Gay Crossdressing Bondage Stories

609 results
Orientation
Length
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Infinite Scroll

The Moment When You Realize...Ch. 03

by funandbold on Jan 8, 2019
Gay Male

Hey guys...I know some of you enjoy this and some of you don't...so I'll give you fair warning! DO NOT READ THESE IF YOU ARE NOT INTERESTED IN SOME VERY SHORT STORIES...THAT ARE JUST DESIGNED TO TRIGGER THOUGHTS AND IMAGES IN YOUR OWN HEAD! Some of these are only a couple of paragraphs and some of them are only a couple of pages...one or two of them took on...

My Name is Dave Ch. 03

by davas on Sep 16, 2017
Gay Male

I did not mean to hit accept. That was the thought that kept running through my head. It had been a bizarre chain of events that I could probably never recreate even if I tried a hundred times. They couldn't hold me to that, could they? I didn't mind getting fucked by Steve, in fact, I enjoyed it and wanted to do it more often. My problem was giving him a b...

Cocksucker: Cocksucking Training

by silkstockingslover on Sep 14, 2017
Gay Male

Summary: A twink teaches a straight man how to suck cock properly. Note 1: Thanks to goamz86, Robert and MAB7991 for editing this story. You do not need to read the first part to enjoy this story. In case you are curious, here is a brief summary of part one called "Cocksucker": Chris, a married straight man, is stuck at the airport when his flight is d...

A Slut is Born

by Luvsishyp on Apr 21, 2020
Gay Male

Special Thanks to madam_tasha for amazing editing and assistance. I sat on the motel bed feeling a nervous excitement. "This will do just fine," I thought to myself, as I looked around the cheap, seedy room. It was relatively clean but had definitely seen better days. The carpet, an ugly pale green, was worn and faded from years of use. An oddly patterned...

Ben is the Subject of an Experiment

by verdunsears on Dec 9, 2019
Gay Male

"Yea, I know Ben, he looks fucking hot, but I tell you, he's a real prick. Any time I see him out at the Manatee or Charlie's or the Quest, he's dancing around like he thinks he's God's gift to lonely faggots. He says he an artist, which means he wasted three years getting a diploma at the College of Art and lives in a loft on Daddy's dime. He's pissed off e...

Exploring my Sexuality

by alexis19901 on May 12, 2020
Gay Male

I'll just start by saying that I've never attended any sauna that may get mentioned in the story. No names that are mentioned are real people either. It's something I've purely put together based on fantasy alone. Thanks for reading! Today was finally the day. I'd been waiting months to go and push myself to try the closest sauna to me which was a short tr...

How Did I Get Here

by bart_allen on Oct 15, 2017
Gay Male

I found Wendy on OKCupid. She was just another face as I scrolled down, albeit a fairly attractive one. I clicked on her profile, glancing over it: she was older than me, which is not usually my type, and she was six years older than I at thirty two. She had a darker natural red hair in shoulder length cut, but a sort of light olive complexion, and pouty lip...

Bathhouse Heaven Ch. 32

by glory_first on Aug 22, 2018
Gay Male

The bathhouse was fairly empty this Wednesday afternoon, a reminder of different rhythms from the past. Following the familiar routine, today with more space to undress than the case lately. The beer was quenchingly cool, and quickly finished. Going upstairs, I walked towards the sling room, noticing a couple of men going different ways than my path. How...

Roommates Ch. 02

by idsweaterguy on Aug 18, 2017
Gay Male

Eric woke before dawn the next day with a raging hard-on. He smiled to himself as he remembered the events of the night before when his roommate, Stephen, had cuffed and gagged him and then stimulated him to the point where he quite willingly had performed his first blow job. He got out of bed and walked into their small kitchen and started the coffeemaker....

Liam's Submission Tested Pt. 05

by PupTracer on Oct 5, 2020
Gay Male

Marcus brought entirely too much food to be defined as a "snack". He had piled on peanut butter and jelly sandwiches, strawberries, cookies, almonds, even slices of cake. When he attempted to precariously juggle it all on one flimsy paper plate, it didn't end well for him. As he lowered the plate to me his rather large boot tapped the edge of the bedframe an...