New chapter!

I already have some more written, so I'm hoping to be able to update pretty frequently.
However, this story won't be super long, maybe 10ish chapters or so.

Anyway, thanks to everyone who read and/or reviewed, followed, faved! You guys are awesome! :)


"The alphabet doesn't belong in math," Damon complained as he stared down at the mass of textbooks on the table, none of which were very helpful, "Polynomials and Quadratic theories aren't going to mean shit in the real world. This is why we have computers."

Elena was sitting next to him, her chocolate hair piled high on her head, an easy smile on her lips, "It doesn't have to mean anything. It just has to get you past graduation."

He grunted, and she tapped his paper, "You've got this, Damon. Just focus. Tell me where you get stuck."

Together, they worked the problem out, though it took him a few more tries to really understand the formula.

Having Elena so close to his side, smelling like warm vanilla, probably wasn't helping his concentration skills.

Especially given the fantasies he'd been entertaining about her all weekend.

It had been a surprise for him that morning, when she had cornered him at his locker at school, asking when their first study session would be.

He had tactically offered to start that very afternoon, and she had been all too pleased by the answer.

Part of him had wondered, after getting off the phone with her Friday night, if she would come to her senses and back out of their little arrangement, but so far she was still resolved.

In typical Elena Gilbert fashion, she was determined to see them both better educated, and wasn't going to take no for an answer.

Of course, it was the prospect of her education that was stealing his focus.

For years, everything about Elena had been off limits.

She was just his friend; the good little Gilbert girl.

His childhood playmate. Stefan's girlfriend.

She was fun to talk to at Founder events.

Fun to flirt with in the school halls.

Fun to tease when she was over at his house, visiting his brother.

But he had never considered that there might ever be anything more to her.

At least, not until she had kissed him the other night.

His mouth still burned with the memory and he couldn't look at her now and not feel the attraction.

He remembered all too well her pink, swollen lips teasing his own; her breathy inhale as his tongue brushed against hers; the soft curve of her body pressed against his.

At that moment, innocent little Gilbert had been anything but, and he was way too eager for the experience to repeat itself.

He wondered if she was too.

If, like him, she had been fantasizing over the possibility all afternoon, building up to these moments now, when they were alone.

Surely that was why she had suggested they come here, to her house, wasn't it?

Elena's parents, Grayson and Miranda Gilbert, were both doctors at the local hospital and were currently attending a conference in Richmond.

Since they weren't due back until Wednesday, the Gilbert house was practically empty, which made it the perfect place for "tutoring".

And once that was realized, Damon's interest in Calculus dimmed considerably.


"Alright, I think that's enough math for today," he decided, after forcing himself to finish the final equation on the homework.

Elena laughed, but took the page from him for a final examination.

"We got a lot done," she admitted, then arched a brow at him, "And I'm impressed. You aren't as stupid as you try to act like you are."

He grinned at that, closing his books, "My brother may be the nerd in my family, but I do have a working brain. And you give a much better math lesson than old Mr. Sullivan."

"Not exactly a hard feat to accomplish," she noted, giving him back the homework sheet, "Seeing as he tends to sleep away half the class at his desk."

"Our parents tax dollars, hard at work," Damon joked as she pushed out of the chair she had been occupying and stood up.

"I'll get us more snacks," she motioned to the backpack he had dropped on the floor when they had first started, "Did you want to start on English Lit now, or-"

"We've given academics an hour of our time," he reasoned, "How about a break?"

She nodded, "Alright. You can go in the living room and pick out a movie. Remote for the TV is on the coffee table. I'll bring food and drinks."

She walked out of the dining room toward the kitchen, so he did as she suggested and went the opposite way, to the living room.

The Gilberts were well off, as were most of the Founding Families, yet unlike the Salvatore's seven bedroom manor, Elena's house was more modest.

The flat screen was reasonably sized, and the furniture, while older, was not antique.

There were throw blankets on the sofa and magazines on the end table.

It was more homey, yet still...there was evident organization; an inelasticity that spoke of the rigid lifestyle her parents enforced.

And despite the differences, the environment had a similar reflection to the cold, dark walls of the stiff mansion he lived in.

Damon shook off the thought and took a seat on the couch.

Today wasn't about breaking down the details of their living strutcures.

He let his mind drift back to the situation at hand, as he waited for Elena to join him, and once again, that lingering anticipation began to build.


