Paizuri Cheerleader vs. Sakunyuu Ouendan!
Japanese title: ぱいずりチアリーダーVS搾乳応援団!
Type: OVA
Source: Visual novel
Episodes: 1
Status: Finished Airing
Aired: Jul 18, 2014
Duration: 28 min
Rating: Rx - Hentai
Studios: T-Rex
Genres: Hentai

Based on the erotic game by Marine. 

Shin belongs to a cheer group. Though he wasn't interested in it, Yuko, his older sister, forced him to join it... As a matter of fact, there are only two members, Shin and Yuko. On the other hand, a cheerleading club has a lot of members. One day, Shin accidentally collides with Chieru, a member of the cheerleading club, and she gets injured... In compensation for her injury, he decides to work as a caretaker of the cheerleading club. But days later, Satsuki, a coach of the cheerleading club, suddenly orders the members, "You should give him a titjob to overcome your sense of shame!" As they are all confused, Satsuki starts giving Shin a titjob...!

(Source: VNDB)