Visions of Valentines

This was a Valentine's Day oneshot created by TheIkranRider, a crossover between the Sleepy Hollow TV series and Supernatural. This takes place after The Missing Episodes as Sam recollects his past experience during one holiday.

Jenny Mills and Gavin Lucas were taking her camper to Washington, DC, going down I-95 as Sam Winchester was explaining on his past predicament:

He said he and Dean Winchester went to a nearby town that was infested by perverted love. In other words, love gone corrupt, and they suspected this could be the work of Cupid. The hearts of two victims had an unusual sign of unity inscribed on them. But it turned out to be something more sinister. Sam came across a demon twice, one that kept on whispering his surname. He attacked the stalker with a knife and the brothers and Castiel discovered a black suitcase that released an evil spirit belonging to the Horseman of Famine.

The future Witnesses were confused about this, and Sam confessed that he has a certain fetish for demon blood, much to Gavin's disgust. He wondered why he'd be addicted to demon blood, as if he was a vampire, but the truth was he was looking for a demon named Lilith, not the Heartless the two know. He also met his demon mentor named Ruby (Supernatural) to train him on using his telekinetic abilities while also mating with her at times. This made both Gavin and Jenny question his motives, even when he wants to save Dean from Hell's Anger swamp.

What was really toggling their minds was how would the Horsemen exist without the presence of Moloch. Gavin make a funny remark that he took a vacation and Lucifer took over. He was pretty much right since the Horsemen were known to house a different vessel once the other has perished. And Famine arrived in a black Cadillac Escalade, infected an "All You Can Eat" restaurant, and took the form of Lester Finch after dying from a Twinkie binge.

Gavin concluded they can be pre-incarnates since it all happened back in 2010, 3 years before Ichabod Crane and Abraham van Brunt were resurrected. So, Lucifer and his four generals overran Earth after the final seal was broken, when Lilith was dead by Sam's hands, while the relationship between him and Ruby really scarred Dean's trust. The world was suffering until the Winchesters encountered their "fake" brother disguised by Lucifer Himself. All the evil was reversed once the pit was open utilizing the 4 Horsemen rings and Sam and their "brother" dove in. Once the dam in Sam's brain broke, causing the hallucinations, the rest was history; he actually wished he would've been there during the Witnesses' war, but he doubted it since he and Dean were always on the move across the nation not even close to Sleepy Hollow.

After a five-hour drive, they went to the Vault and met up with Mary Winchester and the rest of Team Witness minus Molly since she was still at middle school. They just relaxed there, and Diana was willing to help Sam achieve his dream as a lawyer, whether it'd be online or otherwise; after all, Lara finished her education once she was first homeschooled before she reached high school, then enlisted herself in prestigious courses through college while she was adopted by Malcolm Dreyfuss and Jobe. Once he finishes, he can enlist himself as their own personal lawyer in Washington. Sam took up on the offer, although Ichabod wouldn't let any paranormal incident hinder his studies, and the team must keep a keen eye on him if he wishes to save Dean, which they've strictly disallowed. And if he gets influenced by demon blood, they got his back.