Male Babysitter Stories

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Babysitter Caught on Tape

by mary1000 on Sep 14, 2017
Erotic Couplings

I work from home, and had mislaid my keys for my desk so decided to check the houses security videos, to see if I had put them somewhere stupid. Sitting down to go through them my stomach did a flip when watching back last fridays tape of the kitchen, onto the screen came our babysitter, Jess, with a man I had never seen before. He looked a good few year...

In the Nick of Time

by Cat_photobuff on Sep 17, 2017
Mature

There are two sides to every story. One of my best friends on the internet, who uses the author name "Cattoy", submitted a story called "Nick's Babysitting Adventure". When you get a chance, please read it. To my dear Cattoy: please forgive me for butchering your wonderful story. You know I love you. _______________________ Damn, look at the time, I though...

My Babysitter Ch. 03

by GreenGale on Sep 11, 2017
Transsexuals & Crossdressers

Getting forced down, a big, fat cock shoved down my throat. I was choking on it, I couldn't breathe. Oh, and another one, ramming my ass. It felt so powerful, and I felt powerless. These things never last though, and before I knew it, I was awake. I opened my eyes and there was the most beautiful woman to me, Annabelle. Well, that is if you consider her a wo...

BabySitter Bingo

by Ashson on Sep 12, 2017
Erotic Couplings

It was a hot mucky night the night I had to sit for Andrea Wilson. She, lucky devil, would be sitting in an air conditioned hall playing bingo while I was sweltering at her house with just a fan. She really needs to get air conditioning. Her husband, Ron, was on a business trip and was probably relaxing in an air conditioned hotel bar with a drink in his han...

Forbidden Fruit

by FireFighter214 on Jan 22, 2009
Fetish

Your name is Simon, you?re in your late twenties and you just lost your job. Due to outsourcing, downsizing, cutbacks, economy, and a half dozen other bullshit reasons your asshole boss gave, you've been let go from the dead end cubical job you had for a couple years. Well you have to pay the rent somehow, so you check the local paper. You noticed there's an...

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Ryan Paevey: The MILF Lover

by NicoleChiTown82 on Sep 14, 2017
Celebrities & Fan Fiction

Prologue: On a hot day in Sunny California a young woman named Savannah Jade was arriving at LAX to start a new life with her 4 year old daughter. She was a beautiful woman with full luscious breasts that filled out any top or dress. Her body was the perfect blend of curves. Her breasts were a 38dd and she had a 25" waist with a 42" hip. It had been 4 ye...

Twenty-Two More Questions

by silkstockingslover on Jan 20, 2020
Reviews & Essays

Twenty-Two More Questions Summary: 22 questions asked by readers answered. NOTE: Thanks to Tex Beethoven and Robert for editing. I wrote the essay Twenty Questions in December 2017 and Twenty-one More Questions in 2018. I answered the following questions, in case you want to read them. 1. Are you really a teacher? 2. How often do you wear nylons? 3. Wh...

Male Babysitter

by JamesSD on Sep 19, 2017
Mature

"I'm worried about my boys, Marge," Gina Smith confessed to her best friend after church one day. "Why?" Marge replied. "You're a great mother, and your boys seem happy and they do ok in school, right?" "I know... maybe I'm over thinking, but I feel like they need more of a male influence in their lives. Clancy never was around that much right after the di...

Doing the Babysitter

by Stone Burke1a on Apr 29, 2012
Swinging

John was running late; the last thing he wanted was to have to pay the babysitter for staying late. It sucked that his wife had left him just when things were looking up but he consoled himself with the fact that she did not take the boy with her when she left. It was not an easy life these days but he wanted to make it work and not just for his son's sake b...

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Wild Night for a Young Man

by fantaseeboy on Jun 24, 2019
Exhibitionist & Voyeur

Sitting in Samantha's car outside of the theater, my entire body shuddered when she reached into the back seat and brought forth a plain white t-shirt and white flip-flops. She laid them on the seat between us, smiled wickedly and whispered, "Karter, you know what to do. Change into these things." She was right, I knew exactly what she had in mind. Without...