Gay Crossdresser Stories

23,018 results
Orientation
Length
Source
Infinite Scroll

Six Hours of Heaven

by diablofire on Sep 15, 2017
Transsexuals & Crossdressers

Authors Notes: This is the story of my first visit to an anything goes swingers club in Las Vegas. The night of the story I was one of the first arrive and one of the last to leave. ***** I finally sat down with my wife yesterday afternoon and had a talk with her about my desires to take my sexual desires to the next level and I was surprised what her resp...

Forced Gay by Two Women

by fun4all6969 on Sep 11, 2017
Fetish

I told Nikki about an upcoming business trip to the Las Vegas area, and how I'd be interested in meeting with her for a strap-on and simulated forced bi session and that I would be willing to be generous. Nikki started out with one dollar figure, which then increased she said, because Jenny her friend wanted to play too. Then when I asked about rules, she sa...

Curtain Up, Knickers Down

by Sweetlisatv on Sep 16, 2017
Transsexuals & Crossdressers

Every year across the area I live we get the amazing Rocky Horror Picture Show at the theatre and it is always an amazing chance for me as a crossdresser to get out dressed to an event with friends some straight and up for a laugh others trans, bi and gay. As we booked the last night of the show and had a group of 6 of us going we had agreed to meet in a ve...

Brotherly Desires

by fuzzie_writer on Sep 16, 2017
Transsexuals & Crossdressers

James heard the doorbell go, and opened it to find his neighbour standing there with a smile. "Hi James, I'm wondering if I could ask a favour? My broadband's down and I have some urgent emails to send. Would I be able to use your computer for half an hour?" "Sure Dave, come on in and I can help you out!" Dave grinned at him as he squeezed past. James had...

The Transformation of Ms. K

by parkerkwon on Feb 25, 2019
Transgender & Crossdressers

By day I'm an average Korean guy, a bit on the fat side, my whole life I haven't been very attractive to women. I'm very timid and shy as a boy, very much a beta. I never even had sex until after college and my dating life has always been pathetic. I've always had a bit of a tight rubber and latex fetish, as I became older I began buying some pieces of lat...

Jack's First Time

by bi_cpl_with_crossdresser on Jul 13, 2020
Transgender & Crossdressers

There were no secrets between Jack and Marcy, hell when you have been married to the same person for almost 24 years and together for even longer there was no need. Marcy had professed to Jack well before they were even a couple that she was bi and soon after they were dating Jack confessed he was a Crossdresser, a few years later he also said he thought h...

Male Model Nude for Money and Sex

by MotherandSonTrueConfessions on Oct 7, 2019
Exhibitionist & Voyeur

After modeling naked for women that he knew, years later, modeling nude while in college brought back fond masturbation memories. Author's Note: This is a true story about Dave, a proud crossdresser who goes by the name of Kelly when he's dressed as a woman. A submissive male with a medium build and feminine features, at 5'6" tall, when dressed in drag, mo...

Sarah was a Bad Girl

by SarahCD on Jan 8, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some...

The Sting

by estragon on Sep 1, 2017
Humor & Satire

Who stole the stories from Literotica.com? Here's one answer. Huang Meili had a rare place for an eighteen year old girl--she was a Senior Research Fellow at the National University of Defense Technology in Chengsha. Ostensibly she was a database manager, developing software for better tracking spare aircraft parts and maintaining records for naval personne...

Going Gurly Ch. 01: Cara's Clitty

by anna_subCD on Sep 16, 2017
Transsexuals & Crossdressers

My stories are all true recollections of events from my life, as accurately as I can remember them, with two exceptions: 1. The names of my partners have been changed for their privacy; and 2. I have omitted any references to safe sex, because reading about people fiddling about with condoms is not to my mind very sexy, and in stories you don't need to be...