Transvestite Stories

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Grab Bag Transvestite Story

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

I am a part time transvestite, who, if I do say so myself, looks quite attractive when dressed as a woman. It has taken me years to become adept at makeup and being capable of selecting sexy clothing that is in my size and that suits me. I have also had a number of lovely encounters with other TVs and male admirers. You can read my True Stories on this site....

The Awakening Ch. 04

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

Part Four – Michele Returns The woman is slim. She is wearing a cerise satin blouse, black leather skirt and black high-heeled pumps. Flesh-toned fully-fashioned stockings sheath her long well defined legs. She is wearing a blonde bob, her bangs direct your gaze to heavily madeup eyes, and she's wearing glistening ruby-red lipstick. She is mature but sexy...

Maid to Order Ch. 02

by MicheleNylons on Oct 13, 2020
Transgender & Crossdressers

Mick had been shit unlucky. He had driven over sixty miles on the day she bought all of his girly accoutrements. He had even stayed overnight, confident that she wouldn't run into anyone that he knew while he was shopping. But, as has been said, he was shit unlucky. Of all the people in the world who happened to be in the same city, shopping in the same sho...

The Private Transvestite Detective

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

The Private Transvestite Detective (Or The Undercover Dick) With apologies to the writers of the various movies from which I borrowed some inspiration (and a few good lines). Chapter One It was late Friday afternoon and I sat behind my desk smoking a cigarette, leaning back in my chair with my high-heels resting on yesterday's newspaper. I contemplated m...

Michele Nylons' True Stories

by MicheleNylons on Jul 14, 2020
Transgender & Crossdressers

Introduction For those of you who only read fiction I suggest that you go directly to my autobiographical sex stories contained later on in this essay; but what I thought I would like to do is to take a break form my usual 'physically forced' and 'caught with consequences' Transvestite sex stories and write some of my musings about Transvestism and share wi...

T Ladies Orgy

by MicheleNylons on Sep 15, 2017
Transsexuals & Crossdressers

(T minus three weeks) Mike Harris called it 'The Quickening'. He had borrowed the term from the film 'The Highlander' where the quickening refers to the awakening of special powers that lay dormant in certain people until they are triggered by a significant event. Mike applied dramatic licence to the feelings that regularly overwhelmed him and called these...

Mistress Chantel, Tranny Dominatrix Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Prefix: Welcome to my next erotic story. This story will be written from the point of view of a Transvestite Dominatrix. It is a new twist in my mindset as I normally identify as submissive and as a sissy maid and slut to a dominant Master. It's my 'kink' but I have danced around in my mind a story from a position of Chantel being a true Transvestite Dominat...

Bisexual Black Man in The Hood

by Samuelx on Sep 15, 2017
Group Sex

Marcia Brown comes home from work. She's been working all day at the Cheesecake Factory and now she wants some rest and maybe a bit of excitement. She almost got fired today for getting into a long argument with Sarah, the skinny white woman who runs the place where she works. Marcia is a loudmouth who often snaps at customers when she gets stressed out. Als...

Michele And The Predator Ch. 03

by MicheleNylons on Jul 15, 2020
Transgender & Crossdressers

The Predator was stunned; it dawned upon him what had happened; he had fucked and been fellated by a transvestite. A man dressed as a woman! He looked at the pathetic sight lying before him on the bed and laughed. He thought to himself that she was just as good as any 'real' woman he had fucked; and she sure wasn't going to be telling anybody about this even...

The Devil You Know Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

Brian Davies sat on the hard toilet seat in a cubicle of the men's room on the twelfth floor of the building housing the large publishing company he worked for; he was reading the Daily Mail and trying to kill the last half hour before quitting time. As a middle-management employee he didn't really work mandated hours; he was expected to work whatever hours...