Sex For Babysitting Sex Story Stories

367,493 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 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...

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...

Doin' the Boss: Babysitting

by RobynG on Sep 15, 2017
Mature

This is the third installment of my on and off affair with my now former boss. We worked together for two years before I ended my affair with the man 12 years my elder, only to rekindle our relationship over the Christmas holiday. For those of you who have written nice feedback, THANKS! For those who insist that I am a loose morals slut, you are entitled to...

The Perils of Lisa

by Shandy on Dec 20, 2015
BDSM

Due to some requests, a picture file has been added here https://chyoa.com/chapter/Pictures.464992 additional pictures will be added over time. Your name is Lisa Carter. You're an extremely attractive young woman, twenty-three years old, working your way through college. You're about 5' 5", very curvy, with full ripe breasts and firm shapely thighs. You...

Open in Reader

Hullabaloo Party

by Winterfrog on Sep 14, 2017
Loving Wives

I work for one of those multinational consulting companies as an accountant in a Scandinavian county capital. Most people think that to be an accountant is a terrible boring job but I must say they're wrong. I met a lovely girl during a job and got engaged to her. When this story begins I was a single guy at the age of 26, friend with many girls but had not...

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...

Jenny's Diary: Babysitting Incident

by GoodEater on Sep 13, 2017
Toys & Masturbation

Dear Diary: This is something that I never thought in a million years I would admit, but what the hell. I am older now and this was many years ago. Since then I have lost many of my inhibitions and have decided I don't care what people think. I remember it being a snowy night and I was babysitting for a neighbor. They were a nice couple who went out about...

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...

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...

Megan's Milk and More Ch. 02

by GusBus77 on Sep 18, 2017
Fetish

*** Disclaimer: The events portrayed and actions in this story are purely fiction. Characters however, may be inspired from the reality of the author's life. All erotica and sexual fantasies are once more, just fantasies for the pleasure of the reader. Enjoy!*** * Megan was dying of boredom in the living room. She swore she watched the same SportsCenter ab...