Plot: You and Stefan dated for a while in high school, but like most
high school relationships, college got in the way. You wanted to move
away and Stefan couldn’t find the strength to let go of his life and
home in Mystic Falls. So you two decided to break up. You left to college in Boston and Stefan stayed in
Mystic Falls. Now, almost six years later, you’re both invited to Bonnie
and Kol’s wedding. It’s the first time you two are seeing each other
since the break up. That’s not the case with some of your other friends, however.
Pairing: Stefan x Reader, Klaus x Reader, Matt x Rebekah, Kol x Bonnie, Damon x Elena, Caroline x Enzo, Elijah x Hayley (not mentioned in this chapter)
A/N: HI!!!! okay so just a heads-up that the italics are a flashback and purely smut. I thought I wanted the reader to end up with Stefan in this, but idk anymore. I will say, however, that you will see smut from both Nik and Stefan in this fic. Some flashbacks and some current. please let me know what you think!! (gifs aren’t mine!!)
As soon as Stefan walks away, you shake your head and pour yourself a glass of bourbon. You swirl the glass around, staring at it until you hear Elena and Caroline’s voices. You turn to face them, raising a glass as Caroline places her hands on her hips.
“Y/N! The clipboard,” she huffs, walking over to you with said clipboard in hand. “I’ve made hotel arrangements, I just need you to pick who you’ll be sharing a room with.”
“Let me guess, you’ve made me a list of all possible roommates, huh?” You grab the clipboard and Caroline nods, smiling.
“Ah, good,” you hear a deep British voice and look up to see Enzo walking over to you two. “Now that you’re here, Y/N, my girlfriend and I can spend sometime alone.”
“Hey to you too, ass,” you narrow your eyes at him as he smiles and wraps his arms tightly around you.
“You know I’m happy you’re here. And not just because Caroline can take a break now,” he pulls away and winks at you, intertwining his fingers with Care’s.
“Yeah, yeah. You two deserve some alone time. Caroline, go. I’ll figure things out here, I promise. Besides, I’m sure you’ve sent me at least a dozen emails containing proper instructions.” To prove your point and insure that Caroline doesn’t protest, you pull out your phone and show Caroline all 15 emails that you’d received in regards to the wedding.
“Thank you, Y/N,” Caroline sighs, shaking her head and smiling at you and Enzo. “I know you just got here, and I’m sorry. Thank you for doing this. I owe you!”
“Just remind me not to hire you as my wedding planner if the time ever rolls around,” you chuckle and push Caroline and Enzo away from the bar.
“I will be your wedding planner and you will get married and–oof okay fine we’re leaving!” She pulled Enzo into a bedroom and you smile, looking at the clipboard.
“Y/N!” Of course before you can get any work done, you’re already smothered in a hug by the one and only Damon Salvatore.
“Damon!” You try to move your arms so he could hug you, but he’s got a bone-crushing grip on you. “Please I am human do not break me.”
“Oh, crap! Sorry!” He quickly lets you go and you take a deep breath, pressing your hands against your ribs. “I’m just excited to see you! Are you okay?”
“Yeah, yeah. I’m okay, don’t worry,” you groan and stretch, cracking your neck as Damon gives you a wierd look. “Stop that, my neck was in a wierd position for like three hours! Airplane seats aren’t as comfy as you think.”
“How’s Massachusetts treating you?” You two start walking back to the bar and Damon wraps an arm around your shoulder.
“Undergrad was fun, more than one would think. Law School wasn’t bad either, to be honest. I finished the program a few months ago. How’ve things been here?” You grab your bourbon as Damon reaches around the bar to pour himself a glass.
“It’s been wierd. I’ve been alive for over a century, but I finally feel at home here and now,” he looks towards the living room and you follow his gaze: all your friends laughing and teasing one another while planning on of your weddings.
“I’ve missed this,” you whisper, eyes resting on Stefan’s figure for a second longer than necessary all the while hoping that Damon wouldn’t notice.
“What was that?” Damon, of course noticed.
“That was nostalgia, Damon. Hopefully the last of it,” you down your bourbon and look at the clipboard in your hand. “I’ve got a wedding to plan, so please–”
“Y/N!!!” You hear a pair of voices call out your name, music to your ears.
“Matt, Beks!!!!” You hold your arms out for your favorite couple, missing them more than you’d care to admit.
“We’ve missed you so much,” Matt, of course, wraps his arms around you first, squeezing you and kissing your head.
“We really have, things haven’t been the same,” Rebekah places her head against your chest as you wrap your arms around her shoulders.
