As a crossdresser myself, I have had a number of questions about myself and others in the crossdressing community. The questions for others were more to satisfy my curiosity and to gain knowledge. Perhaps these are some of the same reasons why you read my blog. As for the questions I have for myself, they look into my motivations, reasons, and dreams. Why crossdress? I answer some of these questions in this post. Don’t you have some of the same questions for yourself?
Q: When did you start crossdressing?
The answer to this question depends upon whether it is occasional dabbling in crossdressing or full-blown crossdressing. The latter started about five years ago. That is when I started to buy women’s clothes on a regular basis, as well as trying to learn how to look as close to a woman’s appearance as possible.
Before that, I guess you can say that I’ve dabbled with crossdressing since my childhood. My interest had less to do with women’s clothing and more to do with women’s jewelry, especially rings.
I remember being fixated by my mother’s wedding ring when I was an infant, one of my few memories while at that age.
One of the most transforming events in my life happened when I was about 10 or so. We got to play Dress Up with my mother’s jewelry chest. I was in love with wearing necklaces and rings, to the point where I would sometimes sneak into her bedroom to wear some even for a few moments. This isn’t crossdressing in the traditional sense, with wearing shoes or dresses, but I still consider it a type of crossdressing. After all, boys didn’t wear rings to school, did they? That’s what the girls did!
Q: Why do you crossdress?
Why crossdress? This is the question all of us crossdressers ask ourselves, and it is probably the most difficult. Being that I haven’t seen a counselor, I’m going to have to make my best guess .
When I eased into crossdressing more regularly during the past five years, I have found a sense of liberation. In a sense, I feel that I am not hemmed in by society’s norms when I crossdress. This is not to say that I enjoying flouting society’s norms, far from it. However, I can say that it bothers me when society does try to impose its norms upon everybody who is different. In a sense, crossdressing is my way of giving society “the finger.”
With this freedom of expression, I feel that I can express myself more fully. I can give people a glimpse of the real me, in a way I couldn’t while dressed according to male standards. My personality has always had a lot of traits that are more feminine. I don’t like confrontation. In addition, I feel that I care very much for other people, including people I don’t know well. My personality is more nurturing than the typical male.
In a nutshell, dressing in a feminine way expresses my inner being better, despite what society thinks about it.
Q: What do you like most about crossdressing?
With the dressing itself, I really enjoy exploring the different styles and fabrics. Dressing as a man does not afford those opportunities. I don’t get to feel the breeze under my skirt when dressed as a man, nor do I get to feel the soft fabrics against my arms. I feel like a kid in a candy shop, with so much to explore. This is one of my key answers to the question: Why crossdress? I suspect it is for many of you as well.
The other thing I like about crossdressing is the new perspective it gives me. I have always considered myself a feminist, but my perspective changed as I began crossdressing more. I am not a woman, so I’ll never know exactly what women have to endure, nor will I understand exactly some of the joys they have that men do not. Regardless, I feel that I have a deeper understanding and appreciation than I used to have. For that I thank crossdressing.
Q: What is your biggest fear about crossdressing?
Although I have become more accustomed to being out in public, I still feel very uncomfortable having one-on-one interactions with others. I don’t mind being in a crowd, but chatting with someone in that crowd really stresses me, a lot!
I also have a big fear of going into a women’s restroom. As I have said, I avoid confrontation at nearly any cost. I am sure in most cases there wouldn’t be an issue. My concern is how I would react if there were a confrontation. My goal isn’t to make other women uncomfortable with my being there.
Q: What are your crossdressing goals?
I would like to spend more time in public. Why crossdress in public? The main reason is to overcome that fear of one-on-one interactions. Being an extreme introvert all my life, I have been very self-conscious about my interactions with other people. However, I have learned to do better as a male. It took a long time, but it is vastly better than now. I just need to learn the same when presenting as a female.
To make this easier, we are planning to move to a larger city (Las Vegas, Nevada) this summer. This city should give me the room to grow as a crossdresser. No city is perfect, but I expect it being better than the small Midwestern town where I am now.
Why Crossdress? Don’t we all have our own questions?
I’ve answered a few questions about myself. Hopefully you found them informative and not boring. I’d like to think my crossdressing quirks are interesting to others.
But now, dear reader, I turn the tables. Think some about how you would answer these questions if someone asked you. What’s your crossdressing history? Why do you do it? What are your dreams and fears, and are you going to something about those dreams and fears? Now that’s an interesting story, isn’t it?
p.s., Here are some of my other popular Sami’s Week posts. Enjoy!
- Limited Crossdressing Opportunities – Sami’s Week
- Crossdresser Shopping Trip with a New Friend – Sami’s Week
- Sami’s Week: Dealing with Fear as a Crossdresser
What did you think about this very personal post? How would you answer some of these questions? Leave a comment.
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