Depression of the Anti-Romanticist (2010)

Blurb:
Having lost their parents, Shiroyama must put aside his dreams and work hard to support not only himself, but his younger brother and sister. He steps into a world that he knows he must guard himself safely from, to protect himself and the ones he cares for. A world where transvestites work at entertaining patrons and alcohol flows freely. A world that offers him many firsts, including a kiss. But is it enough to light the fires of romance into his cold heart?

Source: www.anisearch.com/manga/12523