Gay Shemale Surprise Stories

7,774 results
Orientation
Length
Source
Infinite Scroll

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...

Never Mentioned Again

by sr71plt on Sep 14, 2017
Gay Male

"Shit, the way this snow is falling, I'm not getting my rocks off tonight." "Steady as she goes, Chuck. Lucky for us there are bars close to the ship. Let's try this one." Naval Petty Officer Three Ryan Stevens pushed open the door of the bar and ushered Naval Petty Officer Two Chuck Adams into a dimly lit bar, filled with smoke and with muted and fuzzy Co...

Black Cock: 1 Day Changes Everything

by silkstockingslover on Sep 25, 2017
Gay Male

Summary: Straight married man can't resist black teen's huge cock. Note 1: This story is dedicated to goamz86 and to making one of his fantasies as real as possible. Note 2: Thanks to goamz86, Robert, and Wayne for editing this story. Note 3: Although this story is mostly a GAY interracial story, it is really a much deeper story about one man's lengthy jo...

A Night at the Movie turned me Gay

by jamtby on Oct 6, 2020
Gay Male

During my senior year in college I was a busy, serious student. I had a girl friend and we enjoyed time together and an active sex life. All in all I was a typical 20 year old male. Then an unexpected movie changed everything. My girl was out of town on a field trip for a psychology course she was taking. It was Friday night and I was horny. I made the dec...

Bob Handles Mark's Huge Tool Ch. 01

by scrotus on Aug 18, 2017
Gay Male

I had long fantasized about being involved in a sex situation with more than one guy. I had done several three ways with a woman (two guys and one girl) but they never involved the other guy and I performing on each other. In recent years, I've developed an insane desire to move beyond my several male-male encounters and add a third guy in. This is because o...

Straight to Bi, Cam to Real Life

by dlcalguy on Aug 18, 2017
Gay Male

After I finished university, I struggled for a good-paying job and money was tight. But I couldn't face living back at home. I managed to find a room to myself in a house-share with two other guys and three women. We were mostly in our early twenties and doing various entry-level jobs. One guy, Pete, was older. About 45. He was on a temporary assignment in o...

Losing My Cherry

by bimanms on Sep 14, 2017
Gay Male

It was 1996 and I was living on the coast of Mississippi. I had been married for six years, and my second son had just been born. I had just returned from several months at sea on a Navy ship. My wife was always exhausted and not interested in sex. I, on the other hand, had a perpetual hard on. One day while driving along the beach I happen to notice a sign...

My First Big Black Cock

by babaca789 on Sep 14, 2017
Gay Male

This is my first submission, please let me know what you think! All comments are welcome :) ***** Well, I was about 18 years old and fresh out of high school. Horny as hell, constantly jerking my cock at porn, thinking about girls (I was actually pretty straight at this point) and trying to fuck as many girls as possible. I had hooked up with a few guys t...

What a Difference a Gay Made

by Chris7sw on Aug 18, 2017
Gay Male

I woke up and rolled over to blearily glance at the alarm clock. It told me it was 9:41 – so today must be Saturday or Sunday – otherwise I'd be up and out at work by now. Well, I hoped that was the case! I rolled back and came face to face with an elfin female face, sleeping contentedly on the pillow, a happy smile playing on her countenance. And it starte...

Becoming a Cocksucker: A Journey

by silkstockingslover on Sep 25, 2017
Gay Male

Becoming a Cocksucker: A Journey Summary: Man's journey from straight & married to loving cock sucking Note 1: Although unorthodox, this is a 2017 Valentine's Day Contest. No it's not a love story between a man and a woman, a woman and a woman or even a man and a man... it's a love story of a man and the discovery of his love for cock. No hearts and fl...