The first time me and my boyfriend had sex it felt really good for the both of us. My boyfriend is on the receiving end when we have sex. Since the first time, when we try to have sex he acts like it hurts. It's really hard for him to get used to it because it either hurts a lot or it feels like he's going to have an accident. He never does end up having an accident, though. Sometimes, we try for a while hoping he'll get used to it eventually, but then when I start moving it hurt him. It seems to take forever! What is making all these other times so different from the first time? Why doesn't it feel good to him anymore? Please, Mona Lisa! We need your help!
-Top in Turmoil
Slow down there, hoss. Remember the tent scene in Brokeback Mountain? Yeah, that one. Despite what director Ang Lee wanted us to believe, anal sex isn't meant to be done Ennis-style.
Your man isn't "acting" like it hurts. It does hurt and is very uncomfortable for him. Don't be selfish (and yes, by the tone of your message you are being very selfish). Anal sex isn't a one-way trip down pleasure lane. If one of you is gettin' good and the other is gettin' pain, then you need to stop–at least for a while.
His pain could be the result of a lack of sufficient lubrication, an anal fissure, hemorrhoids or some other serious medical issue. I suggest that he see a gay-friendly doctor if the pain persists. In the meantime, give him a break. The anus is flexible, but it's not everlasting. And bottoming isn't for everyone.
So, come on! Try to be a little more sensitive here to the fact that your man is in pain. Instead of making him feel bad because of your lack of patience and sexual insensitivity, lay off the topping for a bit–at least until you know for sure what's going on. Try a little frottage or add a toy like a Fleshlight into the scene to mix things up. Try to help him relax and get him to a doctor.
Your man's bum isn't a sex toy ready to satisfy you only when you're ready. He could have a serious issue going on and you should focus on that instead of trying to recapture the experience of your first time. Think about it. If your gums hurts, would pressing your finger against them help you get "used to the pain"? Of course not. So, what would make you think by topping him more his bottom pain will go away?
Trying over and over again isn't going to get the feeling back. Figuring out why he's in pain and getting him help for it eventually will.