Maiden’s Journey

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...

Now that shorts season is behind us, and my legs will be hidden by trousers for the next six months, I am free to shave my legs.  I had a brief window of opportunity when my wife was out to get the clippers out and remove the long hair from my legs, chest and tummy. Unfortunately I can’t reach my back to do that, but can do my shoulders at least. And when I say clippers, I mean the dog grooming clippers, which I have found to be the best thing for clearing leg and body hair growth. Lucky I never balded the dog, because they’re pretty effective.  Seeing myself hairless is lovely. My legs go from male to female instantly and I love it. Hair definitely triggers some dysphoria. It will be easier to wear tights when I next get the chance to go out dressed female. Plus, tights will feel nicer to wear too.  Looking at myself in the mirror wearing a crop top and matching knickers with no body hair and shaven legs, I felt so much more feminine. If it weren’t for the unsightly shap...

With the help of my padded bra and padded shorts, I am able to give the illusion of some female curves or to put it another way, “tits and ass”. Because they are just padding though, they don’t move like the real thing, there’s no jiggle or squish.  I was traveling in London today and so was surrounded by many more women than I would normally see, which has made me feel more envious of what I don’t have.  There was a woman on the train wearing a black stretchy ribbed dress that is similar in shape and style to one I have. Her hips and waist and the shape of her bottom were so very feminine. I would love to have a shape like hers. Maybe by taking feminising hormones, I would be able to have a more rounded and feminine bottom, although I can’t have the hips as that is fixed by my bone structure.  There was another woman at the station wearing leggings and again, I was envious of the shape of her thighs, her round bottom and the curve of her tummy. Through feminisation I cou...

I have not been out presenting female in public for about six months which is a long time.   The last time was my trip to London when I went out to the bar and dinner, which felt great, and to breakfast in the hotel which was less successful. At that time, I felt confident and like I could do this.   Following my wife catching me out with some of my underwear, I cut my hair, put away my clothes and didn’t do anything for a while. It seems my confidence got lost in that too, because when I started thinking about going out dressed again, I felt really nervous about it.  Probably doesn’t help that the anti-trans lobby had successes during this time and it feels a less safe thing to be doing now than it did six months ago.  Whatever the reason, I was pretty scared this time.  The biggest mental hurdle is around changing from male to female clothing, as I have to leave the office and arrive at the mall in male clothing, then be back in male clothing to go home so...