The Mechanics of Penis-in-Asshole Sex

Now that you’ve prepared yourself by reading up on the health and safety risks associated with anal play, and you’ve trained your hot little asshole how to take something of significant size into it, it’s time to move on to the real deal. This short module explains the mechanics of how to go about performing anal sex for the first timer.

Lube Selection

Before you get started, you’ll want to ensure you have some type of lube available. Most people start out with water-based lubes such as KY, AstroGlide, or the like. These tend to dry out or absorb into the skin in rather short order, however, so you’ll need to reapply them from time to time. Make sure you have a bottle handy.

You do have two other types available for consideration, oil-based and silicone-based lubes. Both types are longer-lasting, but are a bit more of a pain to clean up once you’re done. The oil-based lubes also have the disadvantage of not being condom-friendly, so if you’re going to be using a condom for anal, you can rule those out altogether. My personal preference is for the silicone lubes, as they will usually last for an entire session with just one application.

Do note that saliva/spit and cunt juice are not sufficient lubricants for beginners. As you get more experience under your belt, you may get to the point where you can use those, but if this is your first attempt at being buttfucked, get some real lube to ensure the process is as painless and easy for you as it can possibly be.

How to Get Started

The best way to get started is to gradually work your way into it following a period of masturbating and/or vaginal sex, then incorporating some type of “anal foreplay” to help your little sphincter muscle relax. If you’ve read the previous modules, you probably realize there are a variety of techniques available for this, including:

  • Having him rim your asshole (working his tongue into the hole to help loosen it up)
  • Using his or your finger(s) to tease/penetrate the asshole
  • Using a dildo, vibrator, anal beads, or other toy to penetrate the anus (be sure you don’t use a silicone toy if you’re using a silicone-based lube!)
  • Inserting a butt plug and removing it when you’re ready to use a cock

All of those, of course, can be used in any combination.

When you’re finally ready for penetration, squirt a bit of lube on your asshole, and allow him to use his (one then two) fingers to push it into your anus. This not only distributes the lube but also ensures your sphincter muscle is loosened up to get it ready for penetration as well. If he’s fucking you in a doggy position, he can rest his hand on your back just above the cleft of your asscheeks and use his thumb to prepare your hole as well (this is actually pretty hot as a first-timer).

Once you’re ready to actually begin anal intercourse, make sure you have a good bit of lube in and around your anus. Have him roll a condom onto that big, hard cock (if you’re going to be using one), lube it up, put it at the entrance to your sphincter, and then SLOWLY slide it through the door. Sometimes it helps if you push out a bit as if you were trying to make yourself go to the bathroom. When the coronal ring around the head of his cock pushes through that internal sphincter, you’ll feel a little “pop.” This will likely send a little shiver through your ass, and perhaps even your entire lower abdominal cavity.

Give it a second or two for your muscles to relax and get used to it being there, and then he can slowly start pushing it deeper into your rectum. He’ll need to ensure he keeps lubing his cock up as he slides it deeper and deeper into your back door. If at any point you feel any pain, have him withdraw a bit, give it a few more seconds to calm down, and then try it again. It may take a bit of time if this is your first time doing it; that’s perfectly normal. At some point, unless he’s got a really long or a really thick cock, he should be able to get the entire length of his penis into your asshole. Once he’s done that, he can slowly withdraw it until just before the head is about to come out of your anus, and then slide it back in again.

As you get used to this sensation, he should be able to pick up some speed. Depending on your relaxation level, he may be able to get to the point where he’s thrusting pretty hard and deeply. The important thing to keep in mind is that, if at any time things start to become painful or uncomfortable for you, have him stop thrusting, let yourself relax again, and then pick up where you left off. It will take longer to get to this point if he’s got a fairy thick cock.

If it gets to where it’s just too painful, have him pull out slowly. You will need to spend some more time practicing as I have outlined in the preceding modules. It may take a few attempts before it gets easy for you and starts to feel really good. The determining factors will be ensuring you’re practicing with the right size toys and your mindset. Remember, you have to be a willing participant, someone who truly wants to be fucked in the ass.

You will likely want to masturbate while your guy is fucking your asshole. By all means do so. Recall that the anal muscles are interconnected with the muscles that provide your orgasm, and many of the nerves in that tight little hole actually come alive when you are aroused. So reach down there and play with yourself. If you’re one of those girls who believes that being sodomized is a “dirty,” slutty thing to do, think of how sluttily you’re being used at that moment and let your mind help the process out as well. If you have an orgasm while he’s in your ass, ask him how it felt to have those muscles clamping down around his cock while you were cumming. Note that masturbating is a good way to shift your mind’s focus from any pain as well, so if the anal is hurting a bit, doing so will help mitigate any discomfort.

