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.

:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:

Connor must really enjoy being your chauffeur K. I dare say its much cheaper too. Why pay when you can get a service that is much more personal? You certainly have a way with the handsome ones. Would you mind toning it down a bit?

Some of the ladies would enjoy having their boyfriends back… Have fun wherever you're going with the Windsor heir tonight K. I'm sure it will be fun.

XOXO, Gossip Girl

:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:

"You don't know how to cool it do you bro?" Connor said as he turned the key in the ignition, his signature sunglasses perched on his face.

"What are you talking about?" Kennedy feigned innocence, glad he didn't have to look directly in the blonde's eyes, but at the same time nervous because the reverse couldn't be said.

"Your bromance with Nate Archibald."

"I hate that word." A chill ran down the teen's spine.

"Just be careful. Like I've said before, I don't care who you sleep with but be careful literally and figuratively," Connor lectured pulling out of his spot and driving down the street. "You and Archibald seem very cozy together by the way… I honestly can say I didn't see that coming considering everything."

It took all of Kennedy's composure not to blow right then and there, but he held his ground and let the older male continue on his lecture.

"His girlfriend is a brilliant schemer from what I've heard, definite superiority complex, but a schemer nonetheless. Oh the times… I'm so glad I'm not in high school anymore. Sure the high school drama still butts its head in my life, but its different… You actually care about what people think about you in high school. College is a whole different beast."

Kennedy was deep in thought at Connor's later statement. There was a definite nugget of truth buried deep in there, something that he would hold onto to think about at a later time. But for now he had some good news for the blonde that would not hopefully make him crash into another car on account of the glee and pride he would soon be feeling as the driver's ego inflated to the size of the Empire State Building.

"I'm apparently a natural at soccer, even the Coach agrees," Kennedy added sarcastically to change the subject. "I'm apparently a really good goalie. Nothing got between my legs."

"Well you did have my help… Not that anything belongs between your legs Bro."

Laughter was all the response Connor received. The blonde took that as his cue to continue on with his interrogation.

"How were classes?"

"I could ask you the same thing."

"Nothing big little bro, but Dad told me you have quite the plateful."

"Yeah. Four AP's and an honor's… I'm going to die between Chem and Bio alone."

"Add soccer in the fall and lacrosse in the spring and you'll either be at the top of the pyramid or a hot mess… Juggling a current seasons practices with the training for the following one will take a lot of careful planning. Thankfully Mom and Dad are good at that. I don't think I could have done it without them."

Connor didn't let the glare stop him.

"Try adding wrestling or hockey for the winter while you're at it. I'm sure you'd love to find an excuse to grind against Archibald or some of your other peers. Putting some of the bigger dumbasses on the mat is also very satisfying… And besides you'll be Gossip Girl's favorite Upper East Sider in no time!"

A hard punch to the arm ended that conversation.

"He's seemed weird around me lately. I don't know if it's because Chuck Bass told him more about my past or if he's just into making all of his friendships into bromances. Seriously dude are all athletes that err…"

The blonde male adjusted his face as he thought deeply. By he, Connor knew Kennedy was referring to Nate Archibald. It seemed like a lot of Kennedy's problems would be involving him from this point forward. Between the furrowed eyebrows and contorted chin, Kennedy didn't know whether to laugh or be scared.

"I didn't really get to know him so I can't say much… I still say he has an ulterior motive in befriending you so quickly and so easily. He's known for always getting what he wants. From what I've heard Nate isn't the best student so I'm guessing he's going to aim for you to tutor him as a friend. Though that's all contingent on his girlfriend and father. If they're complacent with where he is, then that theory goes out the window."

Connor made a sharp turn that resulted in an ever-increasing glare from his passenger.

"Sorry about that, but I'll take that as it as a yes then. And I will also take it you get one on one training sessions in soccer and/ or lacrosse with him?" Eyebrows raised and moved suggestively causing the teen to blush crimson in response. "You two sure looked cozy snoozing in precalc."

"Must you always make everything sexual. He's not even close to being my type."

"Only when it comes to you my baby brother. You're so easy to rattle." Hair was ruffled and then fixed. "Now do you feel better?"

"Yeah, but do you always have to do that?"

"Not my fault you get wound up so easily you prude. It's only the first day of school and you've already had as much craziness as Lifetime Original Movie. When should I expect a love triangle between a boy and a girl?"

