I—“

    But he had already grabbed me by the scruff of my neck and forced me over the table. It was like we were back in his office and he was bending me over his desk. Only this time it was in my own dining room right in front of my wife.

    I expected her to come to my aid. To put a stop to all this madness. But instead her face was aghast in awe. It was like she was mesmerized by the power Charles had over me, and she wasn’t about to put a stop to it.

    “Drop ‘em” Charles demanded as he removed his belt. I begged and pleaded as I fumbled with my own.

    “P-p-p-please don’t this! I’m s-s-sorry s-sir!! I’m sorry!!” I must have looked so pathetic. Blubbering like a baby as i dropped my pants to my ankles and exposed my large, now soaking wet, diaper.

    Amy gasped as the first lash of the belt hit my thighs. Not in fear, mind you, but a gasp of admiration. Was...was she turned on by all of this?

    I tried not to squeal as the leather strap pelted my backside but I couldn’t help it. Charles was doing his best to show Amy what a pathetic baby i’d become. And it was working perfectly.

    Swat after stinging swat blistered my legs until it finally stopped. I was relieved. My tears were making puddles on the pictures of me in lingerie littering the table. I made to stand up, but Charles pushed me back down. Apparently he wasn’t done.

    I felt the tapes of the diaper being removed, and the soggy padding plopped to the floor with a dull thud. My bare ass was now exposed. A white canvas for Charles to paint red like my legs below.

    “A-amy!” I sobbed. “Help me...please...” it was my last-ditch effort.

    But she just sat there in front of me. Smirking. Her arms crossed. “What?” She asked mockingly, picking up Charles’ phone and playing another video, “isn’t this what you wanted?!”

    And she laid the phone down in front of my face. So i could watch myself humping the floor of the bathroom saying “thank you for letting me cum Miss Stephanie! I made pee pee and poo poos in my diaper just for you!!” While the first lash of the belt lit up my ass cheeks.


    After the little show at the dinner table, I was instructed by Charles to clean up and do the dishes. I knew better than to argue as Amy re-administered the soggy diaper to my now burning buttocks. She didn’t bother putting my pants back on. They were no longer necessary.

    While I was rinsing the dishes in the kitchen, I could hear them mingling on the couch. Any reservations Amy had previously had now evaporated. As they were now sitting right next to each other with no regard for personal space. Laughing as they sipped their glasses of wine.

    I so badly wished there was something I could do. Anything that would make me look more like a man in order to salvage this disaster. But no matter which way I played it out in my head, it never worked out to my benefit.

    Once the dishes were done I made my way back to the living room. They were silent at least. Maybe things were more awkward than they expected?

    But when i turned the corner i found out why their chatting and chuckling had stopped. They were both locked in a deep, passionate kiss. Charles’ big, giant hands on her back and butt, and Amy’s hands pulling his head into hers as they continued to make out like they were high school lovers.

    All i could do was stand their awkwardly. Fighting back tears as my wife made out with my boss right in front of me.

    Finally they disentangled themselves, and seemed to notice me for the first time.

    “Oh! There’ss the little cockshuckerr!” Amy laughed, slurring her words a bit from the alcohol as she wiped her lips. It was like an evil spirit had awoken within her. “Why don’t you get down on your knees?” She said, reaching a hand over to Charles’ pants, unfastening the belt he just used to whip me with. Charles made no objection; just leaned back on the couch and did his usual chuckle.

    “Honey doesn’t have to be like this...” i pleaded as I dropped to my knees.

    “Oh but it will be!” She grinned. Fishing in Charles’ pants for his cock. It wasn’t difficult to find. “Oh my...” she swooned when she felt it. Looking up at him, mesmerized at what was pulsing in her hand. I wondered if she’d ever felt one that big...

    Soon she had it snaked through his zipper and sticking up with all it’s big, black, veiny glory.

    “Let’s see what you got!” She said. “I want to see what a fucking cocksucker my husband is first hand!” She sneered, wriggling the black python in my face.

    I was so heartbroken. So ashamed. So defeated. “Honey...i...” but i didn’t get another word in before she had grabbed me by the back of the head and forced me down on Charles’ cock.

    “Theeerrrre wee goo!” She cooed, “wittle baby has his paci to keep him quiet now!”

    Obviously this wasn’t the first time I’d had Charles’ dick in my mouth, but it definitely was the most humiliating time as my wife was only inches away. I whimpered and choked as she forced my head up and down on it, making sure to mind my teeth.

    “Wow you are a fucking faggot aren’t you?!” She gasped. Removing her hand and allowing me to do all the degrading work. “Is this why you could never get hard enough to fuck me?!”

    I cringed at her hurtful words as I continued to suck and slurp the way I was trained to. I decided to close my eyes and try to shut it all out. After a while her laughter and teasing had subsided, and i figured she was through. When i peeked an eye open I could see they were making out again. I didn’t know what else to do but continue sucking....

    “I think it’s time we move this to the bedroom” she finally said.


    “Remember when I had to watch you cheat on me?” She hissed in my ear as she used Charles’ tie to bind my hands to the chair behind my back, “well now you are going to watch me cheat on you!!”

    She strutted her naked body around the chair and onto the bed. It was only a two foot walk for her. She wanted me to be as close to the action as possible. She even made me undress her first. I had never seen such a dominant side to her. But there were few things more emasculating than taking off your wife’s clothes so that she could get ready to have sex with another man. I tried not to pay attention to how soaked her panties were when I pulled them off.

    Amy’s hands moved to Charles’ clothes. She seemed to be worshiping him as she undid the buttons of his shirt, exposing his chiseled abs and biceps. He was every bit the man I wasn’t. All the way down to his nearly 10-inch cock.

    They collapsed on the bed and resumed their sensual make-out session. Their bodies entertwining. Her legs wrapped around his. Their skin glistening. Amy moaned softly.

    “Do you have a condom?” She asked.

    Charles smiled and pulled a Magnum XL from his wallet. He undid the wrapper. Pulling out the large rubber disc, he went to put it on, then hesitated. He grinned. Then looked up at me.

    He placed the ring to my lips. “Put it on for me!” He said. “Put the condom on my dick so I can fuck your wife!!” They both laughed hysterically.

    I whimpered as i inhaled the tip of the rubber condom. Begrudgingly, i leaned forward and aimed the ring around the head of his throbbing dick. I used my lips to push the ring and unroll the condom down his cock as it slid down my throat. I only made it about halfway. I withdrew, thinking I was done. But he stood there expectantly. I sighed, and took his rubber-wrapped dick back in my mouth and choked as I shoved the remainder of the condom down to the base of his cock.

    He chuckled again as he scooped up Amy’s soaked panties. Stuffing them in my mouth and smacked my cheeks softly. “Enjoy the show!” He said. Then turned back to Amy who was eagerly waiting on the bed. Even from where i was sitting I could see she was soaking wet.

    Charles climbed in between her and they kissed a bit more before he finally raised up and aimed his big, meaty python into her tight white vagina. I didn’t think there was any way it could fit in there, and apparently she didn’t either. We both held our breath as he gently eased it into her. But where my trepidation rose, hers melted away as her eyes rolled back in their sockets.

    “Ohhhh myyyy GODDDD!!” She moaned as he slowly filled her up. I let out a muffled whimper and tugged at my bonds helplessly as he started moving in and out. “It’s....soooo....BIG!” She exclaimed. But she welcomed every inch of it. Wrapping her legs around him and pulling him in further.

    That’s when he started thrusting. Building up tempo as he slowly increased intensity. “Oh! God! Yes! Yes! Oh my god YES!!” She moaned. Her arms clenched up behind her. Then splayed out. Then went through her hair. It was like she didn’t know what to do with them amidst all the euphoria.

    To my horror, i was actually becoming aroused inside my cage. I wriggled and crinkled in the chair. Trying to convince myself not to be turned on by my wife getting plowed by another man. But i couldn’t help it.

    “Oh god! I’m close!” She moaned. She was sweating. Her face was turning red as her orgasm built. “Oh please don’t cum yet!” She begged.

    Charles chuckled softly and glanced at me. We both knew he wasn’t even close. I would have came 5 minutes ago...

    “Yes! Yess! Yess!! OoooOoOOhHH YESS!!” Her body shuddered and quaked. I could see tremors course from her toes all the way up to her thighs and back. She rocked back and forth to what was probably the most explosive orgasm of her life. And Charles still had plenty left in the tank.

    “From behind?” She asked. And Charles obliged.

    She got on all fours facing me, while Charles got right behind her.

    “Look at how pathetic he is.” They both said in unison, then laughed as they continued fucking.


    “Looks like you enjoyed the show after all...” Amy teased as she wiped the sticky residue leaking through my chastity cage while she changed my diaper. I was too ashamed to say anything.

    She put me in a fresh diaper and helped me into the undersized crib I’d slept in the night before. “Honey...” i pleaded once more “it doesn’t have to be like this...”

    She slipped my wrists into the straps and cinched them tight. “I know it doesnt have to...” she smirked, “but it’s going to...” then she plopped a paci in my mouth, flicked on the baby monitor and walked out of the room without another word.

    Only the baby monitor was set up backwards. Instead of hearing everything happening in the nursery, I had to hear everything happening with Amy and Charles in the bedroom. And it went on all night long...

    To be continued

    Click here to read part 14

    “Becky? Hey! It’s me. So you know how i told you i had that babysitting gig today? Well get this: i’m babysitting a 37 year old! I’M SERIOUS! No like, he’s a full on baby and everything! I’M NOT JOKING! I’m looking at one of his giant diapers right now! And Becky it’s PINK! Yes! Like ‘little baby girl’ pink! Idk, i guess he pissed off his wife really bad or something because she’s the one who hired me. He’s just laying down whimpering right now. It is SO pathetic! He keeps grabbing the front of his diapers in his little pink onesie. Saying something about how i’m making his ‘pee pee cage’ hurt. No listen, you have GOT to get over here and see this! I think he just pooped!!!”

    Bound for Release

    “What’s happening?” I asked as she tightened the bonds on my wrists and ankles. “What are we doing?”

    Usually when she strapped me to the bed spread-eagle like this she would have me face-up, not face-down.

    “Were you told to speak?!” She barked. Smacking my ass with the riding crop.

    “Ah!! No mistress! Sorry mistress!”

    I was dressed in black, lacy lingerie. With little garters that went down to my legs but didn’t cover much of my ass at all.

    “Good gurl! Don’t make me add another week!” she said. Jiggling the metal tube that caged my poor, pathetic penis. My swollen balls were already aching, and her minor attention to that region—even in a stern manner—made them throb even more.

    She yanked my hair so that my head was forced backward and my mouth gaped open. A big red ball was stuffed inside it then belted tightly around my head.

    The fear of the unknown and what’s to come is the scariest part for any slave. And that feeling wasn’t eased by the blindfold she put over my eyes.

    Have fun, sissy!” She hissed in my ear. Then i heard her heels clank as she strutted out of the room, shutting the door behind her.

    I laid there in the darkness of my blindfold. Listening to the dull hum of the AC that was making my half-naked body shiver. Trying to breathe around the ball of the gag and the pillow my face was buried in.

    After what felt like hours, the door finally opened.

    “Come on. Inside.” Said a stern, commanding female voice. But the voice didn’t belong to my Mistress. It was someone else’s.

    I heard two sers of footsteps. I think. One sounded like they were in heels, the other’s was softer, like they were crawling on all fours. The two strangers both came behind the bed.

    “What is this, Goddess?” Said a soft, submissive male voice.

    “This is your reward!” Said the female. I could hear the faint jingle of keys. Tiny keys.

    “You mean it?!” The sub’s voice was quivering. Not with fear, but with gratitude. “Oh thank you Goddess! Thank you!!”

    There was the familiar sound of a key sliding into a miniature lock and unclasping the tiny prison of a chastity cage. I wriggled my hips, jealous that it wasn’t my own being unlocked.

    “Up you go.” She said. “Come on! We don’t have all day...”

    I felt the foot of the bed sag as someone climbed onto it. The springs of the mattress creaked as they inched closer. Then two hands were on my ass cheeks, spreading them apart as a glob of lube was applied.

    “Enjoy.” Said the female voice.

    I felt the fleshy head of a cock pressing against my hole. Up until now the only thing i’d had up my ass were plastic and rubber dicks, now i was getting the real thing.

    I groaned into the gag as the penis pressed inward. Only making it a few inches in, then out, then in a few more, until my sphincter starts to relax and all 6 inches of the cock were sliding in and out of my asshole.

    “Ohhhhh thank you Goddess!” The sub moaned as he started pounding away at my hole. “Thank you! Thank you! Thank youuuu!!!” He said with each thrust.

    All i could do was lay there and take it. Cringing and tugging at my bonds while he used me like a human flesh light.

    The throbbing of his dick in my rectum was different compared to the cold, solid plastic i was used to. I could feel his head swelling inside me.

    “Permission to cum, Goddess?!” He pleads, panting.


    He let’s out some really pathetic sounding moans, then starts to spasm behind me. A slightly warmer sensation fills my insides. “Ohhhhhhhh thankkk youuuuuu!!” His moans turn into sobs. He collapses on my back. Cock softening inside me, and cries. “Thank you Goddess!!” He sniffles.

    He slides his slimey member out of me and climbs off the bed.

    “You’re welcome, slave. Now it’s time to get this back on...” she says, followed by the rattling of the cage.

    He whimpers a bit, but seems to know better than to argue. Soon there’s the familiar *click* of the tiny lock.

    They both leave without another word.

    Leaving me still tied and now oozing with his built-up cum.


    An hour later the door opens again. Finally my Mistress is back for me.

    But it’s not her. It’s another lady with a soft, motherly voice.

    “Heeeerrrreee we arrrreee!!” She says.

    All i can here is a faint, rustling sound.

    “Are you excited?! You finally get to make cum cums!!” She says in a mocking, singsong tone.

    Nothing comes from the other person other than faint sucking like Maggie from the Simpsons. There’s the ruffle of something and then the sound of tapes being pulled off. Something crinkly drops to the floor.

    “Here you go baby!! Have fun!!”

    The mattress sags even more this time. This is a heavy one. I can feel his belly plop down on my back as he leans over me. Then i feel a finger enter my hole.

    But the finger is moving in time to his weight on my back and I realize it’s not a finger. It’s a tiny dick!

    “Oooh oooh goo gooo ga gaaaaa!!!” Comes the voice from behind as he shivers and spasms.

    Did...did he cum already? That was only like 5 strokes! I thought. But the woman answered for me.

    “Awwww!!! Honeyyy!! Did you go goo goo already?! HAHAHAHA! Oh my GOD!! You’re so fucking PATHETIC!! Do you see why I keep that wittle baby dick of yours locked up and in diapers?!” She cackled.

    I could feel the man sag behind me. Deflated and embarrassed. As he probably should be...

    It was pretty pathetic, and that’s coming from a guy who’s strapped to the bed in lingerie and just took it up the ass from two men...

    “Whelp! Let’s go!” The woman said after she finally contained her laughter. “Let’s get that wittle baby dick back where it belongs!! Maybe next month you’ll last longer!”

    The familiar sound of the cage and lock came first, and the unfamiliar crinkling and taping of a diaper followed.

    Out the door they went. Still not even bothering to acknowledge me.


    The next couple that came in sounded pretty normal. The guy had a big, burly voice that made me think he was the dom. But his wife sternly put him in his place, and the loftiness of submissiveness infiltrated his tone.

    His dick was much bigger. I clenched the mattress and squealed into my gag as he entered me. Fucking me like a horse in heat as he tore me in half with his giant member. He jammed me back and forth into my pillow so hard that he dislodged the blindfold, and I was able to glance back and see a beautiful woman in skintight latex watching with arms crossed as a big, white, bearded man flexed his eight-pack as he pounded me into oblivion.

