Dear How to Do It,
My wife is bisexual, and I’ve always been cool with her playing with other women, and sometimes other guys—we have plenty of sex, so I know it’s not about me. I’m usually a one-woman kind of guy myself, but recently we had a couple over socially and things got a little heated. My wife and the woman had fooled around before, but never with her boyfriend. I sort of figured we’d just watch, but then the guy put his hand on my thigh. I wasn’t really sure how to respond—I’ve never been with a guy and don’t think I’m interested—so I just left the room. My wife was a little upset; she felt I was too closed off to experimentation. But shouldn’t this kind of thing happen with lots of communication? I sort of suspect she and the other couple intended things to go in this direction, and I’m the only one who didn’t know. We have a pretty conservative background and our relationship is very unconventional in our world, so I’m not really sure of the ground rules. What should I do, in this instance and in potential future ones?
Dear Try Guy,
If I’m choosing sides—which I wish I could say I’m not inclined to do, but let’s face it: part of the reason why I’m here or anywhere is for the drama—I’m choosing yours. I don’t think your wife was necessarily wrong, per se, in perhaps devising a scenario where you might get swept up into the moment and fall into some man orifice. A lot of people respond to spontaneity. Who we are at our most aroused often doesn’t look much like who we are when flossing our teeth or folding laundry. Your wife might have even thought she was doing you a favor by giving you the opportunity to explore. But guess what? You didn’t want to! And guess what else? You don’t have to! Nor should you be pressured to do anything you aren’t comfortable with sexually. The risk she (potentially) took by springing a foray into bi play on you is that you wouldn’t take the worm (in this case, a dick). She should be happy that you chose the least awkward method possible of handling this by simply removing yourself. That’s to say, I don’t think she has a moral standing here to 1) surprise you with a male sex partner, and 2) give you grief when you don’t respond in the moment. (I’m basing much of this on your suspicious interpretation of the situation; it’s possible she was not conniving at all and you’re letting yourself get paranoid!)
From my perspective, you sound plenty open-minded. I would just check in, though, to make sure that you’re as open-minded as she needs you to be—perhaps she reacted a bit irrationally to your sensible reaction, but perhaps she’s responding to bigger-picture issues. Make sure you are clear about all of this. If you aren’t certain of the ground rules, it’s because you haven’t set them, which you have every right to do. So do that, too.
I would be remiss if I didn’t nitpick one more thing you wrote: “I’ve never been with a guy and don’t think I’m interested.” Think is doing some work here. If you are in fact curious, as this wording implies, you may want to do some introspection and eventually take your wife up on her offer. You’re very open to her exploring; you might want to grant yourself the same freedom.
Dear How to Do It,
Years ago, my wife fell into a bout of depression. Therapy and antidepressants helped, but her libido disappeared. All sexual (and then all physical) contact ended. It never returned. During marriage counseling, the truth came out: The antidepressants did nothing to slow her sex drive. She hated sex with me and saw a way to get out of ever having to do it again.
We’re divorced now. I’ve made peace with our relationship, learned to forgive her, and accept my own mistakes in our marriage. But now I’ve started dating again, and I find I’m paralyzed. I’m a man in his mid-40s who hasn’t had sex—who hasn’t even kissed—in 20 years. That fact is sitting there, at the front of my mind, during every flirtatious encounter, during every random Tinder date. I’m unable to let any date end with more than a firm handshake, and there is never a second date. As stupid as it sounds, I feel like everyone can look at me and see how un-screwable I am. I worry that even after I get over the mental block, the lack of experience and the lack of ability will still be there to disappoint whoever I eventually take to bed. How do I get past this and learn to move forward?
Dear Rusty Nail,
On the matter of your screwability mental block: You’re not the authority here. While ideally you’d have healthy self-confidence (it makes you more screwable, if nothing else), it’s other people who determine your desirability as their desire defines it. So if someone wants to screw you, you are, by definition, screwable. Trust others here. Open yourself up enough to let them lead when it comes to taking things further.
So now that you’re hypothetically past that, on to your stroke. I think it’s important to remember that most of the time in sexual scenarios that aren’t brokered to a T beforehand, usually in some kind of online forum, people aren’t signing up to have sex with a machine who executes its techniques flawlessly. You aren’t a gymnast, and your partner will not be behind a judging table (unless you’re into that, in which case you had better bring your A game). Most of the time, when people want to have sex with you, they want to have sex with you regardless of your special skills or lack of them. This isn’t science, per se; it’s about a more amorphous sort of chemistry—a great way to be good in bed is simply to show up, be you, and connect with your partner.
