By Amanda J.
I hate being a transvestite.
It’s strange but as I was writing that sentence – and I chose the words deliberately – I was already thinking what the reaction would be amongst those who read it. ‘Transvestite’, of course, is a word that’s fallen out of favour and these days has been replaced by the term ‘crossdresser’. Its usage still just about hangs on in certain quarters – I know of a very well known CDer on Flickr who frequently refers to herself using that term – but for the most part, its usage has died out not only amongt the CDing community but in general parlance.
And yet rightly or wrongly, the mere act of writing that simple sentence conjured up so many negative memories in my mind that I’m not surprised that the word fell out of favour. In the end, I guess we’ve gone through a rebranding and perhaps that’s no bad thing, given all the negativity I have felt about this side of me for most of my life.
Like many of us, this side of me first properly emerged when I was a teenager. I can pinpoint a few occasions previously when femininity entered my life but the turning point was finding a discarded pair of my mother’s tights and trying them on. The rest, as they say is history. Of course it felt wonderful. Of course there was an immediate reaction down below. Of course I felt insanely ashamed and guilty straight afterwards. And of course that shame and guilt soon evaporated and the whole cycle started again.
In retrospect, the shame and guilt was completely understandable. ‘Hey guys, tried on my mother’s clothes last night and got the most amazing …’ well, you get the drift but it’s hardly going to go down well with one’s peers, particularly in an era when homosexuality and everything else of that ilk was deemed fair game for endless jokes. And let’s face it, keeping quiet when everyone else is pouring scorn on people like that raises suspicion so it’s easier & safer just to join in. More shame and guilt and, worse still, reinforcement that the feelings being experienced are very wrong.
Like most boys my age, I was desperate to get a girlfriend. Whether this was because hormones were raging through my body or whether it was because of a forlorn hope that it would somehow cure me I don’t know. Probably a mixture of both. At least when I crashed and burned, which I invariably did, there was one girl I could always rely on to be there in my time of need – myself – but I was well aware that the inner girl was diverting my attention away from the very thing that would cure me.
And finally I did find a cure – Mrs A. All thoughts of indulging the inner woman (as the inner girl had become by that stage) vanished as I realised that all of those distractions I had were just a surrogate for the real thing – a beautiful wife who looked far better in those dresses and shoes than I ever could. Being a transvestite was just a chapter in my life that had drawn to a close and now I was rid of it for good, there was no need to raise it.
I’m not sure exactly when I realised that the cure had only been transitory. Perhaps it was when I opened the Sunday papers to be confronted with a photo of an attractive woman who ‘was born a man’ (what an idiotic expression that is – has a midwife ever answered the ‘what is it?’ question with ‘it’s a man’?). Or maybe it was when Mrs A first voiced her thoughts that there was something from my past that I was keeping from her. Certainly, by the time we got connected to the fledgling internet and I realised that there were places where transvestites posted photos there was no going back.
There were times when I was in a blind panic. Mrs A’s musings about what it was I was keeping from her perhaps getting a bit too close to the truth, starting to blush when nearly getting caught in the act of browsing websites or worrying that Mrs A would see the same Sunday newspaper article that I’d seen and ask the wrong questions. Quite frankly it was debilitating. But the inner woman was starting to scream louder and it was inevitable that the dam would burst and burst it did in mid-2009.
That was supposed to bring me relief but if I’d felt guilty about keeping this side of me under wraps prior to that time, it was nothing compared to the guilt I felt when I’d resumed dressing. So guilty that I tried to cure myself by purging several times; the immediate relief was palpable but I found out the hard way that it would only be a matter of time before the urges returned with a vengeance – weeks if I was lucky but more usually days or even just hours – and I then had to battle with the frustrations & anxieties before I finally succumbed & restocked only for those emotions to be replaced with guilt & shame once more.
I’ve documented what happened next on other posts here – 2013 confession, 2014 ultimatum from Mrs A to cease & desist, 2019 return to dressing (and shame & guilt) and 2023 second confession & DADT agreement from Mrs A – so no need to go over old ground.
Taking all of that into consideration, is it any wonder that I hate being a transvestite?
But here’s the funny thing. I love being a crossdresser!
Well, what’s not to love about it? The building excitement as things are laid out ready, the sensual feel of the fabrics as our bodies come into contact with them. Sitting down in front of the mirror to erase as much of ‘him’ as we can and then standing in front of the mirror, seeing ‘her’ looking back and the absolute feeling of bliss that results.
Funnily enough, though, if you look for definitions of ‘transvestite’ and ‘crossdresser’ on google, you’ll generally see something along the lines of ‘someone who dresses in the clothes usually worn by the opposite sex’ for either. But then click on ‘images’ and what you’ll see is very different. One returns images of drag artists and other of the more flamboyant elements of our community and the other a far more tasteful & respectful selection. No prizes for guessing which is which and which I feel more closely represents who I am. Perhaps we could assert that crossdressing has become the acceptable face of transvestism!
