I was recently chatting with a newbie crossdresser who commented that she came out to her friends recently, who turned out to be very accepting of her gender fluidity, positive vibes all around. But she also read my blog and had wondered if she was too daring to take such a big risk. Of course she was already out to her friends during a dinner and dance event, so any potential worries about being too open was well, moot. She was in her early 20s, so she attributed the difference in risk tolerance level between herself and what I seemed express on this blog to be a generational thing.

Damnnnnn. 

Your girl Isabelle is old. No offence taken from the conversation of course. But it was interesting to hear that perspective. The newbie crossdresser had already attended Pink Dot SG, got support from her female friends (and some male ones), and was all ready to explore her female self. She did not strongly identify as transgender (at least not yet), so in terms of the mindset and need to be recognised as female, I'd say she is considered to be a crossdresser. The willingness or the feeling of readiness to come out this early certainly did not occur to me when I was her age. Back then, I was all ready to keep this secret to myself and take it to the grave; a scared crossdresser in her room wishing to set her inner girl free but too worried about the implications of letting the world know. To this day, other than my wife, nobody else knows. Granted, this situation is of my own design, since there isn't really any great reward if I let others know about Isabelle (other than seeing their amazement).

Of course, the internet was fledgling back when I was in my 20s, smartphones weren't really a thing yet and online shopping only just started. There were some resources on the internet for transgender folk but very limited. 

So there is a generational gap. Quite a number of crossdressers my age are still in the closet, whereas the younger ones seem to be exploring their female selves in public and coming out to their friends at a much earlier stage. There is definitely some bias of course; we are only aware that someone is out of the closet when their social media presence reflects as such and not everyone is so open on social media, so statistically speaking this observation cannot be verified. Nevertheless, I think it is definitely a fact that members of Singapore's LGBTQ+ community, crossdressers included, are coming out at a younger age. The internet has showed that our "condition" isn't unique and it is ok to be a bit different from other boys and men.

Now more importantly, with this realisation that I am a product of my era, other than attempting to look hot and lean into the MILF vibe, how is an ageing crossdresser going to stay relevant? Hmmmm