ばくあね!! 弟いっぱいしぼっちゃうぞ!

Synopsis

The protagonist fails his first time with his lover due to a past trauma. However, his older sister and cousin decide to help him overcome his trauma through sexual lessons. Moreover, even the person that causes him trauma participates too. And so the older sisters' contest for the younger brother begins. (Source: Official site)

Anime adaptations