Karakai Jouzu no Takagi-san - Ijikuri Jouzu no Takagi-san (Doujinshi)

[MangaDex]

 

[RexNemorensis]

Absolutely CANON

 

[ribbitribbitsaga]

The transitioning is shit. She would've most likely win against him and have him caress her. The more challenges she wins the more it progress into penetration.
Also He's doubtful for his feelings towards her in that chapter. Even if he did realize it, his shyness and reluctance would get in the way of smashing her.

 

[Bearboi]

@ribbitribbitsaga big brain moments.