This took me forever!! My wrist is so sore but worth it for my incredible friend @l-xapr0, my Tadc screenshot redraw of the bar scene from Tadc episode 5
This took forever and I dident add kinger but I hope you still love it, (my hand hurts)
Extra tags: @cgsdraws, @artemisiamasterofnone, @twistedlikeness1, @plague-crane, @porceiaincat, others :3
This one’s for @elenavampire21 💋
You asked for Damon, flirting pushed right past the edge, and yes — there is smut (you know I wouldn’t ignore that 👀). I had way too much fun letting this date spiral exactly the way it was always going to. Hope this hits the way you wanted — and then some. Wink wink.
It’s late in the Salvatore house in that way that never feels fully asleep.
The lights are low, warm instead of bright, shadows soft along the staircase and the old portraits. The house smells like bourbon and wood polish and whatever Damon opened and didn’t finish earlier. You’re curled on the couch with your legs tucked under you, bare feet cold against the leather, wearing one of Stefan’s old college sweatshirts and a pair of jeans you meant to change out of hours ago.
You weren’t planning on being seen like this.
Hair loose, no makeup, nothing deliberate about you at all. Just comfortable. Existing.
Stefan disappeared upstairs a while ago, books in hand, leaving you alone with the quiet hum of the house. You’re flipping through a worn paperback you’ve read before, more habit than focus, when you hear footsteps coming down the hall.
You don’t look up at first.
Damon stops when he sees you.
He doesn’t say anything right away. He just leans against the doorway, arms crossed, eyes slow and knowing in that way of his. The kind that’s been lingering for years now. Too long. Long enough that the flirting stopped feeling like a joke and started feeling like a promise nobody was brave enough to name.
“Well,” he says eventually, voice lazy. “If I knew this was what hanging around my house got me, I’d have kicked my brother out ages ago.”
You glance up, arch a brow. “You’ve been flirting with me for a century, Damon. Don’t act surprised now.”
He grins, sharp and familiar, and pushes off the wall. Each step toward you feels deliberate, measured, like he’s testing something. He perches on the arm of the couch instead of sitting properly, close enough that you can smell the bourbon on him, faint and warm.
“You look comfortable,” he says.
“I am.”
“Dangerous thing, being comfortable around me.”
You close the book and set it aside, turning your body toward him just slightly. “You’ve never complained before.”
Something flickers in his eyes at that. Not hunger exactly. Consideration. Like he’s standing on the edge of a decision he’s been circling for a long time.
The silence stretches. It’s not awkward. It’s heavy.
You’re used to Damon touching you casually—brushing past, leaning in too close, murmuring things meant only for you. Tonight, he doesn’t touch you at all. His hands stay still, his posture tense in a way that feels new.
“You busy tomorrow night?” he asks, too casual.
You blink. “Depends.”
He tilts his head. “On what?”
“On whether this is another one of your almosts.”
That earns a quiet laugh. Not sharp. Not mocking. Real.
“No almosts,” he says. “I’m asking.”
Your heart stutters, traitorous and fast. You search his face for the punchline and don’t find it.
“Asking… what, exactly?” you say.
His gaze drops briefly, takes you in without shame, without apology. Sweatshirt slipping off one shoulder. Bare throat. Relaxed, unguarded you.
“Asking you out,” he says. “Dinner. A drink. Something that actually counts.”
The words land soft and heavy all at once.
You hadn’t thought he would. Not really. Want, sure. Tease, absolutely. But this—this is different. This is Damon choosing, not circling.
You let the moment stretch, just enough to make him wait.
Then you smile.
“Yeah,” you say. “I’d like that.”
For a split second, his mask cracks. Just enough to see the satisfaction underneath.
“Good,” he says, standing. “Tomorrow. Eight. And for the record—”
He leans down, close to your ear, voice low.
“I’ve wanted to do that for a very long time.”
