Skip to main content

26th May - I didn’t take the opportunity to go dressed

My chance to go shopping presenting female came and I let it pass. 

It was late and there was a lot of traffic and I really needed to get home, but that is just an excuse if I’m honest. I didn’t want to. 

Although what I wanted or didn’t want is ambivalent in itself. I did want to because I wanted to test myself, gain some more experience. I also wanted to look nice and feel good about my outfit and to get a couple of other things to expand my wardrobe. I didn’t want to be conspicuous though, to expose myself to staring and judgments or to put myself at risk of transphobic abuse or attack. The latter is probably unlikely, but the fear is there all the same. 

It wasn’t just fear or vulnerability. The exercise felt pointless. I am continually swinging from feeling like I have to transition immediately to feeling that this is impossible and destroying my life for nothing and can never happen. When I planned to go, it felt like a step on the journey to transition. By the time the opportunity came around, transition felt like a fantasy that could never happen. Hence, when it came to it, why would I go through with my plan and make myself ridiculous and vulnerable for nothing. Naturally, the next time my feelings swing toward my need to be a woman, I will regret not having taken the opportunity. 

I seem to simultaneously hold two contradictory beliefs: that being a woman is my only hope of happiness; and that not transitioning is my only option to protect me from the unhappiness that would cause. This leaves me stuck where I am and still unhappy anyway. 

Maybe the logical thing to do would be to find a way to be happy as I am but I don’t know how to do that. 

I’ve been listening to podcasts about focusing on what you want and what will make you happy, how to make plans and organise your life to get there, that kind of thing.  I can’t get past the first step of any of them though: defining the goals or dreams or whatever.  I’ve got nothing. My only real dream is impossible. All the “standard” dreams seem pointless and don’t inspire me. Career, house, travel…what’s the point? 

Speaking with a colleague today, she was saying there is a world of possibilities. I don’t feel that way.  I feel that possibility was all in the past, there is nothing now but getting through the day to day because I am trapped by the life I have and the paths already taken. 

One thing for sure though, going shopping in a skirt is not going to solve any of my problems.


Comments

Popular posts from this blog

23 Sep 2025 - a handbag?

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...

27 May 26 - does my brain actually have a “girl mode”?

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...

21 May 2026 - a night out

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...