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 Tomboy Breeder

by Sixes on Apr 22, 2025

You wake up in a dark void. You don't remember much. You know that you had gone to sleep after having an aggravating meeting with your superiors. Briefly, you wonder if you had died or not. But a voice from behind cut off that train of thought exceptionally quickly. "No, you're not dead. You're still alive. I just dragged you here to have a quick talk.&...

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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...

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...

A Humiliated Tomboy

by humiliationstation on Feb 19, 2020
Exhibitionist & Voyeur

Alex sat on her bed, playing video games. She was a cute high school senior in a baggy hoodie and basketball shorts, her orange hair cropped at her shoulders. She was sucking at her braces in concentration when she was interrupted by a knock on her bedroom door.What's next? Claire, her bully Her best friends Nate and...

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The Bet

by Adventive on Apr 29, 2025

Chris wasn't always The Stranger. He used to be decent, kind even. He once worked at a bakery and had a smile that could warm a winter day. Then on one ordinary Tuesday, he stumbled upon a lamp that held a mischievous genie. The genie told him that he will only get one wish. Blinded by the promise of power, Chris wished for infinite wishes. The genie, with a...

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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...

Inferiority Complex

by 18bmay0 on Apr 22, 2025

Sex. It's an insatiable urge that everyone has. Even me, with my below average penis, crave sex. Unfortunately, due to that little setback of having an inferior cock, I lack any sexual experience with a girl. My dick is just too small, and I could never satisfy a woman. Still, I lust and pine after my crush like any other love struck fool. As an 18-year-old...

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