I started real pocket carry with a Kahr PM45. Then... added a PM9 for those occasions when I really had to go light. These days, its a Charter Boomer .44Special, or a SCCY CPX2.
It might sound like I'm all over the place with choice, but here's my thinking. I prefer a bigger hole maker, and insist on double action for safety sake. The Kahr 45 did the trick. It has a long medium heavy pull (but glass smooth). The Kahr 9 was good to go too. But... I tried the Charter, and _for me_ it draws better out of my pocket. Trigger is heavy, but 1000's of dry firings have smoothed it. I don't mind heavy. That little gun works well, and I shoot it almost every trip to the range. The bobbed hammer has been replaced with the one from the .45 Pitbull. I bobbed that hammer to make it more like the old Mag-Na-Port Backpacker. Its a little taller, and the rounded edge of that hammer makes the gun seem to glide outta my pocket. I bought the SCCY as an alternative to the Kahr, due to the larger capacity magazine. You hear all sorts of stories, but mine shoots perfectly well, and has never had so much as a hiccup. SCCY did replace my magazine springs for free when it was new to fix the hold open issue many had. Mine didn't have the issue, but they did it anyway.
I'd say most days, most times, its the .44 Boomer. It draws the best. And... I'm shootin' .44 Russians in it. Yah, I'm nuts.