Input:
 The prompt for the above section of the story could be:

" Write a chapter titled 'What is the Prostate?' that discusses the prostate gland's role in the male sexual and reproductive anatomy. Include information on the prostate's size, shape, location, and texture. Provide an illustration of male anatomy highlighting the prostate gland. Discuss the prostate's anatomy in detail, including the urethra, the glands and ducts that make up the prostate, and the prostate's function during arousal and ejaculation. Include information on the phases of ejaculation, specifically the emission and expulsion phases. Discuss the concept of the 'male G-spot' and compare it to the female G-spot. Provide information on the female prostate, its function, and its relationship to the G-spot. Include information on the nerves involved in prostate stimulation and their role in arousal and ejaculation. Finally, discuss the concept of the root chakra and its connection to the prostate in Tantra practices."

Response:
**CHAPTER** **3**

**WHAT IS THE PROSTATE?**

_**"When it comes to sex we tend to focus mainly on the penis, but sexual stimulation actually involves many different parts of our bodies working together to create pleasurable sensations."**_

**—MICHAEL THOMAS FORD**

The prostate gland is a part of the male sexual and reproductive anatomy. It is responsible for making prostatic fluid, one of the main components of semen. The rest of the fluid that makes up semen is produced by the seminal vesicles, the bulbourethral (aka Cowper's) glands, and the testes/ epididymis. Estimates of the proportions of these fluids vary widely, but most agree that the contributions of the testes/  epididymis (which provide the actual sperm) and the bulbourethral glands make up a relatively small portion of the total semen volume, while the bulk of it comes from the prostate and seminal vesicles.

#  **PROSTATE ANATOMY**

**Illustration 1. Male Anatomy**

The most common way people describe the prostate gland is to compare it to a walnut. This is a good image to convey its size and shape, particularly for a young man. (The prostate tends to grow with age.) But as far as texture is concerned, the prostate is not hard and dry like a walnut, so we enjoy the alternative comparison suggested in _Dr. Peter Scardino's Prostate Book_ : "a small plum, with its spongy, fluid-filled interior and soft skin."1 This is a more palatable image for the prostate  in terms of texture, and it is close in shape as well. Now, for that small plum to be the size of the prostate of a young man, it would need, in fact, to be a _walnut-sized_ plum—very small indeed. For men whose prostate has grown with age (due to BPH or cancer), "a larger and sometimes more irregular plum would serve as a reasonable surrogate image."2

So imagine that small plum, only instead of a pit in the center, imagine a straw running through it vertically. That's the urethra, which starts at the bottom of the bladder, passes through the prostate, and then curves forward to run along the length of the penis. The prostate sits directly beneath the bladder and above the bulb of the penis (separated by a layer of muscle—the external urethral sphincter). It is located centrally in the pelvis, behind the pubic bone and in front of the rectum.

**SHALL I COMPARE THEE TO A WALNUT?**

One fellow we interviewed said that each time he looks for the prostate, he thinks to himself, OK, find the walnut. The walnut is the quintessential image people use to convey the general size and shape of the prostate, but you could compare it to a number of other things too. To broaden the options a bit, here are some other images and terms we have encountered:

a chestnut| "his special spot"
---|---
an avocado seed| "the grand gland"
a golf ball| "that round little bulge"
"the bulb"| "the male Sacred Gate"3
"my knob"| a "slightly squishy
"his sweet spot"| super-bounce ball"

Remember that we said the prostate was a gland? A gland is an organ of the body that produces a substance. Well, the prostate is also made up of glands: the individual, microscopic glands (called _acini_ ) which are tiny factories for fluid production. It's a bit confusing, because the term _gland_ applies to both the individual glands and the collective organ that they form. Think of it as a whole lot of tiny water balloons all interconnected and encased in one large water balloon.

During arousal, the tiny, microscopic _acini_ that make up the glandular tissue of the prostate are busily producing fluid. This makes the prostate swell as all those little water balloons fill up. Increased blood flow to the area may contribute to swelling as well. Some men who are very tuned in to their prostate can sense this swelling as a feeling of fullness at the base of the cock. It is often so dramatic that you can feel the difference with your finger during a prostate massage. As the prostate swells up and expands, its shape changes, becoming more rounded, and a larger portion of the prostate can be felt bulging against the rectal wall, making it easier to locate with a finger.

Each of the _acini_ is connected to a channel called a _duct_ which opens into the prostatic urethra (the portion of the urethra that runs through the prostate). During ejaculation, involuntary smooth muscles within the prostate contract rhythmically, squeezing the prostatic fluid out of the glands, through the ducts, and into the prostatic urethra.

#  **PHASES OF EJACULATION**

Ejaculation happens in two phases: emission and ejaculation.4 (To avoid confusion, the latter is sometimes called "expulsion.") During the first phase, emission, the prostate and other sex glands emit (release) their various contributions to the semen. These fluids are all pumped into the prostatic urethra.

Once the emission phase has started and the fluids have begun to be pumped into the prostatic urethra, the second phase, expulsion, occurs, during which the fluids are sent rushing through the urethra and out the tip of the cock.

**Illustration 2. Course of Sperm**

**COURSE OF SPERM**

Sperm are manufactured in the testes, then stored in two epididymides (the singular is _epididymis_ ) that sit on top of the testicles like little hats. During the first phase of ejaculation, the sperm are released from both epididymides and sent up through the vas deferens: two tubes (one on each side) that rise from the scrotum and up into the body. The tubes rise toward the front of the body, then loop around to the backside of the prostate, where they widen into the ejaculatory ducts. The ejaculatory ducts enter the back of the prostate and lead into the prostatic urethra. They carry the sperm as well as the fluid from the seminal vesicles, a pair of glands extending out from the back of the prostate like a pair of wings. Meanwhile, the prostatic fluid is sent into the prostatic urethra, so that all these fluids can be expelled through the tip of the cock.

#  **THE MALE G-SPOT?**

_"One cannot help but be struck by the similarity between descriptions of prostate stimulation and reports from women upon discovering their G spot."_

**—ALICEKAHN LADAS , BEVERLY WHIPPLE , AND JOHN D . PERRY**

The "male G-spot" is a name that more and more people are using for the prostate, especially when talking about its erotic potential. This has given rise to another term, the _P-spot_. Use of these names is especially common among sex educators and sexuality product retailers, though many people outside these communities also enjoy the idea of a male G-spot. There are a few reasons for thinking of the prostate as the male G-spot, which we will explain. But first, what is the G-spot?

In 1982, Ladas et al. published the bestselling book _The G Spot and Other Recent Discoveries about Human Sexuality_ , bringing this erogenous zone into widespread (contemporary) public awareness. They described the G-spot as a "sensitive area" that is usually located "directly behind the pubic bone within the front wall of the vagina … along the course of the urethra … and near the neck of the bladder, where it connects to the urethra."5 They noted that this area is responsive to deep pressure, swells when stimulated, and that some women can reach orgasm through the stimulation.

They also describe "female ejaculation"—the release of a small amount of fluid from the urethra that sometimes occurs during G-spot stimulation. They cite the suggestion, previously offered by J. Lowndes Sevely and J.W. Bennett (and  others before them), that some women ejaculate and that the expelled fluid comes from the female prostate.6

There is still some disagreement regarding female ejaculation, but for our purposes what is important is that female ejaculation was often observed to occur during G-spot stimulation (though it can occur at other times as well), and therefore the glandular tissue of the female prostate was suggested as the source of the expelled fluid. This link between the female prostate and the G-spot was further strengthened by the fact that this glandular tissue was in the right location to be stimulated during G-spot play, and offered an explanation for the swelling that was observed. So, because of these perceived links, many people began to talk of the G-spot as if it _were_ the female prostate.7

**WHAT IS THE FEMALE PROSTATE?**

As described above, the male prostate encircles the urethra below the bladder and is made up of glands and ducts that empty into the urethra. Females also have glands and ducts that surround and empty into the urethra. This glandular tissue has been called the paraurethral glands or Skene's glands, but it is increasingly being called the "female prostate," since this tissue is homologous to the prostate in the male.

