Answer
I'd say it depends on your anatomy and what clothes you prefer to run in.
I've never used one, and never been troubled by any discomfort from my genitals.
Answer
Runners should definitely wear jockstraps. A jockstrap pulls your genitals in against your body so they don't bounce or get sore while you run.
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Definitely. A jockstrap keeps your penis and testicles in place and prevents bouncing and twisting.