Gay Sissy Whore Stories

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Infinite Scroll

You are a Sissy Pt. 07: Cuckold

by Roland15Rollin on Dec 24, 2019
Gay Male

Hello, princess. Hello again. I see you are back. That pleases me, sissy. It pleases me that you have come back for more of what only I can give you. The truth only I can give you. And we have come so far together, princess. We have come so far exploring the depths of your sissy feminine mind. And your mind is feminine. Make no mistake about it, princess....

Little Sex Toy Ch. 01

by keptsissy on Sep 26, 2017
Gay Male

Rough sex with a big strong man is something I'd always fantasized about. Ever since I can remember masturbating I'd think about being made to do things, dirty things for a man. I thought about being spanked, made to perform for a man, one that wasn't mean but very dominant, somewhat cruel and unusual but not terrifying. I had the fantasy in my head often....

Research

by eviltwin52 on Aug 18, 2017
Gay Male

This story is dedicated to Kept Sissy who was so instrumental in helping me understand my urges. I was in the final phase of getting my Doctorate in psychology. My dissertation was to be on the difference between transgender boys, homosexuals, and sissies. You see, the transgender feels as though they were born with the wrong physical sex organs whereas i...

My Time in the Monastery

by brownmonkk on Aug 18, 2017
Gay Male

Brother / Sister/Slave, ("TML") November 1970 "Good loving & Good Scourging" The story of a MASTER and his slave! WOW, "it" finally happened!!! I had had my first sex, and it was with a fellow brother monk in the monastery. It was great. I always imagined having my "first time" with a sexy gal, but nonetheless my first sex was great! I often fantasize and...

Daddy's Girl

by oskarwild on Sep 25, 2017
Gay Male

The Hitchhiker It had been snowing all day. A wet, heavy incessant snow that was covering everything including the highway. Combined with a wind-chill factor in the teens, Christopher was almost frozen stiff. He was elated when the huge semi pulled over to pick him up. He climbed up into the cab and smiled thankfully at the driver. "Thanks a lot mister. I...

Bitch Dick Twitch

by cockmachine on Aug 18, 2017
Gay Male

First duty of the day. I slide my shaved-smooth body nimbly from the sheets and tip toe into the bathroom. I quickly take care of any errant stubble and look myself up and down in the mirror. I am 19, skinny, about 5'10" with short brown hair and blue eyes. Aside from the slightly-too small lace thong I am wearing, I am nude. That is, if you don't include a...

Coming to Terms

by HerLittlePiggy on Aug 18, 2017
Gay Male

I stood naked beside the bed. My hard cock jutted straight out from my body betraying my excitement. "I have never done this before," I said softly. "But it excites you doesn't it?" "I guess so," I answered as my cheeks flushed red with embarrassment. "You guess so? It's a yes or no question. Does it excite you?" "Yes," I replied honestly as I cast m...

A Night at the Club

by keptsissy on Sep 16, 2017
Gay Male

"Did you make a mess in your panties? Let me see." I stand in front of him. He's seated at a table in the back of the bar. He smiles, a dirty ogle more accurately, toward the man seated to his right. He looks back at me, sees my nervous reaction. He shakes his head with a somewhat disgusted look on his face. He reaches out and takes the front of my short sh...

Exploring a New Store

by TerriC on Nov 18, 2019
Gay Male

"I don't know how he did it, every day in those white tights." I thought to myself, as I pulled a pair of tights up my legs. The semi opaque white spandex stretched around my hardening cock. How the actor who played Robin, in the '66 Batman tv show, wore those tights without walking around hard all day, I'd never know. A wet spot forming on my tights as I sl...

Job Evaluation -The Christmas Party

by VeryCuriousIan on Mar 18, 2020
Gay Male

It was now over a month since Ian's last disciplinary problem and he had at long last got his act together. He was now one of the best employees in the office. Even Carol, his hated line manager, had to admit he had turned over a new leaf. Although she still loved to call him a little cocksucker anytime she could to cause him maximum embarrassment. Ian's...