A bit of a disclaimer, if you're reading this post hoping for some shocking revelations that Isabelle is going to reveal about herself, then you're in for a disappointment because there aren't going to be any. What this post aims to do is attempt to lay out my thoughts as I try to uncover the reasons for why I crossdress. 

When I first started this blog back in Aug 2020, I wrote about a short post on why I crossdress. I likened it to a hobby that makes me feel beautiful, sexy, desirable, feminine and is a bit of a turn on. I did it because it makes me happy. While all of that still holds true, with multiple experiences of dressing out in public, talking to various people in the community, that short 3 year old post seems a bit dated and overly simplistic on review. It feels timely for a deeper dive into my base motivations for crossdressing. 

The easiest reason for why I crossdress is to attribute it to me being transgender. I don't deny that I am somewhere along the spectrum. But is the measure of how transgender a person, the extent to which one feels dislike/discomfort with the genitalia and male gender markers one was born with? By that yard stick I don't think I'm that transgender (if it can even be measured), although it could also be a case of being conditioned to feel ok with my male self over time, after years of suppressing. I've written about my struggles with gender dysphoria, that while I don't actively and continuously hate my male body, there are moments where the wish to have certain female traits rears its head. Like how great it would be if I have a nice pair of breasts that would let me pull of that dress with a plunging neckline. Or more delicate facial features that would let me pass much easily. I do have a great deal of envy for guys who have delicate facial features like those korean boy band singers. They really don't need to do much to be easily perceived as androgynous or female. 

I did consider whether I was gender fluid, enjoying flitting between male/female modes and sometimes blurring the two. But I find that my embrace of gender fluidity is binary; there is no in between. I am either decidedly male when in uncle mode, or unquestioningly female (dresses, skirts, stilettos, long hair, makeup, hippads, forms, the full works). My need to crank up my female "traits" to the max is so intense, gender fluid doesn't seem like the correct label. 

When I feel the urge to dress, I put on a full face of makeup and spend the day shopping or taking self-portraits. It's fun, but recently I've felt like the whole process was...pointless. For shopping, it felt like aimless wandering, hoping to uncover a special outfit that would make me excited (I'm usually unsuccessful in finding that special outfit). For self-portraits, it is still enjoyable and I like the final product, but after posting it on social media I usually get this weird sense of dissatisfaction. I check my phone repeatedly, feeling momentarily glad with each compliment before emotions crash down into a disappointing feeling of how meaningless it all is. What am I trying to achieve each time I dress up? To have people tell me that I am pretty, in order to validate my desires to be female and be the balm for my crushing insecurities? How many people do I need to tell me that I look good, will I be happy/satisfied? Because it feels like I will never be happy/satisfied. Am I an addict constantly chasing the next high? With so many of my bucket lists checked in the past year, I don't know what else remains. Cosplay and photography are currently a good avenue to direct my energies to sate the desire to be even better, since it is quite technical and my skills are amateurish. But I foresee that this will exhaust in time; and then what?

I've also been wondering whether my recent bouts of pensiveness is due to hitting a perceived "ceiling" in my ability to present as female. While I've never been better at my game, I'm left wondering if this is really the best that I can be? Because I still don't feel I am female enough, or good enough. (I sound like I'm going through a goddamn mid-life crisis). I can pour money and time into levelling up my skills in makeup, learning to style hair, getting the best wigs and even derma procedures to improve my skin. But this "ceiling" feels like it isn't just skill and product related, but physically limited. 

This however is quite a scary line of thought. Are my inadequacies and dysphoria nibbling away at my barriers to take the next big leap to break this perceived "ceiling"? Will I be satisfied only when I start taking hormones to make me develop female characteristics like budding breasts and softer skin? Or will crossing that line lead to me wanting to push the envelope even further with facial feminisation surgery to gives me a undeniably female face? Is a full transition the be-all and end-all? Will it be the point where I am truly satisfied?