Most Degrading Sissy Stories Stories

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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 Male Fantasy

by TheKink on Feb 28, 2021
Fetish

This introduction will be short as I feel I have explained what this "book" will contain. However, if you are into aggressive and often times degrading sexual encounters that involve: Futa, sissy, straight, gay or bisexual characters.. then this story will hopefully be to your liking. • Stories will most often be in 2nd person. Please leave suggest...

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CFnm Adventure - 3rd Visit

by lovelicker99 on Aug 31, 2017
Fetish

Note: This is the third story involving encounters between me as a submissive male and a Dominant BBW who responded to an ad I ran online. These stories are fantasies, but some of the specific acts are things I have done and enjoy doing. If you are a woman or a couple that enjoys doing any of these things I would like to hear from you regardless of where you...

Connie Goes to College Ch. 06

by cmorehead on Sep 25, 2017
Transsexuals & Crossdressers

Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. * My freshman year in college became quite a year for me in terms of defining my f...

The Dominatrix Order Pt. 05 Ch. 04

by Jwwsmith on Jun 3, 2019
Fetish

Nadia leaned back and relaxed. Chris placed his nose up to her foot and sniffed at it like a dog in heat. He knew that he was supposed to be repelled by the smell of her feet, but he found their aroma intoxicating; their sweaty, pungent odor aroused him. Her feet had those feminine angles and curves to them that he found so completely desirable and irresisti...

Sissy's Decline into a Slut Pt. 03

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Five: Oh, Oh, Things Look to Begin to Radically Change for Chantel. Well another week has passed by, it's Friday evening and tonight I have to go back to the rest area to hook up with Barry and Ralph as they instructed from last Friday after having me suck their cocks. They promised me that they will fuck me tonight and share me with even more men....

Ultimate Sissy Weekend Ch. 07

by SissyTwinkleToes on Mar 10, 2020
Transgender & Crossdressers

Ruby is sat flicking through a magazine. Mid-twenties, she's been working in the tattoo parlor since college and is soooo bored. So her face lights up when two sissy dumplings mince into the tattoo parlor. She gasps at their ridiculously effeminate outfits that no woman would be caught dead in. She can't believe they've handcuffed themselves together and loc...

A Day in the Lifestyle: Cock Cage

by secondsamuel on Dec 3, 2019
Fetish

Author's Note: My wife and I have been together for nearly ten years. In that time, we have been heavily involved in the local BDSM/Kink/Swinging scene, usually labeled ubiquitously as the lifestyle. I am incredibly fortunate to have such an open-minded and sexually adventurous partner. With her permission, this series shares and amalgamates some of our mo...

The Evolution of Tranny G

by Creamyirish on Sep 13, 2017
Transsexuals & Crossdressers

My beloved Tranny G was so devastated by the one night stand and had lost her confidence. First she was made fun of while shopping, ending the evening with the "perfect" man, having her first true intimate experience with a man, only to find that his promise to call her was false. I did not see her on my last trip, as she was devastated and in her own lovi...

High School Sweethearts Pt. 03

by Lawyerlyzach on Sep 25, 2017
BDSM

The next morning Andi and Jack got up and did their makeup. Andi then produced the clothes that she wanted Jack to wear, and he put on his chest piece, and got dressed. The skirt on Sunday was even shorter than the previous one. Jack was mortified that a good breeze would be enough to let everyone see his ass. The two went to breakfast, and then spent most...