The only person that can make sex for him worthwhile is - himself. Whether as a partner in sex or in life, it is not your obligation to try to figure out someone else's problems and fix them. Not being able to cum with another person indicates that he has a physical and/or psychological barrier to reaching orgasm - often referred to as Delayed Ejaculation - and it is up to him to have the willingness to deal with it head on.
With that said, it is commendable that you care for him enough to want to assist him with this problem - and there are things you can do to help him along the way. Primarily, keep a positive attitude. The more demands you put on him ejaculating in front of you, the more pressure it puts on him mentally. Pushing him will only make him feel discouraged and embarrassed, and will lead him avoid the topic and withdraw even more into himself. Communicating about the problem removes the shame behind it and makes the mention of the topic less of a trigger.
In addition to the techniques mentioned in other posts (see below), here are some other suggestions:
Discuss the fantasies that really turn each of you on, as well as anything else that sends him over the edge. Maybe he is only into the run of the mill stuff, but if he has any preferences or responds well to certain words or (perhaps) Dirty Talk, it'll be all the ammo you need to help him go all the way.
Suggest that he abstain from masturbation so as to build up sexual tension to use on you. It could be that he's become too reliant on jerking off for sexual release and feels most comfortable that way. Cutting himself off for a day or two might be all that he needs.
Learn the 'right strokes' from our article on Handjob Techniques, bring along plenty - and we mean puh-lenty - of Lubricant, and work him until one of you is through. Ask him what he likes to picture during a masturbation session and use that to your advantage. Alternatively, why not get off together with Mutual Masturbation? That way, you can take mental notes on how he likes to be stroked, and also work your way up to coming through sex in steps.
If you're willing to stay, you have to be willing to work with him. But remember, your role is to be supportive and encouraging without making it seem like you're feeling sorry for him. Once some time has passed, it may turn out that you aren't sexually compatible - but in the end, you'll have gained valuable experience in dealing with issues of a sexual and/or psychological nature with such a positive approach.
For additional advice related to this topic, check out 'I love sex but can't cum' for ideas to unlock orgasm potential, and 'I can't cum with my girlfriend' for a discussion about delayed ejaculation and techniques to overcome it.
Posted: 17 Aug 19:16