Why you should care
Because while good sex is great, bad sex is eternal.
Can You Lend Me Your Wife?
EUGENE, SIR: A friend of mine recently let me know that he’d “lend” me his wife if I wanted. He had talked to me about some version of swinging before, but I thought he was joking. We’ve known each other a couple of years, and this had not come up before. How would I even go about doing this? I asked him if his wife was into it. He told me she was his “slave” and would do what he wanted and if I wanted he’d send her over. She has never seemed very attracted to me, and I think I’d like to talk this over with her first, so should I ask for that first just to make sure all is kosher? —Confused Over Cuckolding
Dear COC: You, sir, have slipped down a rabbit hole, and the only way to get comfortable with this new place you are in is to “go with the flow,” which is to say: cease any and all efforts to normalize this experience. On the one hand, sex between consenting adults is one of the most normal things ever. On the other hand, all of this stuff, as I have past counseled, requires a good amount of thought — so thanks for the letter.
First off, your concerns are NOT unreasonable. This is not your standard fare. But rather than laying it down like a lawyer and making sure all of the T’s are crossed and the I’s are dotted before you have started, act like you have been there before, relax and check the lay of the land. I am assuming you are single since you’ve made no mention of a partner, or at least this has not factored into your calculations. So if she shows up as has been spelled out, invite her in. Is she in “character”? Is she dressed for the occasion? Does this seem like her scene?
If this passes muster, ask her to remove her clothing. If this was an extended practical joke, most people NOT in on the joke would balk at being asked to undress. Ask her if this is OK. If she says yes, then continue. If she says no, then stop. If she doesn’t say anything, ask again until you get a verbal response. You are part of another couple’s fantasy, but this doesn’t have to be your fantasy. It does, however, have to be legal. Film it, if they’re OK with this, as an extra measure of safety for all involved.
Now, if all of this works out, well, then mark it down as a success and keep on keeping on. Important to remember now: You all are not dating. Which is to say, thank them — when she leaves and him when you see him next — but don’t assume this is a continuing deal, unless they tell you so. Also, use a condom, don’t blab it around town and don’t ask if you can do it again unless they ask you if you WANT to do it again.
Got it? Good!
Back [Door] to the Future
EUGENE, SIR: I’m 26 and just got out of a two-year relationship. I might be in the minority here, but I enjoy anal. The problem is I haven’t enjoyed it since getting out of my two-year deal. If I ask for it, guys freak out. If I don’t ask for it, most seem too scared to initiate, and on the two occasions I got it to happen, they were terrible and either too tentative and gentle or too rough, and it was just not at all what I was used to. Is there any way to school new lovers on how to do this right? —DK
Dear Denmark: You know what’s easy? Maybe a handjob. In general, a dying art since it’s not the 1950s anymore but doesn’t change the fact that while getting anyone to orgasm can be complex, but getting the sex act started? Piece of cake. Or, more precisely: hand, penis, motion, game on.
Anal? A little more complicated and partially for the reasons you cite but more importantly for the nonsexual skills one needs to bring to bear about a successful conclusion: patience, sensitivity and a laserlike focus on how it’s all being received. Failing to bring all of these to the party creates a strong likelihood that the party will suck. For everyone, actually.
Can you teach patience, sensitivity and laserlike focus? Well, look, if you’re in a long-term relationship, these are skills that can be developed over time. But if it’s a hookup? Crapshoot city.
So pulling a page from advice columnists of yore, I’ll say this: bookmark this column and show it to the next person you’re thinking about inviting in, and, to quote Hamlet, “If they but blench, you know your course.” If they don’t “blench,” you might have yourself someone who is educable, also known as a keeper. At least in the ass mastery department. Good luck.
Sex With Sex Workers
EUGENE, SIR: Are there any significant downsides to dating a man who has spent a lot of time in his past using sex workers? —Name withheld by request
Dear Skeeved: I’m guessing here that in casual conversation, it was said or revealed that someone you’re spending time with was a whoremonger? Some would tell you to have disease concerns, but you could and should have these with just about anyone. Sex workers come from Planet Earth and as such are no better or worse than the rest of us. Unless you mix in drugs, drink or anything that would also complicate things sexually with a non-sex worker.
Nah, we’re largely all in the same boat. Now if you’re worried it might change how he views you, well your feedback on this would be immediate and direct and can be summed up simply with this question: Are you feeling good about your relationship? Yes? If so, proceed. If not, then don’t.
Outside of that, gets tests, use condoms and have fun. If his history with hookers starts to weigh too heavily on you though, perhaps move on. But in the absence of any obvious problems, why cause some?