Yee ha! Ouch

I want to have sex with me on top of my boyfriend, but my vagina always seems to tense up or shut close. We have no problem in the missionary position. I just want to try being on top for a change.

Dear Sasha,

I want to have sex with me on top of my boyfriend, but my vagina always seems to tense up or shut close. We have no problem in the missionary position. I just want to try on being top for a change. Sometimes I try placing myself or my boyfriend tries to place his dick inside me, but my walls are shut. Yes, this is my first attempt at girl on top ever. I guess what I need is Girl on Top 101. Please help. Send me a link or give any tips.

—Anxious Cowgirl

Dear Anxious,

You might begin by straddling your boyfriend and having him finger you first so that you may work your way up in this position to a larger item, like his penis. Take your time, don’t be stingy with the lubricant and perhaps you might also want to hold a small vibrator to any areas that give you particular pleasure to help you loosen up, so to speak.

You may also try penetrating yourself in the cowgirl position during masturbation to get a sense of how and why this might be painful for you. Where does it hurt? Is it a burning or cramping sensation, or both? Are you tensing up your pelvic muscles, something you may have learned from yoga? (You know, when they tell you to hold your moola bandha? While this action might give your boyfriend a thrill once he’s inside you, and though it will certainly help you later in life when sneezing makes you pee your pants, it doesn’t facilitate penetration itself.

One thing you could also try — carefully! — is to begin penetration in the missionary position, link your legs behind your boyfriend’s back and then have him hold you under the ass and roll you up into a couples seated upright, then cowgirl. Of course, you should be as careful as you can doing this. If it hurts when you’re straddling him on top, don’t feel that you need to continue.

So, lubricants: I have tried a couple of new ones lately that I like a lot. Please water-based cream lubricant has a lovely, silky texture, stays nice and moist in your nice moist area and is glycerin– and paraben-free. It also has a pleasant flavour and is toy- and condom-compatible.

Aloe Cadabra is made primarily of organic aloe vera gel. The texture is gooey to begin with, but it becomes slick with heat. Again, pleasant flavour and a nice, tart odour.

Toys: Something that you can cup against your clitoris or other areas that you find pleasurable during penetration is probably your best bet. There are a variety of options here.


Dear Sasha,

How safe is it to respond to personals and get involved with individuals in classified ads?  Have you heard of problems with contacts? I am a comfortably married man whose wife has pretty well lost all interest in sex, which is very disappointing and frustrating. I don’t want to feel so negative about that because it will start to affect my relationship in a bad way — otherwise, I am reasonably happily married. We’ve been together over 20 years and have had discussions about my needs to no avail, so I am curious to possibly explore individual ads/places with body rub licenses for some relief. I am very discreet and would not want to pursue anything illegal. Tried things like Ashley Madison more so out of curiosity, but it’s not really for me. Any advice or reassurance or other avenues I might explore would be appreciated.


Dear Frank,

As we sit and wait for the federal government to appeal the sex work laws to the Supreme Court of Canada that make what you are asking for legal — so, the simple desire to pay someone to touch your penis in a way that elicits pleasure and in a space where you have provider options and privacy — you are indeed doing something illegal. To make matters even more frustrating, the city ofTorontoprovides these licenses and makes thousands of dollars every year from them, yet those who must purchase them in order to work toil in legal limbo.

You might be interested to know that during the case that was mounted by a group of sex workers, the courts allowed Christian organizations to intervene. That’s right, Frank: religious groups were permitted to comment on your right to pay someone to touch your penis and on the rights of women and men to practice what is actually a legal profession using tried-and-true intimate labour safety measures. In case you want to contact these organizations and tell them that your wife doesn’t want to touch your penis anymore and ask for their advice on what to do, here is the list: the Christian Legal Fellowship, Real Women of Canada and the Catholic Civil Rights League.

So, yes, even though nobody will actually see you getting the handjob you want in order to still your restless libido (just like nobody sees your doctor stick his finger up your ass to make sure your prostate is in good shape), while the laws hang in the balance, you are doing something illegal. And so are the women who choose to do this work and choose to do it in venues where they work in groups for safety and ease. So, again, it’s okay for someone to stick their finger up your ass to check for cancer, but if they do it to make you ejaculate, that’s criminal. It’s the law’s business who touches your cock, balls and asshole, where they do it and why.

Of course this is outrageous. Of course it implies everything it intends to: that sex outside of very uncompromising parameters is dirty and wrong and needs to be policed. And it needs to be policed in a manner that conjures shame and fear. You can fully expect, Frank, that if you are caught in a raid on a massage parlour (I will state that this is rare) or if you are entrapped trying to purchase sex on the street, that you will be trotted in front of the courts, fined about as much money than the highest-paid hooker in Toronto makes and forced to go to John School (if you want it all to just go away, that is), where disgruntled former sex workers will tell you that you are a filthy person. Yet if you pay someone to massage every other part of your body for relaxation and pleasure, no problem. Just your penis isn’t allowed to be touched. Except if someone is doing it to check for disease.

Keep your eyes on this case, Frank, and do what you can to support your right to access pleasure and the rights of women and men to practice erotic labour. And if you want to get laid, here is a list of legal ways to do it in the meantime.

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