Male Babysitter Stories

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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...

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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Jenny, Jenny

by Nuttnon on Sep 16, 2017
Exhibitionist & Voyeur

My family and I live in a nice little three bedroom house, built during our town's post-WWII housing boom. Long before Karen and I bought it the basement was finished off as a separate apartment, so we rent it out. If you've ever owned a rental property you already know that it's bad enough to have a deadbeat tenant at all, much less one living right under...

Hiking with Friends

by Ashson on Sep 13, 2017
Erotic Couplings

There was a group of us, three women and two men, and we were going hiking in the mountains. There was me, I'm Bob, Carl, Josie, Mary and Angelique, the last being known as Ange. Carl and Ange were currently going steady while the other two girls and I were footloose and fancy free. We were young, our average age being around nineteen, fit, and ripe for a li...

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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Babysitter Auditions Pt. 04: Melody

by TitManDDo on Dec 14, 2020
Interracial Love

My fourth interview had been with Melody Sato. Melody was a stunning 20-year-old Japanese woman with long wavy brown hair and flawless tawny skin. She was slender, flat-chested but with a tight little round ass, and maybe 5'5"; she looked like a runner, which she was. She was reserved, soft-spoken, and impressively poised. When I gave her the rundown I had g...

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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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...