Art and story by @kinkedkitters http://kinkedkitters.tumblr.com/
Thank you for the super blushy and adorable story/art combo! So blushy…
Rosey was always a little put off when she first started babysitting crash. No matter what, he was the baby. Despite his age, he was firm in his place in the world, and had his Mommy wrapped tight around his sassy little finger. The worst part was he was well aware of this, and made sure everyone knew. Especially her. She figured if he was gonna go out of his way to be the bratty little brother, then she was just gonna have to start being the mean big sister.
The teasing started out fairly small. She’d pull his hair when his mommy wasn’t looking, she’d steal his juice, and she’d hide his crayons in places he was always too blushy and shy to try and find. Once Rosey started staying over night to watch the little brat, she was asked to make sure he was changed before bed. That ended up opening a whole new door for her once she learned a few more of his weak spots. The teasing got much worse now that she had some new ammunition, not to mention, she had some new places she could put her hands to make him cry. The best part was- he started asking her to do more! She started to bring toys over, now that she had the best of both worlds. She got to be the cool babysitter who brought over fun toys, and the mean big sister who made him bawl like the little baby he really was.
Crashy’s Mommy was trying out something new to make sure Crash was an extra good boy, making sure he didn’t touch himself like a naughty little boy. Mommy made sure to tell Rosey all about how Crash wasn’t allowed to touch himself, he wasn’t allowed any climax, and she was to make sure he listened to his mommy. Lucky enough for Rosey she brought an extra special toy for Mr. Bear in Crash’s playroom! Even luckier for Rosey, Crash wasn’t gonna get to have any of the fun, and had to stay locked up in the tiny little pink cage Mommy put on him.
Rosey got everything set up and called crash over to see Mr. Bear’s special new toy! It was a bright blue cock, strapped onto the charming and oversized stuffie.
“Well come on, crash! Don’t you wanna say hello to Mr. Bear’s new friend here?” Rosey said with a big grin. She got down to her knees and took the boy by his shoulders and pushed him closer until he had his nose pressed firmly on the tip. Rosey stopped pushing there and crash sat there with his eyes fixated on the piece, still wrapping his mind around everything. He was gonna have to pleasure a stuffie! His face got bright red at the idea, not even doing it to really pleasure someone who can call him a good boy, but he wasn’t gonna let Rosey call him a chicken either.
“You’re not gonna try and make friendly with Mr. Bear’s big cock with your nose are you?”
Crash pulled his nose from the tip before letting out a defiant “No! O-of course not. I-I wouldn’t be able to put it in there!”
“Well, Guess I’m just gonna have to tell you how to use it then, huh?”
Rosey said as she stood up, striking a sassy pose for no one else but her self. She bent over and cupped either side of his head
“Open wide!” Crash did as he was told and stretched his jaw out to try and make sure he could fit the whole thing in his mouth.
“Now, just imaging this thing is like a really big paci and you’ve gotta put the whole thing in.” Crash turned bright red at the mention of a paci, reminding him of how little he was. With his jaw stretched wide, he let the interestingly shaped bear cock slide into his mouth, and down his throat like a good boy. Rosey ruffled his hair and patted him on the back to let him know he was doing a good job. Crash stayed where he was, quickly learning that you couldn’t just suck cock like a paci, but he didn’t wanna move until Rosey told him to either. Crash ended up getting red in the face just thinking about how ridiculous and lewd the position he was in was. He was pulled out of his thoughts when he whined at the cold gooey rush that was felt down his spread cheeks from being bent over on all fours. He felt whatever it was pool on top of his hole before dripping down onto his poor, pent up, and caged balls. He could feel Rosey using her thumbs to push and spread his tight hole open, methodically rubbing and pulling before pushing one of her fingers in. Crash cried out with his stuffed mouth, muffling most of his whining. Rosey giggled.
“Aweh, Poor little Crashy is having some trouble! Don’t worry buddy, I’m gonna make sure you nice and ready for this toy! Can’t break Momma’s little baby, can we?” Crash was confused by all of his emotions. On one hand, he loved being used like a little slut, but on the other, his poor wee was starting to get big in his cage. He wasn’t quite sure to feel about his new impromptu gag either. Yet again he was cut short by another finger, prying open his hole. Rosey worked her fingers in and out, making sure to spread her fingers out and slowly rub themselves against all his little sensitive spots. Crash whimpered letting out a muffled moan against the cock, feeling his own start to twitch a little bit, regardless of the cage. His knees rattled and shook with every little move of her fingers. He was panting hard, trying not to make any more embarrassing sounds. He felt the blood rush from his head, and down to flush his little cheeks, keeping his face a nice pink tint. Rosey took her time slowly pulling each finger out and left crash to simmer for a moment and catch his breath. He could feel the cold air on his sticky, well lubed rear. He kept his face in the bear’s crotch, showing his resilience in what a good boy he was, and how well he listened to his sitter. He felt his hole spread again, sending a quick twitch down his thigh all over again. This time, it wasn’t a finger though. He felt whatever it was go down deeper, spreading the poor boy open further. He tried to get away from it, pulling himself away, but he was stuck on the bear. His fighting only caused him to push the cock deeper into his throat. His legs wiggled and kicked as he constantly readjusted himself on his knees, rocking back and forth. He found it harder to whine with the cock deeper inside him, every weak whine and moan was ended by a sharp little gag. He started breathing quickly out of his nose, trying to keep his composure that he was quickly losing as fast as he tried to build it back up. After getting to the hilt of her intricate toy, she pulled it out as slowly as it was pushed in. Like a slow rocker, she slowly brought the toy out, firmly pushing in. In and out, In and out, dragging the process out to hand fulls of seconds, not giving any rest in between. Crash couldn’t take it anymore, with tears streaming down his face, he started to grind his butt against Rosey’s thigh each time she buried the toy in his sticky boy hole.
“Well! Looks like someone’s eager to get going. Getting a little impatient there, squirt. But fine! I’ll give you what you want~” She punctuated her last word with a little sing song hum before picking up the pace that caused a sloppy slap each time her thighs hit the backs of his twitchy legs. Crash could barely keep up any longer. He buried his face into the bear with tears streaming down his bright red face. His breathing was hard and broken up by gagged cries and moans, he was trying so hard to ignore it, he was a good boy- he wasn’t gonna let it happen,hewasn’tgonnaletithappen, hewas a good bo-
Rosey let up and pulled herself out and looked down at the floor. Poor little crash had an accident and made a mess through his cage. Crash felt the tears fall, on his bright red, hot face. Rosey gave him permission to spit out the bear, and without hesitation, Crash dropped the cock from his mouth and let his face and shoulders hit the ground. He left his used hole in the air as the twitches from his legs and everywhere else subside before pleading in a shaky voice.
“I-I’m sorry Rosey! Don’t tell Mommy, Pu-Please. I-I was trying really hard to be good!” Rosey pushed the chair out of the way and sat in front of the high pitched whining boy. She pulled him onto his side and laid his face on her thigh. She petted his hair out of his teary face.
“You’re still a good boy crash, it was an accident. We don’t have to tell Mommy all of your accidents do we?” She gave him a playful grin and ruffled his hair.
Crash smiled, sniffed, and wiped the tears out of his eyes before giving a soft little giggle. “Th-thank you Rosey”
“Don’t mention it squirt.” Rosey stuck her tongue out playfully before pulling back her strap on and flicking him in the face.
After all. She was still the mean big sister.