Hi all! This is my first published fic. It's Klaroline-focused but includes most of the Mystic Falls clan, and takes place a few years after the events of the series finale. References The Originals but not completely canon. May occasionally reference triggering material; any relevant warnings will be listed at the beginning of the chapter. Obligatory disclaimer - I don't own TVD, The Originals, or any of the characters. I really hope you enjoy this, and thank you so much for reading!

Chapter 1: The Check

Another Monday came to a close at the Salvatore School for the Gifted. They were up to almost 20 students, ranging from Josie and Lizzie's age up to 13. Not a day went by that Caroline didn't feel taken aback by what her life had become. Headmistress (weird), drama teacher (great), mother (challenging yet awesome), widow (sigh), orphan (still terrible), and vampire (pretty normal, all things considered). She'd just walked the halls one more time, calling lights out, knowing full well that five minutes later all of her students would have the lights back on again. Each teacher at the school had a night to be the "bad guy" - the one who came back after that five minutes to shut the lights off for good. Thankfully, Monday nights belonged to Ric.

She trudged into the kitchen, renovated shortly after the school opened to accommodate cooking for a large number with funds from a certain substantial donor, and pulled a stool up to the giant wooden cutting board table. Letting her high heels drop off of her feet (it's not like the health inspector was about to walk in), she poured herself a glass of red wine and took a slow sip. Suddenly, she heard someone running toward the room. An adult, she could tell. They smelled like...hospital.

"Hey Care! Bye Care!" Elena yelled, speeding through the kitchen and out the back door, beeper going off. She'd been there teaching that day. They'd worked it out so science classes were taught when Elena wasn't at the hospital, and she'd been teaching that day, hoping that if she were called in, it wouldn't be until later. And off she went.

"Bye Dr. Salvatore," Caroline called back in a teasing voice, hearing the door slam behind her. Technically it was Dr. Elena Gilbert-Salvatore, and even though she and Damon had been married for a few years now, Caroline still liked to tease her friend a bit.

Caroline picked up her shoes and glass of wine and began to make her way to her suite. The school, after some renovations and additions behind the original boarding house, was big enough that some of the staff could stay on the property. She and Ric had their own separate quarters. Damon and Elena built their own house nearby, with Jeremy living in an apartment above their garage. Bonnie kept an apartment at the school, albeit a small one - she traveled a lot. Caroline and Ric had given Josie and Lizzie the choice of staying in their apartments or sharing a room in the hall with the other students, and they'd chosen to take a room in the hall with their friends. They were old enough and under the close, watchful eyes of many a teacher and family member.

She opened the heavy mahogany door to her room and breathed a sigh of relief after the door clicked shut again. Another day complete, with no fires, broken windows, blood spilled, or spells gone awry. In a school full of vampires, witches, and wolves, there weren't many days when something a regular human would consider a catastrophe didn't happen.

Then she saw something out of the corner of her eye.

Under a colorful stained glass lamp on her entry table lay a thick padded mailer envelope, no visible stamps, unmarked save for a round red seal faintly printed on the top corner. Was it that time already?

Each year, she received a similar envelope. Sometimes white, sometimes manila or brown, always with the same red seal. Two people would pull up in a black Mercedes, and would leave the parcel with Caroline's secretary with explicit instructions that it only be given to Caroline, and that no one else was to know about its contents.

Caroline took a final sip of wine from her glass and sighed down at the envelope, tracing the red seal with her finger. These were the envelopes that kept the school going. Some of her students' parents were rich and contributed sizeable amounts to the Salvatore School, while others were essentially orphans with little to no contact with family. But she and Ric had vowed early on never to let any child that needed their help be turned away, especially for financial reasons. To be a supernatural child was incredibly difficult. Not all parents were up to the task of raising one, even if they were a supernatural being themselves. Some parents had worse fates befalling them. They were all too familiar with the instability and violence being a supernatural creature could bring into one's life. Like everyone that worked there, some of the children had no parents. It was something many of them had in common. They could relate.

But even the parents who did send money couldn't touch what came in the annual envelope. Caroline carefully cut the top of the envelope, popping the bubble wrap inside, and pulled out another smaller envelope, this one made of thick parchment and sealed with a red wax stamp on the back. She traced her finger over the seal, took a deep breath, and carefully slid her finger under the wax.

Enclosed was a check. Caroline covered her mouth and fought back tears. Another $3 million dollars, sent from the Mikaelson Estate. With HIS signature, this time. Last year it had been Elijah, the year before an accountant working on behalf of the estate. Her breath hitched when she saw it. Then she noticed something else in the mailer. Sometimes the annual check would come with a letter from whoever was sending it. When Elijah signed last year, he sent a brief update; Hope was getting older, Klaus was fighting over New Orleans and was on the run half the time, and there was always a 50/50 chance of Kol and/or Rebekah being daggered. She knew he and Hayley were together in some capacity, and that Freya was still with them. She never got much more detail than that, understandably so. The less she knew, the better. It meant less risk for the school and everyone in it.

Caroline fished out a wax paper sleeve a bit bigger than a postcard that contained a sheet of thick drawing paper. It made her excited, frustrated, and sad all at the same time. And confused. And forlorn. And it made her feel guilty.

Caroline, she read, hearing it in his voice,

I hope this will continue to sustain your noble efforts for the coming year. Should you need anything at all, please contact the number on the opposite side. Things are tumultuous in New Orleans. I take comfort in knowing you are safe and thriving.

I am thinking of you always.

Yours,

Klaus

Around the note were sketches of mossy trees, the kind she'd seen in New Orleans when she'd gone to find him. As always, the artwork he sent was beautiful, even though from his perspective they were just quick sketches requiring little effort. She felt equal parts so many things as she carefully slid the check back into the mailer and locked it in her hidden safe.

Relief, as that money would allow them to expand and renovate further, hire another teacher, and handle a whole slew of other practical and pressing concerns.

A little mushy - each year she secretly hoped it would be him that sent it, that she'd smell his cologne on the paper and maybe even something he'd drawn especially for her.

And guilty. It had only been a few years since Stefan died. She felt a pang of guilt every time she saw someone on the sidewalk she found attractive, double the guilt when she thought of Klaus and everyone's complicated history with him. But they all had complicated history. With everyone. She hadn't expressed interest in anyone or put herself out there, though a few men around Mystic Falls had tried to chat her up. Instead she buried herself in her work, running the school, teaching, being a mom. It was more than enough to fill 24 hours a day anyway.

And finally, frustrated. Stefan was gone. She said she'd always love him, and she did, and she would. But he was gone, and she was still here, and all she wanted was to give herself the girl living inside her the permission to be excited that someone out there, a very handsome, broody, tempestuous, frequently frustrating, and exceedingly loyal someone, fancied her, as he'd once said.

Eventually she crawled into bed, snuggling under her favorite quilt taken from her childhood home. At one time, it had covered Liz's bed, and Caroline had frequently snatched it during movie nights on the couch with Bonnie and Elena. In the soft lamplight, she traced the details of the note with her eyes, noticing the roots of the trees and the amount of detail he'd managed to work into such a small space.

I am thinking of you always.

Yours,

Klaus

She re-read it, hearing it in his voice. Soon after, she set the note aside and turned off the light, inhaling the faintest trace of his cologne as she drifted off to sleep.