Originally Posted by foehn
As others have said, shorts vary quite a bit in the way they fit. Generally the more seams in a short, the tighter it will fit. Some short fabrics are stretchier than others and this will make shorts fit differently. You might want to try some shorts with fewer seams; a bonus of this is the fewer-seamed shorts are generally less expensive in price.
If you want to use a short with more seams (more expensive) try the fit before you buy as you may be able to go a size larger depending on the fit and that may help you out.
And if you have a favorite style/brand you are trying on, try on EVERY short in the size you think you may be wearing, because, rest assured, every one of those shorts will fit differently!
I ask about mens shorts and crotch fit and the most informative and useful response I get is from a woman (thanks by the way!). Half of the guys who responded are too busy thinking about my package to be responsive to my issue. To be clear, it's not my penis that feels the pressure, it's my testicles. And don't assume that they are freakishly sized - it might simply be that they are very sensitive.
OK, that being said, can we get back to the question. Anyone know any make/model that seems to be looser in the crotch than other make/models? For example, I've noticed that the Cannondale liner shorts that came with my C'dale pants are roomier in the crotch than other size S shorts like Lusso and Nashbar Chronos.