You know it’s going to be a cruel belt spanking when it takes two men to hold the girl in position, and they don’t even feel the need to take down her pajamas for it:
But the cruelest part of all? It’s the part where she doesn’t get any help putting lotion on her muchly-welted bottom, so she has to do it herself. Poor girl!
(Don’t worry; eventually she recruits a friend to help her…)
Pictures are from Girls Boarding School.