Someone once asked me why I like to crossdress, what's the motivation? I've thought a lot about this and there are many answers (in no particular order):
1. Women's clothes are so much more stylish than men's. There is more variety in the styles and fabrics. Just look in any catalog or clothing store. The men's section is about 1/3 as large. For example, women's pants have more style: they hug your curves; they have front, side, or back zippers; the legs are straight, flared, or wide; jeans pockets have designs on them; some are low-waisted; they can be stripped, other prints, embroidered; lengths can be long, at the ankle, or capri; and the same style could be made in silk, cotton, wool. Men's pants are baggy, usually just plain or pleated fronts, and there's not much more variety.
2. When I see a good looking woman wearing great clothes, or even just the clothes, I think to myself "Wow! She's very good looking" and "I'd like to wear those clothes!" I get excited. Today at lunch I saw this very pretty woman wearing a pair of red capris and black pumps with ~3" heels. They very much accentuated her assets (and leg-ets). I was equally aroused looking at her in a sexual way and envious of the outfit, wanting to wear it. I could use a pair of heels like those.
3. Crossdressing is a way of internalizing (for lack of a better word) what I love about women. Somehow by wearing women's clothes, I feel closer to women in general, but not in the same way as wearing a specific woman's clothes to feel closer to her. Is it the same as when people dress up as a Star Trek character and go to a Star Trek convention? No, not really. I'm not pretending to be a woman, nor do I wish to be/portray a woman.
4. I've a fetish for women's legs and feet, and the hosiery and heels that they wear with them. I read
Leg Show magazine all the time as it is specific to what I like to see. The fetish is what I believe started my on the road of crossdressing. In my early 20's I had (and still have) an enormous attraction to those things. At that time I was not dating anyone who was into wearing heels and hose, so all I could do was look. And where I worked there was enough eye candy to keep me in a constantly horny state. There were a few incidents that planted the thought in me to buy a pair of pantyhose. Soon enough I did. I first used them for masturbation. I wondered what it was like to wear them, so I put them on. It was like being struck by lightning! The feelings were overwhelming. Even the experience of buying them was a thrill in itself.
I started buying all types of pantyhose as I was interested in what other brands and styles felt like. I bought them from K-Mart, Wall Mart, Target, Victoria's Secret, Macy's, Banana Republic, Bloomingdales, and brands such as Hanes, Hue, Berkshire, and Leggs. For a while I was on a quest to find the best hosiery. One thing I've learned is that you are better of paying a higher price for better hosiery as they fit and feel so much better than the cheaper brands. Wearing cheap hosiery is a chore. Wearing the better hosiery is sensual and enjoyable.
When I first started buying pantyhose, I was nervous. I'd go to a store that was deserted and buy them as quickly as possible. But I found it to be an exciting experience. I slowly started to make sure there were other women around while I looked at the selections, I'd look for a female cashier or sales clerk. Buying soon became as exciting as wearing. It is fun to go to a store, look through the women's clothes, find a few things to try on, and then ask a saleswoman to do so. I have yet to be told no or have anyone make an overt fuss about it. The younger women tend to go back to the register, tell the other girls, and then giggle. A professional sales person realizes that treating a customer with respect leads to sales and higher commissions.
Then I wondered about other lingerie - panties, bras, camisoles, shapewear - and started buying and wearing those too. It also became a quest for quality. Who makes the best fitting panties? What fabrics feel the best? What styles are the most comfortable? I binged and purged my stash of clothes. It took some time, but I finally have settled down to just buying a few things every now and then, and I know what I like.
The outerwear - pants, shoes, blouses - came later. I was in therapy for a while. My therapist suggested that I attend a local crossdressers support group. I thought to myself "I can't go to a CD meeting in men's clothes" and dresses, wigs, and make-up are just not me. I decided that a pair or plain women's pants, shoes, and a blouse would be feminine enough for going to the meetings, but not too much. Again, after I bought the first outfit (from H&M) I was determined to find the right style for me. I went to Ross, The Gap, Banana Republic, Express, The Limited, American Eagle, Abercrombie, Old Navy, Aldo, Nine West, Famous Footware, Parade of Shoes, Payless, Target, and Macy's. I bought many things, wore them for a while, and later rather than sooner, honed in on the brands that fit me the best and felt the best.
