While not ideal experiences, he did he go all the way with Hanada, even if it didn't last long, as well as with glasses girl (got interrupted but it was implied he finished the business after).
Yep, you're right. At least with Hanada because I don't remember where glasses girl was in the order, but what happened with her definitely 'counts.' I'm kind of wondering how I forgot about that. Aoi, the second girl, I guess technically counts since Terumi counts it, but I always considered that one a copout.
And yes, I seem to remember that he's the one who gets tossed by the girl afterwards, to the degree that he's had relationships. Not that I can recall many of them getting to girlfriend status, but I also forgot that he went all the way with Hanada, so my memory's faulty. I blame my binging basically the first hundred-plus chapters.
EDIT: Went through the timeline using TV Tropes (because I couldn't find a better resource) and I hadn't forgotten as much as I thought. If I count Aoi, it's her and two official targets following, and Yuu's the first real arc since the last girl. So Aoi (daddy complex), Chisato (who bailed when the experiment was revealed), Iyo (was cheating on her awful boyfriend; one night stand), and now Yuu, with Miya (yandere) and Asahi (issues with him being her cousin) not getting there for various reasons. He's not been as cock blocked as I seem to remember...maybe my impression is a result of the generally slow pace because of chapter length. I mean, 150 chapters in and we're only on the sixth girl.