mkon125 — Sugar-Dating Time Loop: Reload Until the Cold Adult Student Role-Player Falls for Me and Accepts a Creampie

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A man matches with adorable adult student-style sugar baby Yumi Nijimura, only to find her painfully cold and irritable. She gives him a gloved handjob, leaves immediately after he ejaculates, and refuses the sex they had discussed. Because her face is too cute to give up on, he uses a time-loop app to restart the date repeatedly. He studies her favorite anime, Takobee, to raise her affection and reach a timeline where she warms up, falls under his spell, and agrees to sex with an internal ejaculation.