From the SRD:
SRD said:
A Bluff check is opposed by the target’s Sense Motive check.
So, I'd say your player is right. If you don't allow him a Sense Motive, what DC are you using?
In practice, I always roll dice if the player asks, even if there's no point to the roll. If they don't ask, I usually don't worry about checking to see whether they believe the barmaid really thinks they're cute or is just hunting for tips. If they are at a "plot point" conversation, I'll roll Bluff/Sense Motive for the general feeling the PC gets from the NPC.
Most of the time, I figure the PCs "want to believe" anyone they aren't explicit about Sensing (i.e. passive use) and apply the -5 modifier. On the other hand, if a PC is actively Sensing the NPC, I'll gauge the feedback on the results of the roll, giving more specifics about the deception for better rolls.
If you want advice on how to run your game, though, I'd say that Bluff and Sense Motive are the social analogs of Hide and Spot. If you'd give your players an automatic Spot against a Hiding NPC, then you should do likewise with Sensing a Bluff. Just depends on how much you like to roll the dice. The basic idea's the same, though.
As far as how often to roll, I'd say once per conversation. Modifiers are things like a long, meandering conversation that covers many topics; the PCs are actively suspicious of the NPC; the NPC says something the PCs know to be false; it's a "plot point"; etc. Really, the automatic check should just be something that tells the PCs, "Hey, you might want to be paying closer attension."