    His groans drowned out mine as he emptied his seed into me 20 minutes later.

    He grunts as he slides his slimey python out of me.

    “Aren’t you forgetting something?” The woman says as he stands up. Her arms still crossed menacingly. “Do i need to remind you? You don’t get to cum without cleaning up.”

    The big Thor-looking man hung his head submissively. Then sighed. Apparently thinking he couldn’t face the wrath of the woman half his size. He turned and buried his face between my ass cheeks. Tonguing out his load of cum and the ones from the subs before him.

    It honestly felt kind of good to have his tongue on my now abused hole. But it didn’t last long. A minute or two later, he came up for air. His beard sticky with juices.

    He stood up and allowed the woman to somehow stuff his giant cock back into a chastity cage that was almost the same size as mine. He looked over, saw me eyeing him, and quickly rushed to my side to fix the blindfold. Plunging me back into darkness.


    “Inside!” Came the sharp voice followed by several smacks. “On the floor! Don’t look at me!” She ordered. Emphasizing each word with what sounded like a riding crop.

    “Pull up your skirt! Drop your panties!” There was an aggressive clanking as the cage was removed.

    “You have 60 seconds.” She said. “Your time!”

    Then there was a body on me. As if they literally jumped straight on the bed. They were breathing heavily as they fumbled for their cock and started prodding around my hole erraticaly.

    After they stuffed all 4 inches inside they started humping furiously. Not even bothering to do a slow build up.

    “25 seconds...” said the woman.

    The pace quickened. The man whimpered desperately.

    “15 seconds...”

    More whimpering. More grunting. More whining. “Please Mistress! I need more time!!” He cried.

    “Absolutely not...10 seconds!” She said unsympathetically.

    His grunts and whimpers were so pathetic as he tried as best he could to wriggle out an orgasm.

    “5....4....3....” he was so desperate. So horny. “2...1...STOP!!”

    He tried to wiggle some more but several hard swats with a crop put an end to that. “I said STOP!!”

    The man was crying. I could feel his tears raining down on my back. “Nooooo!! Pleeeeasssee Mistresss!! Just a little more time!!”

    His pathetic pleas went completely ignored. He was blubbering like a toddler as she readministered the chastity device. “Maybe if you earn me a couple more grand on the street corner you’ll get another 30 seconds. But that’ll take a couple weeks at the rate you suck dick, won’t it?!”

    His helpless cries lingered all the way down the hall, even after they’d left the room.


    The last one really pissed me off.

    “Thank you so much, Mistress! These three days have been absolute TORTURE!” He said.

    Three days? THREE days?! Are you fucking kidding me? I haven’t been unlocked in four MONTHS!! I thought. Enraged.

    The fucker couldn’t even get hard. Just worked his semi-limp noodle into me and squeaked out a tiny load 8 minutes later.

    I had some choice words for them when they left. But the ballgag made it all sound like muffled gibberish that they completely ignored.


    Finally the door opened and only one set of footsteps came in. Heels. It was my Mistress!

    After 24 hours in this room I was so happy just to even hear her.

    “Hello sissy! Did you have fun?” She asked, rubbing my back.

    I blinked tears away as I nodded “yes” knowing no other response would be acceptable.

    “Good gurl!” She said. Untying my sore arms. The light stung my eyes. I rubbed my wrists and worked my jaw as the ball gag was removed.

    “Is it my turn now, Mistress?” I asked. Sitting on the bed next to her. Feeling the loads of cum oozing into the sheets.

    “Your turn for what?” She asked. Genuinely confused.

    “My turn to cum?” I asked. Keeping my head angled down. Still afraid to bring it up.

    “Did you not cum from getting your wittle ass pounded by all those slaves?” She asked incredulously.

    “No mistress...” i said. As if it was something to be shameful of.

    “Oh...” she said, wrapping an arm around me sympathetically. “Well that’s too bad! Maybe next month you will!!”

    THE END.

    The Boss’ Baby Part 12 - The Night Out

    Author’s Note: I’m sorry it took so long for me to write such an underwhelming Chapter. But hopefully you guys will enjoy the next one better.

    Click Here To Read Part 11

    “Enjoying your cartoons baby?” Amy asked. Kneeling down next to me and smiling.

    I had spent the last hour on the floor of the living room inside the 18-inch walls of the “playpen” trying to find any form of entertainment I could out of the Barbie dolls she’d given me to play with. Some annoying show called Peppa Pig playing on the TV in front of me.

    I didn’t even reply. Just continued sucking on the over-sized paci in my mouth.

    She reached into the pen and pulled up the skirt of my frilly pink dress. Peeking underneath at my now soaking wet diaper. “Awwww! Wittle baby wooks wike she’s got pee pee in her Pampers!”

    My cheeks turned the same shade as my dress. Even after 2 weeks of enduring her baby talk, it was still super humiliating.

    “Lay back sweetheart! Let’s get your diapy changed before Mommy starts getting ready!”

    “Getting ready for what?” I squeak around my paci as lay back on the floor.

    She smirks slightly as she pulls the tapes of my diaper open. “Oh...just going out for the night...”

    My mouth gapes open, making my paci fall to the floor. “With who?” I ask, before she plops the paci back onto my mouth.

    “Some...friends...” she says, glancing about, “you know...girls night!”

    “On a Tuesday??” I ask incredulously.

    “Mhmm” she acts like she’s going to say more. But her phone buzzes. She scoops it up before i can get a look at who it’s from. She smirks again, then taps out a message. Her nails clacking against the keyboard while i lay there with my dress up and caged cock out in the open.

    Is it Charles? Is that who she’s texting?! I think, but don’t have the courage to say out loud.

    She hits send and looks back at me, as if forgetting I was even there. Then she smirks. “Awww! Why is your wittle pee pee getting all shrively in its cage?! It’s usually so excited to see me!” she giggles, tapping the hard plastic of the clear cage playfully.

    I couldn’t stop thinking about who she might be texting as she pulled the wet diaper from underneath me, rolling it up and taping it into a ball. Surely she wasn’t going out with Charles after only two days...right? I thought as she slid a pink diaper underneath my bum.

    She picked up the powder and applied it liberally to my caged genitals. Leaning over and blowing it into a powdery cloud. It was the closest thing to a “blowjob” i’d had in weeks.

    After she pulled the diaper over and taped it tight, her phone buzzed again. I tried to sit up fast enough to see it. Trying to get a glance at her screen. But my vision was interrupted by her handing me my rolled-up wet diaper.

    “Put this in the trash will you, baby?” she said, grabbing her phone and turning it over. “Also, I think the trash is getting full, you might have to take it out to the dumpster” she smirked.

    The dumpster was at the end of the street.


    Luckily it was dark. I’m pretty sure I managed to sneak outside and sashay down the driveway and back before anyone could see my dress furling behind me. But I still won’t be able to look my neighbors in the eye any more.

    When I came back in the house Amy wasn’t in the living room. I walked around to find her, Peppa Pig still blaring on TV. 

    I found her in the bathroom standing in front of the mirror in nothing but a black bra and panties. Looking stunning. Applying make-up to an already gorgeous face. She glanced over at me and smirked. Puckering her painted lips in a seductive way at the mirror.

    “Please don’t go...” I say pathetically. “Stay with me!”

    She laughs “I’m sorry honey but I already told...” she stopped as her phone buzzed again. She smiled and picked it up and started typing immediately as if I weren’t there.

    I stood there awkwardly. Clenching the hem of my dress and crinkling in my diaper as I shifted my weight.

    She set down her phone furthest away from me.

    “If you want you can...get between my legs while I get ready...” she winked.

    I knew exactly what she meant, and I was eager to please her. Thinking it might convince her to stay.

    I knelt between her legs and pulled down her sexy, black, lacy panties. They were already soaking with her juices. Was she that wet for me? Or because of what might be happening tonight?

    I tried not to think about it. Just tried to focus on convincing her to stay with my tongue as I worked it between her dripping lips. She tasted wonderful, and her scent made my cock poke instantly inside its cage. 

    “Mmmm...” she groaned. I glanced up to see her applying eyeliner to while her eyes rolled back in her head.

    Yes...i’m doing it! She’ll definitely want to stay--

    Bzzz! Went her phone. She scooped it up instantly. I made to move my head back to see but she grabbed my hair and forced me back into her crotch. Hard. I wasn’t used to her being that dominant as she made me continue licking to the sound of her nails tapping out a message on her phone.

    “Oh my goddd...i’m cumming! I’m cumming!” she forced my head further into her pussy. My nose smushed as I did my best to continue licking. “Yesss...yesss...YESSSS!!” she moaned. Convulsing and having to use her hand on the counter to steady herself as she climaxed. Breathing heavily for several seconds after.

    “So now will you stay?” I asked. Wiping my mouth.

    Her O-face changed to a loud cackle. “Hahaha no honey!” Sorry! But if you can lick my ass now?”


    30 minutes later she was in a black satin dress she had me pick out. I tried to pick the less sexy one, but she still managed to make herself look irresistible. My dick was becoming painful inside the cage.

    She checked her phone again. It was becoming very annoying. 

    “Oh look at the time! I need to go! Let’s get the wittle baby to bed, shall we?” she said. Hurrying forward and grabbing my hand.

    She led me out of the bathroom and even out of our bedroom, down the hall and into the room she had set aside for the future nursery of our baby we were never able to conceive.

    The room was pretty stripped down, but it had a crib she got for a good price that, again, we hadn’t had to use yet. Until now...

    “Get in.” she said, dropping the side railing down to the floor.

    “What?” I asked incredulously.

    “You heard me.” she repeated. “Get. IN!” and she nudged me forward onto the tiny mattress.

    “Honey...please! Noo!” I said, starting to sob. It wasn’t even the undersized crib, or the humiliation of it all. I just really didn’t want to face where she was going.

    “Shhhh...” she said, pulling a bottle from seemingly nowhere and placing the nipple in my mouth. It was a sweet, chalky taste. “Drink this dear, it will make it all better!”

    “But I don’t want you to go!!” I cried, realizing I sounded like an actual toddler who didn’t want their real mommy to leave them.

    “It’ll be okay! I’ll be back before you know it!” she cooed.

    I decided to play my final card. I pushed with everything I had until I forced a huge, messy, stinky load into my diaper. I could see her wrinkle her nose.

    “Awwww! Did the wittle baby go poopy?!” she giggled.

    I nodded furiously. “Yes! Now will you please stay and change me??”

    She laughed. Checking her phone again. “I’m sorry honey but I reallly don’t want to be late!”

    I cried. I begged. I pleaded as she used rope to tie my mittened wrists to the posts of the crib. It was all so pathetic as she kissed me goodnight and tucked a tiny baby blanket around me. 

    “Good night hubby!” she said as she turned off the light and headed for the door. “Sweet dreams!”


    “Wake up, honey! You’re gonna be late for work!” Amy said, poking through the bars of the crib.

    I don’t remember when or even if she came home last night. I don’t even remember falling asleep. Just tossing and ‘turning’ in my poopy diaper as much as my bonds would allow. Trying to get comfortable inside the crib and trying not to think of who my wife was with and what she might be doing. She must have slipped something into that bottle, otherwise I would have stayed up to see just exactly how long she was out that night.

    Was she with Charles? If so, did he tell her about me? That he’s been keeping me as his personal suck slut and all of this started because I was looking at sissy porn in my work computer?

    I didn’t even have the courage to ask her as she untied me from the crib and led me to the floor to change my poopy diaper.

    Her makeup was a little smeared. She hadn’t bothered removing it after last night. She still looked gorgeous as ever, albeit a little tired. 

    She fed me breakfast with a tiny baby spoon. Mushy bananas. Then helped me get my suit on over my diaper. Tapping my butt and giving me a kiss...on the cheek. “Have a good day at work, baby!” she said, waving goodbye.


    I couldn’t focus on anything at work. Just moving numbers from one column to another while blankly staring at the screen. I couldn’t stop thinking about my wife being tangled up with another man. Images of him fucking her, the same way he fucked me. The same way she had me fuck her with that big, black, fake dick.

    I was almost eager to get to Charles’ daily blowjob. I thought about what I might say to him. How I would try to stand up to him. Confront him. Like a real man would do.

    At 11:00 I made my way to his office. Garnering the usual looks from coworkers along the way.

    At his door. I took a deep breath. Summoning all my courage. Prepared to stand up for myself. When I knocked, the door was opened by a woman. Not Stephanie the secretary.

    But my wife.

    “Oh! Hi honey!” she smiled.

    All of my courage left me like a deflated balloon. My jaw hit the floor.

    “Wh-what are you doing here?” I asked. Was her hair messed up? Or was it just my imagination?

    “Well I...” she leaned in to whisper this next part “I came to change your diaper and feed you some lunch. Then I ran into Charles and we got to talking!”

    I studied her for a good while. After all these years with my wife, I’d never had to catch her in a lie. She was always so honest with me. But that was before she had to keep me in diapers and be around bigger, more attractive men.

    I could see Charles smirking in the background. Not giving anything away either. “Amy and I were just discussing a possible opening at the company. Assuming you get promoted to corporate that is...”

    I looked back and forth from Amy and Charles several times. Both smiling softly.

    “W-well w-what if I refuse the position at corporate?” I said with as much resolve as I could muster.

    Charles clasped his hands and stared at me for a long while. “Hmmm...perhaps we should discuss it at another time?” he smiled, “How about over Dinner? Tonight. Your place.”

    To be continued....

    Please be patient for the next coming Chapters. This is not my job. I don’t get paid for this (other than from those of you who generously donate). It’s just something I do on the side. I have a life that is more important sometimes. Thank you for your understanding and support. It means a lot that some of you are so passionate about this silly story. Stay horny and stay diapered :)

    Click Here to Read Part 13

    The Boss’ Baby Part 11 - The Replacement

    Part 1

    Part 10

    “Hi honey!” Amy said as she came through the door to the house, carrying several large shopping bags in each hand.

    I smiled at her and turned back to the dishes. I was supposed to have them done before she got back. But she didn’t seem to care, she was still smiling which meant she must have had a good shopping spree.

    She placed the bags down on the table and came up behind me, kissing me on the cheek before pulling the back of my diaper out with a finger and peeking inside. Wearing nothing but a diaper already made me feel like a baby, but it was nothing compared to how casually she would check my diaper for poo like I was a toddler.

    When she was satisfied that my rear end was clean, she reached around to peek into the front end. Not to check if it was wet from piss. She didn’t seem to care much about that. “Diapers are too expensive for me to change you every time you make a pee pee” she’d say. Though she didn’t seem to care about money much when she went out shopping...

    No, what she checked the front part of my diaper for was my tiny cock cage inside. To see if i’d gone back on our deal by tampering with the equipment. We had agreed i’d go a month without cumming so as to increase our chances of conceiving a baby. It had only been two weeks of me not cumming and being treated like a baby instead and I was already wanting to quit.

    “Awww! Your wittle winky seems to be leaking constantly through that cage! Good thing you’re in that diaper!” She giggled. Patting me on the bum and heading back to her shopping bags.

    “Wait ‘til you see what I got! I found the cutest stuff for my wittle baby!!” She bounced with joy as she pulled out a bib that said ‘Mommy’s Wittle Baby!” She had been starting to feed me mushy peas and carrots and other pureed baby food lately. I was not the biggest fan, and would spit and dribble some of it out. That seemed to egg her on. She was happy to shovel it back in my mouth and coo at me while she loaded up another spoonful just to say “here cummss the wittle airpwane!!”

