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A masochist hurts themselves, a sadist hurts others.
If it hurts, he didn't do it right. Not slow enough, not enough lube, etc. Plus, I seriously doubt anyone can do it first try. I had a girlfriend who wanted to try it. Never got more than 4 fingers in. Didn't force it. She did like anal though. Preferred it after a while. By that time I was the one who didn't want to do that anymore lol.