House Boys are subject to a variety of punishments ranging from Level Zero (non-contact punishments like writing sentences or giving a verbal apology) to Level Four (immediate dismissal, whether naked or not). Most punishments are from Level One to Level Three and are administered by spanking, and the most common spanking is over the Master’s knee.

An alternate method of administering Level One (bare hand) or Level Two spankings (with an implement) is shown above. The ‘Over The Pillow’ spanking is unrestrained and usually administered on the boy’s bed, though it can be carried out elsewhere. The boy is always naked for this discipline, though socks need not be removed at Master’s discretion. Since the House Boy has no right to physical privacy at any time, discipline must be carried out regardless of who may be present and could observe. 

The protocol calls for the boy to kneel on the bed and lean forward over pillows that are placed to ensure that his buttocks are raised higher than any other part of his body, with the boy’s penis and testicles fully visible from behind. The boy’s hands should be placed forward of his head with fingers interlocking or holding onto the mattress edge or the bed itself. If the boy fails to properly position his penis and testicles, the Master or a volunteer will gently reach under the boy and position them for him, and two additional swats will be assessed for the boy’s failure to follow protocol. Spanking itself will be conducted only by the Master, and careful aim will be taken to ensure that the buttocks are spanked while the testicles are not. Master will call out each swat by number and notify the boy when spanking has ended and the boy can begin his Corner Time (See ‘Corner Time’ rule).

Responsible and obedient House Boys should never receive a punishment of this type, and many boys have served here without receiving so much as a single swat for misbehavior. These are the compliant and obedient ‘good boys’ with a need to please, and Master values them highly. But House Boys who lack self-control or suffer from inner brattiness will become familiar with this type of discipline. The boy’s actions determine whether punishment 'Over The Pillow’ is merely a page in the rule book for guests to laugh about or a reality for them to observe.