Transsexuelle & Crossdresser Stories

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The Hitman Wore Heels

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

The well dressed man looked with disgust and loathing at the bum rummaging in the dumpster in the dark alley. Tony 'Tough Tony' Provalono had just left Scalini's, one of the best restaurants in New Jersey, where he had tipped the waiter more money than the hobo was likely to see in his lifetime. Tony was dressed in Armani; the gorgeous woman beside him in Pr...

Missing the Cut

by thrillerauthor on Sep 17, 2017
Celebrities & Fan Fiction

© 2003 by Thrillerauthor FORT WORTH, Texas - The eyes of the sporting world are on Annika Sorenstam today as she becomes the first woman golfer in over fifty years to play on the PGA tour. Although most of the men playing alongside her in the Colonial Open have been supportive, Denny Grimes has made no secret of his disdain. The diminutive Grimes, who has w...

The Robertson's Sissy Ch. 10

by Clite69 on Oct 7, 2019
Transgender & Crossdressers

**A quick note. The chapters of this story can fall into multiple categories, group sex, reluctance/nonconsent and transgender/crossdresser. If any of these are not your taste than this story may not be for you.** ***** This was becoming the best day of my life. After all the crap I had been putting up with things were finally turning around. Lela and I we...

The Surrogate Ch. 02

by MicheleNylons on Jan 20, 2020
Transgender & Crossdressers

Chapter Two - Becoming Mila Mila slept in a satin nighty and panties that night but she was untucked of course. There was no sign of Peter Randal and she had the apartment to herself. She had practiced her makeup for a while and walking in heels and then after a light dinner she retired. She had tried on her sister's clothes and divided them into two piles...

Cunt! Ch. 08

by chandler831 on Dec 2, 2019
Transgender & Crossdressers

Around six in the morning I awoke snuggled up against Mark, his arm draped over my body and my ass pressed against his crotch. I was wearing only my bikini top. Realizing how incredibly incriminating this might look if his parents happened to wander into our room, I scooted out from under his arm, got up, took off the bikini, and threw on some athletic short...

Violation

by MicheleNylons on Jul 15, 2020
Transgender & Crossdressers

I have been home from work for over an hour; I lift my head from the brief that I have been reading by the light of a desk-lamp. The room is full of shadows. I look at the antique clock on the mantle and see it is approaching eight o'clock and I look over at the window; it is dark out. I close the file on my desk and then close the curtains in the study. I g...

This to Keep Me Quiet Ch. 02

by MicheleNylons on Oct 5, 2020
Transgender & Crossdressers

Chapter Two - I Am Yours With The Following Caveats When Michael finally escaped the investment meeting he scurried back to his workstation. Stills and Shipley had installed the latest technological advances in their offices and each of the staff had their own computer which was linked to the office network and some were linked to other financial institutio...

My Metaphor

by hyperpress on Dec 24, 2018
Fetish

The audience drops into a continuing story written in first person POV (mostly). The following based on a true story. Given enough time, any question that occurs to the reader shall be answered, eventually. * I woke the next day, showered, put on a comfortable chemise, a microfiber and nylon blend thong and open toed sandals, made some coffee and sat down...

Neglected

by komrad1156 on Sep 13, 2017
Mature

*Author's Note: Two quick points. As I've said, I know from personal experience, older (even married) women will sleep with a younger man. Falling in love and actually marrying one is an entirely different thing. Without a job to support them, it's even more unlikely, and there are only a few jobs someone between 18-22 can have that earn enough (not a lot—en...

Coming Home, Coming Out Pt. 10

by EiryCGar on Jul 6, 2020
BDSM

Author's note: This chapter marks the end of this series, which seems to have run its course. I am grateful to my readers who have commented on my story. As ever, I should remind them that this is a work of total fiction. All characters are at least 18 years of age, and everyone who participates in any of the sexual practices described does so consensually....