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How hard are you gripping your penis when masturbating without underwear? You shouldn’t be gripping it harder than you grip your steering wheel while driving. I don’t think it can desensitize you but it can create a mental block that makes it difficult for you to get off any other way than that. I would start to go away from that method of masturbation and stick to just using your hand and maybe some lube
Rug burn is probably the only real concern
To your underwear, yes. To you? I can’t imagine how.