So I found this macro and was using it to help me out while pickpocketing, however I found that if you spam it really fast, you can pickpocket the same mob 3 or 4 times (with the help of lag, ive looted over 8 times).
Notice how the looting is at the exact same time in the picture (20.55.00 hour/min/sec)
/console targetNearestDistance 5.000000
/cleartarget
/targetenemy
/cast pick pocket
/console targetNearestDistance 41.000000
/console targetNearestDistance 5.000000
/cleartarget
/targetenemy
/cast pick pocket
/console targetNearestDistance 41.000000
(yes I put it two time in the macro)