me and my g-f just tried tried anal. for both it was the first time. i have noticed the more she thought about we were doing it the more she felt the pain and therefore i couldnt get in. what worked for us was, while we were having sex i slid 2 fingers in her anus and fucked her in both holes. she had suck and incredible orgasm she about kicked me off the bed. there was a lil blood but it went away fast(kinda like popping her cherry). after that whe got on all fours and we did it. i used her juices for lube and she got off so hard she hit the ground but i never did. but we will try again and let ya know