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Go On, I Dare You!

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By Amanda J.

I’m sure we all remember our school days when dares were the order of the day.  Dares to play a prank on another pupil or teacher, dares to hide the most unpopular kid in the class’s trousers while he was changed for sports or even dares to ask the girl of your dreams on a date after confessing to a classmate that you thought she was quite cute (possibly with the threat of ‘if you don’t I will’ which I have to admit to having been on the receiving end of!).

And it struck me that our CDing life is full of dares too.  Not usually dares given to us by someone else, well not directly anyway, but dares we set ourselves.  We dare ourselves to go and buy our first outfit, we dare ourselves to reach out to other like-minded souls via social media and – and this one is the biggie – we dare ourselves to set foot outside the safety of our home or hotel room and venture into the big wide world.

I well remember my first time and, indeed, I’ve written about it here.  Gradually, I had come to realise that the four walls of my home which once had provided me with all the security I needed while exploring my feminine side had come to constrain me.  And the more I thought about it, the stronger the urges to break free became.  And eventually, when I could stand it no more, I dared to pull back the curtain that covers the window on my front door and peer through.  And within a day or two I stood by that same front door and dared myself to open it and walk out into the world.  And since that day, I’ve repeated the exercise a further five times.

If we never move out of our comfort zone in life, there’s a risk that we won’t achieve much.  But there’s a problem with most dares – in the overall scheme of things they achieve little or nothing of tangible significance.  Prank a teacher or unpopular classmate and, if you’re lucky, it’ll be ‘a good laugh’; if you’re unlucky, it’ll be a detention.  At least the cane is no longer used!  And let’s face it, if you need to be dared before you’ll ask the cute girl of your dreams out on a date, that interaction is probably doomed from the outset!

Now I’ve already said that I’ve been out a total of six times and the first five were out and out dares.  Me daring myself to leave the house for the sole purpose of leaving the house.  Nothing more.  In many respects, that’s fine because we have to walk before we can run.  My co-contributors here have amazing adventures in the outside world but I’m sure that each and every one of them has a similar story about the apprehension they felt in the run up to the first time they stepped into the outside world for the simple purpose of….stepping into the outside world.

And that was how I felt on each of my first five outings.  I wanted to go out but didn’t need to go out.  There was no ulterior motive other than to experience the outside world en femme.  Now many would argue that that is as good enough a reason as any and I’d be the first to agree.  Breaking free from the confines of the closet is liberating, exhilarating, validating and ‘everything-else-you-can-think-of-erating’.  It’s a rush and an assault on the senses.  It’s about accepting that ‘she’ is a part of who we are, not someone we become and our validation of our feminine persona.

It’s also nerve wracking because of the perceived risks involved.  We can discount those risks – our neighbour would never recognise us if they were out at the same time we were, we don’t care if someone realises what we really are, most people see little issue with a guy dressing in women’s clothing in these enlightened times.  And so on.  But while the risks may be small, they are present and we have to weigh them up against the desire to break free.  I always check that my neighbours are out when I leave the house en femme but I’m well aware that they might have returned home by the time I get back and I have to admit that I restrict my outings as a result.  I know that I will probably get away with it but I also know that my luck will run out at some stage.  And so, whilst it’s fun to dare myself to push Amanda’s envelope ever further, it’s not something I do with gay abandon.

And I guess that more or less sums up my love affair with CDing.  Ultimately, it’s felt like a huge game of dress up with the only purpose being…to dress up and get a glimpse of what might have been.

But what is the purpose of clothing?  We can argue with some justification that the skirts, dresses and heels we wear enable us to project this side of our personality but that’s the purpose of specific items of clothing, not clothing in general.  Fundamentally, clothes have just two purposes – to keep us warm/protect us from the elements and preserve our modesty.

And that brings me on to outing number 6.  On the day in question, my son was away on holiday and my wife was at work.  So there was no need for me to get dressed in my guy clothes and then, an hour or two later, decide to have some femme time.  That day, I retrieved my stash as soon as I got out of bed and got dressed for the day in feminine attire.  And then I did my makeup and spent the morning preparing future Kandi’s Land posts and just generally enjoying my total transformation.  And despite probably looking as acceptable as I could ever hope to look when doing my own makeup, leaving the house was the last thing on my mind.

