@jacklessweetheart .. ‧₊˚✧ ℬ𝑒𝑎 ✧˚₊‧ 𝑣𝑖𝑟𝑔𝑜, 𝟸𝟼 ♡ 𝑖 𝑙𝑖𝑘𝑒 𝑚𝑦 𝑚𝑒𝑛 𝑎 𝑙𝑖𝑡𝑡𝑙𝑒 𝑏𝑖𝑡 𝑜𝑙𝑑𝑒𝑟…
𝑗 𝑎𝑐𝑘𝑙𝑒𝑠. 𝑤𝑟𝑖𝑡𝑒𝑟. 𝑟𝑒𝑎𝑑𝑒𝑟. 𝑝𝑡. 𝑒𝑛.
𝑚𝑎𝑠𝑡𝑒𝑟𝑙𝑖𝑠𝑡
ʷᵃʳⁿⁱⁿᵍ ⁺¹⁸
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@jacklessweetheart
@jacklessweetheart .. ‧₊˚✧ ℬ𝑒𝑎 ✧˚₊‧ 𝑣𝑖𝑟𝑔𝑜, 𝟸𝟼 ♡ 𝑖 𝑙𝑖𝑘𝑒 𝑚𝑦 𝑚𝑒𝑛 𝑎 𝑙𝑖𝑡𝑡𝑙𝑒 𝑏𝑖𝑡 𝑜𝑙𝑑𝑒𝑟…
𝑗 𝑎𝑐𝑘𝑙𝑒𝑠. 𝑤𝑟𝑖𝑡𝑒𝑟. 𝑟𝑒𝑎𝑑𝑒𝑟. 𝑝𝑡. 𝑒𝑛.
𝑚𝑎𝑠𝑡𝑒𝑟𝑙𝑖𝑠𝑡
ʷᵃʳⁿⁱⁿᵍ ⁺¹⁸
Jensen Ackles: A Director’s Journey
Jensen Ackles (◠‿◠✿) | NashCon 2025
⋆౨ৎ˚⟡˖ ࣪ i need this man in a very inappropriate way
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Jensen on Jimmy Kimmel - [x]
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When we met again…
Jensen Ackles x reader (no use of y/n)
warnings: 18+ MDNI smut, alcohol consumption, dacryphilia (maybe), petnames, age gap, fem!reader
What happens when you and Jensen break up and meet again after months of not seeing each other.
jacklessweetheart masterlist
note 1: This is kind of a part 2 to When in Rome, and you don't need to read it to understand this one, but...
note 2: I mean no hate towards anyone, this is just a work of fiction. Don’t like it, don’t read it. Be aware that English is not my first language, you can tell me if something doesn’t make sense. Also, please, comment! It means a lot to me to know if you like my work.
The bar was crowded, bass hummed low, lights soft glowing, the sound of clinking glasses also filling the place. I was out with my girls, laughing a little too loud, drinking colorful drinks, trying to pretend the last few months hadn't carved a hole in my chest. It had been almost a year with him. Jensen. A year that still felt like a fever dream.
He and I met at an after party in Rome. He was there in his amazing green suit, matching his eyes, sleeves rolled up, looking unfairly good for a man who could've been my dad's slightly younger brother. He was concerned with it since moment one, but to me it never mattered, not when his hand found the small of my back like it belonged there, not when his voice dropped low in my ear with his not-always-there Texas drawl, and definitely not when he had me pressed against his hotel room wall hours later, filthy, but gentle, whispering exactly what he was going to do to me like it was the most natural secret in the world.
After we spent that night together, after going back to our homes and our lives, we just couldn't stay away from each other. Messages turned into phone calls and facetime, that turned into a fancy dinner at his favorite restaurant in LA that he wanted to show me, and when I least expected he came over to my house with flowers and asked me to be his girlfriend. He’d always been perfect. Patient when I needed space, present when I didn’t. He showed up for my family dinners, charmed my mom, talked football with my dad like they’d known each other for years. He checked in when I was stressed, made me laugh until my ribs hurt, and in bed… God, Jensen was a gentleman everywhere else, but between the sheets he was devastating, subtle at first, almost shy in the way he’d watch me like he couldn’t quite believe his luck. Then that quiet confidence would slide in, his voice roughening as he told me exactly how my body felt around him, how pretty I sounded when I fell apart for him. Dirty in the softest, hottest way possible. And unforgettable.
