Anal play. Let's talk about it. In the end, it's no more gross than sex (which is actually pretty gross, but is still awesome).
Basically, there are two ways to pleasure an anus: insertables or mouth. Insertables can be fingers, penises, toys, vibrators, beads, or anything else you decide to stick up there. Mouth is just that: kissing, licking, nibbling, or nuzzling. I have never actually used my mouth on someone's anus because I find that gross, even if the person just showered, I still have a hard time getting over the stigma. Plus, I wonder how awkward it is trying to get my face between two butt cheeks. If anyone out there has experience with this, please weigh in on the effect, techniques, pros and cons, etc.
But I have used insertables, both on myself and on a partner, so we're going to talk about that. Yes, I've had butt sex. And I have to say, it's different than vaginal sex, but it is still pleasurable. I like it when I'm feeling a bit rougher just because you can go to town with very little "damage" done. It is easier, granted, with someone who has a skinnier penis. Length isn't really a component, but girth definitely is. Just something to think about.
Positions that work well for anal sex are doggy-style (naturally), but also woman-on-top. As a matter of fact, woman-on-top may be better for your first time because you can control the speed and depth involved and be a little more in control of what is going on.
As for using insertables on a partner, I've tried using fingers on a couple different partners. And it's hot. There's something incredibly sexy about penetrating a partner and feeling the motions of your body echoing in theirs. It's also intimate as well - you're literally going inside someone, so respect that power.
Technique for fingers:
1. Start with just one finger and insert it slowly. When X and I first start anal play, I can only get my finger in to about the first knuckle. And that's okay! You cannot rush anal unless you want to traumatize your partner. Eventually, I can get my whole finger in, but it takes moving a little, resting so he can get used to the sensation, and then moving a little more. Take your time.
2. Movement is a good sensation. Try wiggling your finger and pulsing deeper. In and out motion doesn't work as well because the muscles react very fast and you're basically snapping them back into place every time you retract and forcing them apart again every time you go deeper. It's better just to find a good location and stay that deep until you're done.
3. Once your partner is used to one finger, you can remove it and try again with two. I haven't done more than two, but even two seems to be pushing it with my partners.
4. When you're withdrawing, GO SLOWLY. Again, when you withdraw, the muscles snap back into place. Do that too quickly and it will hurt your partner.
Grossed out, but intrigued by anal sex? Condoms are your friend! Even if you're fluid-bonded to your partner, it may be a good idea; even if you're fooling around in the shower, there may be a little bit of debris left on the insertable after use. You could clean the insertable off right away with soap and water, or you could just use a condom on the insertable and throw it away afterwards. X and I use expired condoms for my fingers. What else are we going to use them for? If you're planning to alternate between vaginal and anal sex, remember: you can go from vaginal to anal, but never the other way around. If you're planning to go from anal to vaginal, you need to clean the insertable or get a fresh condom. Just like cleaning yourself after using the toilet, front to back is safe, but never back to front.
If you want to try anal play, but you're not quite sure how to get into it, first broach the idea with your partner while both of you are of sound mind....then actually try it out (once you have sober permission) when you're a bit drunk. Why? (A) Because your inhibitions are a little lowered and it's easier to try something new. (B) Because alcohol relaxes your muscles and will make it easier to get something in. Another good idea is to try it during a co-shower - it's much easier to clean up after (yay soap and water!).
If you're not sure if you want your partner to try anal play on you, definitely play with yourself first to get an idea. First get yourself warmed up with general masturbation to get yourself in the mood. Then once you're feeling frisky, try it out. Try reaching from both between your legs and behind yourself to see what works best for you. Try it lying on your front and on your back. Remember motion is pleasurable, so wiggle your fingers and give it a shot.
There are cremes out there that will relax or numb anal muscles for you. If you want to try them, remember, apply it to the anus and give it a few minutes to sink in. After that, feel free to go to town with insertables, but don't ever use your mouth after you've used one of these cremes or you could end up with numb lips or tongue. Plus, they usually taste gross.
(Side note: when I was in college, I took a class called Human Sexuality. One of our assignments was to read a book on sexuality, any part of it, and write a review. At the time, I'd never done anything with anal, but I was intrigued by it, so I read a book on anal play. The intro lauded the anus, glorified the anus as a neglected sex organ. It ended the intro by proudly exclaiming "Love your anus!" It's hokey, but it's true. We love the cock and it both ejaculates and urinates. The anus defecates, but just like the penis, it can also be a playtime place. Love your anus!)