“Aw I’ve missed you too, babies,” you kiss Rebekah’s head and Matt smiles at the two of you.
“My two favorite ladies! I’m so–”
“Excuse me, Donovan?” A very threatening whispers comes from behind Matt and you recognize the voice as the bride’s.
“Not including you, of course, Bon! Come on!” Matt stuttered as he tried to clear himself out of the hole he’d just dug. Meanwhile, Rebekah lets you go and you meet Bonnie’s eyes.
“Come on, he hasn’t seen me in years. I think it’s okay if he likes me a little more,” you laugh as Bonnie glares at you. “COME HERE!”
You and Bonnie quickly wrap your arms around one another, squeezing each other and whispering thank and ‘i love you’s.
“I can’t believe you’re getting married!” You squeal as Bonnie laughs, holding her hand out to show you the ring.
“Yeah, well, Kol is very–”
“Sexy? Handsome? Good at making love?” Kol steps in next to Bonnie, a cocky smirk on his face.
“I was actually gonna go with persistent, but sure baby,” Bonnie boops his nose. “Whatever makes you happy.”
You laugh and Kol hugs you from the side, pouting at Bonnie as she shakes her head, smiling.
“Bonnie’s being mean to me,” he sticks his tongue out at her and you shake your head.
“Are you sure it’s a good idea for you to get married to him, Bonnie? Child marriages are a terrible idea,” you whisper loudly, hand covering the side of your face that Kol could see. Everyone erupts in laughter and Kol groans.
“I forgot you two were best friends! You’re supposed to be on my side,” Kol gently nudges your shoulder and you smile up at him.
“I’ll always be on your side, loser. I’m glad you two are getting married!” You squeal and give him a tight hug, pulling away to smile at him and Bonnie. “So happy for you two!”
“We’re so glad you’re here,” Kol smiles at you and walks over to Bonnie, wrapping an arm around her waist and kissing her temple.
“I’m happy to be here. Now, you two have a cake testing in half an hour and I have to look over hotel arrangements and say hi to all the other losers,” you rub Bonnie’s shoulder as she smiles up at Kol. “Also, there’s no way you two lovebirds are going there alone. We’re on a tight schedule.”
“Y/N, we’ll be fine! We’re not teenagers, come on!”
“Sure you’re not, Kol. Tell your hormones that,” you brush him off and look around for a responsible adult. “Elijah! Stefan! Stefan’s girlfriend! Gather round.”
All three of them walk over to you with tired expressions, not that you care exactly.
“Alright, Bonnie and Kol have to go taste testing, but I don’t trust them alone simply because we’ve got a tight schedule that we have to follow if we want me to live. That being said, I need you three,” you point at Elijah, Stefan, and Stefan’s girlfriend individually. “I need you three to chaperone. Got it?”
“Um, sure. Who are you?” Stefan’s girlfriend speaks up and you turn to look at her.
“Your worst nightmare if anything goes wrong today. Your regular nightmare if you don’t fuck things up. Call me Y/N,” you give her a sweet smile as Damon, Matt, and Rebekah try not to laugh. “Now off you go, everyone!”
You shoo them away, Stefan’s face hardened after your interaction with his girlfriend.
“God, I’m so fucking glad you’re back,” Damon laughs as Matt and Rebekah agree .
“Matt, Beks, I need you to pick up Hayley and Hope, Marcel, Cami, Freya, and Davina from the airport.They should all arrive within 15/20 minutes of one another. The first one lands in half an hour, so get going!” You hand them a sheet with all arrival times, terminal and gate numbers, and hotel arrangements if needed.
“Perfect. See you guys!” Bekah and Matt grab everything and head out.
“So, anything for me to do?” Damon asks and you look at the crowd, only to find Kai and Alaric arguing rather animatedly about party treats while Elena tried to stop them.
“Yeah, you keep an eye on them. Make sure the idea for the party treats is figured out by tonight. We need decorations ready tonight, too. The color theme is yellow and egghsell white with hints of light green so please get me something by tonight,” you give Damon a look and he nods, finishing up his bourbon.
“One daddy coming right up,” he smirks and walks over to the group as you groan.
You place the clipboard on the bar and eye it, taking a look at everything that needed to be done tonight. Then taking a look at everyone’s hotel arrangements, the times, the baggage. You pour yourself another drink, hoping the jetlag doesn’t catch up with you.
“Need some help, love?” Klaus asks, sitting on the stool next to yours.
“I just need to relax, but I know that I can’t with this wedding coming up,” you swirl your cup and look over to Klaus.
