Anal Sex Advice Part 3. Anal intercourse is best enjoyed when you are both fairly aroused - but not, let me add, so aroused that you get carried away, and forget the condom, the lube, or to listen to what she's saying (for example: "Stop! Stop!" It hurts!"). It's also a great idea to start with a finger, even if you want to get your penis in there. We've already had a look at how you might go about getting your finger into your partner's anus in a way that she enjoys, so - what do you do next? Again, the answer is, be very careful. Relaxation and slow progress are the key to successful anal sex, and of course using plenty of lube (I recommend "Probe".)
Start by looking where you are going. This isn't like going into a vagina, where the labiae will guide your penis in even if your penis is not at quite the right angle. You can't go into an anus by feel alone. You need to be sure you have targeted your entry correctly: if you try and do it by feel alone, your penis may well end up pressing into your partner's perineum or some of the soft tissue around her anus. A good guide to how much resistance you will meet is the ease (or otherwise) with which you can slide a finger in - and yes, I know this is much smaller than your penis, but her anus can relax to accommodate your penis with little more difficulty than it relaxes to admit your finger.
Another helpful tip is to have your lover guide you in - this also makes her feel she has more control over the process, and that could help her relax. But you must use your own hand to guide your penis in as well. And you must go slowly. Slowly. Slowly. You can probably speed up your thrusts when your partner has had the chance to get accustomed to the feeling - but do everything slowly to start with. When you begin to seek entry, ask her if it is OK to go into her body. And if she says yes, and welcomes you in, it will help if she says this out loud as you press at her rosebud: "I welcome you into my body. My body is relaxing to let you in."
As for positions - well, once you have decided on the basic approach (rear entry, side by side, woman lying on her back, or whatever) you are just going to have to try shifting position slightly until you find the right angle. Every body is slightly different inside, and the exact angle which will allow your penis in will be a matter for each couple to establish for themselves. The positions are not that different to normal vaginal sex: they just need slight modification, such as her legs being farther apart.
Perhaps the best way to get in is to use a kind of slight pumping or thrusting movement, starting by pressing at the opening, and then just adding a bit of pressure, then withdrawing, then going back again with a tiny bit more pressure - and so on. The sensation of your penis head - if that is the largest part of your penis - going through her anal canal may be strange, but it can actually be quite erotic, pleasant and arousing.
Of course, to feel pleasant, it has to be painless, and to be painless she has to be pretty relaxed and you have to be well lubed. You may have an advantage on getting in if your penis head is pointy and small, because it will ease her open gently and hopefully allow your larger penis shaft to get in behind it.
Very small cuts and tears are common when you go into the anus. Don't panic - these are just small lesions you will never notice, like the ones you get in your mouth every time you brush your teeth (no - you never notice them either). But unless you are absolutely sure of your partner's sexual history, this is a compelling reason for using a condom. The best combination is probably an unlubricated condom with plenty of Probe lubricant.
So - assuming you have gone slowly, and gently, you will probably now be deep inside your lover, connected in a very special way. Anal sex is a privilege for a man - I think it demands a lot of a woman, and it can be a real test of trust. Having said that, many women do enjoy it, and it can become a regular feature of a couple's sex life. So once you've both got used to it, and she is able to relax sufficiently to let her anus admit you and accommodate your thrusting, what do you do next? I guess you try other positions that will allow you to kiss, fondle and hold each other while you are inside her. One example would be to have the woman on top while she straddles you.
And a position where the man can thrust gently and intermittently so as to extend the time before he comes, while he can reach her vagina and massage her G spot and clit with his fingers could be helpful in allowing a couple to reach simultaneous orgasm - it's certainly worth a try.
Anal intercourse can be taken a stage further. The woman can penetrate the man in this way, too. No, this isn't a mistake. A woman can penetrate her man up the anus - and those couples who are into it seem to think it is rather delightful. And no, it doesn't mean that you're a repressed gay man (for goodness' sake. As if enjoying the erotic sensations of your anus is a problem). Anyhow, the obvious question is "How?" and the obvious answer is - she uses a strap-on penis.
OK, let me explain. It all centers, of course, on the prostate, that exquisitely sensitive area of tissue that men are fortunate enough to have just behind the rectal wall, conveniently placed so you can massage it from inside the rectum. And of course, a man can experience something like intercourse if his partner thrusts into him with a suitable artificial penis. This means the man has the pleasure of erotic sensations around his anus, while his prostate is also stimulated in a way that is certainly - at the very least - pleasant. (And the whole process might just give him an idea what his partner experiences during sex.)
There are many interesting aspects to the idea of a woman getting herself a false penis and thrusting into her man. Most obvious is the physical pleasure it can give a man, even bringing him to the point of orgasm, and if not, certainly increasing immensely the intensity of his orgasm.
But this goes deeper than just pleasure.
Men who allow their women to do this are saying something like - I am secure enough in my maleness to be happy with the idea of you thrusting something up my anus and taking the dominant position. For a woman who is usually - in some sense at least - submitting to the thrusts of her man, and who wants to know how penetration feels when you're on the other end of the penis, this can be a very exciting experience, opening up new ideas about relationships, power and the roles of men and women.
What's more, with the right sort of dildo, a woman will have a smaller protrusion in her own vagina, with the base of the strap-on pressing on her clitoral area - so she may well come from the thrusting - a novel experience for her.
OK. If you want to try it, go to the online sex shop "Babeland" and buy the recommended equipment: a slim silicon dildo called "Mistress" and a harness for your female partner to wear to go with it. Mind you, Babeland have lots of other stuff on offer as well, so you could always be adventurous and choose your own. Also, buy the video of Bend Over Boyfriend - an amusing video which is both educational and titillating - but which gives you all the information, tips and advice you need to be successful at this esoteric form of sex play.
There is plenty more information on anal sex at Anal Sex Information.