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What moment made you realize you couldn't be friends with someone anymore?

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ForeverOnMyGuard · 22-25, F
He complained to me about not being able to masturbate 5 times a day like he was used to five minutes after I told him I wasn't comfortable talking about anything like that. Previously, he'd been very sexual with me, unrequited, and I knew he had feelings for me. I just couldn't even try to be friends anymore and haven't talked to him since