Gay Tranny Stories

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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...

First Time at the Gloryhole

by hornytedd on Aug 18, 2017
Gay Male

This is my first attempt at writing so please be gentle. Other than changing names, this story is true and was the start of a roller-coaster of sexual exploration. ***** I considered myself the very definition of normal, if not boring. Working mid-level management in a financial firm, living in the suburbs of New York with my 2 young kids, attractive wife...

Swing Shifting

by dCharlesStuart on Jan 16, 2019
Gay Male

I'm 69 now. 6ft tall 180 lbs and about 5 inches cut. Thinning grey hair and although I was a pretty good athlete when younger it's all pretty much over now. AS I wrote in many of my stories I started fooling around with men from the time i was 14. That was the legal age in Ontario at the time although that wasn't much in mind at the time. It just so happene...

Woken by a Blow Job

by Travel_by_day on Sep 1, 2017
Gay Male

It had been 8 years since they had all left university. Back then they were a band of brothers, inseparable. 6 guys all living under one roof. The house was an absolute disaster, as you might expect when 6 college aged men live together. The front door was smashed in, and to "fix" it, Dylan had just drilled a couple screws in place to hold the door permanent...

Fateful Encounter

by Markerss on May 12, 2019
Gay

We have all had encounters that we remember and those we want to forget, but this particular one has stuck in my mind, even though I have for so long tried to put it out of my mind. However, I do periodically find myself remembering this eventful time in my life and when I slip back to when it all happened, I find myself wishing it would somehow materialize...

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My First Time Taking a Man

by AlexanderMaximus2016 on Aug 18, 2017
Gay Male

**This is my first story and it happened to me real life. Sorry if there are too many mistakes** I can't remember when this curiosity started. Was it when I saw tranny porn by accident? Probably. The thing is over the years since I was 17 I occasionally watched tranny porn until it became a regular thing. By the time I was 19 I had a serious craving for dic...

Married, Sexless, Curious

by Donotwasteyourlife on Jul 17, 2018
Gay Male

I am your average profession business guy and travel most weeks to different parts of the country. I live in a sexless marriage and the majority of my sex life depends on porn and occasionally a few toys. My Fleshlight is my favorite and it goes with me on most of my trips. I felt lonely most of the time over the last 10 years but never had an interest in c...

Dave Feeds Me My First Cock

by Funnbunnies on Sep 14, 2017
Gay Male

When the internet finally reached us here in Africa, it was slow and exorbitantly expensive. Nowadays it is only a fraction less expensive, but still frustratingly slow. Because of this, the only time I could check out hot and exciting porn on the net was when I finally was alone at work after everyone else had gone home. Like so many other inexperienced sur...

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...

Tom and Aaron Welcome Ben

by THoward95th on Dec 25, 2019
Gay Male

This is part of an ongoing story over multiple Categories with common characters. ************ I was sitting at Cup in Time drinking my doppio and was thinking how so much had changed in a little over a year. Cyndee and I weren't together anymore although we were definitely "friends with benefits". We didn't get together much anymore, especially since Dav...