Dear Sasha,

I’m a male in his 40s who’s told he’s a good lover by his partners. I know I am, but there is one thing that I sorely lack in the female pleasuring department: I can’t seem to make women squirt. I’ve tried numerous times, and the only thing I do is give them a burning and peeing sensation and myself a numb arm and wrist. I would like you to point me in the direction of books or videos that teach exactly how to do this properly. I sure don’t want to learn it from a porn flick that doesn’t show much anyway.

I Squirt You Not

Here’s my first piece of advice, Squirt: stop labouring under the impression that you can “make” a woman do anything — and let’s put a special sticky note with this caveat on the G-spot. Imagine how it feels for us womenfolk that this hallowed piece of real estate was named after a man (Ernst Gräfenberg). Then, to add injury to insult, we’ve got one intrepid explorer after another poking and prodding around down there so they can add dowsing to their curriculum vulva.

I think because the G-spot has the potential for such spectacular results, people have placed a real premium on claiming it, almost as though they’re drilling for oil. This kind of capitalist approach can really put a lot of stress on both the prospect and the prospector.

This is not to say that becoming skilled in the art of pleasure isn’t a noble pursuit. But your proficiency must be accompanied by a desire to learn from your partners. Women do not conform to certain industry standards when it comes to bodily functioning. You must integrate listening and asking into your list of skills.

Perhaps the women you’ve been with haven’t ejaculated because they can’t. (Some advocates — yes, there are female ejaculation advocates — say that all women can. Women who are tired of hearing this — and tired of being relentlessly jabbed in the bladder — are free to use my response, which is simply to piss on fixated partners.) Or they are unfamiliar with the particulars themselves.

The burning or peeing sensation is not unusual, since you are massaging the paraurethral (“para” meaning alongside, “urethral” meaning related to the urethra) glands. Debate still rages about where this fluid comes from, even though the bladder is the only organ in the direct vicinity large enough to produce so much.

I’m going to give you some resources, Squirt, but remember, they provide a general understanding; discussion is paramount.

Films: Nina Hartley’s Guide to G Spot Sex, and Female Ejaculation For Couples by Deborah Sundahl.

Books: Female Ejaculation & The G-Spot ($22.95, Hunter House) by Deborah Sundahl.

And a warning: female ejaculation enthusiasts generally come in two types: goddess fluid activist ( or Frank T.J. Mackey, Tom Cruise’s character in Magnolia (, each with his own agenda. So take all of this information with a grain of salt and please remember to have fun.

Now we’re both cross

Dear Sasha,

I’ll admit, after giving this some thought, that I never should have asked you the question “Is it wrong to hide my other life from my girlfriend?” Still, your response angered me, because you act as if open communication is a solution without enormous risks for someone in my position. Don’t belittle me with this Clinton, loophole and “shop-worn” business; try and walk in my shoes and tell me that you wouldn’t do the same.

Let’s say I tell my girlfriend about this double life and she says she’s fine with it, but one day our relationship needs to break up and she becomes bitter. If things get ugly, she has access to my entire circle of friends and associates. What if she exposes me? I would be destroyed!

My play friend is a friend at a distance; she knows me only at my store, doesn’t know where I live and has no access to my network. All of our play takes place in my environment, so I can prevent any potential recording or other possible activities that could put me in a compromised situation. If she wanted to expose me, all she could do is picket outside my store, in which case she would just look crazy.

If you really understand the queer and kink communities as you claim, you should understand that I really have little choice but to hide certain aspects of my life if I want to keep the lifestyle I have. If I get exposed, I could very well end up marginalized like every other tranny whose male-bodied/female-identified choices of employment forcibly narrow to fashion, performance and hooking. Name me one out-of-the-closet cross-dresser who has made it as a successful businessman (not in the fields of fashion, performance or sex work) and I will give you half my business.


I don’t want half your business Lewis. I just want people who own shit to stop making excuses for their deceitful behaviour based on ideologies of shame and marginalization they themselves help perpetuate.

I would also like these people to stop acting as if I and every other hooker, fashion designer and actor get to live our lives openly 24/7 and that when we do it isn’t a struggle.

Do you know what a misogynistic and competitive world stand-up comedy is? Do you think for a fucking second that Eddie Izzard had an easy time coming out as a cross-dresser in that environment? Do you think shit’s been easy for Nina Arsenault? These people live their lives openly despite attitudes like yours, you self-important schmuck, not because it’s easy or more acceptable in the environments in which they move. And if it’s become easier and acceptable it’s because they’ve fought tooth and nail to make it so.

Keep your secret, Lewis. Don’t ever truly let someone in. Don’t trust anyone. Put your business and reputation before intimate connections and truth. Let us live our marginalized lives while you hold onto some idea that we’re disreputable for doing so. This is the life you’ve chosen for yourself, so now you have to play by those rules.

Like I said earlier, you have only yourself to blame for fostering an atmosphere of shame around such proclivities, choices and realities.

Ask Sasha: [email protected]

Sasha Van Bon Bon

Sasha is a nationally syndicated sex columnist whose work has appeared in a variety of Canadian weeklies and online magazines for over 15 years. Her column appears weekly in NOW magazine. She is also...