One Day a Message Window Appeared Out of Nowhere!? - Ch. 40

[MrTurtleMan]

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It could also be lying down or being asleep with a woman? Probably not but this manga comes to mind since you mentioned him being asleep. Considering this is almost guaranteed to be selling a fanbox I'll assume- in fact I just checked and yeah author's pixiv and fantia have R-18 works out the wazoo so it will definitely be sexual act related.

To be fair it could also mean different things between the R18 version and the main series

 

[TestAddress]

maybe it doesn't HAVE to be different women, maybe it can go up by repetition with the same woman, but that'd require testing of course

If he held hands and kissed Makishima Yuu for only 3 times, he is pretty much as Makishima Yuu said, "DEADBEAT".

 

[BlackElite]

If 3 is the count per person, not per act... Then one is from his ex, and leave us a a question, where does the other 2 comes from

 

[Ungrave]

If you're disappointed then you can take some solace that in a parallel world to his is the r18 version of the story.