Travelling Pretty

By Amanda J.

I have to confess to a tinge of envy every time I read an account of ‘flying pretty’, in other words taking a flight in one’s feminine persona.  Whilst I know the reality to be very different these days, in my mind there’s still a hint of glamour in the whole air travel thing, possibly driven by the traditionally smart uniforms worn by cabin crew.  Even the idea of walking round an airport without actually going anywhere seems attractive and has been something that I’ve contemplated doing in the past.

But the truth is that flying pretty only seems to be a ‘thing’ on the western reaches of the Atlantic and beyond thanks to the ubiquity of domestic air travel stateside.  On my side of the Atlantic, it just doesn’t seem to feature on bucket lists and breathless accounts of the excitement experienced breezing through security in a feminine persona just don’t appear.  That’s not to say it doesn’t happen but I suspect that most, if not all, of those doing it are at some stage of transition and they’re flying under their sole persona & identity, not a CDer pushing the envelope under an occasional alias.

The thing is, in Europe, domestic air travel, is often not the fastest option.  Yes, we have domestic flights from London to most airports in the UK and they’re pretty quick once you’re airborne but the faff of getting to and from the airport and going through all of the security checks means it’s far quicker to get to most places by train.  So if I wanted to fly pretty, it would entail international travel and all that goes with that.  I’m sure that most of the major airports are used to gender variance by now but it’d be just my luck to fly to one that still sees any divergence from the photo in the passport by its holder as a major terrorist risk.  I’m also acutely aware that even if I was to be waved through the airport without incident, local opinions about TG issues in foreign countries may be different to the liberal attitudes that tend to pervade at home and if I did get into bother, would I be able to defend myself particularly given language barriers?  So why go to all of the hassle just to say that I’ve flown pretty?

So when I travel with the intention of indulging my feminine side, I restrict my destinations to the UK and go by car. For starters, it’s convenient.  I don’t need to consult timetables, I’m not at the mercy of cancellations and I don’t have a long walk from wherever I’m dropped off to the town centre.  There’s also a lot of reassurance from having the car nearby – it provides a safe haven in problematic situations such as when the shoes which seemed such a good idea on the way out are now making their presence felt with every painful step.  There really are no downsides to taking the car.

Well, that’s not entirely true about the convenience.  First of all, there’s the question of parking.  It’s not an issue in towns I’m familiar with but going to somewhere new is a different story.  If it’s a popular place, do I really want to spend time driving around looking for somewhere to park and then trying to download whichever parking app the local council has chosen to fleece its visitors?  And then there’s footwear; I can drive in heels but flats are generally safer which then means a change of shoes.  If I decide that boots are the order of the day, that means pulling them on and negotiating zips without losing any stick on nails or snagging my tights in the process.  And then there’s the environment.  Going into the outside world means breaking free from the closet, not taking it with you and whilst the car is a safe haven, sometimes it feels just a little bit too safe.

For me, the idea of leaving the car behind and travelling on public transport was not new, in fact it’s something that’s been knocking around my mind for over a decade.  And yet it always seemed like a bad idea.  I guess my biggest fear was getting onto a crowded bus or train and having to endure the ‘is she or isn’t she’ stares from other nearby passengers.  Worse still would be the risk of seeing someone who knew me – sitting on a bus or train, there’s nowhere to hide and an extended time for anyone who knows male me to study the odd looking blonde and put two and two together.  But eventually I came to the realisation that everything I do in my feminine guise seems like a bad idea until I actually do it.

The fears I had buying women’s clothes in drab were unfounded.  The terror I felt when I first stepped out of the house was without basis.  The fear I had that anyone who saw me would point and laugh when I first ventured out amongst other people were without substance.  The worries I had when interacting with sales assistants, baristas and waiting staff proved to have no basis.  The concerns I had that someone would approach me to ask for directions and then become speechless with shock when they realised my secret were groundless.  And so on.  Because the fact of the matter is that 25% of the way through the 21st century, transgender people are old news and most people have other things to worry about than whether the person they see is a ‘real’ woman or a man dressed as one.

