Sumo wrestlers use a mawashi which has a similar issue. See this video: https://www.youtube.com/watch?v=xvF7wvkd-gI the guy’s wearing BJJ-style compression shorts bc otherwise he’d be naked at the beginning, but you can see that the mawashi has the same kind of “pouch”. Basically you just snake it around and tighten up afterwards, like you say.

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