Gay Crossdresser Stories

41 results
Orientation
Length
Source
Infinite Scroll

My Gay Crossdressing Vacation Ch. 03

by Flame666 on May 11, 2020
Gay Male

I woke up. My bra undone, panties covered in lube and my nylons pushed down my legs. I felt as if I had been used. As I became more aware, I realized that I had been used and really enjoyed it. On the first day at the gay resort after getting dressed, I had walked over to a gay bar and been picked up by a nice guy, named Paul, just a bit older than myself. H...

Catching Up with an Old Friend Ch. 01

by jjdtx on Sep 19, 2017
Gay Male

This story pics up some 20 years later from my college and camping series. Scott and I lost contact after our college days, both moving in different directions and taking different jobs that led us to various parts of the country. Both married, both had kids, and just went on with life. Thanks to social media, we actually stumbled across each other online....

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...

Outrageous Cum Sucker

by Alluring_Crimson_Shifter on Aug 31, 2017
Gay Male

Ricky was on the way back from the Adult store. His cock was already heavy from the conversation with the clerk, and he was anticipating watching the adult movie DVD. For a moment he hesitated, then called his best friend Greg. "Hey Greg, what are you doing right now, I just got another movie. It is supposed to be good. Why don't you stop by so we can watch...

The Bartender Ch. 02

by Pan2 on Jun 8, 2020
Gay Male

As soon as Roger walked through the saloon-style doors, Kent reached for a glass. He'd never before seen a man in such need of a drink. If the dark rings under his brown eyes weren't enough, his incorrectly buttoned-up shirt and mop of dishevelled brown hair clearly used to more attention than it was currently getting were a clear indication that Roger was...

He Knew It Was Wrong Pt. 02

by LoveIsUniversal on Sep 14, 2020
Gay Male

The text message was short and to the point. Bridget wanted him to be with her tonight. It sounded like a fun time, but Zack already had other plans. His text message was also short and concise. He wrote that he had other plans for tonight. He issued an apology in the same text message, though he reassured Bridget that the two of them would get together agai...

Long Hair & Lace Panties

by Obzezzion on Sep 1, 2017
Gay Male

The name's Michael. I'm an Irish boy from nowhere in particular, and the bright-red ponytail I wear is more than enough proof of that. I dress well enough when I need to; my work wardrobe usually consists of black wingtips, tight-fitting black slacks that are a little loose around the knees to allow for bending, and a dark solid button-down. I'm a relatively...

Sex Slave on Death Row

by erectus123 on Feb 6, 2018
Gay Male

[Ever been to the slammer? Not a fun place. But one thing is true, there are no minors in state prison, all sex in prison goes on between adults whether they consent or not. Sometimes it gets pretty hot in the pen and the air conditioning is usually broken.] SEX SLAVE ON DEATH ROW-MY PRISON BLUE BALLS Just my luck to end up in the state pen with a cell mat...

My Gay Crossdressing Vacation Ch. 06

by Flame666 on Jun 9, 2020
Gay Male

I woke up looked at the clock, it was 10 am the sun was out and hot, it was a beautiful day. I rolled out of bed realizing that I had cum all over me, in my hair, in my mouth and leaking out of my boi pussy. I peeled off my 40 D breast forms and headed to the shower. While in the shower, I thought about my plans for the day and the coming night. I remember...

Comfortably Numb

by Nils Huim on Jun 19, 2018
Gay Male

The humiliation was now complete, and Sean was loving it. He was down on his knees on the kitchen tiles wearing nothing but a pair of lace panties, and his wife's lover's cock was in his mouth. It was a beautiful thing to behold (and taste). Long and proportionately thick, from behind its bulbous pink head until it disappeared, at a slight curve, into Gary'...