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Babysitter to sissy baby


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This is a story of Jack, an adult baby sitter, becoming an adult baby by the adult baby he was babysitting

Jack pulls up into the driveway of his first client, Mrs frizzle, quickly checking his phone making sure he's at the right address, his first job, jack wanted everything to go right. He got out of his car and went to the trunk to grab his luggage and supplies. He walked up to the door and rang the doorbell. After a few seconds a lady answers the door who he recognized the voice of, it was Mrs frizzle.

"Oh goodie, you're here, ok, I'm off on my trip, you have my phone number if there's any trouble and Katie is inside asleep in her crib. Now if you would excuse me, I have a plane to catch"

Jack was taken aback by the sudden rush out of the door by Mrs frizzle, "she must be really late" he mumbled to himself. He turned and walked into the house, he was now In charge of the house for the next four days, being paid $150 a day, he thought "$600 to watch a baby, even if it's an adult baby, it's a steal." He hears crying in the next room and goes to look in the room and he sees an about 18 year old Katie sitting there in a obviously wet diaper. "Well time to get to work"

Jack goes and unhooks the crib and opens it, he grabs Katie and takes her to the changing table across the room "well, I'm going to be your daddy for the next four days" Katie obviously didn't like that for she started to kick and yell

"WE DONT NEED A DADDY, WE NEED MOMMY!"

Jack had trouble holding on to her for being 21 himself she only weighed about 15 pounds less then him "that's enough, im in charge and you have to listen to me." He wrestled her over to the changing table and laid her onto it. Katie calmed down when he started to change her. Jack grabbed a pink diaper off from the shelf and said "this is cute!" And put it on Katie. After she was all diapered, she started to fuss again, jack knew he had to get some authority on this baby so he said "hey, if you don't behave, I'll have to spank you!" Thinking this will get her to stop jack relaxed only to hear Katie yell

"OR MAYBE I SPANK YOU!"

Jack once again was taken aback, but then chuckled to himself "I guess I have to spank you then" he grabbed her wrist and dragged over to the crib and went to sit down but right when he was about to Katie yelled

"That's it time for your spanking!"

"Oh yeah, we'll see about..." Jack didn't finish his sentence when he felt his feet fall from underneath him and he fell forward over Katie's lap "now wait a minute" jack was saying but was interrupted by a smack, Katie just spanked him, and it hurt! He let out a Yelp, Katie then pulled down his pants and underwear "if it hurt with my pants up then..." "WHACK!" Jacks entire butt felt like it was on fire, he yelled as another smack came down, and another and another. What seemed like hours to jack finally stopped, he was crying, this wasnt supposed to happen he was in charge, he was the babysitter! Katie stood him up and said 

"Aww, what a cry baby, your acting like a baby girl, so why don't you look like one." Katie dragged jack across the room the the changing table and jack was defenseless, he was to focused on the throbbing pain in his butt, he didn't realize what was happening until he was handcuffed to the charging table and Katie pulled off his pants, he turned completely white when he saw the pink diaper and he started to struggle, but his stuggle was quickly ended with another spank on his bare bottom, he was quickly diapered and Katie walked over to the closet, jack wanted to know what she was doing and when she walked out with the most frilly, pink dress he knew exactly what was about to happen as she walked over he yelled 

"I'm the babysitter, you can't do this!" And with a quick smack to the butt he shut up.

Katie said "Now I said we need a mommy not a daddy, so I'll be the mommy and you be the baby" she unhandcuff him and threatens him by raising her hand, jack got so scared he wet his diaper on the spot. Katie takes off his shirt and pulls the dress over his head, she stood him up and held him in front of the mirror, jack felt every bit of his manhood drain away as he was a baby girl with a wet diaper. He realized this was going to be the next four days.

"No" he thought "no" he said out loud, "I'm the babysitter and you're the baby!" He grabbed Katie's hand and twisted it around, he was not going down without a fight. He quickly got control of the situation and had Katie's hand behind her back with him having a strong hold of it, then she started to cry.

"Please let me go, you are hurting me, I'll be good, I'll behave, I promwise!" Katie wined. Jack loosen his grip and started to let go, once her hand was free, Katie elbowed Jack in the stomach and there was a toot in his diaper. She swings around and starts to fight again, jack defends himself but feels a cramp in his stomach and struggles. Katie hits jack again and there's another toot, she goes for one more hit and slugs him as hard as she could.

"Thuuuurrrrbbbbb" jack suddenly stopped as he felt the back of his diaper fill up and he froze, Katie took advantage of the situation and tackled him to the ground causing him to fall on to his freshly messed diaper. Jack looked up and just got what happened, he had just been beaten in a fight by a girl, not any girl but the baby girl he is babysitting, after he wet and messed the diaper she put him in. He didn't know what to do, he looked at Katie who was sitting on his chest.

"Don't worry" Katie reassured jack "its ok" she lifts her butt a little and turns around for Jack to see, he heard her moan then the diaper fills up in his face. He quickly gets out from under her and trys to stand but falls back on his butt. "See, nothing is wrong, you just went to the bathroom."

Jack looks at Katie oddly, he starts to stand up and she shoves him down again and crawls up to his face then licked his nose. "Can you do something for me?"

"Uh, what is it?" jack asked suspiciously

"I don't want to be the baby, I want to take a break, so how about instead you can be my baby and I can be your mommy!" Jack was intrigued by this, he has read about this happening but haven't giving it much thought, what was it like to be on the flip side. "So, what do you say?" Katie came closer to Jack's face with the cutest smile, how can he say no to that face?

"Well, I don't know, this isn't what I signed up for." Jack said

"Oh come on, you'll still get paid, mommy doesn't have to know, Please!"

Jack thought and came up with a clever answer "alright, but one night, if I don't like it we stop, if I somehow do, I'll consider it, alright?"

"YAY, It's a deal!" Katie leaped forward with delight knocking jack over in a hug. "First things first, I think someone needs a diapee change" she pressed against the back of his diaper which made him uncomfortable and made him squirm, she smiled at this. She stood up and helped him up and put him on the changing table, she didn't handcuffed him and jack took this as a sign of trust and decided not to take advantage of it. She efficiently changed him and got him into a new diaper before he knew it, he was still thinking what was going to happened. He was trying to remember all of the stories and guess what she was going to do next. 

"Ok, all done" Katie lifted jack off the table and jack started to waddle, this diaper is different, thicker, he lost his footing and fell onto his knees "aww, poor baby, I guess you have to crawl from now on." Katie mocked. Jack relized she did this on purpose, she is smarter than he thought. He started to crawl around and noticed that Katie was still in her messy diaper.

"Are you going to get out of your diaper now since" he swallowed "you're mommy?"

"Nope, I need it still, but I'm still mommy which means I get to make dinner! Follow me baby" She walked out of the room. Jack followed crawling in his oversized diaper and a frilly dress. This wasnt what he signed up for, but strangly, he wasn't going to fight it, this should be interesting.

 

Add ideas in the comments for what you might want to see. Thanks for reading so far, more to come! :)

 

Edited by Movableacorn
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  • Like 2
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  • 11 months later...

I guess you're not going to continue this story.

What a shame it was good. Would have loved to see him in a pink diaper

and a dress and Katie treating him like a baby girl. She could feed him let him suckle

and give him baths. There are a few suggestions for you. Don't keep us hanging.

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  • 2 weeks later...

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