Group of boys
Here are some basics that the boy in your life would like you to know. Maybe it’s awkward for him to tell you - maybe there even are some things he hasn’t discovered yet.
Let’s begin at the end: the glands. This is the very sensitive end, or tip of the penis. It’s covered by the foreskin in boys who aren’t circumcised. The glands looks and feels unlike skin on any other part of the body: it is soft, squishy, and the home of the most intense and delightful feelings a boy can experience. It is so sensitive that the feel of, say, a stream of water from a showerhead may be too intense to stand for more than a few seconds. Yet for all its sensitivity, stimulating the glands alone usually does not lead to orgasm - you need to massage some part of the penis shaft as well.
This means, if you know what you are doing, that you can give very extended pleasure by massaging the glands. It is so soft that unless it and your fingers are completely squeaky clean most likely any petting will soon become irritating. What your guy really wants is a moist massage, either with saliva or another lubricant. The simplest and one of the greatest
treats you can give him is to moisten your thumb and slowly rub it back and forth across the head of his penis.
You can do this for ten minutes, twenty minutes, and watch him drift into a plateau of pleasure, without the tension of an approaching orgasm.
Of course, you can do the same with your lips, though it is almost impossible to resist the temptation to take more of he penis into your mouth - and then you’re off to the races!
If you’re this close you can see some of the unique geography of the glands.
First, it has a grain - small ridges that go fore and aft (away from his body, rather than side to side). It’s usually more comfortable to pet with the grain, though if you are using lubrication it doesn’t much matter.
Second, there are distinct regions on the glands: the very tip, around the urethra opening (‘pee hole’); the twin bulges on the front, separated by a small cleft; the broad, flat back; and the flared bluish ring where it connects to the penis, called the corona. The most sensitive parts are the tip and front. Try gently massaging the front, spending five or ten seconds on each side, then switching, then spending an equal time on the very tip.
The back is the ‘grainiest’ region and should be petted front to back. The tip, just behind the urethra opening, is the best place to get started - a very good erection stimulator!
Notice that all this is about stimulating the skin of the glands. It is a soft and delicate region and not meant for deep massaging - too much pressure doesn’t exactly hurt, but it isn’t so delightful, and in fact a good squeeze to the glands is one technique for bringing down an erection.
It really is possible to give very extended pleasure to the glands alone.
This may be very relaxing for your boy, or it may make him desperate for more - it’s a matter of mood! Once you do start to involve the rest of the penis, things change quite a bit.
Just below the glands on the penis shaft front is the main action area, the part that is most involved with the intense feelings that cause orgasm and ejaculation. The penis itself really has two parts, the raised part on the front through over the urethra, and everything else (sides and back). While we enjoy stimulation to any part of the penis, it’s the front that is the
seat of pleasure. Petting or massaging the back of the penis doesn’t do very much.
The top inch of the front of the penis is the trigger, the part that all boys first learn to rub when they masturbate, either by an up-and-down motion (the veritable “jerking off”), or by rubbing side to side. This part of the penis is sensitive to pressure, rather than surface petting. Once a boy is fully aroused, even a slight pressure to this part of the penis will lead up to orgasm. If you are using your hands or lips on his penis, it’s up to you to be sensitive to how much stimulation you are applying here, as that controls how long the ride will last!
Pressure to the top front of the penis doesn’t have to be applied directly, and this is where the rest of the penis gets involved - and a whole lot more. Once an erection is full grown, the penis is stretched tight, which means any pressure along the front or anything pulling at the base will tug on the top part just as surely as if you were massaging that part directly.
This is something that grows more intense as he comes farther along towards orgasm: after a few minutes of stimulation, with his penis rock-hard and pumping from within (more on this later), even a small tug on the scrotum at the base of the penis can trigger an orgasm.
