DEAR DR. NERDLOVE: I am a 25 year old homosexual male. My boyfriend and I have been together a little over a year and a half. I love him dearly but I’m not 100% positive that he’s the man I want to marry and start a family with. Herein lies the issue: he is sure.

Now for some background. This man has had a VERY turbulent childhood. I’ll spare you the gory details, but long story short his parents kicked him out and disowned him when he came out as trans. Needless to say, he didn’t really have a family before he met me. He’s told me on multiple occasions how I’ve given him a family, and I am so unbelievably happy that I’ve been able to do that for him.

However, I feel stuck.

Lately, I’ve been debating with myself if I want to pull the trigger and break up with him. I know this is gonna make me sound shallow, but part of it is because I miss dick, as he does not have one (he has a very small one that grew due to the hormones, but that’s besides the point) and will not entertain the idea of an open relationship. But the majority of it is because, ever since the pandemic hit, he’s been quite annoying and SUPER clingy. I’m not quite sure where it came from; he was never like this pre-COVID.

Like he’s told me, I’ve finally given him a family, and I have no idea how in the hell I can even BEGIN to take that away from him. And that comes in addition to the internal debate that normally comes with wanting to break up with a person.

I also thought it might be worth adding that he has told me multiple times that he would never break up with me. So, if either of us were to break things off, it’d be me. I don’t like that and, I’m no relationship expert, but that can’t be healthy. What if I were to royally screw him over in some unforgivable way?

Any advice on the matter would be greatly appreciated.

–Caught Between a Rock and a Hard Place

DEAR CAUGHT BETWEEN A ROCK AND A HARD PLACE: Let me ask you something, CBRHP: are you asking me for advice or are you asking me for permission to do what you’ve already decided you want to do?

I mean, I’ll put it bluntly: there is no way of breaking up with someone that isn’t going to hurt. Ending a relationship with somebody, even a relationship that needs to end, is a painful experience. There really isn’t a way to tell someone that you don’t want to date them any more that isn’t going to hurt. The scope and the length of the pain is going to vary depending on a lot of different factors, but it’s going to be there. The key is to avoid unnecessary pain, to make the process as quick as possible and — if you can — give him a place to land when the break comes. And honestly, I get the fear of leaving someone because you’re worried about what might happen to them afterwards. I’ve fielded a lot of questions from folks who were afraid to break up with their partners because they were worried about suicide, self-harm or otherwise leaving them worse off than they were before. I’m not unsympathetic, especially when that fear isn’t born out of an abuser taking themselves hostage to keep their partner around. But there comes a point where you have to ask yourself: how long are you going to stay in a relationship that you aren’t happy in because leaving your partner will hurt them? Another year? Five years? Twenty?

All that having been said: it doesn’t sound like any of the problems you have are insurmountable or unfixable if you want to try to fix them. You say you miss dick. Does it need to be biological dick? There’re a host of options available to give your partner (and you) a penis of just about any size that you might desire. Get the right harness for your partner and the two of you could have an entire smorgasbord of cocks of every size and shape for whatever whim the two of you might have that day. Hell, depending on just how much the hormones gave him, he could even get a penis extender sheath — think of a 3.5mm to 1/4″ plug adapter, except for your junk — that would give him him sensation during penetration and you the dick you’re looking for.

Similarly, the clinginess and be dealt with. “Where it came from” seems pretty obvious to me; it’s likely equal parts an understanding reaction to the COVID pandemic and the fact that he probably feels you becoming distant from him. Both of these are understandable. A lot of people are having complicated emotional reactions to life under COVID, especially if they came from troubled backgrounds. There’s nothing like a global pandemic to upend your (already) fragile sense of security and stability and leave you clinging for one of the few rocks in your life. Similarly, your boyfriend isn’t dumb and I don’t think you’re the poker player you think you are. The odds are very good that you’ve been acting differently as you’ve been thinking about breaking up with him. While this may not be the most productive way of handling things, when some people are afraid their partner may be pulling away from them, their instinct is to try to cling to them even harder. This doesn’t often help… but it is a common response.

