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Crossdressing 101: Part 1 – Coming To Terms With It

Class time!

By Amanda J.

The life of a crossdresser, or CDer as I’m going to refer to them for brevity from now on, can be bewildering.  After all, it’s not exactly normal for a heterosexual guy to feel an overwhelming urge to dress from head to toe as a woman is it?  Society dictates that men should be men, not in touch with their feminine side.  I’m sure we all know the words to ‘The Lumberjack Song’; some may find it amusing but others may feel that it does nothing to move perception of crossdressing away from being a target for ridicule.  And yet read between the lines in that song and the struggles that we face to conform to what society wants while secretly having very different desires are there for all to see (but I will stress at this point that while I may have shopped on Wednesdays, eaten buttered scones for tea and worn high heels, suspenders & a bra, I have never hung around in bars!).

When I started CDing in the 1970s, I had no one to turn to for moral support or advice.  And nothing had changed when, after a two decade hiatus, I returned to it in 2009.  I was on my own, ashamed of what I was doing and desperately wishing it would go away whilst experiencing profoundly fulfilling feelings about my identity when I succumbed.  But eventually I did manage to emerge from the mire and accept who I was.

There are several contributors here who have forgotten more about their CDing lives than I have actually ever experienced.  Ask any of them and they’ll be able to tell you far more about being out and about, shopping for clothes, interacting with others and all of the other facets of the unusual lives that we lead than I ever could.  But I feel that I’m very much on a journey between the totally closeted secretive CDer that I was until recently and the ‘girl about town’ that I aspire to be.  I know from experience, for example, that if I walk into a shop, see a dress I like, go through the rails to find my size and then take it to the checkouts to pay for it, there will be absolutely no issues.  And yet I still feel that rush of apprehension and nervous energy as I do it.  In many respects, CDing is like mountaineering in the Himalayas – we get the exhilaration each time we scale a peak but then realise that there’s another higher and more challenging peak to conquer – and I’m very much still in the foothills.

So who is this series aimed at?  In short, those struggling to come to terms with these strange feminine thoughts that they’re having, don’t know where to turn for support, are worried about shopping for clothes etc. or are paralysed with fear at the thought of being out and about en femme.  So if any of those sound close to home, what follows is for you.  I’ll often use my own experiences to illustrate the points that I’m making, not because I believe that I’m a shining beacon of inspiration – I most definitely am not – but to give hope to those just a few steps behind me that what may seem like insurmountable hurdles can be negotiated.

Anyway, enough of the preamble so let’s get started and  go back to first principles.  What exactly is a crossdresser?  A quick Google search returns definitions along the lines of:

‘a person who wears clothing typical of the other sex’

That all seems reasonably clear.  But is it really?  It doesn’t say how much clothing is involved.  It doesn’t give any guidance on whether a full, convincing transformation is required or just being a ‘bloke in a dress’ is fine.  It doesn’t specify what the motives for wearing said clothing are.  And so on.  So if this post is not to rival ‘War and Peace’ in length, we need to narrow things down a little bit.

To be clear, there’s absolutely nothing wrong with CDing whatever the motive.  If a little bit of underdressing – wearing nylon hosiery under male clothes for example – satisfies your urges, then that’s fine.  If crossing the gender divide evokes a sexual reaction like no other you’ve ever experienced, that’s also absolutely fine.  If exclusively dressing as a certain type of woman – perhaps a flight attendant, French maid or lingerie model – floats your boat, then that’s fine too.  And if wearing the clothes without makeup or wig does it for you, then guess what – it’s fine by me!  But I’m going to put those and many other flavours of CDing including drag, female impersonation and other artforms to one side and focus in on one particular area – the complete and total transformation of a male into the most convincing female that they can be.  And I do claim to have some knowledge about that given that I am a male who, for some inexplicable reason, needs to transform himself into the most convincing female that he can be from time to time.  So I’m going to use myself as an example to give reassurance to anyone reading this who is trying to come to terms with, and perhaps battling, thoughts and urges to cross the gender divide that they may be having.  Or, to put it another way, if I can get on top of all of this, so can you!

With the exception of my wife, no one who knows male me is aware that beneath the slightly scruffy, bespectacled 63 year old guy they recognise lurks an inner woman, the polar opposite of ‘him’ in practically every respect. And whilst Mrs A does know that I CD, she has no idea of the extent of my feminine persona.   In my normal life, I wouldn’t dream of wearing anything vaguely feminine.  I have no feminine mannerisms that I’m aware of.  I’m heterosexual and married with two grown up kids.  My interests and hobbies are typically (or probably ‘stereotypically’ would be a better word) male.  I could carry on but I’m sure you get the picture – I’m just your typical guy in pretty well every respect.  Except that I have frequent thoughts of crossing the gender divide to present as my female alter ego ‘Amanda’.

