Erotic Stories Tomboy Stories

164,937 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

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...

My Life

by JamieeR on Sep 14, 2017
Novels and Novellas

It's raining again... or maybe it's better to say it's still raining. But at least the bed is warm and comfy, and looking at my watch, I still have an hour before I have to get up and get to class. My name is Jillian Aimee Boyack but everyone calls me Jamiee. I'm was cursed to be short and skinny at five-feet one-inch tall and weighing in at ninety-five poun...

Keeping Tabs Ch. 0

by sphynxaif on Sep 17, 2017
Non-Erotic

Note: this is a Preface to my upcoming erotic series titled: Keeping Tabs. This Chapter is more for those who like to really get into their stories. Thus, this is Ch. 0 and not 1. Feedback is always appreciated! ~~~~~~~~~~~~~~~~~~~~~~~~ Chapter 0. –Preface As a kid, I always hung out with four other kids from my neighborhood. We would do absolutely every...

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...

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...

The Fall of Lana Craft

by HotRumours on Sep 14, 2017
Novels and Novellas

(Every character in this story is at least 18 years old. The story may contain exaggerated actions, plots or physical features. The main plot consists in a degrading and abusing a female main character, which will only be viewed by an outside perspective and may be quite passive or submissive. The story will not feature any urination, feces, blood nor typica...

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...

Open in Reader

A Bisexual Jock And His Tomboy

by Samuelx on Sep 17, 2017
Non-Erotic

I think that love and friendship really shouldn't mix. Seriously. It doesn't matter if you're a man or woman, black or white, straight or gay. If you are friends with someone and madly in love with them at the same time, you're going to end up doing or saying something really dumb. You might succumb to the urge to tell this special man or woman how you feel...

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... -------------...