Tag Archives: Kelley May

In this comprehensive disciplinary saga, I, Miss Kelley May, guide my little Lilly Calloway through a journey of correction and redemption. This two-part video captures the full arc of Lilly’s …

Alex is having a hard time with her big sister Kelley going away to college. Who’s going to play silly games with her (like Duck Hunt)? Who’s she going to …

Don’s laziness has finally caught up with him. After ignoring Kelley’s requests to do his part of the household chores, he’s in for a rude awakening. When Kelley comes home …

Katie Jane and Kelley are friends in real life, and during a shoot decided to just film a scene without a plot that was just them playing and having fun. …

Miss Kelley is the office HR manager and is having to, once again, deal with the CEO’s spoiled brat of a step-son. Milo has lived a life of privilege without …

You come to Miss Kelley seeking discipline and accountability for your diet and exercise routine. Miss Kelley makes it clear she won’t discuss diet specifics, and this is a routine …

Another classic role play scene, the spoiled young, bratty trophy wife and her stern old fashioned husband. Really this was just because I had been to a school ball and …

It’s well-known among Kelley’s friends and roommates that she has a bad habit of not keeping her kitchen tidy. She even admits that sometimes her friends do the dishes for …

Raven is supposed to be finding a job and not just being lazy and laying around the house. But even after her first spanking from Auntie Kelley (and humiliating temperature …

So this plot came about completely by accident. We had just gone to lunch and I had ordered a very good bottle of which since of course we didn’t finish …