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They were almost certainly intimate. The text alone is indicative of that. "I still care about you" and "this does not affect anything between you and I" implies that something romantic or sexual happened between them.
That stuff likely takes awhile to happen, and if he trusted Bella completely at the start of the month (more than Null, apparently), we can assume that this was a long con, that she had been working him for awhile, since he knew her for months. To get the trust of Chris-chan through likely UwU's and an exaggeration of sexual interest. I'd say that its very likely that she sexted with him at some point, sent him tit pictures, or something else solicitous.
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Now, if this ween is involved, I would argue that two unrelated people from across the US, discussing a honeypot, would a) guarantee that there were no innocent aims here, and b) suggest that they were trolling and had ulterior motivations, and likely wanted to get dirt or find something funny for internet points. It could be why they sat on the bdsm texts on the 23rd and knowing that Barb was getting diddled on the 17th, that they had hopes for more content. That could also explain why the audio had to be leaked by Fiona (someone who came into this in July), because they may have wanted more graphic content. We already know that Bella was willing to film Fiona and Chris having sex, and had convinced him that this would be okay, that filming people having sex was normal. Is it too much of a push to assume that she was also trying to convince Chris to send her an actual sex tape of him and Barb fucking? Especially if they were in a
faked lovey-dovey relationship online for an extended period of time (again, enough that he trusted Bella more than Null)?