At this point, I want to stress that I am not a woman trapped in a man’s body and have neither the desire not the need to permanently transition to female.  I’m just dealing with an ongoing desire & curiosity to experience life from a more feminine perspective when the mood takes me.  For most of the time, those thoughts are under control and just simmer in the background.  But every so often they boil over and become almost uncontrollable urges.  I say ‘almost’ uncontrollable because there is, of course, one way to instantly calm the urges – retrieve the bags from their hiding place, cut the cable ties, spread out the contents on the bed and start the transformation.

This is not something I have any control over.  Sometimes I can go several months without needing to transform myself.  At other times, it’ll be several times in a week – my personal record is spending a total of 17 hours dressed in one week – that’s 10% of the total hours in the week.  That was a pretty unusual week because, averaged over the year, I estimate that I spend only around 2-3% of my time dressed in female clothing.  And that’s quite significant because for the other 97%+ of the time, I’m fulfilling those roles in my life that I place the highest priority on – the roles of husband and father.  I would not have it any other way.

I should also make passing mention of how I got here.  Whilst memories from over half a century ago are hazy, I do recall being particularly interested in the girls in my class at primary school.  At an age when I was too young to have any sexually motivated desires, I remember wanting to play with the prettiest ones and being particularly fascinated by those who wore ‘nylons’.  They were very much the preserve of adult women in those days but, oh boy, did that handful of eight year old girls who wore them look grown up?!  Against that background, it was probably inevitable that, in my mid-teens, the urge to try a pair on for myself would intensify culminating in the fateful day when I found a pair of my mother’s discarded tights and tried them on.  And that was the day, the date sadly unrecorded for posterity, when I became a crossdresser.  Not because I’d worn an item of clothing ‘typical of the other sex’ – many males have done that to win a bet, for fun or for theatrical purposes – but because the die was cast.  It was only a matter of time before full outfits were being worn and the battle began in earnest.

It’s a battle that I think that most of us have fought.  We’re conditioned to act in a way that society views as ‘manly’ and yet we look at women with both admiration and envy, trying to work out whether we want to be with them or just be them.  We shop with our wives taking pride & pleasure in buying them clothes that we secretly wish we were buying to wear ourselves and perhaps living our lives vicariously through our wives.  We lament the rigidity with which society dictates what we should wear while our wives have the freedom to wear whatever they want, including borrowing our clothes, without anyone batting an eyelid.  And many of us wish that, at the point of our conception, Ms X had got to the egg before Mr Y.  Of course, our life would have been different in every respect but at least our mind and body would have been aligned and we would no doubt have had a happy life as a wife and mother.

There’s an important point to be made here.  There’s a huge gulf between wishing one had been born female and wanting to take steps to become female.  The former does not in any way imply the latter even though for some people both ring true.  CDing can give us an insight into what might have been but it doesn’t mean that we’re buying a one way ticket to womanhood.

It was around 45 years after the aforementioned ‘fateful day’ when I finally came to terms with being a CDer.  When I accepted that there’s a part of my personality that is decidedly female and needs to be given the same freedoms that I give my ‘normal’ male side.  When I realised that ‘Amanda’ is not someone I become, she is part of who I am in the same way that ‘he’ is.  Today, I may have made an outfit choice that society will determine is well and truly in the male camp but tomorrow, it may be different.  However I happen to be dressed doesn’t change who I am at heart, though.

Simply put, being a CDer is nothing to either fear or be ashamed of.  It’s just an indication that, like every human, we’re multi-faceted with, in our case, a stronger feminine side than most guys.

But let’s make no bones about it, self-acceptance isn’t easy.  It involves turning every preconception we may have on its head.  We may laugh at the Lumberjack Song, a pantomime dame or a CDing comedy sketch but it’s no laughing matter when we equate those to our own situation.  We may suffer crushing disappointment or worse when, after finally plucking up the courage to acquire and try on a female outfit, we look in the mirror and see not the woman we’ve fantasised about being but just, well, the archetypal bloke in a dress.  We hate ourselves for both having these thoughts and for the web of deception that we spin to keep it away from our loved ones.