It would be easy to assert that the turning point for me happened in January this year when Mrs A agreed to a DADT arrangement and, in an instant, all of the feelings of guilt that I had hitherto experienced evaporated. Since that day, I have had the freedom to express this side of myself with impunity with the only constraint being the need for an empty house. Since then, I’ve tried hard to get something approaching acceptable makeup skills and have taken ‘Amanda’ from the depths of the closet into the real world. Deep down, though, I think the change happened much earlier than that.
Underpinning the change has, I think, been acceptance. That’s both acceptance from others and self-acceptance. Acceptance from others once seemed like an impossible dream – how was I ever going to reach the dizzy heights that those at the top of the transformational game achieved? It’s not a competition but let’s face it, the superstars in places like Flickr and here at Kandi’s Land set the bar very high. And yet far from being aloof, many of those superstars were happy to give encouragement and some even admitted to sharing exactly the same challenges that I was facing. I may have felt a bit of a fraud in their presence but they seemingly had no such reservations. And more was to come as I started sharing my thoughts on a range of issues – the forerunner of what I do here – and others were happy to share their views with me, mostly agreeing but sometimes rising to the challenge of debate. I may still have been wrestling with exactly who I was but those I encountered seemed to be happy to accept ‘Amanda’ at face value and I’m still amazed by that.
Self-acceptance was a lot harder to pull off. It’s one thing having acceptance on a place like Flickr but another thing completely to be able to shred all of the hangups and prejudices about being a transvestite. So what changed?
I think it’s fair to say that, for much of my life, it’s just been all about the clothes. The early sexual response was pleasing but soon waned and whilst I enjoyed getting dressed up, particularly when freed from the worry of an embarrassing reaction, I was never able to connect with the person in the mirror. The gulf between me, the guy, and what the person in the mirror represented just seemed too wide to be realistically bridged. Simply put, while others were able to accept ‘Amanda’, what she represented was still just a dream/fantasy as far as I was concerned.
In many respects, that’s a huge ask – to dump all of your preconceptions and accept that a part of you that has caused you so much guilt and shame for so long is an important part of who you really are, to accept that the gulf between you the guy & your feminine alter ego is not wide but actually non-existent and to embrace the fact that there’s absolutely nothing wrong with feeling more comfortable in the identity you have created than in the one you were born with.
Slowly but surely, that change in mindset did take place. Of course, getting to grips with the transformation is a prerequisite. I had professional help to show me what could be achieved and that in turn inspired me to work hard to improve my makeup skills (I use the word ‘skills’ loosely here!). Believe me, it’s an awful lot easier to accept your feminine side if she (a) doesn’t just look like your male side in a dress and (b) you have a modicum of confidence that she’ll pass muster in the outside world for anyone more than six feet away.
And with that evolution came the realisation that I was no longer just looking for the sensations of the clothes; the inner woman was now a complete entity who I looked forward to seeing and missed if she was not around for a while. But that sounds like I view her as someone I become but that couldn’t be further from the truth. ‘Amanda’ is as much a part of who I am as ‘he’ is and needs to be free in the same way. And allowing her – me – that freedom was really the final step to complete self-acceptance.
I could go on about how I want ‘Amanda’ to move away from just wearing body hugging dresses & high heels and adopt the more casual styles that women usually wear. Or how I want to experience more life through her persona. Or how I want others who know ‘him’ to understand the complete me, not just the me that they recognise at present. But all of those are consequences of self-acceptance, not necessary components of it.
But perhaps I should end with a slice of reality. I can never assert that I am a woman at heart because the simple truth is that I don’t know because I have no experience of what it’s like to be what we traditionally describe as female – someone with XX chromosomes and all of the biological and emotional differences that that brings. I can certainly look like a woman with a bit of work on my part but that’s not the same thing.
Equally, though, I can’t say what it feels like a man with any more authority than my personal experience permits. For all I know, every other man on Planet Earth may experience completely different sensations to the ones I feel. On the other hand, perhaps wanting to wear women’s clothes is something that every man experiences to some extent. We don’t know and how many men are really going to admit to it?
But what I can say is that I absolutely know what it’s like to be me. Whether the feelings I have are more closely aligned to others with XY chromosomes or to those with XX chromosomes, I have no idea but it doesn’t matter because now I know the complete me and can be proud of who I am, not feel shame or even disgust as I have done in the past.
Some may denounce me as ‘just another transvestite’ and they’re welcome to their opinion. My pronouns are whatever anyone wants them to be (within reason!). They can decide that, in my finery, I conform to society’s expectations of what a woman is and embrace me on that basis or they can decide that a man in a dress will never be anything more than a man in a dress. Because in the end, I’ve gone way beyond worrying about trivial issues like that. I’ve wasted far too much emotional energy fighting a battle I could never win and the truth is that defeat feels far better than victory ever could in that particular battle.
And that’s how I came to love being a crossdresser and, in the process, love myself.