anal sex (Q/A, Misconceptions, How-To)

A few people have requested that I do another post on anal sex. This is a post that I write semi-regularly and I think is very important no matter how many times I write it. It would be impossible to include all of the information necessary (unless I wrote a book on it) so if you have any questions after reading please email me so I can further help you. I would also like to mention an incredible source for all of you to check out if you are truly interested in trying (or perfecting) anal sex. It is a movie called “The Expert Guide to Anal Sex” by Tristan Taormino. She is the anal sex goddess and this movie is a must if you want to experience pleasurable anal sex.

The first thing you have to do before reading anything about anal sex is throw your preconceived notions out the window. Here are a few popular misconceptions about anal sex.

Q: If you play with the anus aren’t you going to get shit everywhere?
A: No, not necessarily. Keep in mind that fecal matter doesn’t just sit and rest in the anal canal at all times. If you’re planning on having anal sex do it several hours after a bowl movement and not at a time when you feel like you’re going to need to go. Prepare as much in advance as you can by eating correctly so when you do have a bowel movement it is a clean cut, so to speak. This will prevent anything from being “left behind in the behind.” It is also beneficial to take a shower before having anal sex just to make yourself extra clean on the outside.
If you are especially particular you can have a enema done at home which essentially washes out the inside of the anus. This makes some people queasy, but it makes other people more willing to give it a go.
As a last thought, remember that sex is not supposed to be clean. Bodily fluids are being exchanged left and right and if a little brown smudge comes out on your dick grab a wet wipe and keep on going. It’s not going to be a full shit-storm, most likely just a bit of discolored discharge. Which, as I said, can also be avoided.

Q: Everyone tells me anal sex hurts, is it possible to have anal sex without pain?
A: First things first-if you have painful anal sex then you may not have prepared long enough. Many people approach anal sex like they do vaginal sex. The anus is NOT THE SAME as the vagina. It requires preparation and it’s own specific set of guidelines. Understand the anatomy of your own body and how it works before going about anal sex. If you do this and are relaxed it is entirely possible that you will have pleasurable anal sex the first time. If you are prepared and don’t have pleasurable anal sex the first time, don’t give up, try again, and work on what you’ve learned. Remember that pain is your bodies message that something is wrong and if you experience pain you should stop.

Q: Is anal sex safe sex?
A: There is no such thing as safe sex, only safer sex. In this mind set, yes, anal sex is safer sex. You cannot get pregnant through the anus just like you cannot get pregnant through oral sex. On the other hand, there is still the possibility of pregnancy when you are having anal sex. For example, some people have anal sex without condoms and when the ejaculate runs out of the anus it can slide down to the vagina. It is also possible to get STDs from anal sex so it is important to get regular testing done and be very careful to go slowly so you don’t tear a hole in the tissues inside the anus.

Q: Vaginal sex feels good, why would I want to have anal sex if I’m already satisfied?
A: It is a good sign of someone who is not sexually intelligent when you hear them give up where they start. If there is the possibility to experience a greater (or different) orgasm… why wouldn’t you want to try to reach it? It is possible for both men and women to experience more powerful orgasm from anal stimulation. That alone is good enough reason for me to tell you it’s worth the shot.

Q: You blog a lot about anal sex, is it your favorite thing to do in bed?
A: No, I can count the number of times I have tried anything in this area of sexuality on one or two hands. It is (at this point) not my favorite thing to do but I am still aware of the pleasure you can receive from it and think that it is a topic worthy of understanding. Not everyone is going to fall in love with anal play, but everyone can experience pleasure from it.

So as I said the first thing you need to do is throw everything you’ve thought about anal sex being “dirty” out the window- at least if it’s negative. If you, like many others, get thrills out of doing something taboo then keep those feelings around. They might just help you get things done. The more aroused you are the easier anything in sex is. So be aroused, get wet, and get ready.
After you’re all wet, erect, whatever- you’re going to need to know the anatomy. The anus is much longer than the vaginal anal and because of this can allow for deeper penetration. Unlike the vagina, however, it has a curve. Because of this keep rule number one in mind.

