So a couple of weeks ago I reblogged on tumblr a list of numbers with smut prompts. I received a ton and I'm slowly working myself up those ask. I had two anons asking for #6 Clothed getting off and one of them asked for #3 First time as well. I started working on those two numbers and my muse got carried away and this drabble turned out to be two-shot. So the first part will be written based on #6 and the second part on #3 (which should probably posted tonight or tomorrow morning).

I hope you all like it!

Oh and it's not edited so ignore the mistakes.

Another school year was starting off and Emma wasn't feeling very enthusiastic this year. Her friends Ruby, Mary Margaret and David were not going to be in any of her classes and that fact alone was enough to put a frown on her face on the very first day.

She entered her classroom and scanned the room looking for at least one familiar friendly face and when she saw none, she walked towards the front of the class and claimed a desk in the first row since all the others have already been taken. Awaiting for Professor Sloan to enter the room, Emma decided to get a better look at her classmates and cursed to herself when she realized that it was filled with jocks, Regina and her pawns, a couple of troublemakers such as Killian Jones, and a few low key students like her. She mainly recognized Tink at the other end of the class who was doing pretty much the same as her, and both smiled timidly at each other.

When Professor Sloan entered the class, she quickly remembered why kids in the school called him Professor Slow: he was old, talked slowly and had no authority with his students. Her classmates quickly started to talk all over their teacher as he attempted to explain the curriculum for the first semester. When Killian Jones raised his hand and made a pretty rude comment about their teacher being boring and making the rest of her class laugh she sighed heavily as she wondered how she was going to get through this year.

The first couple of weeks passed by and Emma realized how school had become more or less bearable. Outside of class she was happy and enjoying having a social life with her small group of friends. But as soon as she walked into one of her classes, a knot in her stomach appeared and dreaded the next few hours that were about to come.

Tink had made things a bit easier, she was as uncomfortable and unhappy to have been put in that class and they quickly became friends as they both tried to get through their day. As the weeks went by, their respective group of friends started to hang out together, that's how she met Neal.

Emma instantly felt this attraction towards him, but felt awkward on actually making a move on it. Despite her confident exterior, she did feel kind of shy and insecure when it came to her looks. She was almost seventeen and she still didn't had the chance to kiss a boy (not even a small peck) and she started to wonder if she would ever get the chance to. She knew that she wasn't bad looking, but she also didn't feel like she was the most beautiful girl out there. Emma automatically let her feelings for Neal on the back burner and let herself pursuit a friendship with him knowing that it was impossible for him to ever flirt or show any signs of attraction towards her.

The days slowly started to blend in together as the semester went on. Emma appreciated her new routine, taking the bus alone in the morning as she listened to her music as she watched the scenery pass by her. Arriving at school she spent at least half an hour with her group of friends before heading to her classes with Tink as they supported each other.

Their classes unfolded the same way each day, Regina giving them the stink eye as she gossiped with her friends, the jocks screaming and slapping each others back and Killian Jones would turn around and wink at her each time her reaction being a roll of her eyes and then at least once a day, he would be sent over at the principal's office. Then came lunchtime and Emma had an hour and half to enjoy the company of the people she appreciated the most.

One morning as she got in the bus, headphones covering her ears as the music clouded her mind, she sat on a empty seat near the window sighing as she watched the buildings pass by her. Emma didn't pay attention to the person sitting in the seat next to her until she felt a tap on her shoulder. She turned around and couldn't help the shock look that must have appeared on her face when she realized that Killian Jones was sitting next to her as he gave her a toothy grin.

Emma dragged her headphones down until they hung around her neck and looked at her least favorite classmate with a confused look.

"What do you want?" She asked him harshly which earned her a deep chuckle from him, annoying her even more.

"How about 'Good Morning' first, eh Swan?" Emma tried to suppress the new and unexplainable flutter that his accent mixed with the way he looked at her had stirred in her, his blue eyes sparkling with a hint of teasing in them.

"Good Morning, what do you want? Is that better?"

Once again, Killian smirked at her less than welcoming greeting and shuffled on his seat as he got himself comfortable.

"There could be less hate in that tone, but I think it'll do for now. As to why I'm doing here, well I'm taking the bus and this was the only free seat. I thought it was quite obvious."

