Are people here dense, or do they not get the point of this?
No, Ayumu doesn't need to be confessed to thrice to get Rin's feelings. It's just that with him getting closer to confessing to Urushi, Rin resolved to finally go past her own crush in this way.
Ah, yes, a common plight of boys being insecure about not being attractive until they get laid for the first time and stop caring about it.
For funny points, imagine him telling that he started crossdressing because he hated his body not to his mom, but some fat otaku classmate or something.