Gay Crossdressing Bondage Stories

609 results
Orientation
Length
Source
Infinite Scroll

Discovered by a Black Guy

by chastity_sissy on Sep 14, 2017
Gay Male

I should preface this story by saying I've never identified myself as homosexual, but sometimes after being locked up in chastity for a long time combined with crossdressing, I must admit to some fantasies involving other men. I never expected anything to ever actually happen, and it's my own fault really. I had been paying a beautiful, very sexually fetis...

Exploring My Bi Side Ch. 02

by bscurious1 on Oct 19, 2020
Gay Male

Randy and I kept up our meetings, sometimes weekly sometimes two or three times a week, just depended on our schedule and how horny either of us were. We always met at his house in his home studio which offered us a lot more privacy and freedom. As I had stated the massages pretty much stopped but he would still give me one when I needed one or just wanted o...

Oddities at Their Most Erotic Point Ch. 01

by orochtong on Aug 18, 2017
Gay Male

Warning: This story contains a lot of appendages and somewhat non-human erotic scenes. If you do not like this kind of fiction, please do not read further. And yes, if anyone got the reference, the methods described in this story allude to Orochimaru from Naruto, except in a more erotic way. Please feel free to leave any constructive comments below--they are...

Naughty Asian Student Punished

by asianspankee on Sep 19, 2017
Gay Male

Foreword: This is a fantasy story containing topics such as spanking, sodomy, interracial theme, rope bondage, gay sex etc. for readers over 18. I originally wrote it for a friend (named Brian in the story) and I'm posting it here in the hopes that you'll enjoy reading it too... * I am a college student renting a room in your house. We have become friends,...

My Gay Crossdressing Vacation Ch. 04

by Flame666 on May 11, 2020
Gay Male

I slowly opened my eyes, remembering what had just happened over the past 24 hours, I woke up looked at the time, it was just before 7 pm. Earlier I had decided to start getting ready for my date with Paul and John around 7:30 so I got out of bed to get started. I was going to start with a shower and because I had a bit of extra time decided to take off my b...

I Once Was Lost But Now Am Found Pt. 02

by eviltwin52 on Oct 5, 2020
Gay Male

In Part 1 I found a friend in Leon. Having lived the greater part of my life alone, maintaining my bond with Leon was the most important mission I'd ever had. Sucking his cock was my way of showing him my appreciation for his comradery. He didn't ask me to do that. He didn't tell me to do that for him either. All Leon did was nudge me in the right direction....

Fun and Games Ch. 01

by Arten10 on Sep 2, 2017
Gay Male

Chapter 01 – Introduction It all started one wet and miserable Saturday afternoon when Leon was bored at home browsing the net. He'd just been looking at a website with some 'ordinary' guys on who happened to be into bondage and liked to be tied up and played with. Leon thought it made an amazing change to see a site with just ordinary blokes on instead of...

New Neighbors Ch. 02

by idsweaterguy on Sep 16, 2017
Gay Male

After Jeffrey's breathing returned to normal and his cock began to soften, he laughed and told me to continue to keep his cock in my mouth. "After all," he continued, "you are still tied up and rather at my mercy wouldn't you say?" I managed a "mmmppphh!" and nodded. I, too, was enjoying the moment. We remained like that for a few minutes—me tied hand an...

My Dream Solution Ch. 01

by Cyanlot on Sep 15, 2017
Gay Male

[Note: This is a long introductory setup to a multi-part story. There is *no* explicit sex in this first chapter. If you are looking for quick, hot read, move on. This is not it. Things will heat up in later chapters, I promise. --Cyanlot] Chapter 1: When I Hit the "Change of Life" When Massachusetts became the first state to legalize gay marriage, Todd a...

Just a Game Ch. 02

by tamgreen on Sep 14, 2017
Gay Male

Pete woke up alone, and the apartment smelled amazing--something delicious was cooking. He tottered unsteadily to his feet and looked down at himself. He was wearing nothing but a t-shirt and a furious hard-on. He pulled on a clean pair of boxers, stuffing himself awkwardly into the fabric tent before trudging to the kitchen. Dean was standing at the stove n...