Emma looked around and noticed that the bus was in fact full and looked at him once more before quickly avoiding his gaze as she murmured a 'whatever'.

They sat in silence for two stops before Killian decided to ask her random questions about their classmates and what she thought of them. Emma kept her eyes on the window next to her as she tried to appreciate the scenery but found it hard when he wouldn't get the hint that she didn't want to talk to him.

"Don't want to answer? Fine, I will." As he took in a deep breath, Emma swirled her head around and blurted out the question that she have been asking herself ever since she saw him in the classroom.

"Why are you such a jerk?"

His thick eyebrows shot upwards as he gave a shocked look. Emma let out a groan seeing how he was mocking her and decided to stop being polite. She put her headphones back on and crossed her arms in front of her chest as she turned her head to look back outside. She knew she couldn't enjoy the rest of the bus ride as she usually did as her body was now all tense and the company beside her making it hard to get rid of the frown that had settled.

His fingers tapped on her shoulder once again as Emma turned her head to look at him with an aggravated look. Killian had an apologetic face, one that she never thought was possible as he gestured her to take off her headphones.

"Look, I'm sorry Swan." He started off as he then paused to look around him as he quickly let his tongue moist his lips before looking at her again. "You want to know why I'm such a jerk?"

Emma was taken aback with the sudden honest look he was given her, and the way he had ask her if she wanted to know why he acted that way was devoid of mockery or any teasing tone, a side of him that she had never seen.

She locked her eyes with him briefly, instantly looking away as the intensity and blue of his eyes were too much for her. She nodded her head, and tried to look at him without meeting his eyes.

"I act like a jerk because I don't want to be here. I don't want to be at this school and I certainly don't want to be in this town. I'm telling myself that if I become enough of a nuisance, I'll be expelled and my father won't have any other choice but to send me back to England where I really want to be." He finished talking as he awaited for her reaction.

Her mouth parted slightly as she finally took the courage to lock her eyes with him and saw nothing but raw honesty.

"Is that what you wanted know?" He asked her, Emma letting out a soft 'yes'.

They arrived at their destination minutes later, both disembarking together as they walked side by side with a heavy silence between them. As they entered the main hall together, Emma wondered what to do now, not knowing if she should just leave without saying anything.

"See you later Swan." Killian told her as he pulled her out of her musings before heading out towards his locker.

Emma watched him walk away for a brief moment before walking towards her own locker and then meeting up with her friends.

-/-

Since that day her morning routine changed. She took the habit of taking the bus with Killian and after a couple of weeks she even saved the seat next to her. Emma still was baffled with the friendship (or whatever she could call it) that had blossomed between the two of them, but she looked forward on talking to him each morning.

They talked about everything, their conversations (more like playful banter) was filled with sassy comebacks which sometimes led them to laugh pretty damn loud. At school, things didn't change much. He kept being this asshole, but the difference was that everytime she looked up at him, he gave a her a soft smile. Her classmates didn't notice it, not even Tink, and she liked that she had this secret relationship with him. She felt privileged to see another side of him, one that she hoped was his true nature and not the façade he had in school.

Some time after the Christmas vacations, they started to have those silent conversation between them. She understood quite fast what one look meant, and sometimes Emma ended up quietly chuckle in her corner. Each time she looked back up, she saw this proud look on his face, one that told her he was quite please with himself that he managed to make her laugh. Those moments made her days less dull and awkward.

Things changed also changed with her group of friends as they now always hung out with Tink and her friends. That meant that she had the chance to spend more time with Neal. Emma couldn't deny that crush she had for him, especially since he always managed to sit next to her and gave her one of those smiles, the ones that made her cheeks flush and butterflies party in her stomach.

Mary Margaret was positively sure that Neal had a thing for Emma. She had her doubts, as she always did, but there was this feeling in her gut that told her that her overly optimistic friend might be right. That thought alone was strong enough to made her heart swell and ache at the same time. The need to know if it was true and the crippling fear of being turned down was sometimes overwhelming.

Emma saw an opportunity to see Neal outside of school when they heard a rumor in the hallways that Regina was throwing a open house at her parents mansion. The rumor was confirmed by Killian the next morning and she wasn't surprised when he told her that he would be attending.

