Gay Crossdresser Stories

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Crossdresser's Unexpected First Time

by kprice1984 on Nov 27, 2017
Gay Male

Just want to say firstly, that this story is 100% true. Secondly, it was much better in person. I'm just getting around to writing it after several years. ***** I'm a 20 year old guy, very good looking, easy to get girls. Brown hair, green eyes and a sexual appetite that's hardly ever satisfied. I had always had a craving or tendencies towards being a lit...

How James and I Started Together

by CrossdresserAlison77 on Sep 16, 2017
Gay Male

It was a Friday night in southern California. I had been checking the Craigslist.com M4M section recently and found someone to respond too. After a long back and forth conversation, and a nervous wait, we finally met up. All he wanted to do was give me a blow job, but our night ended up going a little different. My name is Alin, and this was the first time I...

Friends of Friends Pt. 02

by bi_cpl_with_crossdresser on Jul 15, 2020
Gay Male

Jack could feel hands massaging his as cheeks before spreading them open to reveal his tight little hole, then he could feel the coldness of the lube running down his crack as Marcus opened the bottle and let some pour out. The coldness was broken by the warm fingers now leading the lube to where it was needed to be and Marcus just massaging the puckered lit...

Friends of Friends Pt. 01

by bi_cpl_with_crossdresser on Jul 15, 2020
Gay Male

It was a Saturday night and Marcus and Jack were lying in bed after yet another marathon fuck fest. Jack had still not cum yet and Marcus was helping him along with a handjob. It wasn't too long before Jack was blowing his load all over his stomach and Marcus's hand, Spent Jack let his head back down to the pillow and closed his eyes. When he opened his eye...

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...

First Time Tasting Real Cock

by traploverr on Aug 17, 2017
Gay Male

Quick introduction for myself - I go by Cindy and I am a bi-curious crossdresser who is currently in a straight relationship. I started with some self anal play but slowly found myself lusting after a real cock at some point. I've had many fantasies but this is my first time having a sexual encounter with another man. Hope you all enjoy! I was on a business...

Sarah Visits a Gay Spa

by SarahCD on Mar 3, 2020
Gay Male

Most of the time I'm dressed as a girl. I am a crossdresser. I only every wear girls clothes even when I appear to be a guy. A black t-shirt and jeans looks male even if the label says size 14 or has a designer name. I normally like relationships with other girls like me. However, I do like sex with men. I call it 'Afternoon Delight'. No commitment, no strin...

My First Guy in the Park

by Tonisshy on Aug 18, 2017
Gay Male

Briefly this is me, I'm 24, 5'5" and 126lbs. My hair is long dark brown and my complexion is natural tan from my native heritage. I've been a crossdresser ever since I was born. Period. Now that I live on my own I have all sorts of outfits, makeups, shoes, breast forms and toys. I just have one thing I have never done. I've never been with a man. I've fa...

Girl of the Group

by leviathanic on May 15, 2019
Gay Male

I'm Noah, a fem 23 year old guy from New York. I'm kinky, an on and off crossdresser, and I think I'm obsessed with men. I love how they look, their mannerisms, the aura the exude, and the feeling of total contentment I get from submitting to them. A couple months ago, I met a handsome 26 year old dom guy on the internet. He was from Pakistan and I learned...

The Warden and his Captive

by levyn on Aug 22, 2017
Gay Male

{Disclaimer: this story contains a transitioned ftm - female-to-male gay character. However, it's not classified under "Transsexuals and Crossdressers", as the author sees this as a gay erotica story regardless. If this does not suit your tastes, please do not read further. If you -do-, enjoy yourself! ] ( He had been waiting there all night. T...