Gay Crossdresser Stories

41 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 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...

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

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...

Open in Reader

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...

Daddy's New "Wife"

by Shadow Shark on Dec 4, 2019
Gay

Hello! My name is Tristan Wood, or Triss as my friends and family like to call me. I'm 22 years year old, recent college graduate, and unemployed. Right now I'm living with my old man Harry Wood, he's a thickset man in his late 40s. Though, pops has been living in constant sadness since mom passed away seven years ago. At first, he barely bothered to do anyt...

Open in Reader

Complete Control

by vicw1392 on Apr 27, 2014
Gay

James had read, and seen, porn about men who could change the world, and that's what he'd been doing last night. After a quick, and mostly unsatisfying, wank, he'd fallen asleep wishing that there was more of this type of porn for gay men; where was the fun in reading about unlimited possibilities if all the characters do is make everyone's tits bigger? Then...

Open in Reader

Incubus

by kalanac on Jul 14, 2017
Gay

You stand in the formless void of hell, having been summoned by your master. You recently got promoted above the rank and file demons that torture the unlucky denizens of this infernal realm. "Are you ready to go into the mortal world?" a voice booms from the darkness around you. "I am, my Lord" you say. You've worked hard for this promot...

Open in Reader

Sissies love big black cock

by Yelawolf on Nov 16, 2017
Gay

Welcome to the story you crazy sissies and you strong aphla black males. This is from edithis and I want to bring here so you guys can write or read or for the real reason you're here to masturbate. Get your hand, dildos, lube, and whatever else you need to jerk it off. Time to begin the story up. (Thanks for all of the likes and support on this story. I jus...

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...