Epilouge
10 years later!
Mary was proud of her family as she watched over them alongside John, Bobby, and Castiel. Lisa was standing behind Bobby, looking mostly at her son. The four adults' hearts were brimming with pride at how this family had changed course. They were family, so they sat down on the same bench in a park and enjoyed a heaven together.
Ashley and Sam both retired and stayed at home with Justin and Tara. They both refused to let Justin hunt with Ben, no matter how much he begged, but he was fully trained by the two best hunters that were still alive. Justin was taught under the instruction of Sam and Ashley Winchester; some argue they were the best of the three and Dean was just too driven by rage and vengeance to be considered a good hunter, he was just a scary one. Since Justin was not allowed to go with Ben, he agreed to stay at home to watch out for his little sister, just like Dean used to do with Sam and Ashley.
Ben continued hunting shamelessly, but he was living back at Bobby's with his wife- the girl he had a crush on years ago. He finally worked up the courage and proposed, making Raina Eunice Braden the newest member to the family.
Ben and Raina would go to San Diego every month. Ashley was Ben's mom, as she had been for 14 years and now Sam was his father instead of uncle. He had been a father for Ben for 10 short years, and when asked about it would always say he would have it no other way. Ben treated the two remaining Winchesters as a library, resource, fragile artifact, and strong family to fall back on. Whenever Ben knew he would be gone on a long, treacherous hunting trip, he would send Raina to stay with Sam and Ashley to ensure he kept work away from home, something Dean was never able to do, and that his love stayed healthy and safe while she carried their first child!
Everyone was happy to be out of the rut they were in before, everyone except Dean. He became his worst nightmare and there was no cure. He was a demon, dead to his family, and now the King of Hell with Adam underneath him.
Every weekend Dean would check up on Ben and the Impala. He didn't care since it was not a demon's nature to, but he always felt better knowing his son was happy and Baby was running well. Afterwards he would stop in on Sam and Ashley- they were aging and lazy, but they were happy. Justin had grown up to follow his oldest father's footsteps with Tara.
Tara- she looked exactly like Ash, she was beautiful. She was the first generation of blood Winchester not to hunt, and that was more than Dean could bargain for. "Keep it this way" he said to himself, just like he did every weekend. "I'm proud of us."
Castiel continued to be the Winchester family's guardian angel and felt so much better now that most of his work was to sit and watch them around the house. He would drop in routinely to spend time with the child he once spent hours listening to think and also visit with his oldest and closest friends. He had learned so much from the Winchesters, he was still so engrossed in their way of living. Castiel knew Ben was safer than his trainers once were, so when Ben went on a hunt, Castiel would spend time riding in Baby with him. Cas missed the feel of the Impala under his seat and racing down the road, it never felt as good as when Dean would drive it, but it was still good. "You know he is proud of you, Ben" Castiel said one day once the case was finished and he was going back to his family's home.
"He should be. We bettered ourselves. We moved on and stayed Winchester strong" Ben answered. "But it makes me feel better knowing he still has some emotion and feeling towards us."
"He always will, family was his life, now it is his undoing."
AN: Thank you for coming on this journey with me! This series was my life for so long, I will miss Ashley Winchester as much as you may. I appreciate all the support, I was not expecting this success at all! It really is true, family don't end with blood...and we are the most devoted fandom out there! The end guys, I thank you for everything! Follow and favorite me as a writer to read more sister fics in the future! Much love, Ashley!