Tomboy Stories

1,641 results
Orientation
Length
Source
Infinite Scroll

Somali Lesbian Diaries Ch. 01

by Samuelx on Sep 16, 2017
Romance

Try as I might, I can't help but being obsessed with lesbian sex, and for a Hijab-wearing, pious Somali Muslim sister like myself, that's quite a dilemma. My name is Amina Khalid and I live in the City of Ottawa, Ontario. Life as a Muslim woman in the Canadian Capital isn't easy, because of the expectations of my traditional Muslim family and the temptations...

The Tomboy And The Tranny Ch. 02

by Selbryth on Sep 12, 2017
Transsexuals & Crossdressers

(Continued from CH 1) Then I just knelt there, looking at her. So beautiful. So pale and perfect - such a narrow waist and curvy hips and - god, what a glorious ass! But then the hornies came up full again and I pulled back, grabbed her by the hips and rammed in. She grunted. Her knees spread out a little bit more and I rammed back and forth again. She gasp...

When a Woman Loves a Man

by Samuelx on Sep 12, 2017
Erotic Couplings

The morning comes. Paul Grimes wakes up and gets out of bed. He looks at his wife Sheila as she lies on their bed. Sheila is a tall, plump woman in her early forties. Her hair is light blond, her eyes a pale blue and her skin bronze. This Irish-Italian dame was a real beauty once. Lately, things hadn't been great between Sheila and Paul. For starters, they w...

The Pixie & The Lady in Leather

by MsDreams on Sep 17, 2017
BDSM

He met them at separate times in different places. One over a year before when he first negotiated to scene with her and she said no not yet perhaps another time, the other only a half a year ago when she was visiting from far away as part of a poly family exploring a new venue. In the year since he had met the first, he had grown a lot in his role as bottom...

Can I Borrow Your Wife?

by Sinburn on Jan 22, 2021
Cheating Spouses

Sean admired his wife Chloe as she slipped into her comfy pyjamas. He often wondered how he had ended up with such an attractive woman. He wasn’t bad looking in fact many would have called him handsome. At 27 he was tall and trim from regular running, with mousy brown hair and a bright friendly face that put people at ease. The reason he was so surprised tha...

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A Special Girl

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

Please allow me to introduce myself. My name is Steven Brun. I'm a young Black guy living in the city of Boston. I recently graduated from high school and started college. I go to Boston College. It's a school full of rich white kids but I'm liking it so far. The city is big, much bigger than the small town that I came from. I'm from Fitchburg, by the way. I...

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...

A Little Drama

by Hornsup on Sep 12, 2017
First Time

Standing in the wings of the high school theater, Jeff half-heartedly watched the play rehearsal. In his last semester of his senior year, he had taken drama as a blow-off class that happened to have a bunch of girls. The best part was that many of the girls in the play he had never had classes with before - a new field to play in! As always, several girls h...

The Orgy Room

by C Love on Sep 1, 2017
Group Sex

My senior year in college I was sleeping with Lana, who lived in a suite with three other girls. All of them were very sexually active, as a matter of fact, I had been with each of them at one point or another, so I guess I was the one who was very sexually active. The suite they lived in had two bedrooms connected by a bathroom, but they put all four beds i...

Geography

by velvetpie on Sep 16, 2017
Transsexuals & Crossdressers

I met Johanna on a blind date. That usually spells disaster and I was quite happy to find that I was wrong. But let me start from the beginning. My best friend, Julia, had a hot date with a Latina named Sorita and needed a second for a double date. "Her name is Johanna." Julia handed me a beer, sitting down on the couch next to me. "And I met her this morni...