A Troubleshooting session today involved an intriguing scenario. My client, a 37 year old female in NYC, asked me to share her situation here. Here’s the story:
Girl meets man on OKCupid. Girl is fresh out of a relationship and looking to casually date. Girl feels man is more sexually experienced than she is. The second time they slept together he asks her for anal sex. During a fantasy swapping session, he reveals his experience with threeways and anal sex.
My client’s question was whether or not anal sex and threeways were now expected options on the sexual menu.
Let’s answer this woman’s initial query. No, anal sex is not something men expect. Unless they are skilled in the ways of backdoor lovin’, anal sex is not especially pleasurable for most people. Done incorrectly and it can cause a great deal of pain and anxiety. Handled with care and a little flair, it can work. But that takes a lot of patience and understanding. For most men, getting straight sex is a chore in and of itself. They’re not going to make things harder for themselves by demanding or expecting anal sex. Will they take it if offered? Probably. But the do not demand it, nor do they judge a woman for not wanting or liking it.
As for the threeway, few men will turn that one down. I think most men make a play for the threeway. They usually start by asking a woman if she’s ever experimented or fantasized hoping it will open some Sapphic Pandora’s Box. Most guy’s won’t push for it, though. If they do, and you’ve made it clear you’re not interested, take that as a warning sign that they’re going to be looking elsewhere or that you and he might not be sexually compatible.
Now let’s attack the more concerning issue for me:
There’s nothing wrong with sharing sexual experiences as part of foreplay, which is what these two were doing. It’s actually pretty hot. You always run the risk of revealing too much and possibly intimidating your partner. You have to be sure they know that whatever you and they have been doing has been working for you and make sure they don’t feel like you’re pressuring them. I’ve often advised women here to reign in their prowess the first few times they hook up with a new partner. If you’re too good, they’re going to wonder how you got that way. Men are praised for the skills in the bedroom. Women are often chastised for it. Personally, I don’t date men who think like that. I find them tedious and exhausting. If I have to sit and worry about his fragile ego I’m not going to enjoy it.
Requesting anal on a second sleep over? What ever happened to tuning in to OnDemand and ordering a porn? Maybe throw in a facial for good measure? Christ on a Tricycle. That’s a pretty high bar to set for a new lover. He obviously told this woman that story for a reason. He wanted her to know exactly what gets him off. If she can’t live up to that, she should probably turn back now.
You don’t have to post a sexually explicit profile on OKC to receive bizarre emails from guys who clearly want to cam and jerk off or who just want to send random women pictures of their penis. Everybody has their kink or fetish. As long as everyone is on the same page and nobody breaks a law or gets hurt, it’s all good. For the record, I don’t consider spanking or anal sex or hair pulling or facials “kinky.” I actually think they’re pretty mainstream. I roll my eyes up into my head when I hear women bray about how kinky they are because they like to be spanked or have their hair pulled. Equally Yawnworthy are men who write those Christian Grey inspired dating profiles promising to re-enact scenes out of the movie Secretary. Oooooh. How 2002. Seriously. Just because you dated a guy who likes to call you a slut and spank you doesn’t mean you’re D/s (Dom/Sub) experienced. Whatever. Get shackled to a wall and paddled then tell me how kinky you are, kids.
I advised her to approach this guy with caution. There’s a big difference between a guy with a high sex drive and one with an insatiable sex drive. If he can’t be sated, then he’s always going to be looking for something beyond what is typical in order to get off. That could lead to some reckless behavior down the road. She needs to check in with him and make sure that he’s satisfied. He needs to do the same. If he’s pushing for anal that quickly, it could be that he’s become desensitized to “vanilla” sex.