Since everyone is recommending S&W 38's then I will throw out Taurus revolvers. I have a Taurus 851 and couldn't be happier with it! The price should be right up your alley on these. I think Buds has them for a little over 200 which is about 100 bucks cheaper then its S&W counterpart.
On size,well thats up to personal preference.I carried a KelTec p32 there for a while and was happy with it.Its not that much smaller then the 380 but has better penetration which is the biggest problem with the 380.You would want to load both the 32,and 380 with FMJ for over penetration is not a concern with those.
Actually(I thought this was funny myself) Towerclimber shot my p32 one day,and after just one mag,he decided he must have one so he went inside and bought the last one that Carters had.
I also believe he said that was the first and only plastic gun he would ever buy