Blind Date - Winn Schott x Reader
Prompt: Winn confides in Kara about his fears of dieing alone, Kara gets an idea to set him up with one of her friends on a blind date. Little did she know the date went a little TOO well.
Type: Fluff with smut (italicized for your convenience) 18+ (if not skip the smut please)
Warning:Drunk Sex, Mentions of abuse
[Also I do put a specific appearance, you can change it if you like it’s not important]
[ALSO ALSO I know nothing about star wars so don’t judge me]
“My life is in danger every day, and I can’t help but to think that I’m gonna die one of these days and not have a relationship.” Winn vented to Kara, “Winn, your not going to die alone.” She said crossing her arms as he sighed. “It’s not like anyone would like me anyway.” He said as he lifted his Nerf gun and pointed at his monitor. An idea crosses Kara’s mind, her friend Y/n, who was a waitress at noonan’s, had been rambling about how she can never find a nice guy and all the guys are too masculine and she just wants a sensitive guy. Winn’s a sensitive guy, Y/n’s a nerd. It’s perfect. “Winn..” Kara said as he looked over. “How about I set you up on a blind date?” She said as Winn raised an eyebrow. “Sure!” He said excitedly as Kara smiled at his excited puppy look. “Okay, I’ll text you where to go but seriously I have to go.” Kara said as she stood up walking backwards Winn nodded. “Alright!”
“No Kara.” I said into the phone, a blind date? Was she crazy, only 43% of blind dates work out. Plus how did I know if it wasn’t some psychopath who was gonna kill me and eat my skin, or some stranger who doesn’t know what star wars is. I mean come on! “Kara, you know how I am with strangers.” She said as Kara laughed, SHE WAS LAUGHING, how dare she laugh at my social anxiety. “Y/n, trust me, you won’t wanna die and crawl into your shell by the end of this date.” Kara said as I groaned. “Fine, but if it sucks it’s your fault..” I said in a quiet voice. “Okay, so where is it and when. I have to get back to my shift.” I say reluctantly. “7, at Palmer's(idk go with it).” Kara said as I sighed. “Okay, fine.” I groan out as my boss yelled into the back room. “Y/n, get your ass out here. We’re slammed!” I nodded. “Yeah, okay! Sorry Kara, gotta go I’ll be there just make sure my blind date doesn’t flake.” I say hanging up the phone and putting it in the pocket of her apron as she walked out into the restaurant.
Y/n sat at a single table, the heel of her flats tapping against the floor. Her thumb flew to her mouth as she nervously bit her nail. Her long brown hair was twisted into curls and she wore a white top with a black skirt that hit above her knees, and her top had straps across her chest. She looked around quietly examining everyone, she didn’t know what he or she looked like and wanted to make a good impression so she dressed nicely, she had a glass of Merlot and apparently Kara had called in earlier and ordered for them.
She watched a nicely dressed man walk in looking around, seemingly just as nervous as her. He was cute, he had curly brown hair and a slight stubble and he wore a black button up and tie with dark jeans. She leaned over glancing at him when he noticed her he glanced at his phone and then back up at her walking over, she nervously adjusted her hair as he walked up. “Y/n?” He asked and she shyly nodded. “Yeah, are you Winn?” She asked and he nodded and released an awkward laugh that she smiled at, his laugh was adorable. He stood awkwardly until she pointed at his seat.
“You can sit.” She said as he looked over and laughed nodding. “Sorry, I’m not good with this whole date thing.” Winn said as Y/n giggled. “Me neither, don’t worry.” She said as Winn smiled, a waiter walked over holding two plates and sat down some sort of chicken dish that both Winn and Y/n looked at with confusion. “What would you like to drink?” He asked Winn as Winn glanced over to her cup seeing the red wine and looking back over. “The same as her, Merlot, I think.” Winn said with a smile as the Waiter nodded and walked off only to return with a wine glass holding the deep burgundy liquid. The waiter walked off as Y/n took a bite of the strange food and looked up to Winn. “It’s actually not that bad.” She said as Winn took a bite and nodded in agreement.