Do not penetrate too quickly or too hard. Go slow, work into it.

If you penetrate too quickly or too hard you may hit the wall on the inside of the anus causing some pain. It’s also not wise to penetrate the anus quickly without warming up first because the muscles will not have relaxed yet for this to be possible. This can cause bleeding, tearing, pain, and might even be impossible. More on basic anatomy later.
While it might be something you can get away with in the vagina, the anus is a different breed and does not self-lubricate. Which leads to rule number two.

Always use lubrication.

Lubrication is a must in anal sex and anal play. With no natural lubrication things can get dry and… as the saying goes, the wetter the better. Keep on hand a bottle of lubrication and do not be shy to use it frequently.
So you have lubrication, you know the basic anatomy, and you’re okay with the idea of being penetrated/penetrating the anus. The next step is putting all of this into motion.

1. Get aroused, stay aroused
Playing with your clit while he is working up your ass is very beneficial. It is important to stay aroused and in the game the entire time. Playing with your clit not only keeps you aroused but it keeps your mind off what he is doing to your anus. If you are simply thinking about what he is doing then you might instinctively tighten up making it harder for him to work his way in. Play with yourself, talk dirty, watch porn, or really get into how dirty it feels to have your ass played with. Whatever does it for you.

2. Make sure she is aroused
Men- it is also your job to make sure she is aroused. Make sure she wants what is going on. Do this by lubricating your finger and running it back and forth over her butthole. See how she reacts to your touch. Maybe reach around and rub her clit every now and then. Remember that it is never okay to go ass to vagina because of the potential bacteria so always use a clean hand or keep sanitizer/wipes handy.

3. One finger, slowly
Here is my continuation of basic anatomy. Before you actually can have anal sex or anal penetration of any kind you need to win over the sphincter twins, the internal and external sphincter muscles. Once you’ve worked the sphincter muscles open the anus will actually loosen up quite a bit and will actually stay “open” like a gaping hole of sorts for a few moments after being penetrated. This is why the initial penetration and warming up of the anus is so important and makes anal sex more pleasurable.

So- you’re rubbing your finger around the outside of the anus to warm things up. You start to feel things open up a bit. Now it is okay to slowly press the tip of your index finger inside. Notice how it feels and how she tightens up or loosens up around you. Most women prefer if you avoid any “come hither” motions at first and simply press straight in very slowly. It can be a strange feeling to get used to so communicate frequently and have her tell you how fast to go and when to stop or pull out.

I would also avoid from “thrusting” motions. Simply press, and continue to press in. If you get a hole finger in congratulation yourself and move on to the next step.

4. Thrusting, more fingers, and toys
Once she is warmed up to your finger begin experimenting further with her consent. You may start to thrust in and out slowly, add another finger, or pull out and use a small toy (slim dildo) or butt plug. Anal beads are also good for beginners especially if the beads on the toy go up in size. Be aware of how she feels, continue to communicate, and make sure things don’t get too dry. It is okay to stop and do something else momentarily if she wants to calm down for a moment.


I would suggest not continuing on to having actual anal sex the first time you experiment with anal play. Pretend like you are trying to obtain a PhD in anal studies. Notice how she feels, how she reacts, what it’s all about. How can you relax her the most quickly? What movements with your finger give the best reaction? What does she want to do, what does she want to try, how fast is she ready to move?

The most important things to remember are the relaxing of these anal muscles and lubrication. Open things up, relax things, and keep things wet. When you reach the anal sex phase remember that it is often incredibly intense for both parties. Most men orgasm very quickly the first time they have anal sex and most women experience very powerful orgasms. It is best to pull the penis out of the anus fairly quickly after ejaculation while things are still wet and open creating an easy withdrawal.

Feel free to point out any spelling issues I had in here, I only read through it once. Again, if you have any questions feel free to email me. Hope this was beneficial!

2 Comments Add yours

  1. Literalman says:

    “bowel movement” … not “bowl movement” 🙂


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