The Whore Goin' Trail (v0.2.2) by Ben Rosewood

You are a party leader of a wagon heading to Oregon. Gather your hoes, practice your pimp slap, and make sure to collect plenty of green on the way, player. After all, you'll have to prove to the Council of Pimps that you're a real MacDaddy and not some two-bit street hustler.
Pick your party from a variety of women, who vary in skill and randomised traits. Once you've made your pick, select what kind of art you want to represent your woman. There's 4 unique images each with 4 color variations for a total of 16 sets. You can also add your own artwork if you are so inclined.
You can have up to four party members. Will you fill your party with a harem of women? Or do you only want to take care of your one true love? The choice is yours. Just make sure to take care of your women, otherwise they might leave your party at the first opportunity to do so.
Be sure to buy supplies too. You'll want to buy essentials such as food and oxen to drag your wagon and fat stacks of cash. In addition, you might want to pick up some trade goods such as gold, alcohol, and animal hides. If you're feeling real fancy, you might want to pick up some extra items such as that new fangled camera.
Along the trail, you'll have to contend with wild animals, hunger, disease, river crossings, and numerous random events. As the party leader, it will be up to you to manage these dynamic encounters. With great risk comes great reward, and with the right moves, you might just be able to find a fortune on the trail.
You won't have to face these dangers alone,, either. Your party can come to your aid. Many of the women you can recruit have a variety of skills that will be helpful. Some women are skilled survivalists who can help you find animals and forage for food. Others have plenty of medical knowledge that can help treat injuries. Best of all, some can offer you the sort of comfort only a woman can.
When the trail gets too much, don't be afraid to take a break. As you rest up, you can interact with your party by talking to them, praising them, and even get intimate with each other. This downtime can be vital to easing the burden of the trail and keeping your party happy.
There are also numerous locations to visit along the way. These range from towns, river crossings, military outposts, and more. These places offer opportunities to resupply, interact with other wagon parties, and conduct business.
You ain't gonna head to a new land with empty pockets, are ya? There are a variety of ways of making money. Run a brothel, work numerous jobs, or sell whatever you find on your travels.
Every location has its own unique economics. Some places are rich in food, whilst others offer trade items such as alcohol and gold. If shop prices are too much, you can always engage in trade. Trades are random and savvy traders can take advantage of parties. Do your best to take advantage of each location, and make sure you don't get taken advantage of!