2 things. On some CD's and LP's, the level is different between tracks. Same would apply to MP3 or Flac or whatever format, especially between music from playlists where the source of the music is vastly different. Im not big into computers as a music source and I think there are programs that can equalize the levels, but not taking those into consideration, this could explain it.
Secondly, our brains get sensitized to a certian level and we can have a tendency to keep wanting to turn it up. I know you stated that you are noticing the effect without listening beforehand, but I dont quite understand that part of your question/observation. How would you notice it wasnt as "loud" if you didnt listen beforehand in order to have a reference?