Disclaimer: I don't own any of the Gossip Girl Universe outside of any original characters, concepts, or locations not seen in the actual books or TV show.
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Spotted. Mystery Boy. He isn't much of a mystery anymore. Though a lot of details are still missing to even me. Looks like several of St. Jude's more handsome students and alum's have been in his company. First C and N, now this? Why do I have a feeling that this will end in shirts vs. skins? I'll root for your Harem of Hotties any day K. Just name the time and the place and your team will have a legion of followers.
Sign me up!
XOXO, Gossip Girl
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Kennedy slept away as much of Friday as he could. School was starting on Monday. Connor and the others had already had a week of college classes under their belts. Tonight he would be meeting the Windsor's. It had been quite a while since he had touched alcohol, and Kennedy was really beginning to regret it.
'Charlie's always been a bad influence on me,' he thought to himself as he kicked himself out of his warm cocoon of Italian sheets and down pillows.
A quick glance at his alarm clock showed him that he still had some time before the impending meeting. A ring of his phone told him that he had a new message… And it was from Gossip Girl? Well it wasn't to him personally, but it did involve him unfortunately.
'I so don't need this right before school starts.' Kennedy discarded his phone as he gathered a fresh change of clothes. 'Why are they letting their lives be tormented by some jealous stalker/bully?'
He left his room for the bathroom only to remember that he had forgotten a towel. The sound of his ringtone chirping once more notified him of another incoming (text) message.
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Lay low this weekend. She'll have her next target soon enough -Charlie
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Kennedy could only smirk. Charlie was still in there after all these years. Beneath the expensive clothes and scathing words was the friend Kennedy could still recall from years ago. Sure the Chuck persona was a bit much, but he was beginning to see why his friend had changed the way that he had… So it took a bit of self-restraint to not include Charlie in the text despite Chuck using the nickname himself.
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Don't worry Chuck. Spending the weekend with one of my Minders. None of her followers will get a shot of me.
-Kennedy
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Our friend could only wait in anticipation of a response. It didn't take that long for it to happen. Kennedy picked at his fingernails in boredom while waiting. Sometimes he had the patience of a saint while he had the emotional span of a teaspoon at other times. Right now he was leaning more toward the latter.
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Minder? Is there something you're not telling me? And I told you before Charlie is fine when it's just us.
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Kennedy sighed as he typed a response.
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One of my 'babysitters.' Thats a story for another time... And now is a good time as ever to practicing calling you Chuck, Chuck.
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He could only image how Chuck would respond. Things were so different from the way they once were, but Chuck was still the same deep down. His façade may have been upgraded and tweaked beyond recognition, but the same insecure, adventurous, and closed off boy remained deep down in that shell of a womanizer somewhere.
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If you say so.
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The dark haired teen let out a big sigh. That response was far too short and the length was the least of his problems. This was really cutting into his shower time. So much for his shower right? Kennedy took a quick whiff of himself and made a funny face. He knew he desperately needed a shower stat but the question was how to wrap it up with Chuck quickly without being rude and cutting his friend off.
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Weren't you paying attention to me in the limo Chuck?
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Kind of… Was more glad to have you back to be honest.
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Kennedy smiled. It felt good to have the feeling being mutual. Chuck was much cooler than the warm Charlie he encountered years ago, but he was glad for the distance to be honest. Kennedy needed space and Chuck was going to do that to keep up his persona.
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Good to know. I have to run. But my minders are paid to make sure I check in and stay out of trouble. Basically glorified help.
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Chuck never texted back, so Kennedy took that as a sign of acknowledgement. The obligatory 'ok and have fun' was unnecessary and unwanted to be honest. The teen stripped off his remaining articles of clothing, threw them in the hamper, and turned on the shower. He looked at himself in the mirror noticing how much he had changed already. A new haircut, clearer skin, and whiter teeth were a few of the things
Kennedy still felt like he was walking on eggshells with all of these Upper East Siders, but he was beginning to get the hang of things. Or at least he hoped that he was… A weekend with Connor and his family was exactly what he needed. He just hoped to God that they weren't too WASPy. Connor seemed decent but you never know.
