Many males discover masturbation by accident, when one day they're rubbing their penis and it feels so good they don't stop until they have an orgasm. But there are finer points to masturbation, and there are many ways to make it more enjoyable.
There will be times when you feel a strong need to masturbate when it isn't convenient. In this case you may want to ejaculate as quickly as possible, perhaps in the bathroom. That's fine – but you should know masturbation, like two-person sex, is much more pleasurable when you can relax and take your time. If you have your own bedroom and can close the door, you can have a great masturbation session every night and perhaps every morning, too. If you share your room, you can masturbate privately in the bathroom or shower. Or, you can wait for your brother to fall asleep and masturbate quietly under your covers. But if he hears you, be prepared to answer some questions!
Some guys masturbate by lying on their stomach and rubbing their penis against their bed. A more common technique involves lying on your back and rubbing your penis with a hand (or hands). In this position, when you ejaculate, the semen will end up onto your chest or stomach, so it will be easy to clean up. (You'll probably want to pull up or take off your pajama top or T-shirt, so as not to wet it with semen, and you'll want to have a roll of toilet paper or a box of Kleenex handy.)
Have a question about positions or techniques? Go here.
Just about every successful masturbation session begins with getting an erection (ee-RECK-shun), commonly called a "hard-on," "boner," or "woody." An erection occurs when your penis fills with blood to the point that it becomes quite a bit larger and firm to the touch, usually sticking straight out from your body or angled upward as you stand. (If you're lying on your back, your erect penis might rest against your abdomen.) Getting an erection is usually as easy as thinking sexy thoughts and rubbing your penis. If you're going through puberty, or if you haven't ejaculated in a while, you may not have to do anything to get an erection – they can happen spontaneously, or without provocation. This is normal and just one of those puberty things everyone has to deal with.
Once your penis has reached its full length and hardness, take a hold of it and rub it lengthwise at a consistent rate. This will mimic what it feels like to move your penis in and out of a woman's vagina, which is what happens during sexual intercourse.
Here are four basic "grips" you can try. They're really just starting points; it's important for you to try little variations on them, as this will allow you to choose techniques that feel best to you.
In this common technique, you simply wrap your fingers around the shaft of your penis like a baseball bat and rub it up and down. It provides lots of contact between your hand and penis – and more contact means more pleasure.
In this technique, your hand and arm form an angle with your penis, with four fingers on top of the shaft at a diagonal and your thumb below.
This one is good if you have a smaller penis. Simply hold the penis as you would a pen or a pencil. This grip allows maximum control and maximum distance of motion
This one – kind of a backwards version of the "fist" – is a little funny, but it feels very good. This time, grab your penis from the left side rather than the right (if you're right-handed).