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fatecantstopme · 11 months ago

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Unattached Drifter Christmas

Pairing: Dean Winchester x plus size!reader

Summary: Dean decides he’d rather spend Valentine’s Day curled up on the couch with you.

Warnings: Cursing, use of pet names. SMUT, unprotected sex (P in V), oral (M & F receiving)

A/N: in honor of Valentine’s Day, I gift you an adorable Dean Winchester fluffy smutty delight. 💜

"What are your plans, Sammy?" you asked from your perch on the kitchen counter.

"I happen to have a date," he replied with a smirk.

"Oooo with whom?"

"Just a nice local girl I met at the library last week."

"Sam Winchester and the nice local girl...sounds like a book I'd read," you teased.

He rolled his eyes and threw a dish towel at you. "What about you?"

"I have an excellent night planned," you confirmed. "Since Dean will be out cruising for ladies to go home with, I figured I could steal the Dean Cave for the night. I'm ordering a pizza, watching scary movies, eating a shit ton of junk food, and washing it all down with a bottle of wine."

Sam laughed. "Now that sounds like a party."

"Someone say 'party'?" Dean asked as he entered the kitchen.

"We were just discussing our Valentine's Day plans," Sam responded.

"You celebrating Unattached Drifter Christmas?" you asked in a teasing tone.

Dean shrugged and grabbed a beer out of the fridge. "Nahh, I think I'm gonna sit this year out. I'd rather stay home."

"Awww man," you grumbled.

Dean looked at you with an arched brow. "Is that a problem?"

"No," you answered quickly. "It just puts a bit of a wrench in my plans."

"And what are your plans?" he asked.

"I was gonna take over the Dean Cave for the night--scary movie marathon, pizza, snacks, alcohol."

"Pizza, snacks, and alcohol is my holy trinity," Dean said with a wide smirk. "Would you be opposed to me crashing your party?"

"You hate scary movies," you said.

"Yeah, but you love them," he countered. "I'm the crasher, so I'm not gonna demand a change in movie genre."

You smiled at him. "Alright, then you can come. I'll even supply beer."

Dean winked at you. "The way to my heart," he teased.

You rolled your eyes and hopped off the counter. "Oh, did Sam mention he has a date tonight?"

Sam shot you a look and you hurried out of the kitchen, laughing quietly as Dean started to tease his brother.

"A date, baby bro? Look at you!"

**********

You'd sent Dean to pick up the pizza while you set up the Dean Cave for the evening's festivities. You'd made a run to the grocery store earlier in the day to pick up yours and Dean's favorite snacks, as well as a decent supply of wine and beer.

You were more than satisfied with your selections, but for some reason you felt anxious. Well...to be honest, you knew the reason. You hadn't expected Dean to be staying home and you certainly didn't count on him joining you for the evening.

You'd known Dean for a little over five years and in that time you'd grown to care about him deeply, more than you should. He was a genuinely good person underneath his gruff exterior, a facade he had dropped with you long ago.

If you were completely honest with yourself, you knew you loved him, but you would never say anything to him. You knew him too well. Dean had lost virtually everyone he'd ever loved and he blamed himself for their deaths. He avoided romantic relationships like the plague because he didn't want to add another name to the body count. It was hard enough for him to bring you into his life as a friend, and there was no way he would risk anything more than that.

So of course, you kept your mouth shut, hiding your feelings from both Winchesters. The only person that knew how you felt was Jody and she would take that secret to the grave if you wanted her to. You would rather have Dean as a friend than lose him completely.

You tossed your favorite oversized blanket onto the couch with a sigh. You were trying not to think about curling up next to Dean for a movie marathon on freaking Valentine's Day of all days. You knew it was the romantic nature of the day itself that had your stomach in knots. You'd watched movies and binge ate with Dean countless times before without issue, but there was an added intensity to this instance simply because it happened to be February 14th.

You also couldn't help but wonder why Dean wasn't planning on going out. You couldn't remember the last time he neglected to celebrate 'Unattached Drifter Christmas' as he'd always called it. In fact, Dean hadn't been out to pick up a girl in weeks...you were struggling to recall the last time Dean didn't decline a girl's invitation to come home with her.

"I've brought sustenance!" The man in question spoke from behind you, startling you out of your thoughts.

