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In about 1988 I bought a secondhand Raleigh Montage off a mate for £150. Think it might have been a 24" frame (I now ride 17" or 18").
My mates and I started off riding round the wooded bits of the local parks, taking it in turns to hit the bombholes as fast as we dared - then ventured further into the local woods - of which we were lucky to have a lot, considering we lived so close to London.
I was wearing a C&A ski jacket, jeans and trainers most rides I think, no helmet of course. Then bought some magazines and realised we were getting it a bit wrong, got a train to London and stocked up on cheap roadie lycra and one of those Specialized polystyrene helmets. Picked up a set of toeclips from the LBS/motor factors.
Next came another s/h bike that actually fit me (Giant Coldrock with Deore and Exage bits IIRC), then shortly after that as I really got into it my first new bike - a 1991 or 1992 Saracen Kili Flyer in "deep purple" - fillet brazed Prestige with Deore groupset - which I started racing when a local series (Marshalls) sprang up in the mid-90s.
It was nice to have been around near the start of it in the UK and to have seen it grow since, but I am a bit envious of youngsters today who can pick up an awesomely capable lightweight FS-er secondhand for way less than that Saracen cost me in real terms.
2010 with my sons riding Swinley Forest with Palmer Velo on an Airnimal Rhino. Next came a rigid 29er SS then finally a 26er SS hardtail. Both steel. Teen1 rides a Giant Anthem, which happens to also be my size but not my taste. I commuted and rode road forever, but mtb had to wait for location and age of kids.