Disclaimer: The characters in the following story are property of their respective creators and are being used without permission. No profit is being made from the use of these characters.

A/N: So I haven't written anything in ages but for some reason over the last few days, I've had the strongest urge to write these "firsts" one shots (I have three in mind at the moment). So I hope you enjoy them! If you have any prompts that you'd like to see included, send me an email/PM or leave your request in a review! This is rated M for a reason, and that reason will become apparent in the next chapter!

Emma sat at her desk, twirling and un-twirling a strand of hair around her index finger as she clicked through files on her computer, organizing them for the third time today. Tomorrow was the first day of summer vacation which meant that her files could be stored neatly (and alphabetically) away for a few months. She was daydreaming really, her files were in perfect order, it was only a matter of transferring them to a disc; her thoughts were focused down the hall where Will was wrapping up his last meeting with the glee club, trying to keep some fire beneath them after their dismal performance in New York.

She watched as Finn and Rachel walked hand-in-hand down the hallway past her office, sparing her a quick wave as they headed out. If those two were out, it meant that the final glee meeting of the year was over and she could finally go talk to Will. Except, what was she going to say? Things had been awkward since she'd told him her marriage had been annulled and she just wanted to get back to the easy camaraderie that she and Will once shared.

Didn't she?

This was the question that had kept her in her seat well past the final bell and well past an appropriate time for her to head home. Home. To her empty apartment. By herself. The thought made her shudder and she sighed. Did she really just want to go back to being friends with Will? Or did she want to get back to the time when they'd been in a relationship (dysfunctional as it may have been)?

Could she forgive him April? Shelby? Holly? The list made something inside her twist with jealousy and envy. He told her he hadn't slept with April or Shelby but she hadn't had the heart to ask about Holly. Their relationship had been so fractured then, it hadn't seemed her place to ask but God had she wanted to know. Deep down, she knew the truth. He'd slept with Holly, the confident, sexy blonde bombshell. How could he not? It's not like she had been available, after all, she was the one who had run off to Vegas and married her freaking dentist. Regret welled inside her, competing with that green-eyed monster, jealousy, for space.

Will watched her. She was so cute when she was concentrating and Will could tell something serious was on her mind. A strand of hair was wound so tightly around her finger, her fingertip was blanched and she was chewing her bottom lip with a force so strong Will was surprised she hadn't drawn blood.

"Hey Em, something on your mind?" He smiled as she startled, clearly having had no idea he was there, leaning against her office doorframe.

"Oh it's nothing, just finishing up for the year," Emma smiled, shut down her computer and sanitized her hands.

"What are you still doing here? You could have been gone ages ago!" Will secretly hoped she had been waiting for him, not that he'd ever tell her that. He wasn't sure she was ready to embark on another relationship, it hadn't been very long since her annulment had been finalized and the raw pain in her eyes when she'd seen him with Holly made him wonder if she could forgive him for attempting to move on when he thought he'd lost her forever.

"Oh. Um. Well…I just…" Will chuckled to himself, loving the crimson blush that quickly stained her cheeks.

"Emma would you like to get some dinner?" Will asked before he could stop himself. Emma's eyes widened in that puppy-dog way that she had and she nodded, suddenly at a loss for words. Emma picked up her purse and brushed past Will who remained standing in her doorway, a little surprised and a lot grateful that she had agreed to share a meal with him. Will extinguished the light in her office and pulled the door shut behind him before turning to face Emma. He could see a thousand questions swirling in her eyes but she seemed to have been struck dumb and just silently turned to head out into the quickly cooling evening air.

Dinner had been nice. Less awkward than either had anticipated, probably due to the fact that their conversation had stayed maddeningly superficial the whole evening. Emma surprised herself by asking Will up for coffee when they got back to her place.

Emma perched awkwardly on the edge of a chair in her living room, staring at Will who was seemingly at home on her couch, sipping a mug of coffee.

"Did you sleep with Holly?" The words are out of her mouth before she can rethink them and she clapped a hand across her lips as soon as she realized what she'd asked. Will choked on the mouthful of coffee he'd been trying to swallow, stunned that Emma, shy, quiet, introverted Emma, was asking him such an intimate question.

"I – do you really want me to answer that?" Will had always thought she'd known, they had been moving on, both of them.

"No." Emma said in a small voice, "I guess not."

"Emma…you were married. Carl was helping you get better. I thought you were gone. That I'd ruined my chance with you." Emma shrugged, regretting that she'd started this conversation. "I'm sorry Emma, I never wanted to hurt you."

Emma studied a loose thread in the carpet at her feet, jealousy and pain choking off her words and bringing stinging tears to her eyes.

"I'm sorry Will, this isn't fair. You're right. I was the one that sent the message that it was over. I was the one that went to get married in Vegas." She jumped when she felt Will's hand under her chin, lifting her eyes to him. She hadn't even heard him get off the couch and now here he was pulling her to her feet.

"What do you say we start over?" he whispered. Emma's eyes widened and she nodded slightly, her entire being focused on how close Will's lips were to hers. She had started this and she wasn't about to stop now so she leaned in and closed the gap between them. Will's hand left her chin and tangled through her hair, something he had been aching to do for months. Emma parted her lips when she felt Will's tongue seeking access. Her knees buckled and Will secured his free arm around her waist, pulling her against him. As they broke apart, Will kept her close, resting his forehead against hers.

"Goodnight Emma," he whispered, and, after pressing a gentle kiss to her forehead, he was gone. Emma shut the door behind him and leaned back against the wood, her head falling back with a bang.