The Ultimate Guide to Fellatio (23 page)

With the flat of your finger, or fingers, press lightly on the opening and hold it there. Increase the pressure a little, massaging and pressing in circular motions. Go very slowly, and listen to his cues or verbal instructions—for some, simply having their anus touched is all it takes to push them over the edge. Pay attention to lubrication, and never rely on saliva. In porn films they make it look like that’s all they use, but that’s not the case—they just don’t show you the anal suppositories and numerous applications of lube.

Move your flattened fingers in a circular motion, and begin experimenting with penetration by pressing one well-lubed finger at the base of the opening (toward his tailbone). Massage the opening’s base, and ask him if he wants you to go farther. Slowly slide your finger in up to the first joint (about an inch), and hold it there for a few breaths. You’ll feel the ring of muscles around his opening squeeze and contract—just stay still as the muscles relax.

When you feel the muscles relax, slide your finger in slowly a little bit more, then back out, doing a gentle in-and-out, not all the way in yet. Once again, this may be all it takes for him to come, or to decide that it’s not what he wants right now—but if he does want more, following his directions and body language from here, you can progress to more stimulation. You can go deeper or faster, or even add more fingers—but the rule of thumb is to do everything so slowly that you can practically feel the seasons changing around you. Anal penetration hurts when you go too fast, you don’t use enough lube, the recipient isn’t relaxed, or he doesn’t really want to be doing it.

Once he’s anally warmed up and ready for more penetration, you can bring anal sex toys into the picture. Sex toys used for anal penetration must have a flared base, meaning a base that prevents them from being pulled into the anal canal, where they can get lost—a nightmare waiting to happen. The sphincter muscles have minds of their own and like to squeeze and contract at will; we cannot control them. This serves to push and pull things in and out of the anus, and once something gets pulled in, there’s no guarantee you’re going to get it out without a trip to the hospital—which is what you’d have to do to prevent serous injury if, say, a hot, battery-powered vibrator went AWOL. Take a look at a standard butt plug and you’ll see exactly what a flared base should look like. Buy toys that are safe for anal use, and don’t get cute with carrots.

Vibrators can feel fantastic on the ass during fellatio, and you can tease and penetrate while you suck. The thing to know about vibrators and anal stimulation is that the outer third of the anus, and the prostate, contain more nerve endings than the anal canal and respond best to touch and vibration. The inner portion, inside the canal, has fewer nerve endings near the skin’s surface and responds to feelings of fullness, pressure, and rhythm.

So, a vibrator will feel intense (intensely good) around the opening and the prostate area. But the vibration won’t be a factor deep inside—the size, shape, and motion of the vibe will. To maximize your buzz, select insertable vibrators that have the vibration located at the base. When bringing a vibe into the action, start on the lowest speed, and give him more as he asks for it.

Squirt liberal amounts of lube on any toy you use, and reapply frequently. You can fuck the daylights out of him anally with a dildo he likes. Or, insert a butt plug and keep it in place while you suck and bring him to orgasm; just don’t leave it in for extended periods, or it will get downright uncomfortable. Chances are good that his PC muscles will squeeze the plug out before he orgasms; if you like, you can hold it in place with your free hand. It can also get forced out during orgasm, which is an okay way to remove it. But if it’s big and stays in place, after he comes ask him to take a few deep breaths and let him know you are going to remove the plug on an exhale—then remove it on the second or third exhale.

The Prostate

In men, anal stimulation and penetration can crank up the arousal for a variety of reasons, some psychological and some physical. One big, or little, reason is that rising star on the stage of sex play, the prostate gland. Much ado has been made about the prostate, and this tiny celebrity of the glandular glitterati doesn’t show any signs of slowing down as men and their partners discover the erotic potential of prostate stimulation.

