Heh... That's what I like about it.
What I don't like is that it's a cookie-cutter meme, always with the same expression, just like the horny insta-ho tongue-bite (which I hate so much more). But there's something to be said for literally being fucked stupid. Goofy, ungraceful facial expressions during sex ftw. As long as they're more natural than ahego, which is in all cases performative, with a few given exceptions once every 10,000 orgasms. I mean, someone is bound to make it naturally at some point and a natural cross-eyed orgasm without the tongue is pretty hot in itself.
I don't think anyone can really guess accurately if they don't know her. Aside from the fact she likes hockey since she's clearly a big Blackhawks fan.
As far as I know, Jeremy doesn't offer Ian pics if Ian has successfully slept with her at least once, correct? Key word: successfully. Jeremy still offers if Ian can't get hard in his first Allison encounter and doesn't sleep with her after that point.
This is just one of the many paths there wasn't enough time for Eva to apply the proper text for. One of the pitfalls of such a widely branching game with resources too limited to execute every path smoothly.