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The more your brain travels a certain path neurologically, the more effortless it becomes. The more signposts of impending orgasm your brain can recognize, the easily it will trigger the orgasmic response. Most of us have a "pre-sleep" ritual: We'll brush our teeth, wash our faces, go to the bathroom—and all these actions work as signals to the brain that it should get ready to sleep. Pay attention to what your orgasm triggers are. For example, if he's giving you oral and normally inserts his fingers just before you climax, that's one signal your brain knows to read as a pre-orgasm sign.
How to Orgasm Together
I want to get one thing straight here: Simultaneous orgasm isn't common; it's actually very rare. The reason for that is because women and men generally don't orgasm through the same (penetrative) means. She'll often have her orgasm through oral sex, while he'll then have his orgasm during intercourse. Timing is also a factor, so simultaneous orgasm is usually about getting him to orgasm more slowly and getting her to orgasm more quickly. I've focused on how to orgasm together through penetration here, but don't ignore other ways (like masturbating together or having head-to-toe oral sex).
- Get him to orgasm first and make the "together" orgasm the second one. Most men find they have much better control second time around.
- The better he knows his orgasm pattern, the more able he is to control when he climaxes. The easiest way to do this is to get him into the habit of "scoring" his status. (10 is an orgasm and 0 is not aroused all.) If he calls out a six, he can afford to keep thrusting hard for a bit longer. If he says he's an eight, you need to slow down, stop or change stimulation. Lots of men find it easier to practice assessing their arousal levels during masturbation so they can focus exclusively on the task. He's doing well if arousal hovers around seven or eight for an average session. That means he's getting a lot of enjoyment but he's able to keep his pleasure relatively in control.
- Get him to use a vibrator on you. One of you holding a wand vibrator (slim, cylindrical, non-intrusive) over the clitoral area during penetrative sex is, in my opinion, the most effective way to ensure a shared orgasm experience. Why don't more people do it? Some don't like introducing something 'mechanical', and lots of men don't understand the whole vibrator thing and feel a tad threatened.