So my boyfriend, of 9 months, has disclosed to me a few times that he wants to try anal.. Of course I wanted to keep him happy, so we tried it a couple times but he barely got the tip in before I started crying!! He's totoally understanding and is only okay doing what I'm comfortable with and he would never force anything on me but I kinda wanna try it too! But I need some help on how to make it not hurt as bad. We use plenty of lube and I try to relax and go slow (and even have a few drinks) but it still hurts too bad. We've also tried building up with fingers but more than one finger hurts... Any suggestions on best position or any other tips to ease the pain?