Why I continued

From that first time in which I can clearly remember voluntarily putting on a girl’s garment (and very non-neutral underwear at that), I was “hooked”.  While I was still pre-pubescent, the look of such clothing was arousing to me.  And, of course, the look of them on my body was more arousing than when they were just a cloth on the floor.  This is similar to the fact that catching a glimpse of a girl in her underwear is more than just seeing underwear on the rack.  That overwhelming feeling of arousal stayed with me- something had struck a chord in me and resonated with my needs and wants.  I even secretly wore that same pair to school one day in fifth grade when things were particularly difficult (people really picked on me for being poor, poorly dressed, etc.)  Later on I discovered pantyhose.  By then (middle school sexual development), dressing up led to erection.  Feeling always rejected by the girls, totally afraid of pornography (still in church), and vaguely aware that masturbation was also somehow perverted, this was my only sexual release.  Wearing pantyhose I felt closer to women and the feeling as I rubbed my legs together eventually brought the first of many such orgasms

Quickly, high heels became the prized item for me (probably since I thought they were so sexy but none of the girls in my family really wore them so I couldn’t get ahold of any), but being fully clothed (dress, underwear, makeup, polish, hose, shoes, etc.) brought the fullest satisfaction.  In the simplest times, I didn’t want to be a woman, just to have sex with one, and in a twisted way having their clothes on my body and moving around in them the right way (in effect masturbating without touching with my hand, though I eventually just did that too, though dressing up as well was most gratifying) was my way dealing with the urge.  Of course I was aware that people would find me weird if they found out and I was ashamed, but I figured it wasn’t as bad as the alternatives or that it wasn’t really bad at all since I was not involved with anyone else, just my private pleasure and curiosity.

But times were certainly not usually simple.  Not only did this habit occasionally press the limits of my moral boundaries (and even to the point of surprising and embarrassing myself with the things that would turn me on or the lengths I would go to in order to gratify myself in this way, such as stealing clothes from women or stores), but even my day-to-day experience with this (and at certain points where I had my own room and a stash of clothes, it got to be a multiple episode per day issue) was varied as to what exactly was motivating me at any given moment.  It was like it took on a life of its own- almost as if there truly was another person (the “female me”) taking up residence in my life!  As I got into college and began turning my life back toward righteous and moral living, I tried to sort all this out, very much feeling like a was up against a puzzle too complicated to solve.  It has taken the last couple years of serious sobriety to really distill my thoughts and feelings into the following categories.  Each one goes into greater detail regarding the big question of “why” I continued this crossdressing lifestyle:

Closeness

Perks

Conditioning

Suppression