Ann and Ms. Shego giving Kim a... hard time at the parent teacher conference (Phillip-the-2 & Gagala)
Drakken giving Shego a creampie; having a hot sidekick is one of the main benefits of being a supervillain (Nyuunz)
Play strip poker against Kim and Shego in Strip Poker Night at the Inventory! (link in comments)
When Ann needed some relief, thankfully one of the twins stepped up to the plate (Phillip-the-2 & Incognitymous)