And honestly there’s nothing wrong with being in a relationship when you aren’t 100% sure you’re ready to settle down and start a family. You (obviously) don’t want to make promises that you can’t or won’t be able to keep, but not every relationship is going to have perfect parity of emotion between both parties. That’s a thing that can often ebb and flow.

All of these things are issues that could be worked on. Your boyfriend could talk to a counselor about his anxiety  and the two of you could work with a sex-positive couple’s therapist to work on his clinginess, your need for dick and the question of where this relationship is going in the long term.

But again: that’s if you haven’t already made up your mind and you’re just reaching out for advice on how to end things.

If that’s the case… well, like I said, the best thing you can do is to make the break as quick and as clean as possible, and to soften the landing for him as best you can. You gave him a family, and that doesn’t necessarily need to come to an end. Presumably his new, found family consists of more than just you. Giving them the heads up that you’re about to break up with him and he’s going to need extra love, care and attention would be a kindness, and help ensure that he has the support he needs. But staying with him, when you emotionally have a foot out the door, isn’t doing him any favors. If anything, the longer you stay while you’re in that headspace, the worse it is for him. After all: how would you feel if you found out that someone you loved had spent the last however-long you were together wanting out but not leaving because reasons?

You have a choice to make here, CBRHP. If you aren’t sure you want to end things and you’re willing to try to fix the relationship, then commit to doing so. But if you’ve decided that you’re ready to leave and it’s just a matter of how… do it soon, do it fast and leave him with as much support and as many resources as you possibly can.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: I have an issue that I don’t really know how to process. Well, it might be two, depending on how you look at it. It makes me feel icky, for lack of a better word. I wanted to write in to you because I have a few times before and I have come to value your advice. Now, for the matter at hand.

My boyfriend, Darren, and I have been together for just under two years. He is a trans man and has not yet had bottom surgery, meaning he doesn’t have a penis. When we started dating, it was not a problem. But, as time has gone on, I have realized I’m not sexually attracted to him anymore and I miss it. I miss the feeling of “I’ve gotta have you, right here, right now.” I miss the feeling of looking at someone and wanting to tackle them onto the nearest flat surface and have my way with them. I don’t know if I can get that attraction towards him back. We don’t have sex. I’m not getting my needs met and neither is he. I’m a gay man, I’ve gotta have the D.

He’s agreed to an open relationship, where if we don’t have sex, that’s fine. Where “I don’t care what you do, as long as you come home to me.” That’s all fine and dandy. However, if I stay in this situation with him, I feel like I’m being selfish. I don’t want to keep him from someone who’s gonna be attracted to him in every conceivable way. He has told me that, with guys in the past, the minute he tells them he’s trans, they ghost. So he’s convinced that that’s never gonna happen. Not to mention, if we keep this up, there’s a very good possibility that someone is gonna get hurt.

I know what you’re gonna tell me. You’re gonna tell me that if I’m not attracted to him, I should break up with him. I wish it were that easy.

I’m not gonna sugarcoat this: He spoils me. Not only does he buy me nice things, but he is unbelievably sweet to me. Like he worships the ground I walk on. I’m not so shallow that my love can be bought, but I feel stuck. I almost feel like I owe it to him to stay together. I know that’s nonsense but I do. Also, I love him dearly.

Now, Darren has a friend named Tyler, who is very cute and who Darren has floated the possibility of becoming a throuple with. I, along with my boyfriend, am going to meet him for the first time this weekend. (Just to clarify, Darren has met Tyler. I have not.) Just the idea that that could happen is making me very excited. Giving me butterflies I haven’t felt since my first couple dates with Darren. I’m not sure how to go about this issue. I’ve never experienced anything like this.

Your advice would be greatly appreciated,

I Feel Like an Ass

DEAR I FEEL LIKE AN ASS: Right, this is gonna be a tough one.

