Gay Crossdressing Bondage Stories

609 results
Orientation
Length
Source
Infinite Scroll

X Rated Robotic AI Ultimate Lover

by Alluring_Crimson_Shifter on Aug 18, 2017
Gay Male

*** "--------------------------" Chapter One: Home Alone with a Statute "--------------------------" Janie was home alone. Her husband was off on another lengthy business trip and she was so horny that at times she could not think straight. She stayed in bed and started rubbing her breasts. It felt so good that it was almost like being with her man on a...

How I Found a Keyholder

by 1077ad on Aug 18, 2017
Gay Male

Author's note: This story was written while I was self-locked in chastity, and the locations are loosely inspired by real locations that I have been to with friends. This is otherwise a work of fiction which involves accounts of some things I haven't done (yet!) so hopefully it mostly rings true. Your comments and constructive criticism are more than welcome...

Fire & Ice

by TuckerMcCallahan on Sep 1, 2017
Gay Male

Author's Notes: This is a copyrighted work of fiction written by Tucker McCallahan. All rights reserved by Tucker McCallahan. If you are reading this story anywhere but at Literotica or the author's personal blog then it has been posted without permission. Please report plagiarism to: tuckermccallahan-at-gmail-dot-com. My toes were completely frozen; I...

First Bi-Guy Experience Ch. 03

by Resparvae on Jul 15, 2020
Gay Male

If you think you might enjoy this real life effort from me could I suggest that you read my first two real life submissions? In my first Literotica effort I wrote about an affair with an older woman, Muriel. From day one I have had a thing for older women, my first being when I was 17 with a firecracker hot 46 year old neighbor that I had known since I was e...

Kindness of Strangers Ch. 03

by bjmichaels on Sep 14, 2017
Gay Male

By the time I reached the outskirts of Houston, the adrenaline-rush I was feeling was counter-balanced by the rush-hour traffic I was stuck in. Stop-and-go traffic---I wanted to scream! And then the rain started... OH MY GOD---WHAT IS THIS---A MONSOON?? The rain was so heavy, it was difficult seeing the brake lights of the car ahead of me. My nerves were f...

A Stallion Affair Ch. 01

by AmethystMare on Nov 27, 2017
Gay Male

This is a short work of erotic fiction containing furry, or anthropomorphic, characters, which are animals that either demonstrate human intelligence or walk on two legs, for the purposes of these tales. It is a thriving and growing fandom in which creators are prevalent in art and writing especially. ***** Stallions after Hours Jason yawned and stretched...

Satisfaction Ashram

by sr71plt on Aug 30, 2017
Gay Male

As I stood outside the entrance to the old British colonial-style Windsor Hotel in Nuwara Eliya, Sri Lanka, in the shadow of Mount Pidurutagala, waiting for someone to take me up to the ashram, I couldn't believe how far—and how far back in time—I had moved from Teddy's cabin in the Catskills. From the moment Teddy's business partner, Mort Whitley, had drive...

The Jackal House

by castlequill on Aug 30, 2017
Gay Male

When I was 18 years old, I was kidnapped. Except, it wasn't your typical kidnapping. There was no ransom call, no revenge plot, nothing. Nothing except a couple of seriously fucked up, twisted minds of some seriously fucked up, twisted psychopaths. It was the summer after I graduated high school. My best friend Lacy and I embarked on a 2 month backpacking...

Sequences Ch. 03

by luvkitten on Sep 14, 2017
Gay Male

"Still hurt, Sequence?" Tulip asked as she helped him wash the next morning. "My arms are ok. My side still hurts a bit. A little tear. I'll be ok." Sequence replied quietly. "You nervous?" Daffodil said. "Can't walk in those shoes. I'll fall, he'll be angry." "Small, high steps." "High?" "Yeah, lift your knees high but keep the steps small." "Ok, I c...

Patience in Cape Verde

by sr71plt on Aug 18, 2017
Gay Male

Stefan almost had me that warm afternoon in the summer pavilion of the Eisler country house in the Vienna Woods. We had played two sets of tennis, stripped down to our shorts in the unusual August heat on the mountainside above Vienna, and I knew by the way he looked at me that he wanted me. And, truth be told, I think I wanted him as well. I'd always had th...