“Wait, wait. I’ve got another one!” Y/n said between her laughing as Winn chuckled along, they had been talking for a half an hour and were both very tipsy.
They had been telling bad jokes over and over again, before this they had discussed their interests and their lives. Turns out they have alot in common, they were both foster kids, they were both mega geeks, and when they talked about their dream partner they basically described each other without thinking. They had taken a minute and gotten serious and vulnerable, talking about how both of their parents were basically horrible people, since Winn’s dad was Toy man and Y/n’s dad walked out on her leaving an alcoholic mom and she basically got removed from the house and placed in foster care.
“What do you call five Siths piled on top of a light saber?” Y/n said giggling as Winn shrugged with a dopey smile. “A sith kebab.” Y/n said as Winn and Y/n giggled in sync as they both sipped on their drinks. “That one was bad.” Winn said as Y/n laughed with a knowing smile. “I know right!” She said as she placed her hand over Winn’s on the table with a smile, they had finished their food and the waiter walked over sitting down strawberries and a bowl of melted chocolate.
“I love those.” They said in sync and looked at each other and giggled which cause a snort to fall from Y/n’s lips making her blush and Winn smile admiring her adorkableness. Y/n grabbed a strawberry and dipped it in the chocolate, Winn did the same but Y/n placed it in her mouth and sucked all the chocolate off leaving the strawberry clean before biting it. Winn eyed her as she did his mind immediately went to naughty thoughts he should not be having on a first date with such a sweet girl, a quiet and involuntary groan falling from his mouth that he quickly followed with a cough, holy shit.
After they finished eating they payed, which they fought over but Y/n inevitably won, Winn swearing he would pay her back. They were both drunk and giggly as they exited the building talking among themselves. “So, uhm, I guess this is where we part ways.” Y/n slurred as she hailed a taxi. “Yeah, tonight was fun.” he said, a slur to his voice as well, as she nodded, there was a quiet tension that hung in the air. The taxi pulled up but Y/n didn’t get in she glanced at Winn. “You... uhm, wanna come over to my place and watch a movie?” Winn asked as Y/n nodded eagerly. “Yeah, sure!”
Y/n got in the car after Winn and she glanced over at Winn with a smile, it must have been the alcohol but right then she had never seen a more attractive man. The way he constantly had a content smile tugged onto his lips, his super kissable lips. She watched contently as his hand went through his hair. She let out a shaky sigh as he glanced over making eye contact, noticing she had been staring.
[For those who don’t like smut. Basically they kiss in the car, then go to her house and don’t watch a movie]
He examined her features as she did the same, in that moment there was nothing else to do. She leaned up pulling him by his tie and connecting their lips, leaving him in shock as he gasped lightly before his lips formed to hers and his hands landed on the back of her neck, hers resting on his chest as their lips molded together. She felt the car stop and pulled away both breathing heavily. She quickly scampered out of the car followed by Winn as she took his hand they entered the apartment building getting in the elevator as Winn pressed her against the wall his hand felt for the buttons instinctively pressing the button for his floor as their lips connected again, their eyes filled with passion, and lust.
Y/n lifted her hand and ran it through his hair as she pulled him closer sliding her tongue against his lip as he opened his mouth and their tongues met deepening the already intense make out session. The elevator dings and they separate, both breathing heavily as he holds her wrist pulling her to his apartment aggressively searching through his pockets pulling out her keys and opening the door throwing her bag onto his counter as she turned and slammed him into the door, her heels giving her the added height she needed as she kissed him deeply his hands felt for her waist as she held onto his tie firmly and they never parted as she backed toward his room feeling for the door handle quickly opening it as she pulled him back turning around and pushing him onto the bed, she had a new surge of confidence that Winn couldn’t help but admire as he sat on his elbows she leaned over kissing him again and sitting on his lap as her skirt flared up his hands ran up her thighs under her dress as she could feel the growing hard on in his jeans as she adjusted her hips he couldn’t help but release a groan at the added friction.
