In the town of Tombwood, the player takes the role of a decadent bounty hunter with a troubled past. The town is facing problem with a gang of bandits that call themselves the Black Cactus Gang. Various bounty hunters to visit the town and among them is Connie, a former ranger that's on a quest for revenge against the Black Cactus Gang. The player will take a part in helping her while facing his own troubles.

Cowgirl Trainer is a JRPG with turn based combat featuring dating sim elements. Level up, buy and equip items, fight a variety of enemies, spec your characters to suit your strategy. The game features side quests to go along with the main quests. Explore the desert western setting of bounty hunters and outlaws. Use D20 (Dice 20) for persuasion checks and certain encounters and decisions you make.

The dating element features a system of talking, giving gifts, and of course, adult scenes. The adult scenes are accompanied by mini games that if successfully played will yield boons to help in combat as well. Developing a relationship with Connie is a core element of the game and "training" her in the ways of making love is part of the fun.