    Her baby talk was getting excessive. It started out slow at first, but after several days of changing my diapers she was really starting to get into the “Mommy” role. And every step seemed to be more and more humiliating.

    “Oh and i got the most adorable wittle outfits for you!” She giggled. The first one was a large romper, which I thought would have been difficult to find in my size, but apparently it was a new fashion trend for full-grown males to wear them now. Kids these days...

    “And i know you tried to say you don’t like dressing like a girl but...come on! Look how pretty these are!” She held up two frilly dresses. One was yellow with little duckies on it, and the other was pastel pink.

    “I...i...” i didn’t know what to say.

    “Oh don’t try to argue! You know i’ve always wanted a baby girl! And i got this for when you’re doing your chores around the house!” She held up a sexy french maid outfit. But it was way too big for her.

    “Honey...isn’t this all a little...”

    “I’m not done!” She said. Still grinning from ear to ear as she dug into another bag. She pulled out a medium sized buttplug. About the same size as the one Charles made me buy for myself when he first put me in panties.

    “You used love it when i put my finger in your ass during sex. So figured you would like this up your butt all the time!” She laughed as she fiddled with the packaging.

    “Honey what has gotten into you?! I —“ but she cut me off as she pushed me over the counter so I was bent over.

    “Hush! And relax! Deep breath!” She said, pulling my diaper down enough to expose my ass cheeks. She spread them open and I felt the plug press against my hole.

    This was all happening so fast. She used to be so sweet and innocent. But ever since the Christmas Party she started getting so much more dominant.

    Once she had the plug worked all the way into my ass she pulled the diaper back up and patted my bum. “There we go! Now it’s time to test it...”

    “Test what?” I asked. But my question was answered immediately as I felt the plug start to buzz inside my hole. I turned to see she was holding a small wireless remote control. She smiled wickedly, clicking a button and causing the steady vibration to change to a strong, rhythmic pulsing of varying intensity. It made my legs quiver. She laughed hysterically.

    “One last thing...” she said, going back to her bags.

    She pulled out a large box. My jaw dropped when i saw what it was:

    A big, black, strapon dildo.


    “Wh-what is that for...?” I asked. Playing dumb.

    “It’s for you sweetheart!” She gleamed.

    “B-but honey...” i stammered, “i may be okay with a finger in my ass, and maybe a plug, but I don’t think I can handle...” it shamed me to think that I was lying. I knew perfectly well I could handle that big black dick in my ass. I’d been handling Charles’ for the last few weeks, and this strapon wasn’t even as big as his...

    “Oh! Hahaha!” She covered her mouth with the box as she giggled. “Sweetie no! I’m not gonna fuck you with it! You’re going to fuck me with it!!”

    It wasn’t what I was expecting, and I was genuinely confused. “What? Why?!”

    “Well just because you can’t cum for a whole month doesn’t mean I shouldn’t be able to!!” She scoffed, opening up the box and pulling out the 7 inch black dildo and straps.

    “B-but I...”

    “Oh come on!! Don’t you want to please me...?” She smirked. As if there was more to that sentence. She placed the cock right over the diaper where my own caged cock was and started wrapping the straps around the crinkly padding.

    “B-but honey...will you at least change my diaper first? I’m...i’m all wet....” i begged pathetically.

    “Awww the wittle baby is all wet??” She laughed as she cinched the straps and pulled them tight around my soggy diaper. “So am i.” She said.


    I looked down at the rubber dick dangling from legs. It was so much bigger than mine that usually hung there. Amy’s face appeared as she dropped to her knees in front of it.

    “Does this turn you on?” She teased as she took the head of the rubber cock in her mouth. Her eyes rolled back as she moaned with dick filling her throat. I whimpered as she slobbered all over it. Wishing desparately that it was my own cock in her mouth.

    “I want you to FUCK me over the counter” she said. Emphasizing the word ‘fuck’ as if that wasn’t what I was doing all the times we made love in our 12 years of marriage.

    I wanted to cry. To object. But she was already pulling down her panties and hiking up her skirt as she bent over the counter. I could see her pussy was already glistening with wetness. She hadn’t gotten that excited for my dick in a long time, but was practically dripping for this fake one.

    I took the rubber cock in my hand, not used to having to hold so much length and girth, and aimed it into her pussy.

    “Ohhhh myyy godddd!!” She moaned as it entered her. After about 4 inches i expected to stop, as that was all i could usually bury into her with my own dick, but there was still 3 more inches to go. I didn’t think she’d able to take it all, that i’d hit some internal organs or something. But she handled it easily and hungrily until the cock was buried into her up to the fake balls.

    “Ohhh yesss!” She said as i started pumping the cock in and out of her. My wet diaper crinkling with each thrust.

    I felt the plug start to pulse harder in my asshole. “Harder!” She barked. And i did the best i could do pound her with my quivering legs.

    “Yes! YES! Oh my GOD! YESSS!!” She groaned. She never made these sounds when we had sex. “Oh Char—Tom!! Yess!!”

    What the fuck was CharTom? I thought. But didn’t dwell on it long as she started rocking back and forth and slamming her perfect ass against my “cock” like a bitch in heat.

    My balls were aching. My real cock was pressing painfully inside its cage.

    “I’m gonna cummm!” She moaned. Usually I would have cum by now. Rarely did she ever beat me to the punch. But neither of us had to worry about this fake dick cumming too fast.

    Her legs quaked and trembled. I could see the waves of pleasure coursing through her body. It struck me then how rare a sight it was for me to see her orgasm. It hadn’t happened often in our marriage. In fact, i’d probably made men orgasm more in the past 2 weeks than i made her orgasm in 12 years. It was a disheartening thought as she moaned and groaned on the counter.

    “Don’t stop!” She commanded between breaths. “Keep going!” She flicked the button on the controller and my plug started pulsing painfuly again.

    I fucked her for 30 more minutes. Giving her 3 more orgasms while I thought about how nice it would be if I could just have one.


    “So your wife seemed nice,” Charles said as I sucked on his cock.

    My stomach dropped, but I tried not to make it obvious as I slurped on his balls.

    “I want her number.” He said flatly.

    “What?!” I said. Forgetting my sissy voice he’d made me use. My saliva still dripping from the head of his dick.

    “You heard me.” He said firmly. “I want her number. I’m going to fuck her.”

    My head was spinning. I’d be lying if I said I didn’t see something like this coming. I could see the spark between them. The way her eyes lit up when she saw him. How wet she got from me fucking her with a big black dick. She wanted this. And now he did too.

    I didn’t know what to say. I tried to be strong. I wanted to be strong. He had already taken so much from me. My masculinity, my orgasms, he wasn’t going to take my wife too.

    “No...” i finally said. I wanted it to sound powerful, but it came out squeaky and pathetic instead.

    “What?!” He growled. His face flashing anger.

    “N-no!” I repeated. Shakier this time.

    He yanked me by the wrist so hard that i hit my head on the desk as he jerked me out from underneath it. Twisting my arm behind me painfully as he forced me over the top of the desk. Hard. My head spinning in pain as he ripped my diaper off. Jamming his slimy cock into my ass with such force it felt like i was being torn open.

    “You. Will. Give. Me. Her. Number!” He barked. Emphasizing each word with a hard thrust while I squealed in pain. “And. You. Will. Beg. Me. To. Fuck. Her!!”

    I cried. I begged. I pleaded.

    “Please...not my wife!” I groaned. It was the last shred of dignity I had left.

    “Your wife deserves better than a pathetic sissy baby like you!” He said. And deep down I knew it was true. The way he was fucking me right now on the desk was the way she’d wanted to be fucked yesterday on the counter. She didn’t want my dick that was small and came much too quickly. She wanted his.

    “Ok...” i sniffled, “ok...i’ll give you her number...”

    And i did.

    “Good gurl. Now beg me to fuck her.” He said, still maintaining a hard and fast rhythm.

    “P...p-please...” i couldn’t find the words. My mind was blank. My ass was being split open. “”

    I burst into tears.

    But he wasn’t done.

    “Louder.” He said.

    I sniffled and whimpered. “Please don’t make me say it again...”

    “Are you forgetting?!” He growled, “you belong to ME now! So BEG you fucking slut! And use your sissy gurl voice!”

    My tears and snot were forming a puddle on his desk. I sniffled and took a deep breath.

    “PLEASE! SIR! Will you fuck my wife?!” I shouted in my high pitched voice.

    I felt his dick erupt inside of me. Filling me with his warm seed.

    When I looked back he had the biggest smile on his face. “If you say so!”


    Click Here To Read Part 12.

    The Boss’ Baby Part 10 - Office Christmas Party

    Part 1

    Part 2

    Part 3

    Part 4

    Part 5

    Part 6

    Part 7

    Part 8

    Part 9

    It wasn’t held in our office building. The company spared no expense as they rented out the ground floor and grand hall of an expensive hotel. Everyone I worked with was congregated around a giant Christmas tree in the middle of the ballroom.

    My wife Amy looked positively radiant. She always looked beautful, but tonight she was wearing a tight black sequin dress that sparkled in the glow of the tree. Her blonde hair done up perfectly in an elaborate bun. I was wearing one of my best, most expensive suits. It was a perfect night. Other than the diaper i had underneath.

    “What’s wrong?” She asked, noticing my discomfort. “I told you you didn’t have to wear that thing.” She nodded towards my pants where my diaper crinkled underneath.

    But i do have to wear it... I thought. Boss’ orders...

    Speaking of, Charles approached, smiling. He wasn’t married, so he didn’t have an official guest. But Stephanie was right next to him. She also looked glamorous. Her raven black hair framed her face perfectly, and her curves in her red dress made my cock twitch inside my cage.

    “Hi! You must be Amy!” Stephanie said in that cheery voice girls use when they first meet each other. There was a hint of a wicked smile as she shook Amy’s hand. “Have you met Charles? He’s our Boss. Tom has definitely been sucking up to him quite well.”

    They all laughed. I cringed. There were so many unspoken things going on that both parties knew about. Like the fact that i’d been blowing Charles. That he suggested (more like ordered) i be put in diapers, and that Stephanie was the one changing me during the day and was the other holder of the key to my cage. Conversely, Amy knew I was in a diaper and cage right now too, but didn’t know Charles and Stephanie were the ultimate masterminds behind it.

    “Yes, Tom has spent a lot of time bent over a desk, hard at work!” Charles chuckled. “There are talks of a promotion in the future!”

    Amy gleamed. “Well that sure would be wonderful! I’m sure he’s learned a lot from a...powerful man like you Charles!” There was admiration in her eyes as she looked the chiseled man up and down. I was sure I saw a glint of something else in her eyes too.

    “I’m going to grab something from the bar...” i said to Amy, trying to make things less uncomfortable. “Do you want anything?”

    But it was Charles that answered, “I’ll take a Scotch on the rocks.” He said pointedly. “Stephanie will have a Cranberry Vodka and...Amy?”

    “Champagne.” Amy said, a little taken aback by Charles forwardness, but not seeming to mind very much at all.

    I knew better than to argue, so off I went. Crinkling to the bar while Charles said something that made both the girls laugh.

    “Scotch on the rocks, Cranberry Vodka, and two glasses of Champagne please.” I said to the bartender. Suddenly there was a hand on my shoulder.

    “Tommy boy! There you are!”

    I turned around to see George, the creepy old guy from corporate, smiling with that predatory grin of his. He was with another older white gentlemen.

    “Uh...hi George...” i stammered, praying the drinks would arrive sooner so I could leave.

    “I was just telling Mike here that we need you moving up to corporate!” He chuckled as be slipped a card into my hand. “In fact...why don’t you make your way up to the 5th floor for a...debriefing. Within the next 5 minutes should suffice. Unless you...wouldn’t like to have a job at all” he looked down at me menacingly as he sipped his drink. I knew from how uncomfortable Charles was around him that he meant business.

    “Yes sir...” i said as the drinks were placed on the bar. George and the man laughed as they turned back to the party. Before grabbing the drinks i glanced at the card George slipped me. It looked like a business card, with gold writing stenciled:

    Admit One. Floor 5.

    But what room was I supposed to go to? I guess i’d figure that out soon enough. I headed back to the group where Charles, Amy and Stephanie were still laughing.

    “Honey can I talk to you?” I asked, pulling her aside.

    “What is it sweetheart?” She asked, sensing my tone. “Do you...need a diaper change?” She whispered the last part. Smirking a tiny bit.

    “Wha? No I...” was caught off gaurd by that “i...i need to go upstairs...there’s...some guys from corporate...”

    “Oh!” She gasped, as if understanding, “maybe this is about that promotion!” She clapped her hands in glee.

    I sighed. “Yea...maybe...”

    “Don’t say ‘maybe’! You got this! Give it your all! I’m sure they’ll be begging to have you!!” She kissed me on the cheek. “Now go! I’ll fine down here!” And she turned back to Charles a little too eagerly.


    There was a bellhop on the elevator.

    “Where to?” He said.

    “5th floor please.”

    He stopped. “Do you have...”

    “Oh...yes....” i said, handing him the card. My hand shaking. He examined it. Looked me up and down. Smirked. And nodded. Putting a key into the control board and turning it so that the button to floor 5 would activate.

    I trembled as the elevator rode smoothly upward. There was a ding, and the doors opened.

    The entire floor was filled with people. But unlike the party downstairs, it wasn’t filled with people in tuxes and dresses. It was filled with people in lingerie, latex, or very little clothing at all.

    The bellhop shoved me out of the elevator forcefully, i turned around to try to get back in, but was grabbed by two big bouncers.

    They held me still while the door closed. Once it was gone they released me. “You gonna strip or we gonna have to do this the hard way?” One of the big bouncers asked.

    I trembled as I removed my very expensive tux and stripped all the way down to just my diaper. I would have felt out of place, but not 10 feet away from me were two sissies naked on their knees with their mouths open and a sign around their necks that said “Garbage”. I watched as a man in a suit walked over and spooned the remainder of his plate into the sissy’s mouth.

    “Drinks?” Said a voice. I turned to see a beautiful cocktail waitress smiling at me holding a try of beverages. I hesitantly grabbed a glass of champagne and downed it immediately, then grabbed another. She smiled. But then i looked down at her lingerie and noticed a cock cage like mine dangling between her legs. “Word of advise?” The sissy waitress said. “You’re in a diaper, so you might want to crawl around. Unless you wanna end up like them over there...”

    She pointed to the far wall where 3 sissies were bound spread eagle to 3 big X-like structures. Men and women took turns taking a bullwhip to all of their backsides. Laughing as they squealed in pain.

    I needed no further prompting. I gulped down my third glass of champagne and dropped to my hands and knees. Crawling my way through the crowd of kinky people. Not even sure where I was headed.

    I made my way through a sea of legs. Not sure if the ones in heels belonged to actual females or sissies like me. I felt my diapered bum being patted and crinkled by creepy strangers as I walked by.

    I decided to follow the music, which led me to a stage with a bunch of lounge chairs surrounding it. A bunch of older men sat back as sissies serviced their wrinkly cocks with their mouths. On stage there was a sissy spinning around on a pole. They chuckled as they sipped their whiskeys and jizzed in the sissies’ mouths.

    At another stage was a man with a microphone. He sounded like an auctioneer. Rambling on about the three “pigs” he had on stage. “This one squeals like a wittle piggy as soon you put anything up his ass.” He said, smacking one of the fat sissies that was on all fours. He had a rubber pig snout on his nose.

    There were men and (real?) women in front of the stage, holding up signs to signal for their bids.

    I crawled away as fast as I could.

    In the next area there was a group crowded around a sissy strapped to a saw horse. Two machines on opposite sides of her, pumping giant dildos thut spun like a drill in and out of both her holes.

