Babysitting Stories

2,018 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

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...

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...

Open in Reader

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...

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...

Open in Reader

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...

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...

True Life Swinging Experiences

by trev999 on Oct 18, 2002
Swinging

This is intended to be a collection of Threads that represent real life experiences whilst on the swinging scene. Once approved the threads added will be the individual experiences to date.What's next? Nude Cleaning Service The joys of babysitting. Massage parlour heaven. The girls next door! What's next? Nude Cleaning Service The joys of babysitting. Ma...

Open in Reader

High School Whore Ch. 04

by hg33 on Sep 25, 2017
First Time

Nicole turned the key in her front door as slowly as possible, cringing as the dead bolt lock clunked into the unlocked position. Pushing gently she leaned in to the door and opened it cautiously, making almost no noise. Seeing only a faint light, she tiptoed to the stairs to head up to her room. "You were out late," she heard from behind her. "DAMN!" she...