So a few people have ran into this.Thanks for taking a look at this! I'm guessing that your theory as to how I might have gotten that dialogue is probably what happened. I do know that I helped Lauren win the election (so she didn't lose the bet) and she never had any kind of sexual relations with Matt after the election.
It will forever remain a mystery, though, as I've already wiped my saves and started a new play through. Hopefully, with the info you provided, I can avoid it happening again this time around. Again, much appreciated!
What you did was, when you first started the game and met Matt for the first time, he offered to help Ryan fuck Jacky on the condition that Ryan let Matt fuck her too. Telling Matt yes puts Jacky on the NTR path.
Lauren's NTR path is based on if she wins or loses the election.
So, originally Matt was going to be more of a buddy than an antagonist. More of a sharing route.
However when Lauren's story was unfolding, one of the idea's pitched for how it would unfold required an antagonist.
We could have made a new character for that role but at the time the school didn't have much development and the only characters anyone knew was Matt, Megan, and Kenzie. We wanted to have the characters we knew about involved in the election but adding new ones and having a harem, sharing, and NTR route was just to much. So Matt became the massive prick you all know and love today.
There is a continuity issue that you pointed out for players that pick NTR for Jacky but not for Lauren. It's something we should address. When I was writing the club scene I had never even considered that a player would want NTR for one and not the other. At some point I'll get with Will and we'll ether change the line or maybe make it conditional. We might also redo that first conversation with Matt to make it more clear to players what they are getting into if they don't tell Matt to go fuck himself.