Now, while I was enjoying some femme time, I was awaiting a delivery.  A few days earlier, I’d ordered myself a new black bodycon dress from Amazon and I was awaiting the email to say it was ready for collection at the local Amazon locker.  It would probably arrive in the early evening by which time I would have packed my feminine things away and it would be a case of picking the dress up and putting it away until the next opportunity to dress arrived.  But the notification that it was ready to collect didn’t arrive in the early evening; it arrived at 12:22pm.  And that posed an interesting dilemma.  Given that I hadn’t planned to go out, should I wait until I changed back into drab before going to collect the dress?  Or should I change back straight away and get the dress immediately?

Neither option seemed particularly attractive.  I really wanted to get the dress as soon as possible so waiting wasn’t an attractive option and did I really want the faff of wiping all of the makeup off to go out only to reapply it when I got back home a short time later so that I could try on my new dress in all my glory?

There was, of course, a third option and an interesting option it was too.  That was to go as I was and as soon as that entered my mind, a strange feeling engulfed me.  Physically speaking, it was very similar to the adrenaline-charged feelings I’d had when I’d stood on the threshold previously.  But it quickly became apparent that, whilst physically similar to what I’d experienced before, these were very different feelings.  Whereas previously, they’d been driven by an inner fight to overcome all of the reasons not to go out, now the inner voice was saying ‘whoa, steady on Amanda, not so fast!’.

But it only takes a minute or two to collect the essentials I need when going out – most notably a means of getting back in again (otherwise known as house keys!), phone, glasses and my usual ‘bug out’ kit of jeans, T-shirt, shoes and makeup wipes (in case I need to unexpectedly change before arriving back at home) – and before I knew it I was in my car driving the short distance to the Amazon locker to collect my new dress.  And, as I was driving, the significance of what I was doing really hit home.

‘Significance?’ I hear you ask!  Even by my standards, it wasn’t particularly noteworthy in itself.  I was far more exposed to the public on each of my three prior outings to supermarkets and, with the exception of a van pulling away as I arrived at the locker, there was no one anywhere near me.  But during the maybe ten minutes that I was out of the house, I realised that for the first time in my life, I was actually living the dream rather than just going through the motions.  The clothes had returned to their fundamental purpose – to keep me warm (not that I needed it as it was a hot day) and to hide my modesty (which, for a CDer, is probably the important one!) and the outing had an unconnected purpose of its own – to pick up a package.  The fact that the package was connected with my CDing is irrelevant because it would have been exactly the same scenario if, rather than a dress, it had contained goods relating to one of my other interests that I was eager to get my hands on.

Perhaps when I had those feelings, my subconscious was saying ‘go on, I dare you’ but I don’t think so.  In fact, I’d go as far as to say that it was actually saying ‘I dare you not to’ but the reasons for going as I was were so overwhelming that it was a dare I was not prepared to take on.  In fact, it would have been illogical not to go as I was – I wouldn’t have got changed to collect a parcel from an Amazon locker in my day to day garb so why should this occasion be any different?

Of course, one swallow doesn’t make a summer as the saying goes and I don’t doubt that, one day, I’ll be standing outside a ladieswear shop in my full finery for several minutes daring myself to overcome my fears and go in to get a closer look the gorgeous dress in the window, or standing outside a Starbucks atop my heels, quaking with fear as I dare myself to enter and order a hot drink or daring myself to overcome my jitters and do any number of things that women in general and my co-contributors here take for granted.  And I know that the fact that I couldn’t get out of the front door to collect my Amazon package fast enough doesn’t imply that I’ll have a similar reaction when faced with other scenarios.

What I’ve come to realise, though, is that this is a journey of self-discovery.  The idea that I would not only willingly leave the house fully dressed and made up but that I’d do it in preference to the safer option of changing back into drab was inconceivable even just a few months ago, as was the idea that it would feel like the most natural thing in the world.  But take a step back and ask why would I not do what I did?  I could list a few reasons (more correctly spelled E-X-C-U-S-E-S!) but if I’m going to declare, as I do, that ‘Amanda’ is part of who I am, not someone I become, why should I fear stepping into the world dressed in a perfectly reasonable manner for anyone called Amanda?  If I can look in the mirror with a sense of euphoria because I like what I see, why should I fear that side of me being seen by others?

The life of a closeted CDer is, to say the least, challenging but there are people who face far greater challenges than ours in life and that really puts things into much needed perspective as far as I’m concerned.   But we face challenges because there are rewards to be had.  Sometimes those rewards are financial, other times our very survival depends on them but just occasionally our reward will be to be taken to a place we never dreamed would be within reach.  A place where things just seem to make sense and  where doors are opened for us.  Somewhere where we can realise that all of the struggles, frustrations and anxieties were not in vain but can be overcome.

