it all depends on load. Both Mack truck and Honda Civic can cruise at 50mph, but the load is what makes it different.Yes, if you connect a 100dB sensitivity speaker to the 100 Watts amplifier and a 86dB sensitivity speaker to the 250 Watts amplifier, the 100dB speaker will sounds much louder!
if the gain of both amplifier are identical and connect to a pair of identical speakers, the required output power of both amplifier is less than 100 watts to provide that degree of loudness (volume), the output volume of both speaker should be same.
BTW, a 250 Watts amplifier can’t provide 2.5 times louder volume than a 100 Watts. The difference of both amplifier output is about 4dB.
According to psycho-acousticians that a level 10 dB greater usually means "double the loudness" or "twice as loud". In this case, you need 1000 Watts to get twice as loud!
If I would connect a right channel output of a preamp to a 100 Watts monoblock and its right-channel to a 250 Watts one then the right speaker will be 2.5 times louder than the left one.