Gay Hairless Sissy Stories

2,946 results
Orientation
Length
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Infinite Scroll

From Alex to Lexi Ch. 02

by oskarwild on Sep 14, 2017
Gay Male

Lexi drifted back into wakefulness, opening his eyes slowly. At first he was disoriented, not remembering where he was or how he had come to be here. Then he became aware of the man lying next to him. He could feel his hairy chest and feel his stomach rise and fall against Lexi's back with each breath he took. He could feel the man's large hand resting on hi...

Nephew's Readjustment Pt. 13

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. * The next weekend, Cynthia called her nephew over in the afternoon. It was time to start preparing him for the next phase in her ever growing plans. She knew th...

A Matter Of Size

by quipogo on Sep 14, 2017
Gay Male

I always had considered myself as a regular straight guy. I love women and I had never been attracted by guys in any way. It all happened at the gym in which I used to do weight training. There it was a coach named John. I knew him for a long time, and we were good mates. At that point I did not need many advices regarding my training, but we used to chat a...

The Boifriend Ch. 02

by AdmiralSquish on Jun 19, 2019
Gay Male

[pre-story]This story's not dead! I was a little stuck trying to figure out what to work on, and I got some comments recently asking for more M/M stuff, and then I got inspired and now here we are. Convenient that the first story to go public in pride month is M/M. Content Warnings: M/M, femboy, sissy, potentially offensive dirty talk Disclaimer: All chara...

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....

Earning Wally an A

by mklit74 on Aug 18, 2017
Gay Male

I realized in college that I was that I was gay, submissive, and that I worshipped my roommate Wally's amazing dick. My relationship with Wally grew over the course of our college career. I would rush home after class to meet him, trying to get home quick enough to change into lingerie, especially a French maid outfit he was particularly fond of, and meet h...

Finally

by yesplease8 on Sep 25, 2017
Gay Male

I have been happily married for over 10 years. My wife and I are sexually adventurous and open-minded. We have always openly shared fantasies. My wife always makes an effort to realize all of our fantasies. My wife, Anne, is a beautiful woman who takes very good care of herself. She is a natural blonde with natural 36 D tits and firm, muscular legs. Out in p...

Zebulon

by MVP6 on Jul 6, 2020
Gay Male

This is my fourth letter describing my expanding awareness from a naive man with a desire to suck a cock to a man willing to explore his seedier side. In my first letter "Costume in a Costume" I describe how I dressed as a girl in a Halloween costume to trick unsuspecting men into letting me give them my first blow job. In my second letter "Gloryhole Illust...

My Husband in My Panties Pt. 02

by eviltwin52 on Dec 9, 2019
Gay Male

Please read Part 1, My wife's perspective first. Johnnie's perspective If you read my wife's version about how much I enjoyed wearing her panties please let me explain myself. Not only did Cin help me realize and accept my fetish but she freed my inner submissive and bisexuality. I'm not here to refute nor challenge Cin's interpretation of anything. It's...

An English Boy Gets Turned Out Ch. 03

by RustyRover on Sep 14, 2017
Gay Male

Mr Tobias was at work earlier than normal today. He had an early meeting with Mick to discuss the new star of their porn website. The Porn industry used to be a license to print money but that had changed over the last few years. Now there was more free porn available than paid for porn. Between Porno YouTubes knock offs, torrents and all these other sites e...