WARNING: May contain themes of female domination, chronic pansexual tendencies, an assortment of kinks and toxic traces of brattiness—obviously all of it is 18+/NSFW.

Last update
2020-11-27 21:01:10

    Sissy boyfriend

    So when I was dating a former girlfriend, after a year or so of dating I decided that it was time to let her know about all my fetishes and dirty little secrets, and while she was surprised, she accepted it and said that she was open to my ideas (which made me very happy) But little did I know just how open she really was. One boring day we decide to play a game of blackjack (i’m not the best but do know the basics of the game) my girlfriend at the time decided that we have a wager, so I tell her “well what did you have in mind?” She says “ If you win, i’ll do anything you ask for the whole following day, but if I win, you do anything I ask all day tomorrow” so of course I agree to the wager and we start, my girlfriend ends up beating me by a landslide victory on our last game. So tomorrow I would be at her complete mercy (not knowing if that was good or bad) but was soon to find out. The following morning I wake up and my girlfriend isn’t in bed, so I get up and walk into the kitchen to find some items on the table. When I get to the table I find: A beautiful hot pink maid’s uniform with white petticoats, a pair of hot pink stockings, pink high heels that had what seemed to be ankle cuffs attached to them, both had small heart shaped padlocks beside each shoe, there was also what looked like a bra with a very large pair of fake breasts built right into them, a pair of lace panties covered with pink hearts, a bright blonde wig and a note beside that read “Dear Kailee, I went shopping for a few things that I forgot, I want you to take a shower, use my girly smelling body wash and I want everythingcompletely shaven, afterwards get dressed with everything on the table and wait for me in the living room, see you soon sissy boy<3” I was immediately erect and my heart was racing, I couldn’t believe this was happening! I rushed upstairs and got all cleaned up, shaved my face, arms, armpits, chest, privates and legs, then I went back into the kitchen, covered by nothing but a towel, my heart was racing with excitement, I started with the fake breast bra, then uniform, then the stockings, locked on the heels, positioned the wig, last was the panties, which was almost too difficult to get on with my hard cock, but I managed to get it on. I then wait in the living room, all dressed up and ready for her next command, I then hear the front door open, she’s carrying 2 handfuls of bags. She then starts to empty the contents of the bag to reveal: A pink chastity device, a pink vibrating butt plug, a leather paddle, handcuffs & ankle cuffs, a roll of duct tape and a bright pink collar that read “Sissy Kailee” on the front. She sat me down in the bathroom and started putting makeup on me, eyeliner, eye shadow, foundation, concealer and lastly bright red lipstick. She moved to the side so I could look at myself in the mirror, it was incredible.. I looked just like a pretty little girl, my cheeks burned red as she started cooing and telling me what a pretty girl I was. She then called me back to the kitchen, first was the chastity device (which was a very tight squeeze) then the handcuffs & ankle cuffs, then she put on my collar and locked another heart shaped padlock on the back. She then hooked a leash to the front of the collar and led me to the back door (that’s when I started to panic) I said “where are we going?! I don’t want anyone to see me like this!” She said “hush your mouth! We’re going for a little ride sissy and if I hear another word i’ll make you be quite!) I protested and said “No please don’t take me outside!” That’s when she walked back to the table and grabbed the duct tape and the vibrating plug, she slips off her panties, completely soaking wet from all the excitement, she then shoves them into my mouth and wraps the duct tape over my mouth and around my head, “ I told you I didn’t want to hear another word out of you, now I have to tape your sissy mouth shut so we can continue our fun hehe!” The smell of her pussy lingers into my nostrils and the taste fills my entire mouth, I try to make a sound but I cant make out a peep. She then proceeds to walk me outside to the car, luckily nobody was to be seen outside, she then shoves me face down into the backseat, pulls down my panties and starts to put lube on her fingers, “I almost forgot to give you your toy that I picked up today, I’m sure your sissy booty will love it” she then slides 2 fingers into my ass and slowly starts to finger bang me, she does this for about 5 minutes or so before sticking the plug in my ass. She then turns the power to the highest setting, the vibrations are so strong I can hear my butt cheeks shaking! My locked up cock is starting to ache from trying to get erect, I start to moan and groan as a small wet