I love having anal sex with women. It’s something intriguingly hot to know a girl is getting off by having a boner in her bum. About 95 percent of the time they dislike it because of the pain, which I sort of expect. The five percent of the time when she does like it... well, it’s ridiculously amazing. Is there anything I can do to get that five percent up to like a hundred?
Well, it’s my experience that women fall into three categories when it comes to anal sex. There are those who are “Into It,” which are your five percenters, though I suspect it’s higher than five. Then there are those who are “Not Into It.” Some ladies are just ooked out by buttholes, and you’ll never change their minds. Luckily, the vast majority of people are in the third category: “Into the Idea, But Nervous About the Execution.”
The important thing to remember about these Category Three people is that to sway them, you need to make the experience pleasurable, both physically and emotionally — don’t be all pushy and needy and weird about it. For the physical part, memorize an anal sex advice book such as Tristan Taormino’s Anal Sex for Couples so that you are a pro at making it not hurt. Emotionally, just don’t be desperate about it, you know? Nobody likes to feel like you’re only interested in them for their a-holes. If you pressure someone into trying something, then they’re not going to be relaxed and open-minded. In general, a good rule to remember is that most people like being pleasured. Make something pleasurable, and they’ll be into it. And don’t be a creep.
I'm a 31-year-old lady, often mistaken for a 25 year old. And although I get eager looks from men in public, I haven't had any sex for three years. I party, have friends, but can’t find a man for either casual or serious sex. I feel like my youth just passed me by. I have a crush on a 27 year old who I invite to casual events like films, concerts, and parties, but he only shows up when it’s work related. I'm a producer, so I hire him a lot, and there is sooo much attraction it’s crazy. I haven't felt like this for years. This is pathetic, I know. Please help.
Ok, look, you’ve got two separate problems here. Number one is that you like this dude who seems not to like you. I don’t know why — relationship questions are out of my purview, for the most part.
But as far as the sex thing goes, first of all, please don’t say stuff like “I’m 31 and my youth has passed me by.” People who aren’t old but think they are make me want to kill myself: 31 is not old.
However, you ask a good question. Because there’s this idea in our culture that men have to work hard and buy stuff and pretend to be interested in Gray’s Anatomy to get laid, whereas horny girls can just snap their fingers and have a willing guy appear with his pants already down. As you’ve figured out, this is not the case.
But unless you have something you’re not disclosing about your physical appearance, like you are mega-obese or missing a face or something, then you can get some. You just have to ask. When I was in college and trying unsuccessfully to slut it up, my male friends kept advising me to just ask a guy. I thought they were being metaphorical, but no, they meant literally say “Would you like to have sex with me?” to someone I liked. Weirdly, it worked.
The trick is that you have to be willing to take rejection, and socially sensitive enough not to be creepy about it. You sound good on both counts. Once you break your streak, it’ll get easier and easier. Just be confident, and godspeed.