Groundhog Day, but the guy keeps coming back to few minutes before he loses his virginity, when the girl is about to take a shower.
Typical time loop improvements happen, he got good at kissing, got good at sex, even made the girl cums! But the loop repeats. He then called his friends for a gangbang, but no luck. Desperate, akin to the suicides in the original Groundhog Day movie, he called a black man. In a typical development, she got addicted to black penis and he regretted it, though sadly the black man's opinion remain unwritten. The loop repeats once again, but this time it's the final one. The guy opens up about the loop, they had lovey-dovey sex (I know, disgusting) and the loop finally ends.
In the end the guy still isn't sure about why the time loop ends, but he knows one thing that had changed: he's into NTR now.
Base +6, Nobody_Know +9, wavedash +21, Xhion Pime +7
It's like playing a simulation game without any walkthrough or save point and game over for more than 100 times, and you have no clue what's the problem. Man I'd rage quit after few times if I was MC