A/N: Hi everyone! This is going to be a sexier, naughtier fic than Home for the Holidays, my first fic which is still ongoing. Tell Me What You Want is pretty much going to be a PWP (plot, what plot?) taking place the summer before Elena goes off to college, after she tells Damon she loves him. I will be keeping this completely compatible with the show – I'd like to think this is what really happened that summer! Certain chapters may push certain people's buttons, so I'll post any warnings that might apply at the beginning of each chapter.

Warning: This one has some very light anal play.

"Tell me what you want," Damon whispered in her ear.

"Damon," Elena moaned helplessly underneath him. She was hot and sweaty and had come three times already today and still couldn't seem to get enough. Ever since Jeremy had taken off for Denver yesterday she'd been naked. Or half-naked, and then naked again. Damon seemed very against her putting her clothes back on…she had tried it this morning and had gotten as far as panties and a tank top before her insatiable boyfriend decided she was needed in his bed more than she was needed at Caroline's for a dorm room décor planning session. Not that she had minded…

Yes, sending Jeremy to Denver might have been Damon's idea (okay, it was totally Damon's idea) but he swore he hadn't used compulsion like the last time. In all honesty, Jeremy had jumped at the excuse to get away from them for a week or two. From Damon's perspective, Baby Bro was safe and sound visiting family several states away, and that meant he couldn't hear his sister screaming out her boyfriend's name in ecstasy at all hours of the day and night. These were the things that mattered, right?

Perhaps what mattered most was that Damon had an incredibly hot, incredibly horny girl who wanted him, and despite that she was leaving him at the end of the summer for college. So he sure as hell wasn't wasting the next couple months babysitting.

Elena lay on her back under him, her arms reaching around Damon and pulling him closer to her, their skin so slick with sweat that they were sliding easily against each other every time Damon thrust into her. He had put a couple pillows under her bum and at that angle was now managing to hit her g-spot with startling accuracy. Elena moaned his name again and again, turning it almost into a prayer as he took her body to new heights of pleasure. Damon leaned into her more and her pebbled nipples rubbed against his hard chest, reminding her of how earlier today he'd spent a full twenty minutes playing with her breasts, sucking, massaging, kissing, and pinching the sensitive globes, just working her up so that when he finally entered her he met zero resistance, her entire body already screaming for him. Her body was screaming now, but this time it was for a release from this almost painful state of arousal.

"Tell me, baby," Damon repeated. "What do you want?"

Elena cried out as he thrust into her again. "I want to come," she said. "I want to come, Damon, please!"

Damon was nothing if not cooperative (at least, when it came to a naked, writhing Elena) and he reached between their bodies to play with her clit. She burst apart almost immediately, shaking and screaming underneath him as she came violently.

Damon kissed her swollen lips and she kissed him back, their tongues moving together in a dance that the two of them had become very familiar with in the last three weeks. Damon loved kissing Elena. The kind of kisses they shared were rare, the kind where you could actually feel the other person pouring their heart and soul into you and into your kiss, the kind of kisses where you knew that nothing else mattered except the two of you.

Damon had stilled his movements inside her as they kissed, but now he pulled back slightly to give an experimental roll of his hips. Elena let out a long, slow moan, but she responded to his movements.

"How about now?" he asked her. "What do you want now?"

She groaned. "More."

Damon grinned. "That I can do," he said. "Do you want to be on your hands and knees?"

Elena nodded, and Damon kissed her forehead gently before pulling out of her and giving her room to scramble up and turn away from him. Her bum was pretty much flawless, round and pert and just begging to be touched, which Damon often did now that Elena was his girlfriend. He squeezed it through yoga pants when no one was looking, smacked it lightly when she was wearing nothing but lacy panties and they were alone, groped it through jeans when his hand was in her back pocket and she was talking to someone – Matt or some other human loser, didn't matter – and he was feeling just a little possessive. Because she was his honest-to-goodness actual girlfriend now. When was the last time he'd had a proper girlfriend? What were the odds that he was in totally over his head and was going to fuck this up royally? He didn't want to even think about it. All he wanted was to get his hands all over her now, while she was in his bed loving him and wanting him.

