Gay Shemale Fucks Guy Stories

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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...

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...

On a Run Ch. 01

by yeaimbored on Sep 16, 2017
Gay Male

I bent over to tie my shoe when suddenly I felt a hand on my ass and a voice say, "well what do we have here Johnny?" I instantly tried to stand up, but another hand on my back pushed me back down. "You'll stay there for now, I like the view," the man said as he rubbed my ass through my spandex running shorts. I was terrified, I knew there were at least two...

Internet Holiday

by Sean943 on Jan 20, 2020
Gay Male

My current assignment in Den Haag was nearing completion, time to look for a new assignment; first, I would take a few weeks off. Where would I go, what would I do when I got there. Being a solo traveller has its restrictions. Checking out options on the web, I came across someone looking to share a cabin on a cruise ship. I sent him an email saying, I was p...

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...

My First Visit to a Gay Club

by girlboybootsie on Sep 14, 2017
Gay Male

One Friday night, feeling courageous I decide to do what I have long fantasized about, and go to a male sex club in San Francisco to lose my virginity. I slip on a pair of shiny pink silk bikini panties, which hug my tight buns and wrap a matching pink satin garter belt with lace trim around my waist. I then roll sheer white stockings with French backseams...

Straight Punk

by Rayne Dropz on Aug 18, 2017
Gay Male

I'm a little straight punk. At least that's how I act. You know the type. The guy that has no friends, that thinks he's the shit and you've never seen him with a girlfriend? Yeah, that's me, except I'm in college now. Still no girlfriends but I have a bro. Cool guy. There we were walking home together just shooting the breeze. This van comes out of nowhere...

Black Gets Better

by alexcarr on Aug 18, 2017
Gay Male

For all who enjoyed my story 'Black is best' I have decided to write some more about my fabulous adventure, as I like to call it, with Sam. He is some special guy and the very best thing that has happened to me. We talk about sharing a home now after a lot of consultation , with his job taking him away for weeks on end, and as considerate as ever, Sam feare...