Anon asked “Hey I love your writing and I was wondering if you could do an imagine where Sam and Dean make a bet on who the reader would rather date?! And she ends up liking Dean more so Sam comes up with a prank to get back at him! Thanks keep being wonderful!”
So because I think I’m a clever little shit, Heads, I win fulfils this request technically. I played with the interpretation ever so slightly so that it fit into my character-headcanons. (Initially I couldn't imagine them asking the reader to choose, especially in recent seasons.)
However, because I’m also a desperate teacher’s pet, so I wrote Tails, you lose, which I think answers what Anon was actually expecting, set in a different time, when the brothers actually did prank each other.
I really hope Anon liked it though. This was my first ever request and I was nervous to do it. Hopefully it’s fun and has some heat.