A quick and well placed punch to the arm as well as a change of subject put an end to that topic quite easily as Connor spent more time nursing his sore arm instead of finding more about the basis of Gossip Girl's blasts today.

"How's your lady friend?"

"No changing the subject." Connor liked being in control. This was so not part of the plan!

"So things aren't going well?"

Connor growled before pulling his phone out of his pocket as they stopped at a red light. He threw his phone at the teen.

"Shut up and just read. Gossip Girl loves you apparently. You couldn't lay low for one day could you? Things are only going to get worse from this point on." The arrival of ringtone alerted the two males to incoming danger. "And speak of the devil, she must have some more dirt on you!"

"Eat it up you jerk. Chick's dig mystery. You're not important enough to even have an alias. You're a no one!"

Connor scoffed but turned his attention back to the road as they still had quite the drive ahead of them.

:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:

"Do you want to do the honors?" Connor asked his "brother" as the duo came to an imposing door.

"Shouldn't you be carrying me over the threshold?"

"You two didn't tell me you eloped last night?" a female voice said as the door opened.

"Mom." "Cassidy."

"Come in now before our neighbors think you two are serious. All we need now is the Granger's spreading rumors of Connor seducing a MALE high school student to throw a wrench in things."

"Not my fault," Connor said with an innocent look. "Kennedy must have some crazy pheromone or something… He sure knows how to drive all the guys around him crazy."

"Well if YOU kept your hands to yourself…"

"Boys, we have more important things to discuss than your sordid love lives," Kyle said entering the room before adding another comment in a much lower tone. "As long as you wear condoms…"

"Sorry," both of the youths muttered as Mr. and Mrs. Windsor directed them to the living room. Kyle's second comment went over their heads but not Cassidy's. A certain sparkle appeared in the corner of her eyes.

The adults took the two club chairs while the young adults plopped down on a very comfy brown bonded leather couch. Mrs. Windsor may have been more of the type to use humor to procrastinate and avoid the inevitable, Mr. Windsor only use it to lighten the mood. Right now was one of the times he was getting straight to business.

"Kennedy, did anything seem off today beyond the obvious?" Kyle asked.

"Some of the teachers… they well looked as if they knew more about me than they should. Especially what's his face teaching AP Chemistry," the black haired teen said trying to remember that particular instructor's name. "I don't know how he knew about my old school and who I was taught by. I honestly thought he would only see my grades to see whether I was qualified or not to be taking his course. I didn't expect for him to have a thorough background check like I was some criminal or something."

"Should we scoop him out now Kyle, there are plenty of other schools… It's still early enough in the year. Riverside…" Cassidy was cut off before she could even finish her statement. Sure it was no St. Jude's but it would serve him quite well just the same if it meant he wouldn't be at the same risks, in fact it may have been even better for him considering he'd be even further at the top of the academic pyramid.

"No, I think I should let it play out for now," the teen in question replied surprising the family. "After all, that money is nonrefundable and I would rather not waste the money if I can avoid that. Whomever is behind this may react poorly if I do that, then we would have no idea of what they're up to. By staying at St. Jude's at least we can control some aspect..."

"You don't have to be brave all the time bro," Connor said embracing his friend/ brother. "It's still early enough in the school year…" Unfortunately, the blonde was cut off by a hand to his mouth. He grumbled out a few not-so-pleasantries as he was stopped before he could finish his line of thought.

"Well wouldn't staying and playing dumb be the best way to get to the bottom of it? And besides, I'm sure Chuck Bass wouldn't let anything happen to me. He's oddly protective of someone he barely knows."

"How do you know him Kennedy? He has quite the reputation," Connor asked for his parents. Sure he didn't know the Bass heir, but you didn't have to know him to know of him. Chuck Bass had quite the reputation after all. His parents may have been all gung ho about grilling the teen, but from their looks it was all up to him at the moment.

"We go back, I don't really feel comfortable going on about it right now, but you can trust him… well at least when it comes to me."

"We won't press any further on that subject then," Cassidy said glaring at her men, to which Kennedy was grateful. Though she sent a sympathetic look at her son when neither Kyle nor Kennedy was looking.

"Unless Nate Archibald gets kicked out of my AP classes, I have him or Dan Humphrey in all of my classes except for AP Latin. Both of them seem pretty trustworthy. Then again first impressions aren't everything."

"Why does that last name seem so familiar?" Kyle asked his wife. His words may have been obvious, but his eyes spoke volumes.

"I'm not sure Honey," she replied with a slight tinge of pink developing on her dimples. She had an idea where she remembered the name, but was too embarrassed to admit it.

