Gay Crossdresser Stories

41 results
Orientation
Length
Source
Infinite Scroll

Lady Fortune's Smile

by Malice2 on Aug 18, 2017
Gay Male

From deep in the bowels of Hell, the Prince of Darkness releases his hordes of foul, evil and dysfunctional minions bred for the sole purpose of showing up to roommate interviews. And I, Theodore, the legal head of household, must sit here through each horrifying, grueling one on one session with these abominations and remain cordial, collected and most of a...

Learning from Older Men Pt. 02

by letsplayhard1994 on Jun 1, 2020
Gay Male

This tale is a partially fictionalized account of my first time being seduced and sucking off an older man following my introduction into the world of gay sex online. Names have been changed as well as locations but the following story is based off of real events. By the end of 2013 I had discovered that I was sexually attracted to men following a chance e...

Seduced by a Billionaire

by ret123 on Sep 14, 2017
Gay Male

I could not believe it. The woman behind the front desk told me again, "We are sorry sir, but we have no reservation for you and the hotel is completely booked for the whole week because of the meetings and retreat for a major financial institution." "I know!" I said. "I am supposed to attend those meetings and participate in the retreat! Please, help me ou...

My Neighbor's Toys

by married40scouple on Aug 31, 2017
Gay Male

My neighbor, Joe, and I were outside doing the usual weekly lawn care on this particularly hot day. As usual, we chatted about the normal stuff and discovered our wives were away for the weekend visiting their families. He has been married almost ten years and I have been married almost twenty. Joe has a swimmer's build and I am stockier. As we were finishin...

My Fantasies Ch. 08

by bjmichaels on Jul 17, 2019
Gay Male

Turnabout is Fair Play I don't know what it is about me that makes people think I am gay. Sure, I'm only 5' 6" and weigh 130 pounds; am shy around girls and display undue reverence towards alpha males and older men - but that doesn't mean I'm gay, does it? Yeah, okay, I admit it -- I am a compulsive masturbator and some of my fantasies involve men's di...

My Fantasies Ch. 06

by bjmichaels on Jan 7, 2019
Gay Male

Second Night in the Park I was so nervous I didn't think I could go through with it, but I followed him deeper into the trees anyway. What are you doing, John? I asked myself. This guy could be crazy -- he could be a fag-basher -- he might beat the crap out of you -- maybe kill you! Why are you doing this? Why don't you go somewhere you can actually see...

Straight to Bi, Cam to Real Life

by dlcalguy on Aug 18, 2017
Gay Male

After I finished university, I struggled for a good-paying job and money was tight. But I couldn't face living back at home. I managed to find a room to myself in a house-share with two other guys and three women. We were mostly in our early twenties and doing various entry-level jobs. One guy, Pete, was older. About 45. He was on a temporary assignment in o...

Bathhouse Pursuit

by erectus123 on Apr 21, 2020
Gay Male

-All characters mentioned are 18 years or older. There are no minors in a bathhouse. No animals, homeless, or aliens from outer space were injured in the writing of this story. This story is currently being considered for a Hollywood film, it is anticipated that guests at award events will have a choice of vegan meals, peanut butter sandwiches, or pepperoni...

Becoming Mark and Janet's Girly-Boy

by BuckyDuckman on Mar 30, 2020
Gay Male

Who knew taking your turn at washing the dishes could turn sexy? That's exactly how it started as Janet squirmed up close to me, wrapping her arms around me from behind and pressing her chest against my back. I might not have had hands on my back but I swore I could feel her stiff nipples poking me. "Hey baby?" she cooed, kissing the nape of my neck and se...

My Fantasies Ch. 09

by bjmichaels on Jun 1, 2020
Gay Male

Happy Hour So my friend Freddy and I were seated at the bar inside 'Swinging Dick's Saloon' and this gorgeous hunk-of-a-man approaches us and blurts out, "Which of you queen's wants to blow me?" I am taken aback by his brash crudeness but Freddy instantly becomes all giggles, raises a limp-wrist and squeals, "I do -- I do -- I do...." Good God, what a fla...