Many experts believe masturbation is necessary to maintain your sexual health. I have tried all the steps a few times, and the closest thing to orgasm I can get is a weird tingling in my penis. Since you have known how to masturbate if you're a boy, you can always experiment with different techniques to make you feel great. You can consider buying stuff like vibrating rings, blow-up dolls and toys that look like vagina, anus or mouth. Masturbation Instruction for a Boy.