"Archibald is a good kid for the most part Kennedy so it would be good for you to be around him. Making connections is just as important as making friends HERE. He would also be a good a way to get on both teams as he's a bit of a star on both. However we would prefer if you did not partake in his other extracurricular activity young man. He has a bit of a reputation of being a bit of a well stoner… and his grades reflect that." Kyle felt bad mouthing the teen's friend but he had to know now while the year was still fresh. An ounce of prevention is more than worth it after all.

"I understand and I'm already a few steps ahead of you!" the teen replied cheekily. "I made him promise not to use any around me if he wanted my services."

"Cheeky monkey" Connor whispered low enough so only his buddy could hear him. The tone of the teen's statement was lost on the adults, but the college student caught on quick enough. Kennedy may not have admitted it, but there was a hint of interest hidden in the not so subtle use of the word services.

"We're trading favors," Kennedy announced to the horrified faces of the adult Windsor's. The two youths had to fight the urge to burst out laughing. Suppressing their grins was quite the challenge indeed as the looks on their faces was quite frightening and hilarious at the same time.

"Not like that! What is it with this family?!" Kennedy got up from his seat and began flailing about only to be shoved back down by Connor. After a few more moments of looking like a complete fool, he regained his composure and continued. "He's helping me on the field and I'm tutoring him! I'm not that kind of guy people!"

The three Windsor's had the decency to look thoroughly embarrassed, though that wasn't enough for the teen.

"That is a good approach, as the quicker you integrate yourself, the less at risk you will be. The more allies you forge amongst your peers the better. You never now when the Headmistress or someone else in the administration or faculty could turn on you." Cassidy was still crimson at the thought of her pseudo son and his friend being together. "Making others reliant on you will help secure your spot and add lines of defense against potential threats."

"I'm not in the middle of a social war Cassidy."

"You're in high school, that should speak in enough of itself." She said it as if it were the most obvious thing in the world. Kennedy had to restrain himself from slapping himself on the forehead with how true the statement truly was.

"Touche."

"Why don't you two hit the books while I start on dinner?" Kyle asked, well more like ordered.

"Sure thing Kyle." "Fine Dad."

"I'll whip up some cookies if you two get a move on now," Cassidy said causing the two youths to trip over themselves as they darted out of the room and made a mad dash for the blonde's room. The thought of those luscious morsels of goodness was enough to make them enjoy doing homework on a Friday afternoon.

"I still don't understand how you can bake, yet any time you cook it ends in tragedy. It's just not right." Mr. Windsor whined as he watched his wife begin to make a mess of his kitchen as he worked around her to get a start on dinner.

"I don't know either, maybe it's the careful planning. After all, you can do all the work for me if all I have to do is make dessert," she replied feigning a kiss. "There is so much room for error in them that I have to be precise unlike when you cook. You have much more wiggle room based on experience."

"Honey..." A quick elbow to the small of his back was more than enough for him to stop.

"That's what you get for insulting my cooking skills."

"Keep that up and you'll be on the couch tonight!"

Mrs. Windsor had the decency to blush as he wasn't all gentleman all the time. He was not above kicking her out of the bed when she was wrong!

:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:

"Nice room bro," Kennedy said looking from place to place.

"I'm surprised Mom hasn't redecorated yet, she sure enjoys redoing everything fairly often. And with you here I'm surprised she hasn't installed another bed in here, there's more than enough room for one."

"I'm not taking your room. I've taken enough."

"More homework, less talking gentlemen!" came from down the hall.

"How does she do that?" Kennedy asked dropping his bag.

"I don't know. Desk or bed?"

"It's your room."

"I only have reading so I can do either."

"You take the desk, can't have you falling asleep on me Connor. I know how you think buddy. It's that time of day after all you old man."

"Very funny Kennedy."

"We both know its true."

"Well… screw you!" he replied plopping down at the desk.

Connor got to work highlighting as he read over his psychology textbook. Kennedy on the other hand made himself comfy on the bed and began doing his writing homework. After a while the duo had moved onto other work.

"Hey Connor, how do you do this?" Kennedy said adjusting himself on the bed. Connor spun around on the chair and sat down next to him on the bed.

"It's not really that difficult. You're on the right track. You messed up right here though," Connor said pointing to a step in Kennedy's math. "Your final calculation is thrown off because of that."

"Not everyone is a math genius."

"Well you're oddly good in science and writing. You can't win them all."

