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I think I used to be in the same situation, used to always go for boxer-shorts since i liked having the swinging freedom, but my balls would get uncomfortable.
In comes Dual-Pouch underwear, best of both worlds for me. They look like normal underwear except they have a hole to put the penis in so it drops to the second pouch.
You get a good ball support and you don't have to squish your dick for it or the other case where everything is free, but so are the balls. This fixes that for me
I got the brand 'Separatec' style: everyday