What does it mean that the male and female prostate are _homologous_? It means that they are formed from the same tissue in an embryo. In the early stages of pregnancy all human embryos have the same blueprint anatomy, regardless of their future sex. The genetic sex is already determined by chromosomes, but for the first several weeks all embryos have the same basic structures  with the potential to develop into different genitals, depending on fetal development.

Since the sex organs develop from the same template, the resulting forms have many similarities. This is the meaning of _homology_. Every part of the male and female sex organs corresponds to a _homologue_ in the other sex. For example, the testes and the ovaries are homologous. Likewise, it is widely agreed that the male and female prostate are homologous.

Although the female prostate is commonly believed to be the female G-spot (that is to say, many believe that it is the anatomic structure responsible for G-spot sensations), this has not been established scientifically. The trouble is, this glandular tissue has not been shown to contain the types of nerve endings or the density of nerve endings that are usually found in an area of sensitive tissue.8 There is still plenty of controversy over exactly how the application of pressure to the area known as the G-spot leads to the sensations that women report, given that "no appropriate structure and innervation have been clearly demonstrated in this pleasurable vaginal area."9

Back to the (male) prostate. In _The G-spot_ , Ladas et al. point out that "men also have a pleasurable area located, like the G spot, around the urethra at the neck of the bladder. It is known as the prostate gland."10 They also point out that descriptions of how it feels to stimulate this area are very similar to descriptions of G-spot stimulation.11

**SIMILARITIES BETWEEN PROSTATE AND G-SPOT STIMULATION AND SENSATION**

• Both can be stimulated by reaching a short distance inside the body—about 2–3 inches vaginally for the G-spot, and about 3–4 inches anally for the prostate—and pressing through the front (anterior) wall.

• Both tend to respond to the same kinds of strokes. Most people who enjoy this stimulation find that they need deep pressure, not light caresses, to feel these sensations.

• Stimulation of both may result, initially, in a feeling like the need to urinate.

• For both, this stimulation is much more likely to feel pleasurable if arousal is high before it begins.

• Stimulation of both may result in orgasm, with or without simultaneous stimulation of the external areas of the penis/clitoris.

• Prostate and G-spot orgasms are often described as being subjectively different from orgasms that result from stimulation of the glans of the penis/clitoris (respectively). They reportedly feel "broader" and more "full-bodied" when compared to the more "local" or "focused" sensation of a penis/clitoris-induced orgasm.

• Prostate- and G-spot-induced orgasms are described as being felt "deeper" in the body, without the usual contractions of the pelvic floor muscles that occur with penis/clitoris-induced orgasms, though there may be contractions of deeper pelvic muscles.

So there are a few reasons why people talk about the prostate as the "male G-spot"—some of them valid, some maybe not. Calling the prostate the "male G-spot" or the P-spot highlights the fact that men, too, have a very powerful internal pleasure button to be explored, and that for men and women it's located in the same basic area, responds to the same kinds of stimulation, and feels very similar. This suggests that whatever is going on neurologically, it is the same for both.

In addition, people have called the male prostate the "male G-spot" because they believed the female prostate was the female G-spot. However, since it's not clear that the female prostate is responsible for female G-spot sensations, some sex experts disagree with this terminology.

#  **ABOUT NERVES**

At this point, we'd like to make a few observations about nerves. The body has different neural systems that serve different functions. The sensory/motor system controls voluntary, conscious activity. Most of the sensory receptors of the body are a part of the sensory/motor system. Different kinds of sensory receptors pick up different kinds of stimuli. When a sensory receptor picks up a stimulus to which it is sensitive (has the capacity to register), it sends a signal to the brain—or to the spinal cord, in the case of a spinal cord reflex. When the brain receives the signal, it can interpret the sensation as pleasurable or otherwise. The pudendal nerve, which innervates the skin of the penis (and also the perineum and anus), is part of the sensory/motor system and has plenty  of sensory receptors that send signals to the brain/spinal cord.

There is also the autonomic nervous system, which controls involuntary (and often unconscious) functions of the body, such as blood pressure, breathing rate, and perspiration. It also controls arousal and ejaculation. The pelvic plexus, which innervates the prostate gland, is part of the autonomic nervous system. The portion of the pelvic plexus that innervates the prostate is called the prostatic plexus. The nerves of the prostatic plexus serve important functions in emission and ejaculation. Also, some of the nerves in the prostatic plexus continue to the corpora cavernosa of the penis and are responsible for erection.

The prostatic plexus contains some limited sensory receptors that travel with the autonomic nerves, but not many, and these receptors are not able to pick up a wide range of sensation. So we find ourselves with the same question as with the female G-spot: if the male prostate does not have the kinds of sensory receptors that would allow an area to be "sensitive" and to send lots of sensory input to the brain for the brain to interpret as pleasurable, can the prostate really be said to be the source of the good feelings that men experience during prostate massage?

Myrtle Wilhite MD says no: "Massaging the gland itself (while it has health benefits of pushing some fluid out) does not lead to sexual arousal." She suggests that what is really happening is that the autonomic nerves of the prostatic plexus are being massaged—and the impact of this massage is not mediated by sensory receptors.

She explains, "These nerves are part of a finely webbed  neural relay system which transmits arousal information between the clitoral/corpus cavernosal nerve endings back to the sacral spine (S2–4) and back again." It is this spinal cord reflex that builds arousal. So, she continues, massaging these arousal nerves that "wrap around and dive into the substance of the prostate gland … amplifies or increases the number of stimuli relaying to the sacral spine," thereby creating the feelings of intense arousal that are associated with prostate massage.

Meanwhile, "our sensory nerves may tell us (internally) how the prostate gland feels about being massaged (level of touch, sensation of vibration, sensation of pain, etc.), but they are not directly related to how we experience the arousal of the pelvic plexus… So in this way, although we aim at the prostate as something to massage for sexual pleasure, it is more the road sign that tells us where the nerves of the pelvic plexus are."

The neurological source of female G-spot sensations has been an active area of research for quite some time. We hope that, as prostate stimulation gains more widespread attention as a source of pleasure for men, research will be directed to this area as well.

**THE ROOT CHAKRA**

In Tantra, there is a practice of getting in touch with the flow of energy inside your body. With practice, many people can learn to feel a flow of energy inside them and to circulate it in the body. The energy is called _Kundalini_. Practitioners say they can feel it move along certain channels and gather in pools in certain areas the body. The pools, which are mapped vertically through the torso and head, are called _chakras_ (pronounced SHOCK-rahs).

What does this have to do with the prostate? The prostate is said to be connected to the _root chakra_ in men. The root chakra is located just below the prostate and it is the seat of Kundalini. This is significant because the way to have a full-body orgasm is to draw the Kundalini energy up from the root chakra and circulate it throughout the body.

We spoke with Jan Robinson, a Certified Ipsalu Tantra Kriya Yoga Instructor, about the relationship of the prostate to the root chakra, and she explained that because of the prostate's connection to this chakra, "when [a man's] prostate is stimulated, either directly or indirectly, his root energy gets stimulated too."

She also explained that this usually doesn't happen with traditional intercourse, unless the fellow is involved in Tantric practices : "One of the drawbacks for a man in conventional sexual intercourse is that his root chakra [typically] does _not_ get stimulated. This means his Kundalini […] the energy of evolutionary consciousness, the source of supercharged full-body orgasm, is not awakened."

There are Tantra techniques to activate the root chakra and bring the energy up the body that don't involve prostate massage but rather breathing, meditation, or muscular contractions. But prostate massage is a great way to do it too!

It's also interesting to note that this idea that prostate stimulation can stimulate the root energy, awakening the Kundalini and allowing for full-body orgasms, is quite consistent with what men commonly say about prostate stimulation: that it tends to feel  more full-bodied than cock play alone and can feel like waves coursing through the body.