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Connor showed up at five o'clock exactly in a navy blue button down, powder blue tie, and navy slacks. Kennedy had spent a lot of time fussing with his hair and deciding on what to wear. He wanted to impress the older athlete's parents. The blonde hadn't mentioned much about his family to be honest, Kennedy wasn't sure whether it was to seem more down to earth or it completely slipped his mind. In fact Kennedy was going into the situation completely blind.
"Not going to try to back out now are you?" Connor said ruffling Kennedy's hair.
"Dude!"
"Sorry, but your hair looked too perfect." Connor laughed at his friend's pout. "Only mine is allowed to be that close to perfection."
Kennedy remained quiet for a moment as he let his anger subside. During that moment Connor mentally sized up Kennedy's appearance and had to admit that his younger friend cleaned up well when he put the effort in. Kennedy was wearing a light blue button down, gray slacks, and a navy tie. "We're like twins!"
The Boston native could only roll his eyes.
"Anything I should know before hand?"
"Dad's an architect. Mom's into design."
"Match made in retail heaven."
"Very funny K." Connor shook his head. "We better get going."
"Sure thing."
The duo exited the apartment quickly. Connor grabbed the bag Kennedy had packed for the weekend.
"Thanks again dude for well you know, everything."
"No problem bro. You've become like a little brother to me in the short time we've known each other so you might as well meet the rest of my family. You'll be calling them Mom and Dad in no time!"
Kennedy stopped walking toward the elevator as the comment sunk in.
"Come on bro, don't cry now."
"I wasn't going to," Kennedy huffed as he wiped away the beginnings of tears from his eyes when Connor wasn't looking.
Connor showed his million dollar smile once more. "Sure, just let me know if things get awkward. Dad knows a little bit, but not much. And Mom is intense to say the least."
"Thanks for being vague. That was so enlightening."
"I try," Connor said gesturing Kennedy to enter the elevator first as the doors opened. "After you."
"Don't push it."
"The button or my luck?" Connor said before the duo erupted in a fit of laughter.
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The duo took Connor's silver BMW convertible for a bit of a ride as the blonde maneuvered around the streets of New York.
"Shouldn't we be heading the other way?" Kennedy asked confused as they drove further away from the Upper East Side.
"My parents decided we're going to meet upstate tonight at the Cabin."
Kennedy could only imagine what their definition of a cabin was.
"Catch some shut eye, I imagine you'd need some after your LONG night with Chuck Bass," Connor said with a smirk as they got onto the highway.
Kennedy smacked his friend on the arm. "It wasn't like that… we kind of go back... We kind of caught up with each other last night."
"I won't pry any more. If that's what floats your boat I'll support you until something goes wrong. And I'll make sure after that we get you tested for every disease under the sun."
"That's very reassuring."
"I try Bro. Just be careful Kennedy, this isn't Boston. It's war in stilettos and blazers."
"Just what I need, even more anxiety about starting on Monday."
"Well I don't have any Xanax or weed so you'll have to make do with my mom's cookies," Connor said grabbing a tin from the back seat.
"Keep your hands on the wheel dude, kind of don't want to die now that this is beginning to get good," Kennedy said nibbling on a sugar cookie.
Connor was right, they were THAT good… So good in fact Connor nearly swerved off the road when Kennedy later smacked his hand away when the blonde attempted to relieve the teen of the tin on some windy road
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The duo arrived at "the Cabin" about three hours later. It was surprisingly modest compared to what he had expected, not that he was expecting anything simple considering who the Windsor's and what he had learned about them from an extensive use of Google.
"Take a deep breath dude, it's going to be intense."
"Meeting your parents or discussing IT?"
"Both, I'm not sure which is going to scare you more!" Connor said putting an arm around Kennedy's neck. "But don't worry I've got your back Bro!"
"Thanks Bro!"
The two did several friendly punches and other exchanges of machismo before speaking once more. They weren't at the point to me be all emotional and touchy feely.
"You may annoy me like a pesky little brother, but you're useful to me."
"You mean if I dyed my hair I would be useful for your love life."
Connor pretended to have been stabbed in the heart. The dramatics did little to help his case.
"That hurt bro."
"I try, but for some reason I feel like doing it again and again."
"Smart ass."
"I know you are."
"Seriously Kennedy?" Connor glared harshly which made the black haired male actually feel guilty and put his head down to look at the ground.