spot appears in my panties, “looks like your enjoying that toy, I’ll just leave it in for the ride” she says. She then drives me about 10 miles outside of town into the country (hardly any houses to be seen) she then turns down what seems to be trail just small enough for our car that leads back through A wooded area, she stops once we are not visible from the road, she then opens the glove box to reveal a very realistic 8 inch strapon, gets out, climbs into that back seat with me and starts putting on the huge strapon. “Stick that cute ass in the air sissy!” She says, I do as she says and stick my butt up in the air, she pulls out the plug, still buzzing away, she applies more lube to my sore gaping asshole, then starts stroking it onto her massive rubber cock, I try to protest, but the cum soaked panties and duct tape keep any noise from escaping my painted lips. She slides the rubber cock into my ass, completely filling me up, I whimper and moan as she starts to hump my ass faster and faster until she is full on fucking me up my ass, as if i’m a cheap hooker she found on the corner. This continues for nearly 2 hours before she finally tires out, my ass has never felt so sore and little did I realize that I even came all over the back seat, “Well it looks like someone enjoyed themselves” she said “you made a big mess in here, so you’re going to clean it up!” She then untaped my mouth and removed her now spit soaked panties, “lick it all up” she says, I just hesitate, not really wanting to do such a humiliating act, “I said lick it up sissy!” She yells as she pushes my face onto the cum soaked seat, I start to lick it up and swallow every last drop on the seat, “Good girl, lick up all of that sissy goo!” She says, after I finish, she takes off the strap-on that was used to violate me and she stuffs the 8 inch dildo down my throat! She starts to wrap duct tape around the base of the dildo and my head, so it’ll be impossible for me to spit out, I start to gag and feel as if i’m choking, breathe through your nose!“ She tells me, I start sucking fresh air through my nostrils as hard as I can, she keeps me that way the entire car ride back home. Once she leads me by my collar back into the house, she removes the dildo from my mouth, spit dripping down my chin and the taste of my own ass in my mouth, I start begging her to release me, “please, no more” I plead, as she stands in front of me with the leather paddle, “Last time I checked, I won our little bet, so your ass is mine sissy!” She said as she bent me over her lap starting to mercilessly spank my bare bottom with the leather paddle, I squealed for her to stop as she counted ever smack of my ass, counting all the way to 100. She then told me to stand up as I wimpered and sniveled, tears beginning to well up in my eyes, she begins to wipe them away as to not ruin my makeup, she then leaves and comes back with what looked like a pink diaper bag, she then pulls out a diaper and a rather larger pacifier with straps attached to it, she puts the pacifier in my mouth, the large tit completely filling it up, then tells me to lay on the couch, she starts to put baby powder on my bottom and my locked up clitty, telling me that i’m going to be her pretty little baby for the rest of the night, she puts the diaper on me and pats my bottom. She then grabs the leash still attached to my collar and leads me into our guest bedroom, to my surprise there is a large adult size baby crib is sitting in the corner, covered with pretty pink sheets, a large stuffed teddy bear and fitted with restraints on all corners. “It’ll take a little time, but we’ll turn this into the cutest nursery ever! Hehe!” She said with excitement, “ Now my little baby girl has had a long day, so I think it’s nap time” she removes my ankle cuffs and handcuffs and straps me into my new crib for the night, I try to speak, but my words are muffled by the large pacifier strapped into my mouth, she removes it so I can repeat what I said, and I tell her “I love you, so much” With a big smile on her face, she kisses me and says “Mommy loves you too sweetheart” She then straps the pacifier back into my mouth, lays a cute white blanket covered with pink hearts over me, turns out the light and says “I think we’ll just make this last the rest of the week, see you tomorrow my sweet baby” then closes the door. There I laid, completely restrained, mouth filled to the cheeks with a very large pacifier, a padded diaper as my only bathroom until morning, I was completely helpless and under her complete control, and I’ve never been happier.


    Sounds like a great day with a great woman!


    There are many reasons why a wife would lock her husband. All are eqully valid. However, the important thing is that the husband is actually locked in a chastity cage and the wife is determinedly controlling the keys.


    beta boi, do you still need an explanation for why a steel chastity device is permanently locked on you?