    “Looks like she’s close to cumming boys! Place your bets! Over/under 30 seconds! 10 to 1 odds!” Hollered the man standing next to her.

    In another corner was 6 sissies on their knees facing a wall. They bobbed their heads back and forth on what i presumed to be dildos. There were large meters above each one that looked like big thermometers. And every time the sissy went forward on the dildo they pushed a button with their nose, moving the little stick figure higher.

    “Looks like #4 is in the lead, but #5 is coming in hot!” Called the announcer, “oh #3 is making a comeback, but will he make it in time?” The crowd around was hooting and hollering and holding up wads of cash. “Ohhh! And it looks like 5 is the winner!”

    There were cheers and jeers as the sissy with number 5 around his neck was turned around and his arm raised. He was sobbing for some reason. It wasn’t until the announcer used a key around his neck to unlock his chastity cage that I realized they were tears of joy.

    It was like some kind of sissy circus. Everywhere I looked someone was getting fucked or sucked, and there always seemed to be money involved.

    “There you are, Baby!” Someone said. I glanced up to see another one of the Corporate white men I met before. I think his name was Bruce? “You’re needed in the side stage!”

    He pulled a collar and leash out. Wrapping it around my neck unnecessarily and led me over to a small platform where people were already gathered. I trembled as I crawled up the ramp where there was another sissy waiting. This one was in much more elaborate attire than me. His large pink bonnett, bib, mittens, and booties were a stark contrast compared to me in just a diaper.

    Bruce removed the leash attached to the collar once me and the sissy were facing each other on all fours. He picked up a microphone “good evening ladies and gentlemen!” His voice boomed. “If you’ll head to the side stage, you can see two sissy babies attempt to take on: The Pacifier!” He said this last bit with exaggerated flair. There was already a crowd forming around the stage.

    Soon a large object was tossed in the middle of us. It was a large double ended dildo. In the midpoint of the dildo was a plastic ring shaped like the plastic part of a pacifier.

    “Each end of the dildo will be placed in the sissies’ mouths.” Bruce explained, and as he did an assistant lifted the 2 foot dildo, forcefully putting the tip into each of our mouths. “In the center is a plastic ring. The sissies will try to move the plastic ring as far as they can to the opponent’s side using only their mouth and deepthroat skills. They have 5 minutes! Place your bets!”

    The crowd erupted into calls. “150 on the pink one!”

    “100 on A! It’s the sneaky ones that are kinkiest!”

    “B’s got it! I’ll put 500 on it! Pansies that wear pink know how to take it!”

    I noticed there was a large tag hanging from the other sissy’s neck that read “B”. Mine must say “A”

    “Begin!” Shouted Bruce, and a timer next to the stage started ticking down from 5:00 minutes.

    The sissy opposite me immediately began pushing forward, causing the other end dildo to push against my throat. I still hadn’t learned to control my gag reflex. I choked, but the sissy kept pushing. Swallowing the other end of the cock until his nose was able to push the ring. He only moved it an inch or two, but it was easy to see it was past the red line that marked the center of the dildo. I tried to take the dick down my throat and push it back, but my gagging kept me from getting even close to it.

    There was cheering from the crowd as the other sissy closed his eyes and leaned forward, forcing the cock even further down his throat, past the red mark, and nudging the plastic ring even further.

    I glanced at the clock, 2 minutes left. Now that the ring was closer to me it was easier to reach. I nudged it forward, but it wasn’t enough to move it to the halfway point signified by the red line.

    1 minute.

    I drew in breath around the rubber cock filling my mouth and tickling my throat, then exhaled. Wincing as i forced the cock as far as I could down my throat. Encouraging shouts from the crowd helped. I relaxed my throat and blinked back tears as I nudged the ring forward, past the red line and over. I was proud of myself, and the cheers from the crowd made me feel even better about my dicksucking skills.

    But there was still time left. 20 seconds. I was too tired to push any further. Instead it was the other sissy’s turn to swallow the dick and send it back over to my side. Just past the red line as time expired. “Baby B is the winner!” Bruce called. The crowd bellowed with a mix of happy and angry shouts. As if we were nothing more than a roulette wheel to them.

    Me and the sissy both relaxed and let the dildo fall from our mouths onto the stage. Breathing heavily.

    “Now...we have time for one more event...what should we make them do?” Bruce beckoned to the crowd.

    “Ass to Ass!” One of them shouted. And the rest of them agreed. “Yea!! Ass to ass!!” “Ass to ass! Ass to ass!!!” The crowd chanted in unison.

    Two assistants came and turned us both around. Untaping our diapers and lubing up our assholes.

    “Awww! Looks like the last event got our wittle babies excited!” Bruce cooed. I looked down at my urine soaked diaper and noticed a string of precum making its way down from my caged cock. The other sissy’s was doing the same.

    “First to cum completely from fucking their ass, wins!” The crowd cheered and started placing their bets. The assistants held each end of the dildo to our lubed up holes. “BEGIN!”

    I tried to force myself backward on the cock. Feeling it bend as the other sissy did the same. With help of the assistant, we managed to work it into each of our holes. Crawling backwards to snake more of it in.

    This was as much of a team event as it was solo. As we both had to work in unison and build up a rhythm to work the dick in and out of our assholes. Money showered us from all directions as the crowd hooted and hollered. Soon both of our ass cheeks were clapping against each other as we bounced back and forth.

    The rubbery cock actually felt good inside me. Stimulating my prostate and giving me the biggest sense of pleasure i’d had in weeks. My aching cock pressing inside its cage. Desperate for relief. But i could hear the sissy moaning behind me. He was getting close.

    I tried to hurry. But a cheer from the crowd told me i’d already lost. I glanced back to see the sissy convulsing behind me. Goo shooting through his cage and down into his diaper. “And B wins again!” The announcer hollered. Some onlookers yelled at me for losing. “Pathetic!” “Fucking faggot!” “Learn how to take a dick!”

    I sobbed pathetically as the assistant put my diaper back on.


    “That was quite the meeting” Amy said in the car on the way home.

    “Yea...sorry about that i...i wish i didn’t have to stay so long...” i mumbled. I was back in my suit with my diaper underneath. But my hole was abused and my throat was sore.

    “Well did it go well at least?” She asked.

    “Not really...” i said. “But i did get a nice bonus!” I pulled out the wad of cash that was thrown at me on stage. “Almost $2,000!”

    “Wow! Maybe we can do that trip to Cabo we’ve always talked about!” She gleamed.

    “Yea...maybe...” i said, shifting in my diaper.

    “What’s wrong?” She asked. “Is your diapy wet?” She giggled, reaching over to squeeze my crotch. Making my balls ache even more.

    “’s just...i’m sorry i had to leave you for that long...” i said.

    “Oh...that’s okay...” she smirked, “Charles kept me company.” She had a weird look in her eyes. One that would haunt me for the rest of the weekend.


    Click Here To Read Part 11

    The Boss’ Baby Part 9 - The ‘ole Switch-a-poo!

    Part 1

    Part 2

    Part 3

    Part 4

    Part 5

    Part 6

    Part 7

    Part 8 

    You know how when someone tells you not to think about to think about something, that something immediately becomes all you can think about? Well imagine that thing you’re not supposed to think about is cumming, but you have a constant reminder between your legs in the form of a cage that keeps you from doing just that.

    After only a week in chastity, I felt like i was in a constant haze. Not being able to sleep because i wanted to cum so bad, and spending my days only making others cum. Wishing it was me.

    That being said, it was only my boss Charles I was having to pleasure this week. I guess Dave’s date with Stephanie went well, because he hadn’t called me into his office to blow him at all ever since.

    Speaking of Stephanie, I needed to find her. I just made a very stinky, dirty mess, in my diaper and needed her to change me.

    I prayed no one could smell me as I walked past their cubicles towards Stephanie’s desk at the front of the office. I’d be lying if I said I wasn’t aware the of the whispers and rumors surrounding me in the office. I think people were slowly becoming aware that something my constant squirming and the crinkly noises coming from under my clothes.

    I put that to the back of my mind as I approached Steph’s desk. But she wasn’t there. Maybe she was in Charles’ office?

    I headed that way and knocked on the door. I could hear whimpering from inside. I saw someone peek through the blinds, assess it was me, and then the door opened.

    I was not prepared for what I saw.

    Dave was standing with his pants around his ankles. A soaking wet diaper around his waist. Bawling like a wittle baby. Dancing back and forth uncomfortably.

    “I-i-ii’mm s-s-s-sssoo s-ss-sssorryyyy!!” He cried.

    Stephanie was standing next to him, scolding him.

    “Youre gonna be sorry after i’m done with you!” She growled menacingly. “Did you really think I would fuck you after just one date?! Is that why you forced yourself on me?! Is that what you tried shoving this into me?!” She grabbed the front of his wet diaper and squeezed.

    Dave squealed much harder than would be expected from someone just grabbing a diapered crotch. He was crying and whimpering pathetically. It was a stark contrast from how we was last week when I was under his desk sucking his dick.

    She kneed him hard in the crotch. He keeled over and fell to his knees. It was at this moment i noticed something green and leafy poking out the sides of his diaper.

    “You’re fucking SCUM!” She barked, standing over him “but if you want to cum so bad, go ahead and do it. Right here. Right now. On the floor!”

    “No!! NO!!! Please! Please no! I’ll do anything!! I’m sorry!! PLEASE!!” Dave begged. His face was panic stricken. I didn’t understand why he was so terrified of having to hump his diaper and cum, i’d do anything to do that right now after spending a week in chastity.

    Stephanie ignored him. Walking behind him and digging her heel into his back until he was forced down flat onto the floor. With every rustle of his diaper Dave let out a squeal of pain.

    “Cum bitch! It’ll be the last time you get to for a while!” Stephanie sniggered.

    It was weird being on the viewing-end of someone else humping the floor in a diaper. All i could do was stand there awkwardly while Stephanie verbally degraded him and Charles chuckled from his desk. Eventually he seemed to notice me and gave a slight nod to his crotch.

    I knew what that meant. I waddled over and knelt between my Boss’s legs. Unzipping his fly and pulling out his already throbbing cock. It was usually never this hard this quick, apparently he was enjoying Dave and Stephanie’s show.

    All i could hear was Dave’s whining, crying, and pleading mixed with the rustling of his diaper as I slurped on Charles’ cock. Dave really sounded like quite the baby, I didn’t understand what the big deal was.

    But i soon would.

    Even through Dave’s crying I could tell the sound of him about to cum, and with that, Charles’ own sounds came as his cock swelled in my mouth. His dick pumped jizz down my throat as i imagine Dave’s spurting a load in his diaper simultaneously.

    “Changey time boys!” Stephanie said in her cheery Mommy voice. I wiped my mouth as I climbed out from under Charles’ desk and laid down next to Dave. He was glistening with sweat and tears.

    “Oof Tommy!” Stephanie sneered, “you’re quite the wittle stinker aren’t you?!” I flushed in shame as she opened the tabs of my diaper, exposing the full load of poo mixed with my tiny caged cock. She cleaned me up, using the key on a chain around her neck to unlock my chastity device. I knew better than to get excited or expect anything. But that didn’t stop my freed cock from getting instantly hard. Once she had it clean she flicked it on the head painfully, making it retreat into a limp noodle before caging it back up again.

    Instead of powdering me and putting me in a new diaper, she simply left me naked and caged as she shifted her attention to Dave.

    “Did you like the addition i made to your diapy, wittle Davey?” She giggled as she opened his up. Finally I got to see what was inside that was making him so miserable. But it was just a bunch of leaves from some sort of plant.

    But i couldn’t help but notice how red and inflamed Dave’s cock was. He must have had some sort of allergy to the plant.

    “Unfortunately I left fresh diapers in the car...” Stephanie said unconvincingly “guess you two babies will just have to wear each others diapurrs!!”

    It was obvious this was planned all along as she pulled my still unwrapped poopy diaper over to Dave. “Lift up Davey! Time for the ‘ole switchapoo!!” She giggled as Dave whimpered. Squishing down on my soiled diaper and cringing as she wrapped the cold mush around him and taped it up tight.

    “Your turn Tommy! Maybe you won’t be as whiney about the nettles as Davey was!”

    As i lowered myself onto the sticky pile of leaves, I immediately understood Dave’s discomfort. It felt like I was being stung by a thousand tiny bees all over my ass and taint. I whimpered, pleading with her to reconsider as she lifted the front of the leaf-filled diaper.

    “Please nooo” i begged. But she just laughed. Pulling it up and folding it over. It was the first time I was thankful to be wearing a cage, as it was less skin to come in contact with that devilish plant. My balls felt like they were on fire as she taped it tight around me. I wanted to scream. But I didn’t want the rest of the office—or the rest of the block—to hear.

    “You will both report back to me for changes and spankies before you leave work today” she said matter of factly. Unfortunately that was still 6 hours away...


    “Oh my goodness!” My wife Amy said as she opened up my diaper. “Wooks wike the wittle baby has quite the diapy rash!!”

    The leaves were gone, but the inflammation from the nettles remained. Turns out having thousands of tiny little needles poking your pubic area all day can make you quite red down there. The spankings that Dave and I had to administer to each other while Charles and Stephanie watched made my ass even more blistered.

    “Awww!! There there wittle baby!!” Amy cooed. She was really starting to embrace her motherly role. “Mommy knows just what to do to make it alllll better!”

    She reached for a tube of lotion or cream and applied it to her hands.

    The coolness of the cream and her touch made me feel instantly better. In fact, a little too much better...

    “Awww! What’s wrong sweetie?! Is the wittle baby getting excited?!” She giggled. Noticing my cock pressing inside my tiny prison as she applied the cream to my balls.

    I nodded and whimpered.

    “Awww!! Do you want me to use this...?!” She asked as she fished the chain holding the key to my cage from between her perfect, perky tits. Dangling it tauntingly at me.

    Again I nodded. “Please!! It’s been soo long...” i sounded so pathetic. But i didn’t care. I just wanted to cum.

    She bit her bottom lip and considered. “Hmmm...nope!” She said. “We had a deal. One month of you not cumming! It’s only been a week!”

    “B-b-but honey!! I really want to—mmmphh!“ but before I could say any more she had plopped a pacifier into my mouth.

    “Shhh! That’s enough fussing out of you wittle baby! Now let’s get your diapy on before you leak all over the bed!”


    Click here to Read Part 10

    The Boss’ Baby Part 8 - Busy Day

    Part 1

    Part 2

    Part 3

    Part 4

    Part 5

    Part 6

    Part 7

    It was a busy day.

    My morning started with Dave from IT emailing me to come down to his office. I knew exactly what that meant.

    “What did she say?” He asked as I bobbed my head on his cock.

    “I have to do her a favor first,” i said, using my saliva as lube to stroke him while I talked, “but that should be done today”

    I was referring to the chastity cage Stephanie wanted me to wear in order to get her to go on a date with Dave. The plan was for my wife Amy and I to go pick one up after work.

    “Did she say anything about me?” He asked while i sucked his balls.

    “That she hopes you don’t have a small dick…” I said.

    “Well…” he smiled, grabbing me by the back of the head and shoving his cock back down my throat, “at least you know that isn’t true.”


    “What’d she say?” Stephanie asked as she applied my makeup in Charles’ office. “About the diapers?”

    “She took it…surprisingly well.” I said, trying to get used to the weight of mascara on my eye lashes.

    “Of course she did,” She laughed as she pulled my hair into two tiny pigtails, “she’s probably thought a loser with a baby dick like yours should have been diapered a long time ago. Do you have the picture?”

    I opened my phone and showed Stephanie the picture of Amy smiling as she changed my first poopy diaper. “She was happy to do it…she just didn’t want it to end up on the internet.”

