Gay Cross Dresser Stories

3,450 results
Orientation
Length
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Infinite Scroll

A Bear Seduction, the Outfit

by wildrideagain on Sep 15, 2017
Gay Male

The kids let me in and I went down stairs to watch the game. Kevin was the only one down there. I took my place in the recliner just before kick off. "Where is everyone?" Kevin nods for me to sit next to him so I get up and take my seat. Kevin immediately leans over and starts kissing me. I kiss back and lean into him like a high school girl. I push my hi...

Rewriting Singularity Ch. 09

by el_wing on Sep 14, 2017
Gay Male

I don't know how long we held each other in that bed. The house quieted. My heart stilled. Our whispers muffled until I fell into a deep sleep wrapped in his arms. My slumber was confused yet untroubled-- laced with two reoccurring dreams: one, a dream I'd had since adolescence where naked men throw pickles at me (big, fat koshers-- not the dainty gherkins...

24 Exeter Place

by sr71plt on Aug 30, 2017
Gay Male

"Thank you," the monsignor said as I handed him down from the carriage in front of 24 Exeter Place in a quiet pocket garden not far from Victoria Station. I had told him my name was Luke, but he'd managed to go all afternoon without directly addressing me—like I wasn't wholly there. This was the first time he'd thanked me, though, and I thought there was rea...

Turning

by Willinglywantin on Aug 18, 2017
Gay Male

Hi, my name is Rick. I had just started working 3rd shift at the plant. We were given computer access, and were allowed to log into myspace, which made the nights go quicker. Jennifer was interesting. She was a self described, big, beautifully dominant woman, that worked as an assist manager at a motel. Her relationship was, "complicated", and she had "spe...

Learning to Love my Body

by cinnabutt on Aug 18, 2017
Gay Male

Having been raised in a single-mother household, I had no father figure around to explain things around me or to emulate, which left me very confused about a lot of things in life but especially my gender role and sexuality in general. Some time after I hit puberty, along with acne came another unexpected change: I noticed my breasts were growing, and worse...

Cross Dresser Escort Swallows Cum

by Alluring_Crimson_Shifter on Apr 3, 2019
Gay Male

The sun felt good on Don's suit and tie. The breeze tussled his well trimmed hair which fell back into place thanks to his hair spray. Smelling the fresh cut grass and the blossomed flowers he pleasantly gazed about the well kept city square. Charismatically he smiled at other walkers whether dressed casual, or in business attire. City traffic noises were ca...

My First Time

by CrazyBlade on Apr 3, 2019
Gay Male

One of the most important things that have ever happened in my life was the first time I was ever with a guy in a situation other than just friends. It is probably one of the most difficult things to deal with when you realize that your sexuality is something other than the “status quo”, something a little out of the ordinary and, in my case, my feelings of...

Craving for Cock Ch. 02: My Hole

by Stevecrowley on May 7, 2019
Gay Male

It's been almost two weeks since I've seen Dwayne and sucked cock for the first time. Now, I find myself staring at the crotch of every older gentleman I see as if they're supposed to whip it out and dangle it in front of my face. This Saturday coming I'm going to go visit Dwayne again and see if he needs my assistance. it's Friday night and I've jerked off...

In-Law Brother Lover

by BoyMistress on Dec 24, 2019
Gay Male

First chapter to sort of set up the story line , before I get into the real shameless smut. Chapters will get raunchier as Brandon gets consumed by revenge to destroy his sisters dream life, he will get more depraved and immoral as the story line continues and so do others characters and I look forward to writing about it. Prologue: This could have all be...

First Experience With A Man Ch. 1

by girlboybootsie on Aug 18, 2017
Gay Male

I wasn't always attracted to men. In fact, until I was 18, I never felt confused about my sexual orientation. In terms of sex, I was only attracted to girls, especially sexy ones who dressed in provocative and sexy clothes. I was popular with girls, and had lost my virginity when I was 14. Without meaning to be immodest, I was, and am, a very good looking gu...