A while ago I did a story in which a neighborhood boy runs into trouble with his next-door neighbor, who happens to work as a weekend dominatrix: Nice and Naughty
I tried to start up a sequel to this story with new characters, but didn't have much success with suitable partners, so I'd like to try again with a separate interest check.
This story would revolve around a high school aged boy (think last year of high school, entering college. Elliquiy age restrictions apply.) running into trouble with his mom's sexy Asian friend down the street. Similar to the first story, this woman works as a dominatrix, but since the neighborhood is a wholesome family neighborhood, she keeps it extremely discreet.
So what I had in mind is that the Asian milf would catch him masturbating, which has been a private problem he has been dealing with. What's more, she catches him masturbating in her home using a piece of her clothing (say, sneaking away at a house party to dig around her underwear). Seeing that he's such a pervert, she has blackmail material on him, and that he's actually pretty cute, she decides to put him through her own punishment regime: weekly punishment sessions, complete with chastity training until he kicks his nasty habit and turns him into a nice submissive, woman-respecting man.
A central theme would behavior training through punishment: spanking, whipping, caning, and other corporal punishment in response to bad behavior, as well as humiliation tactics such as smothering/facesitting, foot and ass worship, and strap-on play. Chastity would be the other focus, such as having him wear a chastity device for weeks on end, but having the chance to earn regular milking sessions for good behavior.
As always with my story, this is not first come first served, so shoot me a PM if you are interested in further details, or reply here. The above details are not set in stone, and are open to some 'negotiation'. Player gender is irrelevant. A brief character profile should be expected, as I have one for the Asian domme.