Second bike?

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Once you get really comfortable on your bike, you should be able to move up. You just need the general skills, and then you will have to practice when you get your new bike. I still ride my 250, but I also have a kz650 that is 500lbs (instead of 350), and the weight is high up! So it took getting used to.. Heavier cruisers have a low center of gravity, and I find them easy to control... and they aren't bad at slow speeds as long as you have clutch control (which you should practice). I've ridden my friend's dad's fatboy, and it was pretty easy to ride... even when moving from my 250.