Tomboy Anal Sexstory Stories

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Black College Men

by Samuelx on Sep 1, 2017
Group Sex

Nightfall. Time to head out in the city looking for adventure. This has been our tradition for as long as I can remember. My name is Kyle Jacobs and I am a rather adventurous young black man living in an undisclosed location in North America. I'm currently in college, studying criminal justice while playing football. These are my stories. I went to pick up m...

Sexstory

by JCSTREET on Sep 14, 2017
Erotic Couplings

I'm standing in the arrivals lobby of Dublin airport; waiting for a woman I haven't seen for 23 years. I have jelly legs and dizzy spells. I have flights of fancy and fugues. I don't know what I'm doing here. I don't know who called this meeting. I can't even remember what I'm doing in this country. I know she's coming. It would too late to walk away. I'm s...

Vegas: The Dirty Dozen Ch. 06

by Benny024 on Aug 31, 2017
Group Sex

I was standing in the in one of the small, dark theater rooms watching a movie. A white woman was sitting on a black man. He was pumping his large cock into her fat pussy while she sucked a large white cock. A third man had moved up behind the woman to put his cock into her dilated asshole, when I noticed a petite, young, white woman slowly enter the theater...

Porn Heavy: T's Pool Party

by Sean Renaud on Sep 13, 2017
Group Sex

Growing up as a tomboy had both advantages and disadvantages and from time to time it was really hard to tell which fell in to which category on a daily basis. At least that was how Tiana felt as she stepped out of her house and looked around at her friends of well over a decade. Starting with the disadvantages of being a tomboy was she didn't have any fema...

Lucky Alan Ch. 09

by TLMorgan on Sep 25, 2017
Anal

Alan had been lying in bed all Sunday afternoon trying to recuperate from the wild and raunchy fuck fest he had last night until the wee hours of the morning with the high school varsity cheerleading squad. By the end of the exclusive party, he had given his last load to the bustiest and most untouchable girl in school right in the face. Unfortunately, he wa...

The Sim - Custom Scenarios Pt. 04

by justsomeguy41 on Aug 7, 2018
Anal

Disclaimer: This story is, as always, set in a simulated virtual reality and heavily anal focused. This chapter is a friends with benefits scenario with a tomboy girl. If that's not your thing, you should probably skip this. This is all pure fantasy; don't expect realism or normal behavior. ~~~ "So Simone, I was thinking this time around you could put me...

Ploughing Kate's Backyard

by Surferdude_74 on Jun 12, 2019
Anal

Kate and I had met time and time again in various college courses or at the odd party. We had talked about insignificant issues and might have had a drink together. We have had pleasant conversations, but I cannot say that I found her stunningly attractive. She was a good drinking pal, a kind of tomboy with her really short, light blond hair and her slightly...

Carrie

by Dawns on Sep 16, 2017
Anal

Four years ago as a 14 year old the girl trapped inside my body was screaming to be released from her prison. I had showed up at school on the first day of my freshman year wearing a dress from my sister's closet. I've never worn boys clothing since. Carrie became my new persona replacing Todd. Psychologist Jen Robertson, herself a male to female transsexua...

The Hentai Simulation

by FootLicker8 on Apr 29, 2025

(Cover image by Kairunoburogu) This story is public and I would greatly appreciate if you considered writing your own branch for it to give some more options to the readers. Anything allowed by the Chyoa rules is allowed here as long as it fits the premise of course. Please read the writer guidelines to help you fit your branch with the overarching lore befo...

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Create a porn star story

by fethishboy on Jan 23, 2010
Fan Fiction

There are many porn stars in the world. They are women who bring pleasure to men and women by performing the arts of porn. But what about their stories? What do they do in their spare time. Well these are their adventures. You could tell stories of the like of Gianna Michaels, Jenna Jameson, Summer Cumming, and many others. But who does the story star. Other...

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