Coming? Or going?

I've given my boyfriend head 3 times now without him ever reaching orgasm. The last time I went down on him, we went at it for an hour and a half before I got too tired to continue. He says that he gets very close every time I try, and that it always feels really good, but he still has yet to orgasm. He's 19, very fit and healthy, and he's had an orgasm before without problem. Is this a problem with me? Or could he have some health issue? Is there anything I personally can do to make it easier for him to come when I give him head?
Jhames replies:

He gets close every time you try.

I interpret that as you are using various techniques that he really enjoys, but then maybe you opt for a different technique or vary its pace. These changes can quickly take a guy from the verge of reaching an orgasm to simply enjoying the sensation. Of all the techniques you are using for an hour and a half, at least one had to do the trick of bringing him close to orgasm.

So how do you find out what's working?

Ask your boyfriend what he enjoys most when you give him head.

You can ask him before, during or after sex, and you can talk without sounding clinical or cold. "You like it when I [insert technique here] to your [head/shaft/balls]?" Converse with a bit of dirty talk and you can achieve results without exhausting yourself, acting submissive (nobody needs to be anyone's bitch) (unless you're into role play which is a totally different conversation) or turning sex into mechanics.

Don't make an orgasm the expected result of giving him head. You could be doing everything right but your boyfriend could be under stress or thinking about anything but sex: this happens more than people care to admit. As well, not everyone will reach orgasm with oral sex: like anything else, no one activity does the trick for everyone. It can be frustrating for a partner to not reach orgasm, so take away the stress of having to come. Just have fun.

Unsolicited advice: if you're giving him an hour and a half of head, he can spend some time saying getting acquainted with your lower anatomy.

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