So first things first, IFLAA: let’s talk attraction. Sexual attraction is one of those issues that tends to be incredibly nuanced; sometimes it comes hard, hot and heavy, where someone just flips your switch and your desire for ’em hits like a goddamn truck. Other times, it’s a slow burn; the more you get to know someone and spend time with them, the more attractive they tend to become to you. But sexual attraction can fade on its own too. Sometimes it’s like a star going nova: bright and intense, but fading quickly. Other times, it’s a slow fade over time, especially in the course of a long-term relationship. Esther Perel has famously talked about how familiarity, predictability and even security can dampen sexual desire in long-term relationships. It’s a perverse paradox that the things that help our relationships last can also be the things that diminish our desire for our partners.

But there’s also the fact that not every relationship is meant to be long-term. Nobody is carved in stone; we’re all growing and changing, constantly. The relationship that worked for you two years ago may not be the relationship that works for you now; the person you were then isn’t the same as who you are today. That can also affect your desire; you aren’t as into your partner because you’ve changed, they’ve changed and the relationship doesn’t serve the needs of who you both are now.

Now that having been said: it seems that you’re pretty firm that the biggest obstacle in your relationship is that your boyfriend hasn’t had bottom surgery yet and you’re into penises. I would have a number of questions about how much this affects you; is it the visual aesthetic, or are you needing someone with a penis that can actually get erect? Does it necessarily need to be a biological penis? Would Darren having a strap-on (or a packer or both) make it easier to bridge the gap for the two of you, if and until he gets bottom surgery and a phalloplasty?

That’s something you should consider, especially if you haven’t explored those options yet.

Now the second issue is the idea of your becoming a throuple and potentially having a poly relationship with this new guy, Tyler. The way it’s making you feel actually ties into what Esther Perel has said about familiarity… and one of the most common ways to bring the spark back in your relationship. One of the reasons why passion tends to fade in relationships is because as we settle in and get comfortable, we tend to… well, settle. The novelty fades, you both get comfortable and — critically — you stop having as many sexual adventures together. Introducing a third party — either as special guest or as part of a poly pod — injects novelty and adventure back into the mix, reigniting feelings that had gone dormant. Small wonder you’re excited, even without having met the new guy; this is the sort of novelty and thrill you two haven’t had in a while. So that might — and I stress might — be a potential solution.

However, I don’t think it’s a long-term one, or even the healthiest one under these circumstances. In fact… I’m kind of worried that you’re doing a lot of inadvertent harm to your boyfriend.

It’s pretty clear that Darren knows you’re pulling away from him. It’s also pretty clear that Darren has something of an anxious attachment style, especially considering he — understandably — worries that it’ll be hard for him to find another partner. I worry that he’s tossing option after option out there in order to keep you around… even though it may be cutting his soul to ribbons.

Case in point: your opening up your relationship. Asymmetric open relationships, where one partner is free to find sex elsewhere and the other chooses not to, certainly exist and thrive. So do companionate relationships, where a sexual connection simply isn’t an important part of the relationship. If everyone’s cool with the arrangement and everybody feels that their needs are being met… well, that’s how they roll. More power to ’em. But in this case, I think your seeking sex elsewhere and NOT having sex with your partner is… going to cause damage. In a real way, this is kind of a confirmation of what Darren is afraid of: his being trans is driving yet another man away. Spoiling you, opening up the relationship, even bringing a third party in… these all sound less like “Hey, we’re an adventurous couple and this is how we roll” and a lot more of “I’ll do whatever you want, just please don’t leave.”

And to be perfectly blunt: that’s incredibly unhealthy… and it’s s--tty of you to do to someone you care about.

Ask yourself which you think is more damaging: giving Darren the freedom to find someone who loves him and wants him for who he is, or a relationship where he knows that you’re not into him and would rather be with someone else. How long do you think you could take it if you knew that someone you loved was quietly dying inside the longer they were with you? How horrible would that make you feel to find that out?

If you can’t bridge the gap with Darren on the penis issue, then frankly, I think the kindest thing you can do is to end things. Dragging it out is only going to do more harm than good. And while I get that you appreciate the way he treats you… that’s a really s--tty reason to stay in a relationship, especially a relationship that may be damaging to him.