He straightens and walks away like he hasn’t just flipped your world sideways, leaving you alone on the couch with a racing pulse and a smile you don’t bother hiding.
Bonnie’s room smells like vanilla and incense, something warm and familiar that settles your nerves the second you step inside. Music plays low from her phone, an old R&B song humming through the air, steady and unhurried.
You’re sitting on the edge of her bed, one shoe on, the other forgotten on the floor.
Bonnie watches you through the mirror while she twists her hair up, eyes sharp in that way of hers. Not judging. Reading.
“So,” she says, drawing the word out. “Damon.”
You sigh, leaning back on your hands. “I knew this was coming.”
“Oh, absolutely,” she replies, smiling. “I just didn’t think he’d finally grow the nerve.”
You laugh quietly, but your fingers fidget with the hem of your top. You didn’t think he would either. That’s the part you haven’t said out loud yet. The part that still feels unreal.
Bonnie turns toward you fully now, arms crossed. “How long has he been flirting with you?”
You don’t even hesitate. “Longer than he’ll ever admit.”
“Mmhmm.” She steps closer, tilting your chin up gently, inspecting your face. “And how long have you been letting him?”
That earns her a look. “Bonnie.”
She grins. “I’m just saying. You don’t blush like that for someone you’re indifferent to.”
You catch your reflection in the mirror. Bare skin, lips slightly parted, eyes brighter than usual. You look like someone on the edge of something. That realization sends a small shiver through you.
Bonnie reaches for your makeup bag. “Sit still. If Damon Salvatore finally asked you out, I’m not letting you show up looking like you tripped into it.”
“I was in jeans and sweatshirt when he asked,” you remind her.
Her smile softens. “Exactly. And he still asked.”
That lands deeper than it should.
She keeps things simple. A little highlight. Mascara. Lip gloss that smells faintly like cherries. Nothing heavy. Nothing forced. Just you, sharpened a touch.
“You nervous?” she asks quietly.
You nod. “A little.”
“That’s a good sign,” she says. “Means it matters.”
She steps back when she’s done, hands on your shoulders, meeting your eyes in the mirror. “Listen to me. Damon’s reckless with a lot of things. Feelings aren’t one of them. If he crossed that line with you, it’s because he meant it.”
You swallow, heart thudding.
“Plus,” she adds lightly, grabbing your jacket and tossing it to you, “he’s been insufferable all day. That alone tells me everything.”
You laugh, tension easing as you stand. You slip on your jacket, smoothing it down, taking one last look at yourself.
Bonnie gives you a quick hug. Tight. Grounding.
“Go,” she says. “Have fun. And if he breaks your heart—”
“He won’t,” you say, surprising even yourself.
Bonnie smiles like she knew you’d say that. “Text me when he picks you up.”
You hear his car before you see it.
That low purr of the engine rolls up the driveway like a warning. Bonnie’s already grinning, arms folded as she watches you take a breath you didn’t realize you were holding.
“Told you,” she murmurs.
The knock comes a second later. Unhurried. Confident.
You open the door.
Damon stops dead.
It’s subtle, the way it hits him. His gaze sweeps you once, slow and unapologetic, starting at your heels and taking its time on the way up. The dress hugs you just enough to make a point. Your jacket’s open. Skin visible. You didn’t overdo it—and somehow that makes it worse.
His jaw tightens. He bites his lower lip without thinking.
“Well,” he says quietly. “That feels unfair.”
You smile, leaning casually against the doorframe. “You clean up all right yourself.”
He does. Black jacket, dark shirt open at the throat, that familiar lazy confidence sharpened into something deliberate. Tonight, he looks like he knows exactly what he wants.
His eyes flick to your mouth. Back to your eyes.
“I’m trying very hard to remember we’re going out,” he says. “And not just… staying right here.”
Bonnie clears her throat loudly from behind you. “I’m still in the room.”
Damon doesn’t look away from you. “Tragic.”
