The Whore Goin’ Trail

Oregon Trail, but you're leading a wagon full of hoes toward a sit-down with the Council of Pimps, and they want proof you're a real MacDaddy before they let you in. It plays the premise straight, which is exactly why it's funny.

You build your party from women with randomized skills and traits, then pick one of four art sets in four colors each for how she looks (custom art works too if you'd rather not use what's given). Up to four women can ride with you, and how you treat them decides whether they stick around or bail at the first chance.

The trail itself is the game: manage food, oxen, and cash, cross rivers, dodge disease and wild animals, and react to whatever random event the road throws at you. Party members pull their weight with survival skills, medical know-how, or other talents, and towns and outposts along the way let you resupply, trade, or make money running a brothel, working jobs, or hawking whatever you scavenged. Every stop has its own prices, so getting a good trade means knowing where you are as much as what you're carrying.