When the good Lord (or the universe, or the flying spaghetti monster) created humans, men and women got something of a trade-off in terms of genitalia. Men got the ability to pee whilst standing up, and women received the far-more-pleasurable boon of multiple orgasms. Sucks to suck, fellas.
But all is not lost my male brethren. While women are known as the only sex able to achieve multiple orgasms, apparently we're both able to enjoy such a sexual feat. According to certain prominent sex educators, while men and women are physiologically different, we're actually neurologically similar, and can both attain the bliss that is a multiple orgasm.
The first thing to get past, however is that contrary to what many men believe, ejaculation and orgasm are not one and the same. Generally, the two events occur within a second of each other, so it may seem like they're inexorably intertwined, but that isn't the case.
Sex therapists William Hartman and Marilyn Fithia posit that the techniques used to achieve a male multiple orgasm are thousands of years old, and making it happen isn't as difficult (or kinky) as you might think.
Alternative media outlet AlterNet had two separate features on how men can achieve multiple orgasms, one with sex educator Carlyle Jansen and the other with Jack Johnston, both of which outline different techniques. To level the orgasmic playing field a bit, you'll find a basic breakdown of both methods below.
The Squeezing Technique
Otherwise known as "male kegels," this particular method first involves locating your "pelvic floor muscles." To put it in the most simple of terms, these are the muscles your penis uses, and just like any muscle, strengthening and learning to control them will lead to better sexual results, aka multiple orgasms.
A guy's first step is to actually learn where the pelvic floor muscles (PFMs, for the sake of brevity) are located. An easy way for a dude to test the waters is to stop peeing mid-stream. The muscles used to stop your stream are the same ones you should be strengthening, but don't abuse this system, because that's not very healthy for your bladder.
Once you have a good handle on your PFMs, and can contract them at will, Carlyle Jensen recommends doing some exercises. You can just clench these muscles for ten seconds at a time, do a "towel exercise" (lifting a whole towel with your wang) or go the more fun route and start strengthening your PFMs during sex, which can directly lead to stronger orgasms.
Now, to make your way to true multiple orgasm pleasure, you need to go one step further and employ "squeezing techniques." Essentially, this is the practice of squeezing the shaft of your D (specifically the urethra) with your index and thumb right before you cum.
Eventually, once your PFMs are strong enough, you'll be able to stop the ejaculation process without your hands. The basic idea is you can reach the peak of orgasmic pleasure without actually cumming, allowing you to repeat the process multiple times for even more pleasure.
But Jack Johnston recommends another, more fun route to multiple male orgasms, called...
Key Sound Multiple Orgasm (KSMO) Training
As Johnston puts it, Squeezing Techniques "aren't a whole lot of fun for anybody" since you need to keep constant tabs on yourself and exert a lot of self control not to cum, which doesn't always work out.
Instead, Johnston has created his own method, dubbed Key Sound Multiple Orgasm (KSMO) training. Achievable all by your lonesome (though a partner can get involved), the term "key sound" is in direct reference to the sound a guy can make when using the method's particular practice of self-stimulation, with the light moans actually contributing to a more pleasurable sensation.
Somewhat counterintuitive, KSMO training bypasses the penis entirely, and heads straight for the perineum, the stretch of skin between a guys balls and anus better known as the "taint."
Apparently, the perineal area/taint is your ticket to the male G-spot, and is at the core of KSMO training. The first step is to actually locate your perineal zone, and feel it out with a massage, enough to get a light wave of feel-goods in your body.
Johnston notes that the orgasm experience is more of a whole-body thing than just about your dick, and a perineal massage will help you realize that. If effective, you'll be able to create a "Multiple Orgasm Trigger," as Johnston puts it, with your perineum serving as the nexus point for pleasure towards the rest of your body.
The main idea behind a perineal massage is to excite the prostate, and Johnston recommends practicing this method for twenty minutes every other day. You also shouldn't ejaculate on practice days.
Once you get a good feel for KSMO training, Johnston notes you won't feel a standard male orgasms, rather, you'll experience an orgasm in "waves." Since you're not actually cumming, and ending the orgasm entirely, you'll instead get a continuous flow of pleasure, which many men are said to prefer over the standard orgasm, after perfecting the process, of course.
To quote one of Johnston's clients from the original article "the crazy thing was, instead of feeling like the orgasm was in me, it felt like I was in the orgasm--like it was surrounding and suffusing my whole body like a field of energy." Sounds good to me.
So whether with your special someone, or entirely by yourself, that's how to make a face like the guy below more than once in a single session.