Tranny Stories

1,390 results
Orientation
Length
Source
Infinite Scroll

Recruiting of a Sissy Maid Ch. 13

by Sissy_Chantel on Nov 28, 2017
Transsexuals & Crossdressers

Chapter Thirteen: A Business Trip to an Adult Movie Convention, Carl and Chantel Consummate a True Loving Relationship. Carl says, "Chantel make sure you pack well but not slutty ok. I will have you travel with me as my girl friend and secretary. Dress nice but casual for our flight but of course still be an eye catcher ok?" Chantel replies, "Ok hun, I fig...

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...

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...

The Path to Happiness Pt. 09

by brendachaplin2000 on Sep 28, 2020
Transgender & Crossdressers

A couple of months passed since my weekend away on the film shoot. I wish I could say Chris and I become an item, but sadly I discovered he was already in a relationship with a girl and she was expecting his baby. My life already had too many complications without becoming the "other woman". On a positive note David had started a relationship with Adam, and...

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...

A Queen

by Eterriswolf on Jun 11, 2019
Transgender & Crossdressers

A/N: This is a fictional story. No characters in this story are under the age of 18 and they are not real people. Any similarities between the characters and real people are pure coincidence. In addition, this story involves activity between gender nonconforming individuals, one of which is a Trans Lesbian. If this is not something you are comfortable with...

Black Couples Love Tranny Girls

by Samuelx on Sep 16, 2017
Toys & Masturbation

How does a brother like me gets into these situations? That's what Haitian-born Canadian stud and Carleton University student Jean-Claude Etienne asked himself as he lay on the king-sized bed, getting his ass filled with cock. The cock in question belonged to Trina Ishtar, a gorgeous Transsexual lady whom his girlfriend Evelyn introduced him to. Evelyn, a ch...

Somali Man Discovers Shemales!

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

As Salam Alaikum, people. My name is Ibrahim, and I'm a Somali brother living in the City of Montreal, Quebec. I have something to share with you, ladies and gentlemen. I was raised in my ancestral hometown of Mogadishu, Somalia, and have been living in Montreal for the past ten years. I love Montreal, the best place in la belle province, even though I shall...