It didn't take long for her to come into the room, carrying a sleeve of cookies and two glasses, but when she saw him, she frowned.

"You didn't turn on the television."

"No, I didn't," he helped her place the haul down on the coffee table and waited until she was sitting next to him before saying, "Because you didn't really want me to. Did you?"

She straightened, clearly catching the meaning behind his tone, "There will be plenty of time for...all of that. I just thought we would watch something for now."

He smirked as her gaze focused steadily on the blank screen in front of them, and he couldn't stop himself from leaning over and whispering into her ear, "Really? You had no other plans, inviting me over today?"

Her eyes flew to his, and Damon saw the thinly veiled panic in them.

"Backing down already?" he challenged but pulled away, not wanting her to feel crowded.

She didn't say anything, which sobered him.

"Elena, we don't have to do this," he assured her, "If you're uncomfortable, we can end this whole thing now."

Again, she was silent, but her gaze fell, so he took that as confirmation and moved to stand up, "I can go, and we'll just-"

"No," the word was barely a breath, but it stopped him, and Elena's hand shot out, grabbing onto his arm, "No...stay."

Damon felt relieved, but studied her face, wanting to be certain she wasn't having second thoughts.

Elena tugged on him, dragging him closer, until he was back on the couch and she was at his side, as near as she could be without actually sitting in his lap.

And then she was kissing him.

He was better prepared this time, but just as she had on Friday night, Elena left him breathless.

Their first kiss had been so unexpected, that he had wanted to chalk up the intensity of it to the shock that it was happening at all.

But oh, he was wrong.

Because this was the kiss he'd been anticipating all day, and it still consumed him entirely, stealing every thought in his head that wasn't about touching her.

Elena took the lead, her tongue pushing through his lips and sweeping into his mouth, taking what little air had been left in his lungs.

He let her deepen the kiss, and her hands lifted to tangle in his hair.

She fisted the ends of it in her palm and as her teeth grazed over his bottom lip, Damon thickened beneath his jeans.

A fact Elena almost discovered first hand as she pressed herself further into him, one of her knees slipping onto his thigh and he wanted more than anything to pull her the rest of the way over; to have her straddling his lap as he thrusted against her.

But this wasn't about what he wanted...it was about her, so he would just have to calm down.


He had barely managed to get his thoughts under control when Elena pulled away, breaking the kiss.

She was panting a little, and he tried, and failed, to ignore the way her chest lifted with each inhale she took.

"So, what am I doing wrong?" she demanded, once they had both caught their breath.

"Nothing," he admitted without hesitation, "Like I told you on Friday, you know how to kiss, Gilbert. Hell, I could spend hours letting you do that to me."

He expected that to please her, but instead she sighed and sank back onto her side of the couch, "Then why is so much work to get Stefan to feel the same way? He doesn't kiss me the way he was kissing Caroline in that car."

Damon shook his head, "Forget about them right now. This kiss alone was hotter than Caroline Forbes on her best day, and Stefan's an idiot for letting you think you have to work for anything. It should be about pleasure, nothing else."

"Yeah," she agreed bitterly, "Pleasing my boyfriend so he won't leave me."

"I meant your pleasure," Damon argued, "You have to enjoy it too."

"I do," Elena insisted, but there was something blank in her expression, "I mean, I like kissing."

Damon frowned and studied her.

When she didn't add anything further, his brows pulled together in revelation.

She had no idea what he was actually talking about.

"Elena," he started, more gently this time, "Have you ever had an orgasm?"

The question was direct, but he had to know.

She blanched at him, then spluttered, "What? Of course I have! I mean...I...I think I have."

Damon shook his head, "An orgasm isn't something that you have to to think about. If you've had one, you'd know it."

Elena bit her lip nervously and he internally cursed.

Was Stefan honestly the biggest fool on the planet? His girlfriend was smart, beautiful, sexy, and one hell of a kisser...and she had never had an orgasm?

Had his brother not listened to a single thing he had told him over the years about pleasuring women?

Maybe he should be giving Stefan these lessons, instead of Elena.

No wonder the girl had wanted to wait on the whole sex thing; she had no clue what she was missing out on.

And he knew just how to rectify that.


Elena's doe eyes widened in confusion when he suddenly straightened to front face her completely.

"I want to try something," Damon said, reaching for her hand as he brought his legs up onto the couch.

She placed her palm in his and he pulled her closer to him, "Turn your back toward me."

