How to Plan the Perfect Whipping

How to Plan the Perfect Whipping

Why you should care

No one hates bad sex more than the person you’re bad sexing.

Putting the S Into S&M

EUGENE, SIR: My husband and I are all about exploring our kink 11 years into our relationship. We’ve been playing with BDSM and one time last month things got carried away, I think, and after it was over I could see that I had whipped him bloody. For a few days after, he had to keep his suit jacket on and wear bandages under a T-shirt under a dress shirt so he didn’t bleed through. The thing is, he never used the safe word, and in general he is OK with how things worked out, but blood is real and I don’t want to really hurt him. Even if he wanted more, I think I can’t be the one who gives it to him, but is there something I can use that delivers the same kind of pain without the blood? I can see he needs/loves this, but I can’t bear wounding him so badly that he has to wear bandages after. —Madame X

Dear MX Missile: Anything that can be used to whip someone enough that that someone can feel it is likely to also be able to draw blood. Whip him with a feather, no matter how much elbow grease you put into it, and you’re not likely to be able to do what you did. So reverse-engineering this, it’s unlikely you’ll find (or I’ll recommend) something that delivers the sting without also, in over-application, breaking the skin. This is why bondage, discipline, sadism and masochism, or BDSM, as practiced, is something of an art.

An art that requires planning, practice and probably more attention paid to successfully concluding business than so-called “vanilla” sex has on its best days. Which is a long way of saying that if you’re going to play like this, it’s your job to plan your play so that what happens is exactly what you mean to happen. But sex is funny and in several types of best-case scenarios, you learn about things you like without knowing you’ve liked it so that you emerge from an encounter after having been beaten bloody discovering that you love being beaten bloody.

Which could be why your man didn’t complain at all. And which is why I suspect your complaints are connected to NOT knowing that it would play out in very real flesh terms, as it did. But, I imagine, if this had been precisely what you had planned, well, it would have been OK. So if it’s OK with him, and would maybe be OK with you if you could manage to do it without being surprised, or drawing too much blood, then, next time? Pay attention to the angle, the force, figure out which spots on the back are likely to bleed sooner than others and within those precise parameters. Have a blast.

Oh yeah, there are also S&M professionals who might help you in a much more direct way if you find my advice lacking. Which it isn’t. But you should. If you are. Good luck either way, though!

Eye, Eye, Cap’n

EUGENE, SIR: My man likes to look into my eyes when we make love and I hate it. How much do I hate it? I can’t orgasm or even get close if he’s looking at me, and I mean into my eyes. He says he can’t help it and it’s about bonding, but it makes it hard for me to relax and if I can’t relax, then I can’t orgasm and I don’t know what the big deal with all the staring is anyway. What compromise would work here? —Don’t Look

Dear See/Hear: Well, now it’s a thing. So, I imagine, now he’s self-conscious and you’re tense and waiting for it and he’s tense and trying to pay attention to what he’s not supposed to pay attention to and if you’re halfway to a surrender, and not a compromise, like I suspect, maybe you’re even trying to sneak a few screws in, in total darkness. A circumstance that may eliminate the unwanted eye. But right now you’re both eye-obsessed, and not in a very helpful or useful way.

But there’s a way out! You don’t mind being looked at, really. You just don’t like being stared at, I guess. So the way I’m breaking it down, if he’s looking in your eyes, he’s staring, but if he’s looking at your body, you’re fine, yeah? While the eyes are a romance, the body is what got you both there in the first place. By which I mean that it’s the somatic that gets us to cross the room and say hello. So him watching your body and what you two are doing? That’s fine. But giving you the Dracula Eye during sex, what you call staring? Not so fine.

Which sounds like the making of a perfect compromise and one that you should suggest when the tension levels have dropped a bit.

An Affair to Not Remember

EUGENE, SIR: I’m having an affair with my ex-business partner’s wife. One night a few weeks ago we were almost caught. She explained it away and it was a scare, but now I think we should stop, or confess. She thinks we should do neither, but I hate to sneak and I think it’s more honorable to confess. To my wife as well. Thoughts? —VN

Dear Very Nice: Ho-ho-ho … honorable, he says. Tell me, do you think papering over the dishonorable with the honorable results in an overall increased level of honor? Like if two wrongs don’t make a right, does one wrong and one right equal out to something sort of right-ish?

I don’t know, VN, but I do know this: Some affairs, if they’re not discovered, sometimes just blow over, with very little obvious damage done. People who study this kind of thing have even pegged most affairs that are not just dump-and-runs at a time limited to 18 months, more or less.

So while ethics is not my specialty, I can say that visiting discomfort on the blameless to make yourself feel better seems shitty. You had a scare, which caused you to reevaluate and as part of that reevaluation you’re thinking of clearing the air because that will make everything better? Don’t think it will. If you want to end it? Do so. But if you want to blow everything up and plunge four people, two of whom are largely blameless, into months of misery and uncertainty, then do what you’re suggesting should be done.

But me? Well, I’m a peace lover and love keeping the peace. But you should ultimately let your conscience be your guide.


Square pegs. Round holes.