I’ve spent a lot of time on here today talking with people and reading stories, and I had the question asked of me: “When did I first know that I was like all of the other girls here”. I’ve thought about that a lot since, and it made me revisit my childhood and try to rem...
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.
Back when I was very young, i.e. browsing the Eaton’s, Simpson’s, or Sear’s catalogues and when done looking at all of the new toys I was never going to have, I would sooner or later come across the lingerie section. Great looking women dressed in bras, panties, sto...
Like many of you, I’ve had the urge to dress up in all the fun and exciting clothing that cis women get to enjoy ever since I was a child. Lovely pink dresses, satin ribbons, and the cutesiest hairbands. These were all things I wished that I’d had the chance to experience as ...
I’ve been meaning to write an article for some time now. But the moment I try to write something, it just goes out of the window, and I’m left staring at the wall or a blank screen, trying to catch the proverbial train that just left the station. On the other hand, standi...
In these times of restrictions and lockdowns (that hopefully will soon be a thing of the past) I thought it might be a good time to provide a compilation of my writings about my first time attending a CD/TG conference since many of our current members weren’t around back in 201...
Hi all you lovely ladies out there in CD land. I just thought I would put a little ditty on here about keeping everything clean and smelling sweet. We don’t want smelly knickers or underwear, do we? I Just love the sweet smell of clean fresh clothes, the feel of smooth satin ...
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...
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.
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Holly’s First Halloween November 23, 2020 A dream come true… I can’t tell you how long I’ve longed to experience what it would be like to be one of the Disney Princesses. Those elaborate beautiful ball gowns, the petticoats, the beautiful shoes, the layers of hair…elegant, beautiful, breathtakin...
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The Vicarious Woman: Part 1: Crossdressing YouTubers November 21, 2020 Definition of vicarious 1: experienced or realized through imaginative or sympathetic participation in the experience of another a vicarious thrill (Merriam-Webster) My intention here is to start a group of wiki-lists of favorite places to enjoy vicarious fulfillment from o...
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My Season of Doubt and Shame: Part 1 November 21, 2020 This is a two-part story, written as a conversation between my male and female personas. It is based on my personal struggles with certain erotic aspects of my crossdressing. This is not discussed often at CDH, and I’ve tried to be discrete. My orientation is overwhelmingly mal...
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