Damon gripped Elena's hips from behind her and positioned himself at her wet entrance, pushing his hard cock back inside of her. She arched her back and let out a soft whimper as he filled her again. He began rocking in and out of her slowly.

Damon looked down, watching his cock moving in and out of Elena's pussy, her hot, perky ass pushing back towards him. His hands traced the smooth curve of that ass, roughly grabbing her cheeks, which pulled them slightly apart, exposing her to him completely. Elena moaned.

He loved Elena like this, loved discovering more and more to this side of her that only two men before him had ever seen. That one of them was his brother was not something Damon liked to dwell on. Besides, he liked to think that he was bringing out things in her that no one else ever had. Let's face it, Matt Donovan was a puppy dog. And Stefan? Maybe he'd been around the block a couple of times, but he was practically neutered. No, Damon was determined that he was going to be this girl's true sexual awakening.

He ran his hands along her sides, stroking her soft skin. Enjoying the fact that he could touch her anywhere and everywhere and it seemed she'd only beg him for more. Which gave him an idea…

He leaned over and grabbed the lube from the bedside dresser. Not that they ever really needed it – all Damon had to do to get Elena wet was stare at her with his smoldering blue eyes – but it still spiced things up a little now and then.

"Damon, what're you doing?" she whined as she pushed her bum back against him, taking him in deeper and trying to regain his attention. He resumed his slow thrusts, popping open the lid and squeezing a small amount onto his finger before throwing the tube to the side. When he touched her a second later it was somewhere she'd only ever been touched once before and she jumped.

"Damon," she breathed. He circled his finger teasingly around the little hole, watching it tense slightly as she clenched around the cock that was still pumping wetly in and out of her.

"You can tell me to stop," he told her huskily, knowing she wouldn't. Damon had done this to her last week, just the one time since they'd officially gotten together after her graduation, though they had been having sex almost constantly for the past few weeks. They hadn't exactly talked about it afterwards, but her body and her reactions had told him several things without him needing to hear her say them. One, she was brand new to the pleasures that came with kinky, and two, him teasing her back door had turned her on more quickly and intensely than probably anything else he had done to her so far. And anything Elena loved, he loved doing to her.

He teased the puckered up hole, coating her back entrance with the lube as he waited for her to relax a little. The goal was to get her hot for it, so that by the time he plunged his finger inside she was under the impression that it was what she'd always wanted.

He loved knowing that his younger brother would never have dreamed of doing this with Elena. Stefan had treated Elena like she was breakable, while Damon's favorite pastime was finding new, delicious ways to corrupt his innocent angel.

He pressed himself firmly against the swell of Elena's ass, halting his thrusts and holding her still. She struggled against him briefly, but when she felt that thick finger begin to push into her she froze. Damon went only to the first knuckle before pulling back out. He lubed his finger up again and pushed back in, going a little deeper. Elena whimpered.

"You good baby?" he asked.

She made a noise he couldn't quite decipher, but he figured it was affirmative because she arched her back, pushing her bum up towards him like it was an offering. His mouth practically watered at the sight.

He finally slid his finger deep into her tight asshole, causing her to release a mangled cry and push back harder against his cock. Damon smirked, and decided it was probably a good thing Elena couldn't see his face in this position. He began to set a proper rhythm again, moving his finger in and out of her ass in time with his thrusts. He went gently at first, giving her time to adjust, but she was soon rocking back against him eagerly. Her body continued to beg him for more, and Damon always gave Elena what she wanted.

Elena met his thrusts with everything she had, rocking back and forth on her elbows and knees, her head down and hair falling messily all around her face. She was sweaty and hot and yes okay maybe even a little bit of a slut – she felt like it anyway – but she didn't care, all she cared about was what Damon was doing behind her. He was so deep inside her at this angle, and what he was doing with his finger…she never would have thought she'd let anyone do that to her. It was so dirty, but it felt so good. It made her want more, things that scared her and that she wasn't sure she wanted at all except for there was this need building up inside of her. She couldn't help the images that flashed through her mind – Damon on top of her, taking her in every way possible. It made her shudder with dark desire.

He fucked her roughly as he continued to finger her ass, going harder on her now because he knew it was what she needed. He wanted to add a second finger, but he'd only ever used one before and was worried it might scare her. He liked being the one to push her boundaries, but didn't want to push too hard.

