Women Love Humiliating A Sissy Stories

371,945 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Sissy Chantel, New Reality Ch. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eleven: Sunday Fun Well now that our Masters and Mistresses have left us here in the locker room, with all twelve of us sissies now freed from our chastity, our sissy dicks are getting quite hard. We have been allowed a period of sissy sexual freedom. For the next 45 or so minutes we are to engage in a sissy orgy to relieve our pent up sexual desire...

Sissy Chantel, New Reality Ch. 04

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Four: More Sex, Public Humiliation and a Soon to be Turn for My Sissy Life. 8:00am and my alarm clock goes off, I am groggy as I awake but I soon realize I'm about to have another exciting sissy day with Master Camron and Sir Gage. I quickly shower and do myself up as expected in, make up, wig and my black maids dress, black sheer pantyhose and blac...

Sissy/Cock Sucker Dictionary

by silkstockingslover on Jun 12, 2019
Reviews & Essays

Summary: A list of terms to aid in understanding the activities and nature of sissies and cock suckers. Note 1: The author's source material isn't Webster's Dictionary or anything similar, but is drawn from many years of interest in matters sexual and countless conversations, both spoken and online, with other perverts. Note 2: Thanks to Tex Beethoven and...

Behavior Modification Institute Ch. 05

by NancyPan on Sep 12, 2017
Fetish

"I am so proud of you, Tom," Ms Jensen said warmly, approaching me and taking my hands in hers, "It will help you so much to accept this about yourself, Tom. We will help you turn the fantasy of being a sissy into the reality of sissy life. Ms. Panington will be pleased with this progress, and I am quite sure that Kelli will be pleased as well. Let's get you...

How Far Would He Go

by stories55 on Dec 29, 2017
BDSM

This story was inspired by a Domme that wanted me to write a story about being with a man. It was at first just a few paragraphs. She then wanted more and suggested I add various elements. She knew it embarrassed the hell out of me to write it. But then she knew how much I was a victim of my own sensuality and more would follow. She knew she just need to giv...

The Intern Ch. 04

by FrostShard on Mar 6, 2018
BDSM

The day after Mengxia had me listen in to her having sex with her boyfriend, I went back into work with some trepidation. Aroused from my three weeks denied orgasm, humiliated by the events of the previous evening and nervous about my meeting with Mengxia that evening, I could barely focus on work, and it seemed to take ages for 5 pm to roll around. At last...

My Glorious Transformation Pt. 01

by switchhitter420 on Sep 18, 2017
Transsexuals & Crossdressers

My first stab at erotic literature, let me know what you think! Part one of a serialized fantasy journey into sissy faggotry. ***** About ten years ago, I ended a pretty serious, 1-year relationship with a woman I had met while working at a bar. She was this classic beauty: elegant, dirty-blonde hair, thin frame, striking facial features, an amazing ass an...

A Shell of A Man

by uppishcarrot on Sep 13, 2017
Transsexuals & Crossdressers

Six years ago, I was doing well enough to finally afford my dream apartment. It was a studio apartment on the upper side of town. So, I had the job, the apartment, the money... but I was lonely. Very lonely and very horny. Not only would I get all hot and bothered from looking at all of the pretty women at work, but there were also plenty of hot women who li...

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...

Few of My Ultra-Perverted Fantasies

by whiteboibbclicker on Sep 16, 2017
Transsexuals & Crossdressers

Hello, I am a white boi who's addicted to sissy porn and have a lot of wicked and perverted fantasies. In this list, I will enumerate some of them. I would ask the readers to name the one that they like the most in the comments section so I can write a story about it. Authors are more than welcome if they want to write about any of the themes mentioned here...