This was mainly intended as a basic date record for myself, as a good format for keeping tabs on how things have changed, and remembering to take the long view. Then I started filling in the older, sketchier trans-relevant events, and, as so often happens when I write something, it just started getting silly. :)
1999: Records begin. Earliest recorded discussion of trans issues implies that this is nothing new, that I've already been thinking about it and airily concluded that yes, I am a transsexual (although apparently this is distinct from "yes, I am a boy", since I didn't feel compelled to do anything about it and was largely content to live my teenage years as a girl, just a weird eccentric girl whom nobody really liked and none of the boys wanted to go out with. But then I didn't really get out much, so the concept of "social" transition wouldn't have struck as much of a chord with me as the prospect of sitting at home writing very long journal entries in which I painstakingly deconstructed my transness of self).
1999-2006: mostly spent badly cutting my own hair whenever it passed 3 inches, wearing baggy t-shirts, refusing to shave my legs, feeling rebelliously pleased every time children tried to insult me by insisting I was a boy, and recording trans documentaries off the telly. Oh, and writing very long journal entries. Meanwhile, real life continued, and when I occasionally paid attention to it I seemed to be a girl, but then again I found so many aspects of real life completely bewildering that I didn't really worry about much of it.
c.2004: discovered the "open overshirt/baggy t-shirt" combo and stuck with it for the next 5 years (occasionally venturing into "open overshirt/fitted t-shirt" once I'd realised all my baggy t-shirts were a bit shit).
2006-08: a period of confusion in which my rarefied hypotheses about myself finally came into earth-shattering contact with Friendly Other Beings and I was too busy rapidly learning to socialise (and learning that I did it quite well, even some aspects of being female) to do anything other than intermittently mumble to myself "but I didn't think I was a girl..."
2008-10: still vaguely thought of myself as genderless, but didn't do anything about this, because I didn't realise other people didn't think of me as genderless :) (come on, guys, wasn't it obvious? ...wasn't it? ...guys?)
Early 2010: finally started doing some proper thinking, and began to publicly identify as genderqueer.
(May 2010 was, I believe, the last time I non-ironically wore a dress. It wasn't particularly enjoyable. Particularly when the well-meaning drunken male companion I'd met for the first time that evening told me "if I weren't mostly gay, I'd probably fancy you myself", and I kicked myself for having decided to present as female rather than any of the other more comfortable but more sidelong-glance-drawing ways I'd considered dressing. Um, not that I fancied him particularly; just that I enjoy fucking with people's heads.)
September 2010: began to use Spivak pronouns.
October 2010: impulse-bought some crepe bandage and started binding on special occasions.
New Year 2010-11: first extended public experimentation with identifying as male.
February 2011: began to use male pronouns (experimentally, alongside Spivak according to mood).
August 2011: bought my first proper binder!
26th September 2011: came out as trans* to work colleagues, and started using a male name at work.
2011-present: am FAABulous. Still regularly wear the "open overshirt/baggy t-shirt" combo (it looks less shit when there's not a couple of lumps in the way).
1st January 2012, ~0030h: accidentally resolved that this would be the year that I start trying to access testosterone therapy.
5th March 2012: appointment with GP, in which I ask to be referred to a Gender Identity Clinic for eventual hormone therapy.
30th April 2012: appointment with psychiatrist for pre-referral evaluation.
10th October 2012: first contact from Gender Identity Clinic (asking me to fill out a registration form to confirm I still want to go ahead...)
16th March 2013: first treatment-related letter from Gender Identity Clinic.
2nd May 2013: appointment with Gender Identity Clinic for initial assessment.
6th September 2013: appointment with Gender Identity Clinic for second initial assessment.
17th July 2014: appointment with Gender Identity Clinic to check I haven't become any less suitable to discharge since the last appointment.