Your New Babysitters (Part 2) (Patreon)

PART 2

You were now clad in a T-Shirt and a pair of girl Pull-Ups, patterned with flowers.
You walked around your room, paying attention to the soft crinkling your butt made. The fit was tight and the padding was rubbing against your crotch, thick between your legs.

You wondered why you accepted to wear them so quickly... truth be told, you were a bit excited about it. You wouldn’t admit it to yourself and certainly not to anyone else, but you were curious. You felt somewhat... aroused at the idea of wearing what really was a glorified diaper.

The idea putting on a pair of Pull-Ups, as if you were expected to have an accident, was oddly comforting. It was as if you didn’t have to make that decision, you just did as you were told.

You walked down the hall and to the living room where you find Kelly, comfortably seated.

Kelly: Did you put your trainers on?

She asked the question matter of factly, as if you actually needed to wear training pants... as if they were YOURS. You played along with the game as you knew it was better to tay on her good side, at least for the night. She wanted to play dress up with you ? Fine... Let her pretend she could.

You: Yup.

Kelly : Let me see.

She was looking at you with a smile. Not a mean, teasing smile, but a motherly one. She just wanted to make sure you had it on. Maybe she wanted to make sure you pulled it up correctly. WIthout thinking too much you lifted up the large T-Shirt that covered up you thighs and showed her the front of the padded undewear, flowers and all. 

Kelly: Good. You’re more well-behaved than my last charge, she needed a good spanking before putting those on. 

You: Really?

You were glad that you complied, a spanking sounded painful and humiliating... although the fact that a girl your age had been more resistant to obey then you were was a bit puzzling. Were you supposed to put up a fight?

Kelly: Oh yeah, she was real fussy. But not you huh? You’re a good boy.

You: Huh... I guess.

Kelly : You look cute in those, with your t-shirt on top, kinda looks like a dress.

You: This ain’t no dress!

Kelly : Don’t be offended, I’m just saying... Well. A dress would definitely go well with the flowers on your Pull-Ups.

You: Yeah right... I just put that on because you asked me to.

Kelly: I know. I appreciate it. Now, do your homework okay? We’ll play a game later on.

You: Okay...

That girl was odd. She was really taking this whole babysitting thing very seriously. You and her were almost the same age! It felt weird to get asked to do your homework like you were a kid. You didn’t mind it though.

Whenever she spoke to you, she had this confidence that made you want to comply. She acted as if she was in total control.

You lied on the floor, on your tummy, like you used to do when you were younger, your books in front of you.

After about an hour, Kelly came over with a bottle of juice and handed it to you. The bottle had a spout that made it look kind of like a sippy cup. You accepted it anyway and drank from it, thanking Kelly for the thought.

She crouched and lifted up your T-Shirt from your butt. Exposing the back of your purple and white Goodnite.

You: What are you doing?

Kelly: Don’t mind me, I’m just checking.

She put her hand on your butt and slid it slowly between your legs, cupping the padding of the training pants in her palm. The aroused sensation came back to you as she pressed between your legs. 

Kelly: All dry like a big boy!

You: Hum... Yeah! It’s not like I’m gonna wet the damn thing!

You said it with confidence, the spout of the water still half in your mouth, drinking from the bottle.

Kelly: I know, I’m just teasing you.

The bell rang. You immediately pulled down your T-Shirt to hide the diaper, on alert.

Kelly: Don’t worry kiddo, it’s just a friend coming over. She knows about my service, she’s seen plenty of charges like you.

You: What? I don’t want someone else seeing me like this?

Kelly: Relax, I’m telling you she’s okay with it...

Kelly walked to the door and opened it. Her friend came in, greeted by your babysitter. You knew her too. Briana was Kelly’s best friend at school. As she walked into the living room and got a look at you, you were feeling extremely nervous. Your heart was racing, wondering if you should play it cool or make a scene and run to your room to hide.

Briana: Oh my God he’s so cute. Doesn’t he go to our school?

Kelly: Oh yeah he does. 

Briana: So are you giving him the full treatment then?

Kelly: Not yet, but we’ve got a good start.

What did that mean?

Kelly: Come here Jordan, show Briana what a big boy you are.

You hesitated, feeling embarrassed and overwhelmed, but at the same time you kind of liked that feeling. 

You got up and closer to the two girls, looking at your feet. When you lifted your chin up, you realized they were smiling at you. Not mocking you, smiling genuinely, with a bit of a twinkle in the eye. With this reassurance, you did as you had before with Kelly.

You lifted up your T-Shirt, slowly revealing your girl Pull-Ups.

Kelly: Higher.

You kept lifting up the shirt until the whole Goodnite was in full view, waistband and all. Without a warning, Briana pressed her right hand on the padding, cupping your crotch. 

Briana: Still dry, too. Wow!

You weren’t sure how to react. She paused for a moment and looked at you in the eyes. You looked right back at hers.

Briana: Now, go.

You: Wh... what?

Briana: I want you to go in your Pull-Ups... right. now.

And you felt it. Like a programmed reaction. Your body let go and you started flooding your flowery Goodnite like a helpless little girl.

You gasped as you realized what was happening and looked down at the front padding of the training pants expanding, with the hissing sound of your urine filling it. Briana’s hand still firmly placed against it, feeling the fabric layer getting warmer and Kelly was watching the scene with a satisfied smile.