Where does compression come into the conversation?
Gapless is just that - no gaps, as ripped from the original CD. If there are fade outs and silences in the original rip then there will be fade outs and silences on playback with gapless playback, just as there were on the original CD.
If those silences are being shortened on playback then some kind of processing algorhythm is being applied, and its effects are, in my opinion, undesirable.
My last mobile phone wouldn't support gapless playback, and it was annoying that there were silences between tracks on something like Deep Purple's "Made In Japan", because the tracks were intentionally segued one into another (and not by me).
And this was despite installing a media player (WinAmp) which claimed to give gapless playback.
My current mobile phone has the same media player installed (WinAmp), and this time around there are no gaps in the segues, just as if I were playing the CD, and this is an altogether better situation from my perspective.
With both devices the media player the came installed on the device was incapable of playing the tracks without a dropout in sound, something which irritated me immensely.
If your media player is removing gaps then your settings might be set for crossfading, removing detected silences, or something along those lines, then it's likely to be DSP driven, and anything like that is unnecessary and undesirable.