Smallest gun I pocket carry? Kahr PM40... it's the smallest gun I've ever pocket carried, and one of the most powerful as well (others having included the Taurus 650 .357 Magnum, S&W 442 .38 Special, S&W 638 .38 Special, Kel-Tec PF9 9mm and Glock 27 .40 S&W). Recoil is stout, but it's a fairly accurate little gun and I don't feel particularly underarmed with 6 rounds of .40 S&W.