Gay Sissy Cum Stories

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The Talent Scout

by eviltwin52 on Jun 5, 2019
Gay Male

The day I first met him was like any other day. Riding the Metro to work I was suddenly jostled out of my reverie by some one bumping into me from the back. Turning I found myself looking up at a ruggedly handsome man. His steely grey/blues seemed to pierce into my very being. I wanted to look away but was unable to do so. After a few seconds that seemed to...

Jail Time Ch. 02

by oralguy82 on Aug 18, 2017
Gay Male

Before, I had spent 2 weeks in the county jail and, I thought that was all done and gone, and would be forgotten. But about 4 months later, I was almost thinking how can I sign up for another 2 weeks. I felt humiliated about the experience, but so turned on too. More than once I had jerked off to the memory of that humiliation. A 25-year-old man thinking ab...

Spanked and Buttfucked Asian Male

by asianspankee on Aug 30, 2017
Gay Male

I'm an Asian male, with slim and very smooth naturally hairless body, and average height. The story happened when I was in my twenties. I hope you enjoy reading it... Ever since a teenager I've always had a very strong, repressed desire to get fucked by another man. I think one reason is because my body is quite slender, and extremely smooth devoid of any b...

My New Daddy Ch. 01

by sissytoy20 on Feb 13, 2018
Gay Male

I'm 21 years old and I attend college but I still live at home for financial reasons. I've always been fem and young-looking for my age. I like to cross dress, but I don't usually dress fem in public. I've just found that it can be difficult for some straight folks to take a young male who likes to be a sissy slut. So you can imagine my surprise when I was r...

Humiliated at a Motel

by missy_willow on Jul 3, 2019
Gay Male

Humiliation has long been an important part of my sexuality. Being called names, getting slapped and choked, and being exposed in public get me harder than anything. I decided to pay a man who advertised as a Master who cared only about denigrating those who employed him. We agreed on a price and I arranged for a hotel room near the highway which was freque...

Beauty and the Beast Pt. 01

by Suzzique on Dec 17, 2017
Gay Male

I hesitated a long time before I advertised on Craig's list. I was 18 and had left school two months before. I had a place at university for the following October, almost a year ahead. I was living at home and had a mindless temporary job in a solicitor's office that made no demands on anything but my time. I'm a very shy person and no one knew I was gay exc...

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...

Gay Cave Escape

by Hypnodip on Mar 11, 2021
Gay

Drip! Drop! Drip! A staccato of water droplets add to a quiet and dark ambience. A nearby rock is dislodged, crashing with a large boom. You awake with a jump, chilled from the rock floor you were sprawled on. The room you're in is almost too dark to be traversed. You can see three ragged walls surrounding you, sprawling upward out of your limited night visi...

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You are a Sissy Pt. 03: Body

by Roland15Rollin on Dec 24, 2019
Gay Male

Hello. Hello, sissy. You have come back. You have come back again for another session. Welcome back, faggot. My sexy sissy faggot bitch. I am so glad you have come back. But you have no choice, do you, sissy? You have to come back. You need to come back. You need to hear my voice. It is the voice of truth. The voice that tells you what you are. What you tr...

My First Time with Ryan

by elliotsconfessed on Dec 19, 2018
Gay Male

It was 2013 on a hot summers night. Me and Ryan decided to go camping and make the most of the beautiful weather! We were both 18 and fresh out of school both deciding what we were going to do with ourselves now we're "grown up". Ryan and I would often talk about what girls we would love to hook up with or see naked! These chats got us through our high scho...