Sissy Humiliated Stories

21,486 results
Orientation
Length
Source
Infinite Scroll

A Letter to Our Pantyhose-Sissy

by Sheermistress on Sep 19, 2017
Transsexuals & Crossdressers

I'm on my bed on my knees, my skirt pulled tight and just a little high, exposing my control-top pantyhose to your eager eye. My feet are dangling over the edge of the bed and you, my little pantyhose-slut, are standing behind me, dressed in your sexy schoolie outfit and mary-janes. Your face is made up in a prissy, sissy, teen-girl way and your hair is fini...

A New Life Ch. 03

by sissycinnamonswirl on Sep 18, 2017
Transsexuals & Crossdressers

"Click on this link, sissy. I want to show you something," Mistress Sally said. And I happily followed instructions believing it to be some aspect of sissy porn like a caption, or little GIF video. I couldn't have been more right...or more wrong. My newly painted red lips parted in shock as my computer opened a new browser that showed what seemed to be an a...

Sissy Cuckolded by Girlfriend Ch. 01

by SaraRurik on Sep 16, 2017
Transsexuals & Crossdressers

My name is Josh and I'm a 19 year old white guy with a beautiful girlfriend. Her name is Angel and she is the best thing that has ever happened to me. I love her with a passion and intensity that is hard to describe, she is everything a man could ever ask for and more. She is caring, sexy, understanding, kind, intelligent, and totally a bad bitch. We have...

The Farm Ch. 03

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

Ed took his time with me. He constantly taunted the two younger men as they waited eagerly for their turn to stuff their hard cocks into my cum filled sissy cunt. "Only right that your daddy gave his bitch to a real man before you two pathetic losers." After smothering me with his fat sweaty gut and smelly cock Ed had swapped ends never letting go of his pri...

Ian's New Job

by SatinSlip on Nov 26, 2018
Fetish

Authors note- this story includes non-consensual, rough, and coerced sex. As well as straight and bi-sexual sex. ************ Wendy moaned as her husband slowly licked around her pussy. She grabbed the sheets in her ecstasy. An orgasm rising excruciatingly slowly in her. Ian was great at cunnilingus. He practiced often on his wife. Delighting in the way...

Graduate Studies to Gay Pt. 02

by jamtby on Apr 9, 2019
Transgender & Crossdressers

After the night at James' apartment the previous quarter, I had tried to put all that out of my mind and concentrate on school and be normal. I did see James once on campus and he asked how I was doing. He hoped I had gotten a good grade on that paper I was writing when I met him at Jimmie's that fateful Friday night. He also said that if I wanted to earn so...

Sissy Life Pt. 04a

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

That's it then. I am going to be whipped by my wife's - my Mistress' - lover. I had offered him use of my mouth in a vain attempt to stave of the beating to come, but as he said, why would he be interested in my mouth? He has my wife's whenever he wants. He has no interest in sissies, this isn't his fantasy - he's a man. A real man. 'I said get over here a...

Fetish & Fantasy Pt. 01

by GavinIsaNuisance on Jul 13, 2020
Transgender & Crossdressers

This work is completely fictitious, any similarities to any persons living or dead is purely coincidental and entirely unintentional. All persons depicted in naked/sexual acts are 18 and up. Down and out aspiring model Taran Kilkenny becomes the hottest commodity in an escort service for trannies! But first he's gotta get trained by his new and domineering b...

Stevie's Journey

by gbr2004 on Oct 7, 2019
Fetish

I remember being so excited landing a position as a legal assistant at such a good law firm. My boss Mike Maddox seemed to be a great guy and I was looking forward to learning from him. I never imagined what it would be that I would learn from him. This job has changed so much and I can't even decide if I regret what has happened or if it was where my life w...

Sissy's First Day

by whispy_sub on Sep 13, 2017
Transsexuals & Crossdressers

Sissy let out a disheartened groan as he closed the classroom door. He looked down despondently at the discipline demerit clutched in his gloved hand, "It's my first day and already I screw something up; I can't believe this." It was only his fourth hour here at the Academy, and already he recieved a demerit. He wasn't quite regretting his decision to enrol...