(Please forgive the poor photo quality; at night pictures are difficult) I have now experienced my first time of being crossdressed outside of my home (in the outfit pictured). I wanted to share my experience here, as I’ve been reading and appreciating other people’s ...
Crossdressing Experiences
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.
Hi everyone!! My name is Bren. I want to introduce myself and share my crossdressing story. My journey began at age five, 53 years ago. My best friend was the girl who lived next door. We played together all the time and I would wear her ruffled black dress in our backyards. We p...
My crossdressing journey started when I turned 12. I went with my family on a holiday to the beach. One day, as they were all off swimming, I stayed home to sun-bake. For some reason, my mother had taken my swimmers with her in the car. I had the choice of sunbathing naked or in ...
Pretty Pink Panties
Sabrina (Brina) MacTavish Advice and Encouragement, Crossdresser Support and Advice, Crossdressing Experiences 80I’ve written several articles for this site; most are my own musings about who I am and where I fit in. I write to find myself, and I write to help others think through their own situations and feelings. As an introvert by nature, I sit back and take it all in, process it, ...
For as long as I can remember I’ve felt like a girl. When I was young I would pray to God every day to turn me into a girl. I prayed so hard for it. It never happened of course, but she was always there, inside me. I called her “Amanda” because this would have b...
I have been supremely calm and at peace with myself since I not only decided that I would start crossdressing, but that I wasn’t going to keep it a secret, either. That was eleven days ago when Mitzi May introduced herself into my reality. Or, rather, actualized herself in ...
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...
The transformation of my crossdressing also transformed my health and life. This is the story of that transformation.
I am a very shy and keep-to-myself man. But when I let Holly out, she’s everything I want to be but not allowed to be by society! Playful, sexy, cute, girly, silly, loud, daring, etc! Normally this girl is very much kept in the closet…well, this girl went tempor...
Sometimes life seems to be working against you and you can be denied the opportunity to be your real self. Christina has lost herself to people and circumstances. She is working to get get back to her real self.
An email in the inbox of the crossdressing association in Frankfurt. My fingers tremble as I open the mail, for the sender is no one less than the “Frankfurter Allgemeine Zeitung”, one of the biggest newspapers in Germany.
A Day at TGMiss – The Ultimate Makeover Transformation Experience
Gina Angelo Crossdressing Experiences 51Most of us have a vision of how we see our feminine selves, and when we find the right people to help us realize that image of ourselves it can be a dream come true. Gina fills us in on her vision realized.
Cleaning The Closet: A New Year Beginning
LaWren Peace Crossdressing Experiences, Crossdressing Just for Fun, Uncategorized 12It had been 15 years. It was time. Time to indulge Lorie. Time to celebrate her. Time to welcome her home.
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...
Cynthia relates her experiences before and during Keystone, and in getting together with fellow travelers on a journey we all share.
Growing up, I knew that my mom had wanted a girl first, but she got me. I know now that a part of her resented the fact that I was a boy. My parents got divorced when I was 7 or 8. After the divorce, we moved quite a bit and mom wouldn’t let our dad see us for at least a ye...
My journey probably started like so many others. I was nine years old and it was the 1970s. I was never into the boy things, such as motorbikes and sports, and always wanted to hang around with the girls or just sit by myself and admire how they dressed. It was a fascination ...
Hi everyone! I wanted to share something that happened to me a couple of months ago. First, let me briefly give you some history. I began thinking about crossdressing around the age of 13. I noticed that women had so many products made for them to look pretty, look sexy, smell go...
Most of us dress for the first time with clothing from relatives, a significant other, or wherever we can get a piece of clothing discretely for the first time. But there comes a time when both the need, for a completely personal wardrobe and the desire for one, arises. You can p...
I only started crossdressing in my early fifties. So what happened? Why did this happen "out of the blue"? The whole experience has caused me to ponder these and similar questions on numerous occasions.
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