I am down around a 35 waist with a small spare tire, but I want to loose about 45 more pounds. I would probably buy a large short (36-38 waist) and hopefully be able to wear it for quite some time. I purchased a wal-mart shirt that I will try out when it gets warmer. Still don't own bicycle shorts, but can't say that I need them yet, because I only get about 30 minutes of bike time per day with our busy schedule.
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2007 Jamis Ventura Comp
2006 Jamis Explorer 2.0
2000 Specialized Hardrock (bought used)
Swim, Bike, Run and sounds like fun