You laugh, warmth blooming low in your stomach, and step outside. Damon offers his arm—not because you need it, but because he wants the excuse. His fingers brush your wrist as you take it, lingering just a second too long.
“Seatbelt,” he murmurs once you’re in the car, leaning across you.
His hand pauses near your waist, knuckles grazing your side. His voice drops.
“Safety first.”
You tilt your head. “Of course.”
He smirks like he knows exactly what that does to him and straightens with visible restraint.
The drive is quiet in the good way. Music low. Damon’s knee brushing yours at every stoplight. His eyes keep drifting to you, like he’s checking that you’re real.
“You nervous?” he asks.
“A little.”
“Good,” he says. “Means you care.”
“So do you.”
He exhales a soft laugh. “Yeah. I do.”
The bar is dim and intimate, all dark wood and amber light. The kind of place that encourages leaning close. Damon chose it on purpose.
He orders without asking—bourbon for him, something smooth and dangerous for you. When the glasses arrive, he slides yours across the table with his fingertips.
“Trust me,” he says.
You take a sip. It’s perfect. Warm. Slow.
Damon watches your mouth while you drink. Doesn’t hide it. Doesn’t apologize.
“That look,” he says. “You do it every time you like something.”
You raise a brow. “You’ve been paying attention.”
“I’ve been paying attention for years.”
The words sit between you, heavy and honest.
He leans in, forearms resting on the table, voice low enough that it feels like it’s meant just for you.
“You know,” he says, “there’s something incredibly distracting about seeing you like this. Knowing I finally get to do something about it.”
“Do what, exactly?”
His smile turns slow. Dangerous.
“That,” he says, eyes flicking to your lips again. “Depends how the night goes.”
Your pulse jumps. You lean closer too, closing the space just enough to feel the heat of him.
“I’m having a very good night so far,” you say.
He lifts his glass in a small toast. “So am I.”
The clink is soft. Intimate.
And when he smiles at you over the rim of his glass, it’s different from his usual smirk. Less playful. More certain.
Like this—whatever this is—has already begun.
The second drink hits differently.
The bar’s louder now, a little more alive, bodies shifting closer together as the night settles in. Damon’s already halfway out of his chair before the bartender finishes pouring.
“Pool?” he asks, thumb hooked around his glass. “I feel like winning something.”
You follow him toward the table, eyeing the cue rack. “And what exactly do you think you’re winning?”
He leans in close, voice brushing your ear. “Depends how generous you’re feeling.”
The game starts playful. You make a decent shot, surprising him, and his grin widens like he enjoys being proven wrong. He circles you when it’s your turn, close enough that his presence presses in from all sides.
“Careful,” he murmurs, positioning your hands on the cue. “You rush it like that, you’ll miss.”
His hands settle over yours. Warm. Steady. His chest brushes your back, deliberate this time. He doesn’t pretend it’s about the shot.
You sink the ball anyway.
Damon exhales a quiet laugh. “Show-off.”
When it’s his turn, you sit on the edge of the table, legs crossed, watching him line up the shot. He glances back at you, eyes dark, and misses on purpose.
“You did that,” you say.
“I absolutely did,” he replies, setting the cue aside and stepping into your space.
Back at the bar, the third drink arrives unspoken. Damon’s knee presses between yours now, casual enough to pass, intimate enough to mean something else entirely. His hand finds your knee beneath the bar, thumb brushing slow, absent-minded circles like he’s testing your reaction.
You don’t pull away.
His gaze drops to where he’s touching you. He bites his lip again, harder this time.
“You’re dangerous,” he says quietly.
“You been saying that all night”
“Yeah,” he replies. “And you keep proving me right.”
The kiss happens without announcement.
One second you’re laughing softly at something he said, the next his hand is at your jaw, thumb tilting your chin up. The kiss is unhurried, deep, like he’s been waiting long enough to savor it. The bar fades. The noise dulls. There’s just his mouth, his grip, the heat spreading through you.
