I've jacked a few times in the past until the skin was chafed and I was VERY sore for days and couldn't touch it. Of course that only made it better later on when I had all that lust saved up.
As far as just generally being sore, though, even just one insanely intense orgasm can leave me sore for hours, and that happens at least probably once a month, if not more. I'll edge for a really long time over some amazing fantasy and then when I jack and cum, it just gushes and gushes and gushes, and when it's over I feel like I'm bruised deep inside my cock from the crushing internal spasms. ...Of course, the trouble is that those kind of orgasms tend to come during these occasional periods I get where for anywhere from a few days to a couple of weeks, for some reason I'm having the most amazing fantasies and wicked orgasms, so it's just one, there are several. And they're so good and so addictive that during those periods I usually jack as often as I possibly can, sometimes three or four times in one day, and I'll be in incredible pain just walking around. | 
