I’ve never done it before.. unless you count the night he got wasted and stuck it in without me getting prepared for that and abruptly ended that sexcipade. So after we had sex tonight I told him that if he prepares me properly and we’ve decided together it’s the right time to do it, I’d feel comfortable with him to try it. I know he wants to with me now that we’ve been together for a year, because since that drunken night he won’t stop licking my ass while eating me out. (Which I don’t get anything from but he loves it so much I let him do it.) but what am I supposed to expect for this anal stuff? I told him to buy lube, but should I make sure we try it when I’m not working for a few days after? Should I get tipsy before we actually do it? What’s going to make this easier on me? Cause I wanna please him but I don’t wanna have a hurting booty afterwards.