I’ve been sooo frustrated these last few weeks, unable to dress because I never have the house to myself during lockdown. My wife knows I dress, but has always said she wants nothing to do with it. She could see I was unhappy, and when she asked me why I plucked up the cour...
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.
Me? How old was I? Old. Probably 28 or 29, maybe 30. I was long passed the time when the clothes were an end in themselves; and being Cassie in the world, in public, was the wonderful pleasure. I had long since decided that I wasn’t a transsexual, but that the occasio...
I have been thinking about writing an article for some time now but going back and forth about a subject. I guess during these troubling times of a pandemic and self- isolation and self-reflection, the topic now seems appropriate. Like other girls I started my fascination with cr...
I believe the best of thrills of crossdressing are the moments before and after you step out in the world dressed as woman. But each time you do it, it becomes more normal, causing us to push ourselves more and more to achieve that thrill. Eventually, you end up going out wearing...
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 ...
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...
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...
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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.
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...
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Tell Your Girlfriend, But Don’t Tell Your Wife July 9, 2020 I have no doubt that this will be a controversial article (and opinion) on Crossdresser Heaven. (I do so look forward to reading the comments.) The common wisdom in our community is that a crossdresser who is in a marriage or serious relationship with a genetic woman is best o...
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Confronting Fear July 9, 2020 and how it changed my life Let me start by defining Fear: Fear is an emotion and as such can be controlled. It can exist at many levels with varying degrees of effect on our lives and how we behave. It could sit quietly in the background until the switch is flipped by a visual, a...
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My Prayer July 5, 2020 My wish for the future, a Prayer for Hope, Peace and Acceptance These are a few of the thoughts I’ve had over a long time. They contain a little bit of my whimsy, but the wish within and the desire for all of you is true, particularly now for people of all race and colour. You ...
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