2018 – Portland, OR.
Recently there was an incident. Silly. Ridiculous really.
I was parking my car, and it was just another day. I’d looked for a parking spot, and as I was slowly backing into a space another car came up rapidly behind me. I stopped, thinking the driver might slam into me.
The oncoming car screeched to a halt and I waited. Best just to see what this driver wanted to do. I didn’t have to wait long as the driver started blowing on their horn.
I was tired. I decided to just wait it out, and with a squealing of tires, the SUV pulled out and over took me. I pulled a face as the driver passed, and taking offence the driver swung right and clipped the front of my new car.
I felt a wave of rage rush over me. The other driver pulled over to the roadside as I opened the door and got out to inspect the damage. It was superficial but with the heat of a wave of anger I stormed over to the other car.
Time slowed and I remember the smell hanging in the air. The squealing of the tires had shredded the rubber and it stank. I knew that smell. I shivered at the thought.
The door of the SUV opened and a woman stepped out.
“What the fuck is wrong with you,” I shouted at her. She stood maybe five foot two and a hundred and ten pounds. “Driving like that you’re going to kill someone!” I shouted.
I was overcome with anger and this little squirt of a woman started squeaking about how I shouldn’t have made a face at her. A rage was boiling within me. She looked like a trust fund kid, whose daddy had bought her the SUV. I doubted she’d ever done a days work in her life.
I couldn’t hear what she was saying. Her mouth was moving but I heard nothing. Blood was rushing through my head, and I could hear it like a power hose. All it would take would be a choke hold and a sharp twist and her neck would break under her own weight. Really, it is that easy if you know what you’re doing.
I turned and walked back to my car, my heart racing. I’d had my moment of anger at her. I sat in the car and took a few deep breaths. Someone on the sidewalk was looking at me, and I thought I must be a bit of a sight. I felt so angry and knew I could crack at any moment.
I calmed myself down as best I could and drove on, just wanting to be away from this situation. There was no real damage. I knew I was over reacting, it was just a stupid woman and she’d got me at the wrong moment. The anger within me seemed to boil and froth and look for a place to find focus.
I pulled over to the side of the road and looked and my hands shaking. I could taste the burned rubber smell in my mouth and feel sweat pouring down my back.
“For god’s sake,” I said to myself. “What the hell is wrong with you!”
I waited for a few minutes. I couldn’t drive home like this.
I walked about for a bit and then returned to the car, feeling terribly unsettled. At a complete loss, and feeling ashamed that I was so easily set off I drove aimlessly for a few minutes, then I drove slowly to Shannon, and feeling like a fool I fell into her arms. She didn’t notice, but I was sobbing like a child with my face buried in her shoulder.
How is it that a man can be transformed into such a child? What the hell was wrong with me?
Shannon held me and said a few things, I don’t even remember what. I didn’t tell her about the incident, it just all seemed so foolish and after a while I found myself cooling down, and just feeling the calm of being held in her arms.
And suddenly it was ok. It was just fine.
I started crossdressing regularly shortly after the end of my second marriage. It wasn’t anything particularly dramatic, just the occasional desire to wear something a little different. My mother had died not so long before, and I was increasingly alone in my life. Something drew me to the idea of it one day, and there I was in Walmart buying some panties. I was travelling for work, no longer in the press field, and was staying in a nice anonymous hotel, and so slipping into first some panties and later nylons just felt comfortable and a little exciting.
I remember thinking how it was hard to buy those first panties. Evidently I was a lot more worried about it than the checkout girl. When I got back to the hotel I just slipped into them and sat around feeling relaxed. It was just calming. After I’d dressed I often felt quite ashamed of myself. What would my father say? If I turned up in drag to the house he’d probably drop dead with a heart attack. It could be the perfect crime.
I explored the idea of shame and tried to understand it. Why should something that felt so liberating, make me feel so shameful? It was a puzzle that I couldn’t see through for years.
I wondered if it meant I was gay, but quickly got past that. I tend to think we’re all bisexual to some degree anyway. I can only say my thoughts, I really don’t know the answers, so I wouldn’t want anyone reading this to feel judged – that’s really not my intent. It just felt nice to pull on some silky panties and try to stand in heels. I thought about it later, and gradually began joining the dots together. It felt good to let the feminine side of me have an outlet. Why shouldn’t I?
