I've pocket-carried a Model 640 .38 Special with Pachmayr Compac grips for over twelve years. I mostly wear shorts mid-spring through mid-fall and twill work pants the rest of the time; but when I wear my jeans (also Wranglers) I may carry OWB with a long shirt. I use a Desantis Nemesis or Uncle Mike's pocket holster, depending on which works better with the pocket du jour.
The 640, Pachmayrs and ammo and all, probably weighs around 24 ounces, but I have no trouble carrying it. I've done it so long I don't notice the weight unless I try to pack it in a jacket pocket.
I can't imagine ankle carry of anything but maybe a Kel-Tec P32 or P11 last-ditch, I'm-on-the-ground-already piece, because I have spinal arthritis and degenerative disk disease that would make bending to draw the gun, then straightening to use it, difficult and slow. Carrying a Charter Arms .44 that way is something I really can't imagine, even with a good holster rig.
"Don't let macho be your epitaph."