Elena did as he asked, only a little awkwardly, and he adjusted until they were both lying long ways across the sofa, her back pressed to his chest.

"Get comfortable," he told her, not hating the feel of her body as she moved against him, finding the perfect fit for their contortions.

Once she was settled, her weight fell back into him and he wrapped his arms around her, "Okay, lesson one..."

He let one of his hands wrap around hers and guided it down her abdomen, stopping at the hem of her shirt.

With his lips against her ear, he whispered, "Unbutton your pants."

He felt Elena's muscles tense as her eyes widened, "Seriously?"

"Yes."

A frown, "Do I have to?"

"It is completely up to you," he reminded her, "But you asked for my help. Do you want it or not?"

Her lip got the chewing treatment again, and he waited for her nerves to win out.

But that's not what happened.

Instead, Elena's hand left his and fumbled over her pants button, and she undid the thing.

Damon had to bite back a groan as he caught a flash of the pink silk she was wearing beneath, but then Elena was leaning back to look up at him, and he had to focus.

"Now what?" she challenged, with only the slightest movement of her throat as she swallowed giving away her nervousness.

Damon sank further against the armrest he was propped up by and reminded himself that this was strictly for her education. Nothing more.

However, that didn't stop his gaze from roaming down the length of her body, before he reached out his hand, "Give me your palm."

Hesitantly, Elena placed her hand into his again and Damon squeezed her fingers, "Do you trust me?"

She inhaled slowly, her hair tickling his neck, "I probably shouldn't...but yes."

"Then try to relax," he turned his head to kiss her temple, "And I'll show you how good it can be for you. Okay?"

He waited for her to nod her consent, before moving his hand to the back of hers and guiding it.

First, he trailed their fingers down her neck, then over her chest, slowly grazing over each mound.

It wasn't likely she was feeling much sensation through the bra she was wearing, but he was hoping the intimacy of the touch alone would get her head in the game.

A minute later, her hips were shifting unconsciously, and he knew he'd succeeded.

He left her breast then, and moved them back down her stomach, to the waistline of that pink silk beneath her jeans.

"Have you ever touched yourself?" he whispered, pressing his forehead against her hair so that the words brushed her ear.

Elena shook her head, "No...not like this."

He had figured as much, "We'll go slow."


He pushed their hands into her panties, and brushed over her slit.

They both gasped at the contact.

God, she was wettening already and the tips of his fingers were suddenly coated with her warmth.

He breathed for a moment, then began to move them in small circles, forcing hers to follow the same motion, and Elena's head fell back against his shoulder.

After a moment, she moaned, and the sound went straight to his already hardening cock.

What he wouldn't give to rip away that denim, flip their bodies, pull her underwear aside, and bury himself deep within all that slick heat.

But this was all for her, and he was nothing if not giving, so Damon forced himself to ignore the straining pressure in his own pants and increased the speed of their hands.

When he rubbed against her clit, Elena's fingers left his, moving instead to dig into his forearm, nails scoring deep as her hips jerked.

"Damon," she rushed out, her body straining for release, and her head turned up toward him in an invitation so irresistible, he had to kiss her.

The second their mouths met, she moaned again and the sound echoed down his throat.

With the skills learned from years of experience, Damon worked Elena with his fingers until she was shivering from the build up.

He edged her, closer and closer, slowing down, speeding up, drawing out the pleasure for as long as possible.

When she breathed his name against his lips in a whimper, he took things even further and let a single finger slip inside of her.

Her cries grew louder and there was no sound more lovely in the entire world.

"Come for me, Elena," he purred as her muscles began to clench. Half commanding, half begging.

And her entire body responded.

Her hips shot up as her core tightened around him, and her legs scissored slightly as he kept moving his fingers.

Her mouth left his and she buried her face into his neck instead, her teeth leaving indentations just below his jugular as she bit down her cry.

Damon let her ride it out before extracting his hand, and Elena flinched at the loss of connection before sagging in his arms.

Her face was still hidden in his neck as she breathed deeply, but he could see the corner of her mouth turned up in a smile.

His chest tightened with a hint of smugness.


Elena couldn't believe that she had just let Damon Salvatore finger her, on her living room couch no less.

But what was even more unbelievable was what had happened in her body because of his touches.

He was right, damn him.

An orgasm wasn't something you would ever forget, and she had never experienced anything like that before.

She took another settling breath, then lifted her face so she could see him.

Damon's self-satisfied smile matched her own and she reached up to touch his lips.

