Mine is a rather simple story, and one that I am sure most of us can relate too. Starting as a young boy with an older sister and younger brother, I fondly recall my sister dressing me in some of her cloths so as to have a "play friend" during her dress-up moments. I vaguely recall that excitement, and soon found a neighboring girl of about my age who loved to play dress-up too! Mind you I was only about 8 years old at the time. I remember soft sweaters being my most sought after item of clothing and to this day that is still the truth.
Halloweens were rather fun....why my Mom would dress my brother and I as little girls was beyond my recall. But who was I to complain!!! I loved it...however I think my Dad was a bit puzzled? All the time this hidden desire was and still remains to this day to be hidden. As one can imagine, HS and college years were difficult to dress...and I recall them being rather difficult times as I struggled with what was, at that time mind you, something I failed to know little about. I was even in a Middle school "camp-town" play portraying Carol Merrill from the Lets Make a Deal. I even wore a bikini (I know...what was I thinking, but I was a competitive swimmer and had a good tan line thanks to Speedo's).
Did I WANT to be a girl? I was a boy...I dated way too many girls, but yet these simple yet strong desires to dress still plagued me . Welcome the Internet!!! There I found I was not alone!! And it was at that point I plunged head first into the world of cross dressing. I guess I went on a spending spree, and REALLY got hooked on eBay. I found some wonderful deals, some of which have unfortunately been purged. My first time out was one I will never forget, and if I could locate the TS friend I made on line who walked me through a hotel lobby, into the streets of Boston and through the door of Jacques, I would thank her with all of my heart. While frequenting Boston on many an occasion, I came across a girl on line who looked spectacular!
She told me of a local guy who worked "magic" and I just had to check it out. Well...that guy is none other than Jamie Austin, who at that time had little exposure in the Glam industry. In fact he didn't even have a studio, so many of my earliest transformations were done while in my hotel rooms.
I have been out in the past, but now my days of dressing are a bit suppressed. I guess I have retreated back as you could call me "hotel-ed" instead of closeted, as it is in hotels (I travel a bit with work) that I get my chance to kick back, relax and put on some of my various outfits, which I have chosen for style and class. I am still not out to any friends or family, and perhaps will keep it that way. I hate the deceit involved, yet I also fall into that class of girls who feel the ramifications may be disastrous.