In 1975 I was a 22-year-old undergraduate with an undeclared major and no particular ambition or goal in mind. I liked to write, so I took a course in technical writing, which led to my first (of several) closeted crossdressing fails. In my mid to late teens, I had two hobbies ...
Today was a first for me, a big first too. I wore a skirt! In public! With people nearby! So what’s the big deal, you might say? Well, it was a big deal for me, let me explain. I’m in my 40’s, and besides you, my beautiful followers, and my wife, no one I know in rea...
I hadn’t given much thought to crossdressing the last 26 years. I can’t tell you why I quit, but I knew my belief in Christianity had been a large influence. That was back in 1988; I was 28 years old. Life passes and the year was 2014, I had separated from my wife and moved t...
I attempted to communicate the feminine side of me to my first wife. I am sure my attempts were feeble and no doubt unlearned. How could I help her understand about me what I didn’t understand about myself, had no objective evidence to prove it, and was such an antithesis t...
It’s been over five years since my wife died, and my world changed forever. The person who I was supposed to spend the rest of my life with went away, never to return. My wife knew all about me, the wanting to dress as a woman, and she accommodated me as much as she could, ...
“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...
There comes that time in your journey where you want to open up and share your feminine self with others in your normal life. Trans friends are wonderful, for sure, but you might sense that there will be something healing and transformative about sharing your secret self with you...
As I sit here in my red dress, with stockings and heels, and pretending that I’m at my job as an office secretary, I cannot help but to feel that this is an important part of me. I knew from a very early age that I was different from what I appeared to be. I started to expl...
My story is like so many other ladies. I started feeling the urge to dress at an early age. I found myself first touching and then trying on my mother and sister’s clothes. I usually felt shame, because as a child of the 60’s, this kind of behavior was taboo. I knew I...
Have you ever spent so much time focused on a project, or aspect of your life, that it feels like it is coming constantly unglued and now you are feeling an avalanche of anxiety because things aren’t working out right in this thing you’ve put so much energy into? It d...
If you have read my prior article, “I learned something that Halloween” you will be familiar with the context of this article, when I was 5 years old (https://www.crossdresserheaven.com/i-learned-something-that-halloween/). That Halloween I became the heartbroken tu...
Having kept Rebecca a secret for so many years, when I retired last October I knew that it was time to give her freedom. I began by visiting Manchester in the north of England for a few days. I took more female items (clothes, makeup and shoes) than male. I was still rather secre...
The confidence I’ve gained from telling her has even led me to be able to wear these panties under my male clothes in place of my usual boxers while I’m out and about. It is hidden yes, but this has been a huge step for me.
Chris has reached a crossroad in her journey. The darkness has become overwhelming - she is a breaking point. Thankfully, a friend is there to be a light and much more.
We are all on a journey. For some, that journey is appears to be surrounded by nothing by darkness, fear, and anger. Sometimes all that is needed is for someone to be a friend - a light showing through the darkness.
Regardless of from where we come or to where we are going, there is something that we all cherish. The path to its obtainment, however, is as unique and varied as we are. For some, it often remains elusive no matter how hard they seek it. Though sometimes, it may just be a mat...
Sometimes the person we are trying hardest to convince is ourselves.
I have talked about how young I was when I first Cross Dressed at the early age of 10 before becoming a Drag Queen, also at a very early age. Between the two I am proud to admit and say out loud that they are my life and there’s nothing in this world that can change that fo...
Don't mock the miss-matched clothes, poor makeup application, the male attributes too hard to hide, but instead notice the genuine smile and light in her eyes.
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