What's the meanest thing you can do to a sleeping girl?
I once saw this one hentai where this guy kept getting forced to have sleeping girls on public transportation give him blowjobs.
Japanese public transit is super overcrowded, so the crowd around him would jostle him and force his crotch into her sleeping face, with his cock naturally making its way into her mouth.
Can't remember the name of it though. Shame.
Was it an anime? If so, then it was Cream Lemon "I Guess So". One of my favorites of that series and frankly, almost acts as social commentary/satire.
Sorry if I sound like one of those academia types though.