I'm a 37-year-old straight female dating a 45-year-old straight man for 3 months. Only man over 40 I have been with. He is unable to orgasm from anything but his own hand and it takes him FOREVER! Nothing I do works. I have done oral until my jaw locks up and we have tried every position in the books — and every sex toy. Cock rings that vibrate, porn, lube you name it. He agreed to not masturbate for two weeks and we did not have sex for that long but it does not matter. He even stopped self-pleasuring completely. Still: the only way he can reach orgasm is kneeling over me masturbating while I tickle his balls very lightly with my nails — and let me tell you, if I deviate at all from his instructions it's done! Sometimes he can't even reach orgasm then it's taking too long he gives up. He says it feels like it's right there but just can't.

He is not on any medications and just was at the doctor and is healthy. He remains hard — that is not an issue. He was divorced and prior to me has not been in a relationship for 8 years. He's had sex but mostly meaningless. He says he's orgasmed from intercourse and oral before but not in five or so years. I guess he's been self pleasuring and forgot how? He seems very attracted to me and wants to do it all the time. He is attentive and makes sure I'm satisfied but I'm not. I want him to orgasm from me. I'm raw from it lasting too long and I don't enjoy him jacking off on top of me all the time. I find myself just wanting it to be over and getting annoyed. I'd like to enjoy a morning "quickie," and I'd also like the possibility of maybe becoming pregnant if the relationship progresses to marriage, something that would be naturally impossible at this rate. We have open communication but it's not helping. I suggested prostate massage he said no. He's a great guy otherwise but long term I will not be sexually satisfied. I've tried to be understanding and I was for the first two months. I thought he would adjust or get used to me, but nothing has changed. Can it be fixed? Is this his age?

Handless In D.C.

My advice for dudes with your boyfriend's problem hasn't changed much since this 2003 column. Just swap out "death grip" for "kneeling over the girlfriend and masturbating while she tickles my balls" as you read along, HIDC:

You'll have to swear off the death grip forever, ABF, if you want your dick to respond to more subtle sensations. When you jerk off, use a light touch and let it take as long as necessary — and it may take a while. When you're with a woman, fuck her brains out and give her orgasms galore, and when it's time for you to come — the moment you're used to taking matters into your own hands and finishing yourself off with the death grip — force yourself to use her body or her mouth or her pussy, or, if you must use your own hand, use that same light touch you've been practicing with when you beat off. If you don't come, well, tough shit, you don't get to come. To avoid giving the women you're with complexes, warn them in advance that you're trying to retrain your dick. While this approach may be frustrating in the short run, in the long run only this approach — a light touch, a firm resolve, and consistent denial — will kick your dick's dormant nerve endings into gear.

With some mild tweaks and resolute adherence, HIDC, following the advice above could help your boyfriend retrain his cock. But if you give it try and it doesn't help — and I'm talking months of trying, not two weeks of trying; and no resorting to "what works " during those months, i.e. he doesn't get to come if he can't come in a reasonable amount of time from vaginal, oral, or whatever else you're up to — then you'll have to heed the rest of the advice I gave that guy suffering from death grip syndrome way, way back in 2003...

Your problem may not be fixable, ABF, because your dick, after 30 years of abuse, may be too far gone. If that's the case, you may have to accept your fate, adjust, and deal. Fuck your girlfriends until they're satisfied, then pull out, use the death grip, and when you've reached the point of no return, stuff it back in her. If your girlfriends complain or develop complexes, ABF, you can accuse them of enforcing a sexist double standard. There are lots of women out there who can't come from vaginal intercourse alone. Most women, in fact, require more intense, focused stimulation — oral, fingers, vibrators — in order to get off. And according to my dog-eared copy of Sex Advice Columns: Standards and Practices, I'm supposed to come down like 10 tons of shit on men who make these women feel guilty about needing more stimulation than dicks alone can provide. It seems to me that if women who require the female equivalent of the death grip (say, a Hitachi Magic Wand) aren't supposed to feel bad, then men like you, ABF, shouldn't have to feel bad either.

In answer to your questions, HIDC: it's unlikely to be age; it might be a deep groove he carved into himself over the last eight years and you might be able to help him carve a new groove; or it might just be... how this dude's dick works. And there are worse things to have in your life and your bed than a guy with a hard cock who can go forever. If you can let go of your ego-y need to see him "orgasm from" your efforts alone — just like guys with girlfriends who need vibrators to get off are encouraged to let go of their ego-y needs — you can enjoy the hell out of his dick, and enjoy his ability to get you off and off and off, before shifting into the position that works for him and the activity (JO, ball tickling) that gets him off.

As for your hope of one day getting pregnant naturally, HIDC, the advice I gave guys with death grip syndrome at the end of this piece at Vice more than applies:

"Fuck and fuck and fuck, and then jack it, and then shove it back in when you reach that point of no return."