I remember reading a manga where there was an event at school and they were voting for a guy to crossdress and they were vying for a cute classmate of theirs, but he had a bad experience from trying to put make up on and he thought he was ugly, so a friend of his volunteers
Please help! Thank you!

I believe Seinen wa Ai o Kou is what you're looking for. 😃

It is! Thank you 😀