Anal With a Woman: A Guide for Men

It not hard or mysterious, but the first time can be a bit daunting. I remember going through the forums and 'how to' when I was trying to cross this bridge, and now, ten years later, I thought I'd offer some hard won advice to other men.

Now, you could be in one of two positions; one, you have a partner who's willing to give it a go and are looking for the nuts and bolts of how to do it right. If that's you, you lucky devil, skip straight to the second section on getting it in there. Or two, you haven't quite got the 'ok'. If that's you, read on about popping the question.

The proposition

You can't just jam it in there; surprised don't end well, trust me. But equally, you're chances of getting a yes from a sit down, serious conversation aren't great. Your best chances are when she is highly aroused after some serious foreplay. This is for two reasons, one being that anyone who's aroused enough will do things they would otherwise never consider, the other being you're in a position to go through with it before she has a chance to change her mind. I stress the arousal - if you have to pull out half way through conventional sex, then do it. You want her to be very, very, hot under the bonnet.

Getting it in there

Let me start with some fails:

•Surprise anal - I say again, serious fail. You'll probably not only hurt her physically but you'll piss her off as well. And then you'll never get another chance.

•Not enough lube - this can happen even if you have the best intentions, so avoid the hot tub, shower, ocean or anything else that will wash away your lube.

•The wrong kind of lube - most oils and some water based lubricants can sting or irritate that very sensitive area. Play it safe and stick to unfragranced water based.

•Going too fast or hard - this one is too easy to do; you get lost in the moment... and then you break the moment. Self-control and take it slow.

•Forgetting the clit - women can enjoy anal sex, but most get more out of clitoral stimulation than anything else, so you have to keep exciting her clit the whole time.

So as the boys scouts say; "be prepared". For the perfect first time you will need a lot of water based lube and a good vibrator is a good idea. The lube goes all over your cock and all around her arse - don't be stingy. The best position is having her on top. This way she can lower herself onto you and control how fast it all goes. She is, after all, in control of her sphincter, and can better time slowly relaxing while accepting you inside her if she has control of the movement as well. You really don't need to do anything with respect to the cock in arse part of the exercise except hold your cock straight up so that you don't slip around.

What you do need to do is keep stimulating her clit. That's where a good vibrator is invaluable. Although you can obviously do it with your hand, as soon as your hand gets tired its game over.

Now hopefully she will slowly take you inside her. Once you're all the way in either she can start moving your cock slowly in and out or you can take over. Either way, go very slow at first and take very short thrusts. Never pull all the way out. That's a trick that you might be able to pull next time when she's comfortable with having you in there, but it's not for the first time. If you remember to keep stimulating her clit you'll both be in for a good chance of cumming. Outsourcing the vibrator to her once you get going is a good ideas as she won't forget to use it and you'll have your hands free to play.

Getting it again

There are just two things here: If she liked it and doesn't feel bad about it afterwards, she'll be up for it again. That means you have to make her cum if she's able to. Even if you cum first, you need to keep going with the clitoral stimulation until she climaxes.

During you have to be respectful and afterwards you have to be nice to her. There is a lot of social stigma about anal - she probably won't run home and tell her mum all about it - so don't add to it. It's up to you to make sure it's not degrading and that she doesn't feel bad about it afterwards, if nothing else because if she does, you ain't goanna get another chance.

Hygiene

So this unsavoury section is worth adding. Anything that touches her arse, or touches something that has touched her arse, obviously doesn't touch her vagina. So that means never, ever, pull out of her arse and go back to her pussy, and if you slip out and hit the wrong hole, she will need to clean herself very well. I once read of a famous porn star, whose name escapes me, who became infertile after an infection through doing just that trick for the cameras, so it does really matter.

Also, needless to say, there are sexually transmitted diseases. Anal without a condom is probably the best way to get one short of sharing needles before prostituting yourself. It's also a good way to get yourself a urinary tract infection. And that's hard to explain to your doc unless you know them very well, as men don't usually get UTIs. So, seriously, I'd consider wearing a condom, even if I wouldn't for vaginal sex. It also means if it all goes pear shaped you can take it off and, all is not lost, have vaginal sex.

So there it is. Good luck and have fun!