So I finally finished a >50 mile ride today. Left with a local group and met up with a group from the next town north. Did most of the trip in the group @ 24-27mph and then had to ride home solo for another 20 or so miles against a ridiculous headwind @ around 14-19mph depending on the wind. Grand total of 55 miles.
I finally went after the ride and got some lycra bike shorts. Should help a bit in future rides as I've been averaging a bit over 100 miles a week.