Gay Shemale Chastity Stories

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Surprise at the Door

by Luckystiff2112 on Aug 18, 2017
Gay Male

This just happened to me today! But it all started last night. My buddy came over and we sat around shooting the breeze; took a ride in his hotrod- a '69 RoadRunner! Way cool! We came back and proceeded to get pretty drunk. So I fed him, gave him some water to sober him up some, and then he left. I was home alone now. My wife is away for the weekend, and wh...

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...

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...

From Gay Husband to Slave Pt. 01

by assguzzler on Apr 3, 2019
Gay Male

My husband Winston and I were married when I was twenty two and he was thirty. I told him of my submissive fantasies and he role-played with me some at the beginning of our marriage but for the most part he showed little interest in D&S or Domination. We had a good marriage but we often fought as we both tried to dominate the other when it came to who would...

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...

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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...

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...

A Soldier's Journey Ch. 01

by FenFenScreeScree on Apr 13, 2020
Gay Male

(This story is based on true events. Details have been changed to protect the identity of the characters) Sometimes, I worry if I've gotten too far in over my head... My journey through chastity play is not an easy one, and it's a path that many of my sexual peers would never have had the fortitude to walk down. Allow me to preface this story with what y...

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...