Until the age thing started mattering to everyone else. The whispers. The looks. The way our friends joked about “daddy issues” one too many times. It chipped away until one rainy afternoon us both admitted it was getting too heavy. The breakup wasn’t dramatic, no screaming, no slammed doors. Just quiet sadness and the kind of hug that felt like goodbye and I’ll-miss-you in the same breath. He left my apartment and the rain immediately started to fall, like it wasn't just me crying. And I hadn't seen him anymore. Not until tonight.
I felt him before I saw him, his presence is always magnetic, making me feel a familiar prickle on the back of my neck. When I turned in his direction, he was leaning against the bar maybe twenty feet away, talking to a couple of guys, and something in the way he holds himself already made me melt. His eyes locked on me almost immediately, like they’d been waiting. He looked good, as usual, dark Henley stretched across his shoulders, jeans, that slight scruff along his jaw, his necklace picking off his shirt. His expression flickered: surprise, then something softer, almost hesitant. Shy, almost. My friends noticed too, one of them nudged me:
– Holy shit, isn't that…?
– Yeah – I murmured, heart hammering, but I didn't move and neither did he at first.
I was taking a sip of my drink when he excused himself from his group and started walking towards me, slow, like he was giving me time to bolt if I wanted. I didn't. When he stopped in front of me, close enough that I caught the scent of his cologne, he gave me that small, crooked smile.
– Hey, darlin’, – he said, voice low, subtle, a gentleman, but his eyes dragged over me for half a second, appreciating, remembering and making heat pool low on my stomach.
– Jen, – my voice came out steadier than I felt. – It's been a while.
– Too long – he confirmed and then glanced at my friends, a polite nod, then back to me. – You look… damn. You look good.
Our conversation started easy, just surface stuff, my work, his work, how my family was doing. He asked about everything like it really mattered to him, like he always did, and I hated how natural it felt. But underneath it, the air between us thickened. I caught his gaze on my mouth when I laughed or smiled, his fingers flexing around his whiskey cup, like he wanted to reach for my waist.
My friends drifted off to dance for a while, like they wanted to give us space, shooting me knowing looks. And suddenly it was just the two of us in the noisy bar, inches keeping us apart. He rubbed the back of his neck, that shy flicker again:
– I think about you a lot, more than I probably should.
My breath caught, I looked at his mouth.
– Yeah?
– Yeah! – His voice dropped, he stepped closer, shielding me from the crowd without getting into my space, classic Jensen.
When he noticed that he still had the same effect on me, that still could make my body melt just by looking at me, his confidence shifted in, like a switch. His eyes darkened as they held mine. He got even closer, his mouth near my ear, no more than a whisper:
– I think about how you used to look at me right before I’d pull you into my lap. How you’d say my name all soft and needy when I had my mouth on you. How fucking perfect you felt squeezing around me while I told you how good you were taking it.
Heat flashed through me. He said it so quietly, so matter-of-fact, like he was commenting on the weather, but the words were pure sin. Gentleman on the surface, filthy underneath. Exactly how I remembered. I swallowed:
– Jen…
– I miss that… I miss everything about you, I know I was the one that broke things up between us, I was afraid that you'd hate me because of what people said, but… – he breathed – I was wrong, and I know that now… I miss the way you’d get shy when I’d talk dirty, then beg me for more. Miss waking up with you tangled around me. – His hand brushed my arm, light, but it sent electricity across my skin. – He continued, voice rougher now, direct. – I miss being inside you… Tell me I’m not the only one who still feels it.
He wasn't. God, of course he wasn't.
– You're not – I whispered.
His smile turned knowing, that subtle heat flaring.