    “Well as long as you’re obedient it won’t have to. Now send it to me for my records.” She said.

    Just then, Charles walked into the office, followed by the older white man from corporate, George. Again I expected someone to look taken aback when they saw me on my knees dressed like a girl. But George didn’t bat an eye. Just flashed a toothy grin.

    “Ahh, so this is your rising star,” George said as he circled around me. Inspecting me like I was a piece of meat at a livestock show.

    I knelt there trembling in my lingerie and diaper. Not daring to move. “Needs bigger tits” he said, groping my chest. “Open” He said, shoving a fat grubby finger into mouth, swirling it around. “Teeth are a little big, but those can be removed eventually. Can we take this off?” He said, referring to my diaper.

    Stephanie hurriedly rushed forward and removed the tabs to my wet diaper. Allowing it to fall to the floor.

    George flashed a creepy smile. “Ohhh now there’s a nice piece of ass!” He said, squeezing my cheeks and making me yelp as he smacked my backside. “Why is this not caged?” He asked, pinching the head of my cock painfully.

    It was the first time I’d seen my Boss Charles gulp uncomfortably. “He uh…”

    “He will be getting one today, sir” Stephanie interjected from the corner.

    “Excellent. It’s very important to keep these faggots on edge. Makes them more eager and obedient” said George, smacking my ass again.

    Charles’ cleared his throat “He’s quite the little slut, George.” He said, circling me as well. “Not the best at sucking dick yet, but what he lacks in talent he makes up for in enthusiasm.” I glanced over to see Stephanie stifling a snigger.

    “Good…good…” said George, “well i want a quarterly report on his progress before we make the decision to move him up to corporate.”

    “Of course, sir.” said Charles. It was weird seeing a big dominant black man like Charles seem almost intimidated by a frail, creepy old man like George.

    “Very good.” Said George, removing his tie. “Now…let’s see how well the little bitch can take a dick.”

    I spent the next hour bent over Charles’ desk getting spitroasted.

    Charles took me from behind while I slurped on George’s wrinkly old penis. Stephanie standing to the side with a clipboard writing down notes as George called them out.

    “Needs to learn to use his tongue more”, George would say, “Suction on the way up, not down. Drool more. And watch those fucking teeth!”

    Then they would switch. Charles moving to my front and George to my back. George’s 5-inch dick was nothing compared to Charles’ 8.5, so I actually was okay with the switch. Even though Charles did everything he could to stuff his all the way down my throat.

    “There you go! Take it you fucking faggot!” George moaned. Pulling on his tie that he had used to bind my wrists while he spanked my ass. Stephanie giggling in the corner.

    Charles grabbed my own tie dangling from my neck and lifted it up. Wrapping it around his hand. Jerking it. Using it like I leash to yank me up and down his cock.

    I could hear George grunting from behind as he pounded me. I was beginning to learn the universal sound of a man orgasming first hand. His dick pulsed and throbbed inside my rectum and then erupted. The warmth filling my insides.

    “Not done yet, Charles?” George asked as he pulled out and wiped his own brow.

    Charles said nothing, but I glanced up to see beads of sweat forming on his face. He abandoned the tie, grabbed me by both of my tiny pigtails, and started thrusting.

    It is incredibly difficult to breathe when your esophagus is getting invaded by a big black monster. My nose was leaking many different fluids and mixing with my drool as it rained on to the floor. Charles is going to punish me for that later. I thought.

    “On her face.” George commanded, apparently understanding the universal sound Charles was making.

    I could see the disdain flash across Charles’ face at the mess this would make on his carpet. But he said nothing. Just pulled the python from my throat and stroked.

    I decided it would be a good idea to hold my mouth open and try to catch as much as I could to keep it off the carpet. The big black veiny cock was staring me in the face as I waited. Slack jawed.

    I thought about all those girls in poorly edited porn videos that had to just sit there with their mouth open and wait an uncomfortably long time for the giant cock to pump jizz in their mouth.

    I didn’t have to wait much longer. The first shot sent a line down from my forehead to my chin. The next one hit my mouth. I could tell Charles was painting my face with his cum in a way that would appease George, but also not get too much on his carpet.

    The three shots that hit my cheeks and eyes next made me feel like a glazed donut.

    I cracked open a cum covered eye to see George chuckling as he grabbed his briefcase and the door and left.

    “Get it all in your mouth and not on my floor, Tommy.” Charles said, his voice a little deeper than usual. Like he was trying to reassert his dominance over me now that George was gone.

    After using my finger to squeegee the cum into my mouth, i made to stand up from the desk. But Charles used one hand to force me back down.

    “Ah ah ahhh!” He tisked. “Aren’t we forgetting something?”

    Then he channeled his frustrations into my spankings.


    “Try to enjoy it,” Stephanie said as she sat on the floor next to me, playing on her phone. “This might be the last time you get to cum for a LONG time.”

    I was on the floor of the women’s restroom again. Humping away in my wet and poopy diaper.

    “Jesus, you stink.” Stephanie scoffed, wrinkling her nose “what did you have for lunch today?!”

    Dave’s cum. I thought. I had spent my lunch break under his desk again. He was insatiable. It was my 3rd time blowing him that day. “I’m not gay.” He reiterated several times, “i’m just really excited for my date with Stephanie.” He’d peruse her social media pages on his computer while I sucked him off.

    I wonder if she’s texting him. I thought as i squished inside the disgusting mess of my diaper. She didn’t seem interested in me. I tried to enjoy my last chance to cum before being put in chastity. But all I could think about was how my life was spinning out of control as I spurted a weak load into my diaper.

    “Changey time!” Steph said. Laughing.


    “And you’re sure you want to do this…?” My wife Amy asked incredulously. Holding up the small plastic cage that would be a prison for the foreseeable future.

    We had just gotten back from the Sex Shop. The same one where I bought the lingerie and buttplug. Of course it had to be the same clerk to check us out too. I hoped and prayed that she wouldn’t say anything to my wife just then, but instead she just looked at the chastity cage, at me, my wife, then back at me, and just sort of nodded in a way that said “Yep. That makes sense…”

    Now as Amy sat on our bed between my legs holding the tiny device, I contemplated telling her everything. My Boss is making me be his personal slut, my Secretary is the one that’s keeping me in diapers, and the guy who has a crush on her got 4 blowjobs from me today.

    “Y-yes…” i said, visibly worried. I wanted to sound more confident and less terrified, but i failed miserably. “Me not cumming will give us a better chance to conceive a baby”

    She narrowed her eyes at me and I could sense how stupid it all sounded. But instead of arguing she just shrugged. Taking the ring and securing it around my balls and wiener. Then sliding the plastic tube around my shriveled member.

    “Say bye bye to cumming for a whole month!” She said as she slid the tiny padlock between the ring and the tube.

    And with one tiny *click* the lock —and my fate— were sealed.

    Click Here to Read Part 9

    The Boss’ Baby Part 7 - Terms and Conditions

    Part 1

    Part 2

    Part 3

    Part 4

    Part 5

    Part 6

    “So what’d she say?” Stephanie asked as she applied mascara and eye shadow to my eyes in Charles’ office.

    “Who?” I asked. Playing dumb.

    “Your wife. About your diapers...”

    “Oh...uh...yea that” i stammered, as if i forgot “she said I was a freak. That this was going to be a stain on our marriage. But she was willing to work with me if that’s what I wanted.”

    Stephanie stopped applying the blush to my face to stare at me inquisitively. I quivered under her gaze.

    “You’re lying.” She said.

    “What? No! I-i...what are you doing?” I asked.

    “I’m sending your wife the video of you humping your wittle pissy Pampers yesterday!” She said, tapping through her phone. “Her number was in your emergency contact file...”

    “No wait!” I exclaimed. Stephanie stopped and looked up, smirking.

    “I’ll...i’ll tell her tonight...” i said. Hanging my head.

    “Tell her what exactly?” She asked.

    “That...that I wear diapers I need to tell her about Charles too?”

    She thought on this for a second. “ At least, not unless Charles orders you to. For now, you will tell her about the diapers. And you will get a picture of her changing you as proof.”

    I nodded as she had me purse my lips to apply bright red lipstick.

    “Oh and just so you know...” she said offhandedly “Charles likes it if you play with his balls...”


    I left Charles’ office an hour and a half later with cum leaking into my diaper from my butthole.

    Stephanie had stood witness as Charles came in, complemented her on getting my makeup good enough for me to be “fuckable”. Laughed as Charles bounced me on his knee with my plug in while he told me what a pretty baby gurl I was. Then helped administer the spankings after Charles’ made me suck him til he was hard enough to fuck my ass.

    On my walk of shame back to my cubicle, I ran into Dave from IT. Who was standing there menacingly with his arms crossed.

    “Hi Tom,” he said. “Can I see you in my office please?”

    I spent the long walk to the IT wing running through a thousand different scenarios in my head. Dave was the one who had shown Charles the sissy porn on my work computer. Dave knew what I’d been looking at. Was he going to use that information to blackmail me too?

    Dave’s office was secluded at the far end of the hallway.

    “So,” i said, once we had both sat down. Trying to sound casual, “what’s this all about.”

    Dave crossed his hands and stared at me for a good while. He was a tall, kind of scrawny white guy who probably laughs in the face of all the people who called him a ‘nerd’ in highschool that he’s now making three times the salary of.

    I shifted in my seat from the silence. Hoping he didn’t hear the diaper crinkle under my suit.

    “What the hell does she see in you?” He finally said.

    “My wife? I...i’m not sure to be honest...” i chuckled awkwardly.

    “Not your wife dumbass, Stephanie!” He said, his face flushing with rage.

    Dave apparently saw from my face that I was extremely confused. So he clarified, “I saw the two of you come out of the bathroom together yesterday. And then again this morning. Both times I heard your girly-sounding moans. So how long have you been fucking her?!”

    I struggled for words. How did I explain to this guy no you’ve got it all wrong. You see, she was actually in there changing my pissy diapers! And the moaning you heard was the sound of me humping said diapers!

    “You don’t understand...” i finally said, “it’’s complicated...”

    “Does she know you’re a sissy?” He said. Playing his card. “Does she know you look at this shit on the internet?!”

    He clicked through his computer a few times and turned the monitor to show me a video of a sissy getting pounded from behind by a big black man. I decided not to tell him that was pretty much me about 15 minutes ago in Charles’ office.

    “Stephanie and I are not together, Dave. We’re not fucking. We’re just...friends. She helps me with my makeup and gives me tips and stuff. That’s what we were doing in the girl’s bathroom...” i said. Not exactly lying.

    He narrowed his eyes. “Then what about the moaning i heard?”

    “That was me practicing my girly voice for when day...get fucked in the ass. She said it needs to sound pathetic. Apparently guys like that...” i said, hanging my head convincingly.

    Again Dave stared at me for a long while, but apparently he bought it. “ definitely did sound pathetic. And your lips are still stained, like you had on makeup earlier, so it makes sense.” He said. Turning to his computer. “I’ve got a lot of dirt on you, so if you don’t want this to get leaked to the office or to your wife, you’re going to need to do something for me.”

    “What...?” I asked. Tired of this stupid porn being held over my head.

    “Get me a date with Stephanie.” Dave said. It wasn’t exactly what I was expecting, but it was better than having to suck his dick or something.

    “I...i’m not sure I can do that...” i said.

    “I thought you guys were friends?” Dave asked, eyebrow crooked.

    “We...we are but...”

    “You have until the end of this week before I leak your search history. I still haven’t been able to figure out why Charles’ hasn’t fired you yet. He seems to even be favoring you now with how much time you spend in his office...”

    You have no idea...i thought.

    “I’ll see what I can do...” i said. Taking my cue to leave. I was almost at the door when Dave stood up and stopped me.

    “Not so fast.” He said, coming closer than social norms would deem comfortable. “Before you go...let’s see if you can suck dick as well as some of the sissies in those videos you watch...”


    “He wants to what?” Stephanie asked. Changing my diaper for the 2nd time that day.

    “Go on a date with you.” I repeated. Trying not to get excited as she wiped the piss off my shriveling dick.

    “I don’t know...” she said “he’s kind of weird. And why would he get you to ask for him?”

    “He thinks we’re friends....actually, he thinks we’re fucking.”

    She roared with laughter. “Me?? Fucking you?! With this tiny dick?!!” She pinched the tip of my two inch flaccid penis. I blushed in shame. “His dick is probably as small as yours anyway...” she shrugged.

    Actually it’s about 6.5 inches...and his cum tastes a little sweeter than Charles’ i thought.

    “Will you just go out with him please?” I begged. I really didn’t need more people at the office knowing about my porn habits.

    She pondered as she powdered me. “I tell you what: if you wear a chastity device in addition to your diapers. I’ll go on the date with Dave.”

    My stomach dropped. Unfortunately with all the sissy porn i’ve seen, i knew exactly what a chastity device was, and exactly how much i didn’t want to wear one.

    “ wife doesn’t even know I wear diapers yet!”

    “Then I guess you’ll have a lot to break to her tonight...”


    “We need to talk.” My wife Amy said when i walked through the door.

    It was weird, because it was exactly what I planned on saying.

    “About what?” I asked.

    “About how weird you’ve been acting lately.” She said.

    Oh god. I thought. She knows.

    “Do you not find me attractive any more?” She asked, almost tearing up.

    “What? No, Honey! You’re beautiful! Gorgeous! I just...”

    “Well then what is it? Huh? Why can’t I get this dick of yours hard for me anymore?” She said it as she squeezed my crotch. The diaper i had on underneath crinkled. I was frozen. Recollection shined across her face. “Are-are you wearing a...?”

    “Honey I can explain...” i stammered.

    “A diaper?!” She finished. Pulling my pants down and exposing the big fluffy diaper with the letters “B A B Y” written across it.

    “It’s a long story, now don’t be mad but...”

    “Why would i be mad?” She said, smiling. It was not the reaction I expected. “You know how much I want a baby and you obviously feel guilty that you can’t give me one. So you thought dressing like one and wearing a diaper would make me feel better! That’s honestly really sweet! Weird....but sweet!” She laughed. Kissing me.

    “That’s...that’s exactly right!” I said, going along with it.

    “Is that why you’ve been wearing my panties too?” She asked. “Because you knew how much I’ve been wanting a girl?”

    “I...what? You knew?!”

    “Of course I knew!” She laughed. “You think i didn’t notice the way you’ve been wadding them up and stuffing them in panty drawer? I just wish you would have bought your’re staining mine and stretching them out...”

    I couldn’t believe how well she was taking all of this. “I’m glad you’re not mad. But there’s one more thing i’ve been thinking about: if i’m going to get you a real baby, i need to build up as much sperm as possible until you’re ovulating again.”

    She pondered this for a while. “Okay so no sex until then. But that means you can’t touch yourself until then either!” She laughed at that, knowing how perposterous that sounds. “You don’t have that much self-control.”

    “Actually...there are ways to keep me from cumming until you need me to...” i said, dreading it.

    “And how is that?” She asked.

    “Have you ever heard of this thing called a ‘chastity device’?”

    To be continued

    Click here to read Part 8

    The Boss’ Baby Part 6 - Using the Restroom

    Part 1

    Part 2

    Part 3

    Part 4

    Part 5

    “On the floor.” She commanded. Her voice was almost as stern as Charles’.

    “But this is the women’s restroom!” I pleaded. “What if someone comes in??”

    “Then you better hope your wittle baby dick isn’t out when they do. Lucky for you, not very many women work here. Now...” she snapped her fingers and pointed down. “Pants off and get on the floor, wittle baby!”

    I realized I was just wasting time by arguing. So I unfastened my belt and pulled my slacks down. Leaving only my panties with a very wet diaper underneath.