"Jesus!" you yelped.

Dean chuckled lightly. "Sorry, sweetheart. Didn't mean to scare you."

You shot him a look that clearly said 'I wasn't scared', which only caused him to laugh harder.

You tossed a piece of popcorn at him and headed towards the door. "I'm gonna change into comfy clothes before we get started."

"Good idea," he agreed, placing the pizza down on the table before following you out the door.

Five minutes later, you came back into the Dean Cave wearing your most comfortable leggings and an oversized worn out band tee you'd had for at least a decade. You'd opted to forgo a bra for comfort's sake and you hoped Dean wouldn't notice.

Dean was already sitting on the couch, wearing his gray sweatpants and a plain black tee. It was almost offensive how hot he looked in that outfit--no man had any right to look that good in sweatpants.

When you walked in, Dean's gaze traveled from the TV to you. You noticed his pupils dilate slightly as he looked at you, but you figured that was due to the change in light.

You plopped down on the couch beside him, leaving plenty of space between the two of you to avoid any awkwardness. "Ready to be terrified?" you teased.

Dean groaned softly. "You know I'm only watching these because you love them."

You grinned and snagged the remote from him. "They're so good!"

"Our life is a scary movie," he grumbled. "I don't know why you like these."

"I think that's actually why I like them. Our real lives are full of the kind of shit that would make people lose their minds, but for us, it's just another Tuesday. These movies are either cheesy as hell or have an exaggerated version of a monster we have hunted and killed--so it becomes entertaining instead of scary."

Dean raised an eyebrow and shook his head. "Or you're crazy."

You smiled at him and shot him a wink. "That's just an added bonus."

He rolled his eyes and grabbed a slice of pizza. As he shoveled food into his mouth, you opened up a streaming service and typed in the name of the first movie you wanted to watch.

"You remember The Conjuring right? And Annabelle?"

"Yeah," he answered. "That Annabelle one was creepy as hell."

You grinned. "Well this one is in the same universe and I've been dying to watch it."

You pressed play on the remote and the opening credits of The Nun began to play. You snuggled up under the blanket and sighed contentedly, a piece of pizza in one hand and a glass of wine in the other.

Dean glanced at you and couldn't help the soft smile that graced his lips. It was rare he got to see you truly happy and content, so this was a moment he intended to fully savor. He studied your face, desperate to commit it to memory, unwilling to forget how beautiful you looked in this moment.

He sighed softly and closed his eyes, still picturing your face clearly in his mind. It brought another smile to his lips and he breathed in deeply, smelling a mixture of your shampoo and your perfume. He wanted you to be closer to him, but he didn't want to make you uncomfortable.

He made a split second decision and voiced his request aloud, "It's a little chilly in here. Do you mind sharing the blanket with me?" He wasn't cold at all, but he thought it might get you to move closer to him to share.

"Oh! Sure." You smiled and scooted in his direction, holding the edge of the blanket out to him.

He took it and started to cover himself. "You're gonna need to come a little closer, sweetheart," he said with a chuckle. "I need a bit more coverage."

You laughed and moved even closer to him so your arms were now touching. "Better?" you teased.

"Much," he affirmed.

You tried to keep your body relaxed and focused on the movie, but Dean's proximity was overwhelming your senses. You could smell his aftershave, feel his body heat, and see the rise and fall of his chest much more clearly than before. The simple act of a man breathing should not be a turn on...yet here you were.

You shifted slightly as you felt a familiar wave of heat pool in your belly. Not now, you thought to yourself.

"You okay, doll?" Dean asked softly.

His voice sounded lower than before, huskier even, and you had to bite your lip to keep from audibly moaning. As it was, you could feel the slick gathering between your legs, which was mortifying enough.

"I'm fine," you lied, shifting again.

Dean wrapped his arm around your shoulders and tugged you into his side. "Come 'ere," he muttered. "Get comfortable."

You gasped softly at the sudden movement, but you allowed him to pull you closer. You laid your head against his chest and sighed quietly. You had to admit, it was a much more comfortable position to be in, even if it increased your longing.

"Better?" he whispered, echoing your earlier question.

"Yeah," you mumbled.

Dean smiled down at you even though you couldn't see it. He liked this new position--he liked holding you. He knew he was crossing boundaries he'd never intended to cross, but his feelings had become unbearable as of late.

