Gay Dress Stories

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Orientation
Length
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Infinite Scroll

Naked Boy College

by LKFinStar on Nov 3, 2020
Gay

Welcome to Nathan Boyd College! At this esteemed institute of higher learning, we are dedicated to helping our students thrive academically and preparing them to change the world. Now, this college is quite different from many others. As a private institution, we have long been an all-male school, both in our student body and faculty, and continue to be so....

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The Sauna Ch. 02

by jaygreenx on Sep 14, 2017
Gay Male

All rights reserved – this story is a work of fiction and remains the property of the writer. I returned home the next day. My wife wasn't home so I dropped my bags in the bedroom and went to take a quick shower. The hot water, soapy lather, and my wandering hands reminded me of my adventure on the road. As I became hard, I slipped my finger into my tight h...

My Wife's Boss Ch. 04

by jaygreenx on Sep 25, 2017
Gay Male

All rights reserved - this story is a work of fiction and remains the property of the writer. When Friday finally came, I hurried home after work to get ready for our dinner party. I hadn't spoken to Heinz since Ann & I had left his house earlier in the week, and I couldn't think about anything else. Every day at work I was hard, and wanted to make myself...

Bride of my Father-In-Law Pt. 03

by RSchwuler on Jul 13, 2020
Gay Male

Standard warning that appears in all my stories: this is a very over the top, far-fetched work of fantasy. It contains lots of humiliation, light feminization and taboo sex between a man and his father-in-law. Please skip if it's not your thing. Otherwise, enjoy. -- I looked at the bedside clock. It was 6:30pm. I had arrived at Roy's penthouse only an hour...

Blowjob in a Housemaid dress

by DavidHeart on Jul 10, 2020
Gay

There you are. In the bathroom of the hotelroom you took to explore your kinky side. You always wanted to know what its like to suck a cock and take a load. Something about Dicks seems to mesmerize you. Because of that you decided to take a hotelroom over a weekend and see if you find a seizable cock to blow the night. To top if of you even bought a housemai...

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The Bartender Ch. 02

by BothWorld on Sep 2, 2017
Gay Male

Chapter 02 The hustle It was a Wednesday night. There is nothing deader than my bar on a Wednesday night. We did all our business on the weekends. I'm sure Pete would rather close the place during the week if he could get away with it. But he couldn't, so here I was watching three drunks nurse their beers. It was about an hour before closing when he came...

What goes around...

by eastrockies on Jan 21, 2020
Gay Male

Well, there's not a part 3 exactly. After my last encounter, I did what I always do. I chickened out and eventually Denny quit trying to fuck me. I found a gf, another one with huge tits. We'd make love but always end it with me straddling her chest. She squeezed her big tits around my cock and then I'd cum all over them. She was always careful to close he...

The Bear and His Cub

by BigWig69 on Aug 18, 2017
Gay Male

I received a text from the bear, late one night in summer. The message was simple and to the point. Meet me at my place. Shave your cock, balls, legs and ass and if I find a single hair, I'll spank you blue. Dress according to my instructions; I want you wearing white nylons, tight, hip high. A white cotton thong, a super short plaid school girt skirt, gree...

Mel Takes My Manhood Pt. 04

by RSchwuler on Jan 22, 2020
Gay Male

Standard disclaimer: this story is a very over the top work of fantasy, and it contains extreme humiliation, blackmail, and unsafe sex practices. Enjoy! -- The first two days after my gym experience had left me limping painfully with each step. I still met Cliff for personal training sessions in just a jockstrap, but luckily I had not been ball-busted agai...

Fantasy Toy

by margo_x_x on Aug 18, 2017
Gay Male

To the ones who like gay stories, please forgive me if I've botched this up. I'd like to know if I've missed the point for this kind of story, and I'll try not to feel hurt if you'll tell me where I've gone astray. Of course, if you like it, I know I won't be hurt if you'll tell me. Remember, for us unknowns, the voting does little but give us whiplash when...