lol. This answer changes all the time, just depending on what I’m working on and how I’m feeling. BUT today I’m gonna say Sam/Jimmy in general but specifically in the context of winjimstiel.
I tend to write Jimmy very flirty and sensual and with a lot of mischief in his heart. He’s a lot of fun for me, and I think he’d be a lot of fun for Sam, too. He’s a bit of a line-pusher so I can see him really laying it on thick when he and Sam are in public (bonus points if Dean’s also around b/c we know what Jimmy would do to tease Sam.) Also, I like to think that Jimmy would be all over Sam and would enjoy the hell out of him taking control. Outside of that, I think they’d have a lot to give each other. Jimmy’s a free spirit and Sam’s more grounded.
The two could have a dynamic I’d love to explore a little more in all kinds of contexts. They’ve been on my mind a lot recently.
Thanks!
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