"Sorry."
"Feel better?" Connor said lifting Kennedy's head up.
"Yeah jackass, though this emotional roller coaster thing isn't as fun as I thought it would be. How it works is beyond me."
"It works all the time though."
"Still doesn't make it a good idea."
"I got you to relax. Just chill and stop talking before we say something stupid. My parents should have heard us pull up by now."
"Oh joy."
"Chill, they're not that bad dude!"
"Well they did produce you."
"And what's wrong with that?"
"Have you looked at yourself in the mirror?"
"Huh?"
"You have lipstick on your collar."
Connor began craning his neck to search for the offensive smudge.
"Someone's looking guilty right now."
"You're one to talk."
"No actually I'm not dude as there isn't any lipstick on your collar."
Connor looked angry for a moment before it subsided and was replaced by a shit eating grin.
"And the student has surpassed the teacher."
"That happened months ago dude."
"My ego!"
"We should hurry up before they think we're up to no good in your car."
"What kind of trouble could we get up to?"
"There may not have been any lipstick on your collar, but there is definitely a hickey on your neck."
"No there isn't!"
Kennedy sighed as he used his phone as a camera, taking a picture of the offensive love bite.
"Dude keep it in your pants."
Connor stuck out his tongue as he adjusted his shirt accordingly.
"You're just jealous."
"Maybe, maybe not."
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The duo was standing outside a beautiful house surrounding by various types of trees. Evergreens dotted the landscape as the leaves of maple, oak, and birch began to change color. The house was a simple looking steel blue house with crisp white trim and copper gutters. Dormers adorned the slate roof. Connor stopped right outside a beautiful iron and wood door. Kennedy was unable to put his finger on the style of the house, but it reminded him of home.
"This is it, no turning back," Connor said in a solemn tone as they stood at the door, his hand grazing his neck.
Kennedy sighed. "I guess so, I hope they like me."
"It's not like we're going out or anything dude, then you'd have to be worried," Connor chuckled.
"Thanks for the vote of confidence… and that disturbing image."
"No problem. Just be a little wary of my mom."
"What do you…"
Kennedy was cut off by the sound of the front door suddenly swinging open. He turned to see Mrs. Windsor, a very beautiful woman with a straw colored hair and a simple navy dress on. It may have been very simple but it did wonders for her.
"Connor its good to see you!" she said hugging and kissing her son.
"Mom it's only been a few weeks!" Connor said trying to act cool in front of his friend.
"You're not eating enough young man! Clearly those tins of cookies haven't been touched."
Kennedy could only smile at the antics of mother and child. He let out a mental sigh of relief. The Windsor's, or rather Mrs. Windsor was very warm and bubbly.
Suddenly he felt the spotlight being put on him.
"And you must be Kennedy."
"It's nice to meet you Mrs. Windsor."
"Feel free to call me Cassidy. There won't be any of that Mrs. stuff here. I'm far too young for any of that."
"Ok, Cassidy."
"Now that's much better," she said with a smile. "Connor's been talking nonstop about you!"
Connor blushed as the teen turned to face him… 'Maybe that dating comment wasn't as much of a joke as I thought it was.'
"Nothing bad, in fact it reminds me of when I was younger with my sisters," she said with a warm smile before embracing him in a hug. Connor could only smile as Kennedy stiffened.
"Oh sorry, I guess you weren't expecting that." Cassidy was genuinely embarrassed at how the teen flinched at the physical contact. "Why don't you two freshen up? Dinner will be in half an hour." Both boys nodded. "Kennedy, honey, you will be in with Connor for the weekend. I hope you don't mind."
And with a flourish and spin Cassidy returned to "help" her husband in the kitchen, not that Kennedy knew that, before he could even respond. While she had all the appearances of a more than capable housewife, she was far from it as he would soon learn from the Windsor men time after time.
"I don't get what she meant."
He took in the 'cabin' with great attention. While it looked quite simple it was adorned with every modern convenience in a homey way. The rich character of the original period details blended flawlessly in with the big screen tv. The outside did little justice for the interior. The past glittered in the façade, but every modern convenience was present in the lavishly designed space.
"Now you know what I meant earlier. We can talk about it later Kennedy."
