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This is the best explanation, anywhere, that I've found of questioning one's gender and the very feeling of being trans. It comes from a discussion at Oasis and is written by Cam, a very cool guy from New Zealand.
What it's like:Posted by TransboiCAM on Saturday, 02/01/2003 - 15:33.
It's hard to describe what its like to question gender(I feel a story emerging from this one, LOL). Kinda a bit like questioning your sexuality but on another level.
Society is totally geared for two genders, male and female- being male born men and female born women- and it is initially terrifying to realise that you don't fit there (bit like realising you're gay, again)- and then to realise you want to change genders...
It's like as a little kid, putting your shoes on the wrong feet and trying to walk- you think they're right, others don't...and they don't quite fit right, but yet they look right to you. It becomes frustrating, trying to force yourself to be something you're not just to fit in with society and then to come out and acknowledge that you are different and openly question, want to change or live as another gender and face discrimination from society, both gay and straight- because they feel you're not like either of them and you make them uncomfortable because you're so different from the "normal" male born men and female born women they see everyday.
Being silent as a torn scared child out of confusion because you've just been yelled at for doing something gender inappropriate and seeing what the consequences of that are, yet it feels so right to you, and being able to work out what's so wrong about it.
Being incredibly frustrated because of not knowing who you are, being surrounded by people who don't understand, a lot who are ignorant and enforcing their two gender binary that doesn't change for them- people thinking you're sick, or crazy to question gender.
Feeling trapped in a deep dark hole or running round in a maze with no end, not knowing how to get out, and find the path or light and feeling stuck with nowhere to go, no one to talk to, and no answers, and desperately searching for other pieces in the puzzle, round and round in your head.
Coming out as gay, then realising later that you don't have all the puzzle and may be trans/are trans is quite hard too (particularly in my case, coming out as bi as well as trans)- get a lot "So you were never really gay!"- and people getting annoyed with me because they can't fathom that I wasn't trying to deceive them, I truly thought I was gay, but there was just something there that didn't fit right for me and it was just a step on my journey to acknowledging my true self...and I may still be on that journey.
Don't know if that helped at all or I was just rambling- let me know.