Q: 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
A: 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 or toaster is wired the way your butt appears to be, POOTER, no amount of pit-, eye-, nostril- or 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.
Q: I am a 30-year-old woman with a strange problem. I recently started lifting weights, and every time I use the arm machines, I have an orgasm. It is not obvious to anyone else (I think), and my sex life is great outside of the gym. I don't know if I should stop using the machines, because it's rude and kind of weird to have that happening, but it just seems to be a physical reaction to using those muscles. What should I do? —Fitness Freaking
A: Another 20 reps.
Q: 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
A: 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 or eat you to create the sensations that are intense or focused enough to get you off.
Q: 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
A: 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.
Q: I am a woman in a relationship with a woman. There's someone else. I haven't cheated. I'm not a cheater. But I cannot get them out of my head. They are directly in my life. And yes, by "they" I mean "him." What the F, Dan! I dream about him, think about him. I try not to. I talk about my girlfriend and how much I love her in front of him. But inside I know the truth. It's becoming hard to be in the same room with him.
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?
A: 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- 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.
Q: Some women like porn and some women don't mind it. For us women who are otherwise GGG but 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 decide to 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
A: 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, NOPE, 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 Dan Savage’s weekly podcast every Tuesday at thestranger.com/savage. Send letters to firstname.lastname@example.org
Find Dan Savage's weekly podcast every Tuesday at thestranger.com/savage.