I recently spoke at Curious Minds Weekend in Toronto at the Hot Docs Ted Rogers Cinema. Audience members submitted questions on cards before the show—anonymously—but the moderator, Lisan Jutras of the Globe and Mail, and I were having so much fun talking with each other that we didn’t get to many cards. So I’m going to quickly answer as many of the questions from the audience at Curious Minds as I can this week.
Q: My husband and I have been seeking a third for a threesome. After a very palpable night of flirtation, I asked a mutual friend (as we shared a cab) if he would be down for a threesome. He said yes, but I was not about to spring him on my husband that night. So I texted him later about it, and he has ignored me. What should I take from this?
A: The hint.
Q: A friend’s BF won’t go down on her no matter how much she asks. She still won’t break up with him, even though she told me that oral is the only way she has ever had an orgasm. How do I get her to realize her sexual pleasure is a priority?
A: If your friend’s BF doesn’t know oral is the only way she can orgasm, she should tell him. If she told him and he doesn’t care, she should dump him. If she told him and he doesn’t care and she won’t dump him, you’re not obligated to listen to her complain about the orgasms she’s not having.
Q: I’m a bisexual 42-year-old female with an extremely high sex drive who squirts with every orgasm. How do I deal with friends — even people at a sex club — who think you’re a freak because “women aren’t supposed to be horny all the time.”
A: If your friends — presumably people you aren’t fucking — complain that you’re horny all the time, maybe it’s because you don’t talk about anything other than the sex you just had or the sex you hope to have soon. If people at sex clubs (!) are complaining about how horny you are… either you’ve accidentally wandered into a yacht club or even people at a sex club wanna talk about something other than sex every once in a while.
Q: My very Christian friend is about to get married. Though she is socially very liberal, she is pretty sexually repressed. I want to do something to encourage her to explore her sexuality a bit before she takes a try at partnered sex. How weird would it be to buy her a vibrator as a shower present?
A: Don’t give your friend a vibrator at her shower — gifts are opened in front of guests at showers — but go ahead and send her one. Tell her it’s a pre-bachelorette-party gift.
Q: Two guys divorced in order to bring a third man into their relationship on equal terms, and they now plan to start a family with their sisters acting as surrogates. Thoughts?
A: Mazel tov?
Q: I am 31. My husband (newly married) is 46, almost 47. He takes forever to come, no matter what I do. How do we speed up this process? My jaw, fingers, etc., are all very sore.
A: Your husband speeds up the process by incorporating self-stimulation breaks into the blowjobs, handjobs, etcetera-jobs you’re giving him. He strokes himself while you take a quick breather and/or an Advil, he gets himself closer, you get back to work.
Q: I’m 47 and my wife is 31. I take a lot longer to come and recover than she would like. Could you please explain to her that it’s normal for a man my age to “slow down” and it’s not her?
A: Happy birthday. And, yes, it’s normal for a man to slow down as he ages — it’s not her — and there are younger men who take a long time to come. But such men need to take their partners’ physical limitations into consideration. To avoid wearing out their partners’ jaws, fingers, etc., they need to take matters into their own hands. They should enjoy that blowjob, handjob, twatjob or assjob, take breaks to stroke their own dicks, eventually bring themselves to the point of orgasmic inevitability, and end by plunging back into that mouth, fist, twat or ass to blow their load.
Q: I have been reading your column since the early 1990s. Since that time, what has struck you in the kind of problems people write you about?
A: People don’t ask me about butt plugs anymore. I used to get a letter once or twice a week from someone who needed to have butt plugs explained to them. But butt plugs have their own Wiki page now, so no one needs me to explain them anymore. But for old times’ sake: They look like lava lamps, they go in your butt, they feel awesome, and they typically don’t induce gay panic in butt-play-curious straight boys.
Q: Would you share your thoughts on our prime minister, Justin Trudeau?
A: I think Justin needs to stop fucking around and legalize weed already, like he promised.
Q: When are you going to move to Canada already?
A: See above.
Q: Polyamory after marriage — is it okay?
A: For some.
Q: I’m a submissive gay boy. I saw you walk into the theater tonight wearing combat boots. Is there any way I could lick your boots clean after the show?
A: Sadly, I didn’t see your question until after I got back to my hotel.
Q: Straight male here. My best, male friend of 20 years transitioned to female. I’ve been super supportive since day one, but her transitioning is all she ever talks about, and it’s getting tiresome. I miss our discussions of bicycle repair and Swedish pop music. How can I tell her to give it a rest while remaining supportive?
A: If she began transitioning last week, then of course it’s all she can talk about. If she transitioned five years ago and it’s still all she ever talks about, then you’ll need to (gently) be the change you want to see in the conversation. Listen supportively when she discusses trans issues and seize opportunities (when they arise) to change the subject (“So how do you think Sweden will do in Eurovision this year?”). •