If the files you're playing weren't encoded gaplessly (eg. mp3's created with LAME Enc 3.9x, or .ogg or .flac formats which have native gapless support), then you could try checkmarking 'Remove silence at beginning/end of tracks' in:
DirectSound Output > config > Other tab.
The default CutOff value of -40dB should suffice...
Higher values (ie. moving slider to the left, towards the max of -25dB) will cause quiet portions at the beginning & end to be cut off, so don't go any higher than -35dB.
Some other people might recommend enabling crossfading (fade on start & end of song) in the Fading tab, but I wouldn't (at least not if you want the full tracks to play without overlapping or fading in/out).