And really, all I can say is hang in there.  Pretty well every CDer will say the same thing – it can’t be beaten and resistance is futile.  In fact, what I found is that the more I tried to resist it, the stronger it fought back.  And the physical aspects can be conquered too.  What any woman will tell you is that not all fashions work on all women.  What looks good on one can look absolutely awful on another and, as you progress, you’ll find styles that work for you.  Women aren’t born with the ability to apply makeup, they have to practise and learn from their mistakes (although they tend to have their mothers & older sisters as tutors while most of us have to resort to YouTube).  Whilst it can sometimes be difficult, we have to persevere and learn from the disappointments, not let them dishearten us.

And when we do persevere, something wonderful happens.  One day, we look in the mirror and looking back, in place of the aforementioned bloke in a dress, will be a smiling woman, barely able to control her happiness.  She’s unfamiliar and yet instantly recognisable.  We feel we know her well and yet want to get to know her better.  And when she’s not been around for a while, we miss her.  And that’s the point at which we realise that we’ve finally uncovered our whole self.  And how many people ever really get to say that?

To close each part of this series, I’m going to list five key takeaways.  Here are the first five:

1.  There is absolutely nothing wrong with CDing.  We don’t know why we need to do it, we just do and thankfully, the days of it being a criminal offence are well and truly in the past in most western jursidictions.

2.  There are many flavours of CDing and we don’t have to conform to a single definition.  Whatever works for a particular individual is absolutely fine and nothing to be ashamed of.

3.  Self-acceptance is key.  The need to CD is not going to go away so the sooner it’s accepted, the sooner the inner woman can flourish and enjoy life.

4.  Being a CDer does not mean a one-way ticket to womanhood, a woman trapped in a man’s body or anything else like that.  It just reflects, for whatever reason, a need to experience life from a feminine perspective from time to time.

5.  Being a CDer doesn’t mean that male life cannot be enjoyed.  In fact, for most of us the duality gives the best of both worlds.

That’s enough for now.  Next time, we’ll look at how to put an outfit together by shopping on the high street.


18 Responses

  1. Amanda,
    A wonderful post, putting into words what so many of us experience. This will be helpful to so many people.

    I suspect in Part 2 you will make some comments about CDs and transgender issues. Shopping on high street for an outfit does not mean one has to think the end result will be “full time” womanhood.

    From a proud Canadian lumberjack, thank you.


    1. Jocelyn, thank you as always for your kind words and support.

      As you allude to, we live in constant risk of having conclusions drawn from our activities. Slip on a pair of heels and, apparently, we were born for womanhood. Look a little too comfortable in our feminine skin and the safety net of the door back to our male lives will be slammed shut behind us! And that warm smile from the sales assistant which we took to mean gentle approval was really saying that, even though we were shopping ‘in drab’, she’s seen it all before and resistance to the inevitable will ultimately be futile! Admittedly, it’s not easy when all of those gorgeous clothes and shoes are sending out subliminal messages but I’m standing firm!

      And from one lumberjack to another, enjoy your buttered scones for tea!

  2. Amanda,
    I still find it intriguing why one item of clothing can trigger that deeper feeling , what exactly is it ?

    Considering your five points :-
    1) I desparately wanted to know why we do it not only for me but at some point trying to expain to my family . I knew it was stupid to think I would never be caught out , so I wanted to be prepared .
    2) We should consider ” crossdressing ” a noun and a verb . I am a crossdresser is making a simple statement , I crossdress because I have an inner need , it’s the stregth of the inner need we must really think about .
    3) Acceptance of ourselves can’t happen until we accept it’s a need we can’t deny , we are ” lifers ”
    4) We have to be guarded in making that statement , I admit I’ve said it myself in the past but discovered with the help of counselling that I was in denial because I was trying to protect other people . If you wanted to add another item to your list it would be honesty to yourself , being transgender means you can’t protect everyone else for ever .
    5) After reading Jan Morris I realised we can contribute far more , in her words , ” you are now getting the best parts of both me ” . It’s not living a male life or a female life but a complete life .

    Amanda , please don’t feel you are not qualified to write your thoughts on crossdressing , OK I’m further along the road or perhaps on a different road but your comments are still valid , everyone has different views and attitudes to a difficult subject .

    1. Teresa, thank you for sharing your thoughts.

      Whether the tights were a trigger or a consequence of latent feelings is a point to ponder. They certainly evoked a reaction ‘downstairs’ but things very quickly moved on to full dressing but there was definitely no motive to CD just for the reaction – in fact I quickly realised that it was undesirable, not only because of the obvious issues when it happened but also because of the feeling of shame afterwards.

