Crossdresser stories

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My First Women Client

As you all know am a cd mistress, I have 12 client 9 are cds and the other 3 are women who just love a male dressed in womans clothes.

Well my first ever experance with a my female client went like this.

We will call her Janet, she contacted me on yahoo , asking if I would meet her, as... Click to Read More

Loving The Lingerie

My first experience with another guy was many years ago, not planned, too much drink and then somehow ending up in a bed with another guy and things sort of getting out of hand.

Some years on I found myself more and more watching porn that involved women being gang banged and I imagined that I was... Click to Read More

How I Started...

I used to get into the AOL chatrooms and mess around all the time as a kid. I happened to find myself in a gay chatroom about the age of 12 years old. I seen someone on there as a CD and asked for a pic, he kindly sent it to me and little did I know that pic would end up changing my life forever! Like 90% of... Click to Read More

In My Dreams

You can feel your cock throbbing as you pull into the hotel I told you about. When you park your car, reach in the glove box and grab up the strip of latex condoms. 12 should be enough you think as you shove them in your pocket and shut the door. Maybe this long drive was for nothing, maybe I will stand you up... Click to Read More

Vicki'S Fantasy

Vicki was my ex-girlfriend, and she had dumped me when she found out about the cross-dressing, saying it wasn't normal. I was then surprised when she started texting me again, asking how I was and things like that.

We met for a drink and she still looked the same sexy young girl I had dated. She wasn't... Click to Read More

Lots Of Cum Three Cocks And A Pussy Too

All dressed up and no place to go, Oh well I just go out and see what happens. I'll pop in the video lounge and strut thru and check out the hard dicks, wow lots of them hanging around, I went to a viewing room with love a couch and leave the light on and the door ajar and see who... Click to Read More

Starting Out With Men

I started getting the urge for real cock while dressed in hose and heels and masturbating. I soon obtained a dildo, then two more, which I still have and which do wonderful service as substitutes! But I didn’t know how to connect with a man, except on sex dating sites, and I was too cowardly to take... Click to Read More

A Story From The Other Viewpoint

Hey all,

Well it seems that these are stories from the viewpoint of the ladies but thought I'd share something that happened to me.

First of all, I'm not into dressing and would never be passable anyway. But, I do have a fascination with someone who does..., and... Click to Read More

Discovering Cock At 48

When I was 48 I had a 25-year old girlfriend who was aggressive and experimental sexually. One day she wanted me to put on her panties so she could kiss and suck my cock through the nylon. She didn’t know I’d been a closet crossdresser most of my life, or that her idea almost made me cum thinking... Click to Read More

Cumming With Carl And Jerry On Friday

Carl and I spent all last Friday afternoon sucking and fucking one another, dressed in heels and hose and undressed. Friday night we got on his laptop and connected on a website with another guy I knew, who came over to the motel Saturday morning. Jerry and I had been together a... Click to Read More

Crossdressing Adventure

All my life I’ve been a secret transvestite, enjoying crossdressing off and on. Years would go by without me doing it, and then I’d do it a few times in a row. Now I do it at every opportunity. I wade-fish wearing women’s bikini bottoms and often wear women’s thigh-high hose beneath my jeans and... Click to Read More

My First Time With Crossdresser

I wrote a story on here on my first time dressing in pantyhose and heels and having my female friend make me suck her dildo. After a few months of doing this, I began to get curious on what it is like to suck a real cock. I finally did it with a super hot, petite, totally passable Transsexual... Click to Read More