Kennedy pouted. "Your Latin teacher still blushes at the mentioning of your name, did your dad tell you that?" Kennedy said gaining the upper hand. "What did you do or not do with her to make her so flustered and tremble as just the mention of your name?"

"Nothing at all! I'm serious Bro, but I don't know why she ever liked me so much. She's not that much older than me also so it was always weird. Sure she was wicked hot, but I wasn't going to cross that line."

"Not to feed your ego, but you're pretty hot bro."

"I know that," Connor grinned as he popped the collar of his shirt in an obnoxious way. "But it sounds so much better coming out of your mouth."

"She's so boring for such a hot teacher."

"There's only so many ways to make a dead language interesting dude… But I have to agree she's quite hot… She was the focus of many a daydream."

"Just for that you can help me with Latin too! And I think you meant wet dream!"

"What about my homework?... Wait! Why you little smart ass!"

"I thought you would do anything for your little brother."

"Fine."

"In return I'll be the one to break it to Mason there's been a change of plans. Since you obviously forgot to tell them we were coming here tonight."

"Whoops." Connor scratched his head in embarrassment. "I knew I forgot to do something today… Bro that's actually a fair trade, even if you think I even had a need for wet dreams."

"I knew you would see it that way." Kennedy completely ignored the wet dream comment.

"You're a lifesaver once again bro," Connor replied sheepishly as he went back to checking the Latin assignment..

:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:

Hey Mason, I'm spending the evening with the Windsor's. Mr. Windsor decided on it spur of the moment. Enjoy your night off :D -K

:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:

Not a minute later:

:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:

No problem. Enjoy yourself tonight. Kind of forgot myself. Don't let that doofus rub off on you. -M

:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:

"See I told you."

"I thought you called him a jerk Kennedy," Connor said not looking up from the beginnings of the translation. "You mixed an ablative absolute with an ablative of means here."

Kennedy let out a huge and silent sigh of relief as Connor ignored his phone. If Connor had seen the text, the brunette was sure the blonde would have done something really stupid. Sure Connor wasn't the brightest bulb, but his temper was kind of nasty. And unfortunately Kennedy had been on the receiving end of it not long after they first met. The teen thanked the heavens that it was only that one time. Kennedy could only picture Connor channeling that anger on the field.

"That's why I have you for." The brunette did his best to hide the ghost of a smile. The text was quite entertaining in his opinion. Kennedy knew that if he wasn't careful that Connor would be on to him and snatch away his phone.

"I still don't know how you got into AP Latin. Your translation is so shoddy and this is quite easy Bro. You're not going to survive the class at this rate."

Kennedy broke out in laughter. "This is so ironic dude. I don't know how I will either. Someone out there must really hate me to get me in... I barely passed it as it is at my old school and I didn't have a chance at going Honors., let alone AP!"

Their little heart to heart was interrupted by the matriarch of the Windsor Clan. It was just yet another moment that made them both point their finger at something that was missing out of their lives. Unfortunately neither would notice it as it was neither the first nor the last time any attempt at putting together those thoughts would be effectively extinguished like a candle in the wind.

"Boys, dinner!" a feminine voice called out ending things.

:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:

Dinner was a fairly simple affair. Well as simple as one could get with one taking part in a meal with an Upper East Side family. Navy rimmed white fine china plates and brilliant silverware adorned a mahogany Victorian styled dining table with walnut inlay details, as the Waterford crystal glasses glistened, casting radiant reflections onto every available surface. Crisp white linens balanced the dark wood Chippendale chairs and ornate draperies. All in all, it was timeless, classic, and effortless beauty that would stand the test o of time. The imposing nature of the setting for their dinner was daunting, but the teen was ready..

"So how was school Kennedy?" Cassidy asked tossing her salad.

"It was fine," he said passing his salad plate over to her. "Definitely not as bad as a certain someone made it sound like."

"I was mentally preparing you for the worst," Connor said defensively. "It was basically as bad as I predicted right?"

"I wasn't talking about you Connor, though your description of the locker room didn't do them justice. They're way classier than anything I'm used to."

"Then who are you talking about bro?" he asked confused. In fact you could color all three of the Windsor's confused. Kennedy liked playing mind games, not that you would expect that looking at him. He kind of had the whole innocent nice guy act down to a t.

'Cue the dramatic music,' the teen thought as he prepared to start something, finally focusing his attention at the suspect in question. "Your father."

