So let’s pick up kind of where we left off, but maybe a little more detail about the “quiet years” between high school and the end of grad school first.
Living vicariously through the Internet is tough on your psyche. You spend your time alone surfing the web (on a Netscape browser back then), hoping people have updated their Geocities page or Above and Beyond or Prettiest of the Pretty has new profile pic or (later on) Flickr and Yahoo Groups had new content. Or Fictionmania had new stories. Ah, Fictionmania - I spent so much time reading those stories, putting myself in those situations. Then you do… things… and you feel shame and guilt afterwards. And because you do those things, you don’t really have a lot of sexual energy as you go out in the real world. And again, you’re dealing with the guilt and shame. And God knows you don’t want to start having questions about what this all means for you, your sexuality, your identity, your future, all your anxieties. So what do you do? You avoid them at all costs. And how do you do that? I went back to my crutches that started in high school. Essentially, everytime I was out socially, I drank. A lot. Often heavily and often to excess. Alcohol was truly the lubricant for all of this for me that helped me feel “normal” and avoid the hard questions. I quickly found that for that period that you’re drunk, you are relaxed and you aren’t asking those hard questions. And the next day, your problems are more immediate (a pounding headache and the other issues associated with a hangover), so you’re not asking those questions then either. Sure, there is a social stigma with drinking too much, but I wasn’t generally a sloppy drunk and most of the time I was a fun drunk. And anyway, your friends (or my “friends” anyway) aren’t going to tell you you should cut back when you’re a fun drunk and kind of lame sober. And it’s a helluva lot easier to have a social stigma as someone who drinks too much while they are out as opposed to being a… crossdresser. At least that’s how I felt at the time.
And when I wasn’t drinking or online, I distracted myself by making sure I was doing well academically so that I could get ahead in my career. I’ve always been a “Type A,” achievement oriented, perfectionist, people-pleasing person. I felt that if I was somewhat gifted with book smarts, I owed it to everyone - my family, the people around me, and myself, hell the world, to apply those things and have a good career and make a whole bunch of money. I wasn’t really sure what that career would be, but I figured business would make the most sense if I wanted to be really successful - which I defined by making money. So I focused on that. That was my life - surfing crossdressing sites when alone, drinking when out socially, and focused on career goals otherwise. And then going to the gym and exercising - mostly lifting weights. Because then I’d be stronger and more muscular and my small size, which works so well for Amanda, wouldn’t be a thing. Greater confidence in my masculinity.
And somehow from this, I wasn’t going to find a wife, have a family and… everything would be fine. I’d be happy because I’d have what I’d told myself I wanted. Even though I’d been unhappy through much of high school, college, and after (I can recall the specific short periods in life when I felt happy during this time - they were that rate). And the dressing thing would just sort of go away and I’d have a “normal” life in a house in the suburbs. I didn’t think about how. Maybe I just believe it would be magic. More likely, I didn’t want to think about. Too many uncomfortable questions.
But of course dressing kept calling. That damn internet was always there, tempting me. And every so often, when a roommate was out of town or in certain periods that I didn’t have roommates, it would get too much. I’d figure out a way to dress. Sometimes that was going to the mall and buying clothes. But sometimes it was (shamefully and now very regretfully) wearing the clothes of a female roommate (I had a couple over the years) or even the girlfriend of a friend when I was lucky enough to have a little time alone at their place. I’d have a day or night or a few hours or whatever and I’d dress - no makeup, no wig - just the clothes. The arousal was sky high. And then the guilt and shame would overcome that like a tidal wave. And ultimately, the clothes would be returned (for as bad as this was, I am thankful to say I never stole anything from anyone) or purged. But not without a fight with myself first. It was always the same internal discussion. “Maybe just a little longer - maybe one more time. No one will know. You know you want too. Be good for a few days afterwards and you’ll get back square with God and eventually this will go away.”
