My Babysitter Stories

336,266 results
Orientation
Length
Source
Infinite Scroll

Bribing the Babysitter

by Mister_Shy on Aug 21, 2018
Mature

Chapter 1 It had been two months since Jenni had first let Mr. Taylor masturbate on her. It was becoming a bad habit. Mr. Taylor didn't make a mess on her thighs every week. Jenni typically babysat for the Taylors on Tuesdays and Thursdays when no one would be home until late, and on the occasions that Mrs. Taylor drove her, the nights went by uneventfully...

The Ethical Slutmaker Ch. 10

by KrisCherita on Sep 14, 2017
Anal

Chapter 10 A Perfect Bottom Dan read through the email a second time, glad that he had a private office and could hide the tent in his pants under his desk, and wishing Andrea had tagged the text NSFW. "Dear Tammi and Dan "Robyn enjoyed babysitting for you last week, and hopes you enjoyed your evening out. She's now decided that she likes and trusts you...

Blissful Ignorance

by sindermann on Mar 31, 2017
Miscellaneous

For most people, familiarity inevitably leads to a blissful ignorance of what the other party is doing. The husband fails to notice as his wife bats her eyes at the stranger in the restaurant, the wife begins to ignore the overtures her husband is making toward the cute babysitter, and the father trusts his friends not to be forward with his offspring. Somet...

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A Visit By Renee, At The Local Bar

by stoneypoint on Sep 14, 2017
Romance

Renee's husband stopped over Saturday afternoon to invite me for a drink at Jets Bar and Grill. My first thought was to decline his offer, but I have already done that three times to him, so I accepted. I kept thinking about that one day Renee stopped over and we cuddled on my bed after she read two stories I had written about her and I. All I could think...

The Director and the Babysitter

by dramatic1 on Sep 14, 2017
Mature

I wouldn't have fucked the hell out of our babysitter if she didn't belong to my gym. See, our babysitter, Stacia, has always been what I would consider "cute." She wears baggy clothes, even in summer, and so I never really got to see her body. Our kids loved her to death. She would come over, my wife dealt with her most of the time, and I just paid her at...

The Babysitter

by Lonedaddy on Sep 18, 2017
First Time

My wife and I live in the valley, just outside of the city. We thought it would be a nice place for a younger couple to raise a family. We bought a two story house with an attached garage. It needed a few minor cosmetic repairs, but nothing major. After some paint and building a new deck out back, it looked really nice. My wife Rose, is the manager of one...

Sara the Bad Babysitter

by rutger5 on Sep 12, 2017
Group Sex

Story contains coercion and reluctance. ***** Mr. and Mrs. Crudele were going to have a much needed night out. Since the arrival of their little bundle of joy four months earlier they hadn't had a night out together. In fact they rarely had a few consecutive hours sleep in a row. But that night they had plans for a quick supper followed by an evening at th...

The Babysitter

by Purple_Rose90 on Sep 28, 2020
Erotic Couplings

After three knocks, the front door swung open. I was surprised to see an incredibly striking man in his late 40s on the other side of the door. I couldn't decide which I found more attractive: his piercing green eyes or full head of dark hair with a grey hint. "Mr. Anderson?" I asked. "Yes, you must be Arielle?" I nodded in confirmation. "Yes, I am. Nic...

Don't Cum in the Babysitter

by Imyourdaddy2nite on Jan 22, 2019
Erotic Couplings

My wife and I were college sweethearts that met our junior year. We took an instant liking to each other and the sexual chemistry was amazing. We had a lot of the same values and morals, but didn't agree with each other on everything, but we could both argue our viewpoints and then agree to disagree. I'm not going to lie; the sex after the more spirited deba...

Mrs Andrews Disposes Ch. 03

by lesliejones on Sep 17, 2017
BDSM

Ch. 03—Friday Night Readers will find themselves better equipped to enjoy this story if they have read the first two chapters. This story sometimes deals with bathroom behavior so those offended by that should move on. All characters are 18 or over. By Friday evening, Charlotte Byers had assumed total control over the lives of Karen and Andrea Andrews du...