When he pulls back, his forehead rests against yours.
“We should go,” he says, voice rough.
You nod. “Now.”
The door barely closes before he’s kissing you again, the kind of kiss that steals your balance. His hands slide to your waist, firm, grounding, like he’s reminding himself you’re real. You kiss him back harder, fingers curling into his jacket, pulling him closer.
Someone laughs somewhere behind you.
Reality intrudes.
Damon pulls back just enough to swear under his breath, then grips your hand and opens the back door.
“Back,” he mutters again, urgency sharp now.
The space is tight, knees knocking, bodies pressed close by default. The second the door shuts, he’s on you—mouth hot, hands roaming, thumb slipping under the hem of your dress to rest against bare skin.
You gasp softly, and he freezes.
His forehead drops to your shoulder, breath uneven.
“God,” he says. “This is a terrible idea.”
You smile against his cheek. “You’re still here.”
“Barely holding it together,” he replies, lips brushing your jaw. “And we are very much in public.”
A car pulls in a few spaces down. Headlights sweep briefly across the back window.
That decides it.
He pulls away with visible effort, hands still resting on your hips like he needs the contact.
“If we stay back here,” he says quietly, “I’m going to forget where we are.”
You tilt your head, eyes dark. “Drive.”
He swallows.
“Get in the front.”
The engine starts. The car moves.
You don’t put your seatbelt on right away.
Damon notices immediately.
“You’re enjoying this,” he says, eyes flicking between the road and you.
You turn toward him, one knee angled in his direction, fingers trailing lightly along his forearm.
“Enjoying what?”
“The fact that I’m trying very hard to be a gentleman.”
Your fingers drift higher. Not enough to cross a line. Enough to promise one.
He exhales through his nose. “You’re going to be the death of me.”
You lean in, voice low. “You like it.”
His jaw tightens. “I like knowing where this ends.”
“And where’s that?”
He glances at you again, gaze heavy. “Inside. With a locked door.”
That sends a slow heat curling through you.
You settle back in your seat—finally buckling in—smiling like you’ve already won.
The rest of the drive is quiet in the most dangerous way. Stolen looks. Lingering touches at stoplights. The kind of silence that’s full instead of empty.
By the time he pulls up to your house, the tension between you feels unbearable.
Damon cuts the engine, and the silence snaps tight between you. For a second, neither of you moves. The air feels thick, crowded with everything you haven’t said yet. He turns in his seat, slow, deliberate, elbow settling against the console like he’s got all the time in the world—even though his eyes give him away. They drag over you. Linger. “You know,” he says, voice low and amused, “there was a version of this night where I drove away like a gentleman.” You smile, already leaning closer. “And?” “And I didn’t like it.” Your fingers slide into the open edge of his jacket, gripping fabric, grounding yourself in the reality of him. “Good. Because I didn’t go on a date with Damon Salvatore for restraint.” That does it. His breath hitches, just barely, and his hand comes up to your jaw, thumb brushing your lower lip like he’s been wanting to do it all night. When he kisses you, it’s slower than before—deeper. Less frantic. The kind of kiss that says I’m done pretending this is a question. When he pulls back, his forehead rests against yours. “I like you,” he says, simple and sure. You don’t hesitate. “I like you too.” A smile curves his mouth, warm and dangerous all at once. “Then let’s stop dancing around it.” He opens his door, comes around to yours, and offers his hand—not teasing this time, not playful. Certain. Expectant. You take it. Inside the house, the door clicks shut behind you, and the night finally exhales. Damon’s hands settle at your waist, familiar already, like this has always been where it was headed. He looks at you once more, eyes dark with promise. “Just so we’re clear,” he murmurs, lips brushing your ear, “I plan on remembering every second of this.” You smile, fingers tightening in his shirt. “I’d be disappointed if you didn’t.”
