Gay Dress Stories

3,413 results
Orientation
Length
Source
Infinite Scroll

Danny Wants Me Girly Pt. 04: Jackie

by alexcarr on Sep 14, 2017
Gay Male

In my last story Danny wanted me to be a slut for him. It was an awesome experience and Danny was really great at making me feel the part, the way he swore and bossed me. And the way he shagged me like a rag doll. But Danny has many moods as I discovered when he said he would call me his girl Jackie - with the very tight ass and slender figure, wrapped in a...

Not All Bulls are Young and Hung Pt. 02

by pjd103 on Jun 1, 2020
Gay Male

We arranged to meet during a late afternoon in the same Premier Inn. Strangely Kath looked more confident. It was Paul who looked nervous, his head bowed slightly with eyes cast downward. I wasn't sure if that was a good sign or not. I explained that they were travelling into unknown territory. I aimed my next comments to Paul, explaining that Kath had asked...

Simon And Sam's Second Weekend Pt. 01

by thameswatcher on Oct 6, 2020
Gay Male

A week had passed and the two mothers where again working combined shifts at the hospital, because of covid they were sleeping in a converted dormitory so Sam knew he had a whole week end with Simon alone. His mother was only too grateful that Sam volunteered to look after the boy, and also she'd noticed some changes in him lately, he was showering more and...

Lovely Brunette

by LoveIsUniversal on Mar 21, 2018
Gay Male

In the city of Fullerton, Lisa arrived home after a long day at work. She had hoped to see her husband in the house, and when she walked inside, she heard the faint sound of music originating from upstairs. At first, Lisa thought none of it. But then, she began to recognize the distinct mainstream sound of the song. It was a song performed by Katy Perry, fro...

Truth or Dare

by O.T. on Sep 14, 2017
Gay Male

As a marriage grows you eventually open up and tell stories about things that you would not ordinarily have told. This was the case with my wife. I had made the mistake of telling her about a gay experience that I had had earlier in my life. I had explained to her that the situation had happened against my will but that I had achieved orgasm during the act....

Nicole Comes Out

by BlueEyedNick on Aug 18, 2017
Gay Male

In the early days of chatting online, so many years ago now, I used to chat a lot in various kinds of sexually themed chatrooms. More often than not I chatted under a female screenname. I've always had a very strong feminine side and I was good enough to get away with it. Under the various female names I used I chatted with men and women alike. Usually it wa...

Playing Dressup Ch. 02

by mfs1390034 on Mar 18, 2020
Gay Male

Jeff and I spent the entire week at school without discussing what had happened. How I had dressed up in his mother's clothes, which turned him on so much he asked if he could jerk off to me. How one thing lead to another and, before we knew it, we were jerking off to each other and even tasting each other's pre-cum! I didn't feel wrong about it, I was actua...

Jo and Mike

by skinnysailor on Nov 12, 2019
Gay Male

I've got the perfect job. I'm an interior designer at C###### the nationwide premier designer builder of exclusive homes. I mean, if your dream home will cost less than two million, don't even bother calling. Right? I mean, where else could a five foot tall, third generation Vietnamese Canadian, be allowed, even encourage to wear eye liner and nail polish t...

Co-worker's Man Ch. 28

by rmdexter on Sep 14, 2017
Gay Male

"Okay cocksucker. I love your enthusiasm but let's save it for lunchtime. Now you better get that cum-filled ass of yours into work," Mr. Wolfe said. "I'll be waiting outside at noon." I let his beautiful cock slip out of my mouth and got off my knees. I grabbed my overnight bag and headed out. My legs were shaky from my recent fucking as I made my way to my...

Costume Party

by caughtsinning on Sep 25, 2017
Gay Male

My wife and I had been invited to a friend's costume party in mid-June. It was a perfect night for an outdoor party. The air was warm, not too humid and the camp fires around the property kept the dampness and chill out of the air. There were people all over the place but the majority were centered around the pool and outdoor bar area. I had been talking wi...