I wrote this a few years ago for my blog - now working on revising, adding, and slowly updating. A conservation last night triggered a number of memories and also left me with nightmares and insomnia around past experiences related to dressing. So I’m trying to "write it off" by going through my memory. So, sorry if this is long - I write hoping others can take something from it, but I write for myself mostly.
The first urge to dress that I can recall was when I was around 3 or 4 years old. My cousin had come over to our house after church. She was wearing her church clothes - a Sunday dress and tights - but also including a pair of Mary Jane shoes. I really wanted to try those on, but knew better than to say anything to her or anyone else.
Then I can remember being around five. I was a huge He-Man fan (one of the banes of my existence is that outside of Amanda, I was/am always pretty much a boy's boy - interested in typical guy things, played sports, liked to bird hunt, like using power tools and chains saws, like beer in a non-Brett Kavanaugh kind of way, etc.) and was going to dress as him for Halloween. My mother was worried about me being cold and so got me some tights to wear under the shorts. I tried them on as soon as I got home. Strange feelings of what I now realize was being turned on went through me coupled with disgust and shame for feeling that way and being so curious about it. Turns out it was warm that Halloween and I didn't need them. I kept seeing them in my dresser drawer but never wore them again. One day my mom cleaned out my clothes and they were gone, though I did get to wear tights a year or two later for a production of The Nutcracker I was in where I played one of the mice.
Then around third grade one of my friends dressed up as a joke. I felt really funny and awkward and knew I wanted to be dressed up too. I used to lie in bed and imagine myself dressing before I went to sleep quite often. In fifth grade, after another friend dressed as a joke, and those same feelings arose again. While both of these were big jokes, I found both of these situations highly uncomfortable - knowing that I wanted to be the one dressed and knowing that wasn’t “right.”
Nevertheless, in fifth grade, the curiosity got the better of me. I started to try on my sister's stuff (she was younger than me and small, but she had some hand me down clothes that were way too big for her and I could squeeze into a few of those things). The two things I remember initially trying on were a cowgirl skirt and a leotard initially. I loved the leotard especially. I’ve always had a fascination with the ballet and ballerinas. I of course didn’t share any of this with anyone.
But I quickly moved on to my mom’s things. She had this light pink knee length sleeveless dress with white polka dots that I would wear with white hose and either white heels (her only pair I found decently high) or Sam & Libby ballet flats (that was the early 1990s - an era when heels were out). I’d look at myself in the mirror, dance around, and rub my legs together before changing back. I continued to do this for a couple of years whenever I was at home alone - not knowing why I was doing it, but "knowing" (at least at the time that's what I thought) that it was wrong, shameful, and I was going to go to hell if I didn't stop. This was partially my own insecurities and partially my surroundings: I grew up in the stereotypical small, southern, socially conservative and religious town where being gay was scandalous, let alone a boy who liked to wear dresses. But despite these feelings, I also couldn't stop - I was drawn in, attracted by those things and the feelings they gave me.
My pre-pubescent dressing nirvana came in the summer after sixth grade and it ironically did not involve female garments. I was in a play (actually in the role of the father), and we all had to get stage makeup. There was an older girl going into ninth grade who I had a HUGE crush on who was part of the production. She did my stage makeup for the show. And because she didn’t know anything, she basically made me up like you’d make up a woman (at least I thought so at the time). Talk about doing everything you could to control yourself!
With the onset of middle school came the onset of puberty. I didn’t know anything about sex other than the concept, but the dressing sessions became more frequent. And all that of course led to my first sexual experience. I didn’t even know what an ejaculation was at the time. I had another dressing sessions. I had on one of my mom’s (thankfully) old black and white dresses, a flowing dress that was calf length with gold buttons), a pair of sling back heels, and white pantyhose. I had seen this sitcom with this ditzy hot girl who was told not to rustle her pantyhose around guys because they would think she was coming on to them. I was lying on my back on my bed, replaying the scene and I started rubbing my hosed legs together - back and forth like pedaling a bicycle - while thinking about that. The friction and tubing of the hose between my legs caused a huge ejaculation that made a massive mess everywhere, ruined the dress and hose, got all over the carpet, everything. I had no idea what I’d done initially - thought I’d peed everywhere. Then finally figured it out. created a ton of shame and “Jesus guilt.” Not to mention I had to hide the dress and hose and hope my mom never mentioned them. Thankfully, I had an attic behind my room to hide them. And she never mentioned them - to me anyway.
Anyway, I’d figure out ways to be at home alone and raid my mother’s wardrobe. I tried on the vast majority of her things at one point or another - dresses, skirts, blouses, heels, hose, panties, bras, swimsuits, and lingerie. The only things that I avoided were the more casual things - the jeans and lounging around the house stuff. I guess it wasn’t feminine enough in my mind. I’d imagine that I was the girl. I even remember drawing up fake pageant with evening gown, swimsuit, and talent competition - with me being each one of the contestants and wearing certain items from my mom’s wardrobe that I had planned out. When I wasn’t dressing and was home alone, I’d look for shows or movies with crossdressing involved. I’d scan the TV Guide on Sunday to see what was coming on. And if I was at school and could get away with it, I’d try to tape them to watch at some future point. I’d look for talk shows if there was some topic related to drag or cross dressing. I’d stay up late, hoping my parents went to bed early, and watch the Kids in the Hall and The Howard Stern Show in case there was some crossdressing. And if I was home alone there was nothing on while I was dressed, I’d find some show or movie where the women were dressed up in pretty dresses and heels. I especially found that the old black and white 1940s movies on AMC were always full of attractive, classy looking women who always wore dresses and heels. I had absolutely no interest in the plot and couldn’t tell you one thing about them, but I loved them.
All of this stunted me socially, as I had more interest in these things than building up a good group of friends and I was already feeling highly insecure and awkward just from being in those middle school years in general. And I’d come back to dressing and… do what teenage boys do when they are alone. And I’d feel terrible about immediately afterwards and change - there was intense shame, guilt, and loathing of myself.
And I was worried about the longer term implications too. I was worried that the ONLY way I'd ever be able to ejaculate was wearing female clothes. What would that mean for my future? How would I have a family and be "normal" like was the expectation of a kid growing up in a respected family in a small town? I tried not to think about those things too much, hoping that somehow I'd get this out of me and it would all work itself out. Of course, it wasn't that easy, but I also had to look at myself in the mirror every morning. But all this scared me even more - it kept me away from chasing girls and weighed on my self-esteem, which was already low from the typical insecurities of puberty and middle school.
During this time was when I first set up very rigid boundaries between Amanda and my male side. I tried to be as “normal” as possible outwardly to people who knew despite my shyness around girls and social awkwardness. And frankly I enjoyed a lot of it. I was a huge sports fan (still am), started hunting with my Dad and friends, rode my bike all over town, got dirty and sweaty - and I love all of that. I knew that the dressing (there was no “Amanda” at that point) didn’t fit in with any of that, and I just sort of lived the rest of my life, hoping that part of me would go away eventually. Of course, over 30 years later, that hasn’t happened.
Part 2 coming soon: The Internet (or AOL) starts to become a thing and I discover a whole new world…
