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The loneliness of a mature crossdresser

Middle age


I married early and I thought, with some relief, that my dressing was now a kid thing from the past. Over and done with. Little did I realize that now I had the opportunity to explore my wife’s wardrobe and for a while many of her things fit me. In fact I started to buy her gifts of loose fitting clothes that I could possibly wear myself and because my Spouse never had the slightest indication of my crossdressing I was never “discovered.” The loneliness grew in direct proportion to my frequency of dressing. Unable to communicate with like minded others the secrecy grew so intense that my ever perceptive wife noticed it and commented to me how withdrawn I had become even about the most trivial of matters. I dismissed it with off hand comments that there was no great mystery of not talking about trivia and I always discussed important matters with her and made no decision without her knowledge and consent. She seemed to accept that and never brought the matter up again.

Well, I was off on a binge of dressing that with some ebbs and flows has never ceased and has grown incrementally. The more I dressed the more I wanted to dress and the more fully I wanted to dress. I now needed to put on much more than a nightie or a slip to get the sense of fulfillment I wanted and required.

I began to divert and keep for myself suitable clothes from my spouse’ donations to the Goodwill and started to purchase clothes just for me. Now my loneliness intensified because now that I fully presented as a woman I wanted some exposure to assure myself that I could carry it off as well live the giddy thrill of doing a little walking “on the wild side.” I also had to find suitable hiding places for my clothes.

The community I live in is far too small to risk going “out.” Even leaving the house in the car while dressed is something I can only do under the cover of darkness. None of the communities nearest me offered much opportunity either. I couldn’t risk doing any shopping because I frequently met people I knew while in the various malls. Besides I couldn’t leave the house dressed in the daylight, my spouse had yet to know my practice and I had no one to link up with to do things together with and I was too insecure to try anything of this nature by myself. I felt truly trapped as I struggled with a strong desire to get out and present as a woman while desperately striving to keep the whole activity under wraps. I was caught in the crosshairs of desires and discovery and I saw no outlet for expression.