I'd like to take this time to share a little bit of my experiences crossdressing and exploring into the world of transgendered people. Often I wondered myself if I was transgendered as I admired feminine clothing so much, I loved the female body so much I wanted to have the female body as my own. I realize this may sound some what selfish, but hey I'm a man and I like girls.
I've noticed one thing when it came to crossdressing, and that was it made me relax. I've tended to bottle up anger towards many people all my life and sometimes for maybe 15-5 hour sessions all of that anger would be relieved as I was dressed as a girl.
I often had dreams about being a girl, what was it like to have girls private parts rather than a boys, it must feel so different. For 10 years I've crossdressed, and only now have I started to look for psychological answers as to why I get my "kick" out of crossdressing. I would like to share all my findings with you because I believe in that one boy that is looking at this site right now wondering why on earth he is his sister's, mothers', grandmother's, or aunt's underwear yet he wants to be a boy on the outside but a girl inside.
I believe it to be that you are looking for your feminine self, and the only way you believe you can find her is through dressing feminine. I have found that the term "gender" does not necessarily come from what kind of physical body you have but how you think mentally.
The Male side, thinking more territorial, aggressive, egotistical
The Female side thinking more passive, gentle, and selfless
Whether your physical gender is male or female your brain will think in both perspectives (Male, Female).
When I crossdress I think nearly 100% female, and yet when I'm not I dismiss it like it was a shameful act. And crossdressers usually find guilt in what they do after they are done crossdressing especially if they masturbated while crossdressing.
I find that masturbating while crossdressing isn't truly getting in touch with your feminine side, rather I have found that its a desperate attempt to have sex with a woman who is not present or does not exist, and thus you take on the role as that woman, and imagine yourself being on the receiving end, and once you are nearly completely released you are back to yourself seeing you having sex with the woman that does not exist.
And the guilt sets in.
To get more in touch with my feminine side and build up self esteem in myself as I continued to crossdress I found that thinking like a girl while in girls clothes includes not masturbating. I began to feel rather disgusted at the thought of releasing when I was dressed up, and I began to feel disgusted at the thought and talk of releasing.
Now I see no reason to pleasure myself as a girl. I believe it to be helping me become a better man. Before I would look at many girls and think about having sex with them but now since I've changed my thoughts on masturbating while crossdressing I've begun to actually think like a girl in real time as a man. That was my first step. I now see girls and think "Wow she is pretty" rather than "I would tap that".
Many men who crossdress want to get in touch with their feminine side, and I believe I have just about found her, and I want her to have a bigger part in my life.
I don't know how much more crossdressing I will be doing, because it seems now that my feminine side is coming to equal grounds with my male side, and I'm not afraid to show it in public. No this does not mean walking around in a dress, but it does mean showing more feminine traits in public such as giggling, smiling, confident, and looking good.
I know this may have appeared to be a silly rant/statement but this is my experience that I wanted to share with regards to finding your feminine self through crossdressing and what may or may not help you.
Masturbating is a HUGE no no- girls don't masturbate (at least not the ladylike ones).
Act more like a girl in public but in moderation so you don't appear homosexual to society. So try to smile, giggle, be confident, don't think about sex, just live in the moment.