Dear Ty

Dear Di,
I cannot orgasm. I just can’t. My boyfriend thrusting inside of me feels good, but I always go to sleep really unsatisfied. I’ve tried rubbing my clit while we bang but it doesn’t help, which makes me think masturbation won’t work either. This is really frustrating and I’m worried I won’t ever be able to have an orgasm.

—Can’t Orgasm, Might Explode

Dear COME,

I am a true believer that orgasms are the best gifts we can give ourselves, and it’s about time you started unwrapping some presents.

How often do you masturbate? I know you’re discouraged, but please tell me you’re still touching your taco on the regular. Although I don’t have any statistical data to back this up, I’m willing to bet the vast majority of people reach climax for the first time during a self-love session. If you’ve hopped off the twat-tickling train completely, you aren’t going to reach your final destination anytime soon.

I also suggest you walk—no, run—to a sex shop and buy yourself a vibrator. I have fond memories of the first time I introduced my beaver to a buzz toy—it felt good to retire my fingers and put an end to marathon masturbation sessions. Many women find they are able to get their rocks off not only easily but much more quickly with the help of a battery-operated boyfriend. Buy one, now!

You mention that you enjoy your boyfriend’s thrusts inside of you—but do you ever enjoy the feeling of his tongue? If your man’s face and your vagina aren’t already acquainted, it’s high time you introduce the two. One of the most common ways women hit the big O is through oral sex. Make your man comfortable, spread your legs, and let him go to work.

If your man’s trip downtown doesn’t do it for you, try having sex in the spooning position. Spoon-style sex leaves two pairs of hands free to explore, stroke, and rub your pussy. You should also try climbing aboard your boyfriend and riding him like a wave. Being on top not only affords you the opportunity to control the depth of penetration, but also gives you the chance to grind your pelvis against your guy.

I also recommend you use your newly purchased vibrator while having sex. I know some men are intimidated by a buzz toy, but your boyfriend might just have to swallow his pride in this situation. Although I can’t say for certain, I have a feeling a little oral sex, followed by some old fashioned penetration and good vibrations, will be the key to a beautiful orgasm.

If all else fails, there’s nothing wrong with making an appointment to see a gynecologist. He or she will be able to give you more information, tips, and tricks to help you reach climax.

Love,
Di

Dear Di,
I’ve always fantasized about having sex in Café Nostalgica. The employees at that restaurant are so good looking that I feel aroused whenever I’m there. How do I do this and not get caught? Do you think I should invite one of the servers to join me?

—Naughty in Nostalgica

Dear NN,

While I won’t deny the employees of Café Nostalgica are unusually attractive, I don’t think having sex in the restaurant is the wisest thing to do. Sure, there’s the mysterious staircase leading to what I think is a relatively deserted basement, but otherwise, the café itself is pretty small and always packed. Getting busy in such a public place will likely lead to your arrest, which I bet would put quite the damper on the experience—don’t you think?

Instead of risking a run-in with campus security or the fine ladies and gentlemen of the Ottawa Police Department, why not stage a restaurant rendez-vous in your own home? Invite your significant other or favourite fuck friend over for a night of wining, dining, and 69-ing. He or she can play server while you are the patron of the establishment. I’m thinking white tablecloths, candles, the whole nine yards. Just remember to blow out the flames before you have your way with your waiter atop the table.

I know I usually encourage my readers to push their boundaries and explore their fantasies, but I think you might have to hang up your hat and settle for second best. Unless, of course, you do manage to score yourself a sexy Nostalgica server—in which case, he or she just might be able to help make your restaurant romance a reality.

Love,
Di

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