Here is one interesting possible explanation for this: some have suggested that the chakras correspond to the nerve plexuses, such as the pelvic plexus, that run vertically through the torso.

SOURCES OF QUOTES

Michael Thomas Ford, _Ultimate Gay Sex_ (DK Publishing, 2004), 23.

Alice Kahn Ladas, Beverly Whipple, and John D. Perry, _The G Spot and Other Discoveries About Human Sexuality_ (Holt Paperback, 1982), 134.


Input:
 The prompt for the above section of the story could be:

" Write a chapter titled 'Hygiene' that discusses the cleanliness concerns that men of all sexual orientations face when they start exploring prostate play. Include information on the importance of washing before play, the use of mild soaps, and the potential risks of not washing properly. Discuss the concept of the 'gotta go' feeling and how it is often a misinterpretation of the body's signals. Discuss the role of diet in the cleanliness of the rectum and provide tips on how to maintain a healthy diet. Provide quick tips for more hygienic anal play, including the use of gloves, towels, incense, and easy-to-clean materials. Discuss the use of enemas and provide guidelines on how to use them safely, including the type of water to use, the water temperature, how to hold the water in, and how to repeat the rinse. Discuss the importance of using safer sex barriers, including gloves, condoms, and dental dams, and how they can reduce the risk of contracting infections. Discuss the various types of gloves, including latex, vinyl, and nitrile, and their advantages and disadvantages. Discuss the use of condoms and how they can keep toys clean, especially if they are porous. Provide tips on how to use condoms effectively, including proper storage, expiration dates, opening the wrapper correctly, and using lubricant. Discuss the use of dental dams and how they can be used for cunnilingus and anal-ingus. Provide tips on how to use dental dams effectively. Discuss the topic of hair removal and provide information on the benefits of grooming the anus, including the ease of cleaning, prevention of pulling during penetration, and improved appearance. Discuss the options for hair removal, including shaving, waxing, and trimming, and provide tips on how to do each effectively. Discuss the potential risks of hair removal, including ingrown hairs and irritation, and provide tips on how to minimize these risks. Discuss the use of shaving cream, hair conditioner, and unscented lotion, and provide tips on how to choose the right product for your skin. Discuss the use of home wax kits and provide tips on how to use them effectively, including the importance of not waxing the scrotum. Discuss the potential risks of waxing, including pain and skin irritation, and provide tips on how to minimize these risks."

Response:
**CHAPTER** **4**

**HYGIENE**

Among the men we surveyed about prostate play, fear of "the mess" was the number one concern men of _all_ sexual orientations faced when they started out. This anxiety can be a big, distracting turn-off. Nothing will kill an orgasm faster than a little voice in your head shouting "Smelly? Messy? Gross?" and wondering whether your partner will run out the door in disgust.

A certain level of caution is a good thing, since there are some realistic cleanliness concerns, such as diseases that can be contracted through anal play and contact with fecal matter. (We discuss this below.) But the anxiety that some people feel when exploring anal play may have more to do with stigma than with these rational concerns.

It may be difficult to cleanse the reputation of the ass, but thankfully the real thing cleans up quite easily. With soap and warm water, the anus will be clean and fresh smelling, just like any other part of your body. There may be a faint residual odor—this is a natural odor and usually not an offensive one. In fact, as with many body scents, some people really dig it.

If you have concerns about cleanliness, washing before play can help ease your mind considerably, both by cleaning things up and helping you relax. Take a shower or a bath and suds up your hole with a mild soap that does not contain dyes, scents, or harsh chemicals, as these may irritate the anus and cause itching. You can insert your finger a little bit into the hole, but don't go deeper than the anal sphincters because soap can irritate the rectum—the last thing you want before a date! Rinse thoroughly. Washing is particularly advisable if your play includes rimming (oral-anal sex), as there is high risk for catching intestinal parasites or certain STIs if the receiving partner is infected.

It may also help to know that if you have a good diet (lots of fiber, not much grease), there shouldn't be much residue in the rectum. In fact, it should be pretty empty right up until you have that "gotta go to the bathroom" sensation. However, if your stool is loose or if you have constipation, there might be something left behind. Changing your diet can help a lot, but if the diarrhea or constipation are the side effects of a medication, there may not be much you can do.

When you're new to anal play, it might feel like you need to go to the bathroom. Most of the time when this happens, you don't really have to go. It is simply that your body is taking the  signal of a full rectum to mean what it usually means—time to stop at the john! So you feel the urge to go, even though in all likelihood no stool is present. It may take a few times before your body learns to reinterpret the sensation and the "gotta go" feeling stops coming. To make that easier, hold still and breathe with deep, slow inhalations and deep, slow exhalations.

#  **QUICK TIPS FOR MORE HYGIENIC ANAL PLAY**

• Wear gloves to keep your hands clean.

• Put a towel on the bed to keep the sheets from getting dirty. Keep a hand towel or baby wipes nearby, in case you need to wipe up. And maybe a third towel so you have somewhere to put your used toys when you're done with them.

• If you're concerned about odors, light some incense or a scented candle.

• Use toys that are made from easy-to-clean materials, such as silicone, intramed, or hard plastic. Taking care of these products is simple: wash them well with soap and hot water. You can also put silicone toys in boiling water for five minutes to disinfect them.

• If your favorite toy isn't so easy to clean, or if you're not sure, just cover it with a condom.

• Shower before play and wash the anal opening with a mild soap. Rinse well.

• If you want, you can clear the contents of the rectum beforehand with an enema. Disposable enema bulbs are available from most drugstores. Just be sure to look into enema safety before you give yourself one! (See below for more info.)

• An enema is not the only way to clear out fecal matter. As crude as this may sound, you can check yourself for large chunks by simply reaching in and feeling around. Put on a glove, dab on some lube, insert your finger, and feel around. If you find anything, try to hook your finger around it and sweep it out.

#  **ENEMAS**

Some people like to have an enema to rinse out the rectum before penetration. It isn't a necessity; lots of people do without it. As mentioned above, there usually isn't that much poop in there. However, some people like the feeling of inner cleanliness and the peace of mind that an enema brings. Also, feces can be abrasive to the rectal tissue, so an enema may add to your comfort and the longevity of your session. If you are playing with large objects, lots of motion, or for long periods of time, an enema may be a good idea.

##  **Enema Guidelines**

Here are some pointers on how to give yourself an enema.

###  _**Use the right water**_

If you don't drink the water that comes out of your tap without filtering it, why would you put it in your rectum? Use the same filtered water that you drink for your enemas. Adding salt to the water makes it easier on your body because saline water won't absorb salt from your body. Add 1/2 teaspoon of uniodized sea salt per 8 ounces of water (1.25 ml of salt for 240 ml of water). It doesn't have to be exact, and a bit less salt is easier on the body than a bit too much. If you're only occasionally doing enemas, salt may not be necessary, but if you do them regularly, it's a good idea.

###  _**Water temperature**_

The water you use for your enema should be warm. Not too hot—that'll burn! And not too cold—that could give you cramps. Test the temperature on your wrist before squirting it up your ass. It should feel warm and pleasant. If it's too hot or too cold for your wrist, chances are it won't feel nice on your insides, either.

###  _**Hold it in**_

Once you take the water in, hold it for a few minutes or as long as you comfortably can. This allows the water to loosen up the solid matter as much as possible so that more of it can be flushed out.

###  _**Repeat the rinse**_

It is common to repeat the rinse—fill the rectum and then empty it two or three times in one enema session, until the water runs clear. Don't do it any more than that, as it may irritate the lining of the tissue (which won't help you out on your hot date later).

###  _**Time it!**_

Usually, if you're doing a shallow rinse, all the water comes out very quickly. If you're doing a deeper rinse, most of it will come out within 15 minutes, usually in a first and second wave. However, if you take in a lot of water, some of it may remain inside, deep in the bowels. This remaining fluid may come insistently to your attention up to an hour later, so leave at least an hour for the enema to clear. Allowing a little time also gives your rectum a chance to settle after the disruption of the enema, which can feel a little uncomfortable when you are new.

