by
Slipperylock
on Apr 8, 2019
Transgender & Crossdressers
It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...
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by
Stillherer
on Sep 16, 2017
Transsexuals & Crossdressers
The room is filled with the sounds of sex emanating from the wide screen tv. On screen a sylph of a gurl is on display all fours on a small low table surrounded by a sea of men in various stages of undress. The slim smooth skinned gurl is dressed in a short flared skirt that frames her sweet ass beautifully in layers of ruffles and lace with her pretty match...
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by
oneguy4fun
on Sep 12, 2017
Transsexuals & Crossdressers
Chapter 4 : Introducing Miss May!
Miss May's arrival seemed sudden and quick to Joe. He heard the door close downstairs. Then there was the sound of somebody running up the steps. The bedroom door flung open and before Joe could look up to see anything, he heard an excited voice exclaim, "kitty-kat!"
"I think someone is excited to see you," laughed Mistres...
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by
maturesubmale_for_F
on Apr 22, 2020
Transgender & Crossdressers
Dear readers,
This is a continuation of my two already published stories: 'Miss Johnstone's Lesbian Sissy Slut' and 'Further Training as Sissy Lesbian'. I sincerely recommend reading these stories first as it provides background for this one. My stories have been well received and I would like to thank you all for the positive response!
Enjoy and please ta...
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by
Sissy_Chantel
on Sep 25, 2017
Transsexuals & Crossdressers
Preface: Welcome to my next sissy story. This one is based around the exciting ideal of a married sissy, crossdresser. It will have many ideas based on my thoughts about how life could be for me as a married, crossdressing sissy maid. I hope you all enjoy it.
*****
Chapter One: Sometimes one's most unique secrets do come out.
My name is Phil and I've alwa...
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by
Sissy_Chantel
on Sep 18, 2017
Transsexuals & Crossdressers
Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel.
Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...
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by
Sissyhalo
on Sep 13, 2017
Transsexuals & Crossdressers
Finding a place in the city is rough sometimes for a good place honestly and I spent two years in a real shitty studio apartment with not even a laundry room in the building and just no room or increasingly no room.
And my luck turned around after I won money.
Seriously there's a 50-50 draw at work and just sort of on a whim I put my name in and I won. Not...
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by
subASIANsissyJADE
on Apr 3, 2019
Transgender & Crossdressers
Editor's note: this story contains scenes of non-consensual or reluctant sex.
*****
(I'm new here and this is my first post! I'd soooooo love to hear any feedback, questions, or comments! Many thanks, xxx, Jade)
*****
I wore exactly what he demanded - he told me to dress like a regular girl... he told me he had nosy neighbors and, being a married man, he...
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by
rik581
on Sep 12, 2017
Transsexuals & Crossdressers
Content Warning: To Literotica readers. This is a story of degradation and demeaning of the male sexuality as retribution for an extra marital affair. It consist of a strong female character and a wimpy willing male character. The sexual hypocrisy built in the story is intentional an meant to be part of the demeaning aspect. There is "NO" gay scenes in the s...
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by
Stillherer
on Sep 19, 2017
Fetish
Ms Shawna had rung. I had been summoned. As expected I was dressed as ordered and waiting nervously in front of the building when her taxi arrived, late. Ms Shawna was excessively infusive in greeting me as I climbed awkwardly into the back of the cab with her. The driver was a leering foreigner, with a manic smile who was far more interested in sneaking a l...
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