Gay Sissy Boy Stories

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Orientation
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Infinite Scroll

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...

Truck Stop Turn Out

by Ewriter111 on Dec 3, 2019
Gay Male

Editor's note: this story contains scenes of non-consensual or reluctant sex. *** I was driving home from college for spring break and to celebrate my 19th birthday at home. It was a four hour drive and I got a very late start after having helped my girlfriend and her friends pack their car for Panama City. At midnight, I was still 150 miles away and total...

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...

Fat Bottomed Girl Pt. 05

by eviltwin52 on Jun 4, 2019
Gay Male

It's gotten to the point that I'm chained to my obsession to a fat bottomed girl. I've allowed myself to be molded into that mate Sheila wanted. I mean before Sheila I was a woman chaser. A woman with a big ass fascinated me, aroused me, and now I'm a slave to my fetish. Sheila dominates every aspect of my life. Me queering off for her is just another way fo...

Discovering My Slut-Side Pt. 02

by i_like_it_like_that on Dec 10, 2018
Gay Male

With Danielle's fingers and mouth off my ass, I knew what was coming. Not being able to cum made me incredibly horny. I was ready for release and wanted Andrew's cock inside of my warm hole. I stared at his dick with a look of lust and got lost of the moment. I was brought back to reality by Andrew slapping my face with his veiny shaft. "You ready for this...

Princess

by skinnysailor on Mar 2, 2020
Gay Male

I'm Dan. My lover, Rex, calls me 'Princess' as in his little fairy princess. He told me how tonight's date wanted me to dress. Very specific. Three inch strap on spike heels. An ankle length skirt. I chose my dusty blue wool one. A see through blouse. I'm wearing my pink one with the frill collar and cuffs. Panties, no bra. I put a little rouge on my nips....

Caught with My Pants Down

by Cumfusion on Aug 18, 2017
Gay Male

The early morning sun shone into my student apartment that beautiful May morning. First Year exams were finished, there was no more revising to do, it was relaxation at last. 'Nothing to do. This is going to be my freedom.' I thought. I would often wake up with a hard on but that morning I felt like doing something really sexy. Just lying in bed and masturb...

My Wife Hands Me Over to My Dom Ch. 03

by FantasizeAndRealize on Mar 6, 2018
Gay Male

It has been almost three months since my wife Susan found out about my gay affair. Since she found out she has been handing me over to my Dom, in person, every week for our sessions. She has gotten to know Carl, my Dom quite well. They love talking about me as if I am not even there. Susan really enjoys taking me to Carl and picking me up after our session...

Owned:Fantasy Becomes Reality

by silkstockingslover on Sep 14, 2017
Gay Male

Note 1: This story was written and is dedicated to a true wannabe faggot-cuckold Dave. Note 2: A special thanks goes to Estragon for his copy editing work. 1. THE BEGINNING I blame Literotica. No seriously...if it wasn't for Literotica, none of this would have happened. Now in all fairness, some would argue it is my fault; as it was my own stupidity a...

Feminized by My Father

by YANKEE DAN on Aug 30, 2017
Gay Male

I opened my eyes, blinked, yawned, closed them again. I felt confused, disoriented in a way that was... strange. It wasn't like waking up was supposed to be, I wasn't half asleep. I can't remember getting in the bed, in fact I can't remember the last thing I remember. Where did consciousness end last? I was clueless. I tired to move my body and I found it...