Gay Shemale Mistress Stories

370 results
Orientation
Length
Source
Infinite Scroll

Sex with an Old Man

by johnthome7690 on Sep 14, 2017
Gay Male

Before I start I should give you some background on myself. I also want it to be known that this story is 100% non fiction. If you like the story, contact me via contact tab. I am a mostly straight man. I never have, and still after, the incident I am about to tell you about, am not attracted to men. I never walk past a guy on the streets and want him sexual...

Becoming a bitch

by Testytesterton on Nov 28, 2019
Gay

(Skip this if you don't like boring behind the scenes stuff. Wow! Over 3000 likes and story of the week for my first story here! Thanks to everyone who has liked, bookmarked or commented. The feedback lets me know what works and what might need work. I would love for this to be the most popular story in its category, so if you like the story, "like&quot...

Open in Reader

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...

My Old Pal Charley

by MrSperm on Aug 18, 2017
Gay Male

Longtime reader, this is my 1st literary submission. It is mostly a true story. ***** In my 30s I reconnected w/ an old high school chum on a whole other level. We had been friends on and off over the years, but I never let most people (esp the crowd i went to school with) know that I was bi. Well, an in the closet bisexual cocksucker to be exact. So this...

Wanting a change

by ShaPop on Dec 1, 2016
Gay

John was a good looking guy, but always felt rather generic and lost in the crowd in his home town. He was of average height at 5'10, and at 25 had a trim hairy body with sandy brown hair and blue eyes, he was very much an all american guy. The one place he wasn't average was his cock, which was about 7.5 inches long, quite thick and circumcised. When it cam...

Open in Reader

Adult Video Store

by bisuffolkguy on Apr 17, 2019
Gay Male

So I've come along way since my ass stretcher butt plug and dildo play. I use an extra-large butt plug daily, and have begun aggressively stretching my ass every chance I get. Dildos have progressed to large vegetables such as butternut squash and water bottles like Core and Smart Water. Its amazing with enough lube, you can get just about anything up your a...

Fixing the straights

by cdbaby on Dec 28, 2016
Gay

You wake up and prepare for your day, unaware that this would be the last day you would be considered straight. You shower as you did every morning and felt the water's warm touch as it cascaded over your skin. You could stay here forever if you could. But you need to start your day and the hot water would run out before long. You wash your hair, then the re...

Open in Reader

Glory Skills

by glory_first on Aug 18, 2017
Gay Male

Finally finding enough time last Thursday morning and mid-day to run a number of errands, it was possible to finally revisit a newly (re)discovered gloryhole. Going into the porn shop around noon, it was about as empty as during the last visit, on a Saturday mid-afternoon. After paying and entering the long and dimly lit hall, a couple of men could be seen...

Lost Phone Ch. 01

by flictus on Feb 12, 2019
Gay Male

It all started a couple years ago when I lost my phone. I had when I went to church and then I left in the bathroom, when I got back to into church I realized my phone was not with me and that I had left it in the stall. I went back to the bathroom stall and it was not there. I vividly remember putting on top of the toilet paper dispenser. My mind raced I ha...

I Thought I Wanted It Rough...

by LonelyVirgin on Sep 14, 2017
Gay Male

Let me start off by saying I'm straight. I'm very attracted to women, but feel absolutely no attraction to men. When I was younger, I always had a fascination with anal sex. I don't know why, but from when I first started looking at porn on the internet, I was always looking for anal sex. The odd thing was, I wasn't so focused in on the penetration of all...