Your New Babysitters (Part 1) (Patreon)

 The doorbell rang. You knew what that mean. Your parent’s threats were coming to fruition. You were only expecting the worst. They had left the house for about an hour and said that your ‘’babysitter’’ was coming over.

You knew it was a payback for hosting a house party at their house the last time they were out of town. Obviously you were way to old to require supervision, espcially now that you were legally an adult. But you were still living under their roof and if you wanted to go on vacation with them at the end of the summer, you’d have to comply.

You headed over to the door and expected an old lady, maybe a neighbor. You opened it and were shocked to realize that it wasn’t an old lady at all, but a stunningly beautiful girl. You recognized her immediately. Kelly Lopez. She attended the same school as you, only she was a year older.

Kelly: Hey you must be Jordan.  Can I come in?

Jordan: Huh... yeah, yeah of course.

She was carrying a white bag with a pink heart on the side as well as what looked to be an overnight bag. So she was actually gonna stay over - neat. As soon as she’d realize how much of a joke this was, maybe you could get in on some action. Watch a movie, cuddle... and who knows? But for now you had to play it safe... After all, she expected this to be a babysitting gig.

Jordan: So... This is so weird, right?

Kelly: What do you mean?

Jordan: Well... you know, my parents asking you to come here. You must be wondering what you’re supposed to do.

Kelly: I know exactly what I’m supposed to do: keep an eye on you so you don’t get into trouble. And that’s what I intend on doing. 

She smiled. You couldn’t tell if she was pulling your leg or if she was actually serious.

Jordan: ... Sure. Okay. But you gotta admit it’s a bit strange. I mean we go to the same school, we’re almost the same age... You must be used to.. younger ‘’charges’’ huh?

Kelly: Not really. I specialize in this kind of service, you’d be surprised who I babysat. My last one was a girl your age... maybe you’ve got classes with her?

Jordan: No way! Who was it?! 

Kelly: Everything I do is confidential. I think you’ll appreciate that quality later on.

Jordan: Okay, you’re a mysterious one aren’t you? Well make yourself at home.

Kelly: Where your bathroom?

Jordan : Oh, just down the hall, there’s only one so you can’t miss it.

Kelly: No.. but maybe you will.

Strange girl.

*

Kelly: Okay. Time to get ready for bed Jordy, no more video games.

Jordan: You’re kidding, right? It’s not even 9 yet.

Kelly: You can come back to the living room to play when you’re ready for bed, but that’s how it works. Go brush your teeth and put your PJs on.

Jordan: I don’t wear PJs...

Kelly: Suit yourself then. I put your toothbrush and paste in the kitchen.

Jordan: Why would you do that?

Kelly: Cause that’s where you’ll be brushing your teeth silly. Go on.

Something fishy was going on, but you couldn’t put your finger on it yet. After brushing your teeth in the kitchen sink you headed to your room. You took your clothes off and put on a large T-shirt.

 When you turned around you jumped at the sight of Kelly, waiting in the doorway, her white bag on her shoulder.

Jordan: Whoa. Can I get some privacy here?

Kelly: I just came to help you get ready for bed. I brought all that’s necessary.

You had a puzzled look on your face as she moved in closer and put her bag on your bed. She opened it and pulled out what looked to be...

Jordan: Is that a diaper?!

Kelly: It’s a Pull-Up Jordan. Training pants.

Jordan : What the fuck, why are you giving me this?

Kelly: That’s what you’ll be wearing to bed as long as I’m here, silly. It’s part of the service. Your parents know about it. In fact they were pretty excited about it. They said that if you misbehaved you’d have to wear them not just for a few days, but for the whole time you guys go to Europe, as a punishment.

Jordan: This is.... crazy. 

You picked up the brief that she was handing you and looked at it. Unfolded it looked like granny panties, with more padding. It was white and pink and had flowers all over it, with a little bow on top.

Jordan: Those are girl’s Pull-Ups! 

Kelly: I had a few left after last week’s charge, I hope you don’t mind. Nobody else is gonna see you in them, so what difference does it make?

Jordan: Your... other charge, the girl in my year right? Was it Joanne Stuart? I heard she wore those a few years back. 

Kelly: I can’t say. Come on, put it on. You’ll see it’s not so bad. 

Jordan: My parents are really going far to punish me... 

You looked at the brief once more. What the hell could happen? It was humiliating, but Kelly could make it worse for you if she wanted. You swallowed your pride.

Jordan: Fine. I’ll wear the damn thing. But give me some privacy to put it on... Please.

She left the room with a smile on her face. You closed the door and took off your boxers. One last deep breath, then you stretched the synthetic fabric of the Pull-Up and lowered it to your ankles.

You stepped in it one feet at a time, then slowly lifted it up your legs. The garment crumped under your fingers as it moved up your skin, until you reached your thighs and crotch. It was a bit tight, but it fit you surprisingly well enough. You looked at yourself in the mirror. The t-shirt you wore was large enough to cover the training pants, but you looked ridiculous when you lifted it up. 

What did she think, that you were some sort of bed wetting sissy?