photo by Brandon Baunach

Dear Em & Lo,

I’ve been dating my boyfriend for five months and we have a great relationship…well, almost great. When we have sex, I have a hard time crossing the finish line. We’ve tried many positions and everything feels great. I just can’t orgasm. It’s at the point that it’s getting really frustrating for me, and any help would be greatly appreciated!

– Desperate for a Victory Lap

Dear DFAVL,

If you want to know how you and your boyfriend can orgasm simultaneously during penetration every time, sorry, you’re out of luck. If we knew that, we’d be richer than Oprah. But here are ten things we do know that will help increase your chances of orgasmic success…

1. We’re assuming by “sex,” you mean penile penetration. And that’s your first mistake. You say you’ve tried many intercourse positions, but maybe it’s not an intercourse position that will ultimately do it for you — maybe it’s oral sex, or handwork, or some combination of the two. There’s no shame in getting your orgasm via non-intercourse means — the majority of women don’t. Nor is there any shame in you having your orgasm and then him having his. Remember, sex — especially for women — doesn’t necessarily happen in a straight line, i.e.  your orgasm won’t necessarily be located conveniently at his finish line, or vice versa. Plus, it’s much easier for gals to keep going after a Big O than the lads. And you may find that certain intercourse positions feel even better (perhaps even orgasmic) after you’ve had one orgasm.

2. Again, intercourse alone is orgasmic for very few women, given how far the clitoris is from the vaginal opening — and how key clitoral stimulation is for most women’s orgasms. So don’t forget to supplement all those positions with a little extra clitoral stimulation — your hand, his hand, a small vibrator, a helpful neighbor’s hand…

3. Three words: Coital Alignment Technique. Learn it, live it, love it, Google it. In fact, any position where your bodies are mashed up against each other is good — because close contact means more friction down there, and more friction down there means more clitoral stimulation.

4. Try a vibrating love ring, like this one from GoodVibes. Because vibrating clitoral stimulation could be just the thing your intercourse life has been missing. You know all those times a dude looks at a sex toy and thinks, “Hey, my penis doesn’t vibrate like that?” Well, now it can!

5. We’re assuming that you can orgasm on your own, in which case, have you tried playing a little show-and-tell and teaching your boyfriend how to mimic that?

6. If you can’t orgasm on your own, then scratch everything else we’ve said and start masturbating! Often! Treat yourself to a vibrator, dim the lights, think some sexy thoughts and let the love flow. Because in our ten years of dishing sex advice, most women we’ve spoken to find it easier to learn solo first.

7. Sex toys are your friend. If your boyfriend is the jealous type, remind him that sex toys don’t cuddle and they’re useless at pillow talk. In addition to vibrating love rings, there are tons of other great toys for couples, like finger toys (which can really turn hand work up to eleven) and small pebble-like vibrators, which can nestle comfortably between your bodies.

8. Have you lubed today? Remember, man-made lube is not a crutch and using it doesn’t mean you’re not that into the sex. In fact, lube is one of the greatest bedside accessories we know. Using lube means that your sensitive parts are less likely to get over-sensitive while you’re trying out various different hand, tongue, toy, and intercourse techniques. And you’ll avoid rug burn!

9. Try not to over-think your orgasm. It sounds impossible, we know, but the more you stress about your happy ending, the less likely it is to happen. Sure, keep experimenting, and try out everything we’ve suggested here — but try not to think about this as a mission to O. Rather, it’s a mission to improve your sex life. Because orgasms are kind of like bad boys — the more you ignore them, the more likely they are to show up.

10. Finally, be patient. Five months may feel like forever to you, but in the grand orgasmic scheme you’re really only just getting going. Just because your orgasm hasn’t made an appearance yet in this relationship, doesn’t mean it won’t. Orgasms are mysterious things and sometimes things just click into place one day. Hey, long-term monogamy has got to have its benefits, otherwise we’d never enjoy the pleasure of board games.

We hate to sound like a self-help book (what color is your parachute, anyway?) but when it comes to sex, the journey is meant to be at least half the fun. Of course every woman has the right to an orgasm with her boyfriend, and we understand your frustration, and you should definitely be demanding, but don’t forget to appreciate this great relationship and enjoy the nice-feeling sex you do have, because having a good time together is the best foundation for having an orgasmic time together.

Gooooooooooo sex!

Em & Lo