I personally lean more toward what Johan suggests (1000 short time, 1500+ all night). I usually up these prices by 100 to 150 baht so that they have change for taxi, bus, or food.
Having said this, I think it also depends on your relationship with the boy. Even before I have lived here I had some "regulars". I could get by with only 500 baht when money was tight (earning a Thai salary, it is that way towards the end of every month now), The boys (they can probably be considered casual friends by now) would know that the next time I visit, even just for a drink, they'd get a slightly higher tip from me...guranteed. Or I would help them with a (non-monetary) problem such as needing a place to sleep for a night if they argued with their roommate. Most regulars in Thailand usually have at least one commercial friend like this.
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