She wasn't sure if she wanted to go, never being one of those party people since she much more enjoyed staying at home and watch a movie. Ruby on the other hand, really wanted to go and insisted on them to join her. Emma felt more compelled to go when Neal said that he would be going.

That's how she ended up at the party, overwhelmed by the amount of classmates that decided to show up. Emma stayed close to her friends as they grabbed a cup filled with punch. She didn't know what to expect from her evening since she never went to parties but she at least thought that they would all hang out together.

How wrong she was.

After an hour she found herself alone in one corner after Ruby started to talk with another student, Victor, a guy she sometimes caught glimpse of. Mary Margaret and David were cocooned together in one of the seldom free couches, and well Neal, he was apparently quite taken with a girl that she knew was named Tamara.

Emma took another sip of her third cup of punch and looked around her wondering why she was still there. Oh right. Mary Margaret's father was their lift.

She let out a deep sigh as she tried to keep the tears at bay as she tried to keep her eyes from landing on Neal (which showed her how weak her self-control was). Suddenly, someone came to stand next to her as she didn't even bother to turn around, not interested on having company.

"Why the long face?" She instantly recognized the voice, and only then did she managed to look at the person standing next to her.

Killian had a concerned look molding the lines of his face. She felt herself crack bit by bit when she felt his warm hand squeeze her shoulder in a reassuring way. Emma took in a shaky breath as the tears started to roll down her cheeks.

He quickly grabbed her hand as he pulled her towards the corridor, his arm then curling around her shoulder as he dragged her in one of the many empty rooms of the mansion. The room was dark, the only light present was the one seeping through the windows, the room lighten by the moon. Killian walked over to the nightstand to turn on the small lamp but stopped when Emma told him not to.

"I don't want you to see me crying." She told him as she sobbed.

She heard him sigh as he then slowly made his way up to her. His arms went around her as he pulled her in a comforting hug. She nuzzled her face in the crook of his neck, tears leaving his shirt damp. One hand caressed the back of her head while the other caressed her back as she let her emotions take hold of her.

"Do you want to tell me what happened?" He whispered in her ear, his voice soothing and concerned at the same time.

She shook her head on his chest as he then grabbed her shoulders and leaned her back to see her. Despite the room being dark, she could still see the lines of his face and her heart clenched as she noticed the worried look he was giving her.

"I'm a fool." She murmured.

Killian cocked his head to the side, clearly wondering why she would say something like that.

"You're no fool. Why…" Emma cut him off before giving him the chance to ask her why.

"I am. How could I have been so stupid and think that a guy could actually like me? Am I that unlovable?"

The questions slipped out of her lips, but she didn't expect him to respond. Instead she looked down as she took in a ragged breath.

"Why would you think such a thing?" His hand went to cup her chin and lifted her head slowly so would look at him even in the darkness.

"You are wonderful Emma and any other bloke that tells you otherwise is a damn fool. Listen to me Swan, you are stunningly beautiful."

Her breath got caught in her lungs as she heard him say those words. Before she knew it, she leaned in as her hands went to cradle the back of his neck, as she pulled him in a soft kiss. She didn't know why she did it, but she needed it to do it.

"Emma…" He murmured on her lips before she pressed them against his once more, this time a tad more insistent.

"Don't talk, just kiss me." She whispered back, he didn't need to be told twice.

It was then that she had the sudden realization that she was being kissed for the first time, and she honestly didn't care that it didn't happen the way she wanted to be when it felt so damn good. Killian tilted his head to the side as he deepened the kiss as he sucked on her upper lip, a soft moan slipping out from her.

Her fingers grasped a fistful of his hair while his hands trailed down her back, and she could feel his fingers twitching to cup her ass. She pressed her hips on his, the action making him groan, the sound giving her more courage to do what was next.

She turned them around and blindly guided them towards the empty bed until the back of his knees bumped the edge of the bed. Killian took the hint and sat on the mattress as he guided Emma on his lap. He nibbled her bottom lip, silently seeking permission to push the kiss forward. She opened her mouth and let his tongue caress hers, the sensation so exhilarating that she didn't even know that her hips started to press down on his, her clothed core grinding on his bulge.

