Close this search box.

Learning To Love Myself

Grab your coffee, it's Amanda time!

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  ‘Transvestite’, of course, is a word that’s fallen out of favour and these days has been replaced by the term ‘crossdresser’.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.


12 Responses

  1. Amanda,
    Well, what an outpouring of an individual’s life. You detail emotions and feelings so well. Feelings that so many of us have experienced. I love the way you describe yourself. You are a wonderful writer.

    I believe every human being will not be truly happy and content until they fully accept themselves; all aspects of themselves.

    I am so happy for you. I am also so happy I am your friend.

    Thanks for pouring your heart out to the world.


    1. Jocelyn, thank you as always for taking the time to comment and for your compliments and support which are very much appreciated.

      This was a post with a simple message for those who are trying to come to terms with all of this – disliking, or even hating, having to contend with this is natural but it doesn’t have to be the case. Of course, there are many challenges but self-acceptance is there for the taking if we embrace the whole thing.

      Embrace and love the woman in the mirror and, by definition, we love ourself!

  2. HI Amanda – Once again you have written a compelling article – one that I can relate to in a number of ways.For many of us, that descent into shame/guilt and fear of what others around us might say or think of us stems from childhood or our teen years, when the opinions of our parents and/or peer group are paramount. For some it stays with us a lifetime. How I still remember the hurtful and insensitive things that were said to me by my “friends” and even my parents on a variety of subjects. I didn’t have my first CD experiences until well into adulthood, so I can only imagine the nature of those exchanges and how they must have cut you to the core. Although I may have missed CDing in my younger years when it may have been most satisfying, I also escaped the shame/guilt cycle – and from what I hear from so many that may have been a blessing in disguise. All that really concerned me in that matter was that I had my wife’s support and acceptance, and with having that my alter ego was able to flourish.
    It’s great that you have been able to conquer the shade that was thrown at you in an earlier day. It seems some never do. I guess with that certain words or dated pronouns may still have an effect when you hear someone use them. I guess “transvestite” is one, but only because others have ascribed negativity to it. There are some that are deliberately insulting, but that one doesn’t bother me. It’s just old.

    1. Kris, thank you for sharing your thoughts.

      Apart from the message I mentioned in the reply to Jocelyn, there’s another message in all of this and that’s that it’s not going to go away no matter how much we may want it to. Even Mrs A said that when I confessed for the second time to her and, in her own way, she was able to accept that this is how I am, even if she doesn’t want to play any part or even hear about it.

      Your point about missing CDing in your younger years when it ‘may have been most satisfying’ was an interesting one. It’s a very personal thing, of course, but for me, the true satisfaction has only recently appeared. Part of this is obviously having acquired sufficient know-how to put makeup on to an acceptable standard (and, in the process, feel comfortable with the results) but the emotional conflicts when young did put quite a dampener on things, as did the guilt and shame afterwards.

      Thankfully, we live in far more tolerant times now which bodes well for both those in our age group and the younger ones who, hopefully, will not be burdened with the same levels of guilt and/or shame.

  3. Amanda,
    So many get caught up on labels , in truth there’s nothing wrong with them until the media misused them . From my distant school days transvestite simply translated as , to wear the clothes/garb of the opposite sex ( trans = cross , vestite = clothes or garb ) the usual translation was crossdresser , there was never any connection to fetish or whatever until the media added it . In basic terms what was there to hate ? To me the difficult part was accepting the basic idea of needing to dress at all in clothes not normally associated with a boy/man with the feelings of guilt and shame . As you comment acceptance is the problem , as those gradually faded and I became more frustrated with the notion of a boy /man , I called it the male straightjacket . A male lifestyle is deeply imprinted from an early age , more so than for females , society expects the male to behave quite rigidly to the norm whereas women have the freedome to express themselves far more . Thankfully that has changed as gender roles have became more aligned but I’m not sure if that is all to the good , masculinity has softened but many women appear to have forsaken feminity , I admit I don’t like the unisex look . This situation can be quite amusing , I was attending a blood donation session a few years ago , the waiting area was about a 50-50 mix of men and women and as I glanced round I was the only one wearing a skirt but my bubble was burst when the nurse called me by my male name. As I stood up I said to the nurse in front of the other donors , ” we really must do something about my name ” , that raised a few eybrows and some smiles .

    You raise a very important point about “feelings” in the context our genders . In the past I’ve known some to become heated over the expression , ” I feel like a woman ” . In fact we can only really comment about how we feel internally , being transgender do I really fully understand what it’s like to be a man but also I can’t really comment on what it feels like to be a woman . All we can do is express the different feelings we experience when adopting one or the other and in this context I realise our brains can play tricks on us . For whatever reasons I feel far better as Teresa which is reassuring to me after six years but I know some of that is in a very abstract form .