I live in a liberal west coast city. If I want I can drink a beer in a gay bar, or hang out on a patio somewhere wearing anything I want, and no one is going to be that bothered. All these things I know at a rational level, and yet, there’s a resistance within. Where does that come from?
It comes from those tools I was given with which to go out and make my way in the world. I grew up in a conservative environment in which ‘sex’ or even ‘gender’ were terms that were not really discussed. It wasn’t that they were actually taboo, but they were shameful. This wasn’t a religious thing, it was a societal thing in the social setting from which I grew.
Any discussion of ‘gays’ or ‘queers’ was accompanied by phrases like, “bloody shirt lifters”, or “pooftas” or, and I still don’t quite get this one, “Damned foreigners!” Of course, after years in the media I pretty soon learned that with most of our most upstanding English pillars of society one need only scratch a little under the surface and you’ll find an entire warehouse full of skeletons in their wardrobes.
What I felt as I began to explore crossdressing was something that just helped me feel a little more feminine, which was a part of myself that had not been allowed to find a place or express itself. I enjoyed this feeling of liberation. I certainly wasn’t going to be flouncing around like an over fat turkey on a trampoline, but I was enjoying allowing myself a few freedoms to imagine what it might be like to be more liberal with my clothes, my opinions and my friendships.
Over time I experimented with some sexual adventures which pushed my limits. Some were a little fun, and some were stomach turning mistakes I wish I’d never made – but then isn’t that just part of growing as a person. Try anything once, people say. Sometimes once is more than enough.
I remember answering a Craigslist ad to meet a couple. They were probably the most repulsive people I’ve ever met. I can respect a blood crazed killer, at least he has conviction. Who knows, he may even be killing someone because he feels it’s the right thing to do. But these people, they were scum, trying to fill a void in their life with some facsimile of affection. What they succeeded in doing was nothing less than passing their misguided desires in my direction. Once again, this was just my own experience and I fully understand that some people do find some fulfillment in these dark recesses.
Our liaison was in a cheap studio apartment in the worst part of town, and somehow I’d got swept up in an online exchange, which led to an invitation, and the idea of it seemed fun. The reality of it was revolting. The two people were repellent sad individuals, they smoked crystal meth which wasn’t exactly a good sign, and wanted a third to spice things up. I think if they’d found a coyote it would have been more fitting.
I left having gone through the motions, and sat in a shower for two hours feeling wretched and swearing never to do anything like that again. Of course, it did happen again with others. More than once. Was this some form of self loathing? I was searching for something, but I certainly wasn’t finding it. And how did crossdressing fit in this picture? I’d be the first to say I was horribly confused.
I found the cheap hookups generally disgusting, and demeaning. I know not everyone experiences this. I really don’t mean to sound too judgemental about this, it was just the way I felt. I never really associated those exercises with crossdressing, though I sometimes made a vague link. I did enjoy one person’s company, who was transgendered. If I learned anything it was that even in that cesspool of disappointment there was something to be found, if one looked deep. But it was never really compelling and I soon abandoned it as a waste of time. The only reason that shameful period in my life finds its way into these pages is that you will see later, it is very relevant.
I found that my dressing was better nurtured in a caring environment. I also began to find that this was clearly not a side of myself I could share with everyone. I learned I would have some friends with whom I’d share this, and others who simply didn’t need to know about it. Perhaps I wasn’t ready to share it, but in many cases they weren’t ready to understand this part of who I am. Over a period I got used to this idea. As new friends came into my life, I might drop some hint, and watch for their interest to be reflected in some look of curiosity. I learned to discretely open that door and see if they’d walk through it.
I became surprised by who was interested in crossdressing. My first and most reassuring realisation was that many women are interested in it. To share in a crossdresser’s journey was something many found intriguing, and sexually exciting. Doubtless many men get sexually turned on dressing (which I suspect gets translated into some behaviour they later come to regret), but a very significant proportion of women, if approached in the right way, are not only curious, they are positively turned on by the idea.
