Rockrivr ~
Lots of possibilities there. I forgot to ask for a caliber preference, and I'm not sure what's on the list in MA, but for semi-autos, you might want to look at the following.
Kahr P9 or PM9 (9mm) -- small, thin guns. P9 somewhat lighter than PM9 and commensurately more recoil though still not bad. Long DA trigger pull, reasonable to excellent accuracy, plenty of holster availability. Very concealable. Drawback is that it might be too small for your hands, causing a little trouble with the long pull (if so, use a little less finger on the trigger and the trouble will go away).
Glock 26 or 27 -- the 26 is a 9mm, 27 is a .40 S&W. They're Glocks, with Glockish triggers (love 'em or hate 'em, they are what they are). Small, lightweight, but thick. Extreme reliability, extreme durability, very resistant humidity, sweat, and other ickies associated with constant carry. Lots of holster designs out there; don't ever carry one of these without a trigger-covering holster.
KelTec P3AT (.380) -- very, very, very concealable. Not necessarily fun to shoot (they bite me pretty bad, though I'm told they don't bite everyone), and the recoil can be surprisingly unpleasant. The sights are rudimentary but can be upgraded to merely bad. Not inaccurate, but difficult to shoot accurately. Not necessarily reliable out of the box, but easy to tune and KT's customer service is legendary. Might be too small for your hands. Super lightweight. Did I mention concealable?
CZ RAMI (9mm or .40) -- small, thick, heavy enough to absorb recoil but not too heavy to carry. DA/SA, no decocker, heavy trigger (15 lbs in DA, 9 or 10 in SA). Can be carried hammer down in DA, but it also has an external safety, so can be carried cocked & locked if you prefer. Fairly accurate for the size. There was a polymer-framed version at SHOT Show, but I'm not sure when that will be on the market. Definitely worth a look when it does, and until then the metal version is nifty. Ask Eric at HBE Leatherworks about a holster for this one.
HK P2000SK (9mm or .40) -- this is the smaller version of the P2000. Two great features: it's completely and totally ambidextrous, and though polymer framed, it allows you to alter the grip size to suit your hands by adding different panels to the grip. Excellent trigger in a DAO. Might be hard to find a holster since it's still fairly new on the market.
pax