Q: A friend hooked me up with a much younger guy for weed. Let’s call him “Pretty Boy.” He knew something about me—Pretty Boy had been to a party at my house—and I knew something about him: he’s a burner, like our mutual. Consent is supposed to be a core burner value and before we hook up, Pretty Boy asks if he can bring his paddles. So, we had a talk and I told him I’m open to a little pain, but I’m mostly meh about it. (Except love bites. I love me some love bites.) Long story short: Pretty Boy thinks he’s a great fuck cuz he’s got a great big one and can pound long and hard. My pussy ain’t been touched in almost three years but so far as I know “OUCH” is the universal safe word! Maybe I should’ve picked a better one because I had to say it so many times! I figured it was heat of the moment stuff, so I wasn’t mad, and agreed to hook up again. Much more OUCH, but on both sides this time. (Love bites!) Next day I’m figuring out how to manage this. I find a thing called an Ohnut and I tell Pretty Boy I’m willing to plunk down the money. Whatever it takes to make his PIV pounding less OUCH. And then we have this conversation:
Sore Lady: “So, surely this has happened before, yes?”
Pretty Boy: “Of course it has. LOL.”
Now I’m mad. This motherfucker knew! He did it on purpose! I ask him point blank if he got off on it and he won’t answer. Which means he did. Now I want to set him on fire. But here’s the thing: Pretty Boy is the finest thing I’ve ever had the pleasure of putting my hands on in my entire life. I warned him that I have a history of channeling my rage into intricate revenge plots, most too crazy to carry out. I did rat him out to the dude who hooked us up. As for Pretty Boy, I could tell him to sit down, shut up, and hear my truth, but I already delivered that message. (See: OUCH.) I should probably slam the door and lock it, but he is the finest thing! And I’ve never had a hookup that wasn’t a little bit sketchy. But this is too much, right? RIGHT? —Boys Are Supposed To Ask Right, Dan?
P.S. I didn’t even cum either time!
A: So, Pretty Boy doesn’t care if you come or not, he ignores your feedback during sex, and he engages in rough sex knowing it’s sometimes painful—in a bad way—for his sex partners.
Fuck that guy.
By which I mean, of course, don’t fuck that guy. But you’re obviously tempted to fuck that guy again, BASTARD, as you make clear in your letter. (A letter I spent an hour editing for, um, clarity.) You wanna fuck Pretty Boy again because he’s the “finest thing” you’ve ever gotten to touch. Pretty Boy is so hot, BASTARD, that you’re tempted to fuck him despite wanting to set him on fire—in a bad way—after you spoke to him about the sex being painful.
Look, BASTARD, having a hot FWB is great, but having a hot FWB—or boyfriend or girlfriend or enbyfriend—who’s a shitty, selfish, inconsiderate lover is a lot like owning a house with an amazing view that happens to be right next door to a trash incinerator. Sooner or later you get used to the view and start taking it for granted, BASTARD, and the only thing you really notice after that is the stench.
Still, if you’re inclined to extend Pretty Boy the benefit of the doubt, BASTARD, it wouldn’t be hard to whip one up. He’s young! It’s entirely possible all the women he’s fucked up to this point in his short life liked his style, i.e., long and hard pounding! It’s also possible the women he’s fucked hated his style and, like you, hoped Pretty Boy would hear “OUCH,” stop, solicit their feedback, and correct course. Seeing that’s not something he’s either able or inclined to do, you’re gonna have to use your words and the actual leverage you have over him—your pussy, not your mutuals—to get him to fuck you without physically hurting you.
If he wants back in your pussy, tell him he has to do it/things/you differently. More foreplay, going slower, using lube, not going all the way in (with or without an Ohnut)—whatever he needs to do to make sex more comfortable and pleasurable for you, that needs to be a clearly-stated (by you!) and enforced (ditto!) condition of him getting anywhere near your pussy ever again.
And if he laughs it off, BASTARD, set him on fire*.
P.S. What happened to the paddles?
Q: I’m a cis woman in a relationship with a cis man for eight years. The sex is fantastic, mostly because we prioritize connection, play, and pleasure rather than penetration or orgasms, though we have plenty of both. My partner lasts a long time and only comes about a third of the time. About half the time we do PIV he outlasts both my own orgasm and the lube, meaning that I’ll stop things when the friction becomes painful and he’ll either finish outside of me or won’t come at all. These options work for us and the sex is consistently great! The dilemma is that we’ve decided to start trying to conceive, which requires him to come inside me. I’m worried that the emphasis on this one act will put so much pressure on him that sex will become less fun. I’m also worried it will make ejaculation even more difficult. Do you have any suggestions on how to make this more playful? Maybe a suggestion on how to get the lube to last longer? Is there a way to eroticize the whole process more? Or is subpar sex just an inevitable part of trying to conceive? —Conception Really Impeding My Pleasures
A: Subpar sex while you’re trying to conceive kindasorta comes with the territory, CRIMP, and it may be the least of your worries . . .
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