I have a question for you. This is a bitter sweet moment if there ever was one. I recently started a relationship with a great guy who shares my passion for words. Unfortunately, to date, we have tried to have sex five times, and every time has ended in me screaming for him to stop because it hurts too much. My last boyfriend was average-sized, and we got there eventually after lots of frustration. The current boyfriend is a lot bigger and very sweet and patient about the whole thing. But a) I'm skin-crawlingly horny and b) I feel like a terrible tease.

So what can we do? My friend—who also has an over-sized partner—recommended lube. The boyfriend thinks we should just try to fit one more finger in every time. I'm very close to suggesting I should just get high on Nyquil so I can't feel a damn thing. What's your professional opinion?

Mismatched Puzzle Piece

My response after the jump...

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Lube. Lube, lube, lube. LUBE!

Your friend's suggestion is perfect. Trouble with penetration? Lube is always a good place to start—lots and lots of lube, even if you're the proud owner a self-lubricating orifice and that happens to be the orifice you're trying to stuff something in. Yes, lube. LUBE!

No, no, NO to your boyfriend's terrible, no-good, lube-free suggestion. An additional finger every time? If you're having a hard time squeezing his cock into your vaginal canal right now, MPP, jamming an extra finger in there "every time" isn't going to help. His "bone," however large it might be, has a little more give than his knuckles, which are made out of actual bone.

Frankly, MPP, it worries me that your boyfriend objected to additional lube. (I'm inferring that he objected, hence your not having used lube yet and his plan to get both his fists in your twat in ten days or less.) If he's one of those boys who's insecure about not getting 100% of the credit for all the wetness down there, MPP, I'd advise you to spare yourself a lot of grief and DTMFA now. But if that's not the issue and/or you wanna keep seeing him...

Definitely get some lube and use it—but not for vaginal penetration, MPP, not yet. Here's what you're going to do with your lube first: you're going to spend at least a month having fun, pleasurable, mutually-satisfying sexual encounters with your boyfriend without sticking anything in your vagina. You're going to have oral sex, you're going to masturbate together, and—most importantly—you're going to have some vaginal-intercourse-simulating frottage sessions: lube your upper thighs and that space between your asshole and your twathole, clamp your legs around his cock, and let him fuck the shit out of your legs while you play with your clit.

You're not going to get anywhere—you're never going to ever be able to relax and take his dick—if you wind up screaming in pain every time you're in the room with his dick. Back up and do shit that allows you to enjoy his dick. Then, after a month of other exploring and enjoying oral, manual, frottage, give vaginal penetration another go. Take it slow, use lots of lube, fuck for as long as you can enjoy/stand it, take oral/manual/frottage breaks as needed, then give vaginal penetration another go. Repeat until you're loving it.