Caught Jacking Off Stories

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Jacking Off For Jennifer

by callmeishmael on Sep 12, 2017
Exhibitionist & Voyeur

Jennifer and I work for the same law firm, but in different cities. She works in the same group I do and is basically my counterpart. She already worked for the firm when I was hired and spent two weeks with me when I started, to help get me up to speed. She comes into town about once a month for face-to-face meetings with clients and we speak on the phone e...

Main Attraction

by Neecer on Sep 12, 2017
Exhibitionist & Voyeur

As always my stories are true with that said enjoy! My husband his name is Tony mine is Jill. We are a very open couple, we both are very sexual people. It all started off in bed one night we were having some very heavy fore play. We both were talking very nasty to one another. I looked at Tony and told him that I wanted to give head to a strange men some t...

Why I’ll Never Go Sharking Again Ch. 02

by tsfan84 on Sep 13, 2017
Transsexuals & Crossdressers

Earlier today, I was raped by a shemale. It was my first sexual experience with anyone not carrying two X chromosomes. It hurt like hell, at first and to be totally honest, I'm still sore. But it also felt really good after a while. The sensation of being.....what's the word I'm looking for here..."filled," while cumming is the best. Having your ass clench d...

The First Time is Always a Bitch Ch. 03

by peeder_exposed on Sep 1, 2017
Group Sex

The stopwatch clicked a second time. "Eight minutes thirty-seven seconds," Dave announced. "Not bad. Not bad at all. Okay, round two. We have the seven of spades. Seven of spades is Markie Mark. Way to go, buddy. Who's got the seven of hearts? All right, Ralphie, my main man, front and center." Two other men took our places on the couch and got down and dir...

Danielle's Discovery Ch. 01

by D_K_Moon on Sep 16, 2017
Toys & Masturbation

This is a complete work of fiction, any resemblance to anyone alive, or dead is purely coincidental. * My name is Danielle Millward, and this is my story. I was raised in a very conservative Christian family. Sex was never mentioned, other than it was the duty of a woman to save herself for her husband. Virtue was everything. I went to a Christian school f...

Wild Wet Weekend with Daddy Pt. 03: Saturday Pt. 01

by DirkDaggler on May 15, 2019
Fetish

This is a work of fiction. This story contains piss, anal, throat fucking, threesomes (MMF and FFM), and diapers (NO scat or mess!). Daddy and girl are pet names and all characters are over 18. As stated in the first installments, the main character Jacquline is 28 and her lover, Derek (daddy) is 35. This is part three in a series. Thanks for all of the pr...

High School Friend Has A Secret Ch. 02

by horneyguy99 on Sep 12, 2017
Transsexuals & Crossdressers

It had been a little over a month since my first transsexual encounter and it still felt like it was yesterday. My night with Michelle had been a night of many firsts for me but I regretted nothing about it, only that I had to hide it from my girlfriend. I wasn't the cheating type and it did bother me to a certain extent that I was keeping this from Brittany...

Have You Ever? Ch. 02

by StallionKinge on Sep 16, 2017
Group Sex

Samee and I had been at it for months, almost nonstop. We were living in the apartment above my studio. She would come from work and we'd screw each other's brains out before fixing supper, or I'd come home from a location assignment and we'd screw each other's brains...you get the picture. Ah, that wonderful, blissful, happy/crazy time when you're first f...

A Very Special Club

by LorenzoAbajos on Aug 31, 2017
Group Sex

We met at a different house every time the club met. We might meet only once a month with all the members, but some members would meet in smaller groups more often if they cared too. We were young and old, male and female, beautiful and average, gay and straight, and we all loved masturbating. It had all began slowly, of course. I was the instigator. I love...

A More-Men Wife Ch. 01 Pt. 02

by PolySwingerWife on Dec 14, 2020
Interracial Love

I met my husband on a Monday night. He proposed to me on Tuesday night, and by Friday afternoon we were married. Early that Friday evening, I lost my virginity to another man while my husband watched. And now me and my husband, Ray, were looking for an apartment. As we looked through the paper, I mentioned to Ray that Carl, the man I lost my virginity to, sh...