“P-please do that again.” Winn whined as she smiled and began to kiss on his neck as she grinded against him causing moan after moan to leave his mouth as she was breathing heavily against his neck, leaving small marks all over the sides of his neck. She disconnected from his neck as he began to untie his tie and she unbuttoned his shirt tossing it to the floor. He made quick work about her top pulling off the lose white garment. She ran her hands down his chest as his eyes gravitated toward her chest and she slid off his lap as she quickly worked on pulling off his jeans as she pulled them down she saw the large bulge in his boxers as she palmed it he panted lightly. She tugged on his boxers as she released his dick looking up at him with lust filled eyes as her hand wrapped around him she leaned forward pressing her tongue to the tip as his breathing quicked and he released a quiet moan. She smirked as she took him in her mouth, He leaned back onto his elbows as he moaned running his hands through his hair as his other hand reached over pulling back her hair as she sucked quickly.
Winn moaned loudly as he bit his lip. “Y/n” He let out a breathy moan as his hips bucked up slightly. “Y-you’re gonna make me cum.” He moaned out as she looked up at him with a smirk as she kept going his hips would buck occasionally, his fists curled into the blanket as he moaned her name loudly and came panting loudly as she looked up at him and swallowed causing him to gulp lightly as she leaned up to connect their lips again, crawling onto his lap as she pulled off her underwear tossing them behind her, the strap of her bra slipped down her shoulder as her skirt rested over her butt and she lifted her body over his lap taking a breath. “Y-you okay?” She asked as Winn nodded eagerly. She lowered her body down onto him as her head shot back releasing a moan as he kissed her neck, nibbling gently leaving marks all over her neck, just as she did him. She rolled her hips quickly as Winn looked unaware of where to put her hands. “You can.. you can touch me, you know.” She said breathlessly as he nodded and put one hand on her hip and the other reached up gently groping her breasts. The room filled with moans, pants, and quiet curses, as they moaned out each others names.
[I’m not good at smut I know lmao]
Winn woke up with a yawn as he went to move he realized his arms were wrapped around a person, he looked down and his heart stopped when he realized there was a naked woman beside him, her messy dark hair resting over her shoulders. He realized they were in his room and he slowly pulled away from around her as he quickly began to pull on some pajama pants as he walked into the bathroom noticing his chest and neck were covered in marks and lipstick as well as his own lips and most of his lower face were covered in the deep maroon lipstick as he heard a quiet mumble.
Y/n yawned as she sat up realizing she was wearing a skirt and bra she looked around to see her clothes strewn all over the carpet, wait, her room didn’t have carpet. She looked around as she heard a shower start her eyes darted to the door that was closed and had light coming from under it she stood up and looked around seeing another set of clothes thrown everywhere, her memories from the night before flooding back.
Y/n went to the extra bathroom washing her face of the makeup and seeing the hickeys all over her body as she had pulled on her underwear and a random shirt. She heard a knock at the apartment door and froze when she heard a familiar voice. “Hey Winn, you didn’t respond to my texts so Ijust wanted to make sure that your okay and the date went good.” She said as Y/n peaked into the hallway seeing Winn pulling on a button up and sipping his pants as he shook off his hair and glanced over seeing Y/n he pointed to his bedroom as she nodded and ran in he walked out and opened the door as his bedroom door closed quietly, Y/n began to get dressed in her clothes from the day before. “Hey Kara, yeah the date went grea-” He began but was cut off as she pointed to his neck. “Are those-” She started but as she looked up she could see Y/n pulling on clothes through the wall and released a loud groan. “Ugh, Winn! Seriously!” She said as Winn realized she could see Y/n. “Just, I’ll see you at work!” Winn said ushering her out of his apartment as Y/n stepped out sighing and straightening her hair. “I..I normally don’t do.. this.” She said pointing to herself and him. “I’m not like that.” She said as Winn nodded. “Yeah me neither.” Winn said quickly as they stood awkwardly. “I had a nice time last night.” Y/n mumbled as Winn nodded. “yeah.” Winn said as Y/n smiled lightly. “I have to go, but I did put my number on your phone.” She said as she walked to the door grabbing her bag. “I’ll text you.” Winn said as they smiled at each other. “Alrighty.” She said walking out with a smile.