And who’d have thought that an Amazon locker would be one of those places?

Get your own bodycon dress, just like Amanda!


13 Responses

  1. Amanda,
    A very wonderful dissertation on what goes on inside your head, and the heads of many of us. And as you say, it eventually comes down to just living life. Running an errand dressed in any fashion is what people do. The fact that we do it while wearing a dress or skirt or leggings should be “no big deal”.

    When I go out en femme and shop or bank or post office, I really don’t think any different than if I was in drab. I’m just a woman doing her thing.

    Great post, and just keep being you.

    Lots of love,


  2. Jocelyn, thank you for your kind words.

    Many have wondered exactly what goes on in my head but few have ever got to the bottom of it, myself included!

    To be serious, though, there was a significant lesson to be learned in my experience; it’s a lesson that you and all of our co-contributors here have already learned but there are many who needlessly worry about the simple act of being out and about. We can fret and easily find 101 reasons (once again spelt E-X-C-U-S-E-S!) why going out is a bad idea purely and simply because the only purpose is going out. But when there’s a genuine purpose and the decision is not ‘do I or don’t I’ but, instead, ‘get changed or go as I am’, things start to balance up. It’s not a trivial decision by any means – if either of my neighbours had been in, I wouldn’t have done it – but when the balance tips in favour, as it did here, it demonstrates that many of the fears we may have are groundless. In the end, when all of the doubts and fears are stripped away, it’s just dressing and no further amplification is required.

  3. Hi Amanda,
    Thank you for another wonderfully entertaining post. The only sad part is when it comes to an end. But the best part is knowing another one is in the making. I really envy people like you with the ability to put things into words the way you do.

    As a girl who gets out quite a bit I can honestly say that, for me, the apprehension of walking out the door never goes away. Nor does the excitement and I wouldn’t want those feelings to go away…..ever! If I’m going to Vancouver to see my girl friends down there it’s a 3 1/2 hour trip each way, 7 plus hours of being me. And every time through the each drive thru or stopping for gas the apprehension and excitement builds. And I all ways stop at one of the truck stops to use the ladies room. It’s always full of trucks and I just love being a bit of a tease. Both for me and giving the truckers something to talk about.

    I wonder if all the CIS girls who dress down all the time do it because the desire to look pretty and feminine has become mundane to them? I just hope it never happens to me. Wanting to be pretty and feminine is another perk of the gift we were given at birth.

    Trish ❤️

    1. Trish, thank you for your kind words and for the compliment!

      In the end, it’s just an intoxicating feeling to set the inner woman free and even if there are regrets or feelings that we perhaps sailed a bit too close to the wind, those soon pass as we look at the next peak to scale. That said, I’m still not entirely sure why the outside world is such a draw when staying within the confines of the house removes practically all of the risks we face.

      And as for all the girls who dress down, I suspect that there’s a hint of truth in what you say. For us, spending an hour or two ‘getting ready’ or walking around in heels is part of the experience – for them it’s a faff at best and at worst downright painful (as my stilettos frequently remind me but we have to suffer for our art)!

  4. Amanda,
    No denying you’re a “Brtit ” when you mention the dreaded cane ! I’ll not say anymore about that apart from ” Ouch !” does that hurt .
    I’m sure most of us recall vividly the first steps outside the front door . Perhaps it’s wrong to overlook my first few drives but the big step for me was leaving my home dressed in a full length ballgown to attend my very first trans meeting . The ballgown might sound excessive but the first meeting was actually a dinner/dance to celebrate their 4th anniversary . I will add this was with the full knowledge of my wife , she actually sat in a layby near our home to give me the all clear to leave but there was no way she wanted to see me . It was the first on many levels , being dressed to the nines with full makeup and driving in high heels but more importantly I was going out totally as a woman to meet others in a public place , a hotel . What sticks in my mind is other motorists trying to get a second look at the blond in the driving seat during the journey .

    Commenting on the reasons why we wear clothes , I do feel there is a third reason for women which men might not fully appreciate and that is looking attractive , glamourous or even sexy .

