I have been looking this whole time and I can confidently say that it had no cross dressing plot, not yuri or yaoi, it was a romance between the transfer student female lead, the male lead was a delinquent type who was the top fighter or something like that, and the goons were so funny, the main couple was shy and angsty. The running gag or bit was the main couple being constantly interrupted by the delinquent’s lackeys.
No, it wasn’t the manga
Glittering And Glaring: My Destiny Romance With Violence (wrong art style)
The delinquent and the transfer student (yuri)
Hana Kimi (cross dressing)
Secret girl aka Baku ni natta watashi (cross dressing)
I belong to the baddest girl at school (girl is the delinquent)
The delinquent’s first love (WEBTOON not manga)
It was the manga
My Darling! Miss Bancho
( ̄∇ ̄")

I'm looking for a manga I read a while back (possibly a few years ago) about a Yankee or maybe yakuza guy who falls in love with a girl. There's possibly a school life kinda plot involved I'm not sure but what I do know is that it was hilarious because the guy and girl would get close to having intimacy or a moment and it would always get ruined by the guy's lackeys/goons.
Any suggestions or thoughts wold help thanks!!