Babysitter Threesome Stories

21,270 results
Orientation
Length
Source
Infinite Scroll

My Wife & The Ebony Goddess

by CAPervert on Sep 12, 2017
Interracial Love

It was by far the happiest day of my adult life. It all began when my wife whom everyone says looks like Florence Henderson confessed to me that she had the hots for our next-door-neighbor. The 18 year old daughter of the only black family in our neighborhood who was our babysitter. The young woman's name was Diana and although my wife said she looked li...

Babysitter Revisited Ch. 02

by johnnieblue44 on Sep 13, 2017
Mature

A continuation of Babysitter Revisited. You are cordially encouraged to read the inaugural chapter before embarking on this journey. You will be glad you did. * It didn't take long for Allison and I to devise our plan for the following evening. She asked a few questions about the older executive, and Ally's intuitions were spot-on. Despite being physic...

Realizing a Fantasy

by Jerrycurious on Sep 17, 2017
Loving Wives

This is the second story that I have written for Literotica that is absolutely 100% true. I have hesitated for some time to write this, there are some very personal admissions on my part in the story. My wife has no idea that I have done this though she knows that I write here. I haven't included her name so she wouldn't have anything to worry about anyway....

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...

Getting Into The Swing Of It

by milfocker on Sep 12, 2017
Loving Wives

I was at work when I got a text from one of my wife's friends, we had recently moved out of London to the same country town as them and had seen a lot of each other recently, it said: 'Could we meet for a coffee on your way home? S xxx'. I text her back telling her what time my train was due to get in and we arranged a time. ************************* I wal...

Vacation Expectation

by IPleaseYouTease on Oct 6, 2020
Fetish

The wife's side of a conversation with her husband as she gets packed to go on a 10-day vacation with her lover and leave him behind. ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ "Okay Dearie. Up on the bed. It's almost time for me to leave. I have a plane to catch. Don't you worry. I know that once you're done binding your hands and fee...

Threesome Guide for Couples Pt. 07

by roomfor1more on Sep 19, 2017
How To

Chapter 7 – Moving from being social to threesome and beyond Introduction: To begin with, this is the last chapter and any future chapter will cover a topical issue, thought pieces, relating to a threesome. This chapter will cover transitioning to a threesome, having a threesome, and after the threesome. If we are to use the journey analogy for the last ti...

Three Days and Three Ways

by dirtymeanandhard on Sep 19, 2017
Erotic Couplings

I was visiting Eva and I was kind of bummed at first that her friend Jessica showed up as a surprise too. I'd been looking forward to three days of getting my cock sucked, spanking her, fucking her ass, and making her cream the panties I picked out for her. Instead, because I'm her dirty secret, Jessica didn't know I was there and drove in to spend time wit...

Caught By Our Babysitter

by kurgen on Apr 21, 2008
Exhibitionist & Voyeur

My wife, the kids, and I were to be away for the weekend. My wife arranged for the girl next door, who had babysat for us on occasion, to feed our dog. We were just at the train station when at the last minute my boss called with an emergency, canceling my trip. I sent wife and kids off on the train and headed home. Feeling a bit pissed off when I got home,...

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Cheerleader Chronicle Ch. 06

by tk5555 on Sep 19, 2017
Group Sex

A special thanks to my editor Cheer_Smartie526 for all the grammar corrections and excellent suggestions on improving the story. * Rick read the test message again. Ready to try a 3some? It was from Nancy. It seemed an odd text to receive from someone that was on a date. Rick slowly typed his response Yes His phone beeped when she responded. Call me n...