There are some interesting but confusing thoughts so I wanted to jump in too!
You can base it on the fact that Drew has a known past of fucking David's family members, not sharing them with him. They shared with Hunter. What are you basing Drew seeming nice on? They've had one line since being introduced in the current timeline.
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The facts we know about their past is that they had sex with David's sister and mother after learning Hunter's techniques.
They explain the situation to David when caught, but they went through with it, even having a 3some with the Keira and her mother without Hunter even present. Sterling was offered tutelage by Hunter as well and didn't take it, so that was obviously an option.
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Sterling is fully aware of who Drew is and what's they've done, as he read it all in David's notebook with the story of Drew. Plus, as mentioned, he was warned by Hunter. So yay, no name badge needed
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Thinking they'll fuck Sterling is a thought, I'm not sure what lead you there, but it could be written in, i just don't think it will,
as long as we're guessing. We're nine chapters in and I can't think of anything that'd suggest Sterling is able to be moved toward sissification.
He might balk at the thought because he knows Drew past and the part they played in tearing his family apart. That might make him the least bit hesitant. They're known as Hunter's protege to him. I don't think anyone said Sterling is opposed to 3somes, it's the personnel (and personal) component that seems like a stretch. Also, Drew looking for an in is pure speculation, so maybe but who knows! We can only work with what we actually know.
Obviously you're entitled to think whatever you want, but you started each of these quotes with questioning other's opinions so I was giving you context into why someone would think these things, as requested. I'd be interested to know why you think any of the things you suggested.
A point of interest to me in the Drew situation (which i was hoping would be used to support some of things you're saying haha) is that Drew states Hunter and Drew's partnership started when Hunter found Drew playing with Kiera's dirty laundry. Hunter just states he discovered Drew's interest in Kiera. If Drew was just a few years out from a sex change at the time, it'd be funny if Hunter actually walked in on Drew beginning to think about cross-dressing, and misconstrued the whole thing. The only problem is, why would Drew then follow Hunter's teachings. Excited for some more details moving forward.