There are some videos here and there in which ladies lose their clothes when they didn't want to (those ones in which they get wet or ruined in an accident or fight). The involuntary loss just feels so significant and embarrassing when the clothes belong to a properly demure lady, so nice and covering up so much.
What about a variety of more scenarios in which they lose clothes article by article, reluctantly or otherwise because they had to:
- Stripping as payment
You've caught the secretary in her office doing something that would get her in serious trouble (skimming money, selling company secrets, etc.). She pleads with you not to tell anyone and desperately offers to give you an item of her clothing in exchange.
Or a role reversal of A Visit to the Bank Manager. Demure client comes in and yes, she knows she's a little behind in her payment but can't she offer anything else of value? Any assets at all? What about an article of her finest clothing?
In both scenarios she keeps offering and stripping, one item at a time, until you are satisfied with her payment.
- Strip poker
She is bored and offers to play a game with you, with this deck of cards lying around. How about poker? But, what can we wager...?
Your own hand maybe doesn't need to be shown on camera because whatever it is, it's always better than hers, even when she flirts to try to distract you. The game could end when she announces she's not bored any more! Another option: demure girls play strip poker against each other.
- Stripping as punishment
High-ranking girl angrily scolds a lower-ranking girl (or perhaps girls), calling her a disgrace to the organization. Until she redeems herself around here, she is not fit to be dressed as a member of her profession. She is stripped down to her underwear, but her humiliation is only beginning - she is sent back to work, meaning everyone is going to see her. (Potential options for twist ending or sequel video: stripped girl sneaks back into the room and sneak attacks the higher-ranking girl, turning it into another fight scenario... or, the higher-ranking girl gets punished in turn for exceeding her authority).