Gay Dress Stories

3,413 results
Orientation
Length
Source
Infinite Scroll

Halloween Kink

by toddstop on Aug 18, 2017
Gay Male

"Hurry up, babe, we have to get going," Jared called through the door. I had to grit my teeth and tear my eyes away from the mirror to answer with, "Just a minute." The matching costumes had seemed like such a good idea when I came up with the concept. Now, staring at my reflection, I wasn't so sure. Too late now, I told myself. It was our first Halloween p...

A Very Big Man!

by keptsissy on Aug 30, 2017
Gay Male

Of the men I see regularly he's the biggest. Not just height and weight, his cock is huge, close to 11". And his cock is thicker than any other man I've ever seen. My ex-boyfriend introduced me to him at a party. He told me to go to the bedroom with him and 'be a good girl'. It was one of 'those' parties, all of us girly girl sissies on full display and on t...

Greek Delight Ch. 02

by S_Queen on Sep 25, 2017
Gay Male

When I woke it was morning and I was erect. The sun was up, and I could tell it was hot. Looking over, I saw a slender, feminine body lying naked on its front, face away from me. The back curved into the most delicious ass, round and peachy. I reached out and touched the bottom, the soft skin like marble to my fingertips. I gently squeezed the firm buttocks...

A New Old Friend Ch. 03

by idsweaterguy on Sep 16, 2017
Gay Male

Eric was laying on his back in the middle of the king-sized bed in his friend Jeffrey's spare bedroom. He still had on the yummy ankle-length yellow mohair sweater dress that his friend was planning to post on Ebay later that evening. He was also quite securely bound and gagged. His ankles had been tied together with soft, black bondage rope and so had his...

My Little Rose Ch. 07 Epilogue

by UndertakerKiryu on Aug 18, 2017
Gay Male

A/N: this is the last chapter. There will be a new story soon once I get inspiration to write. This story has been mostly true, or at least based on truth. I hope you like the ending! Question-- would anyone like a sequel to this just about Izaac and Gideon? Epilogue. After deciding an alternative shop was a decreasingly entertaining business, I converted...

One Fine Day

by AnonFineDay on Aug 18, 2017
Gay Male

There have been odd days in every guys life. I mean, from the "average" odd day of some amazing good luck happening or bad luck happening, to the amazingly odd days, like you just suddenly see someone burst into flames, or you manage to actually fool someone so good into making them think you're a woman that they actually fuck you. That was what yesterday w...

One Button at a Time

by Kenderson on Nov 8, 2017
Gay Male

I've always been attracted to hairy guys. In particular, hairy guys in dress shirts. There's something so sexy about a hairy chested man with an open shirt collar. It's such a tease...catching a glimpse of the manliness tucked beneath that thin, tight layer of cotton...a total turn on. One day last June, a very hot and humid day as I recall, I decided to ta...

A Boy's First Piss Enema

by ASIANDREAM on Aug 31, 2017
Gay Male

The Saturday before last, I had an amazing watersports threesome in Hong Kong with a regular fuck-buddy of mine and a "Boy" (only 19) that he'd met. The next day we met up again (just for Yum Cha) and we talked about what we should do for our next session. They were both very much wanting to be able to try piss enemas and so they proposed that we should go b...

A Long Time Coming Ch. 05

by hikertenn on Mar 2, 2020
Gay Male

Doris lived just a few doors away on the same floor as Cal. We timed our arrival so that we were at her door promptly at 5 p.m.. We were both dressed in sport coats. Cal wore slacks, I had on jeans and boots. We were a good looking couple. Cal's elegant conservative style contrasted nicely, (I thought), with my relaxed 'west coast' groove. Doris was a love...

Twink Role Plays Bacha Boy

by Alluring_Crimson_Shifter on Sep 23, 2019
Gay Male

Danny is a slim young man, 18 with no facial hair and very little body hair, fit but not athletic. His friend Jeffrey was going to help him join the fraternity. Jeffrey told Danny there would be an initiation party, but did not mention hazing. Danny and his wife Patty both 18 were married coeds having entered college on scholarships. Both were very smart, b...