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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. I told him he could do it once and then I would decide whether to let it continue. So we tried it. It felt uncomfortable and it 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: You're gonna breathe deep, 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, and soon you won't be able to look at those 10 fingers of his without thinking about the orgasms you'll be having when you can only see nine.

 

I'm a bi 18 year old female. I can't cum during sex, I never have. Boys or girls it doesnt matter. I can get off by myself but with other people its just uncomfterable. Vagional penatration feels good but head or finger fucking is Not fun. I thought that it was just the people I was sleeping with. You know, age and a small town bla bla bla. I'm off to collage now and in a much biger city and nothing is better.

I Can't Cum

 

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 sex-ed classes: You can touch yourself during vaginal intercourse. Whatever you're doing that's getting you off when you're alone, do that thing 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 get you off.

 

I am a 24-year-old straight girl. My boyfriend is 31. We have great sex -- until the last two minutes. He can't get off without jackhammering me, so I grab something and hold on for dear life until he comes. I'm happy to do it to satisfy him, but it also means he never gets off when I'm on top, and we can't have slow, sappy sex every now and then, and it can be painful sometimes. I've brought it up a couple of times, but he doesn't seem to be able to finish any other way. Has it just been too long with a bad habit, or is there a way to bring his dick back?

Holding On Tight

 

There may not be anything wrong with your boyfriend's dick. Just as some women require intense, focused stimulation in order to get off (read: vibrators cranked up high), some guys gotta jackhammer. If your boyfriend is one of those guys, 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: 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, let him finish himself off by jackhammering away at his own clenched fist.

 

I am a woman in a relationship with a woman. There's someone else. I haven't cheated. But I cannot get them out of my head. They are directly in my life. And by "they" I mean "him." I dream about him, think about him. I try not to. But inside I know the truth. It's becoming hard to be in the same room with him.

So what would Dan do? What would Dan do if he were mind-cheating constantly?!?

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 destabilizing to our relationship.

So you probably shouldn't do what I would do. 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.

 

Some women like porn and some women don't mind it. For us women who feel like vomiting at the thought of porn, telling us to use porn -- or eat cupcakes -- will neither relieve the pain caused by our partners' use of porn nor meet our emotional and sexual needs if we opt out of relationships with men entirely. I've tried my whole life to feel OK about porn. I don't. I feel betrayed, just the same as if the cheating were "real."

Never Okaying Porn Ever

 

Porn isn't cheating -- but let's not argue about that. Instead, let me say this: 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, 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.

 

Find the Savage Lovecast (my weekly podcast) every Tuesday at thestranger.com/savage.

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