Gay Crossdresser Stories

36 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

First Time Anal

by iamcontent on Sep 14, 2017
Gay Male

I have always known I was bisexual since I was a kid. I have topped but never bottomed, I have attempted bottoming a few times. First time I was in my teens and my friend and I tried, we didn't have lube and I wasn't stretched out properly. A few months ago I bought a butt plug which is 4 inches long and a 8 inch dildo. I lube every night and put the plug in...

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...

Julian entdeckt Julia

on Jun 16, 2018
Gay

Mein Name ist Julian und ich bin 19 Jahre alt, schlank, sportlich. Vor ein paar Monaten bin ich nach meinem Abitur von Zuhause ausgezogen um zu studieren. Schon kurz vor meinem Abitur entdeckte ich beim, fast schon alltäglichen, Pornodurchstöbern mein Interesse für Crossdresser Pornos und Videos, in denen süße Twinks von reifen Männern vernascht werden. Nach...

Open in Reader

I was Hard on Nude Beach

by LucyFrance11 on Mar 6, 2018
Gay Male

I live in a naturist complex in Leucate in the South of France and whenever possible when I go on holiday I look to stay in places that have nude beaches. I get so aroused being naked and showing off my shaven body to anyone who likes to look. I am in my 40s, 6ft tall and slim as I exercise a lot. I am also gay and a crossdresser but more of that in later st...

Abused by a BBC

by Experimental901 on Oct 24, 2018
Gay Male

Thank you so much for reading my first written submission! I've wanted to write erotica for years now but I've never really had the courage or the time to get started, until now! I realize I may have some work to do and I would gladly accept any advice or future story requests that you may have! * I had always considered myself straight. I'd had a few girl...

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...