I was trying to write a great big bio to give background to my problem but it wouldn't fit on my profile

In summary, I have occasionally crossdressed all my life (am now 40), usually at times of stress or when I've felt lonely. About a year ago, as I approached 40 it finally hit me that I'm a 40 year old virgin whose shy and lonely. I tried a dating site, exchanged one or two emails with prospective dates and then put a photo on the site. Never heard from anyone again. I know I'm not attractive, but didn't realise (or was in denial) that it was that bad. I'm short, overweight (not obese, just carrying a few extra pounds) and socially inexperienced. Never had a date and have few friends.

The cross dressing has become a daily, permanent state. I suspect that the feelings of loneliness are being expressed in the cross dressing. I think I'm craving female company but lack the confidence or knowledge to know what to do about it. I've always been attracted to women but guess I don't really know what my sexuality is, having never even kissed, dated or even held a hand. I'm not too worried if I turn out to be gay or a transsexual (or whatever the correct term is) as long as I know and can find happiness in myself as I don't think I really know who I am.

Can anyone suggest anything that would help me overcome shyness and a chronic lack of confidence in social situations, or a way in which I can find out who I really am?