Old Friends

I Love You

Warning, Smut content

You smiled, Dean really did love you. You pulled him back to you and kissed him with as much love as you could muster. Breaking free you looked up at him as your cheeks reddened, "Will it hurt?" Dean took your hands from around his neck and held them in his own. He placed a gentle kiss upon each one and looked back at you. "It will at first, but we can take our time." You weren't too thrilled about the pain part but one more look into Deans eyes and you knew you were ready. You nodded once and Dean smiled. He once again slid his hands under your thighs and lifted you off the dresser. You wrapped your legs around his waist and began kissing his neck.

Dean walked towards the bed and laid you down gently. He stood at the end of the bed just taking in the sight of you in nothing but his shirt. He smiled and pulled his own shirt over his head. Your eyes grew and clouded over with lust at the sight of his strong chest. He smirked at your reaction, kicking off his boots he then removed his pants leaving himself only in a pair of boxers. Climbing onto the bed he hovered above you and began kissing you, lightly biting your bottom lip begging for entrance. You opened up to him and he took the opportunity while you were distracted to begin unbuttoning the only thing between him and your body.

You felt the buttons coming undone and again you tensed up. What if he didn't like what he saw? You weren't a model, what if he decided he wasn't attracted to you after all? Dean saw the worry in your eyes, kissing you once again he undid the last button and slid the material to the sides. Slowly he began kissing your cheek and then neck. Working on the same sensitive spot you seemed to enjoy earlier, trying to help you relax. 

You began to slowly loosen up and enjoy the attention he was giving you. Dean began to lick, kiss, and suck his way down to your chest. Once he reached your chest he brought one hand up to intertwine his fingers with yours and lay it beside your head. His other hand skillfully gripping your waist while his thumb drew circles on your skin. You began squirming, feeling like your body's senses were heightened. Suddenly Dean rose and lifted you up with him, kissing you once more he sat you so that you straddled his lap.

While looking into your eyes he slid the shirt off of your arms and threw it on the floor beside the bed. Looking down and taking in every inch of you, he couldn't help but shake his head. "Your so beautiful," he said. Feeling a huge weight lift from your shoulders you smiled and kissed him. For the first time in your life, you actually believed it. 

Gaining confidence you pulled dean towards you then turned to push him onto his back. You wanted to show him how much he meant to you too. You straddled his waist, instantly coming into contact with his rather large friend from the feel of it. The sensation made you moan and you leaned down to kiss just below his jaw. He put his hands on your hips and you began kissing his neck and chest.

Without really thinking about it you automatically began moving against him, rubbing your sensitive spot again his groin and earning loud moans from him. After a few minutes of this Dean couldn't take anymore and quickly flipped you over so that he was positioned between your legs. He quickly took off his boxers. You looked down to see his member and for a moment had the worrying thought that it might not fit.

 He seemed to read your mind and chuckled, "It's okay baby, we're gonna take it slow." You nodded and Dean again hovered over you, before he entered you he wanted to try and prepare you for what was to come. Kissing you while slowly kneading your breasts he waited until you were moaning into his mouth before he removed one hand and slid it down to your center. Slowly he pushed in one finger, stilling the moment he felt your hands clamp down on his shoulders.

Continuing to kiss you he slowly pulled out his finger and re-entered. You began to relax once you became accustomed to the sensation and once you seemed to start enjoying it he inserted another finger. Then after a few minutes a third. After awhile he figured there was no way he could make you any more ready. Removing his fingers he used his hand to grip under your thigh, slightly lifting. His other hand entwined with yours again and he looked you in the eye.

 "Are you ready?" You nodded, he could see the fear and worry in your eyes but he also saw confidence and love. Slowly he lined himself up and began entering you. The hand that was holding his squeezed hard and your other hand gripped his bicep. Dean stilled and gave you a moment to adjust, after a minute you signaled him to continue and he finished fully filling you. You let out a slight whimper and he stopped once more.

He smiled at you