Gay Roommate Stories

34,652 results
Orientation
Length
Source
Infinite Scroll

Kisses for Michelle

by Couture on Sep 15, 2017
BDSM

"Oh Michelle, you should have seen him squirm," Leslie snickered. "I had him in the palm of my hand....literally." That's Leslie for you. Blonde hair cut at shoulder length. Big blue eyes. Beautiful. And an impossible tease. Back in her dorm room from her date, animatedly telling her best friend since middle-school and current college dorm-mate about her la...

Roommates Ch. 01

by HerLittlePiggy on Sep 14, 2017
Exhibitionist & Voyeur

Ch 1 Planting the Seed I lay on my bed silently feigning sleep and watched my roommate, Henry, walk naked from the bathroom. His long flaccid cock swung heavily from side to side as he walked like the trunk of a small elephant. He was always walking around the room naked it unnerved me at first but I had gotten used to it and I didn't pay it much attention...

Pretending to Be Gay to Trick Girls

by jimbo32 on Sep 13, 2017
Erotic Couplings

My name is Paul and I know that it is hard to believe but I came up with a great way to get women to fuck me. I trick them! I first had the idea when I was in high school and some of the hot girls from my school were talking about how they were looking for other girls to be roommates for college because they would never trust a guy and their parents wouldn'...

A Transvestite Love

by Martins on Sep 16, 2017
Transsexuals & Crossdressers

"Are you sure you want to go inside?" Heather asked. "Of course. I mean, we've come so far, haven't we?" I said. "But you know what I am." Her eyes seemed sad – her tone emotionless. Just moments earlier we were having dinner and those eyes were bright and the conversation cheerful. It was like we were in another world, but now reality was sinking in. "Lo...

Pledge Duties

by Ruggerdog on Sep 15, 2017
Group Sex

My first time as the "guest star" in a threesome was in college. There was a girl named Tara who I had met and flirted with for weeks – she was always hanging around the frat house where I was a pledge, and I wasn't sure if she had a boyfriend in the frat, or was looking for one. She was really cute, had a wicked smile, a gleam in her eye, and a fat, round a...

Filled with Joy

by BuckyDuckman on Sep 13, 2017
Fetish

Welcome to my Nude Day 2015 entry. It's a long one, so grab a beverage and maybe a sandwich before diving into it. This story includes graphic depictions of man-on-man sex as the hero wrestles with being a straight guy who enjoys sucking off other guys. There's lots of cumplay, a bit of humiliation, pegging by his girlfriend, and a very big piece of CFNM. If...

Cross-Dressing, Gay & Lesbian Sex 01

by SusanJillParker on Sep 13, 2017
Transsexuals & Crossdressers

There are no underage characters in this story. All characters are over the age of 18-years-old. Cross-Dressing, Gay & Lesbian Sex 1 Sometimes wishing he was born a woman, Daniel struggled with his need to cross dress. With his hands resting on her dressing table and his body leaning in for a closer and more critical look at himself in his wife's lighted,...

Panty Posers

by EROTICbearscribe on Jun 1, 2020
Transgender & Crossdressers

PRIVATE PANTY SESSIONS Ch. 01 "Wait! What? Say that again." Doug, my roommate of two years, closed his eyes and took a deep breath. Tension hung heavy in the air. I allowed him to take all the time he needed to explain even though my mind was racing the way it does when your entire world has been turned upside down. I could see he was struggling. It look...

iPad Roommate

by Oddballs on Dec 31, 2020
Science Fiction

“Pffff, another sweater.” Aaron says as he holds up the red, green, and white Christmas garment is aunt sent him. “At least this one as an actual cool design on it.” Ian says as he smiles at his roommate. In a small house in a secluded neighborhood covered in snow, two men in their mid-20’s enjoy a simple holiday together. With the pandemic still at large, b...

Open in Reader

Almost Pt. 01

by danoctober on Sep 18, 2017
Romance

There are times I wish I were a child again. That place where blind innocence and unconditional trust of family and friends was the norm. No troubling thoughts or confusion of the mind. A beautiful state of ignorant bliss. But with that great desire to be a grown up and do all the things adults do, we run in haste to discard our childhood tranquility. And wi...