I hate to say it, especially since I want her to end up with him (FFS, this MC actually likes the best girl for once) but he deserves the treatment he's getting from Enome. Kikkuru keeps letting her get molested, always allowing it in ways that--to Enome's forgivingly benevolent eyes--make him appear youthfully incompetent. This time, she got raped--if the SFX are any indication. He appears, to her, the same little boy of the past that she used to dote on and comfort--the one whom she feared couldn't handle what life was throwing at him.
What "man" is Enome going to see in someone who's effectively still like that, especially when she's in dire need of help?
...Kills me to piece all that together, knowing that the only time a mangaka can be this logical and reasonable about romance and romantic choice is when the girl is as beautiful as Enome, and she has no interest in the MC. I've seen MCs suffering females doing anything to them from subjecting them to constant hostility to openly flagrant abuse, and the MCs eat it all up with puppy dog eyes because said females let up on the punishment for a split second.
I guess it's because it's just a gag manga (yeah, sure it is--after that Nightmare arc that just ended). Funny how someone told me that a romantic comedy about a couple, one featuring a girl with Enome's level of looks, needed competition from random girls--most of them indeed out of nowhere--in order to avoid failing...but a story like this where the status quo (nothing happening, not even progress in any direction, least of all the best direction) is doggedly maintained is just fine.
I doubt she will ever see him as anything more than a little brother due to age gap and knowing him since he was a kid. I wouldn't expect any romantic progress in a harem manga anyway.