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.
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.
THIS! I dated a guy who was not satisfied by vanilla sex. It’s hot and fun much of the time, but sometimes I wanted vanilla. And the bar keeps going higher and higher because he got bored so easily. I don’t know if someone like that could be content forever with one person.
On the upside, of you are up for it, you could learn a lot from a guy like this.
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Men are praised for the skills in the bedroom. Women are often chastised for it.
I, for one, have never and will never chastise a woman for enthusiasm and skill in the bedroom. More often, it’s a refreshing change.
But talking about, let alone asking for, anal and a three-way the second time in bed seems a bit too much, unless the woman hinted at it first. Anal has never done that much for me and while the few three-ways in the past have been amusing, at my advanced age it sounds more exhausting than titillating.
Though, I could probably rise to the occasion…
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Don’t really have anything to add except to say thanks for not shaming people, men or women, for pursuing their sexual desires.
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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.
Well, that depends. If a guy is awash in options, and especially if he’s had some exes that were down with it in the past, he’s logically going to expect more than some schlub who’s lucky to get laid once a month (like most of my married friends). IOW, if you won’t do it, how difficult does he think it would be to replace you with someone who will?
Will they take it if offered? Probably.
Some guys are seriously squeamish about anal sex, given that orifice’s primary function. Heck, some guys are squeamish about going down on a woman (in front), and that is certainly expected by many women. (OTOH, some women won’t let a guy do that, so it’s hardly universal.)
nor do they judge a woman for not wanting or liking it.
Some guys will judge a woman for that. Others may not mentally dock her any points for it, but we’ll give bonus points to a woman who is down with it, so the effect is the same.
As for the threeway, few men will turn that one down.
You’d be surprised. I’ve dated a number of bisexual women who’d had bad experiences with past boyfriends when they suggested it. IMHO, this is a sign of insecurity, and we all know there are lots of insecure people, both men and women, out there.
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.
Bah. All it takes is a few seconds of kissing and for me to tell whether a woman digs other women. And, frankly, most of the ones who do drop all sorts of not-so-subtle clues about it. That doesn’t mean she’s down with a three-way at the guy’s whim, but in most cases it’s just a matter of helping them feel secure in the relationship and waiting for opportunity to knock.
If they do [push for it], 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.
Indeed. Pushing for something after you’ve already said “no” demonstrates that he considers that thing (whatever it is) more important to him than your present relationship. Do note, however, that “pushing” is different from casually checking to see if your answer has changed–as women are known to do on a whim, especially as their own security in the relationship changes.
There’s nothing wrong with sharing sexual experiences as part of foreplay, which is what these two were doing. It’s actually pretty hot.
Ugh. I don’t want to know anything about a lover’s past experiences. That’s not foreplay; that’s an insult to my masculinity. Call me insecure if you wish, but I think most men would agree with me. You’ll get a lot further suggesting what we should do to you rather than telling us how much you loved what some other guy did to you.
You always run the risk of revealing too much and possibly intimidating your partner.
You also run the risk of encouraging your partner to share their own history and being intimidated yourself.
As long as everyone is on the same page and nobody breaks a law or gets hurt, it’s all good.
You might be surprised at what sexual acts are prohibited in some states; that’s not a good standard. Personally, I draw the line at children, corpses and animals. Consenting adults? Do whatever you want in the privacy of your own homes.
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.
OTOH, there are a lot of women who aren’t into those things, so those who are deserve some sort of verbal distinction. Tastes vary–and labels for others vary based on one’s own tastes. As a joke in the BDSM world goes, “I am erotic, you are kinky, they are perverted.”
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. … If he’s pushing for anal that quickly, it could be that he’s become desensitized to “vanilla” sex.
Or it could just be he wants to know that her sexual experience/openness is at least in the same ballpark as his. Sometimes, when someone asks a question, they’re more interested in your reaction to the question than in the answer itself.
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