Maiden’s Journey

I had an overnight in London and so had the opportunity to go out presenting female to get some more experience. It went fine, but afterwards I’m feeling really down and this huge wave of dysphoria that I can never be the woman I want to be.  My last outing in London had been a success, and I had a really fun night, was treated as a soma by people I met and felt euphoric afterwards. That was a night out at a bar and lots of drinking. This time, my evening was already committed so I would be going out in the morning before work.  A year or so ago, I had gone to breakfast in the hotel wearing a dress and it had been an uncomfortable experience. I was conscious of people staring, some old man walked away from the queue rather than stand next to me, and a young woman and her boyfriend openly laughed at me in the lift.  I wanted to put that experience to bed so I did the breakfast again. After last time, I was nervous. Walking around town dressed I find most people don’t notic...

In spite of knowing that I am transgender for many years and having occasionally visited a couple of queer bars in London, I have never actually had a conversation with another trans woman.  I’ve connected with quite a few people online and there is community there, but in real life, never.  It isn’t that I have never encountered a trans person. There are certainly trans women around, but it isn’t as if I could go up to a stranger and ask them stuff, not to mention the implied rudeness of having “clocked” them as trans in the first place and then felt that gave me a right to speak to them   I had hoped that by going to a queer bar known to be trans friendly, I might meet someone, but that hasn’t happened, although I have only been three times   When looking for possible support groups in my area though, I have discovered that there actually is a trans and non-binary meet-up in the city where I work!  This is my opportunity to meet people in a similar situation. ...

As I keep reflecting on my night out as Nicola last week there are a lot of questions and ideas that are swirling around in my head.  One is, whether my brain has a “girl mode”, because I felt so different and behaved in ways that were unfamiliar to me.  The really distinct difference in how I felt this time was that I didn’t feel like I was a man in a dress at all, I just felt like me. I remember thinking that this is what it is like to be “inhabiting womanhood”. Evidently I have ridiculously pretentious notions after a few drinks, but it was what I was feeling. This is what it is like to actually be a woman. Less pretentious.  An odd thing, but one which does make me wonder if my brain has some kind of “switch”, is that I looked at women differently. I am exclusively attracted to women and I am attracted to boobs and bums as much as the next man (cringe at associating with being a man). I know it is impolite to stare at a woman’s chest, and I make a conscious effort no...

Having a night on my own in London, I wanted to go out presenting female and get some more “real life experience”.  I had drinks and dinner with some colleagues early evening and to be honest had already had too much wine before I went out later by myself. This probably helped my confidence, although not my coordination with nail polish and mascara, which were a bit slapdash to say the least.  I remember last year getting in a lift in the hotel in a dress ready to go out, and being self conscious of people staring at me. This time, didn’t give it a thought. Likewise going into the underground and being on the train with other people. I didn’t notice if anyone looked at me and nor did I care. I was just me being me and wearing a skirt didn’t feel like a Thing, I wasn’t conscious of my clothes at all.  Similarly walking through a busy Soho to the bar, I just felt like I normally do walking around town.  Got to She Soho. Amazingly the bouncer asked me for ID. I’m 51...

I could see 2025 as a failure.  After all, I started the year with the intention to begin my transition. I still haven’t started.  I made initial contact with the endocrinologist clinic about feminising hormone therapy, but then didn’t progress that at all as soon as I encountered the blood test hurdle.  Here at the beginning of 2026, I am no closer to living as a woman than I was at the beginning of 2025. I have not come out to anyone, I don’t have a hormone prescription, my body is still male, my presentation is still full time male, everyone still knows me only as my male name.  Has the longing to be a woman gone away because I haven’t done anything about it? No. Obviously.  Although I have not begun transitioning, I have achieved a couple of things this year.  One is that I survived my wife catching me out and finding a pair of knickers that I had forgotten to hide. It was awful, and she was terribly upset, but I got through it and that is somethi...

The first time I went out dressed female was a huge thing just in itself. It was a test for me to see if I had the courage to do it.  It was also a completely new experience and I didn’t know how people would react or how I would feel about that.  Having done just being visible, I realised that I could cope with it which was good, but it then didn’t achieve anything, so I needed to interact with some people to see how they responded to me as a non-passing person with a voice that confirmed my sex even if my face hadn’t already given me away. I found that I could pass this test too. Even if it was obvious that the people I spoke to (shops and coffee shop staff) saw me as a man or cross dresser or whatever, I was okay. But then I felt that these interactions didn’t count because they were strangers so why would I care what they thought anyway.  That’s why I next needed to try being Nicola with a friend, to see whether I could handle it with someone I knew and whose opinion...

It was exciting to be out but lots of feelings, good and bad For one thing, I felt bad about lying to my wife about where I was, and for even doing it which is a sort of betrayal (even though it’s not) I did feel good about how I looked though. Admittedly due to padding very tight shapewear, a slinky dress and a wig and makeup (ie almost entirely fake!) but I felt actually sexy, long legs and curves and all. London is very different to where I live. It’s so anonymous that nobody gives anyone a second glance. I went through Paddington station, travelled on the underground, walked down a packed Oxford Street and was invisible. Or “passing as female” maybe. London is so diverse anyway that men in femme clothing or heels or anything really is just about normal. The door staff at the women-only bar were happy to admit me, one of them called me “sweetie”. So I guess femme enough Then it got less fulfilling. For one thing, it was very quiet in there; a bar / club with only four people in is n...

Although it was good to have been able to go out and be fully visible as Nicola, it didn’t really achieve anything.  I’m not sure what I expected to achieve to be honest, but whatever it was, it didn’t.  Maybe I was hoping to be able to make a connection with someone, ideally another trans woman and to hear about her experience of transition, but there was no trans woman there. Alternatively, speaking with a cis woman about her experiences and learning from her about how I can better present as female. Unfortunately, being too shy to speak to anyone, this didn’t happen. Not just shyness though, I also felt unworthy to speak to anyone as “not a real woman”, why would anyone want to talk to a “man”, presumably having gone to a women-only bar to avoid just that.  What would I have done if a lesbian had shown any interest anyway? I don’t have any desire to cheat on my wife so I’m not up for anything. Even if I were, it isn’t as though I could, because underneath all the sh...

I have been experiencing a bit of a rollercoaster of feelings this weekend. Well, not just this weekend, but even more so than usual.  As usual, I am bouncing between “I want to do this” and “I can never do this”. All the time. There is no way of taking a step forward. But also, there is no way of giving up the idea of transitioning. Both are impossible.  I have shaved all my leg and body hair growth off again which makes me feel better and a lot less masculine and dysphoric. I am still male though. I can make my legs look feminine and I can put on female underwear, but there is no doubt from the shape, that I am not a woman.  There was a young woman I saw yesterday and she was likely unaware that I even saw her, but looking at her made me feel bad. I wasn’t attracted to her particularly, although she had beautiful hair, but it was her shape that upset me. Maybe it was because she was wearing a tight stretchy top and baggy jeans that emphasised it, or that she had an espe...