August 18, 2010

My boyfriend and I are straight college students, and he’s always wanting to try new things. Recently, he asked to put a finger in my ass while we were having sex. Someone did that to me before, but it felt uncomfortable and it kinda hurt. I told my boyfriend that he could do it once, and then I would decide whether to let it continue. So we tried it. It still felt uncomfortable and still kinda hurt. But I never came so hard in my life!

Now the question: If it’s uncomfortable, but it made me feel amazing and come really hard, what should I do? Continue with it? Or tell him to find some other way of getting me to that point again?
Presently Obsessing Over Totally Extreme Reaction

You could ask the boyfriend to stick a finger in one of your armpits—or in an eye, a nostril, your toaster—but unless your pit/eye/nostril/toaster is wired the way your butt appears to be, POOTER, no amount of pit/eye/nostril/toaster fingering is gonna jack up your orgasms quite the way that finger in your butt did.

So here’s what you’re gonna do, POOTER: You’re gonna breathe deep, you’re gonna take things slow, you’re gonna use more lube, and you’re gonna spend more time warming up the outside of your butt before anything goes in. (Tell the boyfriend he can finger your butt for 10 minutes after he rims it for 20.) Do it right, POOTER, and pretty soon you won’t be able to look at those 10 fingers of his without thinking about the kick-ass, anal-enhanced orgasms you’ll be having when you can only see nine.

Another 20 reps.

Off to collage, are we?

Here’s something you may not know about vaginal penetration—besides how to spell “vaginal” and “penetration”—because it’s not something that’s typically covered in small-town, high-school sex-ed classes: You can touch yourself during vaginal intercourse. Whatever you’re doing that’s getting you off when you’re alone, ICC, do that thing—touch yourself that way—whenever a sex partner is penistrating you vaginotionally.

And when you’re enjoying sex without penistration—when someone is eating your pussy or fingering your pussy—give that person direction, i.e., put your hand over his hand, place a hand on the back of her head, and show them just how to touch you and/or eat you to create the sensations that are intense or focused enough to get you off.

There may not be anything wrong with your boyfriend’s dick, HOT. Just as some women require intense, focused stimulation in order to get off (read: vibrators cranked up high), some guys gotta jackhammer to get off. If your boyfriend is one of those guys, HOT, then there’s no bad habit to break. It’s just something you’ll have to accommodate.

But he needs to accommodate your desire for some slow, sappy sex now and then. And here’s how he can do that: The boyfriend fucks you, long and hard, nice and slow, you get on top if you like, and after you’ve gotten off once or twice or three times… he pulls out… and doesn’t come, at least not inside you. If he’s aching to come, or you want to see him come, then let him finish himself off by jackhammering away at his own clenched fist.

So my question: What would Dan do? What would Dan do if he were mind-cheating constantly and experiencing intense feelings of attraction to someone else?!?
What Would Dan Do?

Dan would go to his boyfriend and say, “Hey, honey, it’s been ages since we’ve had a three-way…”

But that’s easy for Dan to say, because Dan’s a man and so is his boyfriend, and anyone Dan couldn’t get out of his head would be a man, too. That makes any hypothetical mind- and/or body-cheating on my part less threatening to my boyfriend, and less destabilizing to our relationship.

So you probably shouldn’t do what I would do, WWDD. Instead, you should masturbate furiously, avoid being alone with this man whenever possible, and don’t take the wife to see The Kids Are All Right.

Porn isn’t cheating, NOPE—but let’s not argue about that.

Instead, let me just say this: You shouldn’t give up on men, NOPE, because I occasionally get letters from men who think a fag sex columnist is interested in hearing them repeat what the insecure, controlling women in their lives have trained them to say. (“There are men out there who don’t use porn, and I am one of them!”) If you hang in there long enough, PORN, you’ll meet either a guy who honestly doesn’t watch porn, or a guy who says all the right things (“There are men out there who don’t use porn, and I am one of them!”) and is conscientious about clearing his browser history.