Tranny Stories

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Orientation
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Infinite Scroll

The Virgin Tranny & the Bride Ch. 08

by yano on Sep 25, 2017
Transsexuals & Crossdressers

My transvestite friend Roberta writes to tell me that recent surrender of her boy pussy to her Master was, sadly, not for love but as a means of gaining embarrassing video footage to use as sexual blackmail. Master John is now teasing Roberta and she is about to embark on a new career as a call girl and prostitute. She writes: With the lining removed and m...

Becoming a Sissy Maid & Slut Vol. 10

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Seventeen: It's time that Chantel Earned Her Keep. Well it's the morning of a Saturday, to where by night time I will soon be doing some true sissy slut street walking and now truly begin to earn my keep and begin to earn some serious money for my Master. I awake like all other mornings at 7:30am and follow my morning routine, enema, shower, shave...

Twenty Questions

by DrLuverotica on Sep 19, 2017
Transsexuals & Crossdressers

THURSDAY I was just settling down to watch a movie when my wife arrived home after a night out with her girlfriend's. "You're home early," I said. "Lucia had to be back by ten. She's on the early shift." "Meet anyone else?" "Just a couple of hunks - they're coming over for supper later." "Very funny." "Actually I wanted to come home because I was feel...

Master is Going to Cum Now

by Manndee on Apr 28, 2020
Transgender & Crossdressers

I had searched online for months to find a friendly like-minded group of people that I could communicate with and share my unique desires. I thought I had seen them and signed up to several dating type agencies that offered me the perfect match. The agencies then sent me non-stop emails from people that matched me. The people were not interested or simply di...

Caught In the Tranny Master's Web

by CarrieQ on Sep 16, 2017
Transsexuals & Crossdressers

One of the nicest things about living in London's West End is how you can look out of your window at all the glitz and glamour, and feel like you're right in the middle of something big. And if something as big as Kurt's 14-inch cock happens to be pounding in and out of you while you look, then doesn't that just take the biscuit? An over-endowed black Germa...

Samantha Meets a Dom Master

by SamanthaSatine on Sep 16, 2017
Transsexuals & Crossdressers

A true story - I am the main character and all the various activities described were undertaken with my consent...no harm came to me in any way... ***** The date was fixed. The room was booked – neither of the willing parties could accommodate, a not unusual event in the world these two inhabited from time to time. The morning of their meet had now arriv...

Wandering Gem

by dkleiman87 on Sep 15, 2017
Sci-Fi & Fantasy

The ruby glowed in the stores fluorescent lights of the old thrift shop, shooting beams of red against the countertop as James walked by. The glint of light catching his eye as he passed, drawn into its radiance he reached out and gasped at it. "Excuse me?" he asked the woman texting behind the counter, "How much is this?" The girl unenthused by her annoyi...

Black Women Love Transsexuals Too

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

A lot of girls out there are turned on by transsexuals, and I'm one of them. My name is Raquel Dawson, and I'm a young Jamaican woman living in the City of Ottawa, Ontario. I study psychology at Carleton University, and I'm a gal with a pretty ordinary life. My family moved to the region of Ontario, Canada, from Kingston City, Jamaica, in the summer of 2007....

My First Time with a Tranny

by daddydick89 on Jun 4, 2019
Transgender & Crossdressers

This is a true story. It happened on a Monday morning, after waking up with a throbbing hard-on. I called up my regular booty call. But she couldn't make it, because her husband stayed home from work that day. So I decided to browse Craigslist, looking for someone local. After posting my ad, looking for NSA sex, I sat back and waited. Within minutes, I re...

ESTIM Experiences Ch. 02

by jy55 on Sep 12, 2017
Toys & Masturbation

Since my first story, I have developed into a real estim freak. My daily pleasures are such that my body almost 'knows' that it is time. I generally masturbate every morning anyway, but estim is almost always the usual method. I have taken to looking at online porn the whole time as I stimulate myself for at least an hour daily. The sensations are so exqui...