Suda-kun no Himitsu
Complete | Tamuko kuwata | 2019 released
Our main character has a thing for cute things, even though he is seen as rather gloomy, and it leads him to crossdressing as his hobby. He ends up attempting to get a sugar daddy and it goes rather poorly. Thankfully a classmate witnessed the scene, and helped. Leading to a knewly opened door ^^~.
Hitotsu Yane no Shita no Kedamono