      And now to your numbered points – unsurprisingly, I disagree with some but that’s the beauty of debate. I’ll also stress that the post was written with the newbie, not ‘seasoned pro’, in mind so much of what I wrote won’t be relevant to ‘old hands’ like you, Kandi and many of the others here!

      1. I think many of us have looked for answers. Many born in the 1950s & 1960s latch onto DES (diethylstilbestrol – a drug given to pregnant females to combat miscarriage but widely believed to cause transgenderism in male offspring) because it gives legitimacy to the condition and, in particular, moves the focus away from sexual motivation which leads to guilt in the individual and potential hostility from spouses.

      2. Good point although I think that being able to say ‘I am a CDer’ is a key step in self acceptance.

      3. To a degree, yes, but I suspect that a proportion of the community would deny a need and assert that it’s just something they derive pleasure from. Whether that constitutes a need is, of course, a matter for debate. That said, I do agree that the target audience for this post are the ones fighting the emotional battles, not doing it for the fun of it.

      4. This is probably where I disagree most but it’s important to draw a distinction between CDers and TG people and I did stress that the post is aimed squarely at the former. Of course, in some cases, one leads to the other but by no means always. As regards honesty, to focus in on myself, I know that I have a deep curiosity and, if things were different in my life, I’d be quite open to the idea of finding out in practical terms how far I’d want to take this and if I realised that the answer was ‘as far as possible’ it would be driven by the pull to something I perceived as better, not dissatisfaction with who or what I am and a need to walk away from that. But, for me, prioritising the needs and wants of those around me is far more important than what for me would be a voyage of discovery.

      5. I think that’s a point of view that many of us can relate to although, in JM’s case, there was the total relinquishment of her male side. There are elements of my personality that seem to fit far better in a feminine persona but living in that persona is not a prerequisite to displaying them.

      Being ‘qualified’ is, of course, open to interpretation and many who profess to have qualifications don’t really know what they’re talking about! As I said in the post, there are many here with far more real world experience than me but what I want to do is to take people along for the ride as I navigate the sometimes choppy waters. I like to think that people who do come along will feel that their life has been enhanced but it’s by no means guaranteed!

    2. Teresa,
      Amanda’s point 4) is absolutely correct and your effort to guard against it is inappropriate.
      There is no road with an end destination of 100%. You can’t be further along something that doesn’t exist. You imply Amanda (and probably myself) need to catch up to you on the road because we are in denial; no thanks.


      1. Jocelyn,
        As I mentioned in my comments in (4) at one time I didn’t see it as a road I also admit not everyone is driven to the point of ending their life , so in my case it was a road I was heading down to find answers and come to terms with ME . It wasn’t an easy decision to take , I had a business to run and two children at university , my wife saw counselling as a cure so I really struggled with denial and tying to keep the problem in context with the needs of my family .

        My comments were not suggesting eveyone has to take the same road but at the same time be honest with yourself to prevent your whole world falling apart . It’s quite scary to reach an age when your life is in turmoil and you also know time is running out , for me there was light at the end of the tunnel .

        Amanda ,
        Many thanks for accepting my comments , I realise I’m a minority here but like you we can all share our experiences and thoughts . If I only help one person then it’s been worthwhile , we must thank Kandi for giving us the opportunity .

        Sophie raises an interesting point about the gender euphoria as opposed to gender dysphoria . I’m sure the majority know all about the “highs ” of dressing and those dreadful , shame filled “lows ” . It’s when they even themselves out that you realise there is still something driving the need , for years I called it a ” gut feeling ” which didn’t subside until I went full time , it quelled my dysphoria . Do I still get an euphoria ? I see it as a feeling women get when they have a planned special occasion and they find something new to wear , the feel good factor .

    3. To add to what I said, this post and particularly the ‘takeaways’ at the end were intended to give reassurance to those bewildered by the feelings they are experiencing and, whilst there will always be exceptions to the rule, for the vast majority of us transition, either social or medical, is not the right answer and to suggest that it is is dangerous. I know from my own experience that trying to come to terms with it and avoid blowing up one’s whole life in the process is challenging and emotionally draining but if I’d been told that transition was the only answered, things would have got a whole lot worse.

      What’s important here is that everyone takes things one step at a time and knows that taking that step is unconditional and will not lead to anything else if they don’t want it to. I know from experience that looking in the mirror and seeing the person you always dreamed of being smiling back leads to incredibly powerful emotions and suggests options that never previously seemed possible. But the time to consider those options is when they present themselves, not at the outset before we’ve even had a chance to come to terms with things.