###  _**Don't overdo it**_

Every time you have an enema, you are affecting the state of your intestinal microflora. If you are rinsing too many times and too often, you may disrupt the balance, and this can cause disturbances in your bowel function.

##  **Fleet and Bulb Enemas**

A Fleet enema (a trade name) or bulb enema consists of a small bottle with a narrowed tip. You fill it with water, insert the tip up your ass, and squeeze the bottle to squirt the water inside you. They can be purchased at most drugstores. The Fleet enema is disposable. It comes in two versions: one with a laxative and one without. Get the laxative-free version, or, if you can only find the laxative version, dump out the solution, rinse the bottle, and fill it with saline water. You can refill it and reuse it a few times in one session, but they're not meant to be used for more than one occasion. They're very handy when you're traveling, though. Bulb enemas can be washed and reused.

Both of these are fairly small bottles, so they give a shallow cleanse. Since the prostate isn't very deep, this may be all you need. To rinse a little deeper, take in the water, hold it inside you, and refill the bottle and give yourself several more fillings before you release all the water at once.

##  **Bag Enemas**

A bag enema holds more water, so it can rinse deeper into the GI tract. This thorough cleanse is especially popular for people who are into large objects, fisting, deeper penetration, or long-duration play. Some like it so much that they use it for any kind of anal penetration.

It consists of a rubber or plastic bag that you fill with water and an outlet tube through which the water flows. You insert the lubricated tip of the tube into your ass, then open a valve to let the water flow in. The bag should be higher than the  tube so that the water flows naturally with gravity and the air bubbles go to the top of the bag and not into your GI tract. (Air bubbles can give you cramps, just like when you have gas.) However, you don't need to elevate the bag so high that the water comes rushing in forcefully.

Be careful of the mud factor! Introducing any type of enema might make what would have been only a few traces of poop into a mess of sludge. You may have to repeat the enema a second or third time before the water runs clear.

#  **SAFER SEX BARRIERS**

If you think that using barriers is a turn-off, you may find that a few hot sessions of prostate massage quickly give new meaning to the sound of a snapping glove! Some people resist barriers because they aren't used to them and think they will be a hassle. While a barrier may be a little awkward at first, with a little practice, you may find it's just the opposite : barriers add convenience to your sex life. They make it easier to switch from one activity to another without having to make a trip to the sink to wash up. If you use gloves to finger your partner's ass, then you can slip them off afterward and you don't have to worry about putting your hand down on a nice clean pillow.

Using gloves, condoms, and dental dams for anal play can help both partners feel more relaxed about keeping things clean. It also makes your play safer by reducing the risk of contracting an infection. There are many ways that infections can be spread during anal play:

• Oral-anal contact (rimming) can transmit intestinal parasites and some STIs (sexually transmitted infections).

• Accidental oral contact with shit (from unwashed hands) can transmit parasites and may transmit some STIs.

• Unprotected anal sex can transmit STIs, especially for the receiver.

• Unprotected anal intercourse puts the giver at risk for prostatitis, since bacteria can enter the urethra and travel up to the prostate. (See chapter 14, Prostate Health.)

• Sharing toys may carry risk for STI transmission.

##  **Gloves**

In addition to keeping the hands clean, gloves can also nicely smooth over any rough areas on your hands so that the receiver gets a smoother ride. Of course, gloves that are poorly fitted and bunchy won't feel much better! Often the receiver can feel it when the gloves are wrinkled, especially at the anal opening, where wrinkles tend to gather. Pull them on snugly so the fingers are as smooth and wrinkle-free as possible.

If wrinkles gather at the base of the finger, use plenty of lube on that area. You might even favor motions that minimize the friction at the anus, such as curling the fingers and keeping the hand stationary rather than moving fingers in and out. Different brands and materials of gloves fit a little  differently, so shop around. A snugger fit means less friction for the receiver.

To reduce the obtrusiveness of wearing a glove, try this trick: put the glove on, squirt a little lube into the glove, and work it down to the fingertips. The feeling of wetness on the inside almost makes it feel like you aren't wearing a glove at all. It also reduces the bunching effect that can happen with gloves that don't fit quite right.

Gloves come in a variety of materials. Latex gloves are inexpensive and easy to find at a drugstore. This material is thin and flexible, and many prefer the texture, since it has so much give. Make sure you don't use them with any oil-based lubricant, such as Vaseline, baby oil, or massage oil. Oil breaks down latex, and this may cause the barrier to break. Unfortunately, many people have latex sensitivities and can't use latex barriers; there are vinyl and nitrile options for them. You can get gloves in these materials at some drugstores. You can also purchase them online from dental and medical suppliers, and from many sex toy retailers. If the plain white glove feels too medical to you, find a color that feels a bit more "oh-la-la!" A wide variety of colors are available, including black. You can find them online. Just don't get the loose vinyl gloves that are used in food service, since they get really bunched up.

If you choose not to wear gloves for anal penetration, be sure to wash your hands thoroughly with soap and warm water, including under the fingernails. Also, bear in mind that some odor may linger on your skin even after you've washed.

##  **Condoms**

Condoms—not just for penises anymore! They're also a great way to keep toys clean, especially if you're planning to share them. Condoms are a particularly good idea for toys that are porous. Porous materials like jelly rubber and softskin cannot be sanitized due to microscopic holes that can hold on to whatever they come into contact with.

Some people find that they have latex sensitivities which can cause irritation or a burning feeling. Fortunately, there are other options these days, including polyisoprene and polyurethane condoms. If you can't find them at your drugstore, check some of the sex-positive sex toy companies online. They usually have a good range of products. Using condoms isn't difficult, but there are some things you can do to make them more effective, whether you're using them on a toy or on a penis.

• Latex and polyisoprene condoms should be stored away from heat because exposure to higher temperatures makes these materials brittle and more likely to break. It's fine to stick one in your pocket when you're going on a date, but don't carry it in your wallet or keep it in a drawer near a heater.

• All condoms sold in the US have a five-year expiration date and it's printed on every wrapper. If you discover some condoms in the back of your drawer, be sure to check the date and make sure they're still good.

• Open the wrapper at the corner instead of tearing it in the middle. It's possible to tear the condom accidentally.

• If you're putting the condom on a penis, apply a little lubricant to the inside of the condom before rolling it on. Just a dab in the unrolled condom keeps the lube at the head of the penis, where it is more sensitive, and off the shaft, so it doesn't make the condom slide off.

• If you're putting the condom on a toy, roll it all the way down and, if possible, over the base. This will give you maximum coverage.

• Never use oils or lubricants containing oils with latex or polyisoprene condoms. Oils make them break. If you want to see it for yourself, blow up a condom like a balloon and tie it off. Apply a few drops of oil—massage oil, olive oil, baby oil, or any other you have handy. Rub it in with your hand and the condom will pop within a minute. (Polyurethane condoms are safe to use with oils, but they're not as sheer or as stretchy as latex or polyisoprene condoms.)

• Be sure to use plenty of lube on the outside of the condom. Since condoms have a bit more friction than other materials, you'll need a little extra help to keep things slippery.

• If the condom is on a penis, check every so often  to make sure it's still there during sex, since they can slip off, especially if the penis gets a bit soft. This is not usually a problem with a toy, since toys don't get soft while you use them. That's one of the advantages of them! And after ejaculation, hold the base of the condom to keep from leaving it behind as the penis softens.

• Throw the used condom out in the trash. Flushing it can lead to clogged pipes.

Another option that works well for prostate play is the FC2, also known as the female condom. It's a loose pouch of nitrile meant to be inserted into the vagina instead of rolled onto the penis, but it works just fine for anal play too. For anal use, first take out the removable inner ring. This ring is meant to hold the FC2 against the cervix, but it's not necessary for anal play. Be careful to insert the finger, toy, or penis into the condom rather than between the condom and the skin.

