Sissy Humiliated Stories

21,486 results
Orientation
Length
Source
Infinite Scroll

Made Over Ch. 03

by gbr2004 on Sep 15, 2017
Fetish

This story involves forced cross dressing, gay sex and bdsm scenes. Don't read if not into these scenes. * I had met a man in my apartment building and he had invited me to join him at a club he goes to in LA. I was a naive boy from Kansas attending USC and I had no idea what I was getting into. The club ended up being a gay leather bar and before the nigh...

Moving To Louisiana Ch. 3

by eeric on Sep 14, 2017
Interracial Love

If you have the time you can e-mail me at the email address in my profile and tell me what you thought. * * * * * Over the past weeks Helen has become more open about her love for black men. She has been out to clubs and danced with both Ty and James, although never with both of them together. Then she has had me lick and suck her pussy when she gets home...

Black On Black Cuckolding : Hell

by Samuelx on Apr 3, 2019
Group Sex

Officially, we don't exist. That's what conventional wisdom tells us. If you were to type the words "Black Cuckolds" on Google, all you'd get are references to the standard-issue Cuckolding, which typically involves a big Black guy fucking a White woman while her husband or boyfriend, also White, watches. Nothing wrong with that if that's what moves you. My...

A Tale of Slavery

by gunnarsub on Sep 17, 2017
BDSM

Once upon a time there was a straight guy who was known by everybody as a well respected fellow. But he had a secret life. Nobody knew that he dreamt to become a feminized slaveslut, seeking an infinite and irrevocable blackmail relationship with a pitiless Mistress who would be prepared to break him with no way out. He wanted the Mistress to torment him n...

Pat's Panty Slave Ch. 03

by Sissyfreak on Sep 16, 2017
Transsexuals & Crossdressers

Having been humiliated for a second time, I thought things couldn't get any worse, how wrong could I be! I was sat at home one day, kids at school, Wife out shopping, when there was a knock at the front door. Jo was standing there with a carrier bag. She threw the bag to me and ordered me to put on the items within, then come to her house next door. I looked...

Office Cumslut Ch. 01

by DrLuverotica on Sep 12, 2017
Loving Wives

FRIDAY MORNING "Are you going to work dressed like that Jo?" My wife was dressed in black, sexy high heels, black stockings with a pink 1920s style pencil line up the back of them, pink frilly satin panties (she hates thongs) and matching push up bra. "Yes I am hubby," she purred, as she pulled a navy blue, short pleated skirt over her hips. "Is there s...

Cream Puff Ch. 03

by RubixStu on Mar 25, 2019
BDSM

I was naked except for my wig, my makeup, my stockings and my heels. I sat on Roger's lap, his erect cock deep inside my ass. He was watching a nature program. My legs were spread and his arm was wrapped around me while his hand lazily toyed with my little boy parts. He wasn't fucking me, he was simply impaling me, filling me with his masculinity while I rev...

Satan's Sissy

by nancyvasquez on Oct 15, 2017
Transsexuals & Crossdressers

Oh you stupid little faggot! You just had to go and get married to a woman! Why?? Why fuck up some poor girl's life like that? Was it because you crave humiliation, and subconsciously you knew it would be just a matter of time before you got caught, and you would be outed publicly? Outed as a pole smoking homosexual who was more at home in frilly skirts and...

The Awakening of a Sissy Pt. 05

by sissyjolie4u on Feb 3, 2020
Transgender & Crossdressers

There I was, on my knees, in very skimpy feminine undergarments, locked in a room in the back of an ABS, with 6 men and my Mistress. This was the start of what was to be the other portion of my punishment. Mistress walked toward me with that evil grin of hers. As she was approaching me, she said, "Jolie, these men are here to assist me with your punishment...

Hubby Drop To Thy Knees! Ch. 02

by Ashesh9 on Sep 17, 2017
BDSM

CH. 2 :HUSBAND , BEND OVER & PART THY NETHER CHEEKS !!! Her ringing , humiliating command was heard all over the field “Husband, bend over the Punishment Table, bare thy delectable, horny bum & part thy nether cheeks for Thy Royal Monarch’s Pleasure !!! Immediately!!! Do it now, boy !!!!” The sweet girlish voice, the Commanding tone, the embarrassing Orde...