Damon could tell how close she was from the near constant stream of whimpering and mewling noises she was making. She was pulsing around his cock now, and her little cunt was so wet that he was sliding in and out completely effortlessly. Just a little more and she'd be screaming his name. "That's it baby," he told her. "God you're so sexy. Do you know how good you feel? So wet and tight for me."

Elena moaned in response. He could feel the pressure building up inside him as well and he grit his teeth against it. He needed her to come first one last time. She was amazing, taking his cock in her pussy as his finger stabbed in and out of her dirty little hole, and she was loving every second of it.

"Such a good girl," he told her, his free hand digging into her hip to keep his thrusts even. "I need you to come for me Elena. All over my cock, baby."

She didn't need any more encouragement and she screamed out beneath him as her orgasm hit her. Her inner walls spasming violently around his dick was enough to send him over the edge too, letting her milk him for everything he had.

Elena's body shook beneath him, still experiencing the small aftershocks of her orgasm and he thrust a few more times for her, helping her ride it out despite the fact that his erection was waning now that he'd come. Before she'd fully recovered Damon took the opportunity to slide his finger slowly out of her ass. He leaned over her and kissed her shoulder blade lovingly once she'd stilled beneath him. Elena was breathing heavily.

"Baby, I'm pulling out," he said after a few seconds had passed. She nodded, and he did as he'd said, flopping down on the bed beside her.

Elena got up from the bed a second later to go to the washroom and when she got back Damon was nearly asleep, having used up most of his energy in their enthusiastic coupling. She slid under the covers and curled up on her side of the bed, feeling suddenly a little bit embarrassed and unsure. But her sleepy boyfriend pulled her closer to him and she told herself not to be weird. This was Damon, after all. If she couldn't be a little bit naughty with Damon, when could she ever? Elena closed her eyes, and she slept.

Elena woke up the next morning snuggled in Damon's arms. It was still dark outside, just before dawn, and she savored the warmth of the comfortable bed. Damon was spooning her and she could sense him waking up as well. There was the hint of a morning erection pressing against her bum and she smiled, wiggling back against it a little.

Damon groaned. "Evil woman." He kissed her shoulder sweetly.

"Dreaming about me I hope?" Elena replied with a smile.

"Mmmmm," he mumbled in agreement. "You and all kinds of naughty things." He gently rocked his hips forward a couple times, pushing his erection against her ass.

Elena felt it and last night came back to her as she felt a familiar stirring within her. They were both still naked, nothing between them and his cock was so close to that place he had been teasing last night with his finger. Her mind raced as her stomach was suddenly filled with butterflies. Was it something he wanted? Was that what his fingers were leading up to, what he meant when he said he was dreaming of naughty things? Was it something she wanted? What if they did that and it was terrible and it changed things? Was she completely crazy to be considering it?

Damon was still only half awake, but Elena stiffening rather abruptly beside him was pulling him out of his sleepy fog.

"What's wrong?" he mumbled.

"Nothing," Elena replied, trying to sound completely normal. Damon furrowed his brow, definitely more awake now.

"Elena, look at me, what is it?" Damon repeated, grasping her shoulder and pulling her around to face him. The room was all in shadows but he could still see she was biting at her lip, a habit he found insanely cute. It was what she did when she was nervous or uncertain.

"Are you okay?" he asked. He stroked her hip soothingly underneath the covers. "I know I was a bit rough last night, did I hurt you?"

She shook her head. "No," she mumbled. She was purposefully avoiding his eyes. "I'm fine, I'm just - last night was good, but-" she stopped.

"But…?"

Elena was obviously flustered and Damon had a hard time not smiling at how adorable she was in her discomfort, fidgeting nervously in his bed. He continued stroking her soft skin, hoping it was calming.

Instead of finishing her sentence she curled up against him, burying her face in his chest.

"I don't want to talk about it," she mumbled against his skin.

"Why not?" he asked, trying not to sound exasperated.

"Because," she huffed, looking up at him, "It's embarrassing." Her face was all flushed and she had morning after bedhead. She was gorgeous.

Damon persisted. "What's embarrassing?" he asked.

"The thing you did last night," she answered, hiding her face against him again.

