AUTHOR NOTE: This was requested by wayward_anna.
You and the boys just finished a ghoul hunt and decided to go to a bar to relax. You even managed to talk a certain adorable blue-eyed angel into coming with you. You ordered a round of beers as you guys talked and goofed around.
"Let's play darts!" you suggested.
"Darts is kinda boring," Dean said, "what does the winner get?". You thought for a minute.
"The winner gets to kiss anyone in the bar they want," you said, "with permission of course,". Dean's face lit up.
"You're on!" he said.
"Will you play too Cas?" you asked the angel.
"I'm not sure how?" he admitted.
"I'll teach you," you said placing your hand on his, "please?". He smiled at your touch.
"Ok," he said getting up as you all headed for the dart board. Sam went first getting three darts on the bullseye.
"Awesome!" he shouted as Dean took his turn. Dean sulked as he only made two darts. You went up next and got 3 darts in. Finally, Cas stepped up and studied the dart board. You three stood there with your mouths opened as Cas hit the bullseye all six throws.
"Guess Cas wins," Sam says.
"Who are you gonna kiss?" Dean asked. Cas looked deep in thought for a minute then smiled as he looked at you. Your heart started to pound. He walked to you and softly lifted your head up as he leaned down.
"May I kiss you Y/N?" he asked. His warm breath fanning over your face. All you could do was nod. He softly pressed his lips to yours. It was soft and slow at first but soon turned into a deeper kiss that put his pizza man kiss to shame.