Prior to discovering the online network of crossdressers seven years ago, I was wearing panties 24/7 and had an overflowing lingerie drawer. I also owned several nightgowns and short nighties, and always slept in one of them. I had a dress, bra, wig, etc, but tried going out dressed a couple times, and wasn't willing to get the facial and vocal chord adjustments I would require if I wanted to have even a prayer of "passing". I also have tanned in a bikini bottom since I was in my early twenties, I like my girly tanlines. I had a couple pairs of Levi's casual fit ladies jeans prior to discovering other CDs on internet, but that was also very convenient because they fit me better than their male counterpart. I like being a guy, and have clearly defined feminine leanings, as well. I'm not willing to give up the male side of me by allowing my female side to be exposed, and I realize the genie can never go back in the bottle once she's out.
Since discovering the online world of crossdressing, I have purged nearly all my male clothing, and spend nearly every wardrobe moment trying to push the envelope as far as I can without accidentally exposing myself to family and friends.
I think the internet has been an enormous factor for me, there is a certain "dare" factor which seems to exist, and it always seems like there are always at least a few trying to push others to go further. I also find myself having more difficulty exercising good common sense at times, and have to constantly remind myself that the "real world" can be very real.