I'm pretty sure you do
not want to use a speaker amplifier with headphones. Even assuming you could turn it down far enough to not blow them up, there would probably be an impedance mismatch that would make the bass sound weird and you'd probably get a lot of noise because it's not designed for such low power transducers. 40 watts should fry even the sturdiest and power hungry headphones if you just once accidentally bumped the volume. If it has a headphone output designed for headphones, you could use that, but I'm not sure what sound quality you'd get though. I tried using my headphones (Senn HD800) straight from an audio jack of a good quality receiver unit once, and the sound quality was terrible, but I think that's because it wasn't meant to drive anything even slightly power-hungry.
I don't know a whole lot about switching units, but if you asked on head-fi.org, I bet someone would have an answer. If you're already happy with your sound quality from your computers, probably the simplest possible mechanical switch would be best (definitely avoid anything with a built in volume or "equalizer" feature unless it's really good equipment). I honestly think even a simple switch from radio shack or something like that would be good enough, as long as it doesn't mess with the signal with a volume control etc.
Some desktop amplifiers have multiple inputs I think, which would definitely be a good solution and simultaneous upgrade (although expensive). But then again if you upgrade to an amp you'll probably want to get a DAC, in which case you might as well just get a digital switch to your DAC/amp. An HD555 doesn't really
need a dac/amp though like some of the more crazy high end headphones do.
Here's an alternate super cheap idea: Buy two headphone jack extenders (or Y connectors and only use it for one headphone), and plug one into each of your computers. This way you won't wear out your computer's jack because you'll instead be wearing out the extender's jack. It will still slowly wear out the headphone jack, but sennheiser's headphone jacks are pretty sturdy. Not a switch, but maybe an alternate solution