  3. “When I realised that ‘Amanda’ is not someone I become, she is part of who I am in the same way that ‘he’ is. ”

    That is a very important realization and level of acceptance.

    1. Christina, thanks for the endorsement. It was very important for me because it took the emphasis off the clothes as being the only ‘gateway’ into this side of my personality. In particular, I no longer feel fraudulent communicating as ‘her’ while dressed as ‘him’ if you see what I mean. I’ve also noticed far more of a desire to be seen by others as the emphasis has shifted from being dressed as a woman to being dressed as me; society may declare that some of my outfits fall decidedly into the female camp but that’s ultimately an arbitrary distinction and constraining. Life is much easier when you’re ‘me dressed as me’ than ‘a man dressed as a woman’!

  4. Amanda,

    I agree, your comment – “self-acceptance is key” – is so very important no matter what stage of the crossdressing journey someone in on. For me, self-acceptance resulted in my living a completely new lifestyle. Others may not have such a dramatic change as the one I experienced but they will definitely find themselves in a much better place emotionally and psychologically. A friend once asked me how I felt when I accepted who I really was and I replied “I am Fiona and she is me”.

    1. Fiona, thank you for taking the time to share your thoughts and you’re absolutely right. It’s pretty well inevitable that we will try to fight the urges but it’s a fight that most of us can never win. Equally, as you suggest and as I said in the post, it’s not necessarily a one way ticket to womanhood (and for the vast majority of CDers, it isn’t) but there is a point of equilibrium for each of us and self-acceptance is a prerequisite to finding it.

  5. Many thanks Amanda

    I’ve been following your posts almost since you began and I found it very comforting to know that you have the strength and courage to carry on dressing despite your wife’s discouragement.

    I am in a similar situation except having adult step-children instead of my own and my wife doesn’t want to see me dressed but does agree that I can go out monthly to a CD social group. One of the group members recently introduced me to the concept of ‘Gender Euphoria’ which is the feeling we sometimes have when you’re dressed and it feels just right.

    For me, that sums up why I dress very well and its a much more positive expression than the more commonly encountered Gender Dysphoria.


    1. Sophie, thank you for your kind words and I think you’ve hit the proverbial nail on the head. GD is a debilitating condition for those who have to endure it but I’ve never really been able to relate it to myself. I wouldn’t trade my roles as husband and father for anything and yet the feelings each time I unleash the inner woman are like nothing else I’ve ever experienced in life. It permits us to be happy in either role – there are always going to be tradeoffs but I look at myself now and think that I’ve got a pretty good compromise.

      Thank you again for putting this idea into the mix.

    2. I have to jump in here: “I’ve been following your posts almost since you began and I found it very comforting to know that you have the strength and courage to carry on dressing despite your wife’s discouragement.”

      This is EXACTLY why we are here! This is our community. Thank you Sophie for reading and especially for commenting.

  6. if you accept the validity of gender dysphoria then there is no reason for guilt.I don’t see why every other mental aberration is accepted but in our case we are told that we’re nuts and/or our spouse doesn’t want to hear about ti.

    1. Emily, that’s a good question. My wife could see that things ran far deeper than I was prepared to admit and had to deal with a mixture of resentment that I’d not disclosed it at the outset of our relationship, anger about the deceit and fear about where it was actually leading. What she couldn’t see was the emotional impact it was having on me – not dysphoric feelings but being worn down by trying to battle the urges in a vain attempt to be the husband and father that she expected to be and, importantly, that I wanted to be. To compound the issue, when I confessed first time around, I didn’t have any appreciation of what was going on myself. Nowadays I do and fortunately, having inadvertently forced myself to do a second confession at the start of this year, I was able to talk to my wife about that side of things. The clothes are the therapy, not the ‘illness’ and things are far better now we both understand that.

  7. A really good article, a lot of time it take us decades to come to this realisation. I confessed to my girlfriend about 4 year ago and we have gradually been exploring my dressing and expanding boundaries. It is usually her that comes with suggestions and not me. I am lucky as it was not a conversation I could have ever had with my wife. I now dress at home a couple of times a year with her and we have been out together and with her friends dressed to shows, nights out and meals and not had any bother.

    1. Tanja, thank you for sharing your experiences and thoughts. You’re right, it often does take decades and sadly that’s often because we’re having to deal with it all in isolation without anyone to share our thoughts and worries with. It’s wonderful that you are able to explore this side of yourself with the participation of your girlfriend and have experiences that many of us can only dream about.

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