Painful anal sex

[DRW]

Ok, I'm going to be a bit inquisitive here and ask how big is he? My advice would be lots of lube, and to take it very very slow. Try working the head in very slow. This may take a good 5 minutes or so. A little at a time, then once you get the head in, just hold it there, relax completely, and don't move an inch until you feel comfortable. Continue to take it slow until you can handle it. That's what I do. Slow is the key word. If you rush into it, you're not going to have a good time unless you like pain.