Babysitting Stories

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Babysitting for Swingers Pt. 01

by kaylee_2000 on Oct 5, 2020
Group Sex

It was a chilly fall night as I waved goodbye to the couple I was babysitting for as they backed out of the driveway on their way to a date with some friends. I turned around and went back inside to check on the kid that I was to take care of that evening for a couple hours. I liked babysitting to earn some extra cash to help with my Freshman year of college...

The naive and kind Chloe

by ottoka007 on Apr 29, 2025

Chloe Harper was, by all accounts, the kind of girl people noticed. At 22, she was breathtakingly beautiful, with her long, flowing blonde hair and perfectly toned body, but that was hardly the first thing her friends and family loved about her. What set Chloe apart was her heart — kind, gentle, and so naïve that she often found herself in situations that wo...

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The Babysitter

by Johnny_H on Sep 12, 2017
Erotic Couplings

Author's notes: For people who are wondering why Johnny is included in these stories, it is because this babysitter story was planned long ago. For those of you wondering if these are the same characters in every story, they are. Even a few who are mentioned only in passing will show up in future stories, and already have. Having said that, this is not gre...

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...

Gina Loses Her Virginity

by Mysteria27 on Sep 25, 2017
First Time

I've been babysitting for the longest time. Every weekend, I have a job and have made enough money to buy a car. I've been babysitting for the Jackson's for about two years now. They hired me overnight and will be paying me three hundred dollars. I'm so excited to go over there tonight. The best part of babysitting over there, is their gorgeous son named Jac...

Babysitting

by HeatherMaureen on Mar 6, 2018
Transsexuals & Crossdressers

It had been so long since I used to babysit for my sister and dress up in her things. That's where my obsession had started. Then as I got older I stopped babysitting for her. There was little chance for me to do any dressing at home and I pushed the idea to the back of my mind. One night when my little sister was already babysitting for my older sister I...

Embarrassed

by nicakwalt71 on Oct 15, 2020
Exhibitionist & Voyeur

Maria is a beautiful young woman. She is 20 years old. She has a very pretty face, with beautiful blue eyes, thin lips and has the most beautiful blonde hair. And, if her beautiful face wasn't enough, she also has a rocking body. Not very tall, skinny, with small firm tits and a nice firm butt. So you understand, she is a goddess. And to counter that, she co...

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Annie Babysits the Kids Ch. 02

by DocCIS on Sep 26, 2017
Group Sex

Chapter 2...The Second Cumming In Part One I told of watching my fiancé Anne-Marie blackmailed (?) into having sex by the guys she used to date as teenagers and how aroused and excited it made me (and from her actions, her as well). The adventure continues... ******************** I did not mention to Annie what I saw happen Friday night, waiting to see wh...

My best friend's sister, the babysitter

by darkwindofchaos on Aug 7, 2008
Erotic Couplings

Hi. My name's Aaron Silversten, and when I say I have a story to tell, I’m not kidding. You see, when I was in high school, my friend Jarod had this younger sister. Well, she's still his younger sister, only she's not so young anymore. Allow me to explain. When first I knew Allison, she was fourteen when I was eighteen, but boy, even then, she had a killer b...

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Reward for a nice babysitting

by Suzanne_hot on Mar 3, 2010
Swinging

Suzanne is a nice looking girl of 19 years old. 5'5'' with a body perhaps a bit thinner than the average, she is cute. Her tanned skinned is higlighted by two clear blue eyes. She wears her dark hair long and often tied in ponytail. She's got a piercing at her navel and a little rose-shaped tatoo at the bottom of her back, but she's not otherwise really auda...

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