This is a post that I never in a thousand years thought I’d be able to write. For the best part of half a century, I was closeted, either dressing in secret or, for stretches of years at a time (with one stretch lasting 18 years) toughing out the urges without going anywhere near feminine apparel. But as regular readers here will know, things are very different now and ‘living the dream’ just doesn’t do things justice – what I’ve experienced has gone way beyond my wildest dreams.
I recently dipped into Femulate and way back in 2017, one of Stana’s contributors posted a list of her best moments when out as a woman (http://www.femulate.org/2017/06/best-moments-out-as-woman.html). And with this in mind, I thought it would be fun to do a countdown of my thirteen best moments loosely ranked in order of their impact they had on me, saving the best till last. I’ve also added links to the posts where appropriate if you’d like to read more about each experience.
13 The Lift/Elevator (Getting A Sense of Perspective).
I’d had a lovely outing to a local town for a bit of browsing and refreshments at the Caffè Nero and it was time to go back to the car for the drive home. Up to that point, and even when I’d parked a couple of hours earlier, I’d been nervous about being seen by the population at large and would try to avoid being at close quarters to others by keeping my head down and facing the wall. But as I waited for the lift to arrive, I realised that nobody cared who or what I was and when we all got in, I happily turned to face everyone. A woman looked my way and smiled and I smiled back. No words were exchanged, just smiles, and in less than a minute, we were all going our separate ways again. But for that brief moment, I felt a true part of society for the first time and that feeling has never gone away.
12. After You
The early days weren’t easy and whilst legitimate trips away from home (i.e. those where I had a genuine reason to be away) provided an ideal opportunity to pack for two, so to speak, the emergence from the hotel room was nerve wracking to say the least. The problem was that I was scared that anyone who saw me would make the connection with the slightly scruffy bespectacled guy who’d checked in an hour or two earlier so it was a case of take a deep breath, head down and hope for the best. On this particular day, the cleaners were hard at work and as I arrived at a door in the corridor, a male cleaner arrived from the other direction at the same time. And being the gentleman that he was, he held the door open for me to walk through. I responded with a smile and a whispered ‘thank you’ and that was that.
11. You’re Very Brave (One Last Try).
When a sales assistant told me I was very brave, I could have taken it in one of two ways – either I was brave to confront my struggles and present as my ‘authentic self’ or I was brave to walk around in public as a man in a dress. I like to think it was the former. I’d just gone for a browse in a shop and the assistant behind the counter, a woman of around my age, gave me the biggest smile and asked me how I was. After I left the shop, I felt compelled to return and thank her for the welcome she’d given me and during the short conversation that followed, she told me that I was very brave. It was the first time I’d ever experienced genuine acceptance and it felt wonderful.
10. A Smile Says It All
I’d only just got out of the car and was walking towards the shopping mall. A young woman coming in the other direction looked my way and we exchanged smiles. That’s all. Nothing more. But it was a genuine moment of warmth and in that fleeting moment, I knew that I was going to have a good day.
9. Ladies First (The Highs and Lows of Life).
Before mid-2025, my outings had always been by car but on another night away from home last August, I thought it’d be fun to travel by train. It was only one stop and a four minute ride from my hotel to the sea front but a liberating experience all the same. After a lovely evening out, I’d made my way back to the station only to find out that there wasn’t a train for another 20 minutes so I just sat down on a bench and waited. As the departure time approached, a few more people arrived so I decided to hold back when the train arrived so that they could get on first and I could find a seat away from them. However a young guy out with his girlfriend/ wife had other ideas – he pressed the button to open the train door and then turned to me, smiled and gestured for me to go first. Maybe he’d been well brought up or maybe he just wanted to check out the ageing blonde in the stilettos (or maybe he should’ve gone to Specsavers) – I hope he wasn’t too disappointed when I walked past him and smiled.
8. I Like Your Boots (The Homecoming – 2 – True Acceptance).
Whilst my Amanda times are about as far from my normal life as it’s possible to get, there is something common to both – I need to eat regardless of how I am dressed. Feeling hungry, I’d gone to an outlet village where I knew there would be plenty of places to get a meal but as I walked around, I started to get cold feet. I’d chickened out on a previous outing and ended up at McDonalds but this time something inside me told me to persevere. I finally found a Lebanese place – not a cuisine I’ve ever felt the need to try but my feet were aching so I took the plunge and asked for a table for one. The waitress, whose name I later found out was Fin, led me to a table and then exclaimed ‘I like your boots!’ and that set the tone for the evening which ended with what I can only describe as a tender woman to woman conversation. It was the first time I’d experienced anything like that; whilst my provenance was never in doubt to Fin, she just treated me the way I’d always wanted to be treated.
