Oh gosh, as a life long cross-dresser I have asked / agonized over this, over and over again. I've hated myself for it, rationalized it, loved it. Like so many others, I've been through the buy/ purge cycle many many times. Since I am in the closet still, and live with a sister who does not know, I have to hide everything. Once again my stashes are full and overflowing. What to do? What to do? In many ways it is an addiction.
But WHY do I do it? For me I think it started as envy of my sisters. I wanted to have the pretty things they had. There was the thrill of the "Taboo" when I first put on a shorts and top set a cousin staying with us left in the bathroom. It was exciting and deliciously forbidden. At this point I was too young for the sexual thrill. But yes several years later I was enthralled with the physical sensations of the clothes. I loved the feel of the materials, the feel of the fit, that strangeness of a bra around my chest, freedom of a skirt, the naughtiness of nothing between my panties and the air, I had an easy source of female garments to experience with four sisters. Then too, that sexual aspect started to come into play. Now I had another form of gratification to re-enforce my behavior. I believe it was somewhere around this time that the guilt started too and the feeling that I was perverted/sick. I felt wonderful when dress. It was exciting!, for a short time, then I'd feel disgusted with myself. The teen years were difficult times. I slowly came to accept it as a fetish, something I needed to do though still not quite right or accepted. I can't say how many times I promised myself "This is the last time"! I lied.
Fast forward to enlisting in the navy and getting married. Both put a huge damper on my dressing but I found infrequent small ways to indulge. I finally came out to my wife and though she didn't like it, I was allowed to indulge to a point. The illicit sexual side of it had diminished but was not gone altogether. By this time the clothes were not enough. I had added makeup and jewelry and a wig. Many a morning I would dress totally, dress nicely for work but then I would reluctantly change back and go to work. Many times late because of it. I couldn't always get fully en femme, but when I could, I was in heaven. I felt at peace, a calmness descended over me. The stress of work, being a husband, a father, a "man" melted away. I was a woman and it was right.
Skip forward 20 or so years alcoholism, divorced, ex-wife outing me to my boss and friends, loss of job, thoughts of suicide, living where I could, sometimes with relatives, sometimes in my car. Yet always finding ways to dress. Always that feeling of relief from my problems. Skip forward another twenty years. Things settle down, employment, stable housing, a DUII, no more drugs or alcohol, quit smoking, no more thoughts of doing myself in. Life is better the one constant is crossdressing. Still with the comfort it brings.
Forward a few more years. cancer, job loss, infrequent employment. Life goes on. Return of cancer puts me on disability, I get on VA medical, Life is good again. I continue to crossdress but I start to realize it could be better. The feeling of serenity it gives could be improved. I could be a woman.
It's not just the clothes anymore and it hasn't been for a good while. It's the life, the body, the emotions of a woman I want. I've started that ball rolling.
Why do I crossdress? Because it's me.
Jeanette