Alright so here is my suggestion. Let's say Annie is a single stay-at-home mom who casually uploads instructional and/or education tiktoks/short videos online
(like home remedies, dances and life hacks etc). She's just another middle aged content creator with a decent following.
Due to her attachment towards her son, she begins to feature him in her tiktoks/shorts which gradually develops into him being an active participant in almost every video of her
(which could be driven by Annie's mostly female fans going crazy over him). Soon, she notices suggestive comments about her son from ladies almost her age and some even shipping the two and such online attention influences her.
To push the first domino in their story, she uploads a series of short instructional videos
[with her son], that are focused at couples, teaching them how to hold hands, hug, cuddle, spoon, kiss, etc. and each time Annie subliminally notices her son's natural reactions. Then to actually kick start things, she accidentally comes across that milf site on the computer
(could from a trolling fan mail, or on her son's computer, or entirely on her own) -
and this where an abrupt and subtle easter egg could work, maybe featuring Shannon and her son or the other milf you posted about. Then they end up indulging/working on their own "instructional" adventures.
So, what do you think?