Sasha: Friends with benefits

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Dear Sasha,

I have a very close friend whom I love dearly. (Though I'm not going into that mess. My loving her is not the issue.) I've known for years that this fantastic woman has a hard time reaching orgasm. In the last year we have had two sexual encounters, during the last of which I discovered that not reaching orgasm can be just as painful for women as it is for men. To me this will not do.

So early this week I started looking into reasons why some women have difficulty reaching climax. (I've been discussing it with her as well.)

I was hoping you might be able to give me a list of books or videos or published articles about women with difficulty having an orgasm, specifically related to hypersensitivity in the clitoris or which identify mental roadblocks (things that may be mentally holding her back from climax). Please, I really want to help this woman who has found very little sexual satisfaction in life.

Friend and Lover

Ah, but your loving her is the issue, so before we get to the resources, let's reflect candidly on your intentions and expectations.

Do you remember The Simpsons episode called Lisa's Date With Density? In it, Lisa says to a besotted Milhouse, "I like you, too, Milhouse, but not in that way. You're like a big sister."

Milhouse says, "No, I'm not! Why does everybody keep saying that?"

Then Lisa says, "Would you do me a favour? When you get back to class, just give him [Nelson] this note." Then Milhouse groans and Lisa says, "Please?"

Milhouse thinks to himself, "When she sees you'll do anything she says, she's bound to respect you," and then he blurts out, "Sure! What's a big sister for?"

Are you taking on a sexual stewardship role hoping it will set in motion a more intimate relationship? (Cue Yoda voice.) If so, beware, Teacher Sister. Many have gone this route and found their Student Lover leaving them high and dry once carnal enlightenment has been attained. Being the one to unlock the secret of her flower does not guarantee that you alone will be privy to its aroma.

A woman may suffer from vulvar sensitivity for a variety of reasons, many of them also very sensitive. As you attempt to squire your friend along on her erotic awakening, keep in mind that men staking claim over women's bodies and the way they think they "should" function can also come across as meddlesome and egotistical.

Off the top of my head I can name three pieces of my business end named after men (Skene's glands, Bartholin's glands and the Grafenberg spot) and frankly, I think that's quite enough. Give her space to make her own judgments and discoveries.

Taking all that into account, Friend, here are some resources that contain supportive information about female sexual dysfunction: online groups that deal with vulvar pain and sensitivity (,, books with info on the vagina and its various attributes (The Clitoral Truth by Rebecca Chalker (Seven Stories); Woman: An Intimate Geography by Natalie Angier (Anchor) and educational films.

The Come Right Inn

Dear Sasha,

My lover and I are looking for a decent, clean place (hotel, whatever) to have sex during our lunch break. We're both working downtown and we don't have cars, so we can't drive away to our homes or do some backseat. I looked on the internet but couldn't find anything about renting a room by the hour. Do you know a place where we could go?


"By the hour" and "decent and clean" are generally considered mutually exclusive, according to friends of mine who have an interest in keeping track of such things. According to Kaya, "Typically in downtown Toronto you will be hard-pressed to actually find hourly rates. Really, this is limited to the Kingston Road strip in Scarborough, and it is my understanding that hourly rates are illegal."

Hotels obviously clue into the fact that people require their services at all times for a range of reasons, but to openly acknowledge that one of those reasons is illicit sex would be unseemly and, apparently, against the law. To profit off those who require rooms for daytime use while simultaneously keeping up appearances, they offer what is known as a day rate, and that is what my friend Veronica suggests you look into. "They are generally less expensive then renting a room for a night," she says.

The Grand Hotel has a day rate of $99, and that's about average. Usually check-in is around 9 am and checkout around 5 pm.

"And now that there is checkout on the TV as well as over the phone," says Veronica, "they can feel more discreet about leaving after an hour and not having to go back to the front desk to announce they are finished. They just have to get in touch with reservation request by email and someone will get back to them and book for them. The Grand also does cash instead of credit card if they need discretion and no paper trail. The Grand just holds card info for incidentals."

You may try posting on Craigslist to see if there are any escorts who have apartments they use strictly for business who would be willing to rent their space to you as well. This would require a strict screening process, but it's worth looking into.

It might also be worth looking into a car-sharing program like Zipcar or Autoshare, keeping in mind, as the article I've linked says, "Very steep fines are imposed for bad behaviour, whether you've left the car filthy or neglected to get it back on time."

If you are interested in something more immediate and less costly, I suggest the Loft 18+ at 375 Yonge. It has a maze of private booths where you can watch pornography and enjoy one another's adult company on the faux leather sofas. As peepshow booths go, the Loft is the cleanest I've been to, though I suggest you bring a blanket to cover the sofa and don't look too hard at the walls. (No, that's not a stucco finish.)

This column was originally published in NOW Magazine. Ask Sasha: [email protected]

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