Tomboy Stories

1,641 results
Orientation
Length
Source
Infinite Scroll

Fun and Games in the Bathroom with Mike

by Kim666 on Dec 10, 2018
Fetish

My name is Kim. I am 53 years old, recently divorced and living in London with my wonderful daughter. I am writing about my sexual adventures, growing up in the 1980s as a way of making sense of my past and celebrating a glorious time when I was young and carefree. Between 1987 and 1989, I had some of the most gloriously uninhibited sex of my life. After tha...

Conlan & the Tomboy

by S.W.A.T.-Samurai on Sep 13, 2017
NonHuman

-*-*-*-*-*-*-*-*- Liz the Tomboy -*-*-*-*-*-*-*-*- Liz ran through the alley with all her might. Just barely dodging garbage cans and dumpsters has she ran like a bat-out-of-hell. Still not believing what just had happened before her eyes. She had been out on the town with her new friend she had made at the bar she worked at. Unfortunately for her the b...

Body Parts Ch. 02

by he_loves_her on Sep 16, 2017
Romance

This may not be the usual story of a man's love of a woman's legs, but who says I embody the usual. The woman who is my mate has the most amazing body I have ever known and in talking about her, one part at a time, I may take some license when discussing her. Her legs are like chameleons. No they don't change color to match her surroundings but they do cha...

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...

Possession Process

by Fayd1 on May 27, 2020
Fetish

Intro + Characters John - 18, an average high school boy, who you play as, Does not stand out particularly, It is September, John just got home from a day at school, he plops himself on the couch, feeling exhausted, his sister Becca walking down from her room wearing her pajamas "Go shower John, you smell like shit" she says with some obvious disgu...

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Turkish Delight In Texas

by Samuelx on Sep 16, 2017
Interracial Love

Low tolerance for bullshit, that's something I most definitely feel every day of the week. There's an epidemic of stupidity out here in the Southwestern United States, and I wonder how long it's going to be before I lose it and smack a damn fool. I'm already in anger management over kicking some bitch's ass at Wal-Mart last month, so I don't need any more tr...

Sally and the Sailor

by RetroFan on Oct 21, 2019
First Time

INTRODUCTION & DISCLAIMER - Petite and pretty blonde Sally works in a factory and has always been a tomboy to the despair of her strict and more traditional mother, who wants her daughter to act more feminine. Stuck at home and recovering from a bout of measles, 18-year-old Sally sees the neighbors' handsome son Eddie, now attired in the uniform of the US Na...

Bisexual Butch Women of Quebec

by Samuelx on Sep 16, 2017
Interracial Love

"Merci beaucoup, thank you so much for this gift," Miranda "M.T." Tupinier said, smiling, as her boyfriend Benjamin "Benny" Guerrier solemnly handed her a pack of brightly colored men's boxer shorts. She wasn't expecting that, especially from him. The two of them were chilling inside Benny's apartment in Montreal-Nord, and he'd gone out to grab a cheese pizz...

Somali Muslim Swingers

by Samuelx on Oct 24, 2018
Transgender & Crossdressers

"That was definitely a fun night," Hodan Yasser-Ali said to her husband Bilal Ali as they lay in bed together, basking in the warm afterglow of a good fuck. Earlier, they had a third party in their bedroom, and said third party definitely left a mark on them, in more ways than one. It was the couple's very first threesome, prompted by certain sexual revelati...

Got Milk? - Delilah & Mac Ch. 01

by Little_Mac on Dec 11, 2017
Fetish

It was the last day of school before the weekend break. Even though it was Spring, it sure felt like Summer had crept in early, with today sporting a sweltering 97-degree sunny day. Students heading to school were lucky enough not to have to experience the journey of walking through the sun. One student was not so lucky, however. 18-year-old Mackenzie (affe...