“I can definitely help with that,” he whispers, letting his eyes rest on your lips, and you shake your head, trying not to think of that night.
“Klaus, come on,” you chuckle and look back at the clipboard, hoping he leaves it alone.
“I’m just trying to help, love,” he whispers, his fingers tilting your head to face him.
“Help me some other time,” you bring your lips closer to his and press them against the side of his mouth. He still for a moment as you turn back to the clipboard, trying your hardest not to think of that one night in particular with Klaus.
You’d spent plenty nights with him before. He was one of the few people from back home that you’d actively try to see, the only one who could take your mind off things. This time was different though, this time, he reached out to you. He wanted to see you, wanted you to help him forget. He said he’d surprise you one of these days.
Normally with you two, everything happened fast. A rush of teeth against flesh, nails raking down one another’s sides and back, a primal need to have the other succumb to your will.
That time in particular, Klaus tied you up. You two had never done this before, but you always wanted to try it with him.
“Does my baby girl have some rope?” Klaus cupped your face, gently tilting your head up.
“Y-yes, she does, sir,” you whispered and turned away, grabbing some rope from your closet.
“Good girl,” he whispered, brushing his nose against yours. “Now Sir needs you to strip yourself of everything but your panties and spread out on the bed, okay?”
“Yes, sir,” you turned away, blushing wildly as you obliged. You spread yourself out on the bed and his eyes ravaged you before the rest of him could. You shifted under his gaze, more aroused and more insecure by the second.
“Nuh-uh, love,” he tsked, shaking his head at you as he walked closer and removed his tie. “Sir loves looking at you. He loves seeing a slight tremor pass through you every time I rake my eyes up and down your beautiful body. He loves seeing your nipples perk up the longer they’re left unattended. He loves that beautiful pussy of yours, god that is breathtaking.”
You whimpered as Klaus stopped at the edge of the bed, lowering himself so that his nose was barely brushing against your clothed slit. You begin to move and before you can do so, Klaus raised his eyebrows at you and you stop immediately.
“If baby girl wants my mouth on her, she has to play by Sir’s rules. Okay?” He whispered, gently placing a finger against your panty-covered opening.
“Oh, y-yes si-sir,” you groaned softly and bit your lip as Klaus teased you.
“There’s my good girl,” he whispered, his tone huskier now as his eyes flash golden. “Sir is going to tie up your wrists, okay? The safeword will be watermelon.”
“Yes, sir,” you nodded, eager to have Klaus’s hands all over you. You’d thought about this for a while now.
“Hold your wrists out for Sir,” Klaus climbed on top of the bed and straddled your waist while you lifted your arms to him. He smiled and wrapped the rope around your wrists, eyes growing hungrier by the second. His eyes trailed up and down your body, clearly loving how you looked tied up. The longer he went without touching you, the more impatient you became.
“Are you going to touch me or are you just going to keep staring at me, huh?” Before you could think, the words spilled out of your mouth and you could feel the air around you still. You could feel the change in Klaus’s demeanor. He was never going to touch you now.
“What is one thing that Sir asks of you, the only thing that I ask of you?” He growled out, removing himself from on top of you.
“S-sir asks me to be patient and not speak until spoken to,” you whimpered and looked down, ashamed that you’d broken his one rule.
“And yet you do the exact opposite,” he glared at you, sitting at the edge of your bed and pulling you up towards him. “How many times do you think Sir should spank you for disobeying him?”
“F-five?” You whispered, still unable to look at him. You’d never gotten spanked more than five times.
“Wrong answer. I was thinking more along the lines of 10,” he breathed against your lips as you gasped, finally meeting his gaze. “I want you to count each one, okay?”
“Y-yes,” you couldn’t look up at him, you could barely speak without your voice breaking.
Klaus pulled you over his lap, gently rubbing your panty-covered ass.
“Sir really likes these panties,” he pressed his lips against your back before speaking again. “He would’ve loved to rip these off with his mouth.”
You wanted to beg him to touch you, to bite you, but you knew that would only make this situation worse. So you stayed quiet as Klaus continued to press soft kisses along your backside, once on each cheek and then moving lower.
“Sir loves your filthy little pussy, you know that?” His lips brushed against your lower set and you couldn’t help but whimper at even the slightest touch.
“You’ve been a bad girl. Sir won’t eat you out yet,” he nuzzled his cheek against your ass as his fingers made their way up your thighs and to your panties. “His fingers, however, will give you a wild orgasm. You’ll feel each slap even more after I finger-fuck your wet pussy.”
