College Babysitter Sex Story Stories

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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...

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...

The Worst Story Ever

by XicotencatlSmith on Sep 13, 2017
Erotic Couplings

AUTHOR'S NOTE: I've made an effort to make sure this is the worst story ever. Hackneyed, unoriginal, disjointed, etc. I apologize if any of the punctuation or usage is correct. If you chose to vote, Please give this story a one. I'd appreciate any comments about how to make this story worse (Sorry, more bad.) * * * * * Thrash Maxim pulled his monster truck...

Little Did I Know

by rwcforfun on Mar 10, 2020
Mature

(Everyone involved in sexual activity in this story is at least 18 years old and any similarity between this story and real life are a figment of your imagination.) Author's note: Sometimes it is hard to choose a category for stories. I chose "Mature" based on the beginning of the story. I hope you enjoy. *************************************** It was jus...

Vacation Time

by Specializt on Aug 9, 2019
Miscellaneous

This is a Story about You (Henry Wilson, 38), your wife (Lisa Wilson, 35), your daughter (Annabelle Wilson, 18) and her babysitter (Leyla Davis, 23) on a Vacation. You: You are Henry Wilson, a more or less succesfull, 38 Lawyer. You are not the Lawyer of the rich and beautiful, but your job pays good enough to afford everything you want. Still your lifestyle...

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Sara the Bad Babysitter

by rutger5 on Sep 12, 2017
Group Sex

Story contains coercion and reluctance. ***** Mr. and Mrs. Crudele were going to have a much needed night out. Since the arrival of their little bundle of joy four months earlier they hadn't had a night out together. In fact they rarely had a few consecutive hours sleep in a row. But that night they had plans for a quick supper followed by an evening at th...

Babysitter Rin

by Sean Renaud on Sep 12, 2017
First Time

"Hurry up Honey; we don't want to be late for the play." Kevin was standing in the doorway adjusting his tie and making a few last minute adjustments to his tuxedo. It had been a few years since the last time he'd been able to take in a musical and everybody who'd seen Wicked had simply raved about it. "Coming!" Susan appeared at the top of the stairs in h...

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...

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Not Scuba Diving

by tanglosax on Dec 19, 2018
Loving Wives

Monday evening, after dinner, at our house: "Honey, we need to talk." Are there worse words for a husband to hear? Can't be many. My first thought: what have I screwed up recently? I mean, seriously screwed up. All husbands screw up all the time, but it usually takes a fairly serious screw up for the dreaded words to come out. Anyway: "Ok, dear, now?" "Y...

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...