Gay Dress Stories

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First Experience With A Man Ch. 2

by girlboybootsie on Aug 18, 2017
Gay Male

Leading me into his bedroom, I find the sexy pink corset, panties and stockings that he bought the other day at Frederick's all laid out, on his bed. There is also a pair of silicone "boobs." "I didn't even have time to give it to Jessica, so you can have it. I'll leave you alone while you change. You will need to slip the boobs into the cups of the corset....

No Solicitors Allowed... Well

by lovetoshowit on Jul 31, 2019
Gay Male

It was a Tuesday and when I got home I found that my wife was going to be gone for a little while. As was my habit when she was gone I slipped into sompanites and a short strapless sun dress, with a set of 4" heels. I loved to walk around like this, and in our neighborhood, it was not unusual for people to be going door to door to try and sell different thin...

My Little Rose Ch. 02

by UndertakerKiryu on Aug 18, 2017
Gay Male

Authors note: sorry for the wait. The last version was rejected for smut. And the one afterwards. ***** I lay in bed naked and panting, feeling the traces of orgasm pulse through my veins, better than what usually pulsed through there. I turned over and saw the sleeping face of my boyfriend of six months, Garland. His naturally feminine features were beaut...

It's Not For Me

by gladys100 on Aug 18, 2017
Gay Male

It's not for me, Simon was walking to the underground from a meeting in Soho, he stopped outside a sex shop window, captivated by a stunning rubber clinging short dress, he was imagining wearing it, a young man came up beside him pushing a bicycle, "That's fabulous is it, it would look great on you" "It's not for me," Simon mumbled going red. "Oh, undo...

Simple Submission

by LoveIsUniversal on Apr 10, 2018
Gay Male

Heidi had a good life here in Southern California. At the age of forty-three, she had a good job and a lovely house. Living in the city of Arcadia was almost the equivalent of an island paradise. She had friendly neighbors who reminded her why she stayed in such a quiet and clean suburban community. They were good people, the kind that never overstayed their...

James and Sam Meet Up Town

by thameswatcher on Jul 13, 2020
Gay Male

James and Sam had been emailing late at night and three weeks later an opportunity came for a meet at James flat at The Borough, so Sam found himself on the train at 7pm carrying the dress in a large suit bag. He'd never been to Jame's and was looking forward to seeing his place. He followed the directions and soon found himself at street level and waiting f...

Playing Dressup Ch. 01

by mfs1390034 on Jan 21, 2020
Gay Male

"Sure. Why not?" I said and we went upstairs to his parents bedroom. My best friend and I had watched several YouTube videos about men who dressed up in women's clothing and, after helping ourselves to his parents liquor cabinet, we decided it would be fun to try on his mom's clothes. At first we tried on her wraps and coats and had fun drunkenly strutting...

Must Be My Lucky Day

by LoveIsUniversal on Sep 14, 2017
Gay Male

He didn't move. He just sat on his girlfriend's bed and kept his eyes on her open closet. Eighteen-year-old Edward had only one thing on his mind. But his girlfriend would never accept it even if she was more open-minded than anyone else. The young black man tried to repress his temptation, but it always fought back and sought its victory. One look at Cheryl...

Intruders in the Night

by LoveIsUniversal on Mar 13, 2018
Gay Male

Terry just wanted to sleep, but he couldn't. He lay flat on his bed and he couldn't even manage to close his eyes for an extended period of time. He checked the time on his smartphone. It was two-thirty in the morning. This sort of thing happened before. He would try to sleep, but his imagination would take hold of him and have him think of things that other...

Becoming Daddy's Girl Ch. 01

by Sungmehetu on Mar 6, 2018
Gay Male

Editor's note: this story contains scenes of incest or incest content. ***** It might have been the death of my mother and my only sister in the car accident. It might have been that I tried to drink away the depression while I was hundreds of miles away from home at college. What I do know is two things. My father would be furious I had failed out, in jus...