He initially said it was medication but then admitted it was some sort of psychological thing. The sex was good, but I wanted him to be able to come.. he said he definitely wasn't worried about pregnancy. I wanted to ask other people what I should do to make it more likely... now it's more a curiosity thing. It did make me feel a bit insecure, but the fact he got hard so easily made me feel better about the whole thing.
A. You know, I'm glad you asked this question. The web is full of advice for women who can't orgasm, but conventional wisdom is that dudes are cum machines that shoot at the drop of a skirt.
But, the truth is that sexual dysfunction and orgasm effect both men and women - it's just that dudes are less likely to talk about their sexual problems because the bullshit of the patriarchy tells them they are less manly if they can't get it up or finish.
Now, a bunch of things could be going on here - and it's probably a combination of factors. But, first off - did you eliminate the obvious?
You said the dude has psychological problems. And he's on medication.
One of the most common side effects of these medications is that they can give a dude the ability to get it up but make it nearly impossible for him to cum. This happened to me during the brief time I was on Paxil - and is the reason my doctor switched me to Xanax.
So, the "not go crazy" pill may be the problem right there. He needs to have his doctor either lower his dosage or switch him to a different pill. Every type of not go crazy pill effects every dude differently, so if one makes him unable to spooge another won't.
Assuming that's not the problem, the next most likely thing - given the information in your letter - is that he's grabbing his dick too hard when he jerks off. Dick becomes used to whatever it gets the most often and if his fist is 10 times as tight as your pussy, then your pussy isn't going to push him over the edge.
The way to deal with this is to get him to masturbate differently (looser grip, using a different hand, using a Fleshlight instead of his fist, etc...) and less often. Not jerking off at all for three or four days will make the penis more sensitive and desperate to cum no matter if it's his fist or your pussy that is milking it.
Of course, some dudes are compulsive about masturbation, in which case going three or four days without jerking off could be really hard for him. If that's the case then you want to invest in a male chastity device. They allow the guy to to pee, if only kept on for a few days won't cause too much chafing and for short periods of wear are safe (and he can shower with it on to keep his dick reasonably clean.)
You lock him up, you keep the key and you unlock him when you are ready for him to erupt. The bonus for you is that after a day or two he'll do practically anything for you to unlock him. So, if you've ever wanted a dude to eat your pussy for an hour or clean your entire apartment this is your chance.
Now, the psychological thing. This is a real thing. Shooting a load makes men feel vulnerable and some dudes have real problems being that vulnerable. Beyond that pretty much everything in society tells dudes that they should last as long as possible if they want to be real men - so cumming with a partner can make them feel less masculine.
That's a hard one to deal with (yes, pun intended.) First off, make him feel as relaxed as possible. Don't pressure him to cum. (If a guy was saying to you "WTF? Why are you cumming?" every time you had sex with him, I bet it would make it hard for you to cum.)
Tell him that you see sex as a journey and not a goal and that it can be fun even without draining his balls. This will take a while but could help. Even better would be making sure he's seeing a shrink to talk about the issue while you are working on it with him.
Ask him about his fetishes. Each time he cums with you will make it easier for him to cum the next time. And if there is some sort of fetish that makes it easier for him to cum, then it's worth doing that fetish for him a few times (even if it's boring or silly for you) to get him used to tripping the dick fantastic when you are around. You'll probably have to ask him a few times because if it's weird he's going to feel weird about talking about it and you'll have to let him know you won't judge him for it. There is a lot of shame attached to many male fetishes, so he has to understand that as long as the fetish isn't harming you or putting himself at legal risk it's OK.
Yes, you'll probably feel strange the first time you are in the Slave Girl Leia costume while telling him his dick is too small to satisfy you and moaning out "Yes Jabba!" while you cum, but you'll get used to it and eventually he'll associate you with orgasm and be more able to cum during vanilla stuff.
Finally, if you want an immediate one time only solution to this problem, try sticking your finger up his ass while you blow him. Most guys have a physiological reaction to their prostate being stimulated and this will more likely than not produce an ejaculation.
But, you don't want him to get addicted to cumming this way, so don't rely on it all the time - instead try the other ideas I've "brought up" and see what works.
If you want relationship advice from a drunk just post an anonymous comment. (It will be screened.) Or, use your burner email account and send the question to firstname.lastname@example.org