Between Thanksgiving and Christmas weeks in alternating years, Master hosts a ‘Naughty Or Nice’ Party for friends and family. This is one of the few events where Master’s Kinky Friends and his more ‘vanilla’ friends mingle and socialize. For this event, this first few hours are your basic cocktail party, and the House Boy is responsible for the preparation and serving of snacks and liquid refreshments, as well as making guests comfortable. The pool and jacuzzi are closed and off-limits.

Later in the evening, the jacuzzi area is opened and available for use by all guests during the transition time from the ‘Nice’ portion of the event into the beginning of the 'Naughty’ hours. The jacuzzi is the only place in Master’s home where clothing is not permitted even for visitors, and the 'vanilla’ guests tend to say goodnight and excuse themselves.

During the final hours, the Christmas Party continues as a 'Naughty’ Event, with Clothing Optional throughout the house, except for the House Boy who is required to remain naked. The pool remains closed. Among the games and activities scheduled is the annual House Boy Evaluation to determine whether he was 'Naughty’ or 'Nice’ in the previous 12 months. Master will have calculated the number of days that the boy went without a spanking against the number of days where he was spanked, to determine a verdict of 'Naughty’ or 'Nice’.

If the boy is judged to have been 'Nice’, he is permitted to fully participate in the remainder of the evening as a free person, with all the rights and privileges that go with it, including the ability to consensually physically interact with guests, and attend the 'Adult After Party’ which sometimes continues until dawn.

If the boy was judged to have been 'Naughty’, Master (posing as Santa Claus) will instead begin the punishment phase by placing the Naked House Boy over his knees and administering ten swats on the boy’s bare behind. Santa then offers his beard to any houseguest who wishes to continue the discipline – ten swats at a time – until one swat has been issued for every day that the House Boy was spanked in the previous 12 months. Swats may be bare hand or with the aid of a ruler, which is kept for this purpose.

A House Boy who is issued swats will be assigned Corner Time following discipline, then physically inspected and sent to bed naked without covers. Showering is optional. He is permitted to sleep on his stomach if he so chooses, and the Hug Rule remains in effect. If a visiting Master brings along another boy or sub, the bed may need to be shared.

During alternating years where Master does not host a Naughty Or Nice Party, the boy will usually accompany Master to a holiday party elsewhere.