Damon smirked. "Babe I did a lot of things last night, care to be more specific?"

She took a deep breath and went to start, but nothing came out. She tried again. Still nothing. Maybe by the time she found the words he would have drifted back to sleep?

"Elena?" he prompted.

Or maybe not. Maybe just get it over with?

"Are we- do you-do you want anal sex?" she squeaked, her face still hidden.

He smirked. "Are you offering?"

She glared up at him, cheeks flaming red.

"Okay, okay, I'm sorry. Why are you asking?"

"I just, I don't know what you're expecting and I don't know anything about kinky stuff and I'm sure you've probably done every single kinky thing that's ever been invented and-"

Damon interrupted her rant. "Now that is just not true. There are a lot of foot-related kinky things that I have absolutely no interest in trying. And at least two that involve a cat that I'm not especially keen on either."

She glared again.

"Okay, seriously. Elena, I would never push you to do anything you didn't want to," he said frowning. "I hope you know that."

"Of course I do, it's not that," she said, looking up at him. She was frustrated, she didn't know how to say what she was feeling or get out of this conversation without making a fool of herself.

"Then what?"

She buried her face back in his chest and he tried not to roll his eyes, though she wouldn't have seen it anyway. He forgot sometimes that she was still a teenager. He had to remind himself that she hadn't had one hundred and fifty years to become comfortable with her sexuality the way he had. He played with her hair while he waited for her to speak.

"I like that thing you do with your finger," she said finally, talking to his chest.

"Oh believe me, I know you do," he replied. She ignored him.

"Sometimes…when you're doing that it…it makes me want more."

He paused. "Yeah?" he said, aiming for casual. Elena had never asked him for anything like that in the bedroom, it was always Damon who led the way in that department. He waited for her to continue, but she didn't. "So when you say more, do you mean, like, a second finger, or more like a dildo, or-"

"Oh my God Damon I don't want to talk about it!" she shrieked at him, smacking his chest and trying to push him away from her.

"Whoa whoa, hey okay," he said, grabbing her wrists. "I'm just trying to figure out what you want."

Her heart was beating furiously in her chest and her eyes were actually shining. Christ, she was wound up tighter than a clock. He let go of her wrist and wiped away the single tear forming at the corner of her eye. "You don't need to cry about it," he said gently, placing a soft kiss on her lips.

"Ugh, I'm sorry I'm being so stupid," she muttered, wiping at her other eye.

She sniffed and his heart melted a little. "Shit Elena, you're not stupid. Look, I'm sorry I'm not good at this. I didn't mean to push you."

There were moments he was sure he was going to show her that he wasn't boyfriend material, that she'd made a mistake choosing him instead of Stefan. He'd spent so many decades trying to convey how much he didn't care that trying to do the opposite was something he struggled with now.

"I want you to take me seriously," she mumbled.

"Oh believe me, I take you very seriously," he said, wiggling his eyebrows at her suggestively, hoping to lighten the mood. She laughed, and sniffed again.

"Hey. I want to give you everything you want," Damon told her, running his fingers through her hair. "Whether it's sweet and sappy or unbearably kinky. Really. As kinky as you want. Try me."

She blushed and didn't meet his eyes. He could still hear her heart beating fast, and there was a familiar scent in the air. That slightly sweaty, totally female, 100% Elena scent that came from between her legs and told him just how badly she wanted him inside her. He knew she was holding herself back, turned on but afraid to show him how much.

"Elena?" he placed a finger under her chin, tilting her head up. He kissed her, deeply, and she fell apart in his embrace, letting him pull her closer and press up against her. He tangled his legs in hers, running his hands over her back as she moaned into the kiss.

"Damon," she whispered.

He slipped his hand between their bodies to touch her where he knew she needed him. He could smell her arousal easily, could see it in her eyes, but when his hand reached its goal and he felt how slick she was with want he still groaned.

"Does it make you wet thinking about it, Elena?" he asked her hotly, teasing her with his fingers. "Are you wet from thinking about what it would be like to have me fuck you in the ass?"

She whimpered at his words, pushing herself against his hand.

"It's okay," he continued. "I'm hard thinking about it. Thinking about you bent over, your ass in the air, completely at my mercy. God Elena, you'd look so sexy like that."