##  **Dental Dams**

Dental dams are thin sheets of latex or nitrile that are used in some dental procedures. They were brought into our bedrooms as a form of protection for cunnilingus and anal-ingus (rimming).

If you want to use a dental dam, here are a few tips. Put lube on the side of the dam that will go on your partner. Then lay the dam out over the area to be licked. The lube will not only feel nice and give your partner a sense of wetness to the  touch, but will also help keep the dam clinging to the skin, which will make it easier to keep it in place.

Dental dams are available at lots of sex-positive toy shops. You can also make a dental dam from a flavored condom by unrolling it, snipping off the tip, and then cutting down the side to form a rectangle. Another option is to use plastic wrap, which comes in many colors and can cover a larger area. Contrary to popular belief, microwavable plastic wrap works just fine—the small pores don't open until steam heats them up.

#  **HAIR REMOVAL**

Many people of all genders enjoy the appearance of a thick, dark forest on their partner's genitals. But there are many benefits to grooming your anus. Some men have especially hairy assholes—the hair can get in the way and lead to pulling during penetration. Also, the hair tends to absorb the lube that you are trying get into the hole, which means less gets where you want it to go.

To clear the path, some men choose to shave or wax their assholes. When the hole is hairless, it's easier to get the area nice and clean—both before and after play. It also allows the whole surface of asshole and perineum to be evenly stroked. And some really like the look of a smooth bottom! As an aside, lots of men are also shaving around their cock these days. Many men find that it makes their cock look bigger, which is nice for the size queens.

If you don't want the full shave or wax, you can simply  trim the hair to make it more manageable. This is a nice way to sidestep the five o'clock shadow on your tender parts. You can use an electric hair trimmer or some blunt-tipped scissors to give yourself a trim around the hole.

If your ass cheeks are hairy, you might just shave the hole and the crack, rather than shaving both cheeks and ending up looking like you are wearing a pair of furry chaps. Or, you could shave the crack and use a hair removal cream on the cheeks. Don't use these products on the hole! They can burn and irritate the skin, which is the last thing you want before playtime!

##  **Shaving**

If you choose to shave, start by trimming as described above. The shorter the hair, the easier it is to get a close shave. Make sure you have a good, sharp razor—avoid the cheap disposable kind. If you wouldn't use it on your face, don't use it on the sensitive skin of your asshole. A dull razor won't cut as effectively, which means more irritation. Red bumps and ingrown hairs are uncomfortable and none too pretty. Replace the razor regularly to make sure it is sharp.

Itching is quite common when the hair starts to grow back. This is because the hair was cut so close that it is below the surface of the skin, and it causes itchiness as it finds its way back out. To minimize the itching, and to avoid ingrown hairs, gently scrub the shaved area with a hard sponge and warm soapy water before you shave, and daily for 2–3 days afterward. This removes dead skin cells that may be blocking the hair follicles. If you shave regularly, the itching usually stops.

When choosing a shaving cream, chances are you won't find a product marketed to men for shaving pubic hair. You can try a product that is made for shaving the face—especially if it is made for sensitive skin. (The skin of the anus is very sensitive and prone to irritation.) If you apply a cream or gel and it stings, rinse it off right away and don't use it again. Likewise, if you are shaving your ass regularly and you find that your anus is irritated, itchy, or red, discontinue the product and see if these symptoms clear up.

Some men use hair conditioner or unscented lotion—this not only lubricates the razor as it glides over the skin but also hydrates the hair, making it softer and easier to cut. To maximize this effect, leave the lotion on for a minute before you shave.

When you are ready to begin, lay a mirror on the floor and squat over it so you have a clear view of what you are doing. Trim the hair if you haven't done so already. Before you apply the shaving product, note the direction of the hair growth: as with your face, you want to shave with the direction of the hair, not against it. Reaching between your legs, gently hold the skin taught with your free hand while you shave with the other. Go slowly and feel your way. Use short strokes and rinse the razor frequently to remove buildup from the cutting surface.

Resist the temptation to press hard or run the razor repeatedly over the same spot. You may not be able to get a perfect shave on the first try, but if you keep running the razor over the same spot it will probably get irritated. It is better to repeat the shave in a day or two than to go too far and get razor burn. And on that subject, if you want to be smooth-shaven for a  special night and you've never shaved before, do two shaves: once a few days before and again on the night of the date.

##  **Waxing**

Some people prefer to wax because the skin stays smooth longer: usually 3–6 weeks. When the hair does grow back, the tips are soft, since it's new fresh hair rather than sharp pointy tips of cut hair. Of course, waxing has its downside. ( _Rip!_ —Ouch!) And the angles required means that it will be very difficult to wax yourself down there.

We recommend getting it done professionally. There are many waxing salons that serve both men and women. Call the salon in advance to ask if they offer the "male Brazilian" wax. Make sure that you see someone who is licensed and who has experience working with men. The price range is generally $25–$50.

Often a Brazilian wax includes some or all of the pubic hair, the shaft, the scrotum, and the perineum, according to your preference. It is likely to hurt more the first time and to be less painful on subsequent visits as your skin gets used to it. It will hurt less if you take a pain killer one hour before the procedure.

Alternatively, you could do it at home if you have a willing friend or lover you feel comfortable asking. Home wax kits are available at most drugstores and are very affordable. However, if you are going the DIY route, do not wax your balls! The skin of the scrotum is thin and loose and doesn't generally take well to waxing. Sometimes the wax can take off a layer of skin. Most professionals, if they do wax the  scrotum, use a special wax on this area because the usual product does not work. If you want a smooth scrotum and you are going DIY, wax the rest and then shave the balls.

After waxing, expect the skin to be tender for the rest of the day following the wax, and don't plan to have any sexual activity during that time. If you've been cringing while reading this, note that while much of the hair removal may hurt, when you wax right around the asshole it actually feels rather good. Surprised? Try it. You may see what we mean.


Input:
 The prompt for the above section of the story could be:

Write a chapter titled 'Penetration 101' that discusses the importance of the prostate in anal play, but also acknowledges that there are other sources of pleasure in that area. Include information on the nerve endings in the anus and rectum and how they contribute to anal pleasure. Discuss the idea that the prostate is not the only reason why men enjoy anal play. Provide data from your survey on how often prostate pleasure is a central part of anal play.

In the second part of the chapter, discuss the basics of anal penetration. Provide tips for getting started, including the importance of being relaxed, turned on, and using lubrication. Discuss the anatomy of the anus and rectum, including the internal and external anal sphincters and their functions. Discuss the importance of knowing the shape of the rectum and how it can help avoid pain during anal penetration.

Provide guidelines for painless and pleasurable anal penetration, including starting solo, trimming your nails, using lubrication, and going slow. Discuss the importance of communication with your partner and establishing in advance what 'stop' means. Provide tips for what to do if anal penetration hurts, including slowing down, applying more lube, and removing the object if necessary.

Discuss the importance of relaxing the mind and body for successful anal penetration. Provide tips for relaxing the mind, such as eliminating distractions, addressing nagging thoughts, taking a bath, meditating, and putting aside enough time. Provide tips for relaxing the body, such as taking deep breaths, massaging the sphincters, and practicing Kegel exercises.

Discuss how to make anal penetration feel good, including being aroused before you begin, including familiar pleasures, and focusing on the ass. Provide tips for penetration techniques, such as bearing down, pulling up, and pressing down. Provide other tips, such as paying attention to the sphincters, slowing down or holding still, and starting with smaller objects and working your way up to larger ones.

Cite your sources and provide a reference for any quotes used in the chapter.

Response:
**CHAPTER** **5**

**PENETRATION 101**

#  **THE PROSTATE AND THEN SOME**

For a lot of men, the prostate is a major part of what makes receiving anal penetration feel good. For many, it is the main event, and for some it is the only reason why they go up there in the first place. But the prostate is not the only thing that makes anal penetration feel good for a man. Although in this book we focus more on the prostate and less on anal pleasure generally, we'd like to take a minute here to tell you about some reasons why going in the back door can be fun.

