Dear Di...
Dear Di,
I’ve been dating a virgin for a while now and the other night when we were fooling around in bed, she cringed as I tried to slip her the finger and could not go beyond my fingernail. That being said, I was wondering if there was anything I can do to make her “axe wound” not feel like an axe wound if deflowering ever takes place?
—Doesn’t Want to Be a Lumberjack
Dear DWBL,
If I sift through your mixed metaphors, I can assume you’re asking how to ensure her first time is all pleasure and no pain. Unfortunately, most women do feel some degree of pain the first time they have vaginal sex, even if they’ve masturbated, been fingered, or used tampons. However, as with most essential life skills—of which having sex is definitely one—practice makes perfect. Assuming she’s relaxed and enjoying herself, keep fingering her regularly, trying to go a few millimetres further in each time (up to your fingernail on Tuesday, up to your top knuckle on Wednesday, and so on). And when the time comes, you can certainly help make her cherry popping as painless as possible by entering her slowly and fucking her gently (yes, Jack Black had it right). And it’s absolutely essential that she be nicely lubed-up beforehand, either naturally or with a little help from Astroglide. Of course, it goes without saying that you should both be mentally prepared as well. Losing your virginity is a big deal, but the one who does the deflowering, as the non-virginal veteran, has a big responsibility to make the experience memorable for all the right reasons. So good on you for being so considerate. One last word of advice, though: “axe wound” is quite possibly the worst euphemism for female genitalia I’ve ever heard. It might grow on me, though—if you promise to yell “TIM-BERRRR!” when you come.
Love, Di
Dear Di,
Me and my girlfriend of five years have been going through a rough patch. It started at first with amazing sex in the earlier years, but lately the sex has gotten boring. It seems almost as if I don’t get turned on by her. I’m mostly tired of the usual same routine that we have when we do it. I recently found out what being “dominated” is and it seems very interesting and excites me, but my girlfriend has already told me that she only likes the same usual stuff. How do I convince her to become a “dominatrix”?
—Dominator Lover
Dear DL,
Any girl who deserves to be called your girlfriend should be more than willing to share, communicate, and compromise in the bedroom. She likes routine, so she’s apparently excused from indulging your kinks—yet you’re forced to suppress your desires and indulge her vanilla needs. Sound fair to you? Me neither. Look, you’ve been with this chick for five years, so by now you’re probably pretty good at being open and honest with each other. Try telling her, “I know you like routine, but I think we could spice things up once in a while.” Start with something tame, like plush handcuffs, so she doesn’t get too freaked out. That way you can both get what you want: you’re handcuffed to the bed in a submissive situation, but she can ride you as normally as she wants. Once she gets a little more comfortable with the idea, you can move on to the real fun stuff, like spanking and ball gags. This doesn’t mean your sex life will be all kink, all the time; you two will have to compromise and do a little missionary here, a little humiliation session there. If she’s not willing to cater to your kink at least some of the time, she’s worth none of yours.
Love, Di
If you have a question for Di, email deardi@thefulcrum.ca.
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