Your First Anal Penetration

Perhaps the single most important thing you can do to ensure that anal sex is not a painful experience is to prepare for it correctly. Almost every single time I’ve had a conversation with someone about a painful first experience, it has come about that they did not “train” themselves to take something in the ass, and/or the couple proceeded too quickly which is why I spent so much time on preparation in the previous units. Now, it is time for the real deal.

The Real Deal

When it finally comes time to do it with a guy (or girl), make sure he understands that you are the one in control and you get to decide when, how far in, how fast, etc. He needs to know that if he gets too rough with it, it may be the last time he gets in your butt.

Make sure you use lots of lube. YOU lube up your asshole, sticking your/his finger(s) inside, and you or he can lube up his cock. Most people use a condom and that is highly recommended if you are not 100% comfortable that the guy is clean (free from STDs, etc.). Use plenty, but don’t use too much. You may occasionally hear/see people make statements to the effect of “there’s no such thing as too much lube with anal.” That is not correct. Pouring a gallon of AstroGlide in your ass is not only unnecessary, it’ll make for a very messy experience. You want to use enough to get the job done, but there’s no need to overdo it.

When it is time for him to enter you, I have found the best position for first time anal is the doggy position, with him being still and allowing you to back onto his cock. This allows you to be the one that decides how far, how fast, how deep, etc. An alternative is to use the spooning position with the two of you on your sides, but to me this makes your movements a little more awkward because both of you are resting on the bed (restricting your ability to move freely). If neither of these positions works well for you, try some others to see if you can find one that better accommodates your needs.

I’d avoid the reverse cowgirl or any other position that puts you bearing all of your weight over his cock. If you slip and sink down onto that cock unexpectedly, it is going to hurt and it may even tear the skin, resulting in bleeding and perhaps some other messy situations when you come right back up off of it in a hurry (and you will!). As you get more accustomed to the feeling of being penetrated anally, then you can move on to this and other more extravagant positions.

If it is still too painful to do, try the training process some more over a period of time and give it another go at a later date. Of course, you may eventually reach a point where you finally decide anal sex is just not for you, and that’s fine as well. At least you gave it your best shot.


Once you’ve finished your first round of anal sex, go to the bathroom and clean up. If he came inside you without a condom, you’ll probably need to evacuate your rectum (sit on the toilet and push). When you wipe yourself clean, it’s possible that you might see some blood on the tissue. That’s not uncommon for the first time or two, especially if your guy has a larger than average cock or you’ve used some larger toys (or maybe gotten a bit more vigorous than you perhaps should have). Be sure and wash anything that’s been in your ass with soap and warm water as well, including his cock if he went in without a condom.

You may find that your anus is a bit sore the next day. That, too, is not unusual. Just as with your first vaginal penetrations, soreness is a frequent side effect of a first experience. The more you do it, however, the easier it will become and the less soreness will be an issue for you. It is also not uncommon to experience some bloating and farting afterwards. Sometimes when the cock withdraws and allows air to get into the rectum, the thrusting motion will push some of it deep into the sigmoid colon. This will cause the bloating and the lower intestinal gas issues. This generally passes within a few hours. One key to preventing this is for the guy to not pull the head of his cock all the way out of your asshole when he withdraws (but sometimes it’s hard to control that with all the thrusting that goes on).

As with any other sexual activity, the more you do it, the more accustomed to it you become and the easier it gets without having to put a lot of thought into it. As you gain more experience and want to begin exploring more vigorous anal penetration, be sure and read the module on enemas. It contains much more in-depth information on anal play and how it relates to other sex acts as well. Following that, there is also a module on the mechanical logistics and other considerations related to anal sex in a variety of positions.