Josou Gyaru Bitch Gakuen ~Half Musume Judy no Yuuwaku~

Thanks to Asuka and Miyabi, the protagonist is completely captivated by the charm of cross-dressing girls.
He enjoys having sex with them almost every day.
One day, Miyabi invites him to visit her villa during the upcoming long weekend.
Asuka, who he always hangs out with, introduces him to another friend—Osaki Judy, a half-American cross-dressing girl from the next class.
She's also a cross-dresser, but she's a fashionable, busty shemale who's had breast augmentation to wear women's clothes more naturally.
With her in tow, and her passionate, Western-style approach to the protagonist, his erotic life with Asuka and Miyabi becomes even more intense.

[From the official website]