Trust me - Buy the shorts
I've been commuting to work (40 mile R/T) for about three months now. I didn't have any bike shorts. I was wearing cotton boxer briefs and cotton gym shorts. Sure, I was getting some saddle sores, but I thought "HTFU, boy. People used to ride bikes while wearing tweed suits."
I just got back from the doctor's office. I developed a HUGE boil where the saddle sores were. Ah yes....there's nothing like lying face down on a table while a doctor saws away on your buttocks like she's carving up the Thanksgiving Day turkey while saying "OK, don't move now...."
She didn't even manage to get all of it out. I've got to take some antibiotics and go back on Thursday so she can dig around in there some more. I hope she uses something more sophisticated than an apple corer, a teaspoon and a carpet knife this time.
Saturday I bought some bicycle undershorts w/ chamois in them. I also bought some of that butt butter they sell. I don't know how long it'll be before I'm up to riding once more, but when I do you can be damned sure I'll be appropriately attired.
Make sure that you're keeping things clean down south.
Chafing is one thing, but infections and sores can be indicative of another problem.
1.) Don't let your 'Skippy' moniker be in reference to your showering habits. ;)
2.) Baby wipes do more than just wipe away sweat, they reduce bacteria as well.
3.) Whatever you end up going with for shorts, try to get two sets, rotate & wash them daily.