Whenever the list of events in the next update includes Aiden's name, the guesses about what task Sophia will have to fulfill next multiply. However, I think that when making these assumptions you have to take into account three factors that are well present in the words of the developer:
1) The story is already planned out (and also already written!!!);
2) Before the removal of the so-called Dylan's twist from the events of Day 18, Aiden and Dylan's stories, in the original idea of the developer, should have developed hand in hand with each other, with a mutual participation of one in the cause of the other. In fact, before this part was removed from the story's narrative, behind Aiden's blackmail was Dylan's desire to see his mother return to wearing sexy, provocative clothing as she did when she had not yet entered (to his way of thinking) a mid-life crisis. To make this fantasy come true, Dylan had contacted Aiden, the more asshole among his mother's students, who, in exchange for some mysterious computer data, had willingly accepted the assignment. In turn, Aiden, in order to justify his demands on Sophia, had covered it all up with an always valid blackmail: either you do what I ask every time I ask or I will beat your son. So Aiden's mission would be to blackmail Sophia into wearing increasingly revealing and sexy clothes according to Dylan's desire to see his mother expose more and more of her legs and cleavage at school.
3) When later, at the urging of his Patrons who didn't like Dylan's disloyal behavior towards his mother, L&P had decided to remove this part of the story, his comment about it (I don't really remember the words he used at the time) was that this change of direction would not result in major changes to the original plot.
Now, if originally the goal of Aiden's tasks (under Dylan's direction) was to make Sophia feel like a still-desirable woman through a crescendo of increasingly sexy outfits to wear to school, and if removing Dylan's oversight of these tasks didn't change the substance of the tasks themselves (the story is already planned and written), I wonder:
What do vibrators, vibrating eggs, and other sex toys have to do with Sophia's midlife crisis? Do you really think Aiden could have ever planned something like this without Dylan, upon learning of it, calling it off? It's one thing to see her expose more skin, it's another to turn her into a porn star.
However, I don't think Aiden is really interested in Sophia from a sexual standpoint. Mind you, in this game all (or almost all) characters are potentially interested in getting into Sophia's panties, but Aiden, unlike other young beginners in the game (like Dylan and Sam), already has a girl to entertain himself with and experience his first approaches to the world of sex.
Aiden (and in this I see him very similar to Don Morello) seems to me more interested in something else: his main goal seems to be the dismissal of the power that Sophia (as a representative of the school authority), should exercise towards him and his companions. Aiden, in my opinion, is more interested in showing himself as the one who is capable of subduing a teacher in front of her class (or an audience of her peers), rather than in establishing a typical blackmailing relationship with Sophia (like Mr. Bennett: fuck me or I'll ruin your son's future) which, however, should be strictly private and would not bring any kind of recognition from his friends.
Therefore, I believe that Aiden's tasks will always aim at the goal of embarrassing Sophia in front of his pupils and not at that of deriving an exclusive personal sexual advantage from them. For her part, Sophia, according to the original intentions with which all this was initially conceived, in virtue of an ever-increasing awareness of her sexiness, would have the opportunity, through these tasks assigned to her by Aiden, to increase the shamelessness necessary to push herself definitively in search of pleasure as an end in itself (hedonism as a pretext for cheating).
These types of tasks could, for example, concern a type of environment that so far has not yet been introduced in the plot of the game: the school gym where Sophia teaches. In fact, we must not forget that Sophia, in addition to biology and literature, also teaches sports, and in a school gymnasium (the filmography of the 80's teaches us this) there is a whole series of sexy and embarrassing situations in which Aiden could put our little Sophia: from asking her to show up without a bra under her shirt (bouncing boobs) or without panties under her leggings (camel toe) to leaving the shower curtain open so that everyone can see her completely naked.
Finally, I realize that all of this dissertation of mine, is based on statements by L&P that are beginning to be a bit dated, so in case I missed any of his later passages I ask you to fill me in on that.
