We had tried anal some time ago, but it was very painful. I have spent a lot of time trying to figure this out, because I really wanted to do it. He would use his finger in me, but I wanted much more than that. Over the weekend I told him to put one of my nice sized dongs in there and I figured out if I beared down during insertion, it eliminated the pain. So..... Last night he started acting like he wanted to put himself in there. I told him to use lots of lube. He took it slow until he was all the way in. OMG, when he got in there it was the most INCREDIBLE feeling. He was beside himself with the way it gripped him. He was being slow and gentle, but I eventually told him to "go for it". He "went to town" on me and I was so extremely turned on. My vag. was so wet from the pleasure of it and there was no pain. Let's just say....I've never heard him cum like that before. It was INCREDIBLE!!! I think the key for me was bearing down (as if I was trying to eliminate). It was perfect and I can't wait to do it again!! I hope this wasn't TMI.