I guess I'll get to the point here.
My boyfriend and I have been together for three years now, and after having been together somewhere between six months and a year, he convinced me to try anal. I'd had a couple bad experiences in the past and so I refused at first, but he promised to do it the "right" way and started small with a lot of lube and attention to the front to help associate anal with pleasure. We worked our way up to a toy about the same size as him, and I can honestly say I now enjoy it immensely and even ask him to do it. The only issue is that we cant seem to be able to get him inside there. I don't know if it is because he's un cut, but for some reason, we just haven't been able to.
We've tried the lube, condoms, different positions, but no luck. Maybe I need stretched out a little more and should get a bigger toy? Anyway, any advice would be greatly appreciated.