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...
Crossdressing Success Stories are real stories from crossdressers who have succeeded in an aspect of femininity. Their success may be personal or public, but the lifelong impact is unquestionable. Each step on the way to success builds confidence until finally we can comfortably live as who we are.
As a child, I spent much of the summer with my aunt and my cousin. They were typical childhood summers, full of sunshine and endless days. I was young, so my older cousin had no worries about me seeing her in her undies, or even nothing at all. It made no difference to me either,...
“The world seems a bigger place when you wear a skirt….” “That’s one small step for man, one giant leap for mankind” quoted Neil Armstrong when stepping foot onto the moon. Although not anywhere near the scientific or cultural impact, for me steppi...
More about the open door later! Last summer, I finally acquired enough courage and came out to my wife who I suspected had her suspicions over the years in regards to my secret of cross dressing. A couple of years ago, she found a receipt for the first dress I had ever bought! H...
I was in Kohl’s today returning Christmas presents that were the wrong size. Did you know that Kohl’s has an Amazon return drop off? I thought that was pretty interesting. Part of my receipt was a 25% off coupon for anything in the store today. Well, a girl can’t pass...
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...
Excuse me in advance, but I so want to get this out. It’s funny actually; I’ve spent 40 years hiding and being ashamed of myself (I’m 50), and then after events during the last several months, I find myself wanting to just scream it from the roof tops. (Don’t get me wrong...
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...
The Next Step, and Amy says Goodbye to an Old Friend By the time the next month’s Pub Night was due to roll around, I had been out exactly twice. The first was Pub Night, and then at a small gathering held at a CD friend’s place. All went well both times, even though it had b...
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...
Well it had been a couple of weeks since my first time out in the world as Amy, and the glow from that first experience had of course diminished. I was eager to go out again, but I still didn’t have the courage or confidence to go out on a solo excursion. Plus, of course, that ...
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...
Amy meets the World, or at least a small slice of it. Like so many others here, crossdressing has been a mostly solitary pleasure of mine, from pre-teen to off and on through the years. I am fortunate in having a wife who didn’t mind my dressing, but it was only an occasional t...
Hi everyone! I wanted to share an amazing shopping experience that I had with all of you wonderful ladies. So my goal for the day was to get as femmed-up as I could and make a trip to Walmart to buy some stockings. I tore the only ones I had the night before so I figured basic li...
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So where am I? Who am I? March 30, 2020
It’s always difficult knowing where to begin. The start would seem fitting, but then again, I’m unsure at how to go about doing so. What I mean; when exactly was the beginning? As you might have worked out, I’ve been a little lost, and I like my philosophy. Perh...
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Permission or Notice and Modeling March 29, 2020
For the most part of my life, I have lived with a feeling inside. I was not able to identify it at first, but I just somehow felt smaller then… I am not a particularly tall person, so, I am generally shorter than most folks I stand next to, but this was different. I often felt ...
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A Life Born from Moments of Pain. (Part 1) March 26, 2020
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...
