Tomboy Stories

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Yemeni Tomboy Chronicles

by Samuelx on Nov 26, 2017
Interracial Love

"Mature black Muslim booty, thy name is Naima," Omar Sultan thought to himself as he watched Naima Ali step out of the apartment building overlooking South Keys Plaza in Ottawa, Ontario. Tall and very voluptuous, with curves that her traditional Islamic clothing couldn't hide, Naima was a fine specimen of African Muslim womanhood. Omar wanted some of that so...

The Smash Mansion

by Onlysorta on Dec 20, 2020
Fan Fiction

The foyer of the Smash Mansion was rarely an empty place with all the contestants traveling between modes. Hardly a day went by where half the cast didn’t crash into each other. And it was surprisingly common to crash into a competitor who wasn’t wearing any clothes. But busy as it was, that only meant rumors between the residents spread quickly. If anyone s...

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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...

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...

Carmen the Tomboy Giantess!

by Cryptosporidium137 on Feb 13, 2020
Fetish

Carmen chugged from the can of Coke in her hand and let out a monstrous belch. “URRRRRrrRP!” She bellowed before tossing the empty can over her shoulder. Carmen Thompson was a total tomboy who was known to be quite the delinquent around her town of Bayweather. She had been to juvenile hall once before, and came back even worse behaved than she had previously...

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Naughty Tomboy Neighbor

by MrJack on Sep 12, 2017
First Time

Readers; I couldn't get the idea for this 'dirty-old-man' story out of my mind, so I went ahead and wrote it. I suppose this is a tale of forbidden seduction, but after writing it, I'm not sure of who seduced whom. Did the 'old man' seduce his 'innocent' neighbor or did the 'young woman' seduce him? If you have an answer, please let me know. Thank you. (Pa...

The Hardest Answer: Ex-Lover

by cawastedyouth on Sep 16, 2017
Non-Erotic

That Saturday morning around eleven in the morning, Julia parked the car in the large structure and climbed out eagerly looking forward to the events around the corner. Lauren got out of the car with apprehension. She looked around nervously the parking structure. There were all sorts of people getting out of their cars, some wearing costumes and chanting ex...

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...

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...

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...