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First: I want to say I'm enjoying these stories you did great

But second, as the OP said continuity: In the first game was there ever even an option to NOT tell Your BFF TOM about the succubus and the contract? Because in the second one it automatically treats it as if he never knew.

I specifically remember scenes of Tom warning you about becoming addicted to sex because of the contract in game 1.

Hmm, I'll check it out

It was directly during the intro of 2. It was in red text as if it was a decision you'd picked previously. (if that helps)
(during the parts where old people start to come by)
Decisions I remember making (As sometimes they matter?):
No futa

all the way with Avi

Let him see breasts
Make him stop

Almost all the decisions you make have exclusive hidden content. in order for you to discover all the content I created a playthrough of the game. (it is located in the download folder of the current versions)

I've been looking into what you've noticed. 

Tom doesn't know that the MC became a girl by the succubus. I mean, he knows where it happened and what happened, but he doesn't know the method of the MC becoming a girl, and that's very important, so I've highlighted the text in red. 

I'm glad you paid attention to it, you will need this information in the future.