I'm a glasses wearer, and I strongly recommend getting some contact lenses to skirmish in. I strongly recommend contacts to anyone unfortunate enough to need corrective eyewear though, it just makes you more... Actiony. Does me, at least.
Then there's the practicals: keeping spectacles on under solid eye-pro is multiplying the number of mistable surfaces that will up and ruin your experience; only select eye-protection will even fit over your glasses without interfering with them; should your specs get knocked off-kilter under your headwear, you'll have to disengage and find safety everytime you want to adjust your eyes, and taking off your eye-pro during a skirmish is not a good thing, even if you are huddled facedown in a corner all alone - you never know who's been out on the stealth, lost the frontlines and could rush up on you at any time blatting like a dick.
Having said that I know of a fair few players who - for one reason or another - do go out there in their glasses. Astigmatism can stop you wearing lenses and some guys can't afford or just plain don't like em.
In summation yes you can wear glasses in a skirmish (under normal face-pro) but I strongly recommend trying lenses, I know I couldn't operate the way I do without them.
As for gun transport... I always feel a bit sketchy when talking about concealing these things

But Ian's on the money, shorter guns or folding variants can comfortably fit in sports bags or rucksacks: when I'm en-route to a skirmish I just look like a guy in DPM trou with a huge bag, my bag carries my gun and my jacket - inside my jacket is just about everything else I need. Goes without saying but if moving your gun in a rucksack, make sure there's no bending or twisting force being exerted on your gun by the other things you've packed - turning up with a bent barrel, there'll be tears before bedtime!