And so, as I related last time, on a recent trip away from home I resolved to take the train from my hotel to the town centre rather than drive.  It was only a short trip each way – 3 minutes to be exact – but a 15-20 minute wait on the station beforehand.  And it was a wonderful experience.  Free from the confines of my car, I could enjoy being me from the moment I left my hotel until the moment I returned.   When a young man asked me which platform his train went from and I told him, he thanked me and set off with his companion; no laughing or shouts of ‘did you see the state of that?!’.  And when, on my way back at the end of the evening, another young man held out his hand to gesture ‘ladies first’, I smiled my thanks and that’s when it really sunk in.  I may know that I’m a very part time CDer but the rest of humanity just sees what they want to see.

Maybe, when I go out, I pass the ‘duck test’ – if it looks like a duck and quacks like a duck, then it probably is a duck – although I am realistic enough to realise that whilst I may look like a woman from several feet away, I most definitely do not quack, or sound, like one!  To some who see me, maybe I do look like the real deal, to others I’m undoubtedly not but I like to think that I do enough to at least have an air of ambiguity about me – or to put it another way ‘is she or isn’t she?’ rather than ‘he definitely is!’!  But whatever the truth is, nobody I’ve ever encountered seemed to care.

Taking the train was, to misquote Neil Armstrong, one small step for a man, one giant leap for A man da.  But it was like every other thing I’ve ever done on my feminine journey – no big deal.  And, in fact, those incidents along the way made it an exhilarating experience despite its brevity.  And that raises an interesting question.  Why should something that is so normal feel so exhilarating? 

I thought long and hard about that and, on a whim, decided to put the question to ChatGPT which responded with the following reasons:

– Authentic self-expression (often called gender euphoria): when your outside matches something true on the inside, the nervous system can light up with relief and joy.

– Novelty and courage: doing something new and meaningful releases dopamine. Stepping outside your comfort zone can feel electrifying.

– A hint of risk/rebellion: breaking old rules or expectations can create an adrenaline “thrill.”

– Anonymity of travel: trains are liminal spaces—lots of strangers, few lasting judgments—which can feel freeing.

– Sensory and embodied experience: clothes, movement, voice, makeup—engaging your body in a new way can feel alive and present.

– Social feedback (or the lack of it): being treated normally or kindly can feel validating.

– Life-stage freedom: at 64, there can be a powerful sense of “I get to be me now,” with fewer roles to perform for others.

That’s quite a list and one that encapsulates much of how I felt before the experience as I was planning it, during the outing and afterwards as I was reflecting on the whole thing. The idea of stepping out of my comfort zone to do something new was a powerful driver.  The anonymity gave me both the reassurance to do it and the feeling that I could just be another woman in the crowd.  The sensory feedback from the clothes (I was wearing a midi dress and heels) was a constant reminder that I was presenting in a way that gave me a profound sense of joy.  And perhaps the icing on the cake was the social feedback – being treated normally by the guy who asked for directions and with kindness by the ‘ladies first’ guy.

There’s clearly something profound going on here and the fact that ChatGPT seemed to sum up the whole thing so well suggests that many others have experienced the same highs that I did – after all, it’s not just plucking random concepts from the air but its training draws on the recorded experiences of others and this follows through into its responses. What’s particularly significant is that I’m not a woman trapped in a man’s body and I have neither the intention nor the desire to relinquish my male side to live the rest of my life solely in my feminine persona.  And yet everything I do in that persona feels utterly right and I experience feelings of calm and euphoria that just do not feature in my normal life.  I do feel lucky that, as ChatGPT asserted, I do ‘get to be me now’ and particularly lucky that feminine me can at least scrub up to the point where situations like this feel affirming and confidence building.

And that brings me full circle.  It goes without saying that walking onto a station, waiting 15 minutes for a 3 minute train ride hardly compares with either the rigmarole of flying or the sense of achievement that flying pretty delivers.  Flying requires interaction with officialdom, travelling on a train generally doesn’t and even if the train manager had come to check tickets, all they would be worried about is whether the correct fare for the journey had been paid, not the identity of its holder.