Emma broke the kiss as a loud and unexpected moan slipped out, her hands now clutching at his shoulders as she tried to seek more of the sensations that their actions was giving her. Killian's mouth went to her collarbone, softly yet desperately kissing the exposed skin as she kept pressing her bundle of nerves on his straining erection.

She was not unfamiliar with the building sensation of an orgasm as she occasionally explored herself in the intimacy of her bedroom, but having that thrill build this way, with another person was a whole other thing.

"Oh God." She panted when Killian thrusted his hips up, as he let out a moan in the process.

"Emma. Oh, Emma." His voice was strangled, and hearing how much this affected him as well was enough for her to reach that blinding peak, as she let the feeling roll down her body.

Her forehead went to rest on his as she felt her body go limp. Her breathing was now slowly returning to its normal rate, but quickly noticed that Killian wasn't.

"I..did you..?" She trailed off and felt Killian shake his head.

"No. I was close though." Emma suddenly felt bad, and she would blame the haze and alcohol clouding her judgement for the words that came out of her mouth next.

"Can I do something?" She heard him trying to reply as he stammered a jumble of words.

Her recent high gave a boldness she didn't knew she possessed and lifted her hips a tad and unbuckled his pants as she temptatively cupped his erection. Killian sucked in a breath when she did, and was submerged with this empowering feeling. Her shaky fingers pulled the fabric of his underwear low enough for his cock to slip out of it. The room may be dark and made it difficult to see his erection (which she was quite curious to see what it looked like) but settled for feeling it.

Emma's heart started to race once again when she curled her hands around him and was impressed on how hard he was in contrast with the silky skin. His hand went to cover hers as he silently showed her how to move her hand around him, and found out quickly how easy it was to slide her hand up and down, squeezing lightly around it until he was gibbering mess.

A silent cry escaped his lips as his release spurred on her hand, some of his seed dripping on down his shaft. Emma looked at her hand, still in shock on this moment ended, clearly not expecting this (well she didn't know what to expect). When Killian finally managed to open his eyes again, and saw her staring at her hand, his fingers curled around her wrist as he softly apologized.

"It's okay." She mumbled before getting up and making her way to the adjacent bathroom. ç

She turned on the lights, the brightness a contrast to the darkness of the room she was previously in as it made her eyes squint for a brief moment. Emma washed her hand and when she was done, looked herself in the mirror.

Her hair was dishevelled as his fingers kept running through her locks, her cheeks were tinted pink, her lips red and swollen. That's when the realization of what they had just done dawn on her. An intense need to flee overcame her and made a quick move to dry her hands and got out of the bathroom as quickly as she could.

Killian was waiting for her in the bedroom in which they shared their intimate moment, the room now lighten with the small lamp next to the nightstand. He looked as wrecked as she was, his hair pointing in every direction, his cheeks as pink as hers, lips also red and swollen. She had this need to kiss him again, wanting to feel every parts of him on her, but fear was more prominent as she started to chastise herself for everything she had done with him that evening.

"Thanks Killian but I need to go." She said hastily and her heart ached when she saw the disappointed look on his face, as he hoped to at least talk with her about whatever happened a couple of minutes early.

"Emma listen…"

"Sorry, but I really need to go." She told him as she walked out of the room as fast as she could.

Once she rejoined the life of the party, she saw her friends now all hanging out together and went to them as if they were her lifeline. She kept her eyes fixed on her group of friends, grateful that most of them were sloshed so they didn't noticed her flustered state, and she waited for the next half hour to pass by, when they would finally be able to leave the party.

Emma went to bed that night exhilarated, sad and confused. She still felt self-conscious for having feelings for Neal, knowing that they wouldn't be reciprocated. At the same time, she couldn't help but relive the moment she had spent with Killian. Who would've thought that Killian would have been her first kiss, and her first guy to give her an orgasm. Her heart rate increased as she thought of him, and felt confused on what she felt for him.

He was her friend, there was no doubt about that no matter how unconventional their friendship may be. She would also be lying to herself if she didn't admit that he was handsome, charismatic and sexy, and that at one point during their numerous bus ride, she wondered what it would be like to have something more.

Emma groaned in frustration as her arms hit her mattress. She still had Sunday to figure everything out and decide what to do and say when she was going to see Killian on the bus on Monday morning.