That will, of course, involve you getting out of your own head and living in the moment. Focus on relaxing. Consider therapy on your own, if you haven’t. And when you do learn to turn off these thoughts, pay attention to your partner’s desires, but in the frame of mind that sees sex not as an obligation but as a healthy vehicle for self-expression. You’re overdue.
Dear How to Do It,
I’m a gay guy in my early 30s who has historically been a bottom. My first boyfriend was a top, and when I did strike out on my own, my dick didn’t really cooperate when I tried to top, so I figured that was that. Recently, a mostly top man I’ve been seeing for six months—who I am somewhat crazy for—asked me to top him, and I just kind of … did. Then we did it twice more that day, and I loved it. That experience gave me enough confidence to try it out with other guys (we’re not exclusive), and I was disappointed to find that, once again, my dick did not show up to work. I am excited to be more versatile, especially because other guys have tended to assume I’m a top and it has led to some awkward situations. But I am wondering what I can do to help that process along and be more consistent, because my dick seems to have its own ideas.
Dear Aspiring Vers,
In the absence of a little more context here for these encounters, I’m going to make some assumptions. It sounds like topping the guy you’re crazy about was an impromptu experience, while there was planning involved with the guys that ended up not getting you up and leaving you down. It could be as simple as this: You really like that guy that you’ve been seeing for six months, so you felt comfortable topping him, and less comfortable, ergo functional, with the randoms. Or it could be something more to do with the circumstance, which is to say, perhaps you are a more spontaneous type of top. This would make sense, too. Performance anxiety is truly a silent killer … of boners. It could be that setting out to be the top is the problem, and that you may have to go into these situations leaving them open to positioning possibility. This shouldn’t be too hard; most gay guys are versatile to some degree, especially when you exude the kind of top energy that has guys bending over to your very presence in response.
I have noticed a certain level of intensity when I end up topping in a situation that I set out to bottom in. It’s like a switch flips midway through. I believe this is because if I enter a situation thinking I’m going to bottom, I feel absolutely no pressure to perform, so I can with absolutely no anxiety. And that makes me want to. There is also something about topping tops that is low pressure in itself. A self-identified power bottom who runs the entire session with the authoritarian perfectionism of a Kubrick set can intimidate the wood right off a guy whose sensibility isn’t complementary. A guy who calls himself a top but decides to bottom tends to be a lot more easygoing about it.
I’m not saying that you should set out to turn out as many tops as you can (talk about pressure!). I’m saying that our modern methods of hooking up have a way of compartmentalizing us into machinery whose parts are ordered to carry out specific functions. Reality tends to be more amorphous than that. So leave your options open and don’t be so hard on yourself. Just as you are a man, but not Superman, you are a top (occasionally) but not Supertop.
Nor should anyone expect that from you. My final suggestion to you: Don’t let other people’s expectations and assumptions dictate the sex you’re having. Versatility is great—I couldn’t recommend it more, and I’m proud of you for wanting to experiment with it—but other people wanting you to be something you are not is their problem, not yours. Don’t internalize the pressure they make you feel when they voice surprise at your preference for bottoming. It’s only going to make things harder, and make you softer.
Dear How to Do It,
I have an amazing boyfriend—he is a great friend and partner. But our sex life is barely there, and when we do have sex, it’s not great. He often tells me to just use him as I want when I want. This is too broad for me, and I’m shy about asking for sex. I’m happy everywhere but in our bedroom. It doesn’t help that an ex and I had a very kinky, hot sex life with role play—props, everything—and he was always open. I don’t want to compare, but I do miss the sex. I’m still in my 40s and I don’t want my sexual days to be over.
—Hate to Ask
Dear Hate to Ask,
It seems like you’re shy about asking for anything—there’s nary a question mark in your … microessay—let alone sex. Well, in the words of an extremely flawed, occasionally wise man: Shyness is nice, and shyness can stop you from doing all the things in life you’d like to. You have all the pieces here to ensure that your sexual days are far from over: 1) A true understanding of what gets you off from your previous partner, 2) a current partner who’s willing to do whatever, and 3) an interest in staying active. So stop wringing your hands and get in there. Just do what you did with your ex with your new guy. He sounds like a blank slate, so cover him in your tried-and-true kinks. If your ex was usually the party who led the fun, spell out to your current partner exactly what you need, per your past experiences, and ask him to do it—you’ll only have the discomfort of taking the lead that one time.
If you don’t take control of your sex life, you’re going to lose it. You’re hungry, and there’s a huge feast in front of you, but you can’t bring yourself to pick up your fork. If you sit there long enough, it’s going to get moldy and you’ll be left hungry. That’s no way to live, so don’t live that way.