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Originally Posted by Cervantes
I don't know.. touching that area is waay sensitive (mentally) for some guys, so I'd advice to ask before even going there. Better safe than sorry.
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Just let your finger glide towards his anus and play with the outer part. He'll get the message. And he'll either A) tighten his anus telling you he's not that comfortable, B) relax his sphincter and moan invitingly or C) sit up and say, "What are you doing?"
Or you can just discuss it in advance. It's the same way us guys approach the issue of anal-play with women.