Your guy should keep his eye on how things are going lube-wise back there. If you’re using a water-based lube, you may need to re-apply additional lube from time to time; that’s just the nature of the beast. If you’ve progressed to the oil- or silicone-based lubes (which have more staying power), then it won’t be as much of a pain to deal with. If he neglects this responsibility, however, and your anus starts to feel like it’s burning (which is the tell-tale sign of low lube levels), remind him to re-apply if he wishes to keep doing what he’s doing.

At some point, maybe on your first attempt, perhaps on a later one, your guy is going to thrust enough that he’s going to have an orgasm while he’s in your butt. If he’s wearing a condom, it’s no big deal. If he’s not, however, you’re going to end up with a rectum full of semen. When you’re done and ready to move on, you can go to the bathroom, sit on the toilet, and push it out (with gravity’s help). If you don’t, it will just come out with your next bowel movement. So long as he’s disease-free, there’s no problem with this, though your feces might be a bit more runny than usual.

When he withdraws his cock, it may have some brown stuff on it, even if you’ve cleaned out with an enema. This happens from time to time, even for those of us who are usually pretty clean. It’s always a good idea to have a rag or something handy to wipe things off if needed (including your anus, as it might have some residue on it when things are done as well). Don’t make a big deal about it. Act like an adult, clean it up, and go back to doing whatever you’re doing.

As you gain more experience with anal, you’ll get to the point where you will be able to reduce the amount of lube you use, you’ll be able to go straight to anal without having to “prep” your butthole with a finger or two first, and you’ll learn to squeeze your sphincter muscles to help orchestrate an orgasm from the guy fucking you. You may even arrive at the point where you can do anal “dry,” (without having to use lube at all). And as I pointed out in an earlier module, it is not uncommon for a woman to prefer anal penetration over vaginal penetration in some cases, so you may get to this point yourself (especially when you’re on your period if you don’t like taking it vaginally during that time of the month).

Alternating Other Orifices with Anal Penetration

One thing that many anal noobies often ask involve switching from anal penetration to oral sex or vaginal penetration. I’ll cover ass-to-mouth oral sex in depth in a later module, but do know that it is a fairly safe thing to do. Switching from the asshole to your cunt, however, comes with a little more risk. This is a good way to get UTIs, though a great many people do this sort of thing quite often without experiencing any negative effects. I highly recommend cleaning off the guy’s cock or switching condoms before you go from the back door to the front door, however.


There are a great many positions that can be used for anal intercourse. In my professional opinion, the best one to use for first time anal is the doggy position. This is primarily because it allows you, as the one who’s being penetrated, the easiest opportunity to control the depth and speed of the penetrations, individually and jointly. This is critical for someone who’s just having anal for the first time. If he goes too deep or too fast, you can simply move forward to remedy the situation. That is not always possible with most other positions.

Other commonly used positions for anal include:

  • Standing: This is basically the same as doggy, really. It allows for the same amount of control, but is just not as comfortable over the long haul for a first time sodomee.
  • Spooning Position: The spooning position is probably the second most popular for first-timers. It allows you to rest fairly comfortably while you’re working up to intercourse. The downside is that is kind of restricts movement by one or the both of you once the serious thrusting begins.
  • Inverse 69 (receiver lying face down, cock owner face down on top penetrating from above): This position is one where the guy doing the fucking can get seriously deep into your rectum. It’s not a good idea to use this your first few times because he can go very deep and you will have little ability to move away from his cock if it starts to hurt. Once you get used to being sodomized and want him to power fuck your asshole, though, this is the position to go with.
  • Cowgirl: Another decent position for a first timer. A potential downside to this is that, if your rectum didn’t clear all the water from it during your enema prep, it will leak out onto his cock.
  • Reverse Cowgirl: This is not a position you want to use for your first time, either, largely because your entire weight is being controlled by you. It does give you some control over the depth, but if you slip, you will sink all the way down onto the cock. If you’re not ready for it, it could be incredibly painful, especially if your guy has a long or a thick penis.
  • Modified Missionary: This is basically missionary, but with the sodomizer resting on his haunches, and either of the partners holding the receiver’s legs up or back to allow access to the his/her asshole. This can be a good position for a first time as well, and has the added benefit of allowing for eye to eye contact, which many couples prefer.

I’d encourage you to avoid the more acrobatic and extravagant positions until you’ve gotten some experience under your belt. You need to get used to the feeling of being penetrated and understanding how your body reacts to being buttsexed before you start adding gymnastics to the equation. Of course, if you’ve trained yourself well, that shouldn’t take long at all.

Now that you’ve gotten used to being penetrated anally, you really need to try being DP’ed, or double penetrated (penetrated vaginally and anally at the same time).