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I've only done dp a few times. The closest I've come to the situation you describe. It was a very long time ago in Toronto. I met up with a couple swingers that lived in the Oshawa area. We met at a hotel. Did some different stuff of course but no male to male contact. I was in her pussy and he was in her ass. I wore a condom but he didn't. When we came in her ass we watched it drip out. She was very nice and sexy.