Anonymous whispered,
Well, I don't really want to lose my virginity to him because we're not in a relationship, so anal has been our decision. I mean, it's pleasurable to me - when he fingers, so I want to try it - but is the pain something you just have to bear through the first few times. And, yes, we are using lube. Thanks for your help!
Okay, makes sense. But yeah, it’s pretty much guaranteed to hurt like hell the first time. And often other times after that, possibly. J often says it hurts most when I’m going in, so after I’m fully inside she has me stop for a minute or two while her body adjusts to it. After that, she says, it feels great and there is little to no pain. So if you can get past the initial pain, you should be good!
-E