100 miles on that seat? ouch...
I went 1.5 miles with my boys last night..and that was tough...whats the trick?
Padded shorts...and a whole lot of practice.
Seriously - a decent set of bike shorts, AND a well-fitted bike make all the difference. Find a local bike shop, not a big-box chain place. You'd be surprised how competitive their pricing is and you get real service from real riders. The shop where I get my gear has different rides 3-4 nights per week for anyone interested. Beginners, Ladies, Advanced, etc.
Being a bit more modest in my 40's than I was in my teens, I have padded compression shorts that snap into a pair of cargo-style shorts like a liner in a bathing suit. To the casual observer they look just like regular shorts - but my backside knows the difference!
My wife and I are just getting back into riding as well. We do a lot of "Rail Trail" rides - 8-10 miles, and we are headed for our first 20 miler in a couple of weeks, followed by a 35 mile jaunt in June.
I have a Specialized Sirrus road bike that is a nice entry-level multipurpose bike. Nothing quite as nice as Tim's bike (mmmmmm...Carbon Fiber!)- but I am not aiming for any Century rides anytime soon.