– Good. Because I’ve been standing here trying to be respectful, but all I can think about is taking you home, peeling that dress off you slowly, and reminding you exactly how well we fit. – He leaned in, lips brushing my ear. – I’d start gently, baby. Kiss every inch I’ve been missing. Then I’d get greedy. Have you riding me while I tell you how tight and wet you still get for me.
My thighs pressed together, the bar noise faded to nothing. He pulled back just enough to meet my eyes, searching. A gentleman again, giving me the out if I wanted it, but the heat in his gaze said he hoped I wouldn’t take it. And I didn't.
– Take me home, Jensen, please.
His exhale was shaky with relief and want. He slipped his hand into mine, warm and sure, thumb stroking my knuckles like he used to. He left his cup and mine at the counter, left enough money to cover both of our tabs at least two times, and led me out into the cool night air. I felt the familiar pull, the one saying this might be too complicated in the morning, the reasons we broke up still between us. But that night, while his arm was sliding around my waist and his voice was murmuring low promises against my ear, none of it really mattered. I'd deal with the problems tomorrow.
The cool night air did nothing to settle the heat humming between us. He didn't say much, just opened the passenger door of his car for me like he always did, his fingers lingering a second longer than necessary on my waist as I slid in, and the look he gave me before closing the door made my stomach flip.
He started the engine, the low rumble filling the quiet space. For the first few blocks, he kept both hands on the wheel, driving with that calm focus he always had. I could feel him stealing glances at me, though. Soft at first, almost shy, like he was still processing that I was really there in his car again after months apart. Then his right hand left the wheel. It settled on my thigh, high enough that his fingertips brushed the hem of the dress, warm palm pressing against bare skin. Not demanding, just claiming. Gentle, but possessive in that quiet way that is only his.
– You're so beautiful – he murmured. His eyes flicking from the road to my face. THe streetlights washed over his face as he looked at me like I was the only thing worth seeing in the whole city. – I mean it. Every time I look at you… It hits me all over again. – His thumb started a slow, lazy stroke along the inside of my thigh, inching just under the fabric of the dress. The touch was light, almost reverent, but it sent sparks straight through me. He kept driving, one hand on the wheel, the other mapping my skin like he was memorizing it all over again. I shifted slightly, pressing my thighs together around his hand, and he let out a low breath. – Easy, baby – he said, voice dropping into that rougher tone that I love. A small, knowing smile tugged at his lips. – We’re not even halfway there yet. – But his fingers didn’t stop moving, doing subtle circles, teasing higher, then pulling back just enough to keep me wanting.
He glanced over again, longer this time. His green eyes darkened as they traced my face, lips, the way my chest rose with each quick breath. The city lights blurred past the windows while his hand kept its slow exploration. He squeezed my thigh gently, then let his fingers drift higher, brushing dangerously close to where I was already aching for him.
– I've been thinking about these thighs wrapped around me – he admitted, voice low and direct now, confidence fully slipped into place. – How soft they are. How they shake when I’ve got my tongue on you… or when I’m buried deep and you’re trying so hard to stay quiet for me. – He looked over once more, the same reverent, almost awed expression mixed with pure heat, before turning his attention back to the road. His apartment building came into view a few blocks ahead.
Jensen’s hand stayed right where it was, warm and sure on my thigh, thumb still stroking like he couldn’t bear to stop touching me. When he pulled into the underground parking garage and killed the engine, he didn’t move right away, he just turned to face me fully, eyes dragging over me slow and hungry.
– C’mere – he said softly. He leaned across the console, one hand still gripping me, the other sliding into my hair as he kissed me, deep, slow, like he'd been starving for it. When he finally pulled back, forehead resting against mine, his voice was barely above a whisper. – Let’s get upstairs, baby. I’ve got months of missing you to make up for.