    As for the dares , I’m sure most would admit it’s par for the course as far as transgender people are concerned . I admit it is a rush , quite exciting but also risky . I remember the fun stories when buying my first underwear , the letter I contrived to buy my first pair of heels and being caught out by a friend of my son’s with a basket full of makeup items . I ran my business from home and sometimes I was caught out by customers calling unannounced , on one occasion trapped in a sundress with a totally stuck zip .

    It’s ironic for me that it’s now gone ful circle , I don’t want to be caught in male mode , on the very rare occasions I have to leave my home I double check no neighbours are about before I can speed off down the road .

    Do I still have some dares left in the offering ? I’ve promised myself to take a cruise as Teresa but that is after I formally change my name so I can travel with the correct passport and I’m still debating the pros and cons of that. Otherwise my life is virtually normal , I’ve done most things on my wish list .

    I wonder if the day you don’t have to dare yourself means you’ve finally reached your destination .

  5. Teresa, thank you for sharing your thoughts and experiences.

    The third purpose of clothing is an interesting one and arguably applies as much to men as it does to women. However, it is a product of certain garments, not clothing in general since a walk down any high street reveals beyond any doubt that there is an awful lot of clothing that could never be accused of making its wearer look ‘attractice, glamorous or even sexy’!!

  6. Amanda,
    I recall some years ago when out shopping with my ex-wife , we sat in the balcony of John Lewis having a coffee looking down at the shopping cocours at the passing shoppers . I remarked that the shopping centre was full of clothes shops selling lovely items so why do most of the shoppers look like sacks of potatoes ? Where do those lovely clothes go ? The obvious reply from my wife was , ” trust you to notice something like that , I dread to think what you would be wearing given half a chance !”
    On the whole men tend to be more practical about clothing or just go along with what they’re told to wear . Every Xmas I would get a pair of trusty old cord trousers and a lumberjack style shirt . I tried to show my gratitude but underneath I was desparate for some recognition with something more feminine .

    1. Teresa,
      I solved the “what if my neighbor see me leaving” problem by parking my car INSIDE my attached garage AND having an automatic garage door opener/closer. I just need to get into the car before I open the garage door. My neighbors have all seen me in heels.

  7. Amanda,

    Now that you have been out en femme six times, I have absolutely no doubt that after another half dozen or dozen times you will start to find yourself in a much more comfortable place when out in public . Each outing will build up your confidence level, making the next outing more comfortable and building your confidence even further. At some point being out as Amanda will feel entirely natural and it is at that point that your dressing experience will be taken to another whole level. It is a very rewarding feeling to realize that you are finally becoming the person you truly want to be. Enjoy the ride!

    All the best.


  8. Fiona, thanks very much for your words of support. Of course, there’s going to be apprehension but, in the end, they’re just clothes. Someone, somewhere will always guess our secret and once we realise that, providing we take a few basic precautions, that doesn’t matter, things get a lot easier as I’m finding out.

  9. Amanda,
    My daughter made the same comment , ” They’re just clothes , pieces of material ” .

    I know most of us consider them far more than that , perhaps we should consider more like a uniform , they tell the world where we belong and what our status is . We look up to people depending what they wear , to us the way a woman dresses says so much about her , we tend to categorise women far more than men by their clothes . I’m sure you like me give your female wardrobe far more thought than you did a male one . Kandi is a perfect example of setting the scene by what she chooses to wear , calling them ” just clothes ” undermines how effective they can be .

  10. Amanda, at the start of your post when you spoke about dares, i really couldn’t relate to that, which got me thinking as to why at no stage did I ever think of the various ‘firsts’ that I did as dares? I just did what I did because it felt like something I needed or wanted to do.

    But then when you got to the end of your post and said “The idea that I would not only willingly leave the house fully dressed and made up but that I’d do it in preference to the safer option of changing back into drab was inconceivable even just a few months ago, as was the idea that it would feel like the most natural thing in the world.” I thought AHAHA now THAT I can relate to.

    As always your posts are really fascinating and thought provoking..

    1. My posts are full of twists, turns and surprises and thanks for the compliment, Bec!

      Ultimately, how we feel probably depends on our circumstances. Five of my six outings started from home and the sixth from a hotel. In each case, there was a high risk zone – my front driveway or the compact reception – where I could have been spotted/ recognised and that had to be negotiated before I could get to the safety of anonymity beyond. Doing my own makeup adds to the insecurity as viewing the results on a selfie usually reveals horrors not noticeable with my appalling uncorrected eyesight.

      Of course, it gets easier the more we do it as I found out.

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