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That is pretty dark dude
As to the fan art... at least Anna's breasts are close to being the right size. Though I understand it's hard to render breast that are lactating in terms of size, shape, and nipples not quite correct, it is close enough.
Dark outcomes... Mr. Palmer hasn't really given us a clue. We could be treated to your usual failed marriage breakups that are ok(ish). Or things can go total scorched earth--though I doubt the nuclear level you are banking on is likely to occur.
But you do pose an interesting question and that is what the worst outcomes from Ok(ish) to total scorched earth?
I'd rate the ok(ish) outcomes would be Anna moving on and entering into a full relationship with Chris or maybe Jake. Yes some serious sex with emotional connections. Leans more to what most people have already seen in real life.
To add some hotter taco sauce to the above Anna gets pregnant from one of the above
Anything else from the above rating gets the audience to start walking into the weeds.
I'd like to see anything Marvin and Anna related being more into some serious kinks. And that is how I'd like to see it move in that direction if there really is a Marvin route. Keep Marvin as a background character getting his little perv in while Anna is dealing with the bigger fish chasing her and only in the end of the story does Marvin get a night with Anna. So call it a brush fire.
Most here would see Hank and Anna as either "Oh HELL yes" to "Oh frak NO!" It's a harder story tell to nail the plausibility side of the plot but rewarding if achieved. I see a reluctant Anna fending of Hank's domineering advances as well her own arousal of being dominated near to the point (like roleplay level) forced. Anna could really stop it if she truly wanted to but meekly protests and defends herself but the real truth being its only Hank who could really stop it from happening--which of course isn't happening. If there is to be "drugs" involved, I'd hope its Hank using Viagra and energy drinks for an all nighter that leaves Anna bow legged... that's a long ride with a 400-pounder fat dude 'bareback breaking' Anna with 8 goes at it all night that leaves Anna feeling totally guilty but secretly wanting to get used like that again.
Grant--well that to me seems to be more a story of "unfinished business" with something that happened in his past with Anna. Yah, there was that 'almost night' with Anna when she was home from college. But what else is hiding in the past that would be fuel for some scorched earth? Did Anna maybe let Grant take liberties with her that turned her on that she always regretted not having finished? Maybe a young college freshman Anna before she got her first real boyfriend got Anna aroused and it was that encounter that made Anna open to dating because what Grant started. It's still one of those things that people are looking for or will kill the choice as in Hank and Anna. The audience gets a two-fer with a back story and memories as wells as Anna/Grant adventure--perhaps as added salt for the wound Anna confronts David and says Grant is more a man then David is.
The dark horses for scorched earth are Marcel and Robinson. Robinson would be more an accident when an upset Anna lets Robinson get to handsy with her and things get out of hand. Marcel more a problem because it can go two ways. Anna can just see Marcel as an attractive "boy" interested in a mature Anna, or Anna can go the whole BBC gambit-- that it matters to Anna that he is black and its some sort of taboo or fetish kink of hers that she always wondered about.
Some Napalm
+Anna should fear getting pregnant from Hank, Chris, Jake, and Marcel not Marvin or Grant
+Anna gets 'owned' by Hank or Grant where she eventually gives herself to them when they want her
+Anna gets 'used' by Marvin and eventually becomes his toy
+Anna finds 'adventures' with unnamed NPCs where her and Kendra go and have a girl's night out at a dance club and meet up with some guys; Anna gets involved with two guys and nearly gets a 3-some. More an emotional guilt trip and arousal event.
+David can't prove it, but is pretty sure something is going on, just doesn't know what
+lastly the whole kitchen sink of other genre tags that would fit... perhaps the last scene of the game of Anna being in a hospital with a new baby
Wow, that's... that reads more like a wish list of Anna's sexual activities than suggestions for bad endings.
Here's my suggestion for a bad, partially real, consistent ending that, if you have a little empathy for David's view of things, even contains some revenge without David being able to benefit from it.
After the player has fucked his avatar, in this case Anna, with all the employees in the office and the neighborhood, a scene occurs in which we see Anna riding Stromberger through the bed in a schoolgirl costume. After the orgasm, as Anna happily cuddles up to her surrogate father, she hears Stromberger muttering something in his post-orgiastic frenzy, which immediately makes Anna suspect that everything wasn't going right when her father died. She immediately confronts Stromberger. The old fox is silent, but the way he is silent and the expression on his face allow only one conclusion - Stromberger, the man she just had sex with, is responsible for her father's untimely demise.
Horrified by what she has just done, full of hate and self-disgust, she storms out of the apartment.
And turns to the number two protagonist who Anna believes has something like romantic feelings to be found there - Jake. She goes to his house. But Jake has his girlfriend at home. The two women fight each other and Jake throws Anna out of the apartment.
Now Anna believes she can find protection and comfort with her boyfriend Chris. Although she has had sex with Chris, she does not have any romantic feelings for him, but sees him as a friend. She arrives at Chris' house completely in tears. He takes her in his arms, listens to her and when Anna calms down a bit he tries to fuck her. She rejects him, but Chris is persistent and in the end we experience a sex scene that Anna ignores.
Afterwards, Anna gets fed up with the men and turns to Kendra and tells her everything. Kendra triumphs and just can't resist completely destroying Anna. She tells her about her intrigue and also shows Anna photos that show Anna having sex with different men.
The night ends for Anna with sleeping pills and lots of alcohol.
The last images show a woman lonely and alone, unconscious on a bed and David alone in a hotel room in front of the television.