    I climbed down onto the floor and laid on my back.

    “Na uh! On your tummy wittle baby!” She said.

    “ are you gonna change my diaper if i’m facedown?” I asked, befuddled.

    She giggled. “Oh i’m not gonna change it yet! First I want you to do what you always do when you come into these restrooms. I want you to make a #3!!”

    It took me a while to figure out what she meant. But when I finally realized she intended for me to masturbate, I was still confused. “Okay...well how am I supposed to do that facedown?”

    She patted my face like I was a silly child. Then cooed “awww!! You know....” then she mimicked a humping motion.

    I blushed. Everything about this was humiliating. But I wanted this all to be over with. So I turned over on my stomach onto the cold bathroom floor.

    “I suggest you hurry...” she said, “someone could come in any minute!”

    I sighed. Knowing she was right. I allowed the weight in my waist to press into floor. Forcing the cold, soggy diaper into my crotch. It felt disgusting. I took one last glance over at her kneeling next to me. Smiling. Then closed my eyes and tried to concentrate.

    The cold tile mixed with my cold diaper made my penis shriveled inside. But a little wiggling (and crinkling) got it in a position where I was able to get at least a little sensation. The plug in my butt making me feel full. I cringed at the crinkling sound as I began rubbing the soggy diaper against the floor.

    “I want to hear you moan.” Stephanie said. “Come on baby gurl! Let me hear you!”

    I was trying to forget she was there but her constant encouragement made it blatantly obvious that I was humping a pissy diaper on the floor of a restroom in front of a beautiful woman, moaning like a pathetic pansy.

    “Suck your thumb, wittle baby! Pretend it’s Charles’ cock you’re sucking on!” She giggled.

    I did, and to my dismay my cock finally started hardening, but it did make it easier to get sensation. I wiggled it back and forth, side to side. Crinkling like crazy.

    “Tell me when you’re cumming, loser!!” She ordered.

    My cock was swelling, my balls pulsing, my butthole puckering and clenching painfully around the plug. “I’m cumming Mommy!! Aghh! I’m cumming!!”

    I convulsed on the floor, moaning and whimpering, as my warm sticky goo filled my diaper. I collapsed on the tile. Breathing heavily.

    When i finally opened my eyes I looked up to see Stephanie had her phone out. Videoing.

    “Awww!! Did the wittle baby make a goo goo in her diapy?!” She cooed, camera still rolling.

    My face flushed. “Turn that off!” I squeaked pathetically.

    “Don’t!” She said, dodging my feeble attempt to grasp her phone. “Disobey me and I send this to everyone in the office! Do I make myself clear?”

    I wanted to cry from humiliation. I sniffled and nodded.

    “Good. Now use your baby voice to tell me what you just did, and beg me for a change!” She said, aiming the camera directly at me.

    I wiped a tear from my eye and squinted into the camera. “I...i made a goo goo in my diapy....will you please change m-my pissy...sticky...diapy Mommy?”

    She laughed and stopped the recording. “Alright. On your back, pansy!”

    I lay back in shame as she maneuvered between my legs.

    “Does your wife know?” She asked as she pulled the panties down.

    “Know what?” I asked as she undid the tabs of the diaper.

    “That you’ve been wearing her panties the last two weeks. That you’ve been sucking your Boss’ dick and are his little plaything.” She said as if it were obvious.

    “ least...i don’t think so...” i said meekly.

    “Well she obviously can’t be very satisfied with this...” she teased, nodding at my sticky dick that had shrunken to less than an inch long when she opened the diaper.

    I wanted to argue. To say she seems happy with my dick. That she tells me size doesn’t matter. But I don’t even believe it myself.

    “No girl likes a guy to be this small” she said. As if reading my mind. “Deep down she wants someone to fuck her. Hard. With a BIG dick. Does it bother you that you’ll never be able to give her that?”

    I didn’t know what to say. So I just laid there while she wiped me down with a baby wipe. I couldn’t even appreciate this beautiful woman touching my dick, if only to clean my wet, sticky messes off of it.

    When she was done, I expected her to just pull my panties back up. But instead she pulled out another diaper.

    “What are you doing?” I asked, flabbergasted. “It’s almost 5 o’clock. I’ll be going home soon.”

    “And you’ll be going home in a diaper.” She said matter-of-factly.

    “B-but my wife...” i babbled feebly.

    “I think it’s time your wife knew what a sissy baby loser you are.” She said, laying the diaper down. “Raise up.”

    I contemplated how and if i could possibly explain all of this to Amy as Stephanie powdered me frivolously.

    Once I was taped up and had my clothes back on. Stephanie gave me two diapers “for your wife to change you at home” that I stuffed inside my shirt.

    When we exited the bathroom together Dave from IT was just outside on his way to the men’s room. He stopped, looked back at both of us inquisitively. Then hurried into the men’s room.


    My commute home was actually made a little better by the diaper. I didn’t have to hold my piss. Just let it fill the diaper while I thought about ways to break it to Amy.

    When I walked through the door. She was upstairs, probably on the Peloton.

    I seized the opportunity to rush to the bathroom, rip off the lingerie and diaper, hide the other ones under the sink, and head to the bedroom.

    “Hey.” Amy said. She was already on the bed waiting for me in a sexy piece of lingerie, not unlike the set I wore today for Charles. We have similar taste. “I’m still ovulating.” She winked.

    Thus was another night of her attempting to get my dick that had already came twice that day (once from being fucked in the ass) to get hard. Trying to explain that the baby powder on my cock was due to chafage. And finally working my semi-limp noodle inside of her just for me to cum faster than her.

    “No, i’m not disappointed.” Amy said after it was over. Even though her voice was dripping with it. “As long as you give me a baby i’ll be fine.”

    I fell asleep thinking about the irony of those words.

    To be continued

    Click Here to Read Part 7

    The Boss’ Baby Part 5 - Diaper Time

    Part 1

    Part 2

    Part 3

    Part 4

    “So...what did you do to earn this?” The secretary Stephanie asked. Holding the very large diaper in her hand as she stared down at me over her black-framed glasses like a stern librarian.

    “I...i...” i stammered. I came myself from our Boss fucking me in the ass. That doesn’t sound fucking pathetic, right?! “I...i don’t know...” I finally said.

    “Hmm..well i’ve never seen someone earn these so fast! I mean it’s only been what...two weeks?”

    My jaw dropped. “ knew?!” I asked. Horrified.

    “Of course I knew! I’m his secretary! You don’t think i’ve noticed you spending an hour or two in his office every day? You don’t think I hear your fucking pathetic wittle whining? You don’t think I notice you wiping away tears and clutching your sore bum every time you leave his office? Honestly with how much of a baby you sound I’m surprised he hasn’t put you in these sooner...”

    Her words stung. After everything i’d been through I didn’t expect to be degraded by a woman I considered a friend at work. A woman I was sexually attracted to.

    “Awww! Don’t cwy wittle baby! Let’s get your diapy on shall we?” She cooed like a mother to a child.

    She took me by the arm, my hands still tied behind my back, and led me like an officer would a handcuffed prisoner over to the desk.

    “Awww! Looks like somewon had a wittle accident on the floor!” She said, noticing the stain from the puddle I made. “That’s why the wittle baby needs diapurrs!! Charles is very anal about his floors!”

    She pushed me on the desk. For the first time, I was on my back on the desk instead of bent over it. Instead of getting fucked or spanked, I was about to get diapered by a beautiful woman.

    “You said you’ve never seen someone ‘earn these this fast before’” i said, trying to make conversation as she unfurled the diaper. “Does that mean there were...others?”

    She smirked. Switching her ‘Mommy voice’ off for a second. “Yes. Three. One was embezzling money, the other was similar to you. Pathetic guy. Masturbated at work all the time, looked at porn, etc. Raise up!”

    I lifted up my bum as she slid the diaper underneath me. “What happened to them?” I asked.

    “They...moved up the corporate ladder...” she said. Unsnapping the straps to my garters.

    “But that’s only said there were three?” I said as she pulled down my panties. Charles’ jizz was still leaking from my hole.

    “Awww! That’s what happened!” She said, switching back to her Mommy voice, “somewon must have got a wittle too excited while the Boss was pounding their wittle pansy pussy huh?”

    I flushed. Turning beat red. But i tried to ignore it. “Don’t change the subject. Who was the third?”

    Her expression turned stoic. “Me.” She said

    “You? Are...are you —“

    “A sissy? Heavens no. I was just the first. The stereotypical secretary that wanted to get ahead by giving her boss head...” her eyes were a bit misty. “Until I found a way to earn my boss’ approval without spending my days bent over a desk. Instead, i found other prospects that he might eventually find...desirable.”

    It hit me like a ton of bricks. “You.” I said, “you were the one that called me about a job offer. You were the one that looked over my resumé. Had me give you every email address i’ve ever owned”

    She nodded. “And i used that to find out about your dirty little habits. Interesting Tumblr you have by the way...”

    I couldn’t believe it. It was like a trap. A spider’s web I was caught in.

    “And i don’t ever want to go back spending my lunch break on my knees under his desk. Better your mouth/ass than mine!” She said, picking up the buttplug on the table and pressing it to my bum. It slid in pretty easily now that my hole was gaping and cummy. She switched back to her Mommy voice. “That’s why we’re going to get this wittle diapurr on you before Charles gets back and punishes both our asses for insubordination!”

    And with that she pulled the diaper over my still oozing cock. Taping it up tightly.


    I got very little done at my desk the rest of the day. The plug was uncomfortable to sit on, and my constant squirming was making my diaper crinkle so loudly under my suit that I was sure the cubicles next to me were able to hear me.

    It was also difficult because — being in a diaper — i was prohibited from going to the any place other than my diaper of course.

    “I’ve seen how many trips you make to the bathroom after He’s done with you” Stephanie had said “no one has to pee that many times. So you can just use your diaper to do those #1s , 2’s and 3’s I know you love making!”

    I’d been holding my piss for the last 3 hours. I glanced at the clock. 3:15. I really didn’t think i’d be able to make it another hour and 45 minutes. My bladder was close to bursting. I glanced back and forth as if anyone would understand what I was about to do.

    I heaved a huge sigh and allowed myself to relax. It felt weird to tell my brain “it’s okay, you have a diaper on. Go ahead” and it took me a second to rewire the 28 years of potty training i’d been doing.

    My warm, wet diaper immediately made my face hot. I just pissed myself. Like a fucking baby. It did nothing for my uncomfortable situation.

    After an hour in my wet diaper. I had relieved myself two more times. I couldn’t take the feeling of the soggy mess anymore. So I did what I’d been instructed to do.

    I waddled through the office over to Stephanie’s desk. Praying no one noticed me crinkling and waddling.

    Stephanie looked up from her work and smiled. Removing her glasses and tossing back her hair. “Well well can I help you wittle baby?” She said at normal volume.

    “Shhh!” I said. Looking around. Hoping no one heard.

    She giggled at my paranoia.

    “What is it baby? What’s wrong? Tell Mommy...” she cooed. Resting her chin on both her hands in amusement.

    “You know what I need...” i whispered “now can we just get this over with?”

    “What do you need honey? Tell mommy.” It was obvious she wasn’t going to let me off that easily.

    “I...i wet my diaper. Now can we just please—“

    “You did what baby? Sorry. I couldn’t hear you...”

    I cursed inwardly. Looking around to make sure there was as few people around as possible.

    I cleared my throat, and spoke as loudly as my pride would allow.

    “I made pee pee mommy...” i said, knowing if I did the stupid baby voice she was more likely to cut me some slack “will you p-please change my...diapy?”

    It was the biggest smile I had ever seen her give.

    “Of course sweetie” she said, scooping up a bag from behind her desk. Her heels clanking as she strode past me. “Come along little one!”

    But she wasn’t headed to Charles’ office. She was headed towards the company restroom.

    To be continued

    Click here to read Part 6

    The Boss’ Baby Part 4 - The Mess

    Part 1

    Part 2

    Part 3

    “Good morning, Tom!”

    “Good morning, Dave!” I said as we passed each other. Dave was the IT guy that Charles used to find the incriminating porn on my work computer that got me into this mess.

    It was the first time i’d seen Dave since the incident. I was terrified of how he’d look at me after seeing some of the things i’d searched for. But he didn’t seem to show any indication of caring and he didn’t seem to notice that I was waddling past him with a large plug stuck up my bum.

    I tried to seem normal as I walked up to Charles’ office and knocked on the door.

    “He took an early lunch” a beautiful voice said behind me. I turned to see the stunning Secretary Stephanie wearing a gorgeous red dress smiling at me through lips painted with matching lipstick. Her raven-black hair fell to her shoulders, and her eyes seemed to twinkle behind her black horned-rimmed glasses. “He’ll be back shortly if you’d like to wait over there...”

    She pointed me to a set of couches stationed in front of her desk. Her heels clanked as she walked behind and sat down at her own desk directly across from it.

    “Have a seat!” She reiterated when i hesitated.

    I nodded and slowly waddled over to the couch, sitting down gingerly so as to keep the plug from pressing painfully further into my asshole. The cushions of the seat didn’t help, and instead pressed the plug deeper than it’d been all day. I cringed and tried to get comfortable. Which wasn’t easy with the nylon teddy and lingerie i also had on underneath my suit.

    Stephanie eyed me suspiciously, but didn’t seem to pay me much more than a glance as she returned to her work on the computer.

    After about 30 minutes of discomfort in Stephanie’s presence. My Boss Charles’ finally stepped through the door laughing with 3 other men. “...and then I said ‘you’re fired!’ and he practically started crying!!” Said one of the older white men. They all laughed in unison, but Charles’ deep baritone voice was the most prominent.

    “Tommy boy! Sorry to keep you waiting! Come here and meet the execs at the corporate office!” 

    My stomach probably would have dropped out of my ass if it weren’t for the plug. My mouth was agape as I slowly scooted off the couch, wincing at the wiggling of my plug. I tried to keep a straight face as I waddled over to the small crowd of businessmen.

    “Tom, meet George, Stan, and Bruce!” he said, introducing me as if I were one of his pals. I shook each of the wrinkly white men’s hands awkwardly. “Tom here is one of our rising stars” Charles said, enunciating the last words in a strange way. 

    A sense of understanding seemed to wash over the men. One of them smirked at me wickedly. “Oh I bet he’s quite the...asset!” George said. His eyes wandering.

    “He certainly is.” said Charles “he spends quite a bit of time bent over a desk. Handling anything I throw at him! Don’t you Tom?”

    He nudged me. “Y-yes. Yes sir I do...”

    The men all laughed as if it were some joke I didn’t get.

    “Well I’m sure we’ll see you around, Tom! Perhaps at the annual Christmas Party?” said Bruce, still sporting that wicked grin.

    “You sure will!” Charles said, answering for me. “Now if you’ll excuse us, gentlemen. Tom and I have to attend to.”


    “Please fuck my wittle slut hole, Daddy!” i cried as I bent over His desk. Pulling my burning red cheeks apart, exposing the hilt of the pink plug in my bum, dressed only in the lacy black bustier around my waist, with straps that went down to garters and fishnet stockings. 


    “You can do better.” He said firmly. “Make it sound girlier!”

    Each slap of his hand across my already fiery ass not only sent waves of pain up my spine, but caused my butthole to clench around the plug painfully.

    “Unphh! Daddy, PLEASE fuck my wittle butthole!” I squealed in a higher octave than before. I tried to make it sound convincing. I knew what he would do if I didn’t. But inside I knew there was no way my virgin asshole could handle his massive meat. “I want to feel you inside me, pounding my insides like the wittle sissy whore I am!”