He couldn't remember a moment when he didn't want you and it was getting harder to remember a time when he didn't love you. The last couple months had been hell on his heart and he was starting to break. He hid it from everyone, especially you, but he knew he couldn't do that for much longer.

His random hookups had stopped alleviating his desire to be with you, instead increasing that need tenfold after every encounter. So he stopped hooking up with women altogether. He'd considered moving out of the bunker for a while to get away, but he couldn't do that to Sam or to you.

He found himself in a predicament he'd been trying to avoid for years and the walls he'd built around his heart had started to crumble. There was nothing he wouldn't do to keep you safe--he'd rip out his own still-beating heart if he had to--but he couldn't find the strength to stop loving you. No matter what he did, his love only grew.

It wasn't fair to you and he knew he shouldn't love you, shouldn't tell you, shouldn't pull you into something with him that would almost certainly get you killed, but his own pain was becoming too much. The physical ache in his chest when you were apart was beginning to impact every part of his life, including hunting. He'd be lying if he said it didn't terrify him, but he couldn't fight his feelings any longer.

"(Y/N)?" Dean asked softly.

"Hmm?" you hummed, eyes still trained on the TV.

"Can you look at me, sweetheart?" he murmured.

You shifted your head to look up at him. You were struck by how brilliantly green his irises looked in the dimly lit room, your lips parting slightly in surprise.

Dean's heart was hammering in his chest so quickly he was certain you could hear it. When your pretty (y/e/c) eyes met his, he was immediately lost in them--adrift in an ocean of (y/e/c).

He knew this was it--it was now or never...he could either take the leap or let his pain drown him in loneliness. He chose the former. He lowered his head the short distance to place a soft, warm kiss against your lips.

The moment you felt his lips on yours, it was like the world stopped spinning. Suddenly there was nothing but you and Dean--nothing else existed, nothing else mattered. Just you and Dean.

When your lips began to move against his, returning his kiss, he groaned happily. His hands grabbed at your torso, seeking comfort in your soft flesh. He tugged you towards him, and you shifted your body to straddle his lap, lips never leaving his.

In your new position, you could feel his hardening member pressing against your clothed core. You ground against him, earning a moan from deep in his throat. His hands tightened their grip on your hips and your nails dug into his shoulders as the sensation sent a bolt of electricity through you.

Dean's hands snaked under your shirt and he began tugging it upwards in an attempt to remove it. The logical part of your brain suddenly kicked back on and you grabbed his hand to stop him.

"Dean--wait," you gasped, pulling away from him slightly.

His eyes widened and his body tensed. He quickly removed his hands from your body and held them up in surrender. "I'm sorry, we can stop. I--"

You shook your head. "I just need...I need to say something." You bit your lip. "I don't wanna be a one night stand or a friends with benefits thing. I-I can't, Dean. I can't."

The pain in your voice nearly broke his heart. He wanted to reassure you, but he wasn't sure you would believe him. He had a reputation and it was Valentine's Day...what were the odds you'd believe him?

"(Y/N), listen to me," he said gently, taking your hands in his. "I would never ever make you to do something you didn't want to do...and I would never purposefully hurt you. I need you to know that. Do you know that, (Y/N/N)?"

"Yes," you whispered, nodding slowly.

"Good...because I mean it. I can't do any more one night stands or casual hookups or friends with benefits situations. I can't handle any of those things anymore than I can pretend I don't need you. And I do need you, (Y/N/N). I need you in every way a person can possibly need another...mentally, emotionally, physically--all of it. You're the best part of my fucked up life and I don't want to lose you."

It was rare to see Dean so open and vulnerable. This was one of the very few times you'd been witness to it, but this was, by far, the most emotional moment you'd ever shared with him. You wanted to respond, to say all the things you'd carried in your heart for years, but you couldn't think of a single word to say.

Your silence dragged on long enough that Dean began to worry he'd crossed a line he shouldn't have...a line he couldn't uncross. "Please, (Y/N)," he begged. "Say something."

"I'm sorry," you said quickly, realizing you'd been silent too long. Dean's face fell and you knew he believed you were about to reject him. You placed your hands against his chest in a calming manner, desperate to infuse your love in the touch.

