Milf Sissy Stories

11,607 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Tales of Seth and Travis Pt. 01

by pantywriter on Sep 16, 2017
Transsexuals & Crossdressers

The early June morning dawned misty but cloudless; it was forecasted to be one of those absolutely perfect late spring days with dry air, sunny skies and temperatures in the seventies. Nothing could be better. Whether it was the weather, or just his state of mind, but Seth woke in a wonderful mood. He sang quietly to himself as he made his bed, tidied up h...

Our Conquerors, Our Concubines

by Shendude on Dec 20, 2010
Science Fiction

Millenia ago, an alien race created the Ghirabo, telepathic shapeshifters intended to serve as sexual playthings, able to read their owners' minds and assume a form and personality that will fulfill their owners' desires. But the Ghirabo's Creators were wiped out, leaving them to fend for themselves. In time, the Ghirabo have become a powerful race, creating...

Open in Reader

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

Mrs C

by pantywriter on Sep 11, 2017
Mature

This is a lengthy story covering many different subjects. Be warned that some fetish concepts are explored. ***** When Mr. Caruso next door unexpectedly passed away, I attended the funeral along with my parents. I think that the entire neighborhood turned out. The Carusos were popular, friendly people and his sudden passing shook everyone. It happened in...

One Sissy's Night

by Devient_Mind on Sep 16, 2017
Transsexuals & Crossdressers

As I walked out of the restroom of the suite you rented us at the Ritz Carlton, I felt nervous... I looked incredible, long blonde wig fixed perfectly ruby red lips to match my nails, long eyelashes and makeup done perfectly... My tight black dress plunging down my back and flowing to the floor. 4" stiletto heels... Thigh highs garter and they sexiest black...

Cameron SPH Multiverse

by Lady Revan on Apr 29, 2025

This story will be both a snowball story and also a place to write fictions and fantasy based on the porn videos,movies and works of Cameron kincade a male pornstar known for both his homossexual and feet videos and for his submissive videos where he almost always goes through some form of , sph, crossdress or cuck fetishism. He actually has a average dick i...

Open in Reader

Somali Hijabi MILF Doctor

by Samuelx on Sep 12, 2017
Erotic Couplings

Alright, I might as well confess at this point. I've got a thing for "mature" Somali women I see walking around wearing the Hijab and those traditional long skirts they wear. Every time I see one I get an instant boner. There, I said it. So why don't I feel better? As I sat inside Dr. Fawzia Hassan's office in downtown Ottawa, Ontario, I felt frustrated like...

Sometimes That's All You Need

by Hungry4aman on May 12, 2020
Erotic Couplings

This morning's headlines are not grabbing me. Typically, I wake up, fix coffee, and read the news. I am, typically, horny, and sex fantasies swirl through my mind like the steam swirling from my coffee. Like, how it feels to kiss and hug and grope a man's back and hips and ass and cock fully dressed. And how a man's ass can be so round and heavy with sex...

A Cross Dressers First Time

by webbyhose on Sep 13, 2017
Transsexuals & Crossdressers

I was in my mid 40's and divorced and living a great life. I ran my own successful from home and lived in a large house in it's own grounds at least 5 miles from my nearest neighbour. Whilst I was single I had an active sex life having been lucky enough to know 3 ladies who were unattached and had no need for a long term relationships but were happy to meet...

Sissyhood of Travelling Panties Ch. 03

by daddyslittlebitch on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 3: Carl Blake's mind could not shake the image of the pair of sexy red panties hidden in his room. As he ran down the stairs to answer his mom's call that Carl, his best friend, was here, all he could think about was the sensual scarlet satin of the boyshort panties with their red lace details. His mind could not help dwelling on how he had rubbed h...