Babysit Stories

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That Fateful Weekend Ch. 11

by RecHiker on Sep 13, 2017
Exhibitionist & Voyeur

Please read the previous chapters to this story so you will know what everyone has been up to. This story is long and has many true facts about one family's life and lifestyle. The names of the characters have been changed to protect the persons involved. This story was written to entertain and reinforce the ideal that during our lifetime we make choices a...

Babysitter Challenge

by CopyCat13 on Sep 14, 2017
Exhibitionist & Voyeur

Some girls just need a little kink in their lives and Amy is one of them. For the last couple of weeks she's been going to an online chat room and getting naughty challenges from online strangers. Most of them have been either really tame like going commando or else way too extreme like getting "Sperm Bank" tattooed across her face. But every once in a while...

babysitters Revenge Backfires

by gslife on Apr 5, 2021
Fetish

Jeana lies down on her bed flustered while scrolling through her Instagram feed, trying to get her mind of her coming week. Thanks to her loving mother, Jeana now was forced to babysit a little twerp named David; for an entire fortnight. Jeana scrolls from picture to picture looking at all the fun she could be having over Her summer holiday. Not to mention t...

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Adventures in Babysitting

by TallNavyMan on Sep 17, 2017
First Time

This is my third true story. Please email me your comments. One was about a black woman, one was about a black man, and this one is about a white woman. * When I was 19 years old, I used to babysit for extra money. People thought I was crazy, but I thought it was the perfect way to make money. You can sit around and watch television, usually eat pizza and...

Becoming Cassie Ch. 01

by TGJamie on Sep 25, 2017
Transsexuals & Crossdressers

Money was hard to come by in our household. Being the oldest of four and my mom being a single mom put a real strain on our resources. Rarely did we ever have any extra money in our family to spend on things like eating out at a restaurant or going to the movies. If we wanted to do that, we had to save our own money to do it. Things were just tight. That sai...

One Last Summer Pt. 01

by SophButtons on Dec 2, 2019
Toys & Masturbation

Ellen thought about her friends a lot the summer before she went away to college. Andrea and Hannah had gone backpacking together round India. Lauren was on a cruise with her family. Alice had got a dream internship. But Ellen was doing tutoring and babysitting, working as much as possible to make some money before she went away. She was good at it, always h...

Neighborhood MILF

by DirtyDoc79 on Jun 1, 2016
MILF

Samantha Michaels has always been the the fantasy of all of the boys on our block. I remember the day she and her husband moved in to the house right across the street. I was eight at the time, and probably cared more about playing GI Joe's than ogling the neighbors. But even for a young boy it was hard not to notice how wonderfully curvy that Mrs. Michaels...

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College Shemale babysitter

by tomf15 on Sep 15, 2017
Transsexuals & Crossdressers

Disclaimer: All characters are 18 and over. Jessica pulled up in front of a large house at the end of the street. She looked down at the text; 1278 Backstreet. "This is the right place," she thought. Jessica was a fairly normal, attractive college girl. She studied hard, partied on weekends, and liked to work out. There was one thing that separated her f...

Ashley's Mix-up

by KittyFlower on Sep 12, 2017
First Time

Ashley was young but she was old enough to make her own choices. Even though she was twenty years old she still lived at home. Her parents required her to pay rent out of her regular job, however they never made her pay with the money she would get from babysitting. She was trying to get more babysitting jobs because of it. Her boyfriend on the other hand wa...

Babysitter's Fantasy Comes True

by HorneyDevil69 on Sep 13, 2017
First Time

After my wife died I was left with 2 young children. I spent as much time with them as I could, but my job sometimes required that I have dinner, or spend an evening with a client. On these occasions I rely on the neighbour's 18 year old daughter Katie to babysit for me. Katie is a beautiful young woman, but she is a good friend of the family and I never tho...