I jumped right in at first, but over time I've grown to reading and gathering information. It never hurts to find out as much as possible, in doing so I found different techniques I want to try in the future. Also it helps to research a toy before making a choice, if you choose that route.
I read Tristan Taoramino's book, and I'm pretty sure my husband did some of his own reading for my training. As I've said before, it took about a month of training before I felt comfortable enough and was able to relax the muscles enough to achieve what we wanted.
We went from his giving me a little rimming to pinkie finger rimming, trying anal toys (which I actually didn't like until after we had succeeded in achieving proper anal sex) trying different lubes and we are still trying new things, years after we started our learning.
It opened a new door for us, as did learning about toys. I think every new activity or toy you feel brave enough to try can only add to your sexual repertoire. Of course, one should never feel pressured to engage in an activity they don't want to try, or don't like. But, honestly, revisiting one's "hard limits" from time to time only helps one grow as a human being and as a sexual being.
I was vehemently against anal sex when I was in my 20s. I did leave an open mind for "someday, maybe." As I got older, and my husband and I discussed it more, we realized we could learn new things and this was one of them. I'm glad I kept an open mind, even though it took me years of thinking about it. In fact, I wish I had been more open earlier. But, learning this in the last few years has given us a newer technique and activity to keep our sex life fresh.
For those into anal, did you just "do it", or did you copy what you say in movies, magazines, etc, or did you actually read books, blogs, educational material on the subject before "jumping in"?
I didn't know anything... at all. Neither, apparently, did my husband. I decided that I wanted to try it. And so, in doggie position, he proceeded to trying to stick his dick right in there. No warm up, no nothin. It. hurt. so. bad! And he didn't get it in. That thing clamped down tight.
Didn't try again until a long time later. We were dabbling in the swinging scene and one of the couples we met kind of gave us some advice. The wife told us to start in the spooning position.
So, we started with some warm up, getting everything all nice and relaxed and lubed up real good, and with us spooning, my husband just slid right in. We were amazed. This being the first (successful) time for me, I wasn't too sure I like the sensation.
It wasn't something that we did much of again... until recently. I have finally had anal sex where it feels incredible to me... and not like I have to go to the toilet.
I'm 100% self-taught. I used to give blowjobs to my best friend; one day he said, mid-blowjob, that he wanted to top me. I heard myself saying that I wanted him to top me. I managed to add "—but not NOW!"
I bought a plastic "classic" vibe and some KY and taught myself how to relax and open up over the next few weeks. I had a realistic dildo that was about the same size as he is, so once I mastered the vibe, I moved on to that. When he topped me, it was almost painless and VERY pleasurable.