Gay Shemale Stories

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Orientation
Length
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Infinite Scroll

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...

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...

Then and Now

by FredTR on Jun 4, 2019
Gay Male

I could feel my heart pumping as I drove. Butterflies fluttered in my stomach. It was hard not to speed but I couldn't risk a ticket. I pulled off the highway onto the local streets. Red lights and stop signs were the bane of my existence. And the 30mph speed limit! UGH!! I had found this place by almost by accident, a random comment about it on a chat foru...

Discovered!

by Three_Curious on Aug 18, 2017
Gay Male

I had been curious about sucking cock for years, but I always kept it in the back of my mind. When I was really horny, images of getting down on my knees and worshipping a big, hard cock would spring into my mind. I would fantasize about a hard-on pulsing between my lips and shooting spurts of warm spunk into my mouth – and in particularly horny moments, I w...

A Naked Encounter

by Pissdrinker on Mar 6, 2018
Gay Male

Please note that although this is a true story, I have omitted that we used condoms, we always play safe. Despite whatever Lucy may tell you. ***************************************** Sometimes in winter, if we're not travelling, I go for long walks down the beach nearest to our house. Dave, my boyfriend, often stays at home but occasionally accompanies me...

Long Time, No Suck Ch. 04

by Stontstr on Sep 1, 2017
Gay Male

That weekend was amazing. I felt really great about my relationship with Marc. Cloe, Stephanie's girlfriend, turned out to also have a surprise. See, she turned out to have a rather nice penis, a nice extremely large, uncut penis. Cloe had even named it, Clarence. Marc had to go back to town on business for several days, but Stephanie said he knew all about...

An Unquenchable Thirst Pt. 01

by jam7227 on Aug 18, 2017
Gay Male

My story starts like most people's. I grew up in a home where you were told to act like a man. My father would often rant about how faggots were ungodly people doomed to hell. I was taught lusting after a man was the worst thing a male could do. I joined the Marines at seventeen; the manliest profession I could think of. I enlisted into the infantry and was...