Dean's a Softy

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"I hate you! I am so sick of you coming into my life and then leaving like it's nothing! I hate you, I hate you, I hate you!" You shouted at nothing, wishing your ex boyfriend could hear the thoughts you kept pent up. "Everyone leaves! You leave, my parents left, even Dean leaves! I just wish everyone would stop leaving me!" Little did you know, your best friend, Dean, was creeping through your house to surprise you after a long two months on the road. He heard your screams and immediately ran to your room, but stopped as he heard his name. "E-Even Dean leaves me! H-He always goes on the road and will leave me hanging for weeks, months before he sees me. I just wish someone would stay consistent in my life," You cried out, tears rushing down your face. You covered your face and sobbed into your hands. "Oh, babydoll," Dean sighed, scooping you up off the floor. You blinked away the tears to get a better look at your best friend, who had tears in his own eyes. "D-Dean?" You asked shakily before he sat down with you on his lap. "Surprise," he smiled, pulling you into a hug. "Y/N, what's going on?" "My ex," you sniffed, leaning your head on his chest. "H-He started texting me again, but told me he didn't want me again. Said I was just something to fuck," "Jesus Christ, I could kill that idiot," Dean growled, his grip on you becoming tighter. "Do you really think that I just leave you like that, Y/N? You think I want to leave you here?" "I-I-" "I don't want to leave you here while I go to work, Y/N. If it were my choice, you'd come along with me," he said, reaching to wipe your tears away. "I hate when you leave, Dean," You said shakily before tears spilled over again. "I-I hate when I have to say goodbye to you and let you drive away," "I hate it, too, Y/N. I wish I didn't have to leave you here," he sighed, kissing the top of your head. "God, it hurts so bad," you said, looking up at his tear filled eyes. "I know," he nodded, smiling down at you. "And it hurts because I cant tell you why it hurts me so bad, I-I promised myself-" "Y/N," Dean almost warned you, raising a brow. You cursed yourself for saying anything, but couldn't help it. He had to know. "I-I'm probably only saying this because I'm sad, but please don't let it ruin anything, Dean," you begged before he sat you up, his eyes burning holes through yours. "Go on," he encouraged you kindly. "I-I love you, Dean. I really do. We've been best friends for years and years, and when you started leaving, I-I realized I liked you more than a friend," You admitted quickly, wiping your tears away. "My ex was just someone who got my feelings to go away temporarily and that's why I was so scared of him leaving. I-I hate that I love you so much because you're gone all the time. I-I try and distract myself, but whether you're here with me, or across the country, you're all I think about, and-" You were interrupted by Dean's soft lips pressed to yours. His warm hand cupped your cheek as his lips moved gently against yours, and your hand moved to hold his shoulder. "I feel the exact same way, Y/N," Dean whispered as his forehead rested against yours. "R-Really?" You asked, peering at his bright blue eyes. "Hell yeah. You are a lot better at putting it into words, though," he chuckled before kissing you again. He nuzzled his face into the crook of your neck as you let out a sigh of relief, your tears finally stopping as Dean held you tightly. "I love you, too, Y/N. I never thought I'd get to tell you because of that guy. I want you to be all mine, okay? I want to be all yours," "I'm all yours, then," You smiled, pulling away to look at his smiling eyes. "You're beautiful, and sweet, and kind. I've wanted to just tell you that all this time, but you'd think I was lying," he said, rubbing his hand on your back. "God, I hate that guy, Y/N. He has ruined your ability to believe in what you truly are, which is beautiful, amazing, sweet, sexy, phenomenal," "You really think so?" You asked, rising your brows as his hands moved down your waist. "I know so," he smiled, leaning in to peck your lips. "I-I really appreciate it, Dean. I-I just don't think that I am-" "Do I need to show you? Do I need to prove it to you?" he interrupted you, moving you to sit on the bed. "Wh-What-" "I'm going to prove that you're beautiful," Dean said simply before crawling over you, pressing his lips to yours. His hands moved gently down your body, squeezing every curve on the way down to your sweatpants waistband. "May I?" "Y-Yes," you breathed between kisses. He pulled the sweats off you, dropping them to the floor before kneeling down between your legs, resuming your hot make-out session. His hands found the material of your T-shirt, pulling it up and over your head swiftly. "You are beautiful, Y/N," Dean hummed, kissing down your neck before pulling away. He stood up, pulling you up with him before he undid the belt on his pants, pulling his shirt off quickly before kicking the jeans to the side. "God, you are fucking beautiful," "Dean," You whispered before he pulled you into his strong arms, kissing you softly before his hand trailed to unclasp your bra. You and Dean have had sex before, but it was drunk, sloppy, meaningless sex. It was rough and full of lust, just to get you both off. You never knew he could be so gentle, the way he was being with you now. His kiss was gentle, and his touch was softer than ever. You never knew you'd find this side of Dean. You'd only ever expected rough-housing, harsh, hard-ass Dean. "He's an idiot, y'know? You're a fucking goddess," Dean said before scooping you up and laying you down on the bed. "If I have to make you cum two, three, four, five times before you know you're beautiful, then I will. You deserve to be treated good, babydoll, and I will be that person who does treat you good," "Dean," You whimpered as his hands hooked the material of your underwear, tugging them down your legs. You tried to cross your arms over your stomach, covering up your pudge before he grabbed your wrists, pressing kisses to the backs of your hands. "I love you, Y/N. I love all of you," Dean whispered before hovering over you and placing your hands on his cheeks. "I'm going to prove it. I am going to prove that I love you and that you are the most beautiful thing I've ever laid eyes on," "I-I love you, too, Dean," You said before his tip lined