God man, you gave me so many ideas with your own ideas.
Rape the daughter so loudly her parents wake up and kill you.
While you shoud have thought about that dumbass.
For those uneasy with the rape setting: A strict (christian like) boarding school for girls only.
It's a manor or something like that in border of a small town ; the late middle-age (near Renaissance) kind of manor, with many dependencies and all.
You're a boy from the small town.
At day you flirt with the girls when they come in town ; be careful of their chaperone.
At night, you go to your rendez-vous with them and have to sneak your way to the right bedroom.
Perhaps there's more than one girl by room. This can possibly open the gate to threesome if you seduced the two girls, but it will last longer and there will be two girls making noise, so greater risk to be caught ; what will you choose, the joy of the threesome, or the security of classic one on one ?
Or you'll need to wake the girl, then lead her to a place where you'll be able to have sex ; a stealth escort mission, who don't like that...
Possible bonus (for those who like that):
One of the supervisor catch you.
Positive point, when she's on duty she'll not report you, so you can make more noise (still be careful the other girls on the floor would be suspicious).
Negative point, she's the dominant kind or futa, you've to pay her silence with your body. And the more you made noise, the more she'll be selfish ; once again a hard choice, find the right balance to enjoy both your time with the girl and your time with the supervisor.
Possible plot twist:
Each week, you found an envelop at your name with money inside. The amount seem to change depending of the number of girls you had sex with.
Someone of importance at the school (why not the dean) want the girls to not be too sheltered. Many men would want a well educated girl with good manners, but few would have the patience to deal with a sexually naive and clueless girl. Worse, those who would have the patience could take advantage of this naivety and corrupt them into sex slavery.
So, this important person at the school is very happy by your doing, you teach the girls what the school isn't authorized to teach them.
Once you've understood this, it can possibly lead to challenges:
Achieve to make the very shy girl show you her naked body before the end of the week, and you'll have a bonus.
Continue until you've sex with her, a bonus for each step you make.
A good wife should help her husband to succeed by any possible means ; XXX is the smartest one, and she come from a really powerful family. She'll surely marry an man of influence... Open her to the joy of anal sex, it will avoid risk of pregnancy in her future dedication for her future husband career.
XXX grades are lowering. Penalty if you've sex with her before her grades return to a good level. When she'll ask, tell her clearly that you learned about her grades and don't want to hangout with an brainless girl.