Male Babysitter Stories

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The Babysitter Threesome

by NewWriter1 on Sep 3, 2017
Fetish

We arrived home earlier than expected, and Jessica, who had just turned 18 last month, had already put our daughter to bed. We had already informed Jessica that this particular babysitting job would be an overnight one and we intended to keep that promise. In addition, we made plans while on our date for other things to occur as well. I told Jessica to stri...

Mr. Jackson Marks Marie

by SexySpanker on Sep 18, 2017
BDSM

Marie was frustrated. Once again her boyfriend Shawn had failed to satisfy her. After some gentle foreplay followed by a few minutes of slow, passionless penetration, he'd collapsed beside her, then snuggled up close and fallen promptly asleep. Marie, of course, was just getting started. She silently teased her clit as her boyfriend snoozed next to her, br...

Koko Gets The Job Done

by buffaloraven on Sep 16, 2017
Group Sex

I hadn't known Koko that long, but that's the glory of a university town: plenty of new faces all the time, and lots of them hard up for money, and with the spare time to earn some. And I'm not talking about sex, pervs. Well, at least not PAID sex. But we'll get to that later. As I was saying, Koko had moved in up the street from me earlier that summer wit...

The Transplant Ch. 03

by thrillerauthor on Dec 15, 2017
Transsexuals & Crossdressers

© 2017 by Thrillerauthor I was so nervous it took me three tries to get my eyeliner straight! Was it like this for every girl before her first date? I still couldn't quite believe that I was going out to dinner with Dr. Richardson. Paul, I corrected myself. His telephone call late one afternoon came when I was in the middle of fixing dinner for my daughter...

Having a Babysitter Ch. 03

by mattchat33 on Sep 12, 2017
Mature

The next few days I thought about Sarah more and more, remembering the wonderful time I had with her the last time I drove her home from our house after babysitting. I kept on wondering whether I would be able to spend some more time with her and hopefully have even more fun with her. However there wasn't any opportunity for my wife and me to use a babysitt...

Adventures in babysitting

by Ashley16 on Feb 18, 2017
Exhibitionist & Voyeur

Summer, an incredible time of year. Exams were over, the school year was coming to an end and all that was on anyone's mind was parties, gossip and sex. I was no exception. I'd lost my virginity last year at my friends house party, while half the party listened from outside the door. This earned me quite a reputation, first as a slut ready to fuck half the s...

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Maximillian Mazan's Marvellous Machine

by chriscole on Mar 17, 2015
Miscellaneous

Author's Note: Feel free to create your own fantasies with whomever you wish. Please do not continue someone else's specific stories. However, you may start a story with the same character(s) someone else already has a story for. The POV (you) can be male or female. The default POV in the intro is male, but the machine can change that. You don't have to foll...

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Becoming Julie's Governess Ch. 06

by susangreenway on Jul 29, 2019
Fetish

[This story will make more sense to you if you read the first five chapters. However, it can also stand on its own. It does contain a good deal of activity relating to bodily functions and some spanking and discipline, so if these are not things you like to see, read no further. All characters are over 18.] ***** While Lesley enjoyed becoming her mother's...

Who Loves Ya', Baby(sitter) Ch. 02

by HarveyMarcus on Sep 12, 2017
Erotic Couplings

WARNING: The following story is for the entertainment of ADULTS ONLY, and contains descriptions of explicit sex. If you are not an adult, or reading sex stories upset you, or you are offended by subjects of a sexual nature - do not read any further! This story is for entertainment only. It contains adult oriented material. This is a work of fiction. The a...

Bangin' The Babysitter

by TheSandyRavage on Dec 14, 2020
Erotic Couplings

The temperature was humid, the air thick, and the sun bright, which only made Mike's mood worse. He was sweating and cursing under his breath. The babysitter had just canceled on him. He ran his hand through his beard, trying to figure out the right move here. His wife was visiting family and he was stuck with their 5-year-old, but he'd had plans to stop by...