Tomboy Working Nude Sex Stories Stories

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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...

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...

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...

La Playa: Polynesia Ch. 01

by Fog43 on Sep 14, 2017
Group Sex

The following is the first story in a trilogy sequel to my La Playa series. It is set in the year following the opening of the original resort, and now a team is working in French Polynesia to develop a second property. If you are interested in character development you may want to go back and read the original stories, but I hope you will also find that the...

Nude Day Texas Hold 'Em

by alexxxis on Sep 12, 2017
Group Sex

I've always been a bit of a tomboy. Who am I kidding? I am a down-and-dirty, in-your-face tomboy trapped in a little girl's body. Now before you guys get all pervy on me, when I say 'little girl' I mean my body has the physical attributes of a 13 year old girl but I'm actually 21 years old (nearly 22-please send birthday greetings and cash if you have extra)...

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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The Wicked Witch Pt. 01

by Dimaued on Apr 15, 2020
Romance

Jamie sat in his plane seat annoyed, annoyed that the stewardess mistook him for a girl, annoyed that the baby behind him had been crying for hours and annoyed that he only had a single earplug rendering it useless. He was always teased for his looks, but he just grew accustomed to the teasing. As a matter of fact he was glad of his appearance it was because...

Lust for the Golden Witch, or the Death of Mystery Person X

by MidbossMan on Feb 16, 2020
Fan Fiction

Introduction to the Rokkenjima Incident and H.I. Player: October 5, 1986. A raging storm swept over the tiny island of Rokkenjima. Upon this island lay the western-style manor of Ushiromiya Kinzo, the head of the wealthy Ushiromiya family. A day earlier, the children of the Ushiromiya family arrived to take part in a yearly family conference, bringing with t...

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Eris's Awakening

by clementchong on Apr 22, 2025

Eris awakens to a gentle beam of sunlight peeking through her curtains and falling onto her face. She scrunches her eyes in discomfort before sitting up, her bedsheets sliding off her body and revealing her nude form. Her eyes still half-closed from sleepiness, she shuffles over to the full-length mirror in her room, ready to get dressed for the day when she...

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