Gay Dress Stories

3,413 results
Orientation
Length
Source
Infinite Scroll

The Fallen Ch. 04

by Acacia_wolf on Sep 14, 2017
Gay Male

Author's note: I will try to explain everything and stuff, and hopefully it will make this part longer. If you've been reading thank you, and sorry for the lack of details in the previous chapters. I hope you enjoy this chapter. All characters are 18 or older. * The ride home was pretty quiet. Tenshi felt an uncomfortable tension from Seiji and his friend...

A Kept Sissy Boy

by keptsissy on Sep 19, 2017
Gay Male

"You need your butt paddled, don't you?" When I responded to his 'Dominant Male' ad I knew what I wanted, what I might be in for. I masturbate to nothing other than being used by a real man. But I didn't know this man would exploit that completely at the time, be as good at it, as addictive as he is, make me his full time sissy 'girl'. It started out two...

The Wild 60s

by hangeron on Aug 18, 2017
Gay Male

I open the door to our suite, laden with packages. You are sitting at a table in the middle of the room, with three other men, playing cards. My expression is a mix of surprise and dismay. "Hi Babe. Umm, what's up?" I ask carefully. "I'm playing cards." You don't even raise your eyes to look at me. "We had plans to go out tonight, didn't we?" I ask, with...

Button Down the Hatches

by Kenderson on Nov 27, 2017
Gay Male

Sitting at my desk that rainy, grey Thursday afternoon, I wondered what the point of it all was. I mean, really...how many times did this one short communication need to be tweaked before it was ready for publishing? A short memo about new parking passes had been back and forth for edits over 8 times at this point. Changes here, changes there. One more chang...

Friends of Friends Pt. 01

by bi_cpl_with_crossdresser on Jul 15, 2020
Gay Male

It was a Saturday night and Marcus and Jack were lying in bed after yet another marathon fuck fest. Jack had still not cum yet and Marcus was helping him along with a handjob. It wasn't too long before Jack was blowing his load all over his stomach and Marcus's hand, Spent Jack let his head back down to the pillow and closed his eyes. When he opened his eye...

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...

Ozark Bitch Pt. 02

by oskarwild on Sep 14, 2017
Gay Male

Caged It was a long night for Patti. He wasn't used to sleeping with someone and Zeke stayed snuggled against him all night with his arms wrapped possessively around his new slave. Zeke snored and he mumbled in his sleep. Patti couldn't make out what he was mumbling, but occasionally "Patti" came through. Zeke dry-humped him a couple of times that night an...

The Awakening

by randyteacher on Aug 18, 2017
Gay Male

On the way home from a party the largest of limos stopped and asked if I anted a ride with my wife. Ania is 28 with a very fit body fit for fucking anyway, she has a nice round arse and perky tits with lovely nipples standing out through her silky dress. It was getting colder as the night went on as this limo stopped. I looked in and saw it was just a young...

One Man's Search Ch. 08

by Tarielen on Sep 14, 2017
Gay Male

Chapter 8 - Woman in the Red Dress A few weeks had passed since Reggie's public appearance and the beginning of Shinji's training. Things had been going fairly well. Reggie took Shinji with him in the mornings now and he had officially offered Shinji the job as his personal assistant, which Shinji was more than willing to do, it gave him an even greater con...

Trust

by Nils Huim on Feb 6, 2018
Gay Male

J complimented me on my balls; he liked that I kept them shaved. I laughed and said I keep every part of my body shaved! I see that, J said, giving my ass a swat. I didn't actually shave my ass, I Naired it. My ass, my lower back, the backs of my thighs...the hard to get-at places. I'd offered to dress fem for J but he said he wanted me masculine. Masculine...