Gay Crossdressers Stories

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Fixing the straights

by cdbaby on Dec 28, 2016
Gay

You wake up and prepare for your day, unaware that this would be the last day you would be considered straight. You shower as you did every morning and felt the water's warm touch as it cascaded over your skin. You could stay here forever if you could. But you need to start your day and the hot water would run out before long. You wash your hair, then the re...

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Riding on Tickets

by JJEroticas on Dec 25, 2019
Gay Male

Sean's Ride I always wanted to see Abe Lincoln's bloody pillow. I loved trains. I found this Silver for Younger website. An 85-year-old retiree decided to fly down to Savannah and ride back with me. I paced the blue carpet watching incoming jets through the glass. Greg wore a bright pink shirt and a red hat. I greeted him. He was with Chris, his friend, a b...

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 CD Slut

by eljayb on Jan 23, 2019
Gay Male

Sweet encounters As a sexually active 77 year old I have recently been attracted to the lovely world of Crossdressers. Not that I wish to dress myself but I enjoy the company of those who do. In my travels I found this interesting personality called Chrissie. Age 64, CD/TV/TS. After we exchanged messages and emails for a while, I felt we might get on well...

Drag Queen and the Indecisive Guy

by jim_janes on Jan 16, 2019
Gay Male

Walking down the steps my mind was at war with itself. My two personalities were screaming at each other. I have always had debates in my head. I envy those who know what they want or know what must be done without hesitation. I was never that lucky. Every decision was a WWE match between my ears. Indecision was my middle name. Mostly the internal argument w...

The Deal

by emari on Aug 18, 2017
Gay Male

This is a sequel to my story in Transsexuals & Crossdressers, 'Rush', but reading that probably isn't that necessary to understanding this. ~ When one of the Delta U seniors had texted Matt that morning to let him know that the pledges next task would take place this afternoon, and it would involve streaking the campus, with the fastest finishers winning t...

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...

A Night to Remember

by IrishJamesHot on Aug 18, 2017
Gay Male

A fair number of years ago, I was about 19 or so. I had recently finished school and got myself a handy job. Making money and being young, I of course began heading into town (Dublin) on the weekends for some very enjoyable nights out. This night, was one to remember. I had been drinking with some friends in a pub. Last orders were called at bout 2:00a.m....

Finally, Fucked

by Willing2Do on Aug 18, 2017
Gay Male

Cockwhore that I am I have been giving these two guys blow jobs on a regular basis. Actually I suck them, mouth their balls, rim them, and they often fuck my pussy mouth. Though different both of them have nice cocks. One is married and older, in his 40s. The other is single, 20-something-year-old. The married guy's cock is average - 5-6" long, about 4" ar...

The New Order Pt. 01

by Iamkrazy4 on Nov 4, 2019
Gay Male

Part 1: A Bottom's Duty Political strife. Riots. Violent crime. Impending war. These thoughts were all far from my mind as I slowly moved my dildo out of my well lubed ass in my dorm room. I bucked my hips to meet every thrust of my hand as a video compilation of huge clocks flashed across my laptop screen. Finally...it happened. I had a huge orgasm and I...