The elevator ride up was torture in the best way. Jensen kept me close, his arm wrapped around my waist like he was afraid I’d vanish if he let go. His thumb traced slow circles over my hip through the thin fabric of my dress, and every floor that dinged by felt like it took forever. The mirrored walls caught us, his tall frame curved around mine making my legs feel weak, my flushed cheeks, his dark eyes locked on my reflection like he was already undressing me in his mind. When the doors opened on his floor, he didn’t rush. He guided me down the hall with that same quiet confidence, keys in his other hand, but he paused right outside his door. Turned me gently so my back was against the wall beside it, caging me in without touching me fully. His forehead dropped to mine again.
– You sure? – He whispered, voice low and rough. – We walk through this door and I’m not gonna be able to keep my hands off you, darlin’... Not tonight.
I answered by sliding my hands up his chest, feeling the steady thunder of his heart under the soft Henley, and pulling him down into a kiss. It started slow like the one in the car, but hunger won fast. His tongue slid against mine, deep and claiming, one big hand cupping the back of my neck while the other gripped my waist hard enough to bruise in the sweetest way. He fumbled the key into the lock without breaking the kiss.
The inside of his apartment smelled like everything his, his laundry, his cologne, his aftershave, and that special smell that is only his. He kicked the door shut, backed me up against it, and kissed me like a man starved.
– Jen… _ I breathed, surprised by his actions.
– I've been dreaming about your mouth on mine for months.
His hands slid up my thighs, pushing the dress higher, slow and reverent. He pressed open-mouthed kisses along my face, my neck, pushing my hair aside for better access. His green eyes were almost black with want.
He knelt in front of me, and started to kiss my legs, calves, the inside of one knee, then higher, raising my dress with it, until his breath ghosted over my lace panties. He looked up at me and said:
– You're so fucking pretty, baby. – He got up, took my dress off completely, and kissed my mouth again. Then hooked his fingers into the waistband of my panties and dragged the lace down my legs. He helped me step out of them, then tucked them into his back pocket with a wicked little grin. – Mine now.
I laughed a little, skeptic. But before I could respond, his mouth was on my body again. Hot, slow, devastating, in every corner that he could reach. Jensen groaned against me. He scooped me up like I weighed nothing, my legs wrapping around his waist as he carried me through the familiar apartment toward his bedroom. He laid me down on his bed like I was something precious, then stood back for a second just to look at me, totally naked to his mercy, chest heaving, lips swollen. He peeled his Henley off slowly, revealing the broad shoulders and defined chest I’d missed so badly. His necklace glinted against his skin. Jeans next, pushed down with his boxers until he was gloriously naked, cock heavy and flushed, already leaking at the tip. He crawled over me, settling between my thighs, forearms braced on either side of my head.
– Look at me, sweetheart – he said softly. And I did. Those green eyes were everything: soft, hungry, full of that quiet love that always undid me. – I missed you – he whispered.
– I missed you so much, Jen – I murmured, my eyes never leaving his face. – I don't want to stay away from you anymore.
– Me neither, love. I'm so sorry I left. – He breathed against my face, and left open-mouthed kisses all over my face. He lined himself up and pushed in slowly, inch by thick inch, stretching me open in that perfect burn I’d craved for months. – Fuck… This pussy is always so tight for me. – When he bottomed out, we both groaned. He stayed there, buried deep, forehead pressed to mine, breathing hard.
His hips rolled in tiny, maddening circles, slow. I wrapped my arms around his neck, nails digging into his back, I whispered against his ear:
– Fuck me, please – I begged.
– Yes, ma’am – I little playful smile on his lips and he started moving. His hips were slow at first, deep rolls of his hips that dragged every thick inch of him along every sensitive spot inside me, no rush like he wanted to savor every second, every flutter of my walls around him. – You’re pulling me in so deep. – He breathed against my lips, voice low and wrecked.
One of his hands stayed buried in my hair, fingers threaded through the strands, cradling the back of my head like I was fragile. The other hand never stopped moving, sliding down my side, gripping my hip to hold me open for him, then smoothing up my ribs, thumb brushing the underside of my breast. He kissed me like he was trying to pour every missed month into my mouth, wet, hungry, and then he pulled back just enough to trail those same kisses across my cheek, my jaw, the corner of my eye. When a soft whimper slipped out of me, he caught it with his lips again.
