I feel Dean would be kind of rough with Jack and the next one I'd feel to do would have Dean being spanked by Cas for being too rough/mean/rude.

I recently lost my job and I'm looking for really simple commissions, similar to this. 2 characters, no background, simple outfits. If you don't want a picture, and just want to help out, send to paypal.me/nenechama anything helps!