And so often, I’d cave and the dressing urge would win. After family had visited and I hadn’t been able to be online for a few days. On a business trip when I had quiet nights. I remember one night back in around 2003, which I think was my last purge for the reason of "I'm never going to do this again". I was living alone and had dressed in clothes I’d purchased, done exactly the things I’d done in the past when I’d wear my mom’s clothes, surfed the Internet and felt extraordinary shame afterwards. And thinking I’d gotten it out of my system, I threw the clothes in the dumpster at my apartment and went out to meet some work colleagues to chase women on a Saturday night. The night turned out to be a huge dud, and we all went home early without much drinking. I get back to my apartment and felt those the clothes cry out to me. I literally end up standing in the dumpster finding and retrieving those clothes to repeat the exact same thing I’d done earlier that night with the exact same outcome and the exact same shame. The clothes ended up back in the dumpster and the next day garbage truck got them. If it hadn’t, I may have very well repeated the same thing again.
That same cycle repeated itself. Again and again. Avoiding the questions. Trying to focus my mind on other things - anything to not ask the questions. No questions. No, no, no. It will all work out. Just don’t ask the questions.
Fast forward a couple of years. I had gone back to grad school for a business degree to change the path of my career and advance it in into a more lucrative field (again focused on money). After a couple of years of starving dressing because of roommates (male this time), I was finally on my own. In a new location. Away from the small town. Away from everyone I knew. Working in the big city. At this point I was in my late 20s. And I decided that I’d better figure out a way to settle down. Not having the guts to approach someone in a bar or socially, I figured I’d try online dating. But at the same time, for the first time in a long time, I had the opportunity and the money to build a bit of a wardrobe. And maybe I started to recognize the cycle I was in. I basically said to myself, "Even though I feel guilt and shame, and I will continue, these episodes happen too often to keep doing this and I finally have the opportunity to do it. I’ll get it out of my system and be done. But I’m not going to throw the clothes away. I’m going to stop being a lurker and build an online presence.” And with that decision in the early fall of 2006, “Amanda” was born.
I chose the handle amandaill out of pure paranoia. In hindsight, it was a horrible name - was I calling myself or Amanda - ill (as in mentally ill) for existing? Subconsciously, maybe I was. But the “ill” is actually short for Illinois. It came from this line of thought: Let’s see, I’ll make up an entire existence for Amanda that is as far from the truth as possible so no one will ever know. I’m from a suburb of Chicago - I chose Lake Forest for whatever reason. I went to the University of Illinois. Then I went to grad school at Northwestern down the road from Lake Forest. Absolutely none of this was true. But such was my level of paranoia. With that, I created the handle amandaill and it’s stuck ever since.
And the name “Amanda Marks?” Well Amanda was the name of the first girl I had a big crush on. She was a southern belle I had met a church camp years before. I knew her for a week, we exchanged a couple of letters, and I never saw her again. Helping matters was that I didn’t know a lot of Amanda’s, so I felt less creepy - like I wasn’t emulating someone I knew. And the Marks came from Mimi Marks, an absolutely gorgeous trans performer who performed at the Baton Show in Chicago (of course) and who I had only seen on talk shows. So there you go. Several years later I added “Catherine” as a middle name because it sounds classic and sort of fits my persona.
So that’s how Amanda was born. But back to the story. While I continued to lurk online, to dress some, and I tried to date. I really leaned into that. Lots of first dates, occasional seconds, and not a lot after that. There just never seemed to be a spark. I was self-conscious, I was awkward, and I was only relaxed on those dates when I drank (that’s usually the times there was a second or third date). It just wasn’t working. And I was starting to panic - my grand plan to be “normal” was starting to show holes. My parents were starting to put the pressure on me - “you’re almost 30 and you’ve had one girlfriend and that was in high school. When are you going to get married?” I really felt the pressure coming down on me.
It was at that point a funny thing happened. I was literally ready to give up on dating. I actually had a conversation with God - in those days I still did that. I said something to the effect of, “you’re not helping me with dating and finding a wife, so I’m going to lean into dressing. I experimented with shaving small parts of my body to see what it was like. I started poking around online - that’s the first time I ran across dressing services like Genderfun and Femmefever and TGNorth. And I was ready to give up. And then… I heard from an old classmate I somewhat knew in high school. She had reached out to me online for a random reason. That grew into a conversation and she began to pursue me. That conversation grew into more conversations and then a meetings when I’d return home. And so we began a long distance relationship.