The anus (the puckered anal opening) has a very high concentration of nerve endings, which means that touching this area can generate a lot of sensation. Many people enjoy a variety of different kinds of touch, from very light caresses  to medium pressure. The nerves that supply the anus happen to be branches of the same nerve that supplies the cock and balls, so it's no surprise that anal stimulation can feel so good.

Once you get past the anus and into the rectum (the tube that makes up the final 6–8 inches of your digestive tract), there are fewer nerve endings, so it is less sensitive to caresses but still sensitive to pressure. A lot of people really like the sensation of being filled up and having pressure applied to the rectal walls on all sides. This is one reason why using a butt plug or being fucked with an in-and-out motion can feel good.

Even though prostate pleasure may be the focus for a lot of guys, we've heard from men who have had their prostate removed for the treatment of prostate cancer and still love to have their bottoms poked. They report that their sensation is reduced, unfortunately, but that it is still pleasurable. This points to the fact that the prostate is not the only source of pleasure in that area: the nerves of the anus and rectum also make their contributions.

**FROM OUR SURVEY: "NOT ALL ANAL PENETRATION IS FOCUSED ON STIMULATING THE PROSTATE. HOW OFTEN IS P-SPOT PLEASURE A CENTRAL PART OF YOUR ANAL PLAY?"**

"Not often."

"All of it."

"Most anal play includes prostate play."

"More of a warm-up to other things. Strap-on and such. But in all anal penetration you will rub the P-spot some during the act."

"More on the foreplay portion of my play. But it is clearly part of all anal play."

"Some of my anal play is external and focuses on stimulating the erectile tissue around the opening. Whenever anal play includes penetration, P-spot pleasure is very central."

"When engaging in anal play, I always make some attempt to stimulate the prostate, and then see how the person responds. Sometimes they enjoy it, other times it seems to be too much sensation for them or they have no significant response, so I move on to other activities."

"I don't know if I've reached my P-spot or not. Either way it feels great."

"A quarter of the time it is the focus, but it usually is stroked right before and during orgasm."

"It hasn't really been a focal point of the anal play I do; mostly, if I've stimulated the prostate at all, I've done it by accident."

"Always important, not usually the sole focus."

"Always. In fact if it doesn't involve prostate play then it's not interesting /fun/pleasurable to me."

"About half of the time."

"It's the only anal play."

"Always...as a way to open up the asshole for further fucking...and just on it's own...finding the sweet spot with my fingers."

##  **Getting Started**

When you are first starting off with anal play, your body is learning two new things: how to physically relax the anal muscles, and how to receive this stimulation as pleasurable. Like anything else that's unfamiliar, you might not get it right away. Your first few anal experiences may feel unremarkable. In fact, it is common for there to be some discomfort the first few times.

Being turned on usually makes anal play a lot easier and more fun. The more turned on you are, the more your brain is likely to interpret new sensations as enjoyable. In fact, you might try starting your exploration of anal penetration by including or even focusing on some other kind of stimulation, such as masturbation or oral sex. Some people eventually find anal play (internal and external, with or without intentional prostate stimulation) to be a pleasure all by itself. Others prefer it as an add-on to their favorite way to play. Either way, as long as it's feeling good, go for it!

An entire book can be written on anal penetration—in fact, there are quite a few. So here we only cover the basics. See the Resources for a list of how-to books and DVDs about anal play.

##  **You Need a Map!**

If you're going to go looking for the prostate, you need a map of the surrounding territory.

First things first: the anus. This is the puckered, pink circle that forms the anal opening. Under the skin are the anal sphincters: two rings of muscle that separate the rectum from  the outside world. You can think of them as two donuts, one on top of the other. When you slip your finger inside, you are sliding it through the donut holes.

The "upper" donut (the one closer to your head) is called the internal anal sphincter. It is continuous with the involuntary smooth muscle of the intestines. The "lower" donut, the external anal sphincter, sits underneath the internal sphincter, but it also comes up and around it and connects to other muscles of the pelvis. The external anal sphincter is a part of the PC group, the group of muscles that convulse rhythmically during orgasm.

The ring formed by the sphincters opens up when they are relaxed and closes in when they are flexed. Since the sphincters are each made of a different kind of muscle, they work a little differently when they relax and tighten. The external sphincter (that's the lower donut in the stack—the one closest to the outside of your body) is made of skeletal muscle. That means that it can be flexed and relaxed voluntarily, like your hand or your foot. The internal sphincter (the top donut) is an entirely different matter. Since the internal sphincter is continuous with the smooth muscle of the digestive tract, it is controlled by a subdivision of the nervous system that is not under voluntary control, just like the rest of the intestines. This can sometimes make it difficult to deliberately relax it.

If you are in a truly relaxed state and you allow the external sphincter to open, the internal one often follows suit. But you can't fake it, because your involuntary nervous system knows whether or not your interest in being penetrated is sincere. If you are nervous or anxious, the sphincters tend to tighten  up—your body doesn't care if the reason you're stressed is because you were stuck in traffic, you had a busy day, or you're nervous about anal penetration hurting. Fortunately, with a little practice, it usually becomes easier to encourage the internal sphincter to open up.

Once you get past the anal muscles, you're in the rectum. You'll notice it's much roomier here. The rectum is an expandable tube with thin, soft walls and gentle folds, and it's lined with a mucous membrane to protect the delicate tissue. Because of the lining, it feels moist to the touch, though there isn't usually enough moisture to allow comfortable penetration without lube.

It is important to know that the rectum is not straight. Quick exercise: grab a piece of scrap paper and draw an _S_. Make it a very tall, thin _S_ so that the curves are soft, as if the _S_ is being squeezed in a vise from left to right. Now hold the paper up to your right side. You are now a cutaway diagram of the rectum! Viewed from the side, this is roughly the way the rectum curves: from the anus it moves first toward the belly, then toward the back, and finally toward the belly again.

Why is this important? Because, as Jack Morin points out in _Anal Pleasure and Health_ , if you are aiming too far toward the front of the body as you go in deeper, you may run right into the first curve. Poke!—ouch. This is especially relevant to prostate play, since when you are looking for the prostate you are aiming toward the front wall of the rectum.

This tends to be less of an issue with fingers, which are shorter and can easily feel where they are going. With a cock, a dildo, or other toys of significant length, it is much easier to  bump painfully into the first curve, especially if you are doing short strokes right over the prostate and then suddenly plunge deeper. To avoid this, go slow when you are moving deeper and adjust the angle so that you are not pointing too sharply to the front of the body.

#  **PENETR ATION: THE BASICS**

Whether you're on your own or with a partner, here are some useful guidelines for painless and pleasurable anal penetration.

##  **Start Solo**

If you are new to receiving anal penetration, we recommend that you fly solo for your first few tries. Even if your partner is quite experienced and skilled, doing it by yourself allows you to get comfortable with the new sensation in a pressure-free environment. You can focus entirely on yourself without distraction or performance anxiety. This should also alleviate concerns about "the mess."

It can be really helpful to play with your own ass before you play with someone else's! Everyone has an asshole—men, women, cisgender, transgender, genderqueer—we've all got'em! So no matter who you are or what your orientation, you can play with your own bottom and it'll make you better equipped to pleasure someone else's, since you will know how it feels (ahem) firsthand.

##  **Trim Your Nails!**

You'll also want to make sure that your fingernails are short and smooth. Run them along your lips to check for any rough edges and file them down as needed. Gloves can also cover up any rough spots. If you have long nails that you want to keep, tear some cotton balls into thirds or quarters and stuff them into the fingers of a glove with a pencil. When you put the glove on, push the cotton under the tips of your nails. You won't get as much sensation, but you'll protect both your partner and your manicure.

##  **The Importance of Being Lubricated**

The rectum does not self-lubricate, and without lube, anal penetration can be uncomfortable, painful, or even injurious. With lube, it will feel slick and smooth, plus it's a lot safer for the delicate tissues of the rectum. Even if you think there's enough, put a little more on your fingers and apply it to the anus and rectum.