"That was…" she couldn't think of an adjective good enough to encompass what he had just done to her, but lost her train of thought when his mouth parted around her fingers.

His tongue swiveled out, licking away the damp aftermath of their activity, and it was so erotic to know what he was tasting, that she felt her body respond with more of that wetness.

Damon's eyes met hers and he seemed to read her mind, because he released her hand and licked his lips.

"Do you have any idea how good you taste?"

She blushed, "I…"

"Here," he tilted his head and kissed her.

Just like before, she felt an electric current flash through her body as their lips pressed together.

Damon's tongue wasted no time forcing its way inside of her and she immediately understood what he meant.

She could taste herself on him, and though it was a faint flavor, it screamed of all things private and wanton.

Wanting more, she reached up and grabbed the back of his head, deepening the kiss.

Damon obliged, shifting them until she was beneath him on the sofa, and his body hovered between her parted thighs.

Then his kiss moved to her neck, trailing up to her ear where he said softly, "And that was with all of your clothes still on. It only gets better from here."

"Better than this?" she couldn't hide the disbelief in her voice.

Surely there was nothing better than what she had just felt...was still feeling, in the core of her stomach.

Damon smirked, "I'll show you more, don't worry. But for today, we'll end the lesson with this. You have to know what pleasure is in order to give it to someone else, so practice. Find out what you like, what you don't. There's no shame in learning your own body."

When she nodded, he gave her a final kiss, then sat up, moving to the far side of the couch.

She followed his example and straightened up herself, redonning the button on her pants.

"Why don't you go ahead and put on that movie," Damon suggested, "I think we can both use the distraction."

She laughed quietly, "I think that's a good idea. Assuming my legs are done shaking."

His smile broadened as his eyes moved to her thighs, "Don't worry; they'll recover."

Then he was standing, and Elena frowned, "Where are you going?"

He motioned toward the hall across the room, "Bathroom. Unless you'd prefer I take care of the...side effects right here?"

It took a second for her to realize what he meant and when it clicked, her eyes fell down to his waist.

Sure enough, there was something below his belt that was screaming for attention, and she couldn't help but smile.

"I did that."

Damon chuckled, "Yeah, sweetheart. That is all because of you."


The smile didn't leave her face as she turned to let him go take care of business and focused on finding the TV remote.

Once she had, she turned it onto some random channel and brought her legs up as she waited.

Damon joined her a few moments later, absent his little, or not so little, problem.

And together they laid back out on the sofa and pretended to watch the movie.


It was after eight when Damon got home, and he wasn't surprised to find the house quiet.

His father was probably upstairs in the study, where he had practically lived since Damon's mother had left him a decade ago.

The boys knew better than to interrupt him, and to be honest, Damon had long since lost the desire to ever converse with the man anyway.

Upstairs, Stefan's bedroom door was open, but he could hear nothing from inside.

He found out why when he opened his own door.

His brother was sitting on the edge of the bed, fiddling with his phone as he obviously waited for him.

"You're in the wrong room," Damon announced himself, and Stefan looked up.

"Hey, you're home!"

"And you're on my bed," he pointed out and Stefan laughed, "Yeah, I was waiting for you."

No shit.

He kicked off his shoes and started stripping out of his jacket, "What's up?"

"You were studying with Elena today, right?"

Damon paused, "Yeah. She's helping me with Calculus. Why?"

"No reason...just…," he rubbed the back of his neck, "Did you say anything to her? To Elena?"

Damon paused, "About what?"

"Me," Stefan said, as if it were obvious, "About me and her? And what happened Friday."

Damon schooled his expression before turning to face his brother, "What happened Friday?"

Stefan rolled his eyes, "Oh come on, man. I told you. It was all a big misunderstanding, and-"

"And your dick accidently found its way into Caroline Forbes?" Damon challenged, "Good thing you want to be a doctor and not a lawyer. You don't make very compelling arguments."

Stefan's face went cold, "It's not a lie. I told you, we were just drunk...and it was just meant to be a little fun. It was barely cheating; we didn't even finish-."

"But you would have," Damon called him out, "If Elena hadn't busted you first. And news flash, fucking someone that isn't your girlfriend is cheating."

Stefan sighed, "It was just the one time. I didn't mean for it to happen. I just need the chance to explain that, but Elena isn't talking to me. What if she breaks up with me?"

He scoffed, "Should have thought of that before you hooked up with her best friend, don't you think? Tends to upset most girls. Hell, we should know that better than anyone, or have you not learned from our father?"

