Tranny Porn Stories

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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...

The Virgin Tranny & the Bride Ch. 07

by yano on Sep 25, 2017
Transsexuals & Crossdressers

Firstly, on behalf of Roberta and myself may I thank you all very much for your very generous votes. We now continue Roberta's story and it is the morning after and tranny Roberta views the video of her big wedding day before a shopping trip and an exciting public photo call. * * * * * Next morning, I was awoken by a very excited John. "Come and see this...

Emily and Steve Ch. 09

by Travel_by_day on Sep 16, 2017
Transsexuals & Crossdressers

Over the next few weeks things really started to settle in at work. Emily was being more than accepted, she was being lauded. Emily, feeling much more comfortable as a woman, started being a much better worker. The quality of work that Emily was producing was far superior to Mike's work. She was featured on the company's intranet site as an inspiring story....

Danielle's First Time

by FellatiaViper on Sep 15, 2017
Transsexuals & Crossdressers

Danielle was born in the winter to 1976, but she was born a male by the name of Daniel. Daniel looked like a normal male child aside from liking girly things. Whenever Daniel would play dress-up he'd always dress in his mother's or his aunt's clothes and his parents thought that was cute until Daniel got a bit older then his father sternly told him, "boys do...

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...

Self Service Ch. 05

by prickasso on Sep 12, 2017
Illustrated

It was 3 weeks since the party where I performed in front of 2 dozen transvestites, sucking my own cock until I came. After that, Sonja, one of the she-males had propositioned me to film this as an instructional video for a porno company she worked for. I had just received an e-mail message from her company saying they would pay me a pretty good figure for a...

Husband's Transformation Ch. 01

by Prematurelimphubby on Jun 10, 2019
Transgender & Crossdressers

Brett was sitting at home alone while his wife Mandi was gone shopping. It had been a few days since their last sexual escapades. He was horny and he wanted release. He went to the bedroom and opened Mandi's drawer. He loved her panties and wore them often whenever he was home alone. In fact, he's even wore a pair while she was home. They were relatively t...

TS Prostitute Urge

by rodbulger on Sep 15, 2017
Transsexuals & Crossdressers

After college I began to explore the world. To that point I was the average male that happened to get a lot of tail. My sexual exploits with women were something I was proud of and always gave me a sense of being a real man. After years of watching straight porn and imagining myself in every possible scenario I began to become a bit of an adventurer. I fou...

Finding Release: The Sadist Dom

by ayrelia on Sep 12, 2017
BDSM

I have to say I was interested in him from the first message, but he only sent me a message to see about doing a photoshoot with my current partner, who is an adult internet entertainer. I should mention at the time, I was a photographer, part owner and graphic designer for five hardcore tranny websites. I'm a gg or a genetic girl, though. And yes, for all o...

A New Adventure...

by johnjinglez1 on May 16, 2018
Transsexuals & Crossdressers

I saw someone begin a "diary" of their experiences as a sissy on here recently and it inspired me to give it a shot myself. The following will be true stories from my past starting from the first time I ever hooked up with a Tranny / Cross dresser / Sissy. First things first, I consider myself to be a straight male; despite having had sex with all of the a...