It feels great to us, we both cum super fast once we start that, and simultaneously finishing at the same time your partner does is such a good feeling. I think another thing is a certain level of trust that must be present, and that she trusts me to not just drive it home at the starting gun. But after years of that orange staring you right in the face, of watching other people eat their oranges and love them, you just want to eat the fucking orange and see what all the fuss is about. Masturbation can help you learn what does and does not feel good in a low-pressure setting, and it's better to get to know your own butt when you're totally relaxed and stress-free. Not so scary, right? Learning to breathe and, as a result, relax is the key to happy anal sex.
I like that she lets me do it anyway just to please me.
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Also, I just love the way a woman looks with something penetrating her lovely asshole. I like dominating. That said, I do love the feeling when my guy fingers my hole without any lube or just a little bit of spit. I have met a few women in my time that truly liked it and I think they liked it for the same reason. Apparently he thought it was weird, which is fine because my current boyfriend and I love it.