    “That’s better.” He said. “But you need to learn to control your little clitty sissy!” I squeaked as he flicked the back of my balls. It was the closest he’d been to touching my privates in the two weeks since I’d been his personal panty princess. “Your little baby dick is leaking precum all over my freshly renovated rug!” He barked.

    "I’m sorry Daddy!” I exclaimed. “I’m not meaning to!” And I really wasn’t. It pained me how excited all of this made me. My 4 inch dick was rock hard and angled painfully downwards. Hopefully my panties around my waist would catch most of my leakage.

    “Now...where were we...” he said. I felt the plug being pulled. As as hard and painful as it was to get in this morning, it was even more painful on it’s way out. I gasped and gave a very girly sounding whimper as it finally plopped it’s way out of my poor little hole.

    He placed the plug on the desk next to me.Then placed the head of his hard dick to my now slightly gaping butthole.

    “Now you’re going to have to relax sissy. This is going to hurt...a lot...”

    And with that he pressed into my hole. Just the head invading me was enough to make squeal, flailing my arms and knocking over papers as I reached for the edge of the desk. 

    “Ow! OW! Daddy! It’s too big! I...I don’t think I can handle it! Maybe if you let me suck it it’ll go in easier!” I made to stand up but he slammed me back down on the desk. Hard. Tears started welling up as he pressed his dick onward, I felt like I was being split in half. Panic set in.

    “I can’t! It’s too big! Please! PLEASE!” I flailed my arms again. Desperate for anything to keep him from invading me. But he grabbed both my arms and pinned them down behind me. 

    “Hold. Still.” He grunted. I felt something being wrapped around my wrists. Probably my neck tie.

    He spit down my crack and continued to work it in despite my pleas. I tugged futilely at my bonds as he pressed onward.

    By the time it was all the way in, my tears had made a puddle on his desk. I sobbed pitifully as he took me from behind. This was not how I pictured my first anal experience to go. The sissy’s in porn made it look so easy and pleasurable.

    After about 10 minutes of him using me, my hole finally started to relax and accommodate the massive python snaking it’s way in and out of my insides.

    All of a sudden he started hitting a certain spot inside me. To my surprise, it sent waves of pleasure throughout my entire body.

    “Oh.” I said. Sniffling.

    “You like that you little slut?” He chuckled.

    I didn’t know what to say. I just hoped he would hit that spot again. And he did. Again and again. Soon my blubbering cries turned to moans of pleasure.

    I had to be certain not to make too much noise. But I couldn’t help it. It was a pleasure I had never experienced before.

    “Don’t you fucking cum on my floor, sissy!” He growled. Picking up the pace now. But with each thrust he was hitting harder and harder on that special spot.


    I don’t know what happened. This huge wave of pleasure enveloped me like never before. My legs quaked. My body convulsed. And suddenly I could feel warm, sticky goo running down my legs and onto the floor.

    “GOD. FUCKING. DAMNIT!” He yelled. I could feel his anger with every thrust as he grabbed my bound wrists and started pounding me relentlessly.

    “I. TOLD. YOU. NOT. TO...CUM!!” as soon as he said the word I could feel his dick pulsing inside me. I could feel each spurt of hot goo being pumped into me. His breathing was heavy as his cock withdrew from my ass and he plopped down on the chair.

    “Look at the mess you made you fucking whore!” I’d never seen him angry like that. 

    With my hands still tied behind my back, I lifted myself up and looked down at the huge puddle of my own jizz staining his carpet.

    “Get down there and lick that up.” He barked.

    I’ve never dropped to my knees so fast. His rage was terrifying. I started lapping up my mess like a scolded puppy.

    After slurping as much of my semen as I could off the floor, I looked back up at him. Hoping his anger had subsided. It hadn’t.

    He pressed the buzzer of the intercom. “Stephanie, will you bring me those D.P.R. forms please?” There was a short pause for a couple seconds. Finally, followed by “right away, sir.”

    Oh shit. Stephanie was coming. She could be here any minute and would see me in my slutty lingerie.

    I tried to crawl underneath his desk and hide. But His legs stopped me. “Na uh, I think you’ve had enough of MY dick today you little slut”

    I started scrambling. I had to get my clothes on before she came in and saw me like this. But that’s easier said than done when your hands are tied behind your back.

    I didn’t even get my panties back up around my waist by the time she walked in.

    Her eyes immediately met mine. I expected her face to be horrified as I stood before her. Frozen in my ridiculous lingerie. But she barely spared me a once over before turning to her boss as if nothing were awry.

    “I have the um...forms you asked for, sir.” She said. Clutching a clipboard to her chest.

    “Excellent.” Charles said, standing up. Unapologetic about his dick swinging between his legs while he pulled his pants up. “If you’ll administer them to Tom here, I will be back shortly.”

    And with that, he stormed out of his office without another word.

    She smirked and turned to me as soon as he left. Pulling the big white form out from behind her clipboard.

    “So...what did you do to earn this?” She asked. Smiling wickedly as she held up the big white form.

    But at second glance I realized it wasn’t a form. It was a very large diaper.

    To be continued

    Part 5

    The Boss’ Baby Part 3 - Inferior

    Part 1

    Part 2

    There are a few things I wished I could get rid of that day:

    The first was the taste of my Boss’ cum lingering in my mouth.

    The second was the look on the girl’s face at the Sex Store when I asked her if I could try on a piece of lingerie.

    The third was the sound of laughter she tried to stifle when the realization hit her.

    The fourth was my feeling of shame when I put the lingerie and a large pink buttplug on the counter for her to ring up.

    The fifth was the condescending tone she had when she asked me if I needed anything else. “We have dildos and makeup if that’s something you’d be...interested in...” she said with a slight smirk.


    “Hi honey!” My wife said as I walked through the door.

    “Uh, hi!” I said. I had hoped she’d be upstairs working out when I got home. I also hoped she didn’t notice the shakiness in my voice, or the taste of Charles’ cum on my lips as she gave me a kiss.

    “How was work?” She asked “anything exciting?”

    Oh you know, just gave my Boss a blowjob under his desk while I was wearing your panties... I thought.

    “Same old same old...” i said. Fetching a glass of water to try to get the taste of cum out of my mouth.

    “What’s in the bags?” She asked.

    I froze. Clutching the unmarked plastic containing the buttplug and lingerie.

    “Oh it’s ummm...nothing...just one of your presents!” I stammered.

    “Getting shopping done early this year huh?” She said smiling. My wife Amy was so beautiful. Her long blond hair reflecting the light seemed to make her glow. Some—actually many—would say she was out of my league. ‘She’s only marrying you for the money’ they’d say. I’d always hoped that wasn’t true but deep down I knew it probably was.

    “So...” she said, grabbing me by the hips and turning me around to face her. She leaned in close, kissed my neck, and whispered in my ear “i’m ovulating.” She said with a wink.

    Amy desperately wanted a baby. We’d been trying for almost a year now with no success. She’d refused to get tested because she didn’t want to face the fact that something might be wrong with her body. I didn’t have the heart to tell her that the problem was most likely not her, it was me.

    “Do you want to bend me over this counter and have your way with me?” She asked, biting her bottom lip as her hand moved to my crotch “does that get you hard?”

    She grabbed my bulge which I couldn’t help but realize was significantly smaller than Charles’.

    My dick was also soft. Which was to be expected as I had masturbated 3 times that day in the office bathroom after sucking Charles’ dick.

    “Awww!” She cooed. “Wittle Tommy doesn’t wanna come out to play yet huh?” She said smirking as she lifted my shirt and made to go into my pants. “Does he need a hand?”

    “NO!” I exclaimed. Louder than I meant to. I couldn’t have her reaching into my pants and discovering I had her panties on underneath. “I-i need a minute to uh...i...i have to use the restroom first.”

    I bolted upstairs. Leaving her bewildered.

    After I’d stashed the lingerie and plug and changed out of my clothes and her panties, I came back downstairs.

    Amy was already completely naked. Her perfect, perky breasts bouncing in front of her like headlights as the rays reflected onffher glistening smooth, tan skin. Her hourglass shape was always what drew me to her. It was like she was photoshopped.

    “Does this get you hard big boy?” She asked. On any other day it would. But my dick was still a limp noodle in my pants when she reached for it.

    Her face was slightly hurt when she realized it, but she shook it off quickly with a smile. “Sorry...” i said. Feeling pathetic and shameful. Any other guy would have a big throbbing cock right now.

    “It’s okay,” she cooed “i know how to give it the attention it wants...”

    She undid my pants and dropped them to the floor along with my (male) underwear. She took my limp, 1-inch dick between her two fingers and started stroking. I hated that she only needed two fingers, when it took two of my hands to stroke Charles’ giant cock.

    “ about my mouth?” She said, licking her lips as she pushed me back onto a chair, dropped to her knees ,and took my tiny member in her lips.

    Her mouth felt so good around my cock, but still it was unattentive. I tried to will it to get hard but it just didn’t seem to work.

    Then I was reminded of the blowjob I gave today. On my knees to a guy sitting in a chair like Amy was doing now. I now knew exactly what it felt and tasted like to have a dick in your mouth. And suddenly, my cock started to harden.

    “Theeerrre we goo!!” She said, after getting it to it’s full 4-inches of potential.

    “Now fuck me over the counter!” She said. Taking my hand and practically puppeteering me to push her over it.

    Her large, plump buttocks was staring up at me. Her back arched as she eagerly awaited for me to fill her up with my cock.

    When i pressed it in, it slid in easily. I couldn’t help but feel like someone else would probably be able to fill her the way she wanted to be filled better than i could. But I put that thought aside as her moans started.

    “Ohh yes, Tom! Yes! YES! Harder! HARDER! I’m going to cum I just need it a little—oh...”

    But before she could say anymore I had already came.

    “I’m sorry...” i said shamefully “were you able to..?”

    “No...” she said, hiding her disappointed face as she put her clothes back on. “But that’s okay! Maybe this could be the one!” She said hopefully.

    “Yea...maybe...” i said. Knowing it was extremely unlikely that my loser load could produce a baby.

    To be continued

    Click here to read Part 4

    The Boss’ Baby Part 2 - The (Blow)Job

    For Part 1 Click Here

    I could feel His hard cock between my asscheeks as I gave Him a lap dance in His desk chair. I’d be lying if I said I hadn’t noticed the bulge in His pants over the past week.

    Every day He had me come into his office, strip for Him, and show him the pair of panties i’d worn for Him that day. And every day I went back to my desk with a sore, red bottom from the spanking He’d just given me. Not because I misbehaved in particular. He said the spankings were to remind me of my place. I learned to muffle my squeals as I was bent over His desk to receive an ever increasing amount of swats from His big black hands.

    Every day I would sneak off to the bathroom afterwards, pull down my pants and panties, and rub one out inside the stall. My post orgasm was immediately met with shame as I emptied my load into the toilet. “What would my wife think?” I thought, “if she knew I was stealing her panties to wear them to work and model them for my big, dominant boss? What would she think if she knew how much I was starting to actually look forward to it?”

    “Mmm that’s it, slut!” He said. Smacking my ass softly as I ground it against the crotch of his pants. I could feel His dick stiffening between my crack. I wore the pink thong today. I’m not entirely sure why.

    “You’ve been a good gurl lately” He mused. I was still trying to get used to Him calling me a ‘gurl’.

    “Thank you Daddy” I said, getting used to calling Him ‘Daddy’ like he told me to. I swayed my hips and arched my back to the music coming from His computer.

    “I think it’s time we took things to the next level” He said.

    I stopped dancing momentarily. Wondering what that meant. He smacked me hard on the ass to let me know to continue.

    “Unh! W-what do you mean Daddy...?” I asked. Trying to use the feminine voice He’d been encouraging me to use.

    He grabbed my wrist. Bring it down to His leg. Then He slowly moved it up to his crotch. His bulge. I could feel it pulsing.

    “ want me to...” i stammered, panic setting in as I looked back at Him.

    He had a big smile on his face and nodded. “That’s right baby gurl. It’s time for you to truly earn the nickname of ‘slut’! Now get on your knees.”

    I knelt down between his legs under his desk. My heart beating out of my chest. “I...i dunno Daddy...” my voice shaking. “I...i don’t think i’m ready...i...i’ve never...”

    “Ahhh but there’s a first time for everything isn’t there?” He said, unzipping his fly.

    “Now be a good little gurl and take it out for me.” He said.

    I hesitated for quite a while. Not knowing what to do. Should I run? Would he fire me? Would he tell my wife?


    I was snapped out of my reverie by His hand across my face.

    “Now!” He barked.

    I sniffled as I reached with my shaking hands between the gap in His zipper. I probed around for His member. Not that it was hard to find. I could barely wrap my fingers around it as I snaked it out of the hole in his pants. It was the first time i’d ever touched a penis other than my own. And mine was NOTHING compared to the size of His. 8 inches of thick, dark meat stood straight up at me. But as intimidating as it was, I couldn’t take my eyes off of it.

    “Suck it.” He commanded. As if I didn’t already know what He wanted from me. I was just trying to summon the courage. I knew what was in store for me if I didn’t.

    Finally, I took a deep breath, and leaned forward.

    It seemed to get bigger as it came closer. Soon it was to my lips. I looked up at him for reassurance. He had no expression on His face. He simply nodded.

    That was all I needed apparently. I closed my eyes and opened my mouth, allowing the fleshy, bulbous head inside. I wrapped my lips around it and wiggled my tongue. When I looked back up at Him, His stoic expression had changed to one with a huge grin.

    Warmth rushed over me. Like he accepted me for the little slut I am. So His little slut I became.

    I slurped and sucked on the head of His dick like it was a lollipop. Swirling my tongue around it. I tried taking Him as deep into my mouth as possible, but my gag reflex only allowed about half of his massive member in. So I did what the pornstars do. What I watched the wittle sissies do. The ones I watched suck big, massive members. I took my hand and grasped his dick around the base. Making a ring with my fingers to stroke the bottom half as I sucked and slurped on the top half.

    It was then I noticed the ring around my finger. My wedding ring. The one I exchanged with my wife. What would she think of me if she knew what I was doing right now?

    Suddenly there was a knock on the door.

    To my horror, instead of sending them away, He said two words that made my stomach drop: “Come in.”

    I heard the door to the office open. “Hi Charles” it was a woman’s voice. Not my wife’s. No, it was the hot Secretary Stephanie. “Did you get those quarterly reports from Tom yet?” She asked.

    She couldn’t see me as I was hidden under the desk. I tried to take His dick out of my mouth, but felt His large hand on the back of my head holding me there. Forcing me to go back down and continue to suck.

    “No I haven’t Stephanie,” He said, His voice in no way conveying that there was a sissy in panties between His legs currently giving him a blowjob “but if I know Tom, i’m sure he’s putting forth his best effort as we speak.”

    I winced as i continued to suck. Trying to be as quiet as possible.

    “Really?” She said, “I haven’t seen him today, and he’s been acting really strange lately...”

    “I’m sure He’s got a lot going on inside of his head right now” there was a hint of a chuckle in His voice as His dick hit the back of my throat again. “He’s been down recently. But i’m sure he’ll be able to handle anything I serve him” He said.

    That was when the first drop hit. His dick started pulsing, His head swelling. I’ll never forget the taste of that warm, salty goo as spurt after spurt pumped into my mouth. I prayed Stephanie couldn’t hear me slurping as I tried to contain it all.

    “Okay, well...let me know if you need anything!” She said.

    “Ahhhh...will do! Thanks Steph!” He said. And the door clicked shut.

    “What. A. Fucking. WHORE you are!” He said, wheeling His chair back, His slimy deflating member plopping from my mouth. “And you swallowed too! Such a good little gurl!”

