Who Is That Girl? Part 1.

For starters, just a little background about me: I'm 63, an "only child" myself,  straight, retired, married for getting close to 30 years, with one grown child, and a better half who's somewhat tolerant, though occasionally I catch flak about my femininity.

When did I start dressing?  Well, that's a long story...goes back to childhood.  Because of that, "prehistoric" pictures are scarce! 

My father was a busy executive, spending every day and many evenings at work to provide well for his family, and thus didn't take much time with me. I spent my days, and most of my evenings, with my mother.  No baseball, football, hunting, fishing, etc.  Thus I never acquired a tolerance of,  or ability in, sports.  (How many kids do you know that actually failed gym class?!  And, how DO you fail gym class???  Not really sure, but I managed!)

To this day, on a scale of 1 (low) to 10 (high), my interest level in sports is somewhere around Minus 25.  I've absolutely no interest in playing or talking about sports, hunting or fishing.  And I don't drink or smoke. So, I really don't fit in well as a typical guy.

Instead, my preference is to sit and talk with the girls.  This happened a lot through life, even at work, right up to the time I retired.  Whenever I chose to sit with the girls at lunch break instead of staying at my desk to work, they included me in their discussions.  Occasionally the girls gave me suggestions (with pictures) as to what dress or skirt outfits they think would look good on me, what shoe styles and what size heels to wear with them, and pictures of different hair styles to try.  Other times they included me in their talks about dating, relationships, how to handle situations with boyfriends, and treated me just like one of the girls.  The last year or so, I wore my flats Mondays through Thursdays, and several other girls usually did, too, for solidarity.  Like these:

It was fun to wear the same type shoes as the other girls.   And on casual Fridays, often I found myself wearing the same color Capri pants and Keds as at least one other girl.  I suspect none of this did anything to further my masculine image! 

I can recall 'way back in the 1950s, when I was still too young to be left home alone, accompanying my mother to various department stores as she shopped for dresses and other finery befitting an executive's wife, and watching while she modeled her various options.  I spent far and away more time in dress and lingerie departments than any other boys my age, but having had so much practice at being there, I didn't see it as a problem - it just seemed natural.  I wasn't at all embarrassed by being around femininity, though I noticed that if any kids were present besides me, it was always little girls in dresses.  And I suspect that spending so much time around females and their clothes may have been the "seed" to cross dressing, which eventually germinated and took root. 

While I tolerated my time in dress shops, because I had to, I really hated shopping for boy's clothes.  So they always just "appeared in my closet."  I never participated in buying them...Mother just got them for me.

In the early 1960's (while having problems with other kids in school after relocating with my family) I started getting into mother's lingerie, and trying on panties, bras and stockings whenever she wasn't home.  This continued for several years, through another change in schools due to another family move. Stress-related?  Probably.  I was never caught - or at least I escaped being confronted about it.

By my senior year in high school, I had made a local switch in schools, and my social/academic situation was much improved, so experimentation with things feminine just "went away" on its own.  And once in college, I was one of many students in a big college on the west coast, so I was too busy with academia to worry about pantyhose and such...as a commuter student I had no social life whatsoever.   My first job in the early 70's provided the same backdrop.  No time for social life, though things were basically good...two jobs, two new sets of experiences...meeting new people, moving ahead, then finally, dating...as  a guy, and not in a dress!

Part Two Follows...