Wearing My Grandmas Slips Crossdressing Porn Story Stories

352,637 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Porn at Work

by dan_tofuk on Sep 12, 2017
Mature

Fuck me, its hot! Its mid October and its still 82 degrees outside on the California Central Coast. Today is a Friday, and that means that no one else comes to work, except for My boss, his wife and me. That's a good thing, most of the time. It's nice and quiet around our little shop and I can sit at my desk and pretend to work while I read Literotica and sq...

Recruiting of a Sissy Maid Ch. 01

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

[Welcome to my next story. This story has become a little different in how I planned to write it as compared to my previous stories. It has been fully written up already, as of this first uploaded chapter. Doing it this way allows me to better proof read and adjust for future chapters before uploading each. I will submit uploads on a regular basis for my rea...

Encounters of a Crossdressing Slut

by KAshton on Sep 16, 2017
Transsexuals & Crossdressers

This is an introduction to my crossdressing experiences, touching upon highlights along my journey. I will write more about these, and other encounters in detail, in time. These really are all true stories, no embellishments whatsoever. I had always been fascinated with women's clothing, specifically tights (pantyhose) and anything silky and sheer, like sli...

Fetish Revealed

by ausielover69 on Sep 11, 2017
Fetish

My earliest recollection of my interest in womens lingerie was when I was 7yrs old I was playing hide and seek with my older brother in my Grandmas house . As I raced around looking for a hiding place in a panic I jumped into the wicker dirty clothes hamper. As I jumped in and closed the lid I landed on some clothes, sitting in there I was aware of a pungent...

Tammy Truth and Fiction

by TammyPanty on May 9, 2018
Transsexuals & Crossdressers

One of the elements of erotic stories is they are based in most cases in fiction. But most fiction is grounded in fact. I get several pieces of feedback about my stories asking me about certain experiences I have described. Not everything in each story has actually happened, but I have personally experienced more of what I describe than what is fiction. Fir...

Myra and Jack in Toyland

by ValoryG on Sep 11, 2018
Toys & Masturbation

Myra has had me, Jack, the one and only, wearing a Confin (chastity device) for three weeks now. She had announced brightly that she'd only have sex with me if I wore it. She'd read about using one in a little porn book passed around between her and her friends. I think they thought it hot and entertaining but only Myra got it into her head to actually liv...

The Suitcase Ch. 01

by SissyGeorgina on Sep 19, 2017
Transsexuals & Crossdressers

Enjoy the story, more to come, as soon as I'm able. It all started when I was 25. After graduating with a 2:2 degree in English from Plymouth University, I'd moved to London and gotten a job as a journalist for the Evening Standard. The pay wasn't great, and I was making next to nothing after paying off my rent, travel and living costs. I certainly didn't...

The Transition Ch. 01

by Quantarx on Jun 8, 2020
Transgender & Crossdressers

Greetings and thank you so much for choosing to read my story. This is intended to be a multi part series so bare with me as I try to develop the characters and lay down the backstories. As always, Your feedback is always essential in the development of the story going forward. Please leave a comment down below * I Had been Married for about eight years w...

Escapism: The Modern Man

by chasingrisque on Sep 13, 2017
Transsexuals & Crossdressers

*Synopsis: 25, in and out of relationships and one-night-stands. In debt, slightly overweight, unfulfilled at work and in life. Sick of his friends and routine, Alex accidentally reawakens feelings he has not had for a long time. Think Trainspotting for sissies - American Psycho without the violence and lot more lace, lip-gloss and high heels.* ESCAPISM:...

In For a Penny...

by TheHellWasIThinking on Sep 15, 2017
Fetish

To the reader: After I'd finished this story, I didn't know where to put it. It contains elements of several Lit categories, and I probably could have put it in any one of them. In the end, I decided to put it in Fetish, although it's very much a Loving Wives tale, as you'll soon see. NOTE: Every word of this is true. (Except for "Every word of this is true...