Were you riding in an organized cycling event? 40 miles is a good ride. The shorts with pads work for ass and crotch comfort, but I don't like my dick being squashed. I rode in the Rosarito to Ensenada 50 mile bike ride in April. I'm not a big fan of lycra, but who knows how 50 miles would have been wearing gym shorts? Most of the riders were NOT wearing bicycle shorts. I have good ones, so I use them.
Nah, it wasn't organized at all, just out by myself down to Mt. Vernon and back. It was probably my longest ride in the last 20 years, too. I wore a cycling jersey (the kind with the drop tail & rear pockets) and Under Armour compression shorts. Nice & light, but cripes, the saddle certainly doesn't have enough padding on its own.. lol
When I'm just out to ride, I
much prefer tights over even bike-specific shorts. Baggy shorts, or even not-so-baggy shorts, still have extra fabric that gets tugged around and can catch on the nose of the seat. Earlier this year, I wore a pair of gym shorts that I could barely keep on my body because the saddle would always yank at the crotch and pull them down from my waist.
Plus, wearing just one layer of fabric is always more comfortable when it's hot outside.
I'll wear regular-looking shorts if I have a destination in mind (restaurant, museum, or whatever), but when I'm simply going out to ride for a while and come back home, I'm always going to wear tight shorts of some kind. It's a little bit exhibitionistic, sure, but there are definitely some functional reasons as well.
Plus, I got a nice "Hi" from a young woman at a stoplight.. :wink: