Gay Sissy Boi Stories

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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...

Versatility on the Court

by puzziboi on Mar 18, 2020
Gay Male

Matt Wenzel was awakened by the sound of his live-in girlfriend rustling through her drawer. "Babe," he yawned. "Just turn on the light." He rolled back over and pulled the covers over his head. He desperately wanted a couple more hours of sleep. The 32 year-old corporate budget analyst had stayed up later than he'd intended last night fucking the petite chi...

The Metamorphous

by eviltwin52 on Aug 29, 2017
Gay Male

I didn't plan to be a homosexual. I didn't want to be known as a sissy. I didn't want to be used and abused by those who were my friends. I tried to be a normal, heterosexual male. Mother nature had other plans for me. My name is John. I've always been on the small side. My height is 5'6" and my weight was 130. I have a narrow waist, a pert, round bottom...

Glazed and Filled at ABS

by Cumpup39 on May 12, 2020
Gay Male

When i finished preparing for the evening, douching out my sissy cunt, shaving and lubing, i went out to the living room where Master was waiting and presented myself. Kneeling on the floor and putting my hands behind my back, i cast my eyes to the floor and waited. After a moment, Master got up and i heard him approach. He looked me over and ran his big, r...

Was I Raped? Ch. 03

by eviltwin52 on Sep 14, 2017
Gay Male

How can one describe the sweet feel of total surrender? There is an eroticism that comes with giving up all pretenses of free will and completely submitting ones self to someone more dominant. I know that feeling. Daddy claimed me as his and after the initial fight for survival I have allowed myself the sublime peace that comes with knowing that another, st...

Owned by a Ghetto Bitch Pt. 09

by FantasizeAndRealize on Aug 28, 2017
Gay Male

Tyrone moved into my apartment the next day. With his move in, drastic changes occurred to my life. These changes turned my financial, social and sexual world upside down. I go to work everyday and pay all of the bills on my apartment. Sholanda spends my paychecks to the last cent. I see all of the new things that she buys Tyrone. I barely have enough money...

Sissy Slave Toy

by slavegurl_veronica on Sep 16, 2017
Gay Male

Where it all began was at gym class in my freshman year of college. Gym was a course requirement for freshmen and I couldn't wait for it be over. I was skinny and weighed only about 130 pounds. I was not at all athletic and one of the smaller guys in the class. Fortunately though there was another guy named Alex, who like me, was also decidedly not jock mate...

A Perfect Confluence

by eviltwin52 on Sep 21, 2020
Gay Male

Sometimes shit just happens. Maybe it happens for a reason, maybe it's just the perfect confluence of events. In my case I honestly believe it was just that, the latter. An unseen force guiding me through life, steering me to and through events which shaped my future and ultimately my life. This is the story of how I went from a normal, pussy chasing asshol...

Bi-Curious to Cock Sucker

by osodd_boi on Aug 30, 2017
Gay Male

I looked forward to meeting Mistress D again, but wondered what it would be like. I had shared so many of my deepest fantasies and desire. Things that I wanted to experience but was also terrified would. Mid-morning I called Mistress D's phone and got her voice mail. I left a message that I would like to see her tonight if possible, and asked her to call me...

Rye's Encounters Pt. 01

by sissyrye on Dec 23, 2019
Gay Male

Note to reader: The following series of encounters are 100% non-fiction, best of my ability accounts of my real life encounters with horny men. Names, locations, and revealing details were altered to protect identities of course. PREFACE: Hi. My name is Rye. I am a cute, 5'9", blonde, big booty, white boy...with a hunger. I have a fairly symmetrical face...