He found her hand under the covers and moved it to his cock, which was as hard as he said it was. He groaned when her fingers closed around him.

Damon slid his own fingers up and down her dripping folds. He moved his fingers deftly, working her clit with the kind of expertise that no college boy could ever compare with. He hoped she'd remember that at the end of the summer when she went off to Whitmore. She'd have the boys drooling all over her, but Elena was his and he was going to show her just how much.

"I think you are," he said, rubbing furiously. "I think you want me to bend you over and finger your tight little asshole. Stretch out your hole and get you nice and ready for my cock."

"Damon, oh my God," she moaned. She tried to squirm but he held her firmly in place, grabbing one ass cheek with his other hand. He massaged her ass at the same time as a finger moved from her clit to play with the opening of her wet cunt, just barely dipping in.

"You like being naughty for me, don't you baby? You like to pretend you're such a good girl all the time, but what you really want is for me to do dirty things to your body and make you scream. I could make it so good, Elena. You know I could too."

This was torture, she thought. Her face, her whole body was burning up and he was looking at her like he was ready to devour her. Every word sent fire through her bloodstream.

He kept going. "I could fuck your ass until you forgot that you'd ever liked it any other way, and then I'd make you come so intensely that you'd beg me to never stop." She believed him.

"Damon, please," she managed. He had two fingers inside her pussy now and was plunging them in and out at a pace that made her head spin. God she wanted him.

"Please what, baby?" He asked her, placing kisses on her neck as his fingers continued to work furiously between her legs. She was incredibly wet. "What do you want?"

"Not…that. I can't, not yet-I…please just-" She couldn't even think straight, but he understood because he silenced her with a reassuring kiss. He pushed her back into the bed without another word, moving on top of her and between her legs, which she spread for him eagerly.

Damon held himself closely above her, his eyes penetrating into her own, only her ragged breath between them. She shivered as he entered her pussy slowly, inch by inch, never breaking her gaze. "Damon!" she gasped.

"I know," he said, kissing her again. "Hold on, baby"

He pulled back and pushed into her forcefully, almost viciously, but it was exactly what she needed to feed the raging desire he'd built up within her belly. She moaned loudly as he pounded into her, and when he lifted her legs up and threw them over his shoulders she cried out, his cock pushing deeper into her than ever before.

"Oh my God, oh my God, oh my God," she chanted, grabbing onto the headboard.

"Fuck, Elena," he managed between gritted teeth. She was so wet, and her tits were bouncing up and down with every thrust. Every time he looked at them he felt he was going to come right then and there. He could feel her pussy clenching around him, sending him closer and closer and-

"Damon stop, stop," She protested underneath him, trying suddenly to wiggle away from him. "God it's too much, you need to stop."

He growled, but stopped moving immediately. He let her legs go and leaned forward to rest his sweaty forehead against hers. "Elena?" he questioned, out of breath.

"Sorry," she panted. "Just, I don't want it to be over yet."

She looked so vulnerable and thoroughly ravished lying underneath him, and he sighed and kissed her. He felt her emotions pouring out through her kiss in return, and he began exploring her mouth languidly with his tongue. She pulled him closer, and he tried to give her what it was she was silently asking for. She wanted him to reassure her, needed him to make love to her, not fuck her. Still inside of her but not moving, Damon stretched his body gently out on top of hers. They lay with their legs intertwined, sharing slow, passionate kisses as they allowed their heart rates to return to normal. Damon ran his hands over his girlfriend's gorgeous body, stroking her arms, her perfect hourglass curves, her long, graceful neck.

"You are the most beautiful creature," he whispered. She shuddered, and he caressed the side of her breast. "You are perfect," he continued, his face buried in her neck, lightly pressing kisses to her jugular. "There are so many things I want to do to your body Elena, so many things I want to make you feel."

"Damon," she gasped. He felt her clench around his penis, still hard inside of her.

"Do you want more, baby?" he asked. She nodded, and he pulled out of her slowly as she whimpered. She looked up at him confused, but he moved to the side and gently rolled her to face away from him. He molded his body behind hers, returning to the same position they were in when they first woke up that morning.