If you are using your hands, you can continue to massage the glands while stroking or gently rubbing the front of the shaft. Of course, if you are using your mouth or taking his penis into your anus, all this happens automatically - it’s exactly what the penis was designed for, and his whole body will get involved to make sure there is an orgasm soon! But let’s not hurry, please, you have a lot of delightful territory still to explore. With his penis at ‘full attention’ you will learn that what you see is only half the story. The shaft of the penis goes equally deep into his body, where the right pressure gives long-lasting pleasure without hurrying
Follow the ridge of the urethra down along the front of the penis, to where it goes under the scrotum. Massage it from side to side as you move down, and feel how his erection really extends several inches below the base of the penis, disappearing into his body below the base of the scrotum. Spend a ew minutes massaging his penis in small circles through the scrotum - once he is fully aroused, this is a nice place to spend some time. You will
eventually get to a point about an inch below the bottom of the scrotum where you will feel his penis shaft go ‘underground’. Remember this point: it’s an excellent place to apply pressure during orgasm. At this point you have left the soft tissues of the penis and are feeling muscle. You can press a lot harder here; a firm push is rewarded by a greater firming of his
erection and a rush of pleasure along the whole penis.
If you have a finger still on his glands (or even if you don’t), you should see a drop of fluid every so often. This is his lubrication, or ‘pre-come’, and - I don’t have to tell you this, do I? - should be gently massaged into his glands. (Note for the girls: though this isn’t semen, it can potentially contain sperm, so use whatever precautions are appropriate for full (intercourse.)
You have a hand on his scrotum, or ‘balls’ - another very interesting place!
The skin of the scrotum is also unique, and quite different from that of the penis. It has ridges, odor glands, hair, and is exquisitely sensitive, loving to be stroked and tickled. Hiding inside the scrotum (which by now is probably firmed up like a little baseball) are the two testicles. At this point it is probably wise to ask if he likes to have his balls touched or
massaged. Although they have a well-earned reputation as the seat of pain in the male body, it actually takes quite a bit of pressure to hurt the testicles - they are really much more sensitive to impact than to pressure.
He may find it exciting to have you massage them, or he may hate it. (Note to those in long-term relationships, testicle cancer is one of the most common cancers in boys and it is very treatable - so check for lumps several times a day!).
If he has never tried it, I strongly recommend removing the hair from the scrotum, either by shaving, or plucking. As Dr. Evil (Mike Meyers) said in Austin Powers, ‘a shorn scrotum is a thing of beauty.’ Removing all the hair makes the scrotum fantastically soft and much better for petting. Plucking is by far the best, taking about half an hour. If you shave, use a sharp
double-edged blade and do it dry, with baby powder or cornstarch for a lubricant. Trim but don’t shave the hair at the base of the penis or the top of the scrotum, as that is the ‘load-bearing’ area during intercourse, and any prickles will be a serious problem.
The scrotum is also very temperature-sensitive, acting like a little weather station. So are the tissues behind it. Cold, in particular, has a dramatic effect, and if he is up for it, you should try pressing ice into the base of the scrotum - the sensation is incredible, especially during orgasm.
Where were we? You have a firm finger below his scrotum, where you can feel his penis pump up when he contracts his muscles (there’s some Latin name I don’t remember [pubococcygeus - Ed.]; these are the muscles you strengthen with ‘Kegel’ exercises, and most people would likely call them the ‘love muscles’). If he is close to coming, even this pumping may stretch the front of the penis enough to trigger an orgasm.
Move your fingers down his perineum (the slight ridge between scrotum and anus). This is a wonderful area to massage. In another inch you reach the anus, the other focus of erotic pleasure in his body. The skin around anus is as sensitive as the lips, a place for soft tickling, but able to grip as firmly as a fist, a place for fucking. Bill Cosby may get mileage out of
fear of anal penetration, but I think 99% of all males love the feel of a finger in the ass.