"I guess… they're good… I mean, they designed this I take it? It's freakin' awesome how they did the place."
Connor blinked. "Yeah, the house has been in the family for almost two centuries. Mom took this on as her pet project after I was born. This is just the latest version and far from being the last if that's any indication... It only seems to get bigger and better with time."
"Oh."
"It's a lot bigger than I expected from outside."
"My parent's are just good like that." Kennedy laughed at the feigned arrogance. "I hope you don't mind bunking with me, but I am presuming we are having guests over if we're sharing."
Kennedy shook his head. "Your house, your rules. Just no funny business as I still remember how we woke up together last time."
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The duo walked up the spiraling stairs to the second floor. With each step Kennedy began to imagine what it would have been like to be a part of the Windsor family as photos aligned the walls.
Kennedy spaced out for a bit and continued walking, grateful Connor was carrying the bags or he would have no doubt dropped his.
"You ok?" Connor asked as Kennedy nearly tripped himself on the top step.
"Huh?"
"Dude, just chill bro. My mom already loves you… maybe more than me. It's not fair! I've been here for two decades and its love at first sight for you. I get not respect I tell you! No respect!"
Kennedy ignored the tirade at first. He had no idea of how to respond to it. Was it sarcasm? The truth? A bit of both? He wasn't sure to be honest and he didn't want to risk choosing the incorrect option.
"Very funny." The teen hesitated before asking Connor a question. He didn't want to push his luck as it was. He was intruding on the Windsor's family time after all, even if they did have something to discuss with him. They had welcomed him into their home and he wasn't about to be rude, no matter how annoying his blonde counterpart was.
"Not to sound ungrateful or anything, but how much do your parents know about me?"
Connor sighed as he opened the door to his room. A king sized bed was the star of the pale gray room. Black furniture was placed around the room in a well thought out way. Two white leather wing backed chairs were placed in front of a flagstone fireplace. That seating area was completed with a fluffy white rug.
"Why don't we take a seat first," Connor said discarding the bags by what Kennedy presumed was the closet. The blonde took the chair on the left while the guest took the other.
"Ok…"
"First of all I really have to say I hope you don't mind sharing a bed with me this weekend. I know we're chill and all but I know things are only going to get more awkward this weekend if my mom's introduction was anything to go by… And don't you think for a moment that I buy your little excuse for last time."
Kennedy blushed, but not for the reasons Connor was thinking.
"I know that you don't like a lot of touching, but it's going to kind of be inevitable this weekend. Mom is very lovey-dovey and dad is well, you'll see when you meet him."
"It won't be a big deal. At least we're not squished into a twin. Now that would be awkward," Kennedy joked.
"Yeah it would be in the morning… But back to the subject at hand, I'm not really sure to be honest. My dad obviously knows more than me as I just accepted before they finished with the proposal."
"Really?" Kennedy asked clearly impressed with Connor's initiative. He didn't even flinch at the use of the word proposal as it was obvious it wasn't the other use of the phrase.
Connor blushed. "Yeah, I've err… well I've always wanted a little brother and well you've kind of become that for me. Its kind of why I always call you Bro."
Kennedy smiled warmly as he got up and walked over to Connor, much to the surprise of the blond.
"I'm honored that you see me that way Bro!" Kennedy said as he hugged him tightly. "Not that I really like the contact, but I think you've earned it."
"You're weird Bro."
"What did you expect Connor? I learned it all from you."
"Hey! I've only known you a few weeks."
"…Well its felt like forever. Your lame jokes grow old very quickly."
Connor nodded in agreement. "I know what you mean… HEY!" Kennedy snickered. "Now my mom obviously knows a bit but I would talk to my dad later if I were you. He's an alumni and was obviously was contacted by St. Jude's. The whole thing is kind of weird how it was set up but it worked out for the two of us right? I'm sure there's an official story for you to tell your friends, but that's all I know."
"Yeah I know what you mean. So if there's a guest how are we going to do this?"
"I'll play it by ear. I think much better on my feet as you know. I'm sure my dad will seek you out if it comes to it… They didn't ask me to invite you outright, but they were both very excited when you agreed." Connor failed to mention his numerous conversations with each of his parents over the planning of this meeting.
"And here I thought you just loved my company," Kennedy smirked.