But there are similarities too. It’s not so much a step out of the comfort zone but an expansion of it.  It’s relinquishing the ability to have second thoughts, once we set off, we have no option but to follow through.  There’s no safe haven and if the situation takes a bad turn, we have to suck it up and move on.  But we are rewarded with euphoria whether it’s a three minute trip on a train or several hours on a plane.  A smile is a smile, whether from a security agent, cabin crew member or a train manager.  A simple gesture from another passenger is wonderful whatever mode of transport we happen to be sitting on.  And just making that journey whilst being who we want to be makes it all worthwhile regardless of how we happen to be travelling and while I may never get the opportunity to fly pretty, I can’t wait for the next time that I can travel pretty.  Who knows what adventures await?

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17 Responses

  1. Amanda,
    Great to hear from you again.

    Your elegant depiction of so much of what many of us think and feel is affirming. I love your phrases: profound sense of joy; affirming and confidence building; rewarded with euphoria; and making that journey whilst being who we want to be. I have personally felt all of that, but only after taking the steps to get out and about.

    Thanks for the encouragement. Your writing is always a joy to read.

    Love,
    Jocelyn

  2. Jocelyn, thank you for sharing your thoughts and for the compliments.

    It’s a strange feeling being out and about – no explanation is needed to those who experience it themselves and explanation is impossible to anyone who doesn’t. Taking the train rather than the car in many respects is nothing to write home about and yet I can still look back on it a couple of months later and realise how liberating it actually felt. Needless to say, it left me wanting more.

    Thank you for your friendship and support.

  3. Amanda,
    I read your post with great interest , you mention pushing the envelope even when the idea is crazy we still do it , WHY???

    I admit even now I still do it my cruise being the last big adventure , from the time I booked it I blew hot and cold about cancelling . My first biggy was the 127 miles on a Monday morning travelling down the A1 , M11 and M25 , I couldn’t believe it took me just two hours !! Next thought was my case being checked in , I’d taken the chance in packing spare boobs ( I’ve described before how I make them ) so I described quite clearly what they contained and how much in a note contained in the appropriate sealed bag , as it turned out it wasn’t a problem as I was sailing from Tilbury so the next time I saw my case it was waiting at my cabin door . I intend to post a full story but I will mentione a couple of points now . The waether was pretty bad so we made an extra stop at Greenock and more by chance I met my dining friends so we decided to take a train to Glasgow and toured the city in an open topped bus .
    During an easy day at sea I was sitting on a sofa in a lounge checking the daily program when a guy asked if the sofa was taken , he started to chat about the cruise but after a few moments leant foward and asked if I wanted to join him in his cabin . i politely smiled and said , ” no thankyou ” , then continued by saying , “I think one of us needs to go to Specsavers ! ” He mumbled something about missing his wife and ambled off .
    I had only returned for a week when I had my next holiday with my National Trust group on a coach trip to Bournemouth , after the poor weather on my cruise it was lovely to visit NT properties in warm sunshine with a lovely group of people .

    Next year I’m considering my first flight which should be a simple hop from east Midlands Airport to Jersey , I feel this would be a great way of trying flying without the problems of an international flight as the Channel Islands are part of the UK .

    I hope you understand I’ve mentioned these events as I had the same feelings as you , I can still recall the fear of my first drive out dressed and the gradual process of building my confidence to achieve my current situation . It’s just finding the balance of pushing the envelope to test the validity of your fears . I know how it feels to think the whole world is staring at you ready to point the finger and possibly bring your world crashing down . My ex-wife was the only person who tried to do that , it turns out the rest of society was on my side , they are either supportive or just don’t care as long as you don’t give them good reason to feel otherwise .
    Perhaps it’s easier for me because I’m divorced , in some respects I have no one to protect but then I have nothing to hide , everyone knows I’m Teresa so I no longer have fears of being outed .

