Manga recommendations:
1.) Ookami Shounen wa Kyou mo Uso wo Kasaneru (The Boy Who Cried Wolf Tells Another Lie Today)
Keitarou Itsuki is a boy normal boy who is avoided by girls because his scary eyes. He likes one girl who hasn't shown hostility to him, but that girl flat-out rejects him. Depressed, he asks his sister for advice. Upon waking up in his sister's salon, he finds himself wearing girls' clothing. After which, he saves the girl he likes from other guys to learn that she is androphobic.
It's a good manga with nice development, and it's not all about him cross-dressing. The main point of it is that you'll have to face the consequences of continuous lying.
2.) Himegoto / Himegoto+
In a Hayate-esque situation, poor student Hime Arikawa is being chased by Yakuza thugs trying to collect a debt credited to him by his irresponsible parents. Realizing Hime is broke, the thugs get an epiphany that traps are cute af and attempt to rape him. At which point, the student council helps him and pays off his debt, but he has to crossdress as their student council dog for the rest of the year.
A lighthearted slice of life comedy manga with some drama, Himegoto is a good read, yet a bit too circled around Hime's unending humiliation before the world. It's also an anime if you prefer moving pictures, but each episode is only five minutes long.