Yeah, it really happened... For recaps, Chapter 29 stated that Mashiro has multiple hymen. Looks like 5 based on the illustration. Nemuro was counting up to 4 clearly. After that, he says something along the lines of "this is the last one" but there was no clear count to 5, so even the JP readers seem to be confused if he was referring to the previous hymen #4 or #5 that he's about to break next...
Another thing to keep in mind is that time runs differently on different Voids. They could arrive as soon as a few hours on Dominator's Void, or up to a year. Since Win was able to grow up, the current Void runs faster from the Void where Midori's base was on, but we don't have a clear measure of Midori's Void vs Dominator Void. For more reference, when Amatsu no Yomi was attacked, from the inside it looked like a quick succession. But from outside their Void, the Dominators had prep time in-between. And Void Mueller also runs much faster than Amatsu no Yomi. Mashiro was actually born after Aoka.
And then there's that dude w/ glasses that kissed Win. His name is also Nemuro. Could be ugly Nemuro's little brother, cousin, or something else... He confirmed Gloria's at least alive, btw. When he was captured, he was telling Dolman about Gloria's hospital bills, but Dolman says he's broke.
Lastly, I'm betting on a 50/50 chance we can't trust Kyuu around Mashiro. Looks like she's going yandere, and she might see saving Mashiro as the root of Win's pain. (And we all know she's just a 3rd party in their love story.)
Personally, I wish the author would save the bad routes for his games... Mashiro's, at least...
Extra: Putting the nature of this manga aside, I gotta give it to the author for having the balls to go through with his creative choices, especially in today's level of censorship. Very often, we see authors trying to explore risky topics (less risky than this!), but they don't have the balls to go through with it, resulting in pointless, repeated, half-baked attempts that are better off not happening in the first place. Or in his case, outside forces telling him how he should write his own story. Not just with this kind of topic. Violence, gore, costumes... Google Play forcing a game to remove majority of its PAID character costumes... The current accusations on Visa & MasterCard... Even Nintendo's cartoon cow is being targeted by censorship because having a ring on its nose is animal abuse. Modern censorship is just so tiring. People have become so soft, they try to control everyone else, and antagonize people for disagreeing with their self-centered ideals.