While I understand that you don’t want to hurt him, the truth is that there’s hurt and then there’s hurt. There’s necessary pain — such as, say, the pain of breaking up with someone — and then there’s unnecessary pain. Dragging things out, even in the name of trying to avoid that hurt, is the definition of unnecessary pain. And as much as the pain of a break-up hurts, a quick and clean break will heal faster and cleaner than a prolonged death by a thousand cuts.

Now who knows. Maybe Darren and Tyler will hit it off. Maybe you can help Darren find a good man who’s gonna be into him as he is. But you can’t count on that, and trying to stick around until you can find someone to cushion the blow is only going to drag the whole mess out.

I think if you really care about Darren, you owe it to him to see if there’s a way of filling that need for sex with him… or set him free so he can find someone who’s right for him.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: I recently reconnected with a sexual partner from my past. We’ve always kept in touch over the past 8 years, but are now trying to have a “normal” intimate, next level relationship.

The problem is …I enjoy quicker “activities” – let’s say 30-40 minutes, including foreplay. He prefers longer sessions and can go for hours without an orgasm. This hurts (he’s well endowed) and even though we try all the positions, 40-50 minutes (at least) of straight penetration is painful. I don’t feel like I’m turning him on enough (although he remains hard and assures me that he’s turned on). Unfortunately, my feelings of “inadequacy” are starting to wear on me. And yes, we’ve tried blow jobs and hand jobs to give my girl a rest, but even a 20 minute blow job (plus foreplay and penetrating), doesn’t help him get there.

The thing I’m worried most about is, I think it’s starting to affect both of us mentally. The other night when we were making out, I asked him to grab a condom and he declined sex…saying he didn’t want to disappoint me. Well, you can imagine how that left me feeling. Part of me thinks he’s okay having sex and letting me get off (even if he doesn’t), but another part of me can’t believe a man doesn’t want to orgasm (I mean, what about, “blue balls?!”).

I’m bummed about it. He says, don’t worry, we’ll get in synch. I don’t know if either one of wants to have sex anymore. Which makes me sad because we have an amazing relationship outside of this. But sex is important to me (and I’m assuming to him, as well). And before you ask, we’ve explored all kinds of foreplay, positions, places, etc…all of that is good.

I think that we’re both starting to experience mental blocks when it comes to orgasms. By the way, before we reconnected, he admitted that he’s always had a hard time reaching climax (but he doesn’t know why). He can reach it if/when he masturbates. And, says, he’s guilty of faking orgasms (with others) in the past. He said, he’s never faked with me — he’s only reached orgasms a couple of times with me; we eventually stop having sex because I’m too sore to continue. Hence, why I try to add other stimulation and find out what he’s doing himself that helps him orgasm when he’s alone.

I don’t know what else to do and I’m afraid it’ll become a problem that we can’t overcome.

Burning Out

DEAR BURNING OUT: Alright BO, there’re a couple things to dig into here. We’ll tackle the easiest one first: blue balls aren’t really a thing — at least, not to the point where folks with dicks and prostates NEED to get off or else we suffer agonizing pain. While not getting off can be frustrating, even a little ache-y around the testicles on occasion, there’re also plenty of times when it’s just not gonna happen, no matter what you do. Sometimes you’re just not going to get whatever x-factor is needed to push you over that particular cliff; at those times, it’s less about pain and more just “ok, I’m never gonna even get close.”

And hey, if he’s ok with not getting off — or taking care of things later — but he’s willing to make sure you have a good time? That’s the mark of a caring and considerate partner.

The bigger issue here is that you and your boyfriend have a sexual compatibility issue. Being sexually compatible is an incredibly important part of relationships; as you and your partner are discovering, when things don’t mesh up well enough, it can damage your relationship overall. The problem is that when we talk about sexual compatibility, we tend to think about things like mismatched libidos. One partner may want sex every day and twice on Sundays, while the other would prefer it once a month, and so on. But sexual compatibility also is about the kind of sex you want to have. If one partner is a dedicated kinkster and the other has a strict preference for standard-issue sex, then there’s a fundamental incompatibility that has the potential to damage or even destroy the relationship.

Similarly, if one partner likes to take things slowly and sensually and the other likes mad, passionate, throw-each-other-around-the-room sex, that can also be an issue.

