You can do it by yourself, but it's usually not as much fun. It's usually hard to control your speed the first few times you try. It's best to have a soft place to land. You don't need any special clothing, but you can get some if you are really into it. If you're with someone who is having trouble keeping up, it's usually best to slow down and wait for them.
Most people think it looks easy until they try it for the first time.
Once you learn, you never forget how. If you fall off get right back on. If you get a flat, try pumping it back up. Remember to signal before you change direction. Make sure that you've got a firm grip.