– Look at me, darlin’ – he whispered, forehead pressed to mine, green eyes dark and burning. Another slow, grinding thrust that made me arch my back off the bed.
The pleasure was already overwhelming, every drag of his cock, every circle of his thumb over my nipple, every time he tugged gently at my hair to tilt my head exactly how he wanted. I felt completely surrounded by him, consumed. Tears pricked at the corners of my eyes.
– Jen… – My voice cracked. His hand slid back into my hair, cradling my head as he kissed the tear that slipped free, tasting it.
– Too good, huh? – A mischievous smile on his face.
He kept the pace devastatingly slow but deep. His body covered mine completely, hips rolling in a perfect rhythm, chest pressed to my breasts, skin hot and slick. His free hand mapped every inch of me he could reach, down my thighs, hitching it higher around his waist, then back up to cup my face, thumb stroking my cheek while he kissed me again, tongue sliding against mine in time with his thrusts.
– You feel so perfect, – he murmured right against my mouth, voice rough – so wet, so tight. Missed this pussy squeezing me like it never wants me to leave. – He kissed my wet eyelashes, then the bridge of my nose, then my parted lips again.
Another tear slipped down my temple, and he chased it with his tongue, then sealed his mouth over mine in a deep, filthy kiss as he ground against my clit with every thrust. The pressure inside me coiled tighter, hotter, almost unbearable. My hands clutched at his back, nails digging in as my thighs started to shake around him.
– That’s my good girl – he praised, voice dropping even lower. His hand tightened gently in my hair, the other sliding down to grip my ass, pulling me into every stroke. – I want to feel you come all over me while I’m deep inside you. – He angled his hips just right and hit that spot inside me again and again. The combination of his cock, his constant touch, his mouth on my face, his voice in my ear was too much. My orgasm crashed over me hard, long, devastating. A broken sob tore from my throat as my walls clamped down around him, pulsing, flooding with heat. Tears streamed freely now, and Jensen kissed every single one away, murmuring soft, filthy praise against my skin. – Fuck, baby, you’re squeezing me so tight.
He fucked me through it, slow and steady, drawing it out until I was trembling and whimpering beneath him. Even when the last aftershocks faded his hips were still rolling gently, keeping me full of him. He brushed damp hair off my forehead.
He stayed buried deep inside me for a long moment after my first orgasm, kissing the tears from my cheeks, his cock still twitching with the effort of holding himself back.
– I want you to turn over for me, baby, – he murmured, voice husky. I nodded and he helped me turn, as I was boneless, but still eager. The large mirror leaning against the wall directly in front of his bed caught us perfectly. – Face down, ass up – he commanded and I did as I was told.
Jensen positioned me right at the edge of the mattress so I had a clear view: my flushed face, swollen lips, eyes still glassy with tears and lust. And behind me, him. He looked devastating: strong, broad shoulders flexed as he knelt behind me, chest glistening with a light sheen of sweat. His hair had fallen messily over his forehead, those green eyes dark and locked on my body in the reflection. The necklace dangled as he leaned forward. Every muscle in his body stood out as he gripped my waist with both big hands.
He spread his knees wider, pulling my hips back toward him. One hand stayed firm on my waist while the other slid down to my ass, squeezing, then gently opening me for him. I felt the thick head of his cock nudge against my soaked entrance, teasing once, twice, before he pushed in, stretching me open again in one long stroke until his hips were flush against my ass.
A broken cry left my lips.
– Fuck… Look at that – he groaned, watching in the mirror as he sank all the way in. His head fell back for a second, eyes fluttering shut in pleasure, before he forced them open again. His jaw tight, lips parted, raw pleasure written across every feature, made heat flood through me even harder.
He started thrusting, deep and powerful, one hand anchored on my waist, the other sliding up and down my back, then gripping my hip again so he could open me wider for every stroke. The sound of skin meeting skin filled the room, wet and filthy, mixed with his low, guttural groans.
