After finally being able to retire from the family business. Sam,Dean, and Cass are finally able to find love. But with who you ask read and find out.
The Year is 2024, Sam, Dean, and Castiel have finally gotten the monster situations under control. After killing all of the Alpha monsters the young ones started falling apart. Most went into deep hiding but the ones who couldn't handle the freedom ended up being taken out by the Winchesters. There were a few that the boys were able to make treaty's with. They helped police their people and called on the boys is the problem was beyond their control. The vampires stopped feeding from humans. The werewolves stopped taking people's hearts. The boys created a team called the night stalkers to police the supernatural world.
Jack is running heaven with love and happiness, the souls are happy And able to roam free. Jack listens to everyone's comments And concerns with an open mind. And the remaining angels have learned that humans are not something to be played with. After Jack got Cass out of the empty he went back to earth to help the boys. He didn't loose his wings but he became a fallen angel.
Even though they no longer hunted unless it was absolutely necessary the lived in the bunker. This way if other hunters needed information about anything the boys could find it for them. They also made it possible that if a hunter needed a place to crash they could do it there.
For the first five years the boys were happy but one day Cass noticed how Sam and Dean started getting upset and moody. He watched as they got more and more depressed. So one day Cass decided they needed a guys night out. He was hoping that if the boys got laid they would be happier.
Finally one night Cass took the boys to a strip club. They did have a good time but they were shocked by the dancers. One of the dancers was the angel Anna. Another dancer was the demon Ruby. Then the last demon they recognize was Meg.
There were a few other dancers but these three were the ones to catch the boys attention.