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Wrong way to a three-way

Dear Sasha,

I’ve been married for 16 great years. Me and my wife talk dirty and have great sex. I wanna take it one step further and have a threesome.

Some days she’s okay with the idea and other days she says no. How do I make this happen without her getting upset? She has a hard time seeing me with another woman for some reason. Looking forward to your response.

Vexmann

Dear Vexmann,

The thing you do not want to do is spring an in-the-flesh threesome on your unsuspecting wife. Something you may have noticed when you cruise escort websites and casual sex profiles is that those who are open to group sex are insistent about NOT being a birthday or anniversary surprise for an unwitting partner. This comes from experience, some of it extremely unpleasant.

An escort friend who specializes in appointments with couples says this:

“It sounds like he and his wife are not on the same page about having a threesome. It also sounds like his idea of a threesome is his being with two women, and nothing is said about his wife’s motives for a threesome or how he sees her enjoying it. Without that info, it’s hard to give advice.

“I would not be surprised if, when they are dirty-talking during sex, threesomes sound very sexy, but when not naked and consummating, it’s not a turn-on. This is so-o-o-o common. There are a bunch of things in my ‘spank bank’ that I would never actually want to do. It can be hard to accept, but just because you think it doesn’t mean you have to do it. And if you do it, it rarely goes as you imagine it will.”

A way of helping you understand why this might be challenging for your wife is to think of something you might find sexually demanding and imagine how you’d feel if your wife tried to talk you into it. Let’s use the very typical idea of anal sex. Though many men secretly fantasize about this, the reality might be very different.

“If she does decide a threesome is something she actually wants, then choosing someone to join them is tricky,” my escort friend continues. “The single female who wants in on a couple’s fun is often called a unicorn in swinger circles, because they do not exist or are rare creatures.

“Most women swing as part of a couple. From my super-swinger friends’ experiences, the few single ladies out there often bring a bunch of trouble with them. What happens when the gal gets a boyfriend? Will you let your wife return the favour and sleep with them?

“What if she wants to squeeze in on your relationship, either with you, with her or both of you? I knew one gal who wanted a threesome relationship, not just action in the sack, and it caused the couple a lot of grief to manage all the extras that came along with the nights of fun.

“From what I hear from couples – especially wives – who contact me on a professional basis, they have considered this type of complication and go with a pro to avoid it. Pros get it that they want fantasy sex.”

Dear Sasha,

I am wondering if you could help me? I am a married closet bi bottom male. My wife has no idea. I also enjoy cross-dressing. But I have not yet been with a man or a woman fully dressed. I cannot fully shave or my wife will wonder what’s happening. I know when I do dress I look pretty sexy. But I know the hair is a turn off. Any suggestions?

Ian/ Rachel

Dear Ian/Rachel,

Take up swimming or cycling and tell your wife you’re shaving for athletic reasons. This seems to be a very popular excuse on closeted tranny message boards.

Being honest with your partner about your desires is ideal, but if this is an impossible prospect there are ways to conceal body hair without shaving. The stockings worn by ice skaters or dancers smooth the legs and cover hair and blemishes.

Tops that cover chest hair are easy enough to find. You can look slutty from the waist down (sorry to assume you want to look slutty, but I’ve met very few cross-dressers whose goal wasn’t to look like a mid-range hooker). A fitted turtleneck and a mini-skirt with the stockings mentioned above are an option.

The website So You Want to Shave Your Legs But offers some good advice, all of it hoodwinking, sleight-of-hand stuff, but, hey, a compulsion (and I use the term knowing that it’s contentious but with the understanding that a deep secret like this it can feel this way) isn’t easy to live with, and sometimes you’ve just got to get what you want by being sneaky.

If you’re looking for places to go as Rachel, have a look at Goodhandy’s on Church Street or Take a Walk on the Wildside, Paddy Aldridge’s space for closeted cross-dressing men. She provides a safe play space for you to get pretty.

Dear Sasha,

Your column appeared on one of our monitors (the question about latex smell), and I wondered if you had heard about TheyFit?

While we are made from latex, people often remark how subtle any scent is. We also have the benefit of being blow-your-mind revolutionary custom-fitted condoms (95 sizes!) that for the first time offer a condom so comfortable men actually want to wear it. Imagine!

Currently not available in Canada, but I suspect some clever citizens are circumventing that.

Joe Nelson

Dear Joe,

Thank you for bringing your product to our attention. I love the idea of bespoke condoms (and of course they come from Britain – you people sure know how to tailor apparel!), and most men seem to love nothing better than to spend hours painstakingly measuring their dicks, so that’s great, too.

Folks, Joe offered to send me some condoms to try, but I’ve got no regular male lovers these days, so if you’re interested in testing some out for us, send along your measurements and I’ll send them off to him.

First come, first served. Or is it first served, first come?

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