Teen Babysitter Stories

13,164 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...

Trouble Maker Ch. 02

by FreeTheDancingLlamas on Dec 30, 2019
Romance

Chapter 2: Motherfucking Badass Note: Thanks for all the support for the first chapter! All feedback is appreciated. Still a slow burn, I'm afraid. But I'm hoping it will be worth it in the end! Let me know what you think of this chapter? ———— It's day four of my purgatory known as suspension from school and Will Decker, detective extraordinaire, is in...

Babysitter Auditions Pt. 03: Autumn

by TitManDDo on Dec 14, 2020
Erotic Couplings

I woke up the next morning thinking about Carolina. She had said she'd been fired from a babysitting job, and I definitely wanted to know about that. I only had the preliminary information on her, so the firm I was using to check out my applicants was still at work. I texted the friend who owned and ran the firm to see what he knew. He told me he didn't know...

An After School Special

by abbeynormal on Sep 26, 2017
BDSM

When I was first handed this scenario, I didn't think about doing a prequel to Teacher's Pet, Chpt. 1. In fact, I had never planned a prequel. I was planning a sequel (and still am) but I saw in this a way to explain how Ron's spanking fetish first began and decided to run with it. If you haven't read Teacher's Pet yet don't worry. You don't need to before y...

After the Reunion Ch. 03

by robertl on Mar 13, 2018
Loving Wives

I awoke Sunday morning knowing, hoping, that my wife was still horny from the night before. I knew she hadn't really been satisfied and I wanted her still that way when she had her business meeting Monday evening. To that end, even though I wanted to, I didn't make love with her that morning. I planned on no more sex before Monday night. We had a busy day p...

The Babysitter & The Waterbed

by RetroFan on Sep 13, 2017
Erotic Couplings

INTRODUCTION & DISCLAIMER - Let's travel back to 1992, where 18-year-old high school senior Sabrina, a responsible babysitter for a yuppie couple, receives an unexpected visit from her boyfriend Scott, and things get very interesting. As with all my stories, this is set in the past, and will no doubt bring back memories for readers who graduated high school...

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...

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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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...