Duration can also be an issue. Normally the problem is not lasting long enough… but this can also swing in the other direction. A lot of men get it in their heads that longer is better, period. This belief gets hammered into our heads over and over again, from porn to jokes in pop-culture, to hearing about how this celebrity or that can f--k like a champion for HOURS. But  — as you well know — duration and pleasure aren’t the same thing, especially when you’re talking about penetrative sex… and you’re the one being penetrated. While having some hang-time can be useful when a partner needs more stimulation, you hit a point of diminishing returns pretty quickly. Things start to get sore and chafe, lubrication starts to dry up and those sensations can go from “hurts so good” to “ow ow ow STOP IT” damn quickly.

It doesn’t matter what porn tells you; stay at it for long enough and you run the risk of leaving your partner dryer than the Mojave and feeling like a car engine with no oil after a road trip from LA to Vegas.

However, I suspect that the problem you and your partner are having isn’t strictly about compatibility. You mentioned that your partner prefers longer sessions and can go for hours. I want to zero in on this, because I’m wondering whether this is actually a preference, or if that’s an adaptation to circumstances.

See, you mention that he told you that he’s always had problems reaching orgasm through partnered sex, but has no problem when he’s masturbating. That, I think, is an incredibly important clue. I strongly suspect that your partner may have what urologists call “an idiosyncratic masturbatory technique.” You might know it by the name Dan Savage gave it: death grip syndrome.

This is a common issue in folks with penises. They get used to masturbating in a way that uses friction or pressure or other sensations that the human mouth, anus or vagina can’t match. Sometimes it means grasping the shaft incredibly tightly. Other times it may involve using a textured object — anything from a wash cloth to a pillow to inserting themselves between the mattress and the box spring. If someone does this for long enough, they can functionally train themselves to need that particular texture or pressure in order to orgasm. At that point, it becomes difficult, even virtually impossible, to achieve orgasm during partnered sex. This can be frustrating for them and demoralizing for their partner, who often feels like they’re at fault somehow.

Fortunately, the cure for death grip syndrome is fairly simple: they have to retrain their penis. This is achieved by abstaining from their usual masturbation technique — or possibly from masturbation entirely. They can have partnered sex, but they also have to be willing to go without the sensations that lead to their orgasm. By functionally starving themselves of that sensation and denying themselves that orgasm, they’ll often reach a point where their penis will start responding to more typical stimuli and orgasm that way. Of course, this means that they have to forgo their old jerk-off technique for good, otherwise all they end up doing is reinforcing that groove they carved in their brain.

However, it’s worth noting that some folks just have a difficult time reaching orgasm. Just as many people with clits and vaginas require a lot of intense, direct stimulation in order to get off, some folks with penises can need a lot of time or sensation to pop their corks. That’s just how they’re built and wired.

Now that doesn’t mean that they’re stuck wearing out partners who may not be into the marathon f--k sessions they need. One of the options available to the two of you is to vary up how you have sex. And while oral sex and masturbating can get just as exhausting, those aren’t the only options available to you.

I recommend you incorporate toys in the bedroom. To start with, look into getting a masturbation sleeve, like a Fleshlight or a Tenga. There’re a number of options that offer different levels or types of sensation; a number of toys even allow you to adjust the level of pressure or suction from the toy. You can use these as a warm-up to help get him closer, a way of giving yourself a break, or even switch things up between you and the toy and let the different sensations pull him over the cliff.

You might also want to look into anal play and some buttplugs. Butt-plugs, once inserted, put pressure against the prostate, which produces seminal fluid and causes ejaculation during orgasm. Having that in during sex means that the plug will press up on his prostate while he’s having sex with you. The pressure of the plug combined with the nerve-endings surrounding the gland AND the sensation of sex with you could mean that he won’t need to go for hours to get off. And — as a bonus — the pressure against his prostate tends to lead to some truly thunderous orgasms for him.

My recommendation is that you take explore both options, possibly even simultaneously. Having ways to take the pressure off (and friction) off of you during sex and to overcome any death-grip issues can help the two of you overcome this obstacle and get into the groove in bed again.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com