"KYLE!" "Dad!" The two blonde's went off on the older brunette just as Kennedy had planned. Kennedy was good at deflecting, something none of the Windsor's had realized just yet.

"Hey, I had the same concerns as Connor. What did I do?"

The teen smirked. 'Game, set, match.' Kennedy put it on a little thick as he quickly got to his point. "I greatly appreciated your concerns, but you laid it on a little thick."

"That's not the only thing that's a little thick," Cassidy added to lighten the mood.

"That was low Cassidy," Kyle replied as he felt the figurative stab in the back… or should we say stomach?

"So was terrorizing Kennedy. Now let's drop this before I start us all on a new dietary regimen." The Windsor men looked in horror as did Kennedy. "Now that's more like it. How do you like you schedule Kennedy?"

"Well I have an AP Latin teacher that has the hots for Connor…"

"Kennedy…"

"I'm serious Cassidy! I'm surprised she didn't seduce him when she had the chance." Connor's face was a crimson as it could get as he tried to sink even further into his chair. He didn't appreciate being brought into this once more. And even more so he didn't want to bring up those memories…

"She was tripping all over herself when she saw me Cassidy." Kyle didn't even bother looking up as he cut a tomato with his knife. "It was quite pathetic to be honest. She was like an abandoned puppy when I walked in."

"Oh lord…" Cassidy said feeling a familiar headache come on.

"Then there's AP Chemistry where the teacher has it out for my lab partner Nate Archibald who is also by AP Biology lab partner, but that class is much better. If I can get him focused on things, I'm sure we can put the stoner thing to rest, but I hope that was more of an exaggeration than actual fact... Don't even get me started on the other archetypes that are running wild through the halls of both schools... Moving on, AP English Composition and Honors English on the other hand both seem easy, but with a lot of work attached. I have my friend Dan in both of those classes so I'll have his help to fine tune things there… Precalculus, I don't know. I hate math, but I have both of them to keep me entertained."

"Well it's a good thing Connor's good at it. In fact he'll be more than happy to help you in Latin and math."

"I will?" Connor said looking up from his food.

"You will." Cassidy turned her attention to the other youth. "That is if it's ok with you Kennedy."

"I guess," Kennedy said playing with his food. He wasn't really one for salad, but he wasn't about to insult the hand that was literally feeding him. "I just feel like that either its going to be a really good year or a really bad one. From the Headmistress to some of the teachers and students, it just doesn't feel right."

Using the awkward silence that followed, the adults cleared before bring out the entree. Connor and Kennedy's mouths both watered at the sight before them. Now meat was definitely some Kennedy could sink his teeth into literally and figuratively.

"It will get better, you just have to let the New Kid Syndrome wear off a bit," Kyle lectured while cutting his fillet mignon with ease, in fact it was like cutting through butter. Kennedy smiled as he sliced through his own. 'I could definitely get use to this,' the teen thought as he listened attentively. This lifestyle was something he could certainly appreciate after so many years of struggling to get by. It was like a god send, or maybe karma?

"There's so much mystery about you, which doesn't help. And with you being admitted under the previous Headmaster that is mysteriously replaced at the beginning of the school year can only add to it. You'll be the focus of the attention of your peers, their parent's and the administration."

Kennedy didn't really know what to say. "Speaking of that, did you find out anything else about it? Headmistress Queller sure is a pain to put it nicely."

"Robert hasn't got back to me yet. And none of my contacts have found anything either. Cass, has your network dug up anything?"

"No Honey, but I do find it odd they brought in someone new instead of promoting one of the assistant headmasters at the last minute."

"All this talk of St. Jude's is making me bored. Can we change the subject?" Connor asked innocently. "I'm sure Kennedy would much rather have us talk about all of the Gossip Girl posts about him instead."

"Oh really," Cassidy said with a wicked grin that was matched by her son. "I wasn't aware you still subscribed." Connor waved it off as Kyle meanwhile sent a sympathetic look to the teen while going back to his second steak instead of getting involved with the brewing storm. "Go on Connor. I'm quite curious to see what she has to say about our little magnet for trouble."

'They're crazy, but its nice to know what it feels like to be part of a family,' Kennedy thought as he began to answer for his actions… or rather the candid portraits people captured out of context and submitted to the gossip site did so for him as Connor passed his phone to both of his parents.

:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:‾:

What did you think? Sorry about the lack of a posting but life has been hectic... This is the first of a bonus double post this week. I'd really appreciate feedback by the way :D

-griff