In most every sex book you’ll pick up, if you can find a reference to the prostate gland at all (without it being exclusively related to cancer), you’ll notice a few strange things about the way authors tend to deal with the subject. Some impart a homophobic tone that makes even me wonder if I’m repressing anything—and this goes for both male and female authors. It’s as if they wanted you to be absolutely sure they’re straight when they’re telling you about what’s inside guy’s butts, and that you are too, and that everyone’s still straight after they read about it. The concept of male anal penetration obviously carries a lot of stigma and shame for these authors. This would be funny, if it weren’t so frustrating trying to get information out of their texts. The other unfortunate thing most books do when they cover real-life, try-this-at-home prostate stimulation (which is rare) is rush through the material and present it in a cold context, as if no one would really try this during sex. The gay guides are straightforward and enthusiastic, but there aren’t many of them available. And the straight manuals never suggest that the man try to find the prostate for himself—especially during masturbation, which is something I highly recommend. Oh, and did I mention that prostate play, or the enjoyment thereof, has nothing to do with sexual orientation? It doesn’t. End of discussion.

The prostate gland is located at just about the center of the male urogenital system, inside the perineal wall. It sits just below the bladder, producing the fluid that mixes with semen in ejaculate, and is connected to the urethra, the muscles that line the perineum, and the sphincter muscle. If there’s an epicenter to male orgasm, then this must be it. For a thorough understanding of prostate anatomy and location, see chapter 2, “The Anatomy of a Man’s Pleasure.” Many men, though not all, find that when they’re aroused, prostate stimulation is intensely pleasurable; that’s because the nerve pathway form the brain to the penis runs through the rectum, and one large nerve bundle is located just beneath the prostate. Additionally, the root of the penis is more or less anchored at the prostate, so when you massage the prostate you also transmit sensation to the base of his penis.

The gland is rounded, shaped like a walnut, but slightly cleaved down the center so it has a furrowed seam and two subtle halves that can be felt with the pad of your finger (when touched from inside the anus). In size it can be anywhere from the size of a small chestnut to a large walnut, or even larger in men over forty. When he’s aroused, it swells and becomes firm to the touch, and it’s a lot easier to feel it. Plus, it’s much more fun to touch when he’s hot and bothered.

Begin your prostate explorations when he’s good and ready; the prostate is easier to find when he’s aroused, and he will enjoy the touch more at this point. You can stimulate his prostate externally, through the perineum, or internally, by inserting a finger, dildo, or butt plug into his anus. External stimulation is done by massaging or applying gentle pressure to his perineum, on the area near, but not on, the anal opening. See if he likes this; not all men do, and some might find it downright uncomfortable. Try vibration, and see how that feels, too.

Penetration is the most direct way to stimulate the prostate. The preceding section has all the information you need on the importance of lubrication, patience, communication, and safety—follow the rules! But prostate stimulation differs slightly, because you focus your attention on the gland rather than on the fullness, pressure, or rhythm you’re applying to his rectum. When he’s aroused and ready for penetration, take the necessary steps to pleasurably insert your finger, then slightly curve it toward the front of his body: facing him (perhaps with his penis in your mouth or other hand), make a come-hither stroking motion with your finger. Don’t poke, push, or stab forward. The gland is delicate, and because of its positioning, some men report the sensation of having to pee when it’s stimulated. That’s a feeling that some men don’t like at all, and you may wind up switching activities if he’s uncomfortable. If he experiences any pain when his prostate is touched, he should have it checked by his doctor.

Apart from possibly making him feel like peeing, touching his prostate will certainly make him feel a fullness and pressure that he can feel in his penis. Juicy men who are prone to leaking pre-come may leak a little more when you massage their prostate; that’s because the prostate is where the fluid comes from. Massage it gently but firmly; you can simply move your finger in the come-hither motion, or you can keep your curved finger stiff and move it in and out. As he gets close to orgasm the gland will swell more, and it will get quite hard before he ejaculates. The orgasms from prostate stimulation are often described by men as deep, intense, and powerful.

Rimming

Rimming, or analingus, is kissing, caressing, or penetrating your lover’s anal opening with your tongue. For many people, rimming is a delicious experience, on both the giving and the receiving end. Some say there is nothing as arousing as having their lover’s warm, soft tongue and lips give them pleasure in such an incredibly intimate place, and those who love to give it find the experience equally arousing. Also, the feeling of doing something taboo or “dirty” heightens the experience for some. Because the delicate pucker of the anus is packed with sensitive nerve endings, rimming can be all it takes to push someone over the orgasmic edge.