    To return to the debate over the crossdressing label , it’s not one I really think about unless I’m forced to wear male clothes .

    1. Teresa, thank you for sharing your thoughts. In the end, I only used the TV/CD labels to contrast my states of mind before and after self-acceptance. But there is an interesting subtext here and that’s why two words with identical meanings have such different connotations. Generally, it reflects an attempt to ‘rebrand’ to a more acceptable standpoint – similar happened with the term ‘chaser’ being replaced by ‘admirer’ and there are other less savoury examples too. Whether it’s ultimately successful depends firstly on whether society at large is prepared to accept it or just sees through it as a cynical attempt to present something they find unacceptable in a different light and secondly whether, as time goes on, that distinction holds or whether the boundaries become so blurred that no difference is seen.

  4. Amanda,
    As you know I was a member of an online forum with several sub-sections so it was a very active one . Every so often people would try and reinvent a label to accomodate their personal preferences or needs , to say the least it became confusing within our community . I tried to make the point that if we wanted acceptance in society we needed to keep it simple , the more we confuse the general public with new labels the less we will be understood and that leads to the media clouding issues even more .
    Perhaps you should consider crossdressing an action rather than a name because it’s something you need to do to express your inner feelings . Are we somtimes forced to demean ourselves by trying to pass it off as ” just being a crossdresser ” and so denying an important part of our being ? Am I proud of what I am ? The answer is yes providing we are free to openly express what being transgender means . I now quote Jan Morris when considering this question , she became annoyed with the continual question of what gender did she consider being the best author ? Her reply was , ” For myself and all of you get the best parts of both of me “. I consider myself lucky that I can say something similar , the person that has evolved is a better person .

  5. Amanda,

    Your description of how you came to know the complete you, being proud of who you are and loving yourself is a wonderful example of someone simply being honest with themselves. It is not always an easy thing to do because the result can sometimes be a very life-altering experience. People often shy away from the fact that they may actually be different from who they thought they were. Your comments resonate deeply with me because in the summer of 2022 I finally came to the same place as you – knowing the real me, liking the new me and loving the new person I had become. It is a wonderful feeling when you truly, honestly accept yourself. A window opens on an entirely new way of experiencing the world, a way that is much more pleasant and fulfilling
    that before.

    Another very good article from a very good writer.


  6. Fiona, thank you for sharing your thoughts and for your kind words.

    What you said is so true, particularly regarding shying away from being different to what we thought we were. In one respect, there are many reference points to help us – drag is pretty well mainstream these days, there has always been a strong fetishistic presence and clichés like ‘woman trapped in a man’s body’ are freely bandied around, particularly by the tabloid press and daytime TV. All of them had a connection with my own situation – a desire to cross over the gender divide – but I either couldn’t see myself in them or, as in the case of the fetishistic side, feared that I could and hated myself all the more as a result.

    I am the world’s worst overthinker – I couldn’t have churned out over 30 rambling posts here if I wasn’t! – but in the end I realised that I don’t have to justify the way that I am or manufacture an explanation. I’m just a guy who, for whatever reason, feels more complete when presenting as what society determines as female.

  7. Thanks for sharing your story and journey Amanada. I have a very different journey, but along the way
    our journeys touch, so to speak. I think for so many of our community it boils down to one word acceptance. Anyone under the ‘T’ umbrella has to reach a point of acceptance before one can be truly happy, the sooner one does the easier life will be.

  8. Bec, thanks for sharing your thoughts.

    Self-acceptance is key, of course, but acceptance from others is the cherry on the cake, so to speak. Mine came from someone we both know – Cindy at BWBG – but when there’s either secrecy or hostility at home, being able to talk about this side of ourselves to someone who will listen, won’t judge us and just treats us as a normal person goes a long way. I’ve been here long enough to know that there are any number of people happy to look beyond the chromosomes and just accept us for who we are.

  9. Amanda,
    So true the comment to look beyond the chromosomes , if only more could allow that to happen . We are what we are at birth , no one can change that fact so they must learn to accept us for what we are . I know how destructive the secrecy and subsequent hostility can be , it does take some heart searching to make the right decision , living in isolation makes that so much harder if not impossible , the need to talk to like minded people can’t be rated highly enough .

Leave a Reply

Your email address will not be published. Required fields are marked *

Featured Posts

Get The Latest Updates

Subscribe To Our Newsletter

Sign up for the first look at Kandi’s outfits, blog posts, and product recommendations.

Keep Reading

More From Amanda J.