Babysitter Stockings Stories

43,783 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

The Ethical Slutmaker Ch. 10

by KrisCherita on Sep 14, 2017
Anal

Chapter 10 A Perfect Bottom Dan read through the email a second time, glad that he had a private office and could hide the tent in his pants under his desk, and wishing Andrea had tagged the text NSFW. "Dear Tammi and Dan "Robyn enjoyed babysitting for you last week, and hopes you enjoyed your evening out. She's now decided that she likes and trusts you...

Babysitter Cupcake: MILF Cuckqueaned

by silkstockingslover on Feb 26, 2019
Fetish

Summary: College girl seduces wife and then fucks husband. Note 1: I have been asked by a number of people for a couple of years to write a cuckquean story (which made me look up what cuckquean means). I had begun attempts on one a couple of times over the past couple of years, but I set them aside when the plots didn't work. Then after a few more requests...

She-Male Babysitter

by sirhugs on Sep 28, 2020
Transgender & Crossdressers

[Note to Readers: This is not a story with quick short sex scenes, so if that is your goal, it might not suit you. There are detailed sex scenes, or one long detailed sex scene, take your pick. The use of the infirmary apartment setting is an homage to John Irving's The World According to Garp, which otherwise shares nothing with this story. My thanks to Car...

Stepping Out

by Leland48 on Sep 19, 2017
Group Sex

I leave to pick up the babysitter. You are getting ready and still wrapped in a towel. I have dress pants on and one of my silk shirts. You tell me to give you 15 minutes before coming back. I drive very slowly, I arrive back at the house with the babysitter 20 minutes after I left. We walk in the house and I find you in the kitchen. You look so hot I have...

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...

Three Vignettes

by switch716 on Sep 13, 2017
Erotic Couplings

(1) She drives the better car. I made sure of that. We can afford two cars, but the better one? All her. I'll take the Audi. She can have the Merc. I don't even like Mercs. Never did and never will. She loves that status symbol, and I really don't care about that stuff at all. What I do care about, though, is her. This is a woman who, even after ten years...

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...

Male Model Nude for Money and Sex

by MotherandSonTrueConfessions on Oct 7, 2019
Exhibitionist & Voyeur

After modeling naked for women that he knew, years later, modeling nude while in college brought back fond masturbation memories. Author's Note: This is a true story about Dave, a proud crossdresser who goes by the name of Kelly when he's dressed as a woman. A submissive male with a medium build and feminine features, at 5'6" tall, when dressed in drag, mo...

Naughty New Years

by dogfood on Sep 17, 2017
Loving Wives

My wife and I are an average couple in our mid-30's. This past new years we decided to treat ourselves to a night out on the town. With two small children, we seldom have any time to ourselves. We made arrangements to go to a local hotel for New Years Eve. We paid for a room in advance so we wouldn't have to drive home late or drunk. My wife had bought a n...

The Babysitter Gets Caught

by Jay142 on Aug 8, 2018
Exhibitionist & Voyeur

Dan and Leslie had been married just over seven years when their marriage hit some bumps in the road. They both worked full time jobs, and now had two young boys. The pressure of work, marriage and children put a stress on their lives and had a similar effect on their sex lives. What was once a hot, romantic sex life with some spice of kinkiness had now turn...