I moaned, repeating his name like a prayer, unable to stop. Every thrust pushed a new cry from my throat asking for more. His hair fell further into his eyes as he leaned over me, one hand leaving my hip just long enough to brush it back before both hands returned in a possessive way, grounding, never leaving my body. Hips snapping harder now, the angle letting him hit that perfect spot with every stroke. It seemed like he just couldn't stop telling me how good my pussy felt around him, voice rough with pleasure. In the mirror I could see everything: the way his abs flexed with every thrust, the intense focus on his face, the way his mouth fell open on a moan when I clenched around him. All I could do was push back against him, desperate, chanting his name between sobs and moans. He growled, one hand sliding around to rub tight circles over my clit while the other kept a bruising grip on my hip, holding me open as he drove into me harder. His eyes never left mine in the mirror.
– I want you to come for me again, sweetheart.
The combination of his thick cock pounding deep, his fingers on my clit, the raw sight of him behind me looking wrecked with pleasure, his constant touch, sent me spiraling. My second orgasm ripped through me even harder than the first. I cried out his name, walls pulsing violently around him as my arms gave out and my face dropped to the sheets.
– Jensen… Fuck!
He kept thrusting through it, slower now but still deep, groaning my name like a curse and a blessing while his hands stroked soothingly over my back and hips, never once letting me go. His hair was messy over his eyes, chest heaving, that gorgeous face twisted in pleasure as he watched me fall apart for him in the mirror. He leaned down to press open-mouthed kisses along my spine.
When I finally caught my breath, I looked at him in the mirror. My voice came out hoarse, needy, and shameless:
– Jen, baby, please. I want you to come in my mouth. – I swallowed, cheeks burning.
His eyes darkened instantly. A slow, filthy smile spread across his face, part surprise, part pure sin. That gentleman mask slipped completely for a second.
He pulled out carefully, leaving me empty and aching, then helped me turn over onto my back with gentle but eager hands. I settled against the pillows, looking up at him as he moved over me. He straddled my chest first, then shifted higher until his thick thighs bracketed my face, knees planted on either side. The view was overwhelming, his powerful body towering above me, abs tight, cock heavy and slick from me, hovering just over my mouth. His hair fell messily into his eyes as he looked down, one hand braced on the headboard, the other already wrapping around his shaft.
– Open that pretty mouth for me, darlin’ – he murmured. I did, tongue out, eyes locked on his. He stroked himself slowly at first, base to tip, his fist slick with my wetness. The muscles in his arm and chest flexed with every movement. He looked wrecked, jaw slack, lips parted, that dirty smile still playing at the edges as he watched me wait for him like this. – Such a good little slut for me – he praised, voice dripping with heat. His free hand reached down to cup my cheek, thumb stroking my bottom lip. – Look at you, huh, so fucking eager.
His strokes grew faster. Low groans slipped from his throat as his hips twitched. I could see the way his brows pulled together, the way his mouth fell open further, the flush creeping up his neck. His thighs trembled slightly against the sides of my head.
I moaned softly, tongue ready, hands sliding up his thighs to hold onto him. That seemed to push him over the edge. His rhythm faltered, a deep guttural groan tearing from his chest as the first thick rope of cum landed across my tongue. Then another, and another. Hot and salty, coating my lips and tongue as he kept stroking through it, milking himself empty with shaky breaths.
He looked so beautiful like that, head tipped back slightly, hair in his eyes, chest heaving, lost in pleasure because of me.
When he finally finished, he stayed there for a second, breathing hard, then slid back down my body. He immediately leaned in and kissed me deep, tasting himself on my tongue without hesitation, groaning into my mouth. His hands cradled my face, thumbs wiping the corners of my lips where some had spilled.
– Goddamn, you’re perfect – he whispered against my lips, voice soft again, full of love. He kissed me slower, sweeter, then pressed open-mouthed kisses across my flushed cheeks and damp eyelashes. – Come here. – He pulled me into his arms, rolling us so I was tucked against his chest, his big hands never leaving my skin, holding me like he never wanted to let go again. – Don't go, please. Never again.
note 3: I hope you liked it! Please, comment and reblog :)
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