Katawa Shojo (かたわ少女), if visual novels count. My first time.
If not, then Katawa Crash, a flash game based off nanaca crash that I played years ago and which is very slightly related to the VN. It's a game where hisao gets rejected and kicked so hard that he flies multiple kilometers, boosted by interactions with people as he lands and several special events (Obama features in one of them). Wild game.

That ~75km one took about 25 minutes before I came to a stop. I got the multiball bonus on the way, which helped.
This post has been edited by dragontamer8740: Feb 27 2022, 11:16