Literotica Virgin Babysitter Stories

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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...

The Hot Babysitter

by HornyKid45 on Jul 13, 2019
Amateur

(It is implied that all characters in the story are atleast 18, and at no point am I implying that any characters are under 18) https://youtu.be/zNtBUerpNcE ======================================= It was hot Saturday night in the fall, and your parents wanted to go out on a nice date. They wanted to get dinner and then go watch a show in the city, which mean...

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An Unprepared Sitter

by WordWizard55 on Sep 25, 2017
Group Sex

"I just don't have the sexual drive that you still do anymore. Not that I could ever match that anyway." I stared at my wife from across the table at the nice restaurant we were currently dining at for our 20th anniversary. The conversation had taken a slight turn from where it had started, that was for sure. "I know honey, and that's fine. Hell, I wish...

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...

Slutty Sitter

by Milane on Jan 24, 2018
Amateur

Your Eighteen and your names Brayden. 6'6 ft in height, black, very well built, and have a huge dick (Shower not grower). Its 16 inches long 2.8 inchs thick, equipped with fat heavy sized grapefruit testicles. No one knows about the enormous pussy wrecking monster cock you keep in your pants, not even your parents or doctor. Your still a virgin and are about...

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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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Anal Punishment for Cheating Lovers

by libidinal on Sep 12, 2017
Anal

I had been waiting at the airport for hours when I finally heard the announcement that my flight had been cancelled and there wouldn't be another one until the next day. I was going to visit my sister in California but now my departure would have to wait until tomorrow. So I headed to the parking garage for my car and headed home. When I opened the front d...

Vacation

by MetropolitanDenial on Dec 6, 2017
Erotic Couplings

Rose and Owen Harper saved up all year for their big family vacation. This year, they'd be taking their four children - 20-year-old Dean, 18-year-old Finn, and 15-year-old twins Lucy and Lily - to Florida. They were thrilled at the idea of taking the kids to the central Florida theme parks, spending time at the beach, and, most importantly, having some roman...

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The Babysitter

by aksarben on Sep 13, 2017
Group Sex

So, there we were, just a couple days after St. Patrick's Day near in Topeka, Kansas, a few years back, when I was married. I have since divorced, but, the story needed to be told! My wife and I were sitting at home when there was a message on my phone: "If I come over would it be weird?" I replied "what would be weird?" My messaging went off again, "I...

Innocence Lost

by Reardon1 on Sep 12, 2017
First Time

Author's Note: If you're looking for a quick fix, this might fit the bill. I've been thinking about doing a babysitter story for a while; this is my attempt. * * * * Nathan Holbrook finally pulled out of the parking lot to his real estate office after a long, productive day. He had thought he would be longer but the showings he had scheduled went quicker...