Edit: please send a PM don't post here
I have a few ideas in this direction neither of them are set in stone.
The partner in all of the scenarios could be female or a shemale
My character would be kind of curiuse about submission and a few other things but quiet inexperienced. Because of a job or something ells maybe school related he needs to get a doctors check up one of the things is a proctology exam, your character could either be the female doctor or a nurse. When he has a very strong reaction to the exam and feels very ashamed of cuming during it you keep his name or maybe you just got turned on by it your self (I think this is why a new doctor or nurse works best) and you have him come in from more examinations after you can be more ‘private’ it could have some blackmail and NC in it or be consensual but I would like to see a full relationship both could be fun with an older person if she is a doctor or somebody of almost his age if it’s a nurse. During the relationship she could guide him into becoming more of a ladyboy and a sub as well.
This is something along the same vain for my character but in this case you would take the roll of the school councilor. My character would be some what confused and shy about his emotions and come to her eventually telling her he liked putting on girls clothing maybe the councilor is secretly into things like that maybe she is a dom and the cute boy is just the type she likes. But instead of ‘talking him out of it’ she gets him deeper and deeper into her own world
For this would like a good age difference
This is straight forward enough, his sister walks in one him once while he is jerking off in girl underwear and from that moment on she uses him more and more as her little slave. Maybe she has her own apartment and she has him do chores there but I see it rapidly moving from that to a full ownership and domination. This would probably be the most Blackmail/NC one of the lot.