Gay Shemale Surprise Stories

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The Long Trip

by TheBlackStallion on Mar 6, 2018
Gay Male

Editor's note: this story contains scenes of non-consentual or reluctant sex. This is my first story, please give me some feedback. Parts of this story of true, some of it isn't. I'll leave you to decide * I've been a young sailor for almost two years now. We've been at sea for almost 75 days. Tomorrow we will be pulling into Thailand. It's been a long ri...

My First Cock in Years

by Bostonsnowball on Aug 18, 2017
Gay Male

As I was driving home after a weekend away, I started thinking about going to the Paris Theater. I was feeling very aroused since I hadn't jacked off in several days, I needed to feel a pair of lips on my cock. I had been there before and always had some guy slobbering on my cock within 15 minutes of walking through the door. I parked as close as I could, t...

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 School of Freedom and Love

by Jam18 on Aug 18, 2017
Gay Male

Oh, man, it can't be morning already. I rolled around on the bed and checked the time. "SHIT," I said out loud. It was 5:30 a.m. and I only had one hour left to say goodbye to my room, to my house, to my life. Ok, maybe I was being too dramatic, but being sent off to boarding school wasn't my idea of a great eighteenth birthday present. Yep, that's how I was...

Drunk at College

by johndovinski on Sep 19, 2017
Gay Male

*** Author's Warning: I've never written anything that's published anywhere before. I've read A LOT of Literotica stories and it took a lot of nerve to just write something on here. This story is a bit of an extended fantasy about what I wanted to happen at a very specific time in my life, but names and details have been changed to protect the innocent. Than...

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...

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...

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...

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...