Ask Dr. Nerdlove by Harris O'Malley

Why Is Our Sex Life Out of Synch?

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 (; or to his email,