I started down this path with my girlfriend. First I sent a bunch of nudes to her dad and brother without her face from a anon social media account. Them I started trying to get her drunk and undressed her in front of the windows for the neighbors to see. Eventually I want to get her so drunk that I can have the old neighbor come over and fuck her. I'll show her pictures later and let it sink in
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That's great. She does have some siblings, it sounds really hot to send her brothers her nudes. Or to send them to our friends.
Getting her drunk and stripping her sounds like a good way to make her feel humiliated.

I want to wait until I know her fam has been cumming to her and then show them her face in one of the nudes. Get her drunk when they are over at the house and leave them alone with her. I think it would break her to know that her dad or brother fucked her cause there's not much she could do about it