Spanking Babysitter Stories

25,290 results
Orientation
Length
Source
Infinite Scroll

Babysitting the Babysitter

by humantouch on Sep 16, 2017
Group Sex

"I have never been so embarrassed in all my life," Susan uttered. "Sorry," Charlie said, "It just happened." "Farting so loud that everybody in the room stops talking just happens?" she mocked. "I had those burritos," Charlie said, "I've never done that before. Give me a break." "If it's not one thing it's another with you," Susan said, "Those were impor...

Cosplayer babysitter

by Striker137 on Apr 13, 2018
Fan Fiction

You're sitting in class paying close attention to the clock as it ticks down to the final bell. You were just seconds away from becoming free from High school. Everyone else in the classroom now seemed to be doing the same thing you were doing as you start to hear the class shout 10! 9! 8! 7! 6! 5! 4! 3! 2! 1! RIIINNNGGG! The entire class of seniors stands u...

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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...

The Christmas Babysitter

by BadLilKitty on Dec 23, 2019
Erotic Couplings

When Tom came home from work one evening his wife Kathy was waiting for him with a very special surprise in store for her husband. They had been married for 10 wonderful years, had a couple of kids, and were very happy together. There was nothing they didn't tell each other and there were no secrets between them, well... almost no secrets. You see, Kathy had...

The Hot Babysitter Ch. 04 - Circle of Love

by Syzoth on Jan 22, 2020
Romance

Author's note: This series runs parallel to the "Sharing My Wife Amanda" storyline. Chapter 4 could've been posted in "Group Sex", but I placed it here because it's a "Romance" story at heart. ********** Time stands still for no one. It was hard to fathom that my beautiful wife Amanda and I were celebrating over 10 years of marriage and that our son Ja...

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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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...