Gay Crossdressing Bondage Stories

609 results
Orientation
Length
Source
Infinite Scroll

When There Is Nothing Left Ch. 01

by FangsAnarchy on Apr 3, 2019
Gay Male

~~~~~~~~~~~~~~~~~~~~ Edited by: Tangent Joker ~~~~~~~~~~~~~~~~~~~~ "Will it hurt?" Antonio tilted his head to look up into Parker's brown eyes. His lover was sporting a good amount of dark blonde scruff on his otherwise boyish face. It wasn't in honor of this month being November but rather because they couldn't afford razors and shaving cream. It was...

Once Is Not Enough

by KeithD on Aug 13, 2019
Gay Male

I knew who he was as soon as he sat at the bar and smiled expectantly at me. It was obvious that he was picking me out to serve him. There weren't that many successful and recognizable Japanese actors in Hollywood. Mike Mori was one of the stars of the long-running series, Hollywood Vice, the series having run long enough to put him into his early forties. S...

The New Slave Ch. 01

by martin_x59 on Sep 14, 2017
Gay Male

Editor's Note; story contains nonconconsentual situations. I would like to start by saying I am new to writing so I hope you don't judge me too hard on my literary naivety. Nor am I experienced in Bondage or Master Slave relationships. This story is pure fantasy from my part and is about what I find erotic and stimulating. Please bear this in mind when read...

My First Threesome Ch. 01

by Cyanlot on Sep 25, 2017
Gay Male

[This is in the category of "Gay Male" out or deference to those fragile souls on Literotica who are threatened by any tales that involve man-on-man sex and, to avoid challenging their fragile masculinity, want those stories in the "Gay Male" category. Those looking for true gay male sex stories may be disappointed. In fact, this is a love story between a ma...

On the Rebound

by corruptiveInfluences on Sep 14, 2017
Gay Male

I've tried writing several different stories, but have never posted anything before this. So hopefully this is something at least somebody out there enjoys reading as much as I did dreaming up. The usual warnings apply: if you're under 18, or these types of stories are illegal for you to read in your area, then go somewhere else. Otherwise, enjoy. ***** Th...

Made Over

by gbr2004 on Sep 14, 2017
Gay Male

This story involves forced man to man action and gets into humiliation, bondage and discipline. Do not read if this doesn't match your interests. * My name is Steve and just turned 18. I was finally going to have some adventure in my life. This is my first time away from home, a small town in Kansas. I had been accepted at USC in journalism school. I was s...

Taking the Plunge

by jack_straw on Aug 29, 2017
Gay Male

Remember when you were 10 or 11, and your buddies double-dog dared you to jump off the high diving board at the local swimming pool? Well, something like that happened to me recently, and it was the most incredible erotic experience of my life. I still can't believe I did it, but I guess if you climb up on the board often enough, eventually you'll throw ca...

The Brownstone: Scott Ch. 03

by jayjayk on Sep 14, 2017
Gay Male

(Authors Note: This is the 11th installment in the Brownstone series. In reading order they are: Michael Ch01,02 Charles Ch01,02,03 Michael Ch03,04,05. Scott Ch01,02 Please bear with this chapter, it's not the strongest, but it's necessary to build the storyline for the chapters to follow.) **************** Michael had tried calling Scott to let him know...

Troy Tamed Ch. 04: Ready, Willing

by sr71plt on Aug 18, 2017
Gay Male

My feeling of gathering isolation wasn't helped as we neared the coastline of the small Cape Verde island of Brava that Klaus Gehler said he owned a big slice of and I saw Gehler's red-tile-roofed native stone villa hovering over the top of a cliff. There seemed to be only a narrow pathway through lush semitropical foliage rising and cutting back here and th...

Heaven On Earth Ch. 07

by byIL85 on Aug 17, 2017
Gay Male

Chapter 7: Out of a Storybook An astonished cry that was meant to be "Jane!" escaped my lips, but it was muffled by the tape over my mouth. She walked over to the bed where I could see her in a better light. I was still dizzy from being knocked out, but a closer look told me the truth. This was not Jane. Sure, it was the same long, flowing hair, the same wa...