Sissy Prostitution Porn Stories Stories

94,849 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Sissification Fad

by NaughtyEricka on Sep 30, 2019
Transsexual

Sissification hadn’t just become some sexual fad overnight it had actually become a practical way of life for numerous families across the country. The act of sissifying a male family member and using them as a family sex toy and also as an alternate source of income had started in China and Japan but had quickly spread to and across the US. Now 3 years late...

Open in Reader

Sissy Pool Wager Pt. 01

by maxy007 on Sep 14, 2017
Transsexuals & Crossdressers

My name is Max, and I'm your typical high school graduate. White, short brown hair, blue eyes, skinny, and 6'4. I never had muscles or any masculine traits other than my lanky height. I had just finished high school, and had 4 months off before university to myself! As you could imagine, an 18-year-old horny boy like myself really got into my porn, which f...

Recruiting of a Sissy Maid Ch. 05

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Five: Chantel Settling in with Her other Sissy Girls "Congratulations Chantel." as Maid Penny tells her today is her 3rd. month anniversary at The Jade Maid Club as they are sitting at the breakfast table with the other girls. Other girls also congratulate Chantel as well. Chantel replies, "Oh thank you all." As the girls eat their breakfast befo...

Allyson the Sissy Whore Ch. 01

by sissymaidallyson on Sep 12, 2017
Transsexuals & Crossdressers

Kevin was your prototypical mid 20s guy. He had a decent job and lived on his own. He had good friends and whilst he was single he didn't find any problems getting what -- or who -- he wanted in the bedroom. However he had long been fascinated by glory holes and by being serviced in them but by being the one servicing. He was convinced he was straight and l...

Recruiting of a Sissy Maid Ch. 04

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Four: Chantel, Fitting Into Her New Lifestyle. Master Holt says, as the two of them walk out from the elevator on the 2nd floor, "This will be the floor that you will begin your life in servitude to us Chantel. Lets go find your head maid Penny and then get you to your room." Chantel grows more and more resigned to this new life as she see's a very...

Trixie's Chastity 03

by trixie47cd on Sep 19, 2017
Transsexuals & Crossdressers

By the time I pulled my car into our driveway, most of the semen coating me from head to toe had dried to a flaking crusty shell. I stuck to the driver's seat as I climbed out on wobbly legs. The sun was just coming up and I hurried to get inside the house before any neighbors saw me like this. I started a pot of coffee, put the gallon jug of sperm in the f...

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...

Making a Sissy Jock Pt. 01

by Sissyhalo1 on Jun 1, 2020
Transgender & Crossdressers

My life changed about a year after I was done college. I'm Mason, or I was and I used to be a football jock all through high school and played all through college and after all that I kind of just never got picked up. So...what do you do with a physical education degree? Most guys taught gym or coached some places. Me? I got a massage job at a spa. There...

He Changed Me

by Sissyhalo1 on Dec 23, 2019
Transgender & Crossdressers

I know a lot of these stories are about some guy that watched porn or read it and got hooked or were some short femmy guy that got tricked into getting boned but that's not me. I'm Sam and yeah it's Samantha most of the time now. But before that it was just Sam and I was in my last year in college and to save money to fix my car I moved into a rental house...

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...