Crossdressing Smoking Stories

17,384 results
Orientation
Length
Source
Infinite Scroll

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

The Agreement

by komrad1156 on Sep 18, 2017
Transsexuals & Crossdressers

Author's note: I prefer to write in the third person as it gives the writer so much more flexibility. However, I've written this story in the first person for one reason—it is my own personal story with love, marriage, crossdressing, and the ups and downs it invariably brings to a relationship. My name is David Calvin Peterson. My friends call me Cal. A smal...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

My Life as Isaac Newton

by Prizmatic on Sep 16, 2017
Romance

This character has nothing to do with the Isaac in Midnight Plush (q.v.). The idea for this story came in a dream, and that was his name in the dream, so I didn't change it. This is the closest thing to a traditional short story I've submitted, and I would really like solid critique on it. Especially, did I do a good job of writing from a man's point of view...

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...

Head Shrinking - Big, or Little?

by justincbenedict on Dec 9, 2019
BDSM

India smiled at the young couple. She loved seeing clients in this office. It seemed so cozy and the clients could cuddle while talking to her... It was a great couch. Reed looked a bit tense, but it had been months since he'd been out of his thing...of course when India thought of her husband and how long he had been in a tube, it didn't really give her mu...

Neighbor to Lover Pt. 01

by sarahchica96 on Oct 2, 2018
Transsexuals & Crossdressers

Introduction It was the summer I (Alex) and my twin sister Gina graduated from Business school, ironically Gina and I joined our family real estate business. This was a way of our parents keeping us busy and stop our procrastination about searching for jobs elsewhere. It was also the time my crossdressing persona met our neighbour Mr Parker. Backstory......

My First Time Dressing Ch. 01

by ChrissyCD on Sep 16, 2017
Transsexuals & Crossdressers

This is the first of hopefully many stories to come. This one may be a bit boring and lacking the hardcore fucking and sucking so many of you are used to. I feel the need to tell it because it will give some background to the rest of my stories. For the most part I will send them in chronologically from my younger days to present day as a undercover crossdre...

Everyone has a Freak Flag

by Etaindarcy on May 28, 2019
Transgender & Crossdressers

So for the most part, having sex while crossdressing is a bit of a fetish and once people know you are into it they are now free to share their own fetishes with you. That's where my next life lesson comes in and I have a couple of stories about people doing some surprising shit near me or to me. Around 26 years old, I was now going by the name Amanda and I...

Things That Turn Me On

by Raquels_Panties on Apr 22, 2020
Fetish

I'm a 28-year old male. I live a normal life in public. I like women and men. I'm 5'8" tall and weigh 135 pounds. One might consider my features, my face, my body shape, more on the feminine side of the spectrum, than on the masculine. I'm okay with with that. I use this to my advantage and have allowed my hair to grow out. It falls just below my shoulders....