Continuing from the last part… Her parents thought I was a girl; I was wearing a girl’s swimsuit at the party and the skirt covered anything that said otherwise. I had medium length hair so they just believed I was a girl. I had to change, but since she wanted to keep up ...
Crossdressing Experiences
Crossdressing experiences out in the world, at home and in life. Crossdressing situations that will make you laugh, cry and appreciate the wacky journey through life as a crossdresser.
I’m going to start out by talking about how I started down this path of woman’s wear. At first, I was not like this, but was told later on that when I was between one to four years old my sister put me into a swimsuit or one of her old leotards that she’d outgro...
I had started going out on a previous trip to the southern US. I would go for drives, stop for gas, and pass though a drive through for food, what I think the usual starting out is for most of us 🙂 I was in Vegas for part of a week for a conference, and figured I would try a...
DANI’S DEBUT! By Caty Ryan Via Cross Dresser Heaven I have established a lovely friendship with a wonderful “younger” lady namely Dani Richmond. Dani and I have met for “underdressed drab” coffees for several months now, but she, unlike yours truly, has never been out i...
In mid-October 2018, I made a decision that changed my world. Up to then, for basically as long as I could recall, I’d had a curiosity about being a girl. I don’t know why; I just did. Even as a little kid, I’d stumble around in my mom’s heels. The family thought it was f...
Two cities, Toronto and Melbourne, far apart, but Caty Ryan brings them together in a delightful way, if you can understand her Australian slang.
Like so many of us, I started out as a child (BC). I became curious about the difference between men and women. While home alone, I decided to explore my mother’s fashion world. I rummaged through her closet and dresser drawers. I discovered that she was fashion conscious, and ...
Fun & Foibles in Vegas (or Travel “Tips” from a Relative Newbie and Wife)
Rochelle Mills Crossdressing Experiences 22Sometimes what happens in Vegas is too darn fun, exhilarating, and pleasantly unexpected and you just need to take it home with you. With the encouragement of some CDH sisters, my wife and I shared a two-day adventure as fun-loving girlfriends in this crazy town. If you feel ap...
The Gender Melting Pot that are Anime and Comic Conventions
Maddie Mooch Crossdressing Experiences 7So for years, I’ve been going to different Anime and Comic conventions within my area. I believe it was during middle school when I attended my first one, and it just continued on from there. I didn’t know at first that some of the girls in cosplay weren’t act...
Meeting my wife, Stacie changed my life around. I wouldn’t be here without her. Stacie’s support has made me realize how important it is to not give up. She has been there for me when I was down. There was a moment when my whole wardrobe was stolen by the 2nd of my ...
As some CDH members know, I perform onstage with Tokyo Closet Ball. Several of our members are also film makers. We are starting work on our third independent film. Recently, we had a screening of our second film to raise funds for the new project. The idea was to show the f...
It’s February 2018 and due to unforeseen circumstances, “She” has not been part of his life for almost three months. But as of today… “She” Returns “His SO” is away for the weekend; so after a restful night in a silky cami, French knickers, and pj’s she a...
Hi Girls, Patricia here! I want share some of my experiences dealing with shame and guilt I’ve experienced in my life with crossdressing and other endeavors. I’m sure most all of you will be able to relate to parts of my writing today! This may be more personal than we are ...
I feel as if I have both a girl and boy spirit occupying my same body. Since they live in the same body, it feels to them like a house or home they share in common. What is interesting, and I suppose natural is that the girl spirit likes men and the boy spirit likes girls. They b...
My beginning started 34 years ago at age six. I was the third oldest of five brothers; I wasn’t like them. They were the typical boys, masculine like, what most see as normal, and I was never that way. I started to like feminine clothing at four, watching my mom getting rea...
This past February, I wanted to try something new and up my crossdressing to another stage, but with any crossdressing session that I get to have, I need to be careful and wait for my house to go to sleep. It’s my secret from my family and I want to keep it that way. I wait...
No matter how we act upon them, most of us discover our need to embrace a feminine side at an early age. Often times our crossdressing sisters are drawn to girl toys, the activities the girls are doing over the boys, or sometimes in their desire to just wear pink. Simple pleasure...
I thought I’d tell my crossdressing tale in two parts. The second part, where I make my first public appearance as Carolyn hasn’t happened yet; it will happen soon, and how I got to that stage is a story unto itself. What were you doing last October? If we’d made a bet ...
This past October, I went out with the gurls from my support group to a new LGBTQ+ friendly bar en femme. I wore a loose black knit dress, stockings with garter belt, breast forms, ballet flats, tattoo sleeves, a cape, and a witch’s hat. It was Halloween! It reminded me of the ...
My earliest memories of cross dressing are circa primary school days. There was a trunk full of women’s clothes in the garage of our home; I seem to remember enjoying getting the dresses out and putting them on. My Mother also had an old pair of bathers in our laundry and when ...
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