Tranny Stories

1,390 results
Orientation
Length
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Infinite Scroll

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...

Tom and T-Girl Lori 3 Way Scott

by THoward95th on Oct 6, 2020
Transgender & Crossdressers

Tom and Lori Have Scott This is part of an ongoing story over multiple Categories with common characters. Lori and I were getting to be a "thing". Sure, I sucked other cocks, but we had this connection. I thought she had almost said that she loved me one time, but that could open up a whole new can of worms. No, things were good as they were. Or so I tho...

The Virgin Tranny & the Bride Ch. 10

by yano on Sep 25, 2017
Transsexuals & Crossdressers

I'm sorry to say that this is the last episode in the series The Virgin Tranny and the Bride. It is far from being the final one but unfortunately Roberta has withdrawn the remaining story outlines and I had to fight to publish this one that I had completed on her behalf. The others I have had to email back to her. Why? The trouble seems to stem from some t...

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...

Waking Up with Brooke Ch. 01

by TheGuyInBlack on Sep 13, 2017
Transsexuals & Crossdressers

Tim was very proud to be a student at Penn State, but tonight he was in a sour mood. As a student, he was a die-hard Nittany Lions football fan, which made this moment particularly frustrating. The team had just lost a heartbreaker to Ohio State in double overtime after an incredible 4th quarter comeback by PSU. Sure, Ohio State was clearly the better team,...

Black Cuckolding: Haitian Style

by Samuelx on Sep 11, 2017
Group Sex

"I want to watch the two of you fuck because man to man action turns me on, there, I frigging said it," Esther Lubin said aloud as she lay on her king-sized bed, watching the hot action unfolding before her. The slender yet curvy, dark-skinned young Haitian woman fingered her already wet pussy, so turned on was she by what she beheld. The kind of action that...

Mistress Chantel, Tranny Dominatrix Ch. 03

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Three: My Saturday Meeting with Kerri. Well another busy but fun week for myself as Mistress Chantel begins to wrap up. It's a bright, sunny Saturday morning about 7:30am. My typical femme routine is to shower, dry off, moisturize with fragrant, moisturizing cream then to shave my face. Luckily for me in recent months I have begun to use a beard ret...

Friends with Benefits

by KittyandBear on Sep 13, 2017
Transsexuals & Crossdressers

It was late Saturday evening when Dave and Eric, shuffled home to Dave's place. They were returning from a party at the campus pub and were slightly inebriated. Eric had never fit in with the popular, party-going crowd in high school, but now hoped it was different in university. Dave had a nice apartment off campus, and Eric enjoyed the freedom of hanging...

Table for One

by cranesgirl on Sep 14, 2017
Transsexuals & Crossdressers

A/N Just a quick story. Not sure if I should continue? Please let me know. *********** I sat at my table for one at my favourite coffee shop watching the world go by the window. Each person with a look of intent, obviously eager to reach their destination. It was then that I saw her. My God she was beautiful. Whispers of hair framed her face from her lon...

Transvixen Tranny Rock Band Ch. 04

by MicheleNylons on Sep 13, 2017
Transsexuals & Crossdressers

Chapter Four: Substitute Cherri woke up on the couch at Wendy's place and her head hurt. Panti had obviously wondered off to bed sometime during the early morning after their prolonged fellatio session and left her alone to sleep. Cherri remembered that after they had made oral love they had argued about Panti sucking off Tony Carlotta. Panti claimed she h...