His First Proper Caning

6 x 6 of the best for bob:   the trials and tribulations of bob the plimsoll pervert continue, having received an extremely severe beating with his own dirty plimsolls from the headmistress he remains tied down and feeling very sorry for himself. the headmistress miss ruby has pulled his shorts back up and left him to think about his actions. but she returns and looks even meaner with a strict reformatory kooboo cane in her hands. this young man got off lightly last time with a gentle 6 of the best. this time she's not going to be so kind, especially as he's back in her office after just 1 week. so bob is told he will receive 6 x 6 of the best. 36 strokes given with increasing intensity. poor bob shouts his head off but no one is coming to his rescue. instead miss ruby just pulls his shorts down and carries on. he tries desperately to wriggle away but to no avail. finally bob has received his full 6 sets, miss ruby reminds him what will happen if she sees him again and humiliates him further by rubbing his face in his dirty plimsolls.    as always miss ruby is using a lovely quality control cane and is dressed in exquisite wolford neons in gobi tan, with alexander mcqueen soft brown leather boots up to her knees, a pleated skirt and stunning pussy bow blouse.   filmed in full 4k and exported in hd with front facing camera shots in hd edited in.    follow the earlier exploits of bob here: his first clip: punishing the plimsoll pervert and the precursor to this clip: tied down & severely slippered