Cowboy Bear Bastion needs a night on the town. So why not have one with his best bud, handsome rancher Taylor Hawke? When these two men-hungry pals spend a summer evening at a bar called Cowboy Up!, things start out smooth. Taylor's on the hunt for easy prey, and Bear meets an interesting cowboy painter named Welsey Westward, whom he calls West.
Like most of Bear's evenings on the town, things become chaotic after a few too many drinks. Taylor becomes easy, and Bear loses his temper. Soon a brawl begins at the bar, and Bear and Taylor end up leaving early. As if things can't get any worse, they get into an argument on their drive home, and Taylor dumps Bear off in the middle of nowhere. Great! What's he going to do now?
Enter West, again. The painter finds Bear stranded on a back road, picks him up, and takes him back to his cabin. An attraction builds between the two cowboys and lust transpires, risqué paintings are revealed, secrets unfold, and mistakes occur. If only time could be reversed and tonight wouldn't have happened ...