Have Anal Sex

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Two roads diverged in a wood, and I, I took the one less traveled by, and that has made all the difference. --Robert Frost

So you're thinking about taking a trip down the hershey highway and you're not really sure where to begin. Good for you; after all, there are two holes for a reason. Also congrats for not just taking the plunge. The anus is not designed to take a penis, so unlike the vagina which requires almost no prep work, there are important considerations when entering the ass.

The Rectum is Not Clean

It's not a big secret that the inside of a person's rectum is not a clean place. Short of an isoprophyl enema (which would cause a lot of problems on its own) you are not going to be able to get rid of the potential bacteria that could be lurking inside your partners ass. STDs are a major fear when dealing with anal sex there is no doubt about that, even more so then regular sex. What you are not dealing with in regular sex though is the risk of nasty pathogens like E. Coli, which while occuring naturally in one part of your body is not something you want flowing around your blood stream. Urinary tract infections resulting from anal sex are not uncommon. For these reasons it is a good idea to wear a condom when you have your adventure. It is up to you and your partner whether you go in bareback or not, but remember if you find yourself drinking cranberry juice for two weeks you will only have yourself to blame.

It shouldn't hurt

With proper preparation, anal sex should not hurt. If you and your partner are tying anal sex for the first time, you will need to help things to loosen up. The biggest reason Anal sex might hurt is lack of relaxation. The recipient must be very relaxed; if you are nervous, it will hurt. Some ways to promote relaxation of the body and sphincter:

  • Body massage: A good long rub down will calm your partner down and help release any tension there may be.
  • Perianal stimulation: You can use good lubed fingers for this or a tongue. Since you've already cleaned things up there, analingus should be just fine. Slowly work your way around the anus lightly touching the anus itself and working in a finger, to the first knuckle. If this is your first time, you should probably start with a pinky.
  • Alcohol: The use of alcohol may be debated, but it does work. Alcohol will relax you, don't get completely smashed, just a little buzzed. The idea is to relax your anus, not dull out any pain that might be there. If things start to hurt even a little bit then stop, and slowly start again when the recipient is ready.

The key is relaxation. It is possible for the recipient to lay flat on their stomach and the giver will still have access to the anus. All the recipient's muscles should be relaxed. If you are holding your weight up in any way, make like a noodle and go limp.

Do your workouts

In case you didn't notice, the anus is nowhere near as flexible or elastic as the vagina is. What does this mean for the person who shall be trying to take a penis? It means that they will need to do some stretching. This is not to say that they need to do these excercises alone, in fact it is probably better if they are done with the partner who will be sticking it in. This way communication techniques can be practiced so that he is used to receiving instructions on going in. There are a few ways to stretch out the sphincter (ass) muscle, but be sure to use plenty of lube with each:

  • Fingering the asshole is usually the best method. A couple should start with one finger for about a week. After that, it should be possible to graduate to two fingers.
  • Use smaller butt plugs.
  • Use smaller dildos or vibrators.

Remember that the sphincter is like any other muscle. Few people can do a split without stretching, and the same goes for anal sex. Only when the sphincter is used to being streched should anal sex be attempted.

Lube me up, I'm going in!

The biggest mistake that you can make when trying anal sex for the first time is to not use enough lube. Lubrication is an absolute necessity, and no, spit does not count. Also lubrication from using a lubricated condom is insufficient. Instead, go out to the store and actually buy yourself a lubricant. The very good lube for anal sex is Astroglide. You may have a different preference, but just be sure to stay away from oil based lubricants if using a condom. This includes vaseline and others as they will break down the condom's latex and compromise it's ability to perform as a barrier. Be sure to use water based lubricants only. When you begin to use the lube, don't be shy, really pour it on. The bottle wasn't that expensive and honestly, do you really think that any problems would arise from having too much lube? To apply the lube first rub a lot around the asshole with a finger. Get the outsides glistening wet. Then take a finger, preferably the middle finger, lube it up well and finger the asshole for a minute or so. As you slide out try putting more lube on your finger so that you keep pushing more lubricant in. Finally, get the penis very lubricated. Fill a hand with the lube and rub it all over the penis. Make sure the head and the shaft are good and slippery.

Let's do this thing

Put your wetsuit on

Remember rule number one: Protect yourself with a latex condom - the consequences of not wearing one FAR outweigh any possible benefit, especially when engaging in anal sex. Alternately do it in the shower where you both can wash yourself immediately.

Flush the Pipes

This is fairly gross but make sure before you embark down the chocolate slide that things get cleaned out. This means that the soon-to-be penetrated should at least have a normal bowel movement before you attempt things. This will just make sure that everyone stays as clean as is possible (which still isn't very clean, but hey, it's an ass, what'd you expect?). Any type of enema will help to clean things more thoroughly.


The most important thing at this point is to relax. Having a penis enter your anus is enough to get excited over, and usually this will cause muscles to tense up. Try to have the person being penetrated think about something else, and try to reassure them not to be nervous. Make them as comfortable as possible for the best experience.

Assume the position

To get into position for anal sex the person being penetrated should get on their hands and knees while the other positions himself behind. This is typically best done by him/her getting on his/her knees, but not always. An alternate position could be missionary with a slight tilt of the hips so partners are face to face. The receiver needs to remember to push their ass out as far as possible. That will help spread the cheeks and asshole as much as they will need to be in order for him to enter with the least amount of pain possible.

In you go

The penis should be lined up at the entrance (or exit depending on your perspective) of the asshole. Gentle pressure should be applied to the anus. It will take time, especially if the recipient is nervous, but eventually the muscles will relax and the penis will gradually slide in. You will probably reach a point where it can't go in any farther. There is a 90 degree bend in the colon that will prevent rigid objects (such as your penis) going beyond that point. Some people enjoy some pressure at this point, but don't attempt to continue to force it in. If it bottoms out, then it is probably for the best and should not be pushed any farther. A good rule of thumb is that if there is anything more than slight discomfort during entry, something should be changed; either the rate of entry, or the nervousness of the recipient. Believe it or not, anal sex can actually be painless. This becomes easier with experience. Ultimately, the decision of how fast to proceed should be left up to the recipient. For some people, a feeling of slight pain is very pleasurable and they may want the man to push forward faster than a novice would.

Do your thing

At this point you should begin gently sliding in and out. Continue to keep the pace slow for a little while until their ass muscles fully adapt to having a penis inside. You will likely not be able to thrust in and out like you would during vaginal sex, so keep in mind which hole you are in. Some people may find it pleasurable to completely withdraw the penis and reinsert it. While he is thrusting in and out, the thruster might reach around and finger her clit or jerk him off if the anal sex is homosexual or if it is done to a man with a strap-on. While orgasm may occur purely from the anal sex, this added stimulation will add to a more intense sexual experience.

Time to Cum

It is highly advisable that, if the male is not wearing a condom, he should not ejaculate inside of the anus if it's their first time. During novice anal experiences, abrassions and cuts may occur (this is why lube is so important!). Semen is very salty and can be quite painful.