Gay Crossdresser Stories

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My Gay Crossdressing Vacation Ch. 02

by Flame666 on Apr 21, 2020
Gay Male

We pulled into the parking lot, Paul kissed me again and told me that they would pick me up at 9:30 the next night for our date and tour of the gay bars. I got out of the car and started to walk into the resort but noticed that the bar was closed and I was hungry. There is a Circle K about 2 blocks way and I decided to walk over and get some cokes and some e...

Second trip to the Dream Boutique

by toddmac781 on Apr 3, 2019
Gay Male

This is a true account of my second trip to the Dream Boutique. A Friday night, after doing some work with friends, my horniness got the best of me. I pulled up to the Dream Boutique around 1:30 am. It's open 24 hours, far enough from where I live, and always frequented by horny guys looking to get off. I went to the cashier to get a two dollar bill that...

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...

Bathhouse Observations

by glory_first on May 12, 2020
Gay Male

The baths are undoubtedly the easiest place in a city to have male group sex, after allowing for individual circumstances during any single trip. After more than a hundred visits over the last few years, basically all of them involving satisfying sex with other men, often writing about the experiences afterwards, leads to a few general observations. Visitin...

Bike Night

by Raptorcat on Aug 18, 2017
Gay Male

Being Bi is not something you let be known when you are a male biker hanging out with guys that party with the Outlaws and other one-percenter clubs. But, Bi I am and have been for my whole life, so I've learned when and where to let the secret out. The club I was riding with at that time would do all of the usual poker runs as well as the weekly Friday nig...

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 Joys Of Crossing Over

by Darla Leslie on Aug 18, 2017
Gay Male

It all began back in my teen years in the mid-west when I was just a young, confused lad of eighteen. I was a relatively good looking boy, long blonde hair about 4 inches below my shoulders, 5 feet 11 inches tall, 170 pounds, green eyes with a VERY well endowed girl friend whose body of 38DD-25-36 I enjoyed, admired and envied ---- envied because I'm a close...

Bathhouse Roles

by glory_first on Sep 14, 2017
Gay Male

Arriving right at the bathhouse's opening time on Tuesday, the sky dark enough to think that rain would be arriving soon, the entrance was busy. 5 stacked bundles of the latest edition of a free local gay magazine were outside the door. Going in, before I could mention the delivery, a man with a blue t-shirt that read "I like face fucking - ask me" brushed b...

My Gay Crossdressing Vacation Ch. 01

by Flame666 on Apr 21, 2020
Gay Male

It was mid-January and I was getting tired of the cold and I was horny so I started to think about planning a gay vacation. After a lot of thought I decided on Palm Springs in Mid-February. A bit about me, I am a straight looking and acting man 60 years old slim and fit. However, I love cock and like to dress up in panties and other lingerie. A few years ag...