I'm 6'3" - 290 lbs. I usually pocket carry my Taurus 605 (2" .357) in a cheap Uncle Mike's pocket holster, but since I bought my SA XD9 4", and a Don Hume leather IWB holster, I have been trying that out. It's not working out like I had planned, though.. may have to continue carrying the wheel-gun until the colder weather sets in, so I can have more options in where the XD9 is holstered on my waist band.
Pocket carry can be annoying at first (have to move all your stuff into ONE pocket), but I got used to it in a way. It doesn't work too well in my work jeans though; the pockets are too shallow. Works GREAT in my loose cargo shorts, though, and I don't mean baggy shorts either.
..but I guess the .380 would be your only option for pocket carry; as for your bigger calibered auto - LET ME KNOW WHEN YOU FIGURE IT OUT! I'm in the same boat.