Bob has been caught stealing the girls plimsolls as they get changed after gym class and masturbating into his own. The gym teacher has had enough and finally sends him to the Headmistress Miss Ruby for some severe discipline. She decides he clearly needs to like his plimsolls a little less and bends him over the desk to give him a merciless slippering with all the plimsolls he's been caught with. Scolding him the entire time he is thoroughly disciplined hard. Eventually his shorts are cut off him and he's given his mandatory 6 of the best from Miss Ruby's crooked bamboo cane. This was bob'...

Bob has been caught stealing the girls plimsolls as they get changed after gym class and masturbating into his own. The gym teacher has had enough and finally sends him to the Headmistress Miss Ruby for some severe discipline. She decides he clearly needs to like his plimsolls a little less and bends him over the desk to give him a merciless slippering with all the plimsolls he's been caught with. Scolding him the entire time he is thoroughly disciplined hard. Eventually his shorts are cut off him and he's given his mandatory 6 of the best from Miss Ruby's crooked bamboo cane. This was bob's first 6 of the best from Me and he struggled to take his discipline but he managed to complete the set. This is filmed in a school room setting, lots of corner time, scolding, and Miss Ruby is in full teachers gown. Bob receives a hard slippering with all his dirty plimsolls and I train him like Pavlov's pet, conditioned to associate pain and discomfort and shame with his plimsolls instead of these perverted fantasies running through his mind . Let's hope he thinks twice

Follow bob's perverted escapades in the rest of this series:

Tied Down & Severely Slippered