Gay Cross Dressing Stories

3,703 results
Orientation
Length
Source
Infinite Scroll

Pony Boy Ch. 09

by ChestersBoi on Sep 14, 2017
Gay Male

The story so far... Ben, desperate for a little extra cash, discovered that there was good money to be made running in races as a 'ponyboy'. Despite being assured that the worst he would be subjected to would be a 'certain amount of groping' he has found that this led, inexorably, to a life as a prostitute. Moreover, Andy Mason, his pimp, along with Archie,...

How I Became a Sissy Slut

by DixeenormousToo on Sep 15, 2017
Gay Male

I wish I knew I had these sissy urges when I was younger. Who knows, instead of getting married, having kids, and living the "American Dream," I might have discovered hormones, worked my body into shape, and become a tranny porn star. After all, how often does the American Dream really work out anyway? I'm unhappily divorced, my oldest is on his 6th year of...

Bonds Unbroken Ch. 04

by Cia81 on Sep 19, 2017
Gay Male

The next day brought little change to Natham's condition. He was still heavily medicated but had stopped hissing at the staff and let them touch him in order to help him without being sedated. I sat with him for a few hours. He kept waking up when I shifted but after a quick check to make sure I was still there, he would knead my hand caught between his, pur...

Discovered by a Black Guy

by chastity_sissy on Sep 14, 2017
Gay Male

I should preface this story by saying I've never identified myself as homosexual, but sometimes after being locked up in chastity for a long time combined with crossdressing, I must admit to some fantasies involving other men. I never expected anything to ever actually happen, and it's my own fault really. I had been paying a beautiful, very sexually fetis...

Maraschino & a Muse's Cherry

by soupwarsproject on Aug 18, 2017
Gay Male

My boyfriend is going to cheat on me tonight. I just know it. He’s such a whore. Lobo claims that he’s only going to try to get his high school pal to do a little figure modeling. I know better. He’s normally not interested in women at all. However, he’s told me before that he doesn’t really consider her a mere woman, but his ultimate muse. I’m certain that...

Rick Needed a Beer, Gets Much More Pt. 11

by Iwanttwo on Aug 12, 2019
Gay Male

This chapter may better fit in the cross dressing category, but I'm keeping it in Gay, as past and future chapters are gay stories. And this chapter does involve some hot gay sex. I recommend you read previous chapters first, if you haven't already, to understand the characters. —————————————————— Tuesday at the office was awkward, to say the least. I avo...

Auditioning for the Harem

by Coxswain on Aug 18, 2017
Gay Male

A pocket-palladium, the Monde Elegante nightclub was the premier show club in the city. Also one of the oldest. The neighborhood when it was built was a genteel part of town occupied by the comfortably well off. Passing years had changed the demographics and the median income of the area, and the Monde Elegante had deteriorated, too. The building could use a...

Gay Ride Ch. 02

by groove_kid on Sep 15, 2017
Gay Male

Terry was the first experienced gay man I'd been with. Though sex with Michael was still hot as fuck, Terry just knew more. I saw Michael the night after my Terry episode. I couldn't help but tell him all about it, and he was knocked out. "Wow babe, You're really getting wild! " he intoned. "Well I'm just experimenting. I thought that's what me and you we...

Suck Thy Neighbor

by ret123 on Apr 8, 2019
Gay Male

I am a masculine, aggressive businessman who keeps himself in good shape by lifting weights and cycling almost every day. I am married and have two kids who are terrific. I work hard, make a lot of money and go to church almost every Sunday. I was heterosexual and faithful to my wife until I was in my 50s. My attractive wife is a lot younger than me and we h...

Bathhouse Recollections

by glory_first on Nov 12, 2019
Gay Male

Since that first extraordinary visit to a bathhouse, following decades of fantasizing about what happens there, I have fallen in love with having sex in a nearby male only sauna. There are still fantasies not fulfilled, but the actual experiences continue to be deliciously surprising - and extremely enticing. The baths are a place of freedom, starting with t...