    I hung my head in defeat. Ashamed at what I just did. His large hand lifted my drool and cum stained chin. “Awww! Don’t be so sad! This what a little sissy slut like you always wanted isn’t it?”

    I couldn’t even deny it. The amount of times I had jerked my little dick to the thought of sucking a dick was too many to count. I nodded slowly. Wishing it was as fun as I’d fantasized it to be.

    “Good gurl. Now there was a little too much teeth in that one. And you need to learn to take it deeper but you’ll get better. After all, you’ll be getting plenty of chances to practice!” He chuckled.

    “Now...” He tapped His desk to the right. The signal i’d learned meant for me to bend over in that spot. “Awww what?” He said as I whimpered “you think just because you sucked my dick that you get out of your spankings?”

    After my ass was blistered red and I was putting my normal clothes back on He said “tomorrow I want you in lingerie.”

    “B-but...I don’t think my wife has any that fit me...” i said.

    “Then I guess you’ll have to go buy some” he said, turning back to his computer.

    I took at that as my sign to leave and went to the door without argument.

    “Oh, and one more thing” he said as my hand reached the handle. “Get a butt plug as well.”

    To be continued

    Read Part 3 Here

    The Boss’ Baby Part 1 - The Panty Slut

    Tom, can I see you in my office please?

    It was the Boss’ voice over the intercom. I looked up from my computer and around my cubicle. Me? The boss never called me into his office. When we passed by each other, he never even seemed to notice me. 

    As I sauntered to his office I tried to think of any deadlines I may have missed, any one I may have said something inappropriate to.  Maybe he just wants to give me a promotion? I thought. But laughed it off almost just as fast. What would make him promote me over everyone else?

    The Boss’ office was a big one, taking up the entire end of the floor. I knocked on the door hesitantly.

    “Come in.” came the deep, stern voice. “Close the blinds if you don’t mind.”

    I did. I didn’t know why it was necessary, but I did, without question. It took a while as there were a lot, and they covered the entirety of the windows to the office. It went from everyone being able to see inside, to no one being able to see at all.

    “Have a seat.” Boss said. He was a large black man. Bald, stout, with a build and a demeanor that said he didn’t take crap from anyone without even having to say it.

    I shakily sat down in the leather chair at his desk.

    “I’ll cut right to it,” he finally said, after a long silence, “I’m not happy, Tom. I’m not happy at all. Your productivity has declined significantly over the past few months. So I looked into it. Well, I had Dave from IT look into it. And he found that instead of spending time on your computer doing spreadsheets and analysis. You’ve been looking at something...else...”

    My stomach dropped. Fearing the worst. And it was confirmed as soon as He turned his monitor around to face me. There on the screen was a girl with a big, black dick in her mouth. But it wasn’t a girl. It was actually a sissy, because she had dick too.

    “Sissy porn. Sissy sluts. Sissy bimbo BBC.” He read off a clipboard, “Sissy AB’s. Sissy dresses. Sissy suckers. Sissy panties. All from your recent search history.”

    He turned his monitor back to him. Set his pen down. Clasped his hands. And stared down at me.

    I didn’t know what to say. I could feel myself sweating. Shaking. Searching for something, anything to say.


    “So here’s what we’re going to do...” he cut me off with his deep, gravelly voice.

    This was it. I was about to be fired. Oh God how will I afford the mortgage? My car?! What will my wife—

    “Do you have a wife, Tom?” He asked, as if reading my mind.

    “Y-yes...sir...” i stammered.

    A hint of a smile. “Good. Tonight I want you to go to her drawer, pick out a pair of panties, and bring them to work tomorrow.”

    I was taken aback. It was not what I expected to hear.

    “I...her what?” I asked. My voice getting back some of its volume.

    “Her panties.” He repeated.

    Was this guy some kind of sick panty sniffer.

    “For what?” I asked. Trying to sound strong, but it came out more pathetic than i’d have preferred.

    “Well...isn’t it obvious?” He said. Spreading his hands. Chuckling. “You’re going to wear them.”

    Again he caught me completely off guard with his response.

    “Wh-at? Why?” I asked.

    “Well...” he said, nodding to the screen and sheet of my search history. “Obviously it’s something you’ve fantasized why not make it a reality? Unless, of course, you would rather lose your job, and have to explain to your wife why that is...?”

    “No! No...” i exclaimed “i’ll...i’ll do it.”

    He smiled. “Good. Then we have an agreement. I expect them to be worn under your suit tomorrow. I will know if you have disobeyed me. Dismissed.”

    He said. Without another word.


    Tom, can I see you in my office please?

    It was the next day. His voice over the intercom was the same tone as the day before.

    My heart was pounding through my chest as I headed to the room that was His office. The same way it did last night as I snuck into my wife’s panty drawer when she had fallen asleep.

    I knocked at His door.

    “Come in.”

    I forgot to breathe as i entered.

    “Close the blinds” he said. Not even looking at me.

    I did. Standing there awkwardly when i was done. Unsure if i should take a seat or not, I just shifted my weight back and forth, waiting forever for him to acknowledge me or even glance my way.

    He clicked and tapped on his computer and keyboard. Seeming to take pleasure in making me wait. Finally he sighed, sat back in his chair, and looked directly at me. I shrunk in his gaze.

    “So.” He said “did you do as I asked?”

    “Y-yes sir...” i said, nodding probably more than I needed to.

    He smirked. “Good. Show me.”

    I hesitated. “Wh-what?”

    “Show. Me.” He commanded. Emphasizing each word in a way that said ‘do not make me tell you again’

    An infinite amount of thoughts went through my head at that moment. But the one about me getting fired stuck out the most. I sighed. Deciding to get it over with as soon as possible. Pulling at my belt rapidly.

    “No. Slowly. ” He said. “Start with the shirt.”

    Again it wasn’t what I expected. But I didn’t want to refuse. I felt like a cheap stripper as I slowly started to undress for him. Taking off my tie, my shirt, finally my belt, turning around so I didn’t have to look at him as I slowly pulled my pants down. Exposing the lacy pair of purple panties underneath.

    I didn’t know what he thought. What his expression was. I glanced behind me as pants fell to my ankles.

    For the first time, I saw him smiling broadly.

    “Well aren’t you the little slut?” He said. Chuckling.

    I felt naked in his eyes. Probably because I mostly was. I wasn’t sure if i was shivering from the cold or from the power of his gaze.

    I was suddenly very aware that the door to his office was unlocked. Someone could walk in at any moment. But he didn’t seem to care.

    “Come here.” He said. Tapping on the desk in an area directly next to his chair.

    I didn’t argue. Just tried to clench my shoulders together in a pathetic attempt to cover up as I sauntured over.

    I stood in front of his chair behind his desk. Suddenly aware that my 4 inch dick was as hard as it was when I first put the panties on this morning. A tiny wetspot stained the front from my precum.

    He sniggered. “You’re loving this aren’t you, you little whore?”

    I tried shaking my head and let out some pathetic sounding “No”. But my body betrayed me, not that He would be fooled.

    “Awww, i think you do...”

    I flinched as He reached up with his huge black hand and touched the small of my back. I felt so exposed. So helpless as his hand traced my smooth skin down to my plump, almost feminine backside. He cupped my pantied ass. Breathing heavily. I was suddenly much more uncomfortable. Being groped by my big, dominant Boss.

    “Bendover.” He commanded.

    My brain wanted to refuse. To put a stop to all of this. But before i knew it my body was bent over his desk. My pantied bottom out in front of him.

    “Is there a reason you chose these in particular?” He asked, fingering the lacy purple boy shorts.

    “N-no sir...” i said. But I was lying. I had actually spent hours last night trying to decide on the right panties to wear. First there was color: I didn’t want to wear pink, it was too feminine. White was too...boring. And unfortunatey my wife didn’t own any blue. Then there was the style: a thong seemed too slutty, pathetic and uncomfortable. And granny panties seemed too...conservative? Jesus. Had i really thought about how I wanted to look sexy for another man in panties??

    “Hmmm...” he growled like a predator as he ran his hands over my lacy bottom. “Do you like them?”

    “No sir...” i lied again. Suddenly I felt a hard smack across my backside. I let out a surprised squeak as he spanked me.

    “Don’t lie to me.” He said. “Tell me how much you like your prissy panties.”

    I hesitated for a second. But another three spanks had me whining “i...i love my prissy panties! They...they make me feel so....pretty....”

    It must have been a satisfactory answer. As he stopped spanking. At least momentarily.

    “You will wear panties under your clothes every day until I say otherwise. Is that understood?” He asked with smack.

    “Ahh! Yes sir!” I squeaked. Worried the sounds of the spanking or my pathetic whimpers could be heard by the workers outside the office.

    “You will report to me every day at 10 am. If you are not here in my office with your pants around your ankles for inspection there will be consequences. Do i make myself clear?” Another smack.

    “Mmmphh! Yes sir!” I said. Trying to muffle my cries.

    “Good. Now tell me that you’re my little panty slut!” He said. Smacking my ass hard 3 times.

    “Ow! Oww! OWWW!” The stinging on my ass was getting unbearable “i’m your little panty slut!”

    4 more smacks. “Louder!” He growled.

    “Ooo! Ahhg!! Ahhhiee!! UNNNHH!! I’m your little panty slut!!!!” I cried. Using my full voice. Surely someone outside could hear.

    5 hard spanks. “LOUDER!” He boomed.

    “AH! OOH! OWoW! AHHHGG I’M YOUR WITTLE PANTY SLUT!!” I yelled. Panting. Crying. Willing it yo be over.

    And it was.

    “See you tomorrow slut.” He said. Pushing me off his desk.

    I trembled as I put my clothes back on over my panties sandwiched by a glowing red bottom.

    I spent the rest of the day at my desk shifting my sore bum. Wondering if any look that came my way was because my coworkers had heard what went on inside the office.

    To be continued.

    Author’s Note: This story has been in the pipeline for a while but I’ve been hesitant to launch it because it doesn’t have diapers in it. But after seeing so many people respond to the survey saying they want to see more forced fem, I decided to push it through. There will still be diapers eventually, but this will be a more slow-burning, character-driven story. I really hope you like it! Stay tuned :)

    Here’s Part 2


    A kinky scenario and questions for you: thickly diapered, a bonnet and mittens and booties. Nothing else. You wake up dressed this way, on your knees with a paci gag and wrists cuffed above your head to a men's urinal. You have no memory of how you got there. A sign hangs from your neck: "Sissybaby. Free to use. Enjoy. I'll be back in five hours to collect my prize." Questions: first thoughts that go through your mind? And second, do you try to escape?

    This inspired me to write a short story:

    The first thing that hits me is the smell. Where am i? The darkness turns to intense bright light as I stir groggily and rub my eyes. But wait, my hands are stopped by a chain, they’re cuffed between two urinals, and they’re stuffed inside of mittens.

    “What the fuck?” I try to say, but nothing comes out. It’s muffled by something hard, long and plastic stuck in my mouth. I wrestle with the chains. In addition to the clanking comes a crinkling. I look down and see a large, fluffy pink diaper between my legs. Now my brain registers the cold, damp feeling of the soaked padding of the diaper.

    There’s a sign around my neck, but my brain is too fuzzy to read it. “How did i get here?” I think. Starting to panic. I remember being at bar last night. Faint images of a beautiful woman. Smiling. Bringing me drinks. I thought that was an interesting change of pace. But what—

    I’m interrupted by someone entering the rest room. They stop. Perplexed. I see his eyes migrate from me in shock, and make their way down to my sign. Then understanding fills their demeanor as they smirk and take the urinal farthest away from me.

    I wriggle and writhe in my chains. Begging for help. But all that comes out are muffled moans. He just ignores me and goes about his business. Taking a leak, zipping up his fly, washing his hands, and leaving me whimpering on the floor.

    I struggled again futiley with the chains. Trying to adjust my diaper with my hips to stop it from being so cold and icky feeling. It didn’t work.

    Soon, another man walked in. Again with the same reaction as the former. But this time, instead of taking the urinal furthest from me, he approached of the ones i was chained to. I had a front row view if him unzipping his fly and pulling out a very large member. I tried not to stare as he whizzed inches from my head. I could see his large meat flapping as he shook out the remaining drops. Closing my eyes and praying for it to be over. After not hearing him zip up, i peaked out to see what was taking so long, and saw him standing directly in front of me. His large cock dangling out of his zipper. His face smiling down at me wickedly.

    I cowered in his shadow. And flinched as he reached down behind my head. I thought he was going to strike me, but instead he undid the belt around my head holding the gag in my mouth.

    He let it plop out and fall to the floor. “Pl-please sir...” i breathed, trying to get feeling back to my jaw. “Please help...get me out of here...i-i think there’s a key...there’s got to be a key...”

    But the man just continued to smile. Nodding at the sign around my neck. For the first time i looked down and read it. “Sissy Baby. Free to use. Enjoy. I’ll be back in 5 hours to collect my prize.”

    My stomach dropped. With renewed vigor, i tugged and yanked on my chains. “Help!! HELP!!” I screamed. “Somebody—“ but a backhand across the face shut me up.

    First i saw stars. Then the head of a large, swollen prick inches from my face. “If you use teeth, you’ll lose them.” He said.

    “No! Wait! Please! Don’t! I...i have money! Pleashhhummphh” my pleas were stifled as he pressed his cock into my mouth. The first thing that hit my senses was the taste. I’m not sure if it was urine or precum that hit my tongue first. But the fleshy invader was mot pleasant.

    All i could do was watch and try to relax as he forced his meat into my mouth and down my throat. I gagged. Choking. But it didn’t stop him. I looked up at him with pleading eyes. But he just smiled down at me like a was a toy he was playing with. When he had his dick down my throat to the point where his balls were against my chin, he kept them there. Taking pleasure in watching me struggle and squirm. Tears leaking down my face. I noticed they were black. Like i was wearing mascara.

    Finally he withdrew so that the tip was at my lips and i could breathe again. But i was given little time before he slammed it back in. Proceeding to use my mouth as his personal fuck hole. The chains clinked, my diaper crinkled, and my head was pounding against the wall as he thrust in and out.

    I’m not sure if i blacked out or just turned my brain off like some bimbo slut, but the next thing i remember is the feeling of the head of his cock swelling in my mouth. His balls pulsing. The first shot of his load hit the back of my throat. Then the tip of my tongue. Filling my mouth with warm, salty goo. He pulled it out and used my saliva, snot, and tears as lube to pump his cock and the rest of his jizz all over my face.

    He ignored my cries and gasps for air as he put the gag back in. It was in the shape of a penis. Though thankfully not a penis as big as his. Once he had the belt of the gag fastened he pulled up his pants and fastened his own. He left without another word.

    I wish i could say that was the only incident...but it wasn’t.

    One guy came in and took his time inspecting me. Groping my non-existant tits and my soggy crotch as he whispered in my ear and told me what a fucking slut i was. He had me blow him. He didn’t fuck my face like the first guy. Instead he made me do all the work. Bobbing my head in my uncomfortable position and slobbering over his cock like the slut he told me i was.

    At one point two guys came in at the same time. Both of them laughing. Taking pictures. Taking out their dicks and smacking me in the face with them before they both peed on my face and into my already soaked diaper.

    Finally, after what seemed like days. The door opened again. I wondered if it would be multiple guys again like the last crew. The ones that held me up, moved the diaper to the side, and forced their dicks into my ass one at a time.

    But no, this time it was a woman. The woman from the bar that i faintly remember from the night before.

    “Ooo looks like you had fun sissy!” She said. Smiling wickedly at the pathetic person covered in cum and piss before her. “I didnt get any complaints about you either. Congratulations. You passed your test. Looks like i have a new sissy to add to my stables!”