I’ll explain that, but please remember this is just my experience and is not meant with any sense of negative judgement. I found that far from being turned off by the idea, many women find that crossdressing is a celebration of who they are. It is an absolute case of imitation being the sincerest form of flattery. Some women also enjoy the feeling of being empowered, as the man releases control to their crossdressing partner. The woman has complete control in many cases. She leads the way. It’s not something they need to feel humiliated by, though that in itself can be sexually exciting. Both sides of the equation can enjoy it, if that’s who they are. Either way, I soon learned that far from being difficult there were several women in my life who found the process interesting, and some who found the same enthusiasm for it that I began to develop.
It didn’t take much to translate this interest into participation. I was always sincere and I approached it with a sense of fun and honesty. By chance, I had fallen into quite a healthy way of enjoying my crossdressing. It was based on trust, kindness, honesty and respect.
I remember sitting on the beach and looking at the Pacific, while walking my dog, thinking, how I wish I’d met Shannon earlier. How I wish she’d been there to guide me. I understand now that, even if that had been the case, I probably wouldn’t have been ready for what happened. The way things were to unfold, the universe delivered to me exactly what I needed at the moment I needed it.
As I dressed more, used a little makeup, and gradually found my feminine self developing I increasingly found it a source of joy rather than shame. I accepted that I was a little out of the ordinary, and even as my third marriage started I found myself treasuring this side of myself as something very separate from my general daily life, but equally important to me. I chose not to be very vocal or demonstrative about it, being at heart a shy person.
When Shannon came into my life, I found someone with whom I could dive into this pool and immerse myself without shame in an exciting and healthy way. A committed lesbian, she enjoyed the joy she saw in me – and also found her own pleasure in our trysts. While these started a little casually, the trust that we shared and a natural emotional compatibility quickly drew us to each other. Shannon once wrote that this is a source of joy and we return to the wives for other joys and other parts of our life. Even though she was ten years my junior Shannon understood so much more than I.
As we grew closer I learned more. I cared more, and slowly began to realise that some of those tools I’d been given to forge my way in the world were hopelessly redundant. I’d been raised to believe in marriage, fidelity and till death do we part. Two marriages down the road you’d think I’d have seen through that. I’m not always a quick learner. I didn’t really give it a lot of thought, caught up in the joy of our polyamorous lifestyle. Why should I try to understand it. It felt wonderful.
Ironically, the joy of my crossdressing, and releasing the feminine side of myself at work, in my writing and even in the bedroom, seemed to contribute to my wife being satisfied and happy. I felt that dressing really was making me a better person at every level. And I had Shannon to thank for it. How kind she’d been, leading me into this new world and guiding me. I wouldn’t go as far as to use the word ‘love’ to describe this stage of our connection, but at that time I felt a deep affection for my lesbian teacher. And her ‘lesbian’ status was definitely shifting a little.
I felt like we were strands in the same piece of rope. Twined and spliced together we wrapped ourselves together creating something strong and powerful. The honesty of the intimacy was something I don’t think I’d felt with anyone before. Sharing this vulnerable part of my life so freely was something completely unfamiliar to me.
As my dressing graduated from the squalid explorations of Craigslist, into something which made me feel wonderful, I began to revisit the idea of shame. It soon dawned on me that as a child I’d left that English Country Garden of values and beliefs that seemed so important, and set out into a world in which they were not only redundant, they were positively self destructive. My challenge was not with dressing, it was with the tools I’d been given to cope with life. They were entirely inadequate to cope with the question of gender fluidity, or even the idea of self expression in alternative dressing styles. In short, I thought I’d had a parachute, but when I opened that pack up all that was in there was a sheet.
This realisation was quite dramatic. I remember at the time describing it to a friend as though, had I been a tightrope walker, I’d somehow learned that all those times I’d thought there was a safety net there had not been one at all. To be quite honest it made my blood run cold.
Yet, through this entire period I felt a growing love with Shannon, and my safety net was there. I felt my world was beginning to make sense. And so it was that, as my dressing moved forward I began to experience greater confidence. It went far beyond ‘dressing’. This was about me growing as a person. I was connecting with my feminine self – a better self. I was becoming increasingly self assured.
My development left me feeling stronger, happier and more fulfilled. All of which meant that I was entirely unprepared for the events that were about to unfold and take me entirely by surprise.
Please comment before moving on to Part 3 HERE.