Babysitter Humiliation (Patreon)

Hey sleepyhead, how are we today? You seem surprised to see me. Your step mom is out for the next few days with your dad so she asked me to come in and babysit the lot of of you. Now the girls told me their mom checks your pull-ups when you wake up. Do I have to check your bum too? 

Don’t be embarrassed. I know I’m technically their babysitter, but the fact that your step mom hired me even though you’re here makes me think you were probably included in the charges for me to watch over… and when I learned that you still take afternoon naps and wear Pull-Ups to bed it only confirmed my suspicion. Think of me the same way you would of the girl’s mom. She checks your butt after your nap, doesn’t she? 

Well I wouldn’t want a leaky diaper to reflect badly on me if she gets home and I haven’t done my job properly, right? Don’t worry, I’ve babysat a lot, I know how to change Pull-Ups, this looks like the same thing, only in a bigger size. Come on, show me where you keep them.  

Aww that’s just too much. You’d think I’d feel bad for making fun of you, but with the attitude you keep giving me, I just can’t help it. You wanted to play the big tough guy, but you’re just a scared little boy in Pull-Ups who’s gonna pee himself tonight like you always do. If you were younger I might actually feel bad, but we’re practically the same age, so seeing you in your diaper makes me laugh.  

You’re not making jokes anymore, are you? Are you gonna cry or pee in your training pants? It looks like both. 

Show me… oh I don’t think these will do sweetie. Those are too manly for you, if you could call them that. I’ve brought something else with me. 

Aww why are you pouting like that baby? You’re gonna look SO cute in those. Look, there’s Minnie Mouse on it, isn’t it adorable? Listen, your step mom hired me as your babysitter, so I’m the one who’s in charge tonight, okay? I don’t care that were roughly the same age. She told me what happened last time you were staying over at a babysitter’s…   Oh you don’t remember, do you? Well I know all about how you got pushed around by the little bully on the block when you were playing outside and how you got so scared you had a bit of an accident in your pants. Yup, your step mommy told me how you were crying and had a wet spot on your pants when she picked you up.   So I decided I’m gonna make sure that doesn’t happen here. If you can’t hold it like a grown up, you’re not gonna wear grown up panties in my house.   Oh it was just that one time, was it?

Well I don’t really care about it cutie. You’re putting on these Pull-Ups right now whether you like it or not. It won’t be so bad, you’ll see. They’re just like your regular pull-ups, except a little bit more girly. After a few hours in them you won’t even notice it anymore and you can be sure you won’t embarrass yourself by making a mess. If you do we can simply change you in another pair, isn’t that convenient?

Oh yeah, I have a full pack of those. I picked them up at the store just for you! I wish I could tell you they were for my other babysitting charges, but all of them are potty trained… unlike you.   Come on, I have some friends coming over later tonight so if you want to keep your pants privileges while they’re here  you better stand right up and let me slide these on your butt. Otherwise you’ll be walking around in just your Pull-Ups and a t-shirt all night. It would actually be easier to check for accidents that way, so don’t think I won’t do it. Hurry up now. 

If you keep them dry for the next few days I might consider letting you wear the blue ones. That’s right, you can wear ‘’big boy’’ Pull-Ups BUT if you do have an accident, then I’ll take away your pants privileges. Can’t risk you leaking all over your pants, can I? If you’re gonna start wetting yourself, I’ll have to keep a close eye on you and that means no more hiding your training panties under your clothes.  

When we’re out and about you’ll get to wear pants, but as soon as we’re in the house, we take it off and you’ll parade around in your cute princess Pull-Ups for everybody to see. Sounds fair? Deal! But I didn’t tell you the best part yet. Since your step mother is away for a few days, I get to make all the rules. And from now on you only get access to the bathroom once per day, before you go to bed. So I hope you didn’t drink too much this morning, because you won’t see the potty for another 10 hours.  

Now if by any chance you have a little accident and you need a change, I want you to come and get me. I don’t care who I’m with. If you’re too embarrassed because my friends are around, you can whisper in my ear… but if only your step sisters are around you have nothing to hide from them. As a matter of fact, they’ll be allowed to check you for me and if they find you wait and you didn’t tell me… you’ll get yourself a spanking.  

If you do notice that you’re wet, I want you to go grab a pair of pink Pull-Ups and bring it to me. If you fail to do that I might have one of the girls fetch it for you, would you like that? No? 

Well then you better behave yourself. Alright, put some pants on diaper butt. My friends are coming over soon.  
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This story was written by Pullupfiction
Find their blog here:
https://pullupfiction.tumblr.com/