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.