As a young boy my eldest sister was often complaining about my long thick eyelashes and my tight rear. She lamented the fact that I was endowed with the feminine features that she longed for. Both of my sisters were pressed in watching after me in the summer since our parents both worked. Taken along on shopping trips to department stores, holding handbags while they tried on outfits was part of growing up. At home I was used to zip and unzip them into their dresses, and as I grew they often asked my opinion on the clothes they were thinking of buying. Since they were older they controlled the television and I recall seeing Marlo Thomas as 
"That Girl" and hearing the wistfulness in my sister's voice as she wanted to look like her. This all seemed perfectly normal to me, even the resentment of having to go with them shopping when I wanted to play with my friends.
The dawn of my fascination with crossdressing began with TV! Watching re-runs on American TV of "The Avengers" and seeing the dashing, lovely and dynamic Mrs. Emma Peel. With her leather jumpsuits and her boots I was captivated and those were my first fantasies .. about being a spy captured by an all-female organization. The only obvious way to escape was to dress like a girl. So when the family was out, at school and work, I'd slip into my older sisters' room and play.� At 11 the dressing was non-sexual --- I didn't even stuff the bra cups!. This went on for about a year and then other things forced this fantasy world to give way to stickball, Star Trek and football.
Football for a skinny teenager [I only weighed about 110 pounds then] was not easy, though the games were only local --- urban games where different "blocks" played one another, for example 54th vs. 62nd. Still we played tackle and I had the equipment and read play books and designed plays. With all this theoretical knowledge I was made captain of the team, of course I was not as good as the more natural athletes and had to work to do well. So I practiced in my house, tackling pillows ..... Then one day I geared up but this time with a twist --- I'm still unsure why but I wore my sister's panthyhose, panties, bra and her knee-high black leather boots under my football equipment. I practiced running through the railroad rooms of our apartment and tackled (even sometimes jumped) on all the pillows in the house. Well after a few tackles I had the first ejaculation of my life ... I thought I'd urinated in my pants and was dumbstruck by all the white sticky goo.
This led to experimenting with what had happened and for almost a year every chance I had I dressed in sister's clothes ... even tried using her fall to make hair seem longer a few times ... looked really stupid on me. I always memorized the exact position of each and every piece of clothing that I used, but I still wonder if they suspected anything. My favorite outfit was a brown knee-length skirt, soft yellow blouse and brown vinyl knee-high boots. Sometimes I take a pair of panythose from the hamper and wear them to bed. Since I was the last one to leave the apartment, I often cut of school to dress-up.�
This was also the time when Ray Davies and the Kinks produced their "Lola". And then there was the Beatles singing about Jojo. Of course, once I actually read the lyrics I noticed that I had mis-heard the words.
There was a point when I was nervous that the boy next door, about five years younger than I, was rumored to be looking into our apartment watching the 'girl' get dressed.� I didn't play with make-up much, the few times I did, getting off the lipstick and eyeshadow seemed to take forever, and I still can feel the landlady's curious eye on me sometimes after I'd finished and was going out to play ball,particularly if I'd used blue eyeshadow.Mass culture also played a role in some of my confusion. The Flip Wilson Show featured Geraldine and her "What you is what you get" phrase.
Often Geraldine was wearing go-go boots which furthered my interest.Of course, I had no idea about crossdressing until I saw an article in Look magazine (yes I am THAT old) about transsexuals and I went ot the library and read the Christine Jorgensen story.
I
wondered if that was me .. but I didn't feel like a girl or want
to be one ... I just got such a tremendous sexual thrill putting
on the clothes. Then� I stumbled across Dr David Reuben's
book "Everything You Wanted To Know About Sex ...."
and discovered, according to his diagnosis, that I was a transvestite
and that, in his judgment, there was something very wrong with
me.� But there didn't seem to be anything wrong when my bought
me my first pair of bell bottoms, they were pale blue, except
that I took some kidding from my friends.� That changed within
in month when all of them were also wearing "bells".
All the dressing stopped with the advent of high school ... there was simply no time to do any dressing, with studies and running on the track team. Even a few year later when I stopped literally running and began to do all combinations of drugs and my hair grew long enough to reach my nipples ... I did not dress. All the clubs, all the opportunity ... none taken.� Even when I'd go shopping with my sister and was mistaken for a girl ... there was too much fear. Even when David Bowie hit the scene and the New York Dolls pranced around and Candy Darling
(who
I admired and longed to emulate -- though I lacked the nerve)
and the Warhol girls emerged from the photos of the Village Voice
... I did not dress until one New Years Eve.�� I was stoned and lonely and alone and so that night while the house was empty I dressed in my sister's black crepe knee-length dress with black bra, panties and pantyhose. No make-up and shoes that were two sizes two small, and a fake white rabbit fur coat was all I had on when I went out. The sensation still lingers: of cold air around my legs and the intense sexual thrill.. Stumbling (with heels and 'ludes, walking was not easy) I went all of 200 yards before I climaxed and with that release I wondered where I was going. I'd had no plan except to get on the train and go into Manhattan. But that evaporated.
For the next few years I continued to run from life and desires and finally I stopped polluting myself with drugs. The task was hard and all the 'friends' I'd had disappeared, I was alone and so I answered an advert in the Village Voice from another transvestite. I wrote basically the same story you've been reading and left my phone number. Never thinking that anything would happen .. but she called and we spoke and I was spooked. I never got back in touch with her Oliva nee Vincent. She went on to do some fabulous things for the T* community (such as the Pocono retreat weekend) and I went onto reading monthly magazines, Tania Volen's "Transvesita" was a nice little monthly.
Then years later I began to purchase my own wardrobe .. before I had always borrowed my sister's things but they were married and gone and I was working a good job and had the money. I bought a wig, under garments and all the trappings .. with 4 pairs of boots. I bought a tripod for my camera and took photos and laughed at myself. At work I began to wear panties and other undergarments. And then I meet a woman and feel in love against my better wishes ... she was married, though having some problems. Anyway she felt the same about me and my wardrobe went to the landfill.
Of course .... I know .. the relationship lasted about a year and she went back to her husband and I went back to college. For a few years nothing and then I discovered the BBSs. I joined Lifestyle I wrote some stories for them and had a ton of cyber sex.
For a while this was okay but I stopped and then I found the Internet. A whole community of people similar to me!� I found Tggallery [once known as Donna's Den] (a great chat room) and after talking to some people I began to amass a new wardrobe. I meet someone through the room and the 'real life' meeting was not what I wanted .. maybe because we meet as males .. or maybe because this person's photos were not of theirs but of someone else's ..... makes me wonder about the created personae we develop on-line ....
For a while I dressed and did my make-up but I was troubled. I had fallen in love again and was rejected out of hand and found some solace in getting dressed. But that was not enough and though I kept my legs shaved (I'm a cat. 4 bicycle racer) I tossed out all my things except for a leather skirt I sent to Rhonda who never let me know if she received it!
Now I'm back again ... maybe I should give into the feeling of wanting to look good ... of feeling sexually attractive (which I never feel as a male!) ... or whatever...
