Q: My boyfriend and I are straight, 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 kinda hurt. I told my boyfriend that he could do it once and then I would decide whether to let it continue. 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 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/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.
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. 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?
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 and/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. 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. But I cannot get them out of my head. They are directly in my life. And yes, by “they” I mean “him.” 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?!?