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From a Husband to a Dutiful Sissy Ch. 07

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel. Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...

My First Time Dressing Ch. 01

by ChrissyCD on Sep 16, 2017
Transsexuals & Crossdressers

This is the first of hopefully many stories to come. This one may be a bit boring and lacking the hardcore fucking and sucking so many of you are used to. I feel the need to tell it because it will give some background to the rest of my stories. For the most part I will send them in chronologically from my younger days to present day as a undercover crossdre...

Sweet Alice

by Akito01 on Sep 13, 2017
Transsexuals & Crossdressers

It is typical in these sorts of confessional stories to change names to protect the innocent, but in this case the concept of 'innocence' barely applies. That said, I will refer to my friend here as Sweet. If you're old enough to remember the singer Matthew Sweet, then hopefully it won't seem too odd to call him that. I think the gender ambiguity of that nam...

Webmeets Diary Ch. 04

by starbelliedboy on Sep 14, 2017
Transsexuals & Crossdressers

Note to the reader: In this diary I will tell the true stories of my sexual encounters that have come about thanks to the internet. Some more precise details such as names and places will be left out to protect mine and others privacy, and also because they don't matter, but otherwise I will try to be as accurate and truthful as possible. As I neared the en...

Obey Thy Neighbor Ch. 04

by jealouscuck on Oct 24, 2018
Transgender & Crossdressers

After I had witnessed Cecil and Li fucking I began worrying about what Chelsea might be missing out on. After all my cock was less than four inches long when erect. Seeing his massive cock penetrate Li's pussy and seeing her pussy afterward I was feeling so inferior that I almost wished Chelsea could have that type of experience. One of the reasons why I was...

Becoming Mindy

by mindyrose on Sep 18, 2017
Transsexuals & Crossdressers

Hi. This is my story from an unsure, shy, awkward boy that was pretty feminine to a proud, confident and comfortable transgendered girl. If you're not into reading about transgendered people and their stories, as well as their sex lives, then please move on. I know I made some foolish decisions, but I am a completely healthy person today and those decisions,...

Aileen Ch. 01

by TiffyKitty93 on Sep 19, 2017
Transsexuals & Crossdressers

~The following is just a fantasy. Any actual names or likenesses to real persons or events in entirely unintentional and coincidental.~ Rain. Oh how I hate the rain. Only bad things have ever happened to me in the rain. Two years ago, when I was sixteen, My parents argued and decided to get divorced in the middle of a rain storm. However what happened in...

Roomers Ch. 02

by grgy56 on Jun 18, 2018
Erotic Couplings

While separated from my wife and needing a place to stay, my friend Rick allowed me to stay in Harry his son's room temporarily. Rick was now divorced and living with his current, Tina. Tina was a very tall, very skinny Taiwanese with small tits and a nice shaped bum. She was a licensed RMT so when I injured my back lifting some heavy crap, she offered me a...

Jeff Crossdresses More & More

by TurningintoCD on Sep 12, 2017
Transsexuals & Crossdressers

My name is Jeff. I date girls every now and then but I always masturbate about dressing up as a hot chick and seducing a hunky guy. My biggest turn on is putting on women's clothes and makeup. I never really had a chance to explore it much when I was growing up. In college I had a secret stash of 1 stick of lipstick, and when I felt really dangerous, I wou...

Passion over Lust

by sarahchica96 on Sep 5, 2018
Transsexuals & Crossdressers

Introduction I' am living the dream, the dream of maintaining the balance as a regular straight guy and my bisexual crossdressing side Sarah. The 4 years of hard work at University started paying dividends, I landed a job as a legal advisor for one of the top businessmen in London Mr Hayat. My job paid well which enabled me to buy a studio apartment via a...