Tomboy Fucking Stories Stories

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My Slut Wife Georgie

by GeorgieTom on Dec 3, 2018
Loving Wives

I went to school with Georgie and she was always a bit of a tomboy, an attractive tomboy with blond hair, and a very sexy figure, shown off by tight jeans and tight t-shirt topped off with a leather biker jacket. She was always a very confident young girl and seemed to be a bit of a leader of a gang, a rebel and always broke the rules, smoking at school, pla...

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...

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...

From Tomboy To Boy

by PredatorSmile on Sep 16, 2017
Transsexuals & Crossdressers

Mike Flannigan is a wealthy man who, at the age of forty, could certainly afford to retire from his law firm with a lot of money to spend. He had always been the most driven person in his family. He was born in 1951 in Dallas and lived there for most of his life. His parents were a working-class couple, a policeman and a teacher. Mike Flannigan went to colle...

George Becomes Georgina

by WarriorPrincessUK on Aug 18, 2017
First Time

This is a true story (I have changed the names for obvious reasons) about how, with the help of Literotica, I finally became a woman. My boyfriend challenged me to write this account and submit it to Literotica and anyone who knows me, knows that I nearly always accept a challenge. I am very grateful to michchick98 who kindly took time out of her busy life t...

Anatomy and Fine Dining

by LitEroCat on Sep 13, 2017
Exhibitionist & Voyeur

While sitting at the upscale bar in a fine restaurant, I wondered how big a mistake this was. What's the worst that can happen - an early night and web surfing back home? A beautiful black woman came in and looked around. I forgot to ask about race. I tried to catch her eye and flaunted my emerald green "It's ME" scarf. She looked past me and I looked t...

Bar Girl Ch. 05

by XerXesXu on Sep 19, 2017
Novels and Novellas

Chapter 5. "Belle." Belle. Girlie goes "satisfaction guaranteed" with Belle. Hardcore tomboy sex. Jailbait victim, Paolo. The afternoon proved so oppressive that, at dusk, the girls left for the air-conditioned refuge of Talent Spot. With umbrellas to keep off the worst of the rain, and dressed in shorts and flip flops, they splashed in puddles and stepped...

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...

Girls Playing Sports Naked

by NewWriter14752 on Apr 29, 2025

If you want to succeed, you need to sacrifice something. And in case of those girls, it's their dignity and modesty. Whether it's an eccentric coach or a historical tradition, those girls will end up naked in various situation. And you can decide how strong willed are they going to be. Do you want to see a strong girl, walking up to a mixed shower and slappi...

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Christy

by JH-1 on Sep 17, 2017
First Time

This story is strictly fiction, and is in no way based on any characters or names used. All rights are reserved. Please vote. * We were watching TV, when some commercial came on, I really didn't want to watch. I glanced at my lovely wife Christy. She had lost interest, and had snuggled up to me, and gone to sleep. My mind began to wander... -------------...