Back in July of last year I posted an article on anal sex and how to use enemas correctly to prepare for being fucked in the ass. You can think of it as more of an “advanced” article on anal sex. Originally, there was a link to an off-site tutorial I wrote a few years ago about how to prepare for your first anal penetration (based on how I’d learned to prepare). It has since been taken offline and so there is no longer anything of serious note to help those who might be at the outset of their anal explorations.
With that in mind, I am reprinting the article here, slightly modified. This is how you prepare yourself for your first anal, and will work regardless of your age. 
Before You Get Started
Before you begin, there are a few things to keep in mind. First off, the rectum can accommodate about 5-7 inches without any problem, but different people will have different “limits”. So use this information below when you’re picking out toys or other items to penetrate yourself with.
Second, there is normally not a significant amount of feces in the rectum except when you actually have to go to the bathroom. So unless you feel as though you’re about to need a bowel movement you generally don’t have to worry too much about pulling something out all covered with…stuff. Having said that, though, there is still the possibility that when something that has been in your butt comes out, it may have some small amount of fecal material on it. If it does, wipe/wash it off – it’s that simple. It’s a good idea to clean your back end itself with soap and water before doing anything related to anal sex, so be sure you take that step before getting started with any of the instructions below.
Finally, you may occasionally hear some misinformation about anal sex leading to inability to have normal bowel movements or “hold stuff in.” This is absolute bullshit. Think about it: The anus is a muscle – exercising it will only strengthen it if anything, so long as you don’t try to shove something way huge into it and tear it. Note that there are really two distinct muscles in the anus – the exterior one you can control, and the interior one, which is an involuntary muscle. The interior one is the one that gives the most trouble when doing anal. The key is to learn to relax it and get it accustomed to having something going *in*. This is covered a little more in depth in the advanced article linked above.
The most important thing you need to do to enjoy anal sex is to get into the mindset that you are going to enjoy being fucked in the ass. Period. You will have problems enjoying it as much as you could if you just cannot get over the fact that anal sex is dirty, disgusting, bad for your health, etc. The anus is one of the most nerve intensive area of your body, and anal play can add SO MUCH to your sex life if you just let it. There’s absolutely nothing wrong with a someone who doesn’t like anal sex in my opinion, I just think that it adds so much to the sex experience that it should be used for pleasure just like oral and vaginal sex. I mean, why not? What is there to lose?
First Steps
First off, you have to get somewhere where you won’t be disturbed. Like in your house, apartment, or dorm room when your parents, roommates and others aren’t there and you won’t be interrupted for a good period of time. A good place to set up is your bathroom.
Get something to use as lube, preferably KY or Astroglide, but you can use olive oil or other light oil if you don’t have or can’t get anything else.
Get into a comfortable position – on your knees, perhaps, or on your side – some position where you have easy access to your butt hole. Relax your anus and play with it a little bit, spreading some lube around it. This will help you get used to the sensation of something “being there”. The anus has a bad habit of tensing up a bit when something touches it unexpectedly. This is the single biggest hurdle to being able to open up and let something in.
When you’re ready, insert ONE lubed finger into your asshole and see how it feels. Push it slowly as far in as you can and once your butt is used to it, start sliding it in and out like a cock would do if it were in there. See how that feels.
Once you are comfortable with one finger in your ass, insert a second one and do the same routine, getting to the point where you can “fuck” your own ass with two fingers. Then, the same thing with three fingers, and if you’re really horny or want to go for it all, you can even try four. You can try this all in one session or over a series of them – it doesn’t matter. Go at your own speed and your own comfort level. If at some point it starts to hurt, back off to something that is comfortable and play with it for a few minutes before trying to progress again.
Once you’ve gotten used to having three or four fingers in there, you can move to using a dildo or a vibrator if you have one. If you don’t, you can use a banana, cucumber, or any other suitable penis substitute. Just don’t use anything short (that might accidentally pop inside), or anything made of a glass other than Pyrex. I wouldn’t use anything made out of wood either!
Ideally you want to use something with a flared base on it so that it can’t slip inside. If it does, you’ll buy yourself a ticket to the Emergency Room to have it removed, and that will be a tad embarrassing. The vast majority of vibrators and other sex toys are not going to have flares on them, however, so you’ll need to hang onto it tightly (wipe the lube off your hand!). To make things easier to clean up, cover whatever you’re penetrating yourself with with a condom, especially if it is not something that is designed specifically as a sex toy. When you’re done, you can just pull off the condom and dispose of it.
Do this several times over the course of a few days or so – whatever you are comfortable with. The point of this is that YOU are the one in control of the entire process, you can go at your own speed, insert things as far as you want them to go, and move to larger objects as you feel you can handle them. Doing this privately allows you the freedom to relax and go at your own speed and not feel any pressure to perform.
The idea is to get used to having something roughly the size of an average cock penetrate your back entrance over and over again. Once you’ve done this and gotten used to the sensation of something entering your butt, then anal sex should be a lot easier for you once you get ready to do it with a guy. You’ll know what it is going to feel like and how your body will react and how to manage those feelings. This is the key to learning to enjoy anal sex in my opinion.
The Real Deal
When it finally comes time to do it with a guy (or a girl with a strap-on), 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 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. Pouring a gallon of AstroGlide in your ass is not only unnecessary, it’ll make for a very messy experience. Use just enough to get the job done.
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 spoon 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!).
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.
Aftercare
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. 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.
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 follow-up article on enemas. It contains much more in-depth information on anal play and how it relates to other sex acts as well.
Feel free to add any suggestions or tips that helped you with your first anal experiences if you like – any information might be helpful to others who read this article and are curious about preparing themselves for that first butt fuck. 
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