Gay Roommate Stories

34,652 results
Orientation
Length
Source
Infinite Scroll

My First... Turned Me Fabulous!

by BerkeleyJanine on Sep 16, 2017
First Time

I'm lying in the bed of a man who picked me up outside a gay bar a few hours ago, listening to the sounds of his gentle, contented sleep. Contented from my having given him delicious head, contented from having fucked me with my stockinged legs wrapped around his shoulders. I'm lying here, looking at the trail of clothing that marks our evening: my strap-y h...

Saving Savannah

by MTL17 on Sep 19, 2017
Celebrities & Fan Fiction

Author's note: This is a story based on Hellcats. Both the actresses and characters are over 18. * "Get that girl a hurricane and keep them coming." Marti Perkins grumbled as she heard Lewis's voice in her head yet again. Why couldn't he just have said 'get that girl a hurricane' or just 'get that girl a beer'. That would have loosened the brunette up....

Ostracism Pt. 05

by ReedRichards on Dec 3, 2017
Romance

Author's note: This story contains some anti-gay slurs. This is not meant to insult anyone, but they are necessary for the telling of this tale. I hope that the reader can see past any offense he might take, and understand why they are integral to the story. ****** Reality was in the slowly lightening room, as another school day was starting. It had been h...

2 Broke Girls In Love Ch. 02

by MTL17 on Sep 18, 2017
Celebrities & Fan Fiction

The first thing Max Black was aware of when she slowly returned to consciousness was a weight on top of her, which made her instinctively groan in frustration. She had lost count of the number of times she had woken up with some guy nuzzling her tits, and as she wasn't in a relationship right now and last night was a blur it was a safe bet she had made anoth...

Crossdressing Dad Takes on San Fran

by vikkihawe000 on Dec 24, 2019
Transgender & Crossdressers

*A bit different than my other stories, but shares some similarities. Let me know what you think. xx Vi ***** Kelly sat in a parked car in the San Fransisco Airport parking lot waiting for her father, Rod, to emerge from the terminal. Kelly loved her father and was glad he was visiting all the way from England, but she was not looking forward to him spendi...

Ultimate Toilet Slave

by HungryGuy on Sep 13, 2017
BDSM

(fictional story, WM/wf, AF/wm, AM/wm-nc, AF/AF/AM) Foreword: This story is a sequel to OH SHIT. OH SHIT is a sequel to TOILET SLAVE 2. TOILET SLAVE 2 is a sequel to TOILET SLAVE. This story is also a sequel to OH POO-POO, even though OH POO-POO is not a sequel to any other story. ### It was only last year that Steve had been a toilet slave in the ladies...

Ashley's Transformation

by heftylefty55 on Feb 6, 2018
Interracial Love

My name's Justin. I'm a 28 year-old banker and a high school baseball coach. I was raised by two amazing cooks and ever since I was a high schooler I've had a love affair with beer. As a result, I'm not exactly what you would imagine as the stereotypical athlete. But my upper-80s fastball and filthy changeup, coupled with the fact that I'm a lefty landed me...

Saturday Night Fever - The Sequel

by watchdwag on Sep 19, 2017
Group Sex

As the weekend approached, I became more and more anxious about what I had agreed to do. My name is Chris and last fall I was seduced by a hot blonde in her early thirties named Terry, who took me back to her apartment where her boyfriend Jim and another man introduced me to gay sex. While I did have sex with Terry as well, she encouraged me to give her boyf...

Pre-Op Roommate

by Dracthyus on Sep 11, 2017
Transsexuals & Crossdressers

I was a few months away from graduating college with my Theater Arts degree when Mark, my roommate, told me he was going in for the sex change operation. We popped a couple of beers and talked about this thing… he wasn’t sure whether he liked guys or not, he’d never done anything with them. But he liked dressing up like a woman, like acting like one, and fe...

Jack-Off Jim's Schoolmate

by Hornyman69WithU on Aug 19, 2017
Exhibitionist & Voyeur

Never were there two more incompatible people than my college freshman roommate and me. Surprising, given the college required everyone planning to stay in the dorms to complete a lengthy questionnaire so they could match you with someone who had common interests. Having selected your roommate, they sent you his profile in late summer. I was certainly exci...