Gay Shemale Interactive Stories

101 results
Orientation
Length
Source
Infinite Scroll

Escalation

by johnbaldwin1 on Jun 26, 2019
Gay Male

Marc's foot wouldn't stop tapping as he nervously sat in the back seat of his ride share. He was almost at the hotel already, filled with apprehension. He wasn't sure if he could go through with it. It was one thing to play around online, quite another to bring it into the real world. This was the culmination of something that had been building for months. T...

Putting Myself Through College

by RobXXX on Aug 31, 2017
Gay Male

Going to college had always been a dream of mine, growing up in a working class neighborhood had been all the inspiration that I needed to study hard and get good grades throughout school. I will never forget the day that I received my first acceptance letter; it was like a dream come true. Four more followed, in total five of the eight that I had applied to...

Tales of Dick Ch. 17

by Bjsroxxs on Sep 14, 2020
Gay Male

Two days after Daniel had come over, I was working at the shop when Max came in. There weren't that many people in the shop and I had another employee by the front window setting up some boards. Max walked up to the counter where I said, "Afternoon, Max." "Afternoon to you too, Dick," he replied. He wore black skinny jeans with a white sleeveless shirt. The...

The Incest Game

by Ezekiel_Coles on Aug 22, 2017
Gay Male

"You are such a little slut," Jess giggled to me as my eyes rolled over her father's ass. It was her sister's wedding, and we were stuck in some rec centre with no air in the middle of Scarborough on a hot summers day. To pass the time we were playing the family edition of our favourite game: Who Would You Fuck? Jessica and I had met at university and hit i...

Finally My First Time

by bisibi on Nov 21, 2017
Gay Male

This is the story of my first time with a guy. My name is Simon and I'm 25, 5'10" 13st with a slightly athletic build. I had been bi curious for a long time, I watched a lot of gay and shemale porn and experimented with butt plugs and dildos while masturbating. I first became aware of my sexuality while watching straight porn and being slightly jealous of th...

What Would Eve Do? Ch. 02

by StiffClit on Aug 18, 2017
Gay Male

Dallas closed his cell phone and looked down at Luke who had a broad glistening grin spreading slowly across his face. Luke's lips were coated with his cream and looked delectable. Dallas squeezed the head of his cock forcing the last drops of paste to surface on its top. Luke leaned forward, his hot tongue eager to slip into the slit and lap the last drops...

Rainy Day in Tokyo

by KeithD on Jan 29, 2019
Gay Male

There had been rain off and on all day, and it started up again as I was walking from the theater in Tokyo's Ni-chome district of Shinjuku, so I dipped into a small grocery store entered by a foyer in a small apartment building. The deluge, although heavy, hadn't lasted long, and I could use some snacks for the hotel, so I walked the aisles of the store in s...

The Path Not Taken Pt. 01

by jcsbiguy90 on Mar 18, 2020
Gay Male

Note: The following begins as a true story of how I lost my virginity (anal and otherwise) to two gay top daddies when I was 19. Now, 10 years later, I look back on this experience and fantasize about what could have been if I had just embraced my inner cock slut...and the result is this story series. The first installment will cover the true events and tran...

Admitting My Secret Ch. 02

by HerLittlePiggy on Oct 22, 2019
Gay Male

Chapter 2: Gang Bang "Get on your fucking knees pig," the powerful Dom demanded. I was naked in Master Steven's basement dungeon. My wife Julie was fully dressed and sitting in a chair in the corner of the room watching me submit to a man. I was not gay, but I have always been very submissive and I had recently accepted my bisexuality. My eyes flashed at...

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...