This chapter is going to be a little strange because I actually have very little personal experience with anal sex but, in the interests of writing a well-rounded guide, I’ve interviewed several people who do have experience with it as well as performing the requisite research necessary to bring myself up to speed.

First, though, a word about safety: the human alimentary canal (the tube running through you from your mouth to your anus) contains many beneficial bacteria that aid in digestion as well as some not so beneficial ones that aren’t actively harming the carrier. These bacteria are only beneficial if they stay in the correct place in your body. When some of these bacteria are introduced into the first part of the canal, your mouth, they can cause serious illnesses. If you are going to perform anal sex it’s a good idea to use an enema first, to avoid oral-anal contact (commonly called a rim-job) and to use sanitary precautions when handling items that have been inserted into the anus. A condom, for example, can be used on fingers as well as an erect penis.

Men have a gland called the prostate located at the base of the bladder. The function of this gland is to create a fluid that aids sperm survival and to help expel semen during ejaculation. It is possible for some men to achieve orgasm solely through the massage of the prostate gland, through the anal wall, by either prostate massage or willing anal sex.

Women do not have this gland although they do have something similar which is called the female prostate, Skene’s glands or periurethral/paraurethral glands. They are located on the anterior wall of the vagina around the lower end of the urethra and they drain into the urethra or near it and it is likely that this gland is the female “G-spot”. The purpose of these glands is to secrete vaginal lubricating fluid which may have other properties. You may have heard of “squirters”, women who ejaculate during orgasm, these glands are the source of the female ejaculate. Stimulation of these glands during intercourse can cause female ejaculation.

All of my interviews and research indicate that a natural-born woman does not enjoy anal sex in the same way that a man would. In fact I’ve yet to meet or communicate with any woman who says she enjoys anal sex at all so I’m pretty much just going to go forward with the idea that anal sex is “just for men” and involves the prostate.

Now, some people might consider that a man who wants his prostate massaged is a homosexual. This is simply not true; a man who is predominantly sexually attracted to other men is a homosexual, and they either may or may not like prostate massages. The two are completely different things. In other words, straight guys like butt stuff too.

The prostate can be reached through the anterior rectal wall, toward the front of the body, and it may or may not be reachable with a finger. There are prostate massagers available, usually they have a curvature at the end in order to massage the prostate as well as a flare at the other end. The gland, itself, is about the size of a walnut and you’ll know you’ve found it when he says “there” or when he has an orgasm.

Massage is generally performed with gentle circular motions, you want to avoid thrusting. If you’re going to practice prostate massage with a finger it might be a good idea to trim your nails and buff them. Care must be taken not to damage the rectal wall with too vigorous massaging, damage to the prostate or the rectum can be quite dangerous so move gently.

Care must be taken when using a prostate massager that wasn’t designed specifically for the task so that you don’t lose the device in the rectum. Hospital emergency room workers all have many, many stories about the number and kinds of items they’ve had to remove from rectums so this is a fairly common occurrence. ER staff are not fun to have at cocktail parties. Most sex-toys designed for the purpose of prostate massage have flared ends to prevent the loss of the massager. It’s probably a good idea to invest in a sex-toy instead of using, say, a carrot. Even the most expensive prostate massager costs almost nothing compared to a visit to the emergency room.

The key to good anal sex, especially if you’re just starting out with it, is to go slow, get lots of feedback and use ridiculous amounts of lubrication. Ridiculous amounts, don’t be stingy with the lube. The rectum doesn’t lubricate itself as a vagina does, it’s simply not designed for the kind of actions that a vagina can handle so you can’t really treat it like one. Insert a lubed, condom clad penis or strap-on dildo slowly into the rectum until you reach the prostate then push in and out just a little bit, about an inch either way, this will stimulate the prostate. You may want to let your partner do the thrusting to maximize the stimulation of their prostate.

The anus can be “trained” by using a variety of tools designed for the job. In this way the opening can be widened, the rectal tissue made stronger so that it can be used for anal sex with less fear of tears or injury. To accomplish this, begin by using a small “butt plug” and keeping it in place until the rectum grows used to the size then use a slightly larger plug and so on until the anal opening is the size and strength desired. This process should take a number of weeks or months, the rectum needs time to adjust and grow based on use.

I hope you find this chapter helpful.

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