Use some of his or your own lubrication to massage his anus. If you wish to, press firmly and feel it open ever so slightly to allow you to massage the entire firm sphincter (opening). Slowly or by surprise you can slip a finger in. There are no more nerve endings past the anus, but the feeling of stretching and penetration is heady and delightful all in itself. At this
point you may decide to head farther up to massage his prostate. This is (as everyone says) a ‘walnut-sized gland’ about one finger’s length in. It is the true root of the penis, which you have now followed from the delicate glands, along the soft shaft, down to the muscled base, and deep into his body. Massaging the prostate enough will usually (not always) trigger
orgasm, a different experience from a purely penis-based orgasm. If you do this, you will feel the enormous firming and contractions that precede and accompany ejaculation. It’s time to put him out of his misery. With one hand pressing against the scrotum or pushing into his anus, and another massaging the glands and final inch of the penis (or with your mouth doing
the same), ‘go for it!’. There’s more you should know about how a boy works. Erection, orgasm, and ejaculation are all separate mechanisms. They do not have to accompany each other; the only rule is that orgasm does cause ejaculation (unless something is medically wrong). In particular, erections can come and go for no apparent reason, so don’t worry if you feel him go soft once in a while. We have been talking a lot about the ‘primary
erogenous zones’, which I hope you now know well. There are of course other parts of his body that he wants you to pay attention to, such as his nipples (as sensitive as a woman’s, and too often neglected). But there is one erogenous zone more important than all others, and one you can spend a lifetime exploring together: his mind. We males love to be touched and petted and stroked and sucked, but more exciting than all of that is the thrill of giving pleasure to and sharing pleasure with another person.
OK, that is all I have. Now go and put my helpful advise to work. And have fun
One of the secrets of successful mutual masturbation is varying your hand motions. Here are just a few techniques that are indispensable.
Use both hands, alternating back and forth in a pattern you develop to offer him the most arousal. He will notice the difference. Your less practiced hand is more tentative, less firm. He’ll respond to that. But only temporarily. Don’t get into a routine where the strokes are dull and noncommittal; men like to be handled firmly.
Bring both well lubricated hands down on his shaft. Some penises are so big they require two hands. If your partner’s doesn’t, then use the other hand to caress and lightly flutter his testicles, or tighten around the base of his shaft. If both hands fit along the length of the shaft, move them together, up and down, in the typical pumping motion. You can also vary the directions of your hands, one up, one down at the same time.
The Anvil Stroke
Bring one hand down, letting it stroke the penis from the top all the way to the bottom. When it hits the bottom release it. Meanwhile you’re bringing your corresponding hand down on the top of the shaft, creating an alternating beating motion, hence the name anvil stroke.
The Shuttle Cock
Take the penis in both hands, fingers lightly touching the sides of the shaft. In order to visualize the position, think of yourself holding a clarinet. Now flick the penis back and forth between your two hands by holding on to the loose skin of the shaft. Shuttling it back and forth in this manner may not seem incredibly thrilling to him at first, but pretty soon as it builds up momentum, it will drive him out of his mind.
Place both of your hands side by side against his shaft like a pair of bookends. Now push hard against his penis. Then lift your hands up and down. Continue in this manner for a while. The constant tugging on the skin around the balls and the mons pubis will do the trick.
The Base Clutch
Tighten your thumb and forefinger around the base of the shaft, pressing down on the testicles. This will help you steady the shaft in your hand. If the skin on it is slick and smooth, you can stroke the penis with more friction, thereby augmenting the thrilling experience.
The Love Tug
As you are stroking him, lightly pull on the wispy strands of pubic hair sprouting from his testicles. Don’t pull so hard that you remove them altogether - just tease them gently and lovingly.
Tickle his testicles with one hand while the other moves up and down.
The Thigh Swatter
Use the hand that is currently unemployed to firmly but lovingly pat his inner thighs.
Best Fist Forward
Place your fist against his perineum as you’re stroking him. He’ll probably start opening his legs a little wider, giving you more space to press against.
I call a man’s nipples “chestnuts” because they are a primary erogenous zone that happens to be located on his chest. Massage one of his nipples while you masturbate him. Spin the little pink and brown areole between your thumb and forefinger as if you were trying to find a good station on the radio.