"You're not going to lose me, Dean," you assured him. "I'm not going anywhere...my place is here, with you. This is where I belong--where I want to be. Wherever you are is home to me."

He didn't need grand gestures or romantic poetry. He didn't need some eloquent speech about how much you loved him. All he needed was to hear your sweet voice saying he was your 'home' and he was a goner.

When his lips met yours for the second time, everything felt different. It was as if all the moments of his life before this were in black and white and he was seeing in color for the first time. He felt alive in a way he'd forgotten--whole, in a way he'd never experienced.

He'd had very few positive relationships in his past and most of them ended bloody. He'd thought he'd been in love before, but those feelings paled in comparison to the way he felt about you. This was love, a love so real--so lasting--it was branded into his very soul.

His fingers gripped the edge of your shirt again and this time, you allowed him to remove it. "Fuck," he groaned, hungry eyes trained on your naked chest. "No bra?"

"I wanted to be comfortable."

His large, calloused hands gripped your heavy breasts and he gently kneaded the supple flesh. "I want my girl to be comfortable all the time," he murmured. "So I think we should burn all your bras."

Your soft chuckle morphed into a moan as his lips found one of your nipples. You rolled your hips against him, a soft gasp escaping your lips.

Dean wanted to take his time with you and he was thoroughly enjoying his current activities, but it seemed you had other plans in mind.

"Dean," you whined. "Need you."

He gave your nipple one last gentle lick before lifting his head. "I'm right here, baby."

You rolled your hips against his throbbing cock and he groaned. Clearly you wanted more and he was in no position to deny you anything.

He gripped you tightly and stood up. You yelped in surprise and wrapped your legs around his waist. He turned around so your back was to the couch and he slowly lowered you down, placing you on the couch in front of him. He kneeled down and looked up at you, eyes dark with desire.

His hands slid slowly up your thighs, coming to a stop at the hem of your pants. "Can I take these off?"

You nodded rapidly.

He smirked and began to peel your leggings down at a painfully slow pace. You whined in annoyance, but Dean simply smiled. "Patience, sweetheart."

Finally, your pants, and subsequently your underwear, were tossed onto the floor, leaving you completely bare before him. There was a small part of you that felt self-conscious being naked in front of Dean. It was always uncomfortable for you the first time you found yourself in this position with a new man, but Dean was different. You weren't sure if it was the hunger in his gaze, the affection he clearly had for you, or the love you felt for him...you felt safe, you felt comfortable, and you felt loved. That was all that mattered.

Dean licked his lips in anticipation as he slowly spread your legs, revealing your soaking wet pussy to him. He groaned softly, spreading your legs wider to get an even better view.

"Now that's the prettiest pussy I've ever seen," he murmured. He slid a finger between your folds to collect some of your juices before bringing the finger to his mouth. He sucked it clean with a moan of enjoyment. "Delicious."

Before you had time to react, Dean had grabbed your hips and dragged you forward so you were closer to the edge of the couch. His mouth was on you in an instant, feasting on you like he might never eat again.

Your head fell back against the cushion and soft moans began to stream from your lips. Your legs rested on his shoulders and your hand gripped his hair tightly. Salacious sounds filled the room and you were glad Sam was gone for the night. You had a feeling it was only going to get louder.

Dean's experience in the bedroom was very evident as he ate you out. He was extremely skilled, but more importantly he paid attention to you. He was desperate to learn exactly what drove you wild and he wouldn't stop until he'd mapped out all of your pleasure points.

"Dean," you gasped softly, grip on his hair tightening.

He knew you were close, the way your legs began to tremble and your grip on his hair indicating your impending orgasm like a flashing neon sign.

His fingers dug into your hips, holding you in place so you couldn't squirm away. With expert precision, Dean spelled his own full name against your clit with his tongue, sending you into a spiral of moaning, shaking bliss.

Dean continued to lap up your juices as you came down, and to your surprise, he didn't stop, even as you began to tug on his hair in earnest. "Please, Dean! Too much," you pleaded.

Dean sucked your little bundle of nerves into his mouth and slipped two fingers inside of you. He quickly found your sweet spot and began to drag his fingers along it repeatedly. The shock waves of pleasure had you changing your pleas to moans in seconds.