This was great for me but ultimately gave me a false sense of confidence about dressing. I finally had a girlfriend. She was (and is) a genuinely good person and someone I genuinely cared for - and as our relationship grew, someone I loved. And the long distance relationship gave me time to get the dressing out of my system in between visits. Then during visits I could be entirely focused on her. On us. And I was. Our relationship went on for a while like this. It was great. But again, that meant it was going on with me not asking questions about Amanda and me certainly not telling her about it. And why would I? When I was with her I didn’t think about dressing, I was finally going to get personal piece I needed to achieve that “normal” life I was looking for, I’d finally found a great relationship with someone I loved and who loved me, and anyway, dressing was going to go away as we spent more time together. So why did it matter? Why would I tell? Why deal with that difficulty and potentially blow it all up? So I didn’t. And when I look back on everything in my life, all the secrecy and hiding and shame and beating myself up over the years about dressing, and everything else I’ve done in my life outside of stuff around dressing that I’m not proud of, that decision, the one that made then to not make a decision, is the one thing I beat myself up over. That would have been the hardest thing to do - maybe next to telling my parents - but I wish I had been honest about it. Maybe I was avoiding conflict. Maybe I was being naive or just too much in denial from not looking inward for so long. But I didn’t give her the credit I should have. I didn’t have the confidence in myself or in her love for me. And I was still avoiding the hard questions. Just like I always had.
Eventually, the long distance relationship ended when we got married. And with the long distance relationship now an everyday relationship, that time I had for Amanda was no longer there. The ending of the long distance part of our relationship when she moved in was my first purge for a different reason. It wasn’t a traditional purge of shame for dressing. It was a purge because there was no where for Amanda - and because I had the life I wanted and there was no need for Amanda in my mind. I threw those clothes away thinking that Amanda was being thrown away with them. Of course, that was wrong. Very wrong.
Over the next few years, we settled into life. Had a couple of kids. Bought a house in the suburbs. And much to my chagrin, Amanda was lurking there the whole time. Stealing time late at night or early in the morning or on the commute to work. She wasn’t going away. She was growing louder. The more I avoided expressing her, the more insistent she became on being expressed. In rare moments such as overnight trips for work, I’d buy clothes, dress and purge. Dress and purge. Because I had to get it out of my system. And purging for the same reason - to keep the secret, not because of the shame. It was exhausting.
And importantly, I was growing tired on a bigger scale. Tired of the constant battle within myself. I’d been fighting first dressing and then “Amanda” for years - decades. And she still hadn’t gone away, despite all my plans. It wasn’t fair, it wasn’t right that I had been cursed with this. I hated it. Hated who I was. Still used the alcohol to hide it. But I couldn’t fight it anymore. There was only one option - acceptance. Amanda wins. Fine, you get to exist. I don’t have to like you that you exist, but you get to exist.
So one summer - I believe in 2014 - my wife and the kids were going to take a longer trip over two weekends while I had to stay home and work. This was a chance to go hog wild with Amanda. To finally express her for a few days, not a stolen moment here or there or talking online. And maybe, just maybe, I could actually see her in all her glory. Wig and makeup in addition to clothes. This was going to be my acceptance.
But a funny thing happened. The stars didn’t align initially and then I chickened out, reverting to my old beliefs. I had reached out a dressing service in NYC called Genderfun - some of you may remember it. But they couldn’t schedule me that first weekend. So I had a bunch of Amanda time at home. I spent most of that weekend dressed. I got a wig and tried makeup myself. And I looked… terrible. Like a clown. And after those days of dressing, I felt like I had gotten Amanda out of my system again, and I looked bad anyway. So I didn’t follow up on that next weekend to schedule the session with Genderfun. And when the trip ended and my family returned, one last time, I purged those clothes I’d bought. One last gasp in the fight against Amanda. I hadn’t fully jumped to acceptance yet.
Of course, after that trip ended and Amanda wasn’t able to be expressed, I realized I’d again made a mistake. The same mistake I’d made time and time again - I had repressed that part of me. Repressed Amanda. I realized I couldn’t do that again. Amanda had to be seen. That was when surrender, which was categorically acceptance, finally happened.
It wasn’t until the next year when another similar trip happened that Amanda was finally seen in all her glory. That the decision to surrender had an impact. And it wasn’t with Genderfun. It ended up being with Femmefever. But that’s where we’ll pick up with Part 4…
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