During a conversation with another sister, the topic of regrets came up. About the "shoulda, woulda, coulda" in our respective crossdressing journeys. Like all such conversations, they are tinged with a hint of regret.

As humans, we all have regrets. Perhaps a comment said too hastily or action done without sufficient thought that caused a relationship to breakdown. Or the consequence of inaction when time and youth were on our side, only to look back and wonder if things could have turned out better than it is now. If we could wind back the clock, other than buying a ton of bitcoins to make us filthy rich, I'm sure there are turning points in our lives where we wish we could undo or redo. In the context of crossdressing, many a times it is regarding that which was not done. Fear of the unknown holds many a crossdresser back from doing what we truly desire, be it coming out to friends in our youth, joining cosplay events, exploring one's sexuality, or even making that monumentous decision to take hormones and transition to full time womanhood before the onset of the irreversible effects of puberty.

I've wondered about what I would do differently if I could turn back the time. Broadly, I think I would have done these 3 things:

If I understood crossdressing better and was less afraid, I definitely would have created opportunities to dress up more when I was younger, and come out earlier, perhaps even in my teens. It would have allowed many experiences and a longer crossdressing runway. I would definitely have come out to my wife earlier (before we got married), which would have been fair to her. And during my exchange overseas I would have tried to live as a woman for an extended period (instead of sharing rooms with other Singaporeans).

Not necessarily to guy friends, but perhaps to female friends who would be more willing to accept and maybe even partake in the hobby. It would be fun to go out shopping with a bunch of girls who accepts Isabelle for who she is. And what better time to do so than during the schooling days, when one has no obligations other than do well in school and not run afoul the law. Maybe I could have even gone clubbing or the prom in girl mode.

I do have some facial acne scars, which were the result of genetics, poor facial hygiene and very itchy fingers. If my younger self had put in more effort, I'd probably enjoy much better skin now, which would allow me to use a lot less makeup than I usually do. I would also have gone for braces to get a perfect looking smile as well. 

Another aspect is how muscular I got in army. Although it was a great confidence booster as a guy, the large number of chin-ups made my deltoids a bit too disproportionate for a woman's typical body, which makes me avoid spaghetti strap outfits like the plague. I can do the fitspo look very well now though, and occasionally look to local influencer Jamie Pang for inspiration, whom I seem to share the same body shape (minus the hips of course).

 

If I'm brutally honest with myself, I sometimes wish I had both of these when I were younger, although it might really be a rose-tinted fantasy more than anything. Even if I didn't live as a female all the time, being more feminine would be a boon when switching between the guy/girl mode. The permanent effects of hormones however do turn me away quite a bit, especially the chemical induced sterilisation, which mean no kids of my own.

With regards to my crossdressing journey, I think I don't have too many regrets (Can't be said for my life in general, but that's a different story). I think coming out to my wife and her acceptance, at a point in my life when I was still reasonably young and able to dress up to try out new experiences was pretty important in allowing me to check off my crossdressing to do list. Also, whatever I have done (or not done) in my youth were decisions made based on knowledge, emotional state and at that time. 

Like all regrets, it is good to think about them briefly and what should have been done, before casting them aside and moving on. As much as possible, the past should not be a spectre haunting the present and holding back a better future.