I have a few that fall into a couple different categories. There's ones that turn me on to think about but I wouldn't want to actually have happen IRL, ones that would never really happen but I'd like them to, and ones that I'd like to do, and aren't out of the realm of possibility, but still need to get her a little more comfortable with the idea before they'll happen.
In the first category, something about the thought of all of the pictures and videos I have of her being shown to/ sent to/ stumbled upon by the men in her life, past and present, who would be the absolute LAST people that she'd ever want to have see them. Uncles, cousins, in laws, husbands/ boyfriends of her friends, friends of mine, old classmates, roommates, coworkers, exes, and so on. The more she dislikes them the hotter it is to me. If it started with non identifying pics and piqued their interest, after they'd had a fap or two over the anonymous stuff, then dropped the big ones. I don't know if it's the thought of their shock and (depending on who it is) dismay or enjoyment that I like, or that they might not tell her, or maybe she does find out and can't do anything about it. But I'd never want that one to truly come to fruition.
Second category, is for her to be a cuckquean and either she'd arrange willingly, or reluctantly be made to watch me fuck her sister and all of her female friends and family members. Not all at once, maybe two or three together at times, but over multiple sessions. In return I'd have her in a sort of one way glory hole, where she can see via camera and screen who she's fucking/ sucking, but they don't know who she is. And maybe vice versa at different times as well. And there's the always popular threesome with her and her sister, or cousins.
Lastly, I've brought up the idea of trying out swinging/ swapping. She's not completely against it, but not on fully board with it yet. I'd love to get her into it, I'd even be into hot wifing, and watching and filming a couple studs fuck her until she's in another dimension. I'd also like to get her into some really public sex, we've done the hotel balcony above a busy street, and some blinds open in the hotel room, and outdoors in pretty private spots, but she's reluctant to take the next step and be in a more exposed place. She's more shy about that than the thought of partner swapping. I'm pretty sure I'll be able to make something happen on our next vacation or two though. She's definitely a lot more daring when we're away from home.
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