You couldn’t help but to groan at his words and at his hands. His fingers stayed outside your panties but the fabric somehow added friction with each touch. He held your hip with one hand while the other teased you. He pressed one slender finger against where he knew was your eager opening. You moaned loudly and he did it again, this time pushing the finger and the cloth deeper in you.
“Who knew having your panties on made you even more vulnerable?” Klaus growled as he used his thumb to tease your swollen clit. He leaned down to lick a small strip over your panties, from your opening to your clit. That way, the cloth was more flexible. He bent both it and me to his will. His thumb worked tirelessly against my clit as he brought forth another finger and quickly rammed it against my panties, the thickness of his fingers wrapped inside the cloth made me shake.
“Oh, that’s it. You’re getting closer, aren’t you?” He bit your thigh, careful not to sink his teeth into you.
His fingers swiftly removed the cloth and found their places against your pussy. His thumb was pressed against your clit, not moving and not letting you move. Meanwhile, his fingers quickly rammed in and out of you, your walls clenching around them as he grew merciless. You screamed his name, barely yelling out a warning as you came all over his fingers and your panties. He chuckled lowly, wiping his fingers against your panties and pulling them back up against you.
Before you can come down from your high, you feel Klaus’s palm make contact with your ass. Over and over and over. 10 times over to be exact. You knew because you counted. You knew because Klaus apologized and made you cum 10 times after that to prove his guilt. You, of course, didn’t mind the spanking, but you wouldn’t tell him that for a while.
“Hello? Earth to Y/N?” A hand waving in front of your face pulls you out of your rather embarrassing thoughts.
“Yes?” You clear your throat and turn to face Jeremy, completely ignoring Klaus’s rugged smirk to your side.
“First of all, I’m so fucking glad you’re back. These people are all crazy,” he pulls you into a hug and you laugh, realizing how much you’d miss this annoying kid.
“Second of all,” he pulls away and smiles widely at you. “Kai and I don’t know who we’re rooming with. I don’t think anyone else does either.”
“Oh, right. Well,” you clear your throat and grab the clipboard, flipping through the pages until you find one titled hotel arrangements. “It says here that are couples are rooming together; Bonnie and Kol will be staying in separate, larger suites; everyone else will get paired off and one lucky trio will get a larger room but will have to band together.”
Everyone nodded, seeing as it made sense thanks to Caroline.
“Now let’s see. It says here that the Saltzmans are all in one huge room. Elijah, Hayley, and Hope are in one room. Matt and Beks, Davina and Cami, Stefan and Ivy? So that’s her name, hm,” you shrug and continue reading the list to those present. “Damon and Elena. Caroline and Enzo. Tyler and Liv. Freya and Luke. Kai, Marcel, and Jeremy. And that leaves me with Klaus. Any questions?”
You look up to see the others have poured in as well: cake testing is over and Matt and Beks are back from the airport with all the folks.
“Yes,” Kai pipes up, looking rather concerned. “Does that trio room have three beds because I refuse to share one with dirty Jeremy over here.”
“No, Kai. You all have share one King bed. We’re making a porno,” you shake your head and Kai’s eyes grow wide. “I’m kidding Kai. Three separate Queen beds for three sassy queens. Any other questions?”
“Yes, why are you sharing a room with Klaus?” Stefan’s eyes meet yours and you do all you can not to walk over there and punch him.
“I didn’t want to be part of a lucky trio and Klaus is one of my best friends. Now, any questions that concern you?” You roll your eyes at him and Stefan shakes his head.
“Yes,” Ivy pipes up and by now you’re fuming. “Who are you, seriously?”
Requests: “A dirty truth or dare smut with Klaus, Elijah, Damon, Matt, Stefan, Jeremy, Enzo and Kai!! The reader is the only girl there x”
Damon always insisted on playing a good game of truth or dare when you visited his house. The dares and truths would be harmless. But this time was different, normally it was just you, Damon, Stefan and Enzo. Damon invited Elijah, Klaus, Matt, Jeremy, and Kai to play and hang out with you. You had hung out with this group before, but only with other females. You were the only female in a room full of hormonal men.
It would be strange, but it could be fun. There were snacks set up on the coffee table and Damon had spent the whole morning moving the furniture around in the den to get the multiple sofas facing each other. “Y/N! You made it!” Damon cheered and put his hands on his hips. You looked around the den where Klaus and Kai were smirking at you and Enzo licked his lips. “Stef is in the kitchen grabbing the drinks. How about a friendly game of Truth or Dare?” He asked the guests. Matt and Jeremy nudged each other and you sighed. “Great, I’ll grab the snacks.”