Sissy Babysitter Stories

9,467 results
Orientation
Length
Source
Infinite Scroll

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...

Bad Babysitter Ch. 02

by thisgirlistrouble on Sep 25, 2017
Erotic Couplings

Weeks later his wife found out about his affair with their babysitter. But to his surprise, she didn't react the way he imagined. As was routine, Kim arrived at their house with their kids after school. His wife had arranged for them to be picked up at 3:45 by a family friend but hadn't notified Kim. When the three girls walked inside, she told the girls t...

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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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

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 Hot Babysitter Ch. 02: The Gift of Love

by Syzoth on Mar 26, 2019
Romance

This series run parallel to the "Sharing My Wife Amanda" storyline. This particular work follows "The Hot Babysitter Chapter 1" as well as "Sharing My Wife Amanda Chapter 14". Thanks to lovemesomephilly for the awesome inspiration. Author's note: this story could've been listed under the "Group Sex" category, but was submitted under "Romance" for reasons...

I'm in love with the babysitter

by domingo on Apr 12, 2020
Amateur

Your wife is out of town for a business trip for a few days and you had a last minute work event this evening you couldn't get out of. Luckily your babysitter was also available for this evening as well at such short notice. Everything went smoothly this evening and feeling good about your work you are able to head home around 9 pm. This is almost two hours...

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Begging for a Pegging

by Cirkle7 on Oct 12, 2020
Fetish

I'd like to first apologize for my extended absence! I became frustrated by anonymous critics who would pick my stories apart. So if this story is in no way interesting to you, please do not read all of it and then anonymously comment on how bad you thought it was.. I appreciate feedback and criticism but if I do not know the source then how could I trust it...

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...

Clara the Babysitter Ch. 01

by jamiestory on Sep 12, 2017
Fetish

Jim and Karen got home early from evening. The party wasn't nearly as exciting as they had hoped. They thought about staying out longer, but they were hoping to get home for some alone time. It had been a couple weeks since they were able to have sex, and they found that spending the time together was working them both up, even if it was a boring work party...