Your New Babysitter (Part 5) (Patreon)

Part 5

You were now sharing your babysitters with a new charge : Gabriella. 
She was also in your year at school, in an another class. You hadn’t really noticed her before. She was a quiet young woman who had very strict parents. When they heard she was failing a class, they took matters into their own hands and asked Kelly to watch over her while she was doing her homework.

What started out as a form of tutoring quickly became a babysitting session and Kelly had Gabby’s parents convinced that the reason their daughter was failing school was the lack of discipline at home. She introduced them to her form of ‘‘regression therapy’‘, forcing Gabriella into children’s training panties to make sure she ‘‘knew her place’‘. 

It seemed like Kelly’s manipulation had worked because Gabriella was now at your house, a pair of childish cotton training pants firmly placed on her butt, under her blue sundress.

You would’ve thought the situation was improbable... if it wasn’t for the fact that you were also wearing training pants of your own. 2 of them one on top of the other to be exact.

Even worse : yours were disposable girl’s Goodnites.
Even though Gabby’s training panties were probably originally meant for younger girls then your Goodnites were... they at least didn’t come a in a package sold in the diaper aisle. Yours were made for older girls who still wet the bed every night, hers for little girls who in case of an occasional accidents, but that was about to change...

Briana: I don’t think Gabby’s cute undies are appropriate for our games, are they?

Kelly: You’re right Bri. Mommy and Daddy might think these are enough, but I think you need a bit more protection. Let’s see what they packed for your bedtime.

She placed Gabriella’ bag on the coffee table and opened it up. The young woman blushed as Kelly rummaged through her things. 

Kelly: Ha-ha! There they are...

She slipped two folded Goodnite briefs out of the bag. They were white with purple sides and featured little flowers and a cartoon owl on the crotch area. Gabriella looked at her feet while her babysitter was waving her bedtime diapers around. 

She had nothing to be ashamed of in front of you though, as you were sitting on the floor wearing 2 of those same bedtime diapers, the first of which was already wet. 

Kelly handed a pair of Goodnites to Gabriella, who looked up at it with hesitation, but the eyes of someone who knew she better behave. She took it from her reluctantely.

Briana: Time to put your Pull-Ups on, baby.

Gabriella: Can I at least change in the bathroom?

Kelly: The door is locked. Besides we want to make sure you put it on correctly. Go ahead.

Humiliated, Gabriella proceeded to slowly slide down her bee-covered, thick cotton panties. Her sundress covered her privates, but the young woman was still clearly embarrassed.

She stepped out of her childish underwear and unfolded the even more babyish Goodnite brief, stretching it’s sides in the process. The crinkly, panty-shaped diaper made it’s way up her legs and under the dress. Gabriella adjusted the padded brief on her butt.

As she did, Briana picked up the training panties she had just left on the floor and threw them in your face, as you watched Gabby in awe.

Briana: What are you looking at little pervert?

Gabby’s cloth trainers landed on your face. They were still warm. Then they fell in your lap and you realized how thick the cotton was as you picked them up and pushed them away. 

Kelly: Since our little boy over here peed his little girl Pull-Ups earlier and desperately wants a change... let’s make it into a challenge. You know the ‘’Hold it’’ game? Where you can’t go to the bathroom and you have to hold your pee for as long as you can. Well this one is similar. You’re not allowed to go to the bathroom.... but the winner of this game will be the one to pee him or herself first!

Gabriella: What?!

Kelly: That’s right. The first one to pee themselves will get a fresh new diaper. The loser... will have to wear the winner’s wet diaper.

You: But... but that’s not fair... I just peed! Plus I’m wearing TWO diapers. Can I at least remove the wet one first?

Kelly: Certainly not! It’s not MY fault you had an accident. Besides Gabby showed up all dry like a big girl. It’s only fair she’d get extra points. As for the other matter... I suggest you start drinking now. 

Gabriella looked at you for an instant, then started running down the hall, towards the kitchen. You got your diapered butt up as well and ran after her.

Briana: This is gonna be fun.

In the kitchen, the young woman grabbed the first glass she could find and filled it up with water.

You: Hey! Hey... We don’t have to do this if we don’t want to you know. If we both refuse to play they can’t use us against one another.

Gabriella: I had them as babysitters before. You don’t know what they’re capable of. I do. And no offense... but I don’t want to wear your disgusting pee-soaked Pull-Ups.

You: Well I don’t want to wear yours either! 

Gabriella: Why not? You’ve already got two on.

You: Exactly! ...What do you mean by ‘’what they’re capable of?’’

Gabriella : I guess you’ll see. Now let me drink.

You grabbed your own cup and started chugging as much water as possible. It was unfortunate that you had just emptied your bladder. You had no idea when Gabby went to the bathroom last. Most likely longer ago then you did... 

You took her glass from her and spilled her water in the sink.

Gabriella: Hey! What’s wrong with you!

You: I’ve spent the last hour in a wet diaper. I’m not spending the evening in one! You just arrived, it’s your turn now!

Gabriella: Well I have been spending my last 2 weeks in Pull-Ups at night and training panties ALL DAY because of that psycho. I spent a full evening with her already, I’d say it’s YOUR turn!

She grabbed your cup and ran to the living room with it. You stayed in the kitchen and drank from the tap water. Stupid girl, you thought, there’s nothing to drink there.

You chugged two more glasses of water before you felt to full to continue. You filled a new glass and joined the girls. 

Gabriella was now drinking from the juice sippy cup you had been given to drink earlier.

When she was done, she parted her legs a little and lifted up her skirt, looking down at the owl on the front of her Pull-Ups. The two babysitters observed her with a smile from the couch. You watched as well, your mouth dropping a little from such an improbable display.

Then Gabriella closed her eyes and her face took a relaxed expression as you head the hissing of her pee filling up the Goodnite’s padding. The brief expanded and the white fabric darkened a bit. 

Briana got up from her seat and close to the young woman who was still looking, down. Ashamed, but relieved at the same time. The babysitter pressed her hand against the warm padding.

Briana: Well isn’t that a good girl! 

Gabriella: Can I take it off now?

Kelly: Of course you can. Give it to our young friend over there, he’ll put it on top of his own.

Gabriella grabbed the dry folded Goodnite lying on top of her bag to change into it.

Kelly: What are you doing? I said the winner would get a fresh diaper... not a Pull-Up.

Gabriella: What? I thought you meant....

Kelly: You have to listen to my choice of words baby. Clearly you’re not ready for big girl Pull-Ups yet. You were so eager to pee yourself in it. 

Gabriella: But... 

Kelly: Go to Jordan’s room and look in my bag. I’ve got a nice, thick diaper for you Gabby. Bring it back to me.