7. I Love Your Nail Colour (Living The Dream 3 – The Adventure Continues).
I’ve been on the receiving end of this one twice – once in a museum gift shop and once in my favourite Caffè Nero. The nail colour in question was not applied by me but the colour the bulk plastic stick on nails I got from Amazon came in (240 nails in an assortment of sizes for less than £10) – an expensive manicure this definitely was not. I know that both of the lovely women who paid me this compliment knew exactly what I am, I know that they said what they said to show that they were allies but both made my day and proved that acceptance can be shown in the most unlikely of places.
6. There’s Nothing Like A Good Moan.
I am British. We moan a lot. It’s just the way we are. As my confidence grew, I found myself completely happy talking to staff in shops, cafes and restaurants but let’s face it, they’re paid to be nice and would probably lose their jobs if they were anything other than polite with me. The public at large are a different proposition, though. I’ve seen several smirks and scowls as people have looked my way and so I’ve tended to try to avoid contact with random people in case the other party decides to make their disapproval of trans people in general and me in particular abundantly clear. But standing in a queue for a car park pay machine (we Brits queue a lot too), it quickly became apparent to both me and the woman of a similar age to me in front of me that the person at the front was fighting a losing battle with the machine, getting nowhere despite several tries and clear onscreen instructions. After a mutual eye roll, we immediately bonded with a good moan about how long it was all taking. And with that, yet another dragon was slain.
5. It Still Looks Cute
I was walking through a shopping mall and approached one of those promotional stands. A young woman was handing out samples so I took one not knowing exactly what it was. She then asked me if I wanted her to do my hair which was when I realised that the sample was a hair product. I looked at her not knowing quite what to say at which point the penny dropped and she said ‘oh, is it a wig?’. I confirmed that it was and she replied ‘oh, OK, it still looks cute though’ and said I could keep the sample anyway!. Let’s be clear, I know that I don’t pass in the literal sense of the world but that brief interaction suggested that I was somewhat closer than I previously believed (or at least my hair passed even if the rest of me didn’t).
4. I Love Your Lipstick Colour
After my trip to central London in February 2026, I decided to stop going out – the risks of discovery were too high and with Mrs A’s impending retirement, I wanted to scale back my activities in readiness for the conversation about the way forward. However, in May my daughter went away for the weekend and it seemed too good an opportunity to miss so I put on my glad rags and headed for my usual shopping mall, Bluewater, which is around an hour’s drive from home. It was a Saturday and busy so the sales assistants and baristas didn’t have time for small talk. After a couple of hours, my legs and feet started to tell me that they’d had enough so I made my way back to the car a little disappointed that I’d not had any memorable encounters. But all of a sudden a woman in her fifties wearing a lanyard and promotional T-shirt stopped me. In my normal life, I’d just have kept walking but I looked at her expecting to be introduced to the latest ‘must have’ product from a pop up stand but was rather surprised when she said that she loved my lipstick colour and asked where I’d got it. I retrieved it from my handbag and showed it to her and after examining it, she thanked me adding that she loves a red lipstick. She then disappeared into the mass of other shoppers.
I’m still at a complete loss why a random woman would stop me in a busy mall to ask about my lipstick but it did make my day.
3. I Bet That Would Really Suit You (A Question of Acceptance – 1 – Another Milestone).
In recent months, I’ve aired my concerns about entering female fitting rooms but that doesn’t mean that I haven’t had wonderful experiences in one of the inner sanctums of femininity. I’d tried on a black jumpsuit and cream fur jacket in River Island, Bluewater and was on my way out. Now the fitting room lighting in that store is off the scale amazing and could make anyone (including me) look good. As I left, the fitting room attendant asked me how I’d got on and after a quick chat, she looked at the fur jacket I was holding and said ‘I bet that would really suit you’. And thanks to River Island’s fitting room lighting, she wasn’t wrong! The complete ordinariness of the exchange was what made it special; it didn’t feel like a conversation with an unspoken ‘I know you’re trans so I’m going to say something to make you feel good’, just a conversation that was completely relevant to the surroundings and situation.
