Sissified Stories

213 results
Orientation
Length
Source
Infinite Scroll

Sissy Life Pt. 02

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

I scurried to the bathroom, tears streaking my face. I was dripping cum on the bedroom floor as I went, but I didn't stop. I just wanted to get out of the room. I couldn't believe how badly things had gone! 20 minutes ago I was stood in my May babydoll, black stockings & red heels set for some intimate time with my wife, my Mistress, but now? Now things were...

The White Slave

by mspbottom4black on Oct 6, 2020
Interracial Love

Editor's Note: this submission contains raceplay and femdom content. * Not long ago it was a straight and stuffy white male. it was arrogant and self-satisfied with its white male social and economic leverage and advantages. In the rat-race of white society it suppressed its submissive white side. But from time to time it would slip into daydreams of hav...

The Office Ch. 06

by EasilyConfused on Apr 28, 2020
Transgender & Crossdressers

The constant hum of the paper copier, as it scanned and then reproduced its copy, echoed loudly in the enclosed space. Tammy rocked his right ankle on his four inch patent white heels as he waited for the copier to complete its task. His left arm rested across his midriff, whilst his right hand twirled at the ends of his blonde hair as he waited. Tammy hated...

The Office Ch. 05

by EasilyConfused on Sep 24, 2019
Transgender & Crossdressers

Tom had lost count of the number of times Hamilton had struck his ass with the wooden paddle. His cock ached for release but his unwitting periods of mental manipulation had embedded a control in his psyche. He knew that whenever he was in the presence of his Mistress he should seek her approval before acting. And that very much included ejaculating from his...

Have we met before?

by HYjaCK on Jun 1, 2020
Bisexual

Light shone through the curtains, blinding you momentarily as you sat up, taking in the environment around you as there's a knock at the door. Struggling to think, you stand up automatically, putting on a discarded red robe and staggering to the door. Leaning against it, the door knocks once more. "H-hello? Room service!" A female voice from the ot...

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Fat Indian Crossdresser Slut Gangbang

by bottomgay on Sep 16, 2017
Transsexuals & Crossdressers

I am your typical sissy bottom guy who loves mature men. My proportions being large, club me into the BBW category so only the daring types can enslave me. Mature men in the age group 35-60 attract me. Only young guys with very huge dicks are an exception. This is about a naughty adventure of mine which happened in a residential area in New Delhi. The hormo...

My Initiation

by lockedupslut on Sep 13, 2017
Transsexuals & Crossdressers

(This story is a work of fiction. If you don't like erotic stories that contain cross dressing, heavy gay themes and water sports please just don't read it. Thank you.) * I was determined. This weekend it would happen. I would loose my gay virginity and complete manhood. The hard way. Tonight would change everything. Until now I've never had sex with a ma...

Sissy Dreams Ch. 02

by SissyJane on Sep 13, 2017
Transsexuals & Crossdressers

I'm floating though I don't remember being asleep. Everything is a soft pink light but I can't see anything. I try to move and find that I cannot, bound by ankle and wrist off into the nothingness. This doesn't scare me but rather excites me a little. I feel her touch first, the long fingernails trailing up my legs which I realize are perfectly smooth and s...

My First Feminization Pt. 02

by npbear on May 2, 2018
BDSM

An eternity passes. Or perhaps it's just 5 minutes. The gentle sounds from the crowd rise as the evening progresses, people begin getting into the party, but I remain, hard, excited, nervous and alone. The room is warm, pleasantly so, fortunately, but still I shiver as I feel fingers on my back, walking their way up leisurely. The gag is removed and a low wh...

Be My Bitch

by purekink on Aug 20, 2019
Transgender & Crossdressers

I'm so glad you agreed to be my slut – I've been searching for a crossdressing hussy I can train to be my personal tart for some time now, and I'm certain I can teach you to fit the bill. I understand your fantasy is to be dressed as a sexy sissy and have your manhood and your cherry fucked right out of you. This pleases me, as I enjoy nothing better than u...