One of the functions of the rectum is to absorb water from your waste and back into your body, so if you're using a water-based lubricant, it will dry out after a while. Tell your partner when things are getting sticky, so you can apply more lubricant. With some brands your partner can add a splash of water to rejuvenate the dried-out lube. There are a lot of different kinds of lubricants these days, so we've written much more about them and how to pick one. See chapter 11, Toys, for more information.

##  **If It Hurts, Don't Do It!**

If you experience any pain, stop what you're doing and don't force it. You could hurt yourself. If your body isn't ready for more, listen to it. Even if you're experienced with anal play, your body sometimes might not be into it.

Some men ask about desensitizing sprays or creams. Others may use drugs or alcohol to dull the pain. We do not recommend this. While we don't think it's a problem to have a drink or two, if you're not in a state of mind where you can pay attention to how things feel or tell your partner what's going on, it's probably a good idea to hold off on prostate fun for another time. Pain is an important warning sign of potential damage, and if you can't feel pain, you are at risk of hurting yourself without realizing it.

Rather than trying to cover up or push through the pain, it's actually much more effective and a lot more pleasurable to learn how to relax the pelvic floor. After all, if you're turning off the nerve endings so you can't feel pain, you are also turning off those same nerve endings to the good sensations, which are the whole point in the first place! Is it any fun to kiss someone after getting a shot of Novocain at the dentist?

Some sex educators seem to suggest that anyone can have pleasurable anal penetration, but in our opinion, that's simply not true. For example, sometimes a previous injury or trauma makes penetration uncomfortable or painful. If that's your experience, perhaps the best way to keep anal play from hurting is not to do it. There are plenty of other fun ways to enjoy sex.

On the other hand, quite a few people who have had unfortunate experiences that made anal penetration painful have discovered that by going slowly and carefully they can turn that around. Whatever your situation, if it hurts, something needs to change. There are a lot of things you can do to ease pain if it arises.

#  **IF IT HURTS**

• Slow down or stop the motion. If you're not already on your back, lie down, relax, and take several deep breaths, then see if the sensation passes. If your partner is controlling the motion, make sure to establish in advance whether "stop" means "hold still" or "pull out."

• Introduce something pleasurable, like stroking your cock. Adding familiar pleasures to the experience makes it easier for your body to decide that anal play feels good. This, in turn, may spark a stronger desire to be penetrated, and that can help the muscles of the pelvic floor release.

• Apply more lube to reduce friction.

• If you've inserted an object, remove it and give your ass a break. Be sure to remove it slowly and exhale as you withdraw: even if it hurts, going too quickly can make it hurt more.

• If the object is too big, scale back to a smaller object.

• If none of this helps, call it a day and move on to some other kind of stimulation. Sometimes anal play just doesn't work, but that doesn't mean you can't do it again another day.

#  **SLOW AND STEADY WINS THE RACE**

_"Ironically, going slowly gets you in faster."_

**—CHARLES SILVERSTEIN AND FELICE PICANO**

Remember the lesson of the tortoise and the hare: slow and steady wins the race! It is important to pace yourself as you explore anal penetration. Negative experiences can set you back further than if you had taken your time in the first place. Rushing can lead to discomfort or pain, which can turn your body off to the sensations and make it less likely that you will feel pleasure: "In general, subjecting any area to pain will cause a tightening, an internal withdrawal of feeling from that area. This will result in a numbness and desensitization of that area." 12

For your first few times, don't go too far too fast, even if it feels good—you may have a sore bottom tomorrow. Don't dive in the deep end with rapid motion or very large objects. Sex educator Tristan Taormino suggests two fingers for first-time anal penetration, and we think this is reasonable. Of course, it depends on the size of the fingers— one might be plenty enough, and that's perfectly fine.

_**"Sometimes anal play just**_
_**hurts, and that kills the prostate**_
_**pleasure."**_

Some people believe that anal penetration is always painful and that the only way to get to the pleasure is to push through the pain. This is not true! Many, many people regularly experience anal penetration that feels good the whole time and doesn't hurt.

If you stop what you are doing and let the pain subside, you may be able to find the pleasure you are seeking. In most cases, pushing through the pain only makes it hurt more. And taking the pain today will make it even harder to have pain-free penetration next time. Your ass will remember.

In his book _Anal Pleasure and Health_ , Jack Morin explains how memories are stored in the body. Painful memories translate into muscular tension, so the only way to relieve the tension is to slowly replace the bad memories with good ones. You can't do it by creating more bad ones.13

We interviewed a man about his experience receiving penetration. We asked, "Was it ever painful for you?" and he said, "Sometimes, yeah. But I also have a high pain tolerance and don't mind pain." Interestingly, he was someone who had never found pleasure in anal penetration and had turned away from it. The point is: maybe you can take the pain, but we'd be willing to bet that it won't do you much good. Once it starts hurting, it is unlikely that the pain will give way to pleasure if you push through it.

_**"I used to believe that there**_
_**would be the pain at first and**_
_**then it would slowly become**_
_**more pleasurable after that, but**_
_**I've since realized that if you**_
_**gradually work your way into it,**_
_**it's fun times the whole way."**_

##  **Relax the Mind**

Anal play definitely works best when you're in a relaxed state of mind because our emotions affect our physical states. If you have a mental block such as a nagging anxiety repeating in your head, or if you're stressed out from a busy day, it can trigger muscular tension.

Do you ever grit your teeth when you're stressed? Well, the jaw is not the only place where people tighten when feeling anxiety. Many people also squeeze their pelvic muscles, including the anal sphincters. This is why someone who is uptight may be called "anal-retentive" or a "tight-ass." Men especially are prone to keeping their pelvic muscles and anal sphincters overly tight. If your sphincters are clamped shut, it will be more difficult to get in there.

To help yourself relax mentally, eliminate distractions as much as possible. If you have nagging thoughts that are pulling you away from the experience at hand, put them to rest by addressing them. Worried someone is going to come in? Lock the door. Afraid the roommates will hear you and they'll _know_ what you're doing? Put on some music.

It may help ease your mind to take a bath or meditate. Put aside enough time so you aren't rushed, and make sure you have everything you need before you start. You might gather lube, a drip towel, gloves, something to wipe your hands with, toys, and a towel to lay on the floor for your discard pile.

Above all, take it easy. Try not to try too hard. We've spoken with men who treated anal penetration and the search for the prostate like a desperate climb for a fabled treasure at the top of a mountain. They would try and try, and then wonder why  it continued to elude them. With so much mental energy and effort, no wonder they weren't enjoying themselves!

If this is you, you may benefit from an attitude adjustment. Instead of trying to make your play conform to your expectations, release the impulse to control and let each moment be what it is. As is often the case with sex, sometimes it's easier to get what we want when we let go of reaching for it.

##  **Breathe Deep to Help You Relax**

The way you breathe can literally change your state of mind and body. Taking short, shallow breaths is what we do in "go" mode, the activation state of the body, so breathing that way tends to put you in an active head space. Deep, long, easy breaths tend to put you in a state of relaxation. Intentionally regulating your breathing by softening it and relaxing it actually makes you feel more relaxed. And that makes it easier to let the sphincters open to allow penetration.

Breathe deeply and slowly to relax. Make sure you do a complete inhale _and_ a complete exhale. Many men, told to breathe deep, take a deep breath in and hold it. Holding your breath takes effort! We're going for less effort and more ease.

It's not just about taking in a lot of air on the inhale—it's about releasing it on the exhale. The exhale is the more relaxing part of the breath. In fact, if you pay attention, you may be able to notice your anus tightening a bit when you breathe in and relaxing as you breathe out.

There's also a common tendency, when told to exhale, to push the air out forcefully. Again, that's effort. What you want is less effort, more release of effort. Try letting it out  softly and smoothly, as if of its own will, rather than pushing it out forcibly.

