I Require My BF to Cum in Me… Help?

I’m a fan from Italy, so please excuse my English. I’ve been in a hetero relationship with my boyfriend for seven years, we’re both around 30, and we love each other and blah blah blah. Sex is very good but quite standard since we have no particular kinks or fetishes. I always reach orgasm before penetration, but only with fingering. It turns me on when he goes down on me, but it doesn’t “do the trick.” After I come, I feel something is missing if we don’t have penetrative sex that ends with him coming inside me.

But because that part isn’t a lot of fun for me—being penetrated doesn’t make me come, and I’m being penetrated after I come—I usually urge him to come quickly, which is a bit frustrating for him. Is it weird that I need this kind of “closure” to sex? Is it weird that I want him coming inside me under these conditions? Where does this need come from? I’m sure you’ll have a great answer!

—Weird Orgasmic Needs Defy Easy Rationales

You’re in a better position to judge where this need of yours comes from—and you’re most likely in the missionary position (not that there’s anything wrong with that!)—but if I were to hazard a guess…

Sex meets our physical need for touch, for pleasure, and for release, WONDER, but it also meets emotional needs. And sometimes what a sex act and/or an eroticized act symbolizes is just as or more important than how it feels. It means something to you—something important—when your boyfriend comes inside you during PIV intercourse. And since your boyfriend comes inside you after you’ve already come—usually after you’ve asked him to hurry things along—it’s not about your pleasure in that moment. It’s not about how it feels, WONDER, it’s about what it means. Your physical needs have already been satisfied; your boyfriend got you off with his fingers. But sex doesn’t feel real and complete for you until your boyfriend comes inside you. In the moment—in those moments—it’s more about what’s going on between your ears, i.e., more of what sex means than how it feels.

Seeing as you read my column, WONDER, you must know (I hope you know) that two or more people can have a satisfying and meaningful sexual encounter that leaves them feeling connected and satisfied without anyone being penetrated during PIV or PIT or PIB and without anyone coming inside anyone else. Indeed, a person can have a meaningful sexual encounter that leaves them feeling satisfied without coming at all.

But if you want to shake things up with the boyfriend—if you occasionally wanna give your boyfriend a chance to enjoy fucking you without being hurried along—you could always wait to come until after he does. Now, you’re a grown-ass, sexually active, thirty-year-old-or-thereabouts citizen of the European Union, WONDER, and I’m guessing this may have already occurred to you. But I’m going to toss it out there just in case: Let your boyfriend go down on you until you’re completely turned on, then let him take his time fucking you until he comes, and then—and only then—let him finger you until you come.

I’ve been with my partner for three years and we recently decided to dip our toes in the waters of swinging. We were on agreement about only doing a “soft swap” to start and then seeing where it led. We met up with a few couples and hit it off with one. At first my boyfriend was super respectful of my boundaries but he’s become obsessed with being on swinging apps all the time. He enjoys the “reality porn,” meaning the profiles, and that’s fair. But he’s secretive AF about it. If it’s all out in the open, why does he need to be secretive?!? I’ve broached the subject and the conversation always ends with him saying, “I’m sorry! I’m just bored! I’m not looking for anyone else!”

But his obsession is starting to affect my self-esteem. We have a stellar sex life, and I am a ravenous woman. It’s not like we have a “dead bedroom” problem here. I had a conversation with him last night about whether we need to shut the whole thing down. I said that if this is something he’d like to continue with on his own, then he’s free to do so—as a single man. I don’t want to hold him back if that’s what he needs in his life, but I’m also not going to suffer because of it. I don’t know what else to do. I’d love to hear your thoughts on navigating this.

—Seriously Worried About Partner’s Obsession

There are two possible explanations for why your boyfriend suddenly started being so secretive and squirrelly about what he’s doing on that swinging app. First, he could be cheating or planning to cheat. He could be doing something that violates the rules you hammered out when you opened the relationship, e.g., meeting up with a couple on his own, or he could be making plans to do something that breaks those rules, e.g., talking with couples about doing a full swap. Second possible explanation: Your boyfriend came down with a bad case of kid-in-the-candy-shop, got carried away, and knew, even before you said something, that this was annoying you. But instead of dialing it back, he’s tried to hide it from you. Dickful thinking may even have led him to believe that he was being considerate of your feelings when he attempted to hide what he was doing.

Either way, SWAPO, you issued an ultimatum—if he doesn’t knock this shit off you’re going to put a stop to it (the swinging) or put an end to it (the relationship)—and soon you’ll know what you have to do.

I’m a 60-year-old gay man with a 35-year-old straight male friend—and no, this letter is not going where you think it’s going. We have become best friends without benefits. We have a lot of common interests, and we enjoy doing things together on the weekend. I've never gotten any indication that he has any sexual interest in me and I'm not going to ruin our friendship by making sexual advances to him. Last year I went through a very difficult time personally, involving an illness and multiple deaths in my family.  He was there for me completely—really, above and beyond anything I could have expected. 

I would like to get him a gift to express my gratitude for his support and I can afford to be extravagant. The problem is, I don't want to get him something extravagant if there's a risk my generosity might be interpreted as a come-on. Our friendship works because we respect each other’s boundaries, and I don't want him thinking I've suddenly tried to cross one. So, here is my question: What does a 60-year-old gay man give a straight man half his age that will convey appreciation for his support during a difficult time in my life but will not convey a desire for sex?  Or is there such a gift?

—Fully Recovered And Thankful

It’s easier for me to rule things out than it is for me to rule things in, FRAT, seeing as that, save for his age and straightness, I know next to nothing about your friend. I mean, you already know not to get your straight friend a pricey leather sling or a shiny latex gimpsuit, right? You don’t need me to tell you that, do you?

So, besides pussy, what does your straight friend like? Does he like football? Get him a pair of tickets to see the team he crushes on hardest and encourage him to take a friend (or a date) that shares his passion for that kind of straight bullshit. Does he like video games? Get him one of those giant TVs straight gamer boys like to play games on. Does he like going places and is he fully vaccinated? Get him airline vouchers and give him enough cash to cover a nice hotel and food and tell him to go have a great fully vaccinated vacation on you. Or maybe there’s something he needs rather than wants—kind of like you needed emotional and logistical support during your illness and family tragedies? If he needs his credit cards paid down, pay ‘em down. If he needs his car paid off, pay it off.

And if you’re worried that he might misinterpret your generosity as a come-on or as a precedent (that lavish gifts will keep coming) or as a burden (that you expect lavish gifts in return), address all those possible misinterpretations in the card : “You were such a generous and giving friend during an extremely difficult time in my life and I wanted to do something special for you—just this once—to thank you. I hope we will always be friends.”

Finally, FRAT, there’s also the option of giving him something reasonable—maybe tickets to a football game counts—and then writing that straight boy into your will. He definitely won’t think you’re trying to get into his pants after you’re dead.

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