My boyfriend and I have had anal twice before. Each time, we made sure we had a crap ton of lube, we made sure I had several orgasms before he even attempted it, and even used a plug to help get me ready.
Now, it's been a while since we've done so. For the past couple nights, we've made sure I'm lubed up enough, that I've cum a few times, but did not use the plug. And when only puts about half of his length in me, I'm okay, but when he goes (as they say) "balls deep", it hurts so much I want to scream, and I literally did the other night. It kind of ruined the entire mood.
I don't know what to do! The first few times I actually got off from it, this time it hurt too much. Any suggestions? Please?