by
Tracy69
on Dec 3, 2019
Transgender & Crossdressers
Cast
Trace - me
Tracy - me, dressed en Femme
Rick - head of security at work, had just caught me masturbating at work, dressed as a woman
Ken - my roommate
Ok, ok, I hadn't mentioned this before, but my roommate Ken is gay. He would flirt with me from time to time, even hit on me, and I pretended to discourage him, but sometimes, late at night in my roo...
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by
Sissy_Chantel
on Sep 18, 2017
Transsexuals & Crossdressers
A quick note about this chapter. It runs a tad long as I want it to really set things up for Chantel's future, not just some sissy maid for her now Mistress wife, as cool as that can be, but to develop a more varied sissy, crossdressing, maid and slut story. I hope it works for my readers.
*****
Chapter Four: Moving on to reinforcing my new lifestyle
Satu...
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by
sissycrissi
on Sep 19, 2017
Transsexuals & Crossdressers
Chapter 3 -- Leroy's Turn
But Leroy had been left out for too long. Eager for his turn, I had no sooner finished pleasuring my Mistress when I felt his hands reach up under my skirt and start pawing my panty covered ass. Standing behind me, Leroy bent down and lightly held the back of my thighs in the palms of his large hands. He slowly slid his caress upwa...
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by
Red10Dog
on Mar 3, 2020
Fetish
This is a story from the sissy's wife. Telling you a story that happen a few weeks ago and it was orgasmic!
So late one Saturday night I put my sissy bitch in a teddy, nylons, cock cage and a jeweled anal plug under his pants and shirt and headed out to the casino.
I am not ready dress him out in public yet, but I am getting close.
I decide to slut mysel...
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by
latexdoll
on May 23, 2010
Fantasy
Waking up this morning I bet you didn’t know it would be the last day you spent here on earth.
Climbing out of bed you hit the alarm clock for the third time, you can’t quite place what is wrong, you just can’t seem to get out of bed. Getting ready for work is more of a chore than usual. For whatever reason nothing seems to want to cooperate. Your shower hea...
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by
SissyCuckMike
on Jan 2, 2021
Fetish
Hello everyone, my name is Mike and i am now a sissy cuckold. If you don't know what a sissy or a cuckold is i will explain, a sissy is like a cross-dresser but usually dresses up in pink frilly women's clothing and cuckolding is similar to a hotwifing where she goes out on dates and fucks other men without her husband/boyfriend around but with cuckolding it...
- 8,599 Views
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- Interactive
Open in SmutMD Reader
by
candyflosslover
on Jul 13, 2020
Loving Wives
The next day Jill was at work in her office, a parcel had arrived for her and when she opened it to her delight she saw it was a double ended dildo. She had ordered it some weeks ago so she could use it with her sissy husband. It was longer and thicker than she imagined and she felt heat between her legs at the thought of what she would do with it. She was s...
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by
Urtoy2be
on Sep 15, 2017
Fetish
Wednesday afternoon and work was slowing down for the week. Sitting in my office bored staring blankly at my monitor waiting for 5:30 PM so I could cut out. I need a drink went through my mind.
The weekend had been a blur. The events with my ex-wife and her new man had been crazy. Fantasies and thoughts had been awakened and now I was wondering who I really...
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by
UniversalReader
on Sep 26, 2017
Transsexuals & Crossdressers
AU:
The age of the characters in this story are not listed so that you can make the age fit you're desired age group. Assume by default that all characters are over 18.
Nathan was an average teenage boy. He was slightly shorter compared to most of his friends at school; but other than that he was average height. He was thin, he wasn't very muscular but h...
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by
econut
on Sep 16, 2017
Fetish
I had just finished cleaning up after dinner when the doorbell rang. Master and Mistress's guests were here. I had been instructed to let them in when they arrived. I was nervous as I walked to the front door. Gary and Lana, my Master and Mistress, had never had guests over while I was here. And until today, they had never made me dress in drag, and now I wa...
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