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It seems that recently, anal sex has become the hot new thing to do in bed. More and more people are trying it out, but the problem they're facing is that it just isn't working. It's either too painful or too uncomfortable for the woman; but in most cases the problem isn't that it's anal, it's just the execution.

The anus wasn't made for the purpose of penetration, there were other things in mind for it. This means it has no natural lubrication for the penis. If entering a vagina without some type of natural or artificial lube is like going down a waterslide without water, then going in the anus will be worse because that's not the only problem.

Vaginas were designed to accept the penis and then provide passage for a baby nine months later, meaning it was designed to expand. The anus was not. This is where large penises come into play. Sometimes a woman is put off by anal because the sheer size of the penis involved will stretch her anus way too much (which hurts). Unfortunately, short of finding another significant other, there's not much we can do about that, but our solution to the first problem may alleviate the pain enough for some women to handle the big penis.

Now, just like with regular sex, we need foreplay to warm up her anus before we go putting a penis in there. A good way to do this is by using a finger, and the doggy style is a great time to do this because your hand is right there. After getting her permission, you're going to put one solitary finger on her anus, not in, just on for now. Try to stimulate her anus by rubbing circles around it. It should be loosening up after a short while doing this, and as it does, that's when you slowly start putting your finger in.

But wait, remember what I said earlier? You need lube, and lots of it. Some of the pain and all of the irritation comes from the friction caused by the interaction between the penis and the anus, putting lube in there will remove it. Lather up your finger with your favorite lube before starting and that will help get her anus to open up. (Keep in mind that anuses come in all sizes, just like vaginas, so some may require more preparation than others.)

Take things slowly so she doesn't get surprised by anything. You should have your finger at least part-of-the-way in her by now, so just keep working it in deeper by going in and out. If you used enough lube it should not hurt or be uncomfortable at all. Once you can go all the way in, you can start fingering her like you would her vagina. There's no g-spot in there, but she can still feel it.

Once she's comfortable with the one finger thrusting into her, add a second one. Take this time to replenish the lube on your other finger since you need more for the new one anyway. Work them in slowly again so her anus has time to stretch out without hurting. Using the same technique as before, start fingering her with the two fingers.

Eventually she'll get used to that. When she does, lather up your penis with lube. Be generous. Then put a little lube on her anus to assist with the entry, as that will be the most difficult part. You'll start just like with your fingers; go slow and do not go deep. Go in a little at a time and then back out a little. You don't need to back all the way out; in fact, it may easier if you stay in, then she doesn't need to be entered twice.

Carefully work your penis in and out starting shallow and working your way a little deeper each time. If you feel like there's too much resistance, feel free to add some lube; only you and her will be able to tell exactly how much to use.

Once you get all the way in, start working the full length of what you have, but slowly. If she's ok, you can gradually speed up to your normal speed.

The most important thing to remember while doing this is to pay attention to her. You need to watch her body language and listen to her so you know if she's enjoying it. If she's in pain or wants to stop, you will gain nothing by continuing.

Alright, now the main points to remember are:

  1. Lube: lots of lube so the penis can get in and out easily
  2. Size does matter; if the penis is too big (that'd be nice, eh) it just might not work
  3. Start small, with a finger
  4. work it up slowly so her anus can adjust
  5. Pay attention to her and stop if she doesn't want to continue
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