    1. Specsavers!!! Loved it! I suspect that if Mr ‘Ladies First’ realised my provenance as I walked past him to get on the train, he’d probably be having similar thoughts, except about himself!

      On a more serious note, it’s human nature to have apprehension about entering the unknown and we can encourage those contemplating their own ‘giant leap’ with reassurance that our fears were groundless. But ultimately, it’s those apprehensions and fears that protect us by making us stop and think. A train journey just as the sun was setting around 8:00pm was fine but there’s no way I’d have wanted to do it at, say, 11:30pm when the pubs had closed. We also have to remember that regardless of how we live our lives now, we’ve never experienced a female upbringing where the dangers specific to girls & women are highlighted and instincts are developed.

      There’s a wonderful world to be discovered out there but we need to explore it with our eyes wide open.

  4. I totally agree with everything written but there is one area that I seldom see a word about–i.e. a crowded ladies room. this the only place a visit where I feel just a bit twitchy. Yes the stalls are private but when you wash up in a crowd there is eye contact through the mirror and women always 1-like to chat and 2 check each other out.
    Don’t get me wrong-this never stops me but I’m always aware of some put off gal throwing a fit. Would love to hear what others feel on this topic

    1. Emily, thank you for raising an interesting question.

      I have used the ladies’ room in the past but the recentish UK Supreme Court ruling now means that there are risks involved so I try to make sure that I won’t need to go while out en femme. However, I’ve got an ‘adventure’ coming up that pretty well guarantees that I will need to make that decision and regardless of what the law (or the SC’s interpretation of it) says, I will unhesitatingly use the ladies if needs be. However, out of respect for other users, I will be in and out as quickly as possible and will respond to any comments coming my way with a simple smile. We know that we don’t present a threat but I would never want to be seen as one by others.

      That said, the whole situation is inordinately messy, particularly for those in the UK who on the one hand have Gender Recognition Certificates which makes them to all intents and purposes their acquired gender in the eyes of the law but on the other are told that legally they remain their biological sex.

  5. Amanda,
    Since the UK Supreme Court ruling I have applied for a GRC , it does feel slightly superfluous as most of my documents already proved to them I am living as Teresa , they did warn me it takes many weeks , also they do point out its’ still not a legal document and if you read the small print neither are passports .

    Sorry but I also overlooked a second incident on the cruise . Most nights I would sit in a cocktail bar listening to the piano player while waiting for the second dining sitting . A guy leant forward from the far end of the sofa and asked if he could buy me a drink , I politely declined his offer and then out of the blue his Thai wife joined us , UMH ?? She was really lovely to talk to and despite her youthful looks turned out to be a grandmother , in the end we ganged up on him because he refused to wear a jacket and tie for the formal evening , he couldn’t argue with two women !!! So he did finally give in .

    Please try and not worry about court ruling over using women’s washrooms , it hasn’t made any difference , besides who’s going to enforce the ruling ?

    Emily ,
    You are possibly going to get more looks in a crowded ladies restroom because they had to wait for you , that’s the only time I’ve been glared out simply because they are desperate to relieve themselves , I do smile gently and whisper apologies .

    1. I’m actually in agreement with the SC ruling. Of course it’s messy but the alternative would have been even messier and put women at genuine risk. I’m going to carry on doing what I’ve always done and that’s to strive for the best possible representation of womanhood that I can achieve, given the hand I’ve been dealt. Ambiguity is my best friend in these situations – people may question whether I’m female but, in the absence of definitive evidence, they don’t feel sufficiently certain to challenge!

      1. Amanda,
        I’m not sure if I agree with you , it made the situation very difficult and worrying for both M/F and F/M transgender people .
        Many organisations were totally happy with the current law as it stood , unions had already negotiated workable practices .

