Gay Role Reversal Stories

2,054 results
Orientation
Length
Source
Infinite Scroll

Liaisons Ch. 01: The Baron's Plans

by sr71plt on Aug 18, 2017
Gay Male

[This completed series will run in five chapters and will complete posting at Literotica by the end of the third week.] ***** January, 1924, the Baron's Austrian Mountain Chalet The snow had started to fall fast and furiously when Lady Elizabeth and her son, Paul Winslow, descended from the first-class compartment. Their journey on the rail trunk line fro...

The Cocky Young Associate Ch. 02

by boyganymede on Aug 18, 2017
Gay Male

For about a week, Matt and I pretended that nothing had happened, until our mutual desire overcame our inhibitions. Matt and I got together for weekends and sometimes weekday evenings, at either his apartment in Logan Circle or my house in Fairfax. On other weekdays, since we both tended to work later than most other people in the firm, he called me to his o...

Out of Uniform Ch. 05

by gustavca on Sep 14, 2017
Gay Male

I gained the bridge, checked in with the duty officer and was leaving when an acrid smell permeated the bridge followed but a loud grinding noise. Apparently the jerry-rig had not lasted a full day. I spun on my heel and made my way quickly to Engineering. Along the way I was asked numerous times what had happened. "You'll know when I know," was my curt res...

Back Stage

by RedTrickster on Aug 18, 2017
Gay Male

Jared sat in a corner of the greenroom off by himself going over the script once more. It helped him to get into character and smooth over any rough spots. He picked absently at the blue silk shirt that was part of his costume and turned the page. He was reading a part that had been giving him trouble recently and the director was getting tired of pointing i...

Logic One Oh Ouch

by sr71plt on Aug 18, 2017
Gay Male

It was the first month of my graduate school, and it was my turn for the "introductory" evening with my Logic professor, Paul Hollings. When I'd asked someone who'd taken his class the previous year what the proper attire for such an event was, he had just given me a lopsided grin and said, "For a handsome guy like you? I'd suggest very bulky clothes." He h...

Halloween Kink

by toddstop on Aug 18, 2017
Gay Male

"Hurry up, babe, we have to get going," Jared called through the door. I had to grit my teeth and tear my eyes away from the mirror to answer with, "Just a minute." The matching costumes had seemed like such a good idea when I came up with the concept. Now, staring at my reflection, I wasn't so sure. Too late now, I told myself. It was our first Halloween p...

The Bitch Top

by TuxedoPirate on Sep 21, 2020
Gay Male

He was tall and handsome and toned. He was like Adonis. Even his cock was the epitome of manliness. It was ten inches long and as thick as my wrist. When it was hard, it was like sculpted marble. I was going to enjoy tonight. I was laying on my blue satin bedsheets, arms behind my head and legs spread out. My cock was hard and was straining against my boxer...

The Vacation House Ch. 20

by 1Puck1 on Sep 14, 2017
Gay Male

"Rob, psst., Robbie are you awake?" I'm groggy, disoriented, in a state of twilight sleep. Not sure if I am awake or asleep, dreaming I had heard my name. Lays silent, I try to focus on any sounds that might have been similar to what I might or might not have heard. "psst, Robbie, you awake?" There's no doubt about it, I'm hearing my name, a low whisper,...

Nicole Comes Out

by BlueEyedNick on Aug 18, 2017
Gay Male

In the early days of chatting online, so many years ago now, I used to chat a lot in various kinds of sexually themed chatrooms. More often than not I chatted under a female screenname. I've always had a very strong feminine side and I was good enough to get away with it. Under the various female names I used I chatted with men and women alike. Usually it wa...

First Experience With A Man Ch. 2

by girlboybootsie on Aug 18, 2017
Gay Male

Leading me into his bedroom, I find the sexy pink corset, panties and stockings that he bought the other day at Frederick's all laid out, on his bed. There is also a pair of silicone "boobs." "I didn't even have time to give it to Jessica, so you can have it. I'll leave you alone while you change. You will need to slip the boobs into the cups of the corset....