Q I'm 20, straight, male, fit and active. I masturbated prone—flat on my stomach—for years. I've now changed to a more traditional position (on my back or sitting upright), and I'm using my hand rather than grinding against a mattress. I can easily orgasm when I masturbate. I've had sex four times in my life, and I'm worried because I wasn't able to orgasm by someone else's hand, through oral or during penetration. I felt more sensation with oral or by hand than I did during intercourse, but I wasn't able to get off. This is extremely worrying, and I am increasingly depressed. Am I broken? Is my sex life ruined? —Boy Reeling Over Kaput Equipment
A You're not broken, BROKE, and your partnered sex life, which has barely begun, isn't ruined. Even if you're never able to cum by someone else's hand, mouth, twat or ass you can still have a rewarding and pleasurable sex life.
In the short run, BROKE, you need to be honest with your sex partners about the way your cock currently works. Let them know you're going to be mixing some manual self-stimulation in with the vaginal/oral/anal penetration. In other words, at some point you're going to pull out of whatever you're in, you're going to jerk it until you reach the point of "orgasmic inevitability" (OI), AKA that split second between the start of orgasmic contractions and the good stuff spurting out, and then you're going to put it back in. Since most women need to mix direct clitoral stimulation with penetration (or in place of it) in order to get off—before, during, after or instead of intercourse—your honesty about what you actually need to get off will signal to your female partners that they can be honest with you about what they actually need to get off.
Backing way the hell up: The way you used to masturbate—prone—is likely the reason you're having difficulty climaxing now. But lots of men who masturbated in more "traditional" positions—on their backs, sitting up, standing up—have trouble transitioning to partnered sex from solo sex. The inside of a mouth, vagina or butt doesn't feel like your own hand (or a long-suffering mattress, in your case), and even someone else's hand doesn't feel the same as your own. While the excitement of partnered sex helps most guys get over the hump—for many men, it takes time and a little experimentation for their cocks to adapt. But men who engaged in "atypical masturbatory behaviours" as boys—and prone masturbation/humping a mattress counts—frequently have a harder transition to partnered sex.
There's a name for what you're experiencing: delayed ejaculation. And while delayed ejaculation can be frustrating, the opposite problem—premature ejaculation—is more frustrating and harder to work around. And, really, when you look at it from a different angle, your problem—being able to last forever—is really kind of a superpower. Because let's say you fuck some lucky woman for ages, and she gets off again and again because someone—you, her, a third—is stimulating her clit at the same time. Once she's satisfied (or shortly before she's satisfied), BROKE, you can pull out, jack yourself to OI, then put your cock back inside her and blow that load or take the condom off and blow your load—with her consent, of course—all over her ass or tits or stomach or Toyota Corolla or whatever.
But for your partner to feel like this is your superpower and she totally lucked out when she met you, BROKE, you can't leave her in the dark about the way your dick works. If you don't let your partner know you need to stroke yourself a little right before you come, she's likely to interpret your staying power (your superpower) as a sign you aren't attracted to her.
Now here's how you might be able to fix this in the long run, BROKE: When you're masturbating, you should...well, you should do what you're doing. Masturbate while sitting up or lying on your back, use your hand and a little lube, but do it with a much lighter touch/grip and maybe invest in a quality (read: silicone) masturbation sleeve. Don't use the death grip—don't squeeze the life out of your dick—as that will make things worse. And while cutting back on porn and using your imagination instead is fine, the real goal is to re-train your cock to respond to subtler sensations. Which brings us to the hardest part: If you can't cum after masturbating for 10, 20 or 30 minutes—using that light touch/grip, a little lube and maybe that sleeve—you don't get to cum. No flipping over and humping the mattress after half an hour, and no using a firmer grip. You put your dick away and go to bed or work or school. Because this is about focusing on pleasurable sensations, not blowing your load, and you want to let the pressure build in your balls between sessions.
Stick to these rules when you're on your own for at least six months. If your dick is able to adapt, it will, and then you can take your more sensitive dick into partnered sex with more confidence. But if after six months you're still not able to cum using a lighter touch or a masturbation sleeve, you may have to accept that this—your need to get yourself to the point of OI during partnered sex—is the way your dick works. Just as some women need to use a vibrator in order to cum, and that doesn't mean they're broken, some men—after giving and receiving a lot of pleasurable fucking—need to pull out, jack to the point of OI and then plunge back in for the last few victory pumps. It doesn't mean they're broken, it doesn't mean their dicks are broken, and it certainly doesn't mean their sex lives are over. As sexual superpowers go, BROKE, it's a pretty decent one to have.
Finally: I just re-read a paper on traumatic masturbatory syndrome (TMS) that was published in the Journal of Sex & Marital Therapy back in 1998—which I think was before you were born (math is hard)—and it identified prone masturbation as the primary cause of delayed ejaculation. To prevent TMS, delayed ejaculation and other forms of erectile dysfunction that prone masturbation can lead to, the authors recommended "masturbatory instruction in the home, classroom or paediatric clinical setting."
Q I've been seeing a guy for two years. It was a FWB situation from the start, because he already had a girlfriend. I adore him, we quickly broke the rules (L-word spoken on both sides), but the B part has dwindled to nothing. We haven't had PIV sex since September, and he just added a second FWB to the mix. He swears he's attracted to me and says we aren't having sex—with the exception of me blowing him from time to time—because he's older. But I know for a fact the other two women are getting some. He says he's attracted to me—so why doesn't he want sex? How do I make him see how much I need him without issuing ultimatums? —Scared But Horny
A Your FWB might come through with a little PIV if you issued that ultimatum, SBH, but it sure doesn't sound like he's going to fuck you short of one. You might be able to get this guy to quite literally throw you a bone, but I think your time would be better spent finding a new FWB.