Dean Winchester:
Dean would envelop you in his arms, as if he's trying to shield you from the world and its monstrosities. Everything about him will be warm - his embrace and the sweet words he whispers into your ear.
Dean will hug you a lot - it will be a constant reminder to him that you're alive and he still has you to protect.
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Sam Winchester:
Being a giant, you will almost disappear behind his arms - and you will disappear quite often. The majority of the women Sam has loved (though you yourself do not have to be a woman) have sadly passed away, brutally, so every moment he is in your presence, he will be touching you in some way - holding your hand, reaching out to brush your arms, and of course cuddling. His grip will be quite strong, but not enough to hurt you; he just doesn't want you to go away. He hopes that if he never leaves you, no one can get you.
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Castiel:
When Castiel has you in his embrace, his wings will be shielding you, though you may not know he does that. He will hold you as if you are a delicate china doll - and you are, compared to him. In those moments, when he looks at you, he looks into your soul - the very soul he has come to adore.
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Bobby Singer:
Three words. Papa bear hugs. :D (beautiful cinnamon roll, to good for this world, too pure)
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John Winchester:
Well, John Winchester is a pretty masculine man - the boys had to get their strong arms from someone (their mum lets be honest) along with their build (okay, that can be John). He'll hug you much like his sons would - never wanting to let go, in fear of losing you. Overall, hugs from the Winchesters will be warm and sweet, but that will only mask the desperation and fear that plagues them. Have fun with that...
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Chuck Shurley:
Chuck will cuddle with you while writing his books, finding comfort in knowing someone is there to love him and make him feel valid (which everyone is, by the way, no matter what you think - except maybe for people like Donald Trump, grr). He'll hug you tight in bed whenever he's having an especially gruesome dream about the Winchester brothers. You're his anchor in a wild sea, really - his everything outside of his destiny.