Then his lips were on your neck, a trail of fire that made your head fall back against the door with a soft thud. He wasn’t just kissing you; he was mapping you, learning the scent of your skin, the rhythm of your pulse. You could feel the faint, delicious scrape of his fangs as he nipped at the sensitive skin just below your ear, a clear, present threat that made you shiver with anticipation.
“You smell… divine,” he growled, the words vibrating against your throat. “Like night-blooming jasmine and… temptation.”
Your hands slid up his chest, feeling the solid muscle beneath the thin cotton of his shirt. You wanted to feel him, all of him. “Damon,” you breathed, his name a plea on your lips. “Stop teasing.”
He chuckled, a low, dark sound. “Oh, sweetheart, I haven’t even started.” But he obliged you, lifting his head to capture your mouth again. This time, his hands were roaming, tracing the curve of your spine, the dip of your waist, one hand splaying wide over the swell of your ass and pulling you hard against him. You could feel his arousal, thick and insistent, through the layers of your clothes, and it sent a fresh wave of heat pooling low in your belly.
With a surge of your own vampiric strength, you spun him, pushing him back against the door. The surprise in his eyes quickly melted into a look of dark, hungry approval. “Feisty,” he purred. “I knew it.”
“Don’t get comfortable,” you warned, your hands fumbling with the hem of his shirt. You needed it off. Now. You ripped it over his head, the fabric tearing slightly in your haste, and tossed it aside. Your eyes drank in the sight of him. Pale, sculpted chest, the hard planes of his abdomen, the dark trail of hair that disappeared into the waistband of his jeans. He was a masterpiece of lethal beauty.
Your hands roamed over his skin, tracing the lines of muscle, feeling the coolness of it. You leaned in, pressing open-mouthed kisses to his chest, your tongue flicking over a flat nipple. He hissed, his hands tangling in your hair again, guiding you. You bit down gently, and his grip tightened, a groan rumbling in his chest.
“Your turn,” he rasped, and in a blur of motion, you were the one against the door again. He made quick work of your dress, his fingers skillfully finding the zipper and sliding it down. The silk pooled at your feet, leaving you in just a scrap of lace. His eyes, so dark they were almost black, raked over you, and the raw, undisguised lust in them was the most intoxicating thing you’d ever seen.
“Perfect,” he breathed, before sinking to his knees in front of you.
The sight of Damon Salvatore on his knees for you was a power rush like no other. He looked up at you from under his lashes, his hands gripping your hips. He hooked his fingers in the sides of your panties and slowly, torturously, slid them down your legs, his gaze never leaving yours. He pressed a kiss to your hip bone, then the other, his breath warm against your skin.
“You’re shaking,” he murmured, his voice a smoky caress.
“I’m anticipating,” you corrected, your voice barely steady.
He smiled, that slow, dangerous smile, and then he leaned in. The first touch of his tongue against your core was electric. It wasn't a tentative exploration; it was a deliberate, confident stroke. He licked you from your entrance to your clit, a long, slow drag that had your knees buckling. His hands held you up, his grip firm and unyielding as he began to devour you.
He was relentless. He alternated between broad, flat strokes of his tongue and pointed, precise flicks against your swollen clit. He knew exactly how to build the pressure, how to stoke the fire until you were writhing against him, your fingers clutching at his hair. He slid one finger inside you, then another, curling them to find that spot that made you see stars. The dual sensation of his mouth and his fingers was overwhelming, a pleasure so intense it was almost pain.
“Damon, please,” you gasped, your hips rocking against his face, chasing the release that was just out of reach.
He hummed against you, the vibration sending you hurtling closer to the edge. “Come for me,” he commanded, his voice muffled by your flesh. “Let me taste you.”
That was all it took. The coil of pleasure in your belly snapped, and your orgasm crashed over you in a blinding wave. You cried out his name, your body convulsing as he worked you through it, his tongue lapping up every drop of your release. He didn’t stop until you were limp and panting, your body boneless against the door.