Many people find that the initial penetration works best when they exhale at the same time. Take a slow, deep breath and then slowly let it out as the finger or toy enters your anus. If you're doing it with a partner, breathing together can be a great way to sync up, feel connected, and ensure that the giver is paying attention to the receiver.

##  **Relax the Body**

To allow something inside your ass, your sphincter muscles need to relax in order to open up. A lot of people believe (mistakenly) that when you enter the ass, you gain access by stretching the sphincters like a rubber band. This may be the origin of the myth that anal sex will put you in adult diapers: that by stretching them over and over, they will become overstretched and, also like a rubber band, lose their elasticity and their ability to bounce back to the original state of tension. In fact, plenty of people have been playing with their asses for years without losing sphincter tone or control.

Of course, the sphincter muscles do stretch, like any other muscle, and they may receive some stretch during anal penetration, particularly if they tend to be tight. Just like other muscles, the anus is capable of increasing its flexibility over time. This is why people who have lots of anal experience can accommodate larger objects. But, as with those other muscles, you can strain it if you try to stretch it more quickly than it can handle. One sex educator we know compared this to learning to do a split in gymnastics: you wouldn't expect to  do it all in one day. Rather, you'd practice regularly and each time you'd be able to go a little lower to the ground. It's the same with penetration. You may not be able to take larger objects right away, but you might eventually, if you increase your flexibility gradually over time.

Relaxing the sphincters is harder than it may sound. We are used to thinking that we have complete control over the actions of our muscles. If you want to flex your hand to make a fist, you do it, and if you want to relax it, you do it, and it's easy. But most people have had a lot more practice flexing and relaxing their hands than their anal sphincters. Chances are, the sphincters are accustomed to releasing only when necessary for a bowel movement. Otherwise, they are held closed by their muscular tone, and perhaps even locked down if you have over-tight muscles. So, it may take some practice to learn how to relax them.

Then again, relaxing the sphincters may come easily to you, especially if you have good muscular awareness. We met a fellow who had only done anal play two or three times before, and he was able to take three fingers like a sip of lemonade because he had done lots of yoga and was very well in touch with his muscles. But for many of us it will not come so easily.

You might find that your brain says to your ass: "please open," and your ass completely ignores this message. It may take a while for you to learn how to convey that relaxation message thoroughly to your ass. A lot of people get in a bind here because they want to relax so they try, try, try. And, ironically, the harder you try, the less likely it is to happen,  because trying hard is the opposite of relaxing. Instead, try letting go of the ambition.

##  **Massaging the Sphincters**

A good way to get any muscle to relax is to massage it. This applies in a most pleasurable fashion to the sphincters. Before penetration, rub the sphincters softly with lube. You can trace a fingertip in a circle along the ring, or rub up and down over it. Try adding pressure or touching more lightly. You can press-and-release over the whole surface, or rest your finger gently in the middle of the opening, without pushing in.

This kind of attention not only helps the muscles relax, but also feels amazing. The teasing, lingering touch on the outside makes the ass crave penetration and also helps you relax mentally because it feels much less threatening to the hole than a clambering rush for entry. It reassures the ass that you are going slow and taking your time. Soon, the ass is not only relaxed enough for penetration, but begging for it!

It is easy to blast past this phase in your eagerness to plunge deeper and get to the prostate already. However, you do yourself a disservice if you skip this step, because it can be extremely pleasurable and can make what comes later even more enjoyable.

##  **Learning to Relax the Sphincters**

As with all new skills, learning to relax the sphincters comes more easily with practice. Most people find that the more often they practice, the easier and faster they can open up. Conversely, if you go for a while without doing anal play, it  can take some time to build up the ability again. So expect to take your time if you haven't done it in a while.

Practicing Kegel exercises also helps you gain control over the sphincters. (See chapter 6, Searching for the "Magic Button.") This may seem counterintuitive. The purpose here is not necessarily to strengthen the pelvic muscles; it is to get them toned. When they are toned they are both strong and supple, and they can relax just as easily as they can tense. Getting your PC muscles in shape helps you get in tune with the sphincters and gives you better awareness of them, which will make it easier to relax them.

Try inserting your finger (with lube, please) just a little way into the sphincters and squeeze them so they tighten around your finger. Then give just as much of your attention to relaxing them. Repeat several times, making sure to spend as much time on the release as on the tightening.

#  **MAKING IT FEEL GOOD**

You can't just shove something up there and expect it to feel good. (Though if you've been doing this for a while, maybe you can!) When you are trying to get into something new, it helps a lot if you are aroused before you begin. The more turned on you are, the easier penetration can be and the better it'll feel.

Include familiar pleasures. Play with the cock, balls, perineum, thighs, nipples, or whatever else gets the fire burning. Allow your thoughts and fantasies to wander where they will without judging them.

Focus on the ass, stroking it at a slow, leisurely pace. Give the cheeks some attention. You can rub them and squeeze them and gently pull them apart. If you are playing with someone else's ass, jiggle the hips from side to side with your hands, like a massage therapist, to help the muscles of the pelvis relax.

When it's time for penetration, don't just shove in—give the outside some love. Remember what we said about sphincter massage? Use your finger or toy or cock to lavish affection on the hole before entering. Some people like to use their mouths for this—this is called rimming.

When you are ready to slip inside, go very slowly and gently. The sphincters should relax open to allow penetration. You can apply some pressure, but you shouldn't force your way in. Once inside, don't jump straight into movement. Let the ass adjust to being penetrated by holding still for a spell.

You may wish to keep cock play going at the same time. This is a great way to make anal penetration feel good when you are still learning to eroticize it. However, rubbing the cock can make the PC muscles—including the anal sphincters—tighten as a result of the excitement, which makes initial entry difficult, so you may want to let go of the cock for at least a few minutes at the moment of penetration.

##  **Penetration Techniques**

There are a few different techniques for getting an object inside you.

• Bear down: With the penetrating object at the opening of your anus, bear down while exhaling, as if having a bowel movement. This opens the sphincters, and you can then slowly let it in.

• Bear down, pull up: Same technique, except this is for those with good PC muscle control. Bear down to let the object in a little, then pull up and in with your PC muscles, so that you are sucking the object into you. Repeat until it's in past the sphincters.

• Press down, slip in: With your fingertip at the hole, push down on the sphincter to hold it slightly open. Imagine the anus as the face of a clock, and press gently at six o'clock to stretch it just a little bit. Release the pressure as you slip in.

##  **Other Tips**

If you're using a finger, you'll be able to feel both sphincters. One might be tighter than the other, so go at the pace of the one that's slower to open up. It's more likely to catch up that way than if you try to get it to do more than it wants. Help the sphincters release by _gently_ pressing up, down, right, left, to stretch them and encourage them to open.

If you're moving the toy or finger in and out, pay attention to how the sphincters contract and release. When they  contract, slow down or hold still. Stroke the cock, massage the perineum, or do something else that feels good. When they release again, you can return to the motion.

Sometimes, even once you get going, it's nice to slow down or even hold still for a few moments. There's an idea in our pleasure culture that more stimulation means more pleasure, but that's not always so. After all, a lot of people enjoy butt plugs because they create a feeling of fullness or pressure without an in-and-out motion. More movement isn't always better.

You might find that one part of the anus feels especially tight or sensitive. Since there are a lot of pelvic muscles, tension in any of them can make relaxing the anus difficult. Gently but firmly press on the area that feels tight and hold the pressure for about 60 seconds. This often helps release the tension more easily than with a more vigorous massage.

Always start with smaller objects and work your way up to larger ones. Fingers are convenient because they come in so many different sizes! You can start with the smallest finger and increase in size. Anytime you change to a wider finger or toy, or add a finger, apply some lube and exhale as you slide it inside, then hold still for a moment to let the ass get used to the new object.

SOURCE OF QUOTE

Charles Silverstein and Felice Picano, _The Joy of Gay Sex, 3rd ed_., fully revised and expanded (HarperCollins, 2003), 92.