Tranny Surprise Stories

136,341 results
Orientation
Length
Source
Infinite Scroll

Tranny Tales Ch. 03

by erectus123 on Sep 15, 2017
Transsexuals & Crossdressers

Maxie: The Tale of the Exploding Penis The use of the word Tranny is not meant to be disrespectful, it is used as it was in the past although not politically correct at this time. ***** Did you ever see the old film, "The Tattooed Man" or maybe it was called" The Illustrated Man?" Was it Rod Steiger who stared in that film, I really can't recall anything...

Sissy's Decline into a Slut Pt. 02

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Three: Another Exciting Night as Sissy Slut Wannabe. Well about a week has gone by since I bought the dildo, wrist cuffs, ice lock and the lubricants at the adult sex shop. Dressing up as a sissy maid or a sissy slut everyday at home and learning how to use the dildo first with my mouth and trying out the flavoured lubes for added pleasure, but most...

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...

Mia More

by seams_straight2me on Sep 16, 2017
Transsexuals & Crossdressers

It was 5 days after my very close encounter with Mia. I was still on very high spirit after meeting her, and fucking her. I could think of nothing else. We kept in touch via text messages and phone calls. She was "on location" for some photo shoot. One less about fashion and more about horny transsexuals having very sexy fun. She sent me a few pictures of...

Tranny Chasers: Shirley and Chrissy

by 1946EW on Sep 12, 2017
Transsexuals & Crossdressers

Shirley looked around as she entered Cavalier d'Eon, hoping to spot Ron and Bernie. She had promised that she would be there, and fully expected them to be waiting for her. Her survey caught the eye of many a hopeful tranny chaser. She had not known of the breed a week earlier, now she could spot them with ease. And there easily were over a dozen or two at t...

The Backdoor

by lfullback on Sep 26, 2017
Transsexuals & Crossdressers

It was only my first time in the club and my hands were shaking beyond control. I almost didn't make it through the front door I was so nervous. I felt so out of place. Everywhere I looked, it felt like people were staring at me, judging me. It was like they knew I had no clue what I was doing. I had heard about the place a few weeks ago. The Backdoor it wa...

Being Mindy Ch. 04

by mindyrose on Sep 15, 2017
Transsexuals & Crossdressers

In full disclosure, the following is not my first transgender surgery. I had my Adam's Apple shrunk in a previous surgery. However, that story was not one that led to lots of sex. Since this is a site for erotic stories, I have chosen not to share that surgery story. However, this one is about breast augmentation, which is a clearly sexual plot, and a fun se...

The Chuck Lutkus Story

by Sydney_Smart on Sep 1, 2017
Humor & Satire

My name's Chuck, Chuck Lutkus and yeah I do kill people for a living but I'm really just a regular guy you know. Sure I got a taste for the finer things in life. I like Ray-Ban sunglasses, Baracuta G9 jackets, Lactose polo shirts, Sansabelt slacks, Keds Champions, Browning firearms, white Corvettes, smooth jazz and shirley temples but if you take away all of...

A Latex Crossdresser's Dream Pt. 04

by shinyglove on Nov 18, 2019
Fetish

Please read A Crossdressers tale part 3 before moving on to this story. *** I slipped out of the sticky lubed up rubber, rinsed it and hung it on the rail to dry. Knowing full well I'll need it over the weekend. A quick shower and I jumped into our very large queen sized bed and began to nod off. Soon I was disturbed by someone squeezing in at the side of...

The Transvestite Stalker

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

The man sat at a corner table in the coffee shop surreptitiously eyeing off the woman sitting on a stool at bar. She was dressed in a navy blue suit; her jacket was open, revealing well-formed breasts swelling her white satin blouse, which opened to the second button so that a hint of lace bra was displayed. Her legs were crossed and her skirt had ridden up...