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...
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.
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...
I know Halloween is over, but my saga isn’t! So please indulge me for a little while longer… Despite my mental breakdown after the Lady Gaga adventure, my interest in crossdressing only got deeper and deeper over the following year. I began purchasing more and more of...
I hope you had a chance to read Part I of my adventure. It was a scary, but an exhilarating experience for me. As I wrote in Part I, I was on a huge high from having success beyond my expectations, and I didn’t want my day to end. I’m an older crossdresser- 6̵...
Every Halloween, post-Sarah Palin, I struggled to come up with a costume. Because deep down inside, I just really wanted to go en femme again. But I felt that crossdressing for Halloween when you celebrate with your “regular” friends was a “one and done” d...
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...
October is here, and we all know what that means! October 31st is right around the corner, and yours truly, like many of us, think of Halloween as unofficial “Crossdressers Day,” and with good reason. Most of us have struggled, sometimes for many years, with wanting...
Two cities, Toronto and Melbourne, far apart, but Caty Ryan brings them together in a delightful way, if you can understand her Australian slang.
Or as Paul Harvey used to say, “And Now for the Rest of the Story.” This is a follow-up to my “First Time Out” article. As part of my preparation for my transformation, I packed my large breast forms, sized for 40D, in my suitcase. (Those must have provoke...
This past summer I found myself on an extended trip to Australia for work and knew that there would never be a better opportunity for Alexis to step out into the world for the very first time. It’s about as far from home as I could possibly be, so no risk of running into some...
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)
, , Crossdressing Experiences, 21
Sometimes 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...
So 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...
This is 40 years of how I mostly came to be where I’m at today. I left out the back stories of burying two daughters, 20 years apart, and the struggles with addiction and depression; 50 pages couldn’t tell my story, nor come close to counting the tears I’ve shed...
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...
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Recent Articles
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Walking The Lonely Road January 18, 2020
I, like so many others who knew from early on, I was meant to walk a different road. As a child, we kids would play from dawn to dusk. We played all kinds of games and my fave was always dress up. The girls would make us dress in their clothes and they would do likewise with our ...
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Going out in Vegas January 18, 2020
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...
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Finding Your Way January 16, 2020
I am sitting here, having a nice glass of wine, contemplating my future. I am a torn individual. OK with my male life, yet wanting more. I just feel more alive when I am April, yet I am so self conscious of my appearance. I know I do not pass and while I am OK going out part time...
