The Dare, And The Risk He Took (Private with BabyAsh (Ashley))

[Skylove27]

James is a college student, a junior majoring in music. He usually had classes in the middle of the week and he studied on the weekends usually the only time he could really hang out with friends was on a Friday night. And that Friday night the played Truth or Dare just for fun. James was the risky type of person he wasn't afraid to really try anything new. But this one dare made him question it. He had to be babysat for a whole day and night, and they got to pick his babysitter and plan it.

[Baby Ash(Ashley)]

Anna had just graduated high school and moved to college, now she didn't start for a few months because she wanted to start at a different semester. But with so much free time on her hand, she wanted to find something to pass the time. Now Anna was a girl who was on the taller and curvier size, she had matured early on in life and her chest finally seemed to stop growing. In fact she had trouble looking down at her feet sometimes because her chest was so large. An even though Anna did get a lot of stares from men, her style was very different from your typical girl. She was a little goth which turned some men away and she always like things that were strange or unusual. It was safe to say that she would look on Craigslist for odd or unusual jobs, one ad stood out that was in the adult section. The ad said a babysitting job for a larger baby, she was intrigued so she contacted the ad owner. They talked for awhile and she laughed a bit with the idea of her babysitting a kid in college, even though this was something up her alley.

[Skylove27]

James looked up at the taller woman in front of him. He was really curious on what made her want to babysit a man in college. He nodded. "Yeah I guess. I'm James. Come in. Don't tell me that diaper bag is meant for me?" James asks.. though he figured the answer.

[Baby Ash(Ashley)]

Anna rolled her eyes a bit at James, "Well this diaper bag isn't for me is it?" Anna said as she looked around James place. After James showed her the Guest room she looked around and noticed it wasn't that big. "Hmmmm, ya I don't think I will be sleeping here tonight Jamesy. Take me to your room, I think I'll setup my stuff there." Anna said flipping her hair back, which showed her breasts a little more.

After James stopped looking at her chest they both walked to his room. Not only was it bigger, but it had it's own bathroom and tv. "Ya I think this will be my room and YOU will get the guest room." Anna said as she placed the diaper bag on the ground. "But first things first, strip and get on the bed so we can get things going." Anna said pulling out baby clothes that were in his size. She saw there were diapers too, but those would be for later.

[Skylove27]

(he's not gonna be diapered right away, right?)

[Skylove27]

James frowned and showed her his bedroom. Which indeed was much bigger. "But this is my room. And it has my clothes and stuff." James says.

"I'm not stripping if you're putting me in that." James crossed his arms

[Baby Ash(Ashley)]

Anna signed and said, "look honey, I was told to put you in these clothes one way or another. I am your babysitter and I am taking care of you. Besides you took the dare, now be a Gud widdle boy and do as your told." She leaned over exposing even of her chest, she knew guys couldn't resist. Am to be honest she really enjoyed the idea of humiliating this guy and making him helpless like a baby.

[Skylove27]

James couldn't deny that he took the dare, otherwise she wouldn't be there. "Alright, alright. I'll wear the clothes." James says, starting too take his clothes off. "Can I atleast keep my boxers on?"

[Baby Ash(Ashley)]

Anna shrugged her shoulders and said, "ya I don't see why not, your friends just told me to make you wear the outfit. Although, if for any reason I feel like it or if a "big boy" like you has an accident, there are always these." She pulled the diapers out of the bag. They had cute prints of cartoons on it and were easily his size.

[Skylove27]

"There won't be any need... I can get to the bathroom on time. I'm good with my boxers." James says. He wondered what he'd be wearing.

[Baby Ash(Ashley)]

Sara had a few outfits to choose from, she was really surprised at the clothes his friends got for him, it was kinda like they had been waiting for this or something. She decided to go with the ducky printed shirt and short shorts. "Look at this adorable outfit jamesy, you will like so cute in this. Now ask your mommy if you can be dressed." Anna said thinking adding the mommy part would get her in the right mindset.

[Skylove27]

"Look Anna, you're not my mommy. You're my babysitter. So I'm not gonna call you mommy. Can you just dress me already please?" James asks a little impatient.

[Baby Ash(Ashley)]

Anna giggled and said, "whatever you say shnoockems. But you better watch your mouth or I'll give you a spanking!" She then proceeded to put the shirt over his head, which was a tight fit but made him look even more childish. She then bent down and said, "alright now put your legs

[Skylove27]

The shirt just barely reached his waist. It was hallway between his waist and under his belly button.

[Baby Ash(Ashley)]

Anna got his first leg in but when she put the other one on it was a bit of a struggle. Though

[Skylove27]

James fell forward and his hands fell down to her boobs. He leg was finally through the leg whole of the shorts and they were pulled up. So it made him look like he

[Baby Ash(Ashley)]

It took Anna a sec to grasp the

[Skylove27]

It took a sec for James to react what was going on. "Hey I said I was sorry! Hey that hurts!" James yelled as his bottom was smacked. "I'm not filthy!"

[Baby Ash(Ashley)]

After Anna was done with the spankings, she

[Skylove27]

James was crying softly as his bottom stung. "I'm sorry. It won't Happen again." He says. He sniffled softly

[Baby Ash(Ashley)]

Anna pulled back a bit, "good." She said as she reached into the diaper bag for something else. It took her a minute but she pulled out a pacifier, "here this might make you feel better." She said while giving me a small pat on top of his head.

[Skylove27]

"No. I don't want that." James says. He moved his head away from the pacifier

[Baby Ash(Ashley)]

Anna took a deep breath to calm down and then she said, "remember buddy boy, a dares a dare. Besides I don't think you want another spanking do you?" She then held the pacifier to his face, waiting for him to take it.

[Skylove27]

James looked at her with teary eyes and shook his head quickly. He opened his mouth.

[Baby Ash(Ashley)]

Anna plopped the pacifier in his mouth and patted his head saying, "such a good little boy. Now let's go downstairs, I'm hungry."