These specials feature the Oshitari cousins in a Manzai (&#28459;&#25165;) setup [a style of stand-up comedy in Japan, which usually involves two performers&mdash;a straight man (tsukkomi) and a funny man (boke)]. 
Story 1 involves Oshitari Yuuhi who is tired of being the tsukkomi and wants to try his hand at being a boke but with disastrous results. 
Story 2 is about Oshitari Kenya in the role of a boke whose jokes didn't get through to the audience in a joint Namiwa-Seishun Talentshow.

Tennis no Ouji-sama OVA ANOTHER STORY - Kako to Mirai no Message