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The hunt was over and you, Sam and Dean were having beers and burgers at a local dive bar and grill. It was just a typical Wednesday the three of you – hunt some vamps, ghouls, or demons, have a few beers that would later turn into shots of whiskey. But tonight before the shots of whiskey, Sam had his eye on the cute waitress.
You and Dean sat at the table, plates and empty beer glasses removed and watched Sam shamelessly flirt with the blond. Two shots of whiskey were served to you by another equally attractive waitress who tried to make eye contact with Dean but he didn’t bite. You clinked your glasses and shot the fiery liquid down your throats.
“He doesn’t stand a chance with that one,” Dean commented as he washed the whiskey down with the last few swallows of a beer. The waitress toss her head back and laughed a little too loudly at Sam’s joke. She put her arm on his bicep.
“You’re wrong, Dean. She’s going to hit a homerun with him.” The waitress sucked on her index finger engrossed in every word Sam said.
“Wait, you think she is putting the moves on Sammy?” The two of you watched as she removed her apron and she and Sam left the building.
“Bet you her bra and panties match,” you spat out with a little more venom than necessary. Dean gave you a look.
“Bras and panties always match,” he said finishing off the beer Sam had left.
“Always?” you asked and Dean nodded. “Winchester, you are such an idiot. If the bra and panties match, you weren’t the one who decided to have sex.” You threw some bills on the table and stood up ready to get some sleep.
“Are you saying every time a woman matches her underwear it’s because she wants to have sex?” You collapsed into the Impala taking shotgun for once.
“Not every time. Sometimes they match because of dumb luck.”
“Hmmm. I didn’t know that. I thought it was a chick thing. Wait, what color are you wearing?” Dean slurred just a bit. He probably shouldn’t be driving but the motel was only a few blocks away.
The whiskey had warmed your body and your face was flushed. You and Dean had a few hot and heavy make out sessions in the past but the two of you had never had sex. Actually you hadn’t made it past second base. And it had nothing to do with Dean. He was an amazing kisser that got you wet just thinking about it. It was you. You had always pulled away often with no explanation. Dean never asked for one or pushed you to have sex. But right now, you were in a very friendly mood. “Who says I’m wearing any underwear?” You smiled at Dean and winked. He pealed out of the almost empty parking lot and raced back to the motel.
You walked into the dark room and before you could turn on a light Dean had you pinned against the door. His mouth covered yours and tongue tasted like whisky and beer. His lips moved to your ear and he nibbled. “I want you,” he breathed. More kisses down your neck and then back to your ear. “I need you.” Every fiber of your being was on fire. This had to happen and it had to happen NOW. His hand pulled the hem of your t-shirt over your head and looked at you.
“Black bra,” he smiled. The neon sign with the hotel’s name was right outside the window and gave the room an eerie red glow. “Does that mean…” He knelt in front of you and unzipped your jeans. “Black panties. You lied to me Y/N. You’re a naughty girl.” Your grin was pure evil. He removed your boots and socks and all of your clothes except for your underwear lay in a pile next to you.
“You’re wearing too many clothes, Winchester,” and proceeded to remove the flannel shirt, t-shirt, and jeans as you made your way to the bed. He was on top of you in a heartbeat kissing down your body. You felt so alive and happy for the first time in months. And then reality hit.
“We can’t do this.” You felt a little sick saying those words.
“No, baby, we can,” Dean said as he continued to kiss your stomach. “It’s all good. I’ve got plenty of condoms and Sam won’t be back until the morning.” He was about to remove your panties and you were panicking. This isn’t happening, you thought. But it was. You couldn’t do this to him. He was too good a person, too important to the world.
“Dean stop!” He looked at you with swollen lips and a single tear fell from your left eye. “I can’t do this.”
“Why not?” he whispered. “Are you a virgin?” You laughed and forced Dean off of you. You curled into a ball your back to him ashamed that you were crying. Horrified that he was going to find out your deepest secret. He rubbed your arm.
“Y/N, what is it? I like you. I’m pretty sure you like me. I like sex… Is that it? You don’t like sex?” You could say yes and avoid telling him the truth but you and Dean had been fooling around for months. It was time to piss or get off the pot.
You took a deep breath. “I’m not a virgin and I do like sex. Well, I use to…” your voice trailed off.
“Did someone hurt you?” Dean asked. He whispered but there was a firm I’ll-kill-the-son-of-a-bitch tone in his voice.
“Have I been raped? No.” You sat up and Dean took you into his arms. He held you close against his warm body. “Do you remember about six months ago I went on that wendigo hunt alone?”
“Um hmh,” he held the hug so you wouldn’t have to face him. You won’t see the disappointment in eyes.
“I hooked up with a guy I met at a bar and he seemed like a nice guy. We had sex and that was that. I left and went to the next job. About two weeks later, I noticed I had some sores…” Dean leaned back and wiped away the cascade of tears falling down your face. “He gave me herpes.”
Dean sighed loudly. “Herpes?” he asked. You nodded full of embarrassment. He pulled your chin up. When you looked into his eyes pools of tears were forming. “I thought you were going to say you had …” He hugged you. “Herpes aren’t a big deal.”
“It is a big fucking deal!” you yelled and pulled away. “I am ruined!”
“You’re not ruined! What are you talking about? You just have to be extra careful.”
You stood up and went to the bathroom to blow your nose. “Dean, no man will ever want me! Jesus, even with a condom I can give this to someone! I couldn’t live with myself if I did that!”
Dean sat on the edge of the bed. “Come here, Y/N.” You sat next to him and he took your hand in his. “Are you on meds?”
“The doctor said to only take them if I have an outbreak.”
“Are you having an outbreak right now?”
“No but you can’t always tell…” You put your head in your hands. “You think I’m an idiot.”
“I would never think you were an idiot. It happens. It happens a lot more than you think. I’m not exactly a poster child for safe behavior.”
“Do you have herpes?” you snapped.
“Not that I know of. Y/N, I think you’re beautiful and amazing and a bad ass hunter and herpes or not, I still want to have sex with you.”
“But what if….” He shushed you.
“You can’t ‘what if’ life. I’ve stared down the apocalypse and have been to hell and back – literally. Do you think herpes scares me? I just want to be with you.” He ran his fingers over your cheek.
“I’m scared.”
“Don’t be.” Dean took you face in his hands and kissed you. “I will take care of you. Always.”