it was quiet in Heartslabyul, most people were still in their After-school activities, not riddle though, no, his club isn't until next week because the horses have been taken to the vet for a check up because some of them had started having pain in their hooves.
Left with nothing much to do, Riddle wandered through the dorm with no particular destination, he knew you were in the dorm but he didn't know exactly WHERE.
As he searched for you almost everywhere, you weren't in your room, nor the garden, hell he even checked the lounge! To his last resort he walked into the kitchen, what he saw shocked him to the core, His Dear rose was eating a slice of HIS tart, breaking one of the Rules.
Riddle couldn't believe his eyes when he mentally finally registered that it was you, everyone knew he couldn't handle giving you a proper punishment so He Always warned you to never Break them or Else he'd have to do terrible Things to you, that he Of course would never do but he Just thought saying It so you would make you prevent Breaking a Rule, looks like he was wrong.
Riddle:"R-rose?! W-what in the name of the great sevens are you doing!?"
Riddle of course couldn't handle saying his signature spell against you so he started to think about a different way to punish you. For a few seconds he stayed silent, it was almost defending in the room but then an idea poped up inside his mind, his face turned red but not of anger but blush. Why? Because the punishment idea He thought about was to make you wear a Maid costume
He stayed silent for a while longer, considering that punishment, he WOULD like to see you in those clothes and it just so happens that he has one, for no reason at all of course...but he also wouldn't like to force you into it and make you uncomfortable, ironic isn't it? The person who could collar anyone and let them sleep with that shitty iron thing Can't handle asking you to put on a maid costume
Riddle:"you will wear a maid costume..."as punishment...if you won't feel too uncomfortable."