A/N: Written for supernaturalimagine on Tumblr. First attempt at "reader-insert", aka second person narrative. I'm trying to practice my 2nd-person narratives, so I'm hoping to get some good criticism from my fellow writers here.
You looked at yourself in the mirror and sighed turning away. The emerald green formal dress was laying on your bed, staring you down. You could hear Sam, Cas and Dean elsewhere in the bunker, preparing themselves for the night.
You were going undercover at a charity gala in order to keep tabs on someone you suspected was a werewolf. The gala was about 3 hours from Lawrence and you knew you needed to leave soon or you'd risk losing the trail of the young woman.
You looked at the dress again. You had never worn a dress in your life. You weren't exactly the type of girl who went to dances or even out on dates. You never had the chance to go to prom, considering you joined up with the Winchesters and Castiel 3 weeks before senior prom when they exorcised a demon out of your best friend. You were already a hunter, but you never noticed the signs that she was possessed. After that, you just joined the guys, keeping them from killing each other and making sure they ate more than just fast foods.
You always thought the job was going to be knife fights, fake IDs, pant suits and leather jackets. You were not expecting to have to go shopping with Sam for a formal dress and matching heels for a freaking case. You sighed and pushed your hair out of your face. Dean told you that if you came out in a ponytail he'd chop all your hair off, so you curled it and pinned it back so the ringlets fell down your shoulders. You looked at the dress and 3 inch silver heels and grumbled. If that werewolf tried to run you were going to be no help. You wouldn't be able to run in heels or in an almost-to-the-floor gown. And concealing a weapon in a skin-tight dress without a bra was going to be impossible. Your only defense tonight was going to be a silver blade concealed in your clutch.
You sigh and put the heels on first before slipping the dress over your head. You straighten the dress and fix your hair as Dean knocks on your door.
"Come on, (y/n). If we don't leave soon we'll miss the event and we can't let this thing get away." You glared at the door.
"I'll be out in a minute, Dean. I'm just finishing up my make-up," you respond as you hastily apply some light makeup, including some light shimmering lipgloss. You check your clutch to make sure you grabbed your knife and you open your door, flicking off the light.
Your heels tap on the cold floor as your freshly manicured toes slowly freeze. You come around the corner and into the main room where the three guys are sitting around waiting.
"Alright, I guess I'm as ready as I'll ever be. Let's do this." At the sound of your voice, all three men turned to face you, Cas and Sam immediately rising from their seats and straightening their suits. They all stare at you and you can feel their eyes raking over you.
"You look...wow," Sam says, almost entirely speechless. You can see a light blush fill his cheeks.
"You look more beautiful than any of the angels I've ever met in Heaven, (y/n). You would put them to shame with your beauty." Castiel walks over to you and lightly kisses your hand, bowing. This time, you blush and your eyes flash to Dean's.
"Well? Do I look convincing enough to pass for a socialite, Mr. Winchester?" In order to get in, Dean was acting as my date while Cas and Sam got in as waiters. Dean's green eyes scanned over me again and he took my hand.
"You, my darling, are the most beautiful thing I've ever seen. You'll be the best dressed young lady there, I promise." He lightly kissed my cheek and picked up his car keys. "Let's go kill a werewolf." With that, you all headed out to the Impala, prepared for the covert operation and for what might lead to a kill.