Sam knew that, even though he had a slight preference for women, gender didn't really matter to him. He had only fooled around with a couple of guys before, Brady being the most serious of flings before Sam got together with Jess, but he had never gone the whole way with him, or any guy for that matter. And he had never really wanted to. None of the guys he had been with made him feel comfortable enough or wanted for more than just one night to give them everything.

Sam held this opinion for a long time. It wasn't until he was in a office of a dead professor who had taken a nose dive out a window did he seriously consider changing that opinion.

The janitor was short, but really attractive in his own unique, almost mischievous sort of way. It was highlighted in the way he moved and talked. Sam knew he had a chance with this guy, especially with the way the janitor was checking out his ass.

Sam almost asked the guy for his number, but he left the office before Sam could ask. Sam hoped he would get another chance, so he just smiled softly to himself and got on with the job.
-

The janitor was now a suspect, which really sucked. Hopefully they could clear him soon so Sam could "put the moves on him" like Dean had said.
-

The janitor had turned out to be the Trickster. Sam felt like disappointment was an understatement. The only guy that Sam had ever truly considered fucking or being fucked by, turned out to be a monster. Just his fucking luck. And even after they figured out who and what he was, it didn't stop Sam from still wanting him. Which left Sam feeling slightly uncomfortable. When Dean killed the Trickster, Sam couldn't help but feel a little sad. The janitor had been nice and flirted with him and made him feel like he might have been interested in more than just one night. Sam sighed. Some things just weren't meant to be.
-

When Sam realised that it was the Trickster that had forced him to live Tuesdays over and over again, the first emotion Sam felt was betrayal. Which was irrational. The Trickster hasn't owed him any sort of loyalty, but it still hurt. Sam had mourned for him, even if only a little, and to find he had done this wrecked Sam and messed with his emotions.
-

Sam lost it when Dean died. Permanently this time. He was angry and scared and betrayed. He needed to find the Trickster.
-

Sam learned something about himself that day. Firstly, he killed Bobby so he could save his brother. The one man that he saw as a father figure, he sacrificed to the Trickster. That in itself was fucked up. It worried Sam. How far would he go to save Dean if he died again?

Secondly, he was still attracted to the Trickster, and from that smirk on his face, the Trickster knew it too. Sam couldn't believe himself. After everything this monster had done, Sam still wanted him.

At first, Sam thought the Trickster might have put a spell on him, but Sam had done some anti-love and anti-attraction spells on himself, attempting to undo anything the Trickster might have done to him, but nothing changed.

Sam was almost angry with himself and his infatuation with the Trickster, but there was nothing he could do. Sam just supposed he was attracted to danger. That's why he started fooling around with Brady. As much as Sam had wanted Brady to get back on the straight and narrow, Sam had to admit to himself that the bad-boy vibe was really hot. Don't worry, Sam knew he was a walking cliche.

But then, the Trickster had smiled sadly at him, his expression softening, showing true emotion and sympathy for the first time. He sighed.

"This obsession to save Dean? The way you two keep sacrificing yourselves for each other? Nothing good comes out of it. Just blood and pain. Dean's your weakness. And the bad guys know it, too. It's gonna be the death of you, Sam. Sometimes you just gotta let people go." The Trickster said softly, as if he was afraid to scare Sam off.

"But he's my brother." Sam said brokenly.

"I know, kid. I understand in more ways that you can possibly know, but understand, this is what it will be like when he's gone." The Trickster said.

"Please, please just take me back to that Wednesday." Sam pleaded.

The Trickster sighed. "You Winchesters." He said almost fondly. "You're going to be the death of me."

The Trickster clicked his fingers and Sam woke up once again, and it was Wednesday. All over again.