He rose slowly to his feet, his lips glistening with your essence. He kissed you then, and you could taste yourself on his tongue, a primal, intimate flavor that made your head spin. He lifted you effortlessly, your legs wrapping around his waist as he carried you through the dark house to your bedroom. He laid you down on the bed gently, a stark contrast to the raw hunger he’d just displayed.
He stood at the edge of the bed, his gaze sweeping over you. He quickly shed his jeans and boxers, and your breath caught. He was magnificent, long and thick and proudly erect. He crawled onto the bed, covering your body with his, his weight a delicious pressure. He settled between your thighs, the head of his cock nudging against your still-sensitive entrance.
“Last chance to change your mind,” he whispered, though his eyes said he knew you wouldn’t.
“Shut up and fuck me, Damon,” you demanded, your nails digging into his shoulders.
He grinned, and with one powerful thrust, he was buried inside you. You both groaned at the sensation, the perfect, exquisite stretch of him filling you completely. He stilled for a moment, letting you adjust, his forehead resting against yours.
“You feel… incredible,” he breathed. “So tight. So perfect.”
Then he began to move. His pace was slow at first, a deep, rhythmic rocking that stoked the embers of your arousal back into a raging fire. He watched you as he moved, his eyes dark and intense, cataloging every gasp, every shudder, every arch of your back. He was savoring this, savoring you.
“Faster,” you urged, your hips rising to meet his.
He obliged, his movements becoming harder, faster. The sound of skin slapping against skin filled the room, mingling with your moans and his ragged breaths. He angled his hips, hitting that perfect spot inside you with every thrust, and you felt yourself climbing again, hurtling toward another peak.
One of his hands slid between your bodies, his fingers finding your clit and rubbing in tight, insistent circles. The dual stimulation was your undoing. Your second orgasm ripped through you, even more powerful than the first. Your inner walls clenched around him, and he groaned, his rhythm faltering.
“Fuck, yes,” he growled, his thrusts becoming erratic. He buried his face in your neck, his fangs scraping against your skin. The threat was back, more potent than ever. “I want to bite you,” he rasped. “I want to mark you as mine.”
“Do it,” you gasped, your body still trembling from the force of your release. “Bite me.”
With a guttural cry, he sank his fangs into the soft
The sharp, piercing pain was instantaneously eclipsed by a wave of euphoric pleasure so intense it was almost unbearable. He drank from you, his hips pumping into you one last, hard time as he found his own release, his hot seed spilling deep inside you.
He collapsed against you, his body heavy and sated. For a long time, you just lay there, tangled together, the only sound your mingled breathing. He gently lapped at the bite mark on your neck, his tongue soothing the twin wounds until they closed. He rolled to the side, pulling you into his arms, your head resting on his chest.
You could hear the steady, slow beat of his heart under your ear. It was calming, grounding. You traced idle patterns on his skin, feeling a sense of rightness, of coming home, that you’d never felt before.
He pressed a soft kiss to the top of your head. “Well,” he said, his voice a low, contented rumble. “That was not gentlemanly.”
You smiled against his chest. “It was perfect.”
He was quiet for a moment, and you could feel him thinking. “I meant what I said earlier,” he murmured. “I like you. A lot.”
You lifted your head to look at him. His eyes were soft in the dim light, the predatory hardness gone, replaced by something warm and genuine. “I like you too, Damon.”
A slow smile spread across his face. “Good. Then you’re free tomorrow night. I’m taking you out again.”
It wasn’t a question. It was a statement of fact, a promise. And you knew, with a certainty that settled deep in your bones, that this was only the beginning.
Who could resist her charm? This radiant 1950s-style pin-up girl poses in a black dress (AI-generated) and lace stockings in a vibrant retro bar. Neon signs twinkle, drinks flow, and the authentic 1950s lifestyle comes alive around her.