with your entrance. You let your eyes close as he thrusted into you, filling you up and taking your breath away. "You're beautiful, gorgeous, pretty, sexy, y'know?" he hummed as he picked up a quick pace, making you moan softly. "Fucking angelic," "D-Dean," You moaned, letting your fingers slip into his hair. "God, even your moans are fucking beautiful," he groaned, his eyes drinking in the appearance of your naked body underneath his as he penetrated you over and over again. "I'm going to tell you all the reasons I think you're beautiful," "Dean, you don't-" "That, right there, is beautiful. You're blushing," he started, all while you kept back moaning over his talking. "Your personality is fucking amazing. You're sweet, kind, caring. You stop at nothing to make those around you smile. Y-You're just plain, flat-out, fucking gorgeous. Your sparkling eyes are so fucking beautiful. I love the way they look when you look at something you love," "Like you?" You asked as your arms found a resting place around his neck. "Yeah, I suppose like me," he smiled. "I was thinking more like pizza, but-" "I love you more than I love pizza," You assured him matter-of-factly. "A-A lot more," "God, I love you, too," he moaned, moving his hands down to your waist, gripping your hips tightly. "F-Fuck. Anyways, babydoll, you're just... beautiful. Your cute little smile, your cute hands and the way they fit perfectly into mine. Even hugging you, you're just perfect. You fit just right against me, and it makes me feel complete," "You're gonna make me cry again," You laughed, letting your eyes fall closed. You probably would have been crying if it weren't for Dean's cock being buried deep inside you, filling you up every time he thrusted against you. "Don't cry, babydoll," he said softly, reaching to cup your cheek with a gentle hand. "Just enjoy yourself. I want you to cum, and I'll be damned if you don't cum more than once. Enjoy the ride, baby," "Dean, it's-" you were interrupted by Dean's hips meeting yours at a furious pace, sending tingles all down your body. You gripped his muscular shoulders as he pounded you, fucking you into complete oblivion, sending you over the brink into orgasmic bliss. "That's right, baby," he grunted, reaching to rub your clit with heavy, lazy pressure. "Fuck, Dean!" You moaned, nails digging into his perfect skin as you started cumming. You cried out in complete pleasure, a flow of expletives pouring from your mouth as Dean finished you off for the first time, and his lips pressing to the sweet spot on your neck. "Oh, Dean," "You're so alluring, baby," he hummed before giving you a small resting period, letting your walls relax around him. "Absolutely stunning," "I've never felt so-" "Beautiful? Well, you are. And you better get used to it," he said sternly before sliding back into you, making you gasp. You held his body close to yours as he moved slowly against you, letting you feel every detail on his cock. "Dean, I-I won't last long this time," You let him know in a shaky whisper as you could already feel the knot in your stomach start to come loose. "Don't worry, baby, I'm close," he hummed as you tightened around him, hoping to get him off before you. You felt so selfish cumming before him, plus adding a second orgasm on top of it? You wanted to make him cum. "Holy fuck, Y/N," "C-Cum in me, if you want," You told him as he nodded, nod you wrapped your legs around his body. You gasped as he titled his hips, using his expertise to try and get you to cum first by hitting your g-spot. "How does that feel?" he asked soothingly as you choked on your own moans, struggling to catch a breath. "S-So good," You managed to whimper before Dean's hips picked up speed, and you could feel his cum pour into you, his cock pulsating and twitching inside you as he came. "Fuck," he hissed before thrusting faster. "How close are you?" "Y-Y can stop if you want. You don't need to-" "I said, how close are you?" he repeated, cupping your chin. "My beautiful baby needs to cum again. Don't you?" "Y-Yes," You moaned, tightening your legs around him a you could feel the heat spread over your entirety. "There we go," he hummed deeply. "God, babydoll. You're fucking fantastic," "I-I'm gonna-" You started before Dean buried himself a deep as he could in you over and over again, still hitting your g-spot. You spilt over as your body began quivering under his touch, and your walls convulsed around him, triggering another orgasm for him, as well. You felt him spill into you again as you finished cumming, and he collapsed on top of you, both of you panting for breath, your sweaty bodies sticking together as his lips found yours. "I-I've n-never felt s-so good," You admitted, letting out a deep sigh as he rolled off you, pulling you into his arms. "My pretty baby deserves to feel this good all the time," Dean said breathlessly, pressing his lips to your forehead. "No more will you be hurt, Y/N. The only time you'll ever be crying is if my words about you make you emotional. You're a fucking beautiful, astonishing woman, and I'm glad to call you mine," "I-I have never seen this side of you," You said, hands trialing down his toned arms. "So gentle and kind," "What can I say? I'm a softy for you," he smirked, kissing you gently. "I-I love you so much, Dean," You whispered, cupping his cheek as he pressed his lips to yours again. "I love you, too, babydoll," he hummed, rubbing soft circles on your tummy as his eyes trailed down your body and back up to your face. "And I initially came here to surprise you with some news, but this made that news so much sweeter," "What?" You asked excitedly, raising your brows. "Tomorrow, you're quitting your job. Sunday, we're flyin' the hell out of here and you're going to start traveling with me," he said, making you jump up with excitement. "Really?!" You gasped, covering your own mouth. "Mhm. After months and months of me buggin' Vince, he's finally letting me bring you along," he smiled as you jumped to your feet, which you immediately regretted as the contents inside you shifted and slid down your leg, making you blush and squeeze your thighs together. "Erm, I-" "Let's get you showered and cleaned up, baby," Dean chuckled, standing up to scoop you effortlessly into his arms, walking you toy he bathroom where he showered you, all while still telling you the reasons you're beautiful.

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