For men, rimming adds a new spectrum of pleasure to the sexual experience. A fantastic blow job can include delicate licks and flutters of the tongue on and around the anus, and rimming can be a great introduction to the sensation of anal penetration. For men who enjoy being penetrated, this is a delicious tease for the main course to come, and for men who aren’t sure about penetration, rimming allows them to comfortably try out the sensation of anal stimulation to see if they might like it.

The easiest position for rimming is doggie-style, with the rim-ee on all fours. This lets you gently spread his cheeks with your hands, and see everything clearly as you dip your tongue in and out. If he has a lot of hair down there, this position is optimal for parting the furry seas—and if this notion makes you uncomfortable, let it be known that
everyone
has hair down there. If you do not naturally have hair around your anus, you are either a) too young to be reading this, b) shaving or waxing it, or c) a genetic anomaly. Doggie-style licking is ideal because it also provides a fantastic rear view of his testicles, which you can squeeze, rub, and pull on as you lick. Also, you can pull his erect penis back between his legs for reverse cocksucking, though some men find this uncomfortable. When in doubt, ask how it feels.

With the delicate pucker of the anus in full view, gently kiss and lick his cheeks as they slope inward toward the crack. Work your way closer into the furrow, taking your time to let him get used to the sensation—or to tease him if you know he likes it. You can make your first touch in various ways:

• Lick the entire furrow from top to bottom as you would an ice-cream cone, with a big, flat tongue.

• With softened lips, kiss it directly, over and over.

• Press your flattened tongue against the opening and hold it, then slowly start to move it in up and down, or give him an in-and-out massage.

• With the very tip of your tongue, lightly lick in a ring around the rim of the opening—“rimming” him.

You can start with one of these and then try them all out to see what he likes. When you find something that makes him moan, groan, and push his butt in your face, stay with it for a few minutes. Gradually, work your tongue into a rhythm with a short, firm lick. Continue the beat for a while: this should get him pretty aroused. If you decide you want to go a step further, begin darting your tongue in as you lick, graduating to what’s called “tongue-fucking.” Moan your appreciation and see how he responds—moaning vibrates your tongue and simulates a vibrator. When you want him to explode, slide a lubed hand onto his cock and jack him off while you lick—there’s no sensation in the world like it.

A man with lower back pain or mobility issues can simulate the doggie position by lying on his stomach with pillows under his hips, comfortably raising his butt for optimal licking. Having him lie stomach-up with pillows under his butt is also an option, though you have to spread his legs quite wide for access. In this position, placing pillows under his knees can help ease strain on his back. Lying sideways may be comfortable, too; he’ll want to put a pillow between his legs for the lower back, and the pillow will also serve to keep his legs slightly spread—though he may eventually end up on his stomach as you pull his cheeks apart.

Cleanliness is often the number one concern for would-be rimmers and rim-ees alike. Taking a nice long shower or bath beforehand is always recommended, and you can bathe together to make it part of the seduction. If your partner is reluctant because of cleanliness issues, begin rimming in the shower, where you’ll both make everything squeaky-clean. Men who are comfortable with enemas can have one before showering and know they’re clean from the inside out.

Flavored lubricants are an option for people who want to try rimming but shudder at the notion of tasting their lover’s natural flavors, though they come with several caveats. Flavored lubes taste awful, even the lime, kiwi, or piña colada versions. Because they’re packed with sugar, they are not an option for diabetics or other people who don’t tolerate the effects of sugar well. But they do their job to some extent, transforming the eager anus into an artificial-raspberry-smelling orifice. Just be sure to never, ever purchase lubes that advertise “anal ease.” Most lubes sold specifically for anal use contain large amounts of numbing agents, such as benzocane, which diminish sensation and will leave you with a numb tongue. They’re manufactured by an industry that believes anal penetration of any kind is painful—when in reality, anal penetration isn’t painful if you do it right. If it hurts, then something’s wrong, and you don’t want to mask important signals the body might be trying to send. Besides, who wants a numb butt?