Was there a particular depiction of crossdressing in the media that really made an impression on you early in your life -- something that really gripped you and stirred up your budding interest? Especially if you, like me, grew up long before the Internet's barrage of trans images, and only had a few fleeting insights into that world through TV, film, or print.
Three examples come to mind. I grew up in the 60's and 70's, and remember being fascinated by Flip Wilson's "Geraldine" character on his variety show. He looked quite fetching in drag, and created a very believable (and funny as hell) character. One sketch in particular wowed me -- when Geraldine became a Playboy Bunny. Being naive and as yet unacquainted with things like falsies, waist-cinchers, and the art of "tucking," I was mesmerized at just how he managed to achieve such a curvy, feminine shape.
The second was an article in Life magazine titled "The Boys in the Bank." This was about the botched bank robbery that was later dramatized in the movie "Dog Day Afternoon." Included in the article was a photo of John Wojtowicz's ("Sonny" in the movie) crossdressing gay boyfriend Ernest Aron ("Leon" in the film) en femme. That little, blurry black-and-white photo fascinated me. This issue of Life was one of several amongst a ragtag collection of magazines available for perusal in one of my high school classrooms, and I took every opportunity during down time to casually wander over and get another glimpse of that picture.
Finally, there was an episode of the old game show To Tell the Truth. The challenger was a young man who had been jokingly dressed as a woman by some of his female friends and entered in a local beauty contest as a joke....only to actually win the damn thing! Both the real subject and his two "imposters" on the panel were in full drag. I was not only drawn to how good they all looked, but by the notion that this had been done to him by girls (I always had fantasies of being dressed up by a female friend), and could actually look so convincing as to beat out real girls in a beauty contest!