Your pussy gripped his fingers like iron and he couldn't wait to feel you grip his cock in the same fashion. He hadn't even been inside you yet and he already knew he would never want another woman's body the way he wanted yours.

"Dean!" you cried out, thick thighs squeezing his head, hips gyrating against his mouth as you came once again.

He lapped up everything you had to give him hungrily--wishing he could stay between your legs forever. This time, however, he allowed you to pull him up by his hair.

You were completely breathless, chest rising and falling rapidly. Dean licked his lips and wondered how sexy you'd look riding him, breasts bouncing as he slammed up into you.

"I think," you mumbled, "you have...too much...clothing on."

He laughed at your breathless remark. He had to agree with your sentiment, so he stood up and removed his shirt quickly. When he stood, you were rewarded with a nice view of his erection pressing against the confines of his sweats.

He smiled at you and slowly lowered his pants, revealing his very large member. The tip was red and throbbing, precum leaking from the slit. You licked your lips and eyed him hungrily, wanting to wrap your lips around it with a desperation that surprised you.

"Sit," you begged.

Dean smirked and obliged, sitting down beside you. You slid off the couch and crawled the short distance to settle between his legs.

Your soft hands wrapped around his cock and he groaned softly. "You're so big," you whispered.

"Your hands are small," he teased.

"But my mouth isn't."

Dean didn't have the time to process your sassy comment before your mouth wrapped around him and you began to suck his cock in earnest.

"Holy fuck-" he groaned, head falling back against the cushion.

He tangled his hand in your hair and gently guided your head as you began to take his cock deeper into your throat. You flexed the back of your tongue as you did so and he groaned loudly.

Having gotten the reaction you'd desired, you did the same move a couple more times, allowing his cock to almost leave your mouth before sucking him deep into your throat.

His grip on your hair tightened and his hips thrust forward, causing you to gag slightly. Instead of trying to lift off him, you breathed deeply through your nose and held steady, relaxing your throat as best as you could.

"Baby, you're doing so good for me," Dean murmured. "Making me feel amazing."

You moaned around his cock and reached between his legs to cup his balls and give them a gentle squeeze. His hips bucked slightly at the action, causing you to smirk.

You continued to suck his cock until he tugged your hair a little more harshly. "You gotta stop, doll, or I'm gonna cum."

You hummed in disappointment, but allowed him to pull you off his cock with a soft popping sound. He looked down at you with lust filled eyes and beckoned you towards him.

"Come up here, baby. I wanna touch you," he begged.

You climbed onto the couch with him, straddling his legs once again. You lowered yourself slowly, rubbing his cock against your wet core. You leaned forward to kiss him and repeated the action. He moaned against your lips before pressing his tongue against them, demanding entry.

You parted your lips and kissed him deeply, allowing his tongue to assert dominance. The kiss was passionate and loving, but the fire that burned inside of both of you in that moment only cared about pleasure.

"I need to be inside you," Dean whispered against your lips.

"Please," you begged him, rutting against him once more.

He gripped his cock tightly and lined himself up with your entrance. Once the tip pressed against your tight opening, he released his grip, hands settling on your hips to help guide you down.

You moaned softly as you continued to lower yourself onto his cock--the stretch both painful and enjoyable all at once. He was larger than you were accustomed to, both in girth and in length, and it almost felt as if you were a virgin all over again.

You had to lean forward, pressing your body against his for support as you lowered yourself down completely. You'd never felt so full, your toes curled at the mere feeling.

"You okay, baby?" Dean murmured, hands gently rubbing soothing circles into your back as he allowed you time to adjust.

"Never better," you whispered in reply.

You pulled yourself up into a proper sitting position and gasped as he somehow sank even deeper into you.

Dean worried he'd hurt you until he saw the look in your eye. His concern quickly turned to a smirk of pride. He pressed his hand against your lower abdomen and growled, "You feel that, baby? I'm so deep inside you, you'll be feeling me for days."

You moaned softly, his words having the desired effect on you. You rolled your hips a little and he hissed softly.

"Fuck, doll."

He gripped your hips as you started to move, bouncing up and down on his cock slowly.

His lips attached themselves to your jaw, your neck, your collarbone--anywhere he could reach. He was reveling in the feeling of your soft body against his muscular one, your curves providing him with plenty of flesh to hold on to.