"I do or I wouldn't have invited you here now would I?" Conner countered as he looked toward the bed.
"Maybe you're just in love with me?" Kennedy said wagging his eyebrows.
"You wish" Connor said throwing a pillow.
This exchange led to an all out pillow fight as if they two were children. The duo's fight ended in a very compromising position as they heard a knock followed immediately by the door opening and the arrival of a built brunette man in a blue striped shirt and navy pants. The look was completed by a argyle tie and brown leather belt and shoes.
"You move fast Son," Mr. Windsor said. "I'll let you two finish up. Dinner's ready… I guess you'll be calling me Dad in no time Kennedy!"
"It's not what you think!" the two young adults said at the same time with respective blushes as they adjusted their clothing and hair.
"I could tell by the sound of all of the furniture falling. Be careful Kennedy, I'm sure my wife is already planning a wedding in her head," he said moving closer to the two.
Connor's jaw dropped at the thought. Kennedy could see where Connor's humor came from.
"You can't be serious Mr. Windsor."
"What did my wife tell you?"
"You never gave me you first name so it can't really apply," Kennedy retorted as Mr. Windsor smiled.
"I'm Kyle, young man," he said extending a hand while helping Kennedy up. "While Connor catches up with Cassidy later we can talk Kennedy. I'm sure there are a few questions I might be able to answer for you."
"Thanks Kyle," Kennedy replied. He was surprised at how easily things were falling into place. If he were having any doubts about the authenticity of the Windsor's before, they were beginning to stab him even harder.
"Now I'll distract Cassidy as you two clean yourselves up. Don't want to put any more ideas in her head. You haven't had a girlfriend in a while Connor so your mother is beginning to wonder… It's none of my business but I thought I would give you a heads up," Kyle said to his son who was still on the floor. Kyle turned to leave the room as Kennedy helped Connor up.
Before the door close completely, the adult peeked his head in the room.
"What you two do on your own time is between you, but remember Son, he's jailbait."
The serious look on the elder Windsor's face had the two of them completely unnerved. Yet another bout of awkward silence developed between the pair.
"Why do your parents…"
Connor glared at him. "I don't know… I guess we've become closer than we thought fairly quickly."
"Yeah… you're not…" Kennedy began blushing.
"No!" Connor said as the two headed for the door. "I just have been really picky and don't want to let them down. It's a hard feat to live down considering how storybook romantic their relationship is."
"Well it wouldn't bother me either way… especially with that big bed of your's," Kennedy said seriously looking back and forth between his friend and the bed.
*Smack*
"Don't joke like that Bro or you may have to keep an eye open at night," Connor said with a wink.
"We should really stop before this gets out of hand."
"Yeah… if my mom over hears she may think we're serious."
The two chuckled at the thought.
"I wonder who the guest is."
"It might not be anyone. THEY may think we'd be more comfortable together since its CHILLY."
"Sure dude, keep thinking that."
"Well you don't know my mother like I do. She's not very subtle."
"I'll take your word for it."
"No seriously Bro you have no clue what you're getting in to."
"I think I have enough to go on, after all you're your mother's son."
"Hey!"
"I think your dad likes me, maybe even more than you."
"That's not fair!"
"Stop acting like a five year old and get ready. I take it your mom is a stickler for the rules?"
"Kind of… They take turns playing good cop, bad cop," Conner said as he unbuckled and unzipped, tucking his shirt back into his pants and then reversing the process.
"Oh joy," Kennedy said from the bathroom, adjusting his hair and tie.
"Just don't insult the cooking."
"I wouldn't dream of it."
"No I'm serious."
"Dude…"
"Kennedy just don't do it. If you don't like something, don't make it obvious. Trust me."
"I take it you didn't eat your vegetables growing up?"
"I did… well some of them. I'm talking more about things like duck liver and quail."
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Spotted Mystery Boy in the company of Connor Windsor once again. Is there romance in their future? Or is it just another Upper East Side bromance? Mystery Boy sure is a social climber. You sure are full of surprises. Golden Boy is nothing compared to the standard of a well-bred Windsor man. You've done very well in landing such a talented companion.
XOXO, Gossip Girl
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If I get five reviews for this chapter I'll release two more chapters this week.
-Griff