Lucky Dog 1

Lucky Dog 1 is a Boys Love doujin Visual Novel by the company Tennenouji. (Whose artist is known for her work on Enzai and Absolute Obedience)

Set in 1930s America, it's about a particularly hot Mafia group called the CR-5. At the beginning of the game, they're stuck in prison, until the protagonist, Giancarlo Bourbon del Monte (mostly known as "Gian"), finds out that he can become the CR-5's boss if he manages to break out successfully. With his cohorts Giulio di Bondone, Ivan Fiore, Bernardo Ortolani and Luchino Gregoretti, he (hopefully) makes it out of prison intact, and to his hometown known as Daivan. The plot then chronicles his life with whatever character you choose to pursue, and whether or not Gian makes it into his position or not.

Very popular amongst the Japanese BL Game fandom, especially on Pixiv. Has a small-but-dedicated English-speaking fandom too, who pretty much unanimously agree it Needs More Love.

This game provides examples of:

 * Badass: Most of the characters count, Gian of course being the main "offender."
 * Bishonen: Again, most of the cast.
 * Bittersweet Ending:
 * Born Lucky: Gian.
 * Boys Love
 * Curtains Match the Window: All of the CR-5 except Gian.
 * Development Hell: The sequel.
 * Downer Ending: One of Giulio's bad ends.
 * Dropped a Bridget On Him: The CR-5 makes it to a small town during their escape, and notice a pretty farm girl, follow her into the woods, see that she's about to bathe in the river, and...find out that she's a he.
 * Emotionless Boy: Giulio, at first.
 * Gayngster: A whole group of them!
 * Gratuitous English: And Italian.
 * Gratuitous English Swearing: Ivan sort of talks like Panty.
 * H-game
 * I Love the Dead: Giulio, before he realizes sex is much better with real people.
 * Impossibly Cool Clothes: Especially the CR-5's prison outfits. Where the hell did they get those in the 30's?
 * Jerkass/Jerk With a Heart of Gold: Ivan.
 * Knife Nut: Giulio.
 * Nightmare Fuel Stationattendant: Even Giulio's fans agree the boy's a bit...off.
 * Precocious Crush: Rosalia's crush on Ivan.
 * Prison Rape: Mostly on the bad paths.
 * Somewhat-notably, in one optional scene Gian, a prisoner at the time, manages to rape the man who came to interview him. This affects your luck meter a bit, but...
 * Real Men Have Pink Hair: Luchino.
 * Red Baron: Gian is known as "Lucky Dog", and Giulio is "Mad Dog".
 * Stalker With a Crush: GIULIO.
 * Trademark Favorite Food: Giulio and ice cream.
 * Tsundere: Gian in every (good) route, Ivan as well in his particular storyline.
 * Visual Novel
 * Yandere: As mentioned above, Giulio.
 * You Gotta Have Blue Hair: Ivan is the aforementioned blue, Giulio is purple, Bernardo is green and Luchino is pink.