This was actually a reply I wrote a while ago but I thought you might find it useful. As for positions, doggy-style anal intercourse is probably the easiest, especially the first time, but spooning from the side can be very pleasurable and intimate. Face to face works also, but it helps to elevate the woman’s pelvis with a pillow (if she is on bottom), use hands to carefully guide the penis into the anus (in all cases, but especially if woman is on top), and do a bit of leg wrapping and maneuvering (especially if face to face on your sides). Anyway, here’s my take on anal sex:
I am a 20-year-old female.
The majority of my anal experiences have been positive. The first time we put his cock all the way in my ass, we went too quickly, and although I enjoyed the experience overall, I hurt so much afterwards that I was to the point of crying and wanting to vomit from the pain. But I must make it clear: ANAL SEX DOESN’T HAVE TO HURT! If he and I do it right, I moan and cum like nothing else!
My partner and I prefer to use Astroglide–it’s not so sticky as KY Jelly and a little bit really does go a long way. It also has a slightly sweet taste.
The essential things that have made for some AMAZING anal experiences for me are:
1) Being In The Mood. If I don’t want something in my ass that day, nothing is going to make me loosen up.
2) Having A Clear Rectum. It may take some planning, but if you think you might be having anal intercourse, eat fiber the day before. I like having an empty, relatively clean ass before anal sex, but I’ve found that if I go to the bathroom just before, the tissues are sometimes a little torn or raw if I’d been constipated, and that makes anal sex stingily painful and continually irritating–no fun. So I like to stay regular before anal sex. Get to know your regular bowel movements, and plan accordingly.
3) Trust. This, obviously, takes time. But it also deepens the pleasure for both us. And without trust, I find it difficult to relax.
4) Relaxation. If I’m feeling loved and thoroughly adored, chances are pretty good that my ass is wanting it. If he as gone down on me and gotten me to cum once already, I’m even more relaxed. Things that really help to relax the anal sphincters for me are slow breathing, him massaging my ass (not just my anus, but the entire ass, cheeks and all), the sound of his voice, and slow and gentle finger play with my anus. I love the sound of my lover’s voice; I love to hear him tell me how beautiful my ass is, how much he wants me, how much he loves me, how wonderful it’s going to feel for the both of us when he is inside me. The sound is incredibly relaxing, and it builds the very intimate and trusting atmosphere. That and him teasing my ass very slowly with his fingers and Astroglide (we haven’t tried annilingus yet, but we are planning on it), makes sure I’m very ready.
5)Lubrication. Use tons of it. Much more than you think you’ll need, then add more later. Use it even when you’re just teasing the outside of the ass with your fingers–it feels divine. I’ve tried KY Jelly, Astroglide, saliva, Vaseline, and my own vagina secretions. Vaseline feels great, but it’s not condom compatible and it tends to leave greasy, irregular bowel moments for the following day or two. Both my partner and I love Astroglide. I carry a small bottle in my purse so we’re never without it!
6)TIME. This is CRUCIAL. Please go slowly. A lack of time taken has been the number one cause of my discomfort and non-enjoyment of anal sex. Don’t rush it; set aside plenty of time. I especially like my partner to go very slowly while inserting his penis into me. First of all, it allows the ass to gradually adjust, and you’re likely to tear fewer tissues (i.e. less pain). Secondly, I love the sensation of feeling my ass slowly being filled by his cock. I feel like I’m swallowing him. I really like to control the pace by being the one to slowly push back on him at the pace I’m ready to take him. And once he’s fully inside, there is nothing else like that!
One of the most exquisite sensations for me of anal sex is when he pulls out and then slides back in the first time. The in-stroke is absolutely amazingly pleasurable for me. I can’t help but moan and push back towards him. I love it. And anything he does to my ass makes my pussy sopping wet–I mean DRIPPING EVERYWHERE. I love slow at first, but there comes a point while he’s making love to my ass that I want to him speed up and just take me–outright take me. Hard, fast–it’s fantastic. It’s then that I feel completely full. The sensation is very different from having him in my vagina; everything is so very tight, and the pressure is what causes the pleasure. It just all feels so good. I find I can cum rather quickly with him in my ass, especially since I usually rub my clit once he’s inside me. My pussy gets my clit so wet, and it’s so swollen from the pleasure of feeling him in my ass, that it’s screaming to be touched! And it’s an AMAZING feeling to squeeze my lover’s cock in my ass as I cum around him. I cum so hard when he does anything to my ass, and with him inside me I usually cum so hard and squeeze him so tightly that he has a hard time moving because the sensation is so intense for him. It’s fabulous for me, and I find that I can cum again rather quickly if he stays in my ass and continues [censored] me (although after I’ve cum with him in my ass, I prefer a slower pace again for a while until we build up again). In any case, I love anal sex, and practice it a few times a month at least. Not all the time, but it’s something I definitely wouldn’t want to do without!
Whether or not you decide to have anal sex, I hope this at least answers a few questions from a woman’s perspective. Most of all, enjoy yourself!