"Leg up," Damon ordered, and she did as he told her. He grasped the leg she'd thrown in the air, holding her open for him as he pushed into her again, this time spooning her from behind. She moaned, the feeling of him filling her like nothing else. He moved slowly at first, until she began grinding back against him shamelessly, letting him know she wanted more.

"I need you to play with yourself for me baby," he whispered in her ear. She obeyed without hesitation, slipping a hand in between her legs and rubbing at her clit. He listened to her gasping breaths as he continued to fuck her gently, building her up to a frenzy.

When she finally asked him for more he reached his free arm around her and grabbed one of her tits roughly, rolling the nipple between his fingers, pinching and pulling and driving her crazy. He knew just how she liked it.

"Damon – I – aaaah – Damon please." Her whimpers were desperate. He was hitting that perfect spot within her on every thrust and she felt like she were about to break apart into a million pieces.

"Come for me baby," he told her. "I want you to pretend I'm fucking your ass right now, not your pussy, and I want you to come."

She whimpered in surprise, but the embarrassment she felt was nothing compared to the way his words went straight to her blood, spreading heat throughout her whole body.

"Is that why you like being fucked from behind so much Elena?" he asked, driving persistently into her wet, trembling core again and again. She ground herself back against his cock helplessly, ashamed that Damon knew this secret of hers now, knew how to use it against her so effectively. His groin slapped against her ass with every thrust, and it wasn't hard to pretend it really was her ass he was fucking. The thought was both terrifying and unbearably hot. She could hardly stand how turned on she was, and she rubbed her clit desperately.

His gentle thrusts had become forceful and the bed was creaking under their efforts. Elena felt herself spiraling out of control as Damon worked her body expertly, whispering dirty things in her ear. "Have you been imaging it this whole time, Elena? Is that what you think about when you touch yourself? Do you want me to stick it in your hot little ass?"

"Damon!" she screamed as her orgasm ripped through her. It was the most intense, mind-blowing climax she had ever experienced. She felt her juices flowing out of her; felt them coating her inner thighs as she continued to shake in Damon's arms. Her vision blacked out for a second. When she became aware of her senses again she found Damon still thrusting into her, still holding her leg up to allow him access. Her abused pussy spasmed around him every other thrust and he was groaning as he pushed into her, trying to find his release.

"Damon, c'mere," she mumbled. She rolled herself out of reach of his cock and Damon actually whined behind her, a sound she'd not yet heard from the vampire who was usually so in control. She pulled him on top of her. While it was true Elena liked it best from behind, Damon was a missionary man all the way.

When he entered her again she winced slightly, but Damon had buried his face in her neck and was rutting against her in unusually uneven strokes, his breath unsteady.

"God that's it Damon," she moaned in his ear, urging him on. "You made me come so hard babe, you feel amazing."

He choked on whatever words he'd tried to say in response, and she smiled up at the ceiling. It was comforting to know that as much as he'd worked her up, he'd worked himself up just as much if not more.

"God I love the things you do to me. Can you feel how wet I am for you?" she cooed. "I love being so wet for you Damon. Come inside me, please, come in my pussy."

Her arms were wrapped around him, and she played with the hair at the nape of his neck as he continued thrusting into her. He was so close, she could tell. Just a litttttttle more.

"I want you to fuck me Damon," she moaned in the sexiest voice she could. "I want you to fuck me with that big cock of yours, bend me over and fuck my tight little ass until I scream."

"Oh my GOD Elena," he gasped, and he was pushing hard into her one last time, shuddering his release.

It was nice to know she had a little bit of power as well.

He was rolling off of her seconds later, and she leaned over and kissed his temple, curling her body up into the side of his body. He moaned. "Fuck Elena, you're incredible. That was…incredible."

She grinned with satisfaction and he glanced over at her. "Did you really mean that last thing you said?"

She blushed, but smiled. "We'll see."

A/N: Eeek! What did you think? I'd originally written this as part of the sex scene in Ch 3 of Home for the Holidays, and then I decided it had gotten racier than I'd intended. Other chapters in this fic won't necessarily include any more anal-related fantasies (unless you're interested, in which case let me know!) but I've got some fun role playing and public places ideas bouncing around in my head so even if this first chapter isn't your thing I hope you'll still stick around for more! Please review if you have a second, especially if you have any suggested fantasies you'd like to see me write about!