I had that thought back in the day, because you know, one offers some kind of bulge and the other simply doesn't.
For a date = Always briefs.
For everyday life/PE = Boxers.
Men’s Underwear:
The Boxer Short – Incredibly loose with zero constriction. The downside is that they offer no support and have a lot of extra fabric. When you have them on around the house, they are super comfortable. But when you are getting dressed, that’s when things fall apart. A good boxer short has a button.
The Brief – They fit snuggly and offer more support. They make your package and butt look amazing.
The Boxer Brief – you don’t have too much fabric, but it can ride up, causing a bit of adjustment.
The Trunk (boxer brief + more "brief") – They’re not long. They are comfortable and supportive. For some people, the trunk is a bit too short.
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