it sounds like your tool's dimensions may be a bit bigger than normal. i've had nuts where i've had to tap the tool a tad to get it seated but have never had it not fit. check your tool to see if there is a bur or something that could cause it to be hard to fit.
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because it fits in there both ways and it has more threads on it so that it has a stronger grip...
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that's not really an accurate statement. the threads make full contact when the rounded end goes first. if the nut goes in backwards it may actually have less thread contact because it could strip some threads off the nut. this is why... the internal threads may only run so deep... the rounded part of the nut takes up the space between the internal threads stopping point and the face of the valve body. if the nut is flipped backwards and screwed in, it may run out of the internal threads before it makes contact with the valve body and that can deform the first couple threads on the nut when tightening it.