Boy Wearing Girl Swimsuit Sex Story Stories

330,684 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Mark is in Trouble

by metacarpal on Sep 1, 2017
Group Sex

A decision had been made. Karen trembled with excitement. She was about to take the plunge. But she felt confident, encouraged by her husband that she had nothing to fear. Her husband Ben was such a sweet man and such a powerful lover. He had assured his wife that no young man in his early twenties would turn down such an offer, especially from such a sexy o...

Breath Holding Course

by Naxos on Sep 12, 2017
Erotic Couplings

"How would you like to increase your breath holding times from a measly 1 minute to 5 minutes or more! With the Julie Wilson Breath Holding Course you will join a growing group of men and women that enjoy freedom from one of the more basic human weaknesses; The need to breathe continually." A young man clad in a bright red and white Speedo swimsuit swam le...

Diaries of a Sexshifter Pt. 01

by MatthewVett on Sep 11, 2017
Sci-Fi & Fantasy

Entry 1 My name is Alexis. I'm a 19 year old girl. My name is Alexander. I'm a 19 year old boy. I should explain. I, that is Alexis-I, and Alexander, well, we share a body. We think of ourselves as brother and sister, but it's definitely more complicated than that. It may sound like something out of an anime or a science-fiction film, but when I sneeze, I...

Yvonne with Sue's Tropical Adventure

by yvonne2011 on Sep 19, 2017
Exhibitionist & Voyeur

Hoping to get more feedback!! Hi folks. Sue here with Yvonne writing. We've already explained how we have to keep our nude adventures somewhat private because of our business ties. Well, this story takes place thousands of miles away from home. That made it possible to get naked in more places and in some places where naked ladies don't usually show up and...

Sunken Ship Sex

by Naxos on Sep 13, 2017
Fetish

"How would you like to increase your breath holding times from a measly 1 minute to 5 minutes or more? With the Julie Wilson Breath Holding Course you will join a growing group of men and women that enjoy freedom from one of the more basic human Achilles' heel; the need to breathe frequently." The announcer was a deep voiced personality who was easily recogn...

Bosom Buddies Ch. 02

by bosombuddies on Sep 25, 2017
First Time

(Author's note: Everyone in this story is at least 18 years old) (Another shout-out to ErikaKane for her help editing the story to make it more reader-friendly, thanks!) * Turned out my last thought had proven correct: Stephanie kept our little dalliance a secret from everyone, even her BFF, Elizabeth. Was it shame? Or was she just concerned about upsetti...

Seducing an Older Woman

by mdiver on Sep 12, 2017
Erotic Couplings

I have a great job as a programmer for a large local company that allows me to work from home nearly all the time. That freedom has afforded me the opportunity to make my home a very comfortable work place. I have a nice den that I use when the weather isn't the best but the place I enjoy the most is my backyard complete with pool and deck. I created a small...

Suzy's Control

by kong0645 on Sep 15, 2017
Exhibitionist & Voyeur

Suzy's control: So, after reading these stories for years I decided to share some things that I've experienced myself. This is a story that happened when I was in a May-December romance in my mid-twenties. It all started when I was twenty-five. Her name was Suzy and she was in her early fifties but was stunning and very much looked more like a woman in he...

Our Mistress' High School Ch. 02

by Philnominal on Sep 13, 2017
BDSM

All the characters featured in this story are a minimum of 18 years old. * It had been a momentous few weeks for the 18 year old Colin Goss. Hopefully you will recollect the difficulties young Colin had faced for most of his adolescence. A generally low achiever who had seemed doomed to be one of life's misfits or never weres, he had long searched for but...

ENM Intertwined - Rorke Pt. 04

by SpecialtyM3 on Sep 23, 2019
Exhibitionist & Voyeur

While my friends went off to retrieve their swimsuits, I swaggered all over the beach flirting and chatting with every hot girl I could find. Maybe having a beach full of admirers would finally make Sage jealous. My confidence was back in spades. Most of these girls were friends from work, some of them were friends they brought along, others were just common...