I am not a big pocket carry fan, though for a while I envisioned that becoming my main way to carry. I don't live in a carry state so I will never really get used to carrying, and I do have a UT non-res permit so I carry where I can legally carry on that. So, I figured the more deeply concealed it is the better since otherwise I'd feel pretty conspicuous. Well, I carry a lot in my pockets (wallet in front pocket due to a bad back, keys, phone, Kleenex, medications, knife, etc.), I'm not a woman so I don't carry a purse, so I need my pockets. It really didn't take me long to get used to IWB as my main method of carry.
All that said, I have or have had several pocket guns and slightly larger but pocketable guns (autos and revolvers).
Currently own:
-Ruger LCP
-Kel Tec Pf-9
-SIG P290RS
-S&W 442
-Taurus 85CH
-2" Rossi 461
Used to own:
-NAA Guardian .32ACP
-Taurus 605
Have shot often:
-Kahr PM9 (best friend used to own one)
-Kahr MK9 (best friend used to own one)
-Kel Tec P11 (used to rent one often)
Shot occasionally:
-Kel Tec P32 (a range buddy let me shoot his)
-Beretta 950 Jetfire (a buddy had one less than a year)
Out of those I used to own, I don't regret selling them so that should say something. Out of those I currently own, I only plan to keep the P290RS and maybe the Taurus 85. The 461 is quite unpleasant when shooting magnum, the PF-9 shooting 9mm and 442 shooting +P aren't much better. The LCP's sights leave much to be desired.
Out of those I didn't own but have shot, all were fun in their own ways. The ones I like best are the two Kahrs.
I love my P290RS and don't see ever getting rid of it. I would love an MK9 as well. Either will do for occasional pocket carry, though for regular and extended pocket carry both are a bit heavy. For a true pocket gun, the Kahr PM9 is my favorite of the bunch.