Diaper Gamble (Chapter 1) (Patreon)

Chapter 1 = A Bet’s a Bet: Sarah thought that the next time someone wanted to make a bet with her, she thought she should probably just say no. If she had done that in the first place, she wouldn’t be in the position she was in right now. Her maturity certainly didn’t help her. Or the fact that people were always calling her adorable and cute just because of her size. She always tried to act mature but it usually didn’t go very well for her. She somehow always found a way to trip over her own feet or become very bratty whenever she was having an argument. Her maturity level took a nosedive though the day she went out with her friend Dave.

It had all started when her best friend Dave and she had decided to take a trip to the zoo together. Sarah had been waiting for the trip for a long long time. She loved the zoo! This wouldn’t be a normal trip to the zoo though. Ya see, Dave and Sarah had been best friends for a while and they quickly realized one more unusual thing that they had in common. They both loved to make bets. They couldn’t tell you if it was the rush of having to do something embarrassing or the excitement of watching someone else embarrass themselves, but something about making bets or dares with each other had become a source of much amusement between the pair.

For this trip to the zoo they had decided that whoever won their current bet would get to choose the entirety of the outfit that the other person would wear to the zoo.

“You’re gonna be so cute.” Sarah teased. “Maybe I’ll even make you wear a cute little skirt of something. Wouldn’t that be fun?”

“It won’t be because you’re not gonna win, I will.” Dave said.

Sarah let out a little snort and rolled her eyes. “Oh yeah right. I have this bet in the bag, just you wait and see.” Sarah giggled at him before sticking her tongue out.

The two of them had bet that whoever got a higher grade on their Intermediate Biology test would be the winner. Today was the day that they got their grades. Sarah had done her best to study for it, she really did! She had been studying for almost 20 minutes though when she got a text from Dave telling her that a new episode of Teen Titans Go! was starting. Long story short, she hadn’t studied much that night.

Sarah gasped as she stared down at the big B- on her paper. She looked over at Dave who had already seen her paper. He smiled at her as he held up an A. She had lost the bet after all!

Back at Sarah’s house the girl had tried teasing her way out of going through with the bet. “Oh come on Dave,” She said. “You’re not actually gonna make me do this are you? How about... I just give you $15 or... oh! I could even give you a little kiss.” She snickered as she puckered her lips and tried to subtly push up her boobs.

Dave chuckled and shook his head. “Sorry Sarah, a bet’s a bet. You’re not getting out of this that easily. Besides, I already know exactly what you’re going to be wearing.”

To Sarah’s surprise Dave pulled out a big bag that appeared to be full of clothing. She had assumed that he was just gonna pick something slutty from her closet, but he had brought his own stuff. She thought this was a little weird. What could he have brought for her?

“Well when we created this bet you really were acting like a little child, so after a little thought I decided that it would only be fitting if you were to dress exactly the way that you were acting.”

Sarah watched as Dave pulled a weird poofy white thing out of the bag and started unfolding it. It was so big that it almost looked like a pair of white short shorts but there was something very strange about it. As Dave unfolded the thing it made a lot of noise, crinkly plastic. There was a cute design on the front of it. A heart, a star, a flower, and more!

“What is that thing?” Sarah found herself saying.

“It’s a garment that’s just perfect for a girl like you cutie. Now put it on!” Dave handed her the garment and turned away from her to give her some privacy. Sarah took off her pants and undies before unfolding the thing even more.

“Is... is this a diaper?” She said in shock as it suddenly hit her.

“No arguing Sarah. You made a bet. Put it on, now.” Sarah thought about just ripping the thing up, but Dave was right. She had made a bet. A deal was a deal. At least no one but Dave would ever know she had worn a diaper for a bet. It certainly wouldn’t help her image. If people didn’t take her seriously as an adult now, no one was gonna take her seriously in a diaper.

It took a bit of time for her to figure out how the straps on the thing worked but she finally got it on strapped up. “This feels so fuckin weird.” She mumbled once she had gotten in it completely. The 21 year old girl stood there miserably in just the poofy white diaper and a little pink bra. Dave turned around and gasped as he looked at her.

“Oh my gosh, you look so cute!” He chuckled as Sarah hit him on the arm. “No, I’m serious. I think this really suits you sweetie.” Sarah frowned at him which only made him laugh more. “Come on hon, the zoo is gonna open soon. We gotta finish getting you dressed.”

*****

Sarah was horrified by all the clothes that came to follow. The clothes that Dave had picked out for her looked like something that her 5 year old sister might wear. After he double checked that she’d put the diaper on correctly Dave gave her a very childish shirt to wear. It was a plain white and pink striped shirt but the part that made Sarah cringe was the sewn in pink color and puffy sleeves. Once she was in that Dave pulled a cutsie denim overall dress with pink frills along the edges and a mermaid on the front over her head. He slipped pink socks with frills on the angles up her feet, which were followed up by pink and white Velcro shoes that would light up every time she took a step. Sarah sat there humiliated as Dave finished off his masterpiece by tying her hair into two cute pigtails with pink bows. Sarah could barely recognize herself in the mirror. Without any makeup on, she actually looked like the little kid people were always assuming she was. The poofiness that was threatening to poke out of the ends of her denim dress was her making her feel any better about that either.

Dave was watching her come to terms with her own reflection. He always knew that she’d look adorable in a diaper. He just hadn’t found the right opportunity to get her into one until now. He was going to savor this day for as long as he could; and he would be sure to get as many pictures as possible.

“Okay Sarah, you ready?”

“Ready for what?”

“Time for the zoo little girl.”

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This story was written by Zander Chesney
You can find more of his content here :
https://zanderchesneyoriginals.tumblr.com/