Stefan shook his head, "This was different. Dad cheated on mom over and over and-"

"And she left," Damon pointed out, "A lesson well taught, don't you think?"

With more theatrics than necessary, Stefan threw himself back onto Damon's bed.

"This isn't like that. Just...tell me what to do."

He dropped an arm over his eyes, "I tried calling, then texting. I apologized, I gave her space, I begged her to talk to me...I don't know what else there is."

Damon fought back an eye roll of his own and exhaled slowly, "Forgiveness isn't a laundry list of things you can do to win her over."

"But...there has to be something I can do or say to her? You're good at this stuff with girls; so tell me how to make her forgive me."

His brows were pulled so tightly over his eyes that Damon worried he might pop a vessel in his forehead.

Typical Stefan, to feel so entitled after being the one to fuck up; that apple really had fallen right next to the tree, hadn't it?

"Please," Stefan added, "I don't want her to end it."

Wow. There was actual concern in his voice.

Damon was tempted to tell him to shove it; or to go reflect on why he had cheated in the first place if the relationship meant that much to him.

But then Stefan bit his lip, and looked so young and lost that he had a rare moment of compassion for his younger brother.

"She isn't going to break up with you, idiot," he said tiredly.

Even though she should.

"You hurt her and pissed her off, so now she's making you wait," he explained, "It's what women do. And after Friday, you deserve it. But trust me, she doesn't want to break up with you."

Stefan sat up, looking hopeful, "Are you sure? Did she say something?"

Yeah, Damon thought bitterly, My name, over and over, as she came on my fingers.

His fist clenched at the memory.

"Not a lot. She mentioned she was pissed at you, but she's planning on talking to you soon. Just leave her alone. Let her be mad for a bit."

Even though she certainly hadn't seemed angry earlier.

In fact, she had been quite the opposite as they had laughed at the cheesy rom-com she had picked out and fought over the last cookie.

"Thanks man," Stefan said, hitting his shoulder as he walked by, "If you see her again, tell her I'm sorry, will you? And to text me."

"Sure," Damon said.

I'll get right on that.


Elena showered and brushed her teeth before crawling underneath her blanket and grabbing her phone from the nightstand.

She had half expected Damon to text her, but only had a notification from Stefan.

Leaving that conversation for tomorrow, she pulled up the oldest Salvatore's number and quickly texted out a message.

E: Thanks for the lesson. When is the next one?

She held her breath as she waited for his answer, and thankfully, it came quick.

D: So eager for more math?

This asshole.

She smirked to herself and sent him the middle finger emoji, before receiving a second text.

D: The equations were quite enthralling. We will have to plan for part two soon.

Yes. They really would, she thought, as her phone beeped a third time.

D: Stefan was asking about you. How long are you planning on torturing him?

Elena sighed.

E: Very soon. And just until tomorrow...or the day after. You said to let him fret.

Again, the reply was fast.

D: Good girl.

For some reason, his response brought a blush to her cheek and she recalled, with perfect clarity, their moment downstairs earlier.

Damon had made her feel things she hadn't even known were possible, and she couldn't wait to feel them again.

E: I didn't know it could be like that.

She wrote with no extra context, but Damon's mind still seemed to be on the same wavelength as hers, because he answered back shortly:

D: It should always be like that.

She shivered as more recollections filled her mind.

E: I want to do that again.

Another fast reply.

D: Then do it now. For homework.

She laughed.

Of course Damon would suggest that.

And maybe, just maybe she had considered it...but no...she wasn't going to do that now...it would be weird, wouldn't it?

He had said that there was no shame in learning your body, and it had felt amazing when he had made her touch herself, but everything good and proper from her upbringing said that it was wrong.

Taboo, even.

Her phone beeped again. Another text.

D: I dare you.

Elena swallowed and sent one back.

E: You dare me? Oh please. We aren't twelve.

They absolutely were not, and she wasn't going to be swayed by a childish challenge.

Yet, for some reason, Elena found herself slowly reaching a hand beneath the blanket, until she felt the top of her underwear.

Unwilling images of that earlier evening played through her mind and for a moment it was as if Damon were still there, pressed against her side, breathing in her ear, guiding her hand with his own.

She took a deep breath...and slipped her fingers inside.


Getting a little more citrusy with this lemon ;)

More sexy scenes to follow! Hope you guys enjoyed!