2. Do You Want Me to Apply Some? (A Question Of Acceptance – 3 – This Time I’m Happy!).
I only approached the MAC consultant in Boots the Chemist to ask for advice on a good eyeliner for the waterline that would be easy to wash off. I never expected to be sitting in front of the mirror in the store having it applied. But that’s exactly what happened and an innocent question became a truly emotional moment as I realised that I was not only being spoken to as a woman but treated as one too. And while £17 for a kohl pencil (reduced from £20) was bordering on exorbitant, it was worth every penny for both the quality and for the experience.
1. You Do Look Amazing (Living the Dream 2 – The Time Has Come).
I’ve always loved what we in Britain call court shoes and in the US are called pumps, particularly those with a stiletto heel and pointed toe. In my corporate days, I used to while away the boredom of commuting by seeing how many women I could spot wearing them which in 1990s central London was plenty. There was therefore an air of inevitability that they would form the basis of my closeted crossdressing accompanied by hosiery and a nice tailored bodycon dress. But their elegance was not matched by practicality and as I checked myself in the mirror, there was always a feeling that I was all dressed up with nowhere to go. And even when I stepped out of the closet and into the real world, I gravitated towards more casual outfits and so the bodycon dress and stilettos seemed destined to remain hidden in perpetuity.
But then the opportunity came to book and check into a hotel as Amanda and a hotel with a restaurant was chosen. There was never any doubt in my mind what I would wear for dinner and I’ve never felt as good as I did when I stepped out of the hotel room in my black bodycon dress and stiletto court shoes with a cream pashmina over my shoulders for warmth. As she showed me to my table, Basma the waitress complimented my outfit. At the end of the meal I thanked her again and told her that what she said had really made my day. She said ‘no problem’ then added ‘you do look amazing’.
I still get the most wonderful warm feeling whenever I think about that moment, even several months on. I’ve been on the receiving end of several compliments when out & about and I’m well aware that most are made to let me know that it’s OK to be me. And perhaps Basma’s first compliment – a simple ‘I like your outfit’ – had the same intent. But the spontaneity of her second ‘amazing’ compliment felt sincere – she said it without thinking, she didn’t have to add anything to the compliment she’d already paid me and it was a compliment about how I looked in the outfit, not just the outfit itself.
I couldn’t have asked for anything more.
-o-O-o-
As I said at the outset, all of this has been way beyond my wildest dreams. The idea that I would ever have the guts to leave the house dressed as a female, let alone walk amongst other people was fanciful to say the least and the idea that I would experience widespread acceptance was too far-fetched to even consider a possibility. But what’s even more surprising is how much I’ve changed. When taking my first faltering steps, I hoped that I wouldn’t see anyone and would freeze in terror if I spotted someone in the distance. And even when I started to travel to places where other people would be around, I hoped they’d look the other way. But nowadays, I’m not only happy for people to look my way but I positively enjoy engaging with them.
What’s perhaps most surprising is that there’s no hidden secret. I don’t pass and whilst I take a lot of care with my presentation, in the eyes of others I will never be anything other than what I actually am which is a female presenting male. To some people that’s enough to prompt disapproval, intolerance or even hostility but the fact of the matter is that ‘some people’ are a tiny minority in a vast sea of decent human beings happy to respect others’ rights to live as they choose. If I do have a secret weapon, it’s smiling but it’s difficult not to smile when blissfully happy. I always start every encounter with a smile; sometimes I just get an expressionless look back but more often than not, the smile is returned and it sets the scene for a wonderful encounter along the lines that I have related here. And I also try to live by Kandi’s rules of the road – be smart, appropriate, confident and visible.
For most of my life since the fateful day when I tried on a pair of my mother’s tights in my mid-teens, I have wished that all of this would just go away and I could be a normal guy. I tried many times to rid myself of the scourge which nearly blew up my marriage and has often made my life a misery. And yet now it’s the exact opposite; life without Amanda is inconceivable, at least for the time being, and the wonderful people who inspired this post have played a huge part in that. Each one of them could have given me the expressionless look back before mumbling the bare minimum to get the transaction over and done with but they didn’t. Some saw no difference between me and any other female presenting person and treated me just the same. Others obviously saw a big difference and gave me special treatment to let me know that it was OK for me to be me. In the end it doesn’t matter; they made me happy and I like to think that I perhaps made their day a little better too and that’s a win-win in my book.