"You feel so good, baby," he moaned in your ear. "Pussy squeezing me so tight--can hardly breathe."

"Feels good, Dean," you whimper.

"Yeah, baby? You like the way my cock feels in your pretty little pussy? Stretching you just right--you were made for me."

You preened at the praise, which only made him want to praise you more.

"This perfect body of yours makes me feel so good, sweetheart. You take my cock so well. Wanna stay here forever just making you feel good--listening to those sweet sounds you make. Fuck, never wanna stop."

You loved his praise, but your thighs were starting to get tired from the exertion. Dean could feel you slowing down, so he pulled you forward, pressing your chest flush against his.

"I've got you, baby. Let me take over," he whispered.

You gripped his shoulders and nodded, more than willing to allow him to take control.

As soon as he felt your body relax against him, he planted his feet firmly on the floor and began to piston up into you. He held you tightly against him to prevent you from moving too much.

"Dean!" you cried, nails digging into his shoulders.

His cock pressed into your g-spot with each thrust and in a matter of moments, you were teetering on the edge of another orgasm.

"Can feel you squeezing me, baby. You gonna cum for me? Huh?" Dean asked huskily. "You gonna coat my cock with your sweet cum, baby? Cum for me, sweet girl. Wanna feel it."

You loved the way he begged and it had you coming undone in an instant. You screamed his name as your walls fluttered around his cock. It took all of his focus not to cum along with you.

"That's my good girl," he whispered. "I'm gonna cum soon, doll. Where you want it?"

"Inside me," you begged. "Please, Dean--fill me up."

"Oh, fuck-" Dean moaned loudly as he came, coating your walls with his seed.

After a few more thrusts, Dean stilled. He continued to hold you tightly against him, needing to feel you close to him as he came down from his high.

He rubbed your back soothingly and placed a soft kiss to your damp hairline. "You were so good for me, (Y/N/N)."

You kissed his shoulder. "Felt so good, Dean."

He smiled and squeezed you tighter. He sighed contentedly, enjoying the feeling of the woman he loved pressed against his chest.

His cock had begun to soften and his cum was leaking out of you and onto his thighs, but he couldn't be bothered. Taking care of you was his one and only priority.

"Do you need some water, sweetheart?" he asked softly.

You shook your head.

"Food?"

You shook your head again.

"Tell me what you need, baby," he begged.

You finally lifted your head to look him in his eyes. "I know it's cliché to say I love you after sex, but I don't care. I love you, Dean...I love you wholly and completely."

Dean nearly breathed a sigh of relief at your admission. "I can't even begin to express how happy it makes me to hear you say those words. I've been pushing the feeling down for years, but I can't do it anymore, (Y/N). I love you with everything I have--it might not be much, but it's yours. You have me forever--mind, body, and soul."

You smiled and gently caressed his cheek. He leaned into your touch and closed his eyes. You kissed him softly, which he immediately returned in kind.

When you separated, you noticed a mischievous glint in his bright green eyes. "Dean?"

"What are your thoughts about round two in my bedroom?"

You laughed lightly. "Are you gonna kick me out of your bed at 2am?"

"Not if you don't snore," he teased.

You smacked his shoulder affectionately and he laughed. "You're lucky you're so damn cute."

He grinned. "Actually, I'm adorable."

You rolled your eyes playfully. "You know, I think I like the idea of round two."

Dean smiled and pulled you even closer. "Hold onto me, sweetheart."

You gripped him tightly and he stood up, holding you to his chest. You wrapped your legs around his waist and he headed towards his bedroom.

When he entered his room, he gently tossed you onto the bed, earning a soft giggle from your lips. He climbed on top of you, pressing sweet kisses to your skin for several moments before finally kissing your soft lips.

"I'm glad you skipped 'Unattached Drifter Christmas' this year," you murmured.

He smiled. "Me too, baby. I think it's more 'Attached Drifter Christmas' now."

You laughed. "I love you, you dork."

He kissed you again. "Not as much as I love you."

The two of you spent the next couple hours continuing to explore each other's bodies, experiencing blinding pleasure over and over again.

Nothing could ever compare to the love you felt for each other, and in spite of everything, you both fell asleep in the comfort of each other's arms, dreaming of the beautiful future ahead.

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