Advertisement

Lifestyle

Yee, ha! Ouch!

Dear Sasha,

I want to have sex with me on top, but my vagina always seems to tense up or close. My boyfriend and I have no problem in the missionary position – I just want to try on 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 me any tips.

Anxious Cowgirl

Dear Anxious,

You might begin by straddling your boyfriend and having him finger you so you 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 you might also want to hold a small vibrator to any area that gives you particular plea-sure, to help you loosen up, so to speak.

You could 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 doing yoga? (You know, when they tell you to hold your moola bandha?)

While tensing these muscles might give your boyfriend a thrill once he’s inside you, and will certainly help you later in life when sneezing makes you pee your pants, it doesn’t facilitate penetration itself.

Another thing you could 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 your ass and roll you up into a couples seated upright, then cowgirl. Of course, you should be as possible doing this, and if it hurts when you’re straddling him, don’t feel 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 tex-ture, 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 becomes slick with heat. Again, pleasant flavour and a nice, tart odour.

Toys. Something 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.

Personals Safety

Dear Sasha,

How safe is it to respond 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 disap-pointing and frustrating. I don’t want to feel so negative about that, because it will start to affect my rela-tion-ship 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 explore individual ads/places with body rub licences for some relief. I am very discreet and would not want to pursue anything illegal. Tried things like Ashley Madison, but it’s not really for me. Any advice or reassurance or other avenues I might explore would be appreciated.

Frank

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 of Toronto provides those licences and makes thousands of dollars every year off them, yet those who must purchase them in order to work toil in a 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 practise 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 any more and ask for their advice on what to do, here’s the list: the Christian Legal Fellowship, Real Women of Canada, the Catholic Civil Rights League.

So, yes, even though nobody will actually see you getting the hand job 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 eja-culate 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, as intended, it implies 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 say this is rare) or if you’re entrapped trying to purchase sex on the street, you will be trotted in front of the courts, fined about as much money as 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 you’re 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 practise erotic labour. And if you want to get laid in the meantime, here’s a list of legal ways to do it.

Advertisement

Exclusive content and events straight to your inbox

Subscribe to our Newsletter

This field is for validation purposes and should be left unchanged.

By signing up, I agree to receive emails from Now Toronto and to the Privacy Policy and Terms & Conditions.