        I was personally worried that it might create problems on my cruise and my holiday in Bournemouth , in both situations how could I appear to enter male toilets especially with my friends in the NT . Aside from that every single document had to be changed after my official name change , apart from the obvious passport and driving licence and banking , my house and car ownership , my voting registration and coucil tax , state and private pensions , my GP surgery and blood donations , not forgetting my will , in all it amounted to almost 30 changes . As I mentioned it makes my GRC application almost superfuous as I’m already living comfortably as Teresa .

  6. Amanda,

    It is always a joy to read your writing. I hope it is giving you the outlet you need these days so that you can continue to celebrate Amanda.

    Traveling as myself has literally been an important part of my feminine “journey.” Within England I have had important overnight trips by automobile, train and ferry to places as diverse as the Isle of Wight, Broadstairs and Ramsgate, Manchester, Colchester, Cambridge and Hereford (as well as Hadrian’s Wall, where I enjoyed the most delightful hike in the rain). I visited so many National Trust and English Heritage sights by car on day trips, I can’t even recite them all.

    I believe each of my trips helped me to find my “Lisa Equilibrium” — the place where I am most comfortable as myself, even though I came into this world with male plumbing and reproductive organs. I say “bullocks” on the High Court ruling and the TERFs (Trans Exclusionary Radical Feminists), including JK Rowling who apparently financed the case, as biology is complex and the ruling ignores the most important sexual organ of all — the human brain.

    Like Teresa, I have used a number of women’s spaces (bathrooms and changing rooms) since the ruling in the UK without incident. I live most of the time these days in a “Red State” (among the reddest) in the US, and have never had an incident using the bathroom for the gender in which I am presenting. Most humans honor the maxim, “live and let live.”

    One quick ladies room vignette, in keeping with the conversation, began with needing to use the loo during intermission at a West End musical. The queue was very long, and I was at the back. Everyone around me was anxious to get their business done before the start of the second half. There were only six stalls, and it took me especially long (no easy down with the undies, quick squat, and pee and she’s out of there for me!). There were still ladies in the queue when I finished my business and I did receive glares. My interpretation was “what took you so long,” not “what are you doing in here!”

    Thanks again, love, I enjoyed the banter as well the post.

    Lisa

    1. Lisa, thank you for the compliment and for sharing your experiences and views.

      I don’t want to say too much about the UK SC ruling (and it was a ruling on the interpretation of existing legislation, not a change in the law) as (a) I’ll probably get lynched for my views and (b) I’m still trying to write a post to try to reconcile opposing views. I’m also rather fond of JK, by the way!

      As I said in a reply above, the situation is messy firstly because it has raised more questions than it had answered and secondly because it effectively contradicts the premise of the Gender Recognition Certificate which is supposed to afford the holder all of the legal privileges of their acquired gender. But the alternative would have been to essentially pave the way for anyone to justify ‘bad behaviour’ on the basis of their protected status. Perhaps the worst example of this is the incarceration of sex offenders who offended while male but then ‘transitioned’ to female in female prisons which had already started in the UK.

      The other thing is the question of whether it has ever been acceptable under the law for a male to self-identify as female in some shape or form (i.e. without a GRC where there are gatekeepers to provide at least some rigour in the assessment process) and then access women-only spaces. The Equality Act gives protected status to ‘gender reassignment’ but, and I am happy to admit that I have no legal training on which to base this assertion, it would have been a stretch to claim that was all encompassing and covered any gender diversity such as crossdressing.

      In the end, the ruling puts the onus on us to be the best that we possibly can be. My gut feel is that except in very rare cases, providing we act with dignity and remember at all times that acceptance is earned, not demanded, it’ll be business as usual. After all, if we look like a woman, walk like a woman and generally act like a woman, it’ll be a very brave person that attempts to call us out. But those who seek to abuse the system, declaring themselves as a woman purely because they identify as a woman, now have the clearest possible indication that it’s game over for them.

      I shall draw a line under this issue for now!

  7. Lisa/Amanda,
    We all talk about our travel experiences , there’s no doubt it’s the best way of finding US , as Lisa comments , ” Lisa’s Equilibrium ” . It’s an envelope we can keep pushing as it can take us in so many directions , we can meet people and vist places we could only dream about at one time .
    Lisa , not only do I visit NT properties as an ordinary member but I’m also a member of a NT support group , we raise about £3,000 per annum and donate to Trust properties in our locality . I’m also on the committee to source speakers for our bi-monthly meetings , next year I’ve been asked to organise a coach trip to Oxburgh Hall in Norfolk . We also have annual holidays , I’ve been on three wonderful trips around the UK , next year we plan to cover Kent . Although the trust is very transgender friendly I really didn’t expect to be so involved , I admit my first holiday was daunting , it was the first time I’d spent almost a week away on a coach trip , again my fears were short lived .

    As for the Supreme Court Ruling , they should have never wasted public funds on such a poorly thought through case , to fully enforce its ruling is almost impossible and damaged so many lives in the process . It’s a situation where black and white ruling doesn’t work it needs sensible consultation and workable compromises .

  8. Hi Amanda,
    I was reading this as I am getting ready to go out tonight as Tanja. I really enjoy your articles and you share a similar view to many of the issues that face us particularly when to dress and not and the waxing and waning of the crossdressing Mojo.
    I am lucky in that my partner is aware and want to be involved and it was really her that pushed me outside the closet and encouraged be to go out as Tanja. However I have only been out with her, or in a group with her and two friends. We have been to plays, shows, night clubs, caberets and jazz clubs, and meals together. I feel confident with her and the friends and once out settle down even though it is debatable whether I pass. I feel the girls have my back.
    I would though be a bag of nerves if I went out on my own, especially in daylight to somewhere I was not familiar with, or travelled on public transport en femme alone. So I have great respect for you and others who do this. I don’t think it is something I could do.
    I am sure we will have a good time tonight and we are meeting one friend and going for a meal followed by a music lounge. By greatest fear is getting split up in a bar or walking back to the car.

    1. Tanja, thank you very much for taking the time to leave your thoughts and for your kind words.

      I’m very happy ‘flying solo’, so to speak (and it’s the same in my male life). That’s not to say that I don’t enjoy company but, for me, my feminine side is a very personal thing and whilst it could be argued that there’s strength in numbers, the more of us that congregate, the more likely we’ll be ‘read’! Of course, it was nerve wracking at first but over time I realised that careful choice of outfit – from the point of view of both appropriateness for the surroundings and comfort (particularly shoes which often seem only too glad to make their presence felt and not in a good way) – was critical to blending into the surroundings. I can still remember the buzz I felt the first time I realised that absolutely no one was looking at me. I don’t pass under any circumstances but make an effort with my appearance (unlike my male life!) and that seems to work for me.

      But that said, I have to confess to a pang of envy at your situation. It must be fantastic to just be treated as one of the girls and I hope you have a fantastic time tonight.

      1. Thanks Amanda,
        It was agreat night, and I am up early still buzzing. I thing you and other girls will no the feeling.
        Thinking back, I know I don’t pass at close inspection and the waiters in the restaurant and the door staff at the jazz club knew who exactly who I was but the treated me with absolute respect and in both establishments the other patrons just ignored us as three middle aged women out for a night out. What gave me most pleasure was waiting for an Uber at the end of the evening in a well lit place with others waiting for rides or goingvinto or from the city centre, and no one giving the two women ( one
        much taller than the other) any attention. It was a blissful experience and lovely way to end the night.
        I have the feeling to do it all again, but know I won’t dress again for a few months now and have that conflicted feeling that you and others have described following successful outings.

        1. Tanya, that’s wonderful. I’m so glad you had such a good time.

          To be honest, passing is overrated! Far more important is us showing that we respect what it means to be a woman and if we do, we’ll get it back from those we interact with as you experienced. Add to that the fact that it’s far easier to be nice to people than potentially cause a scene and we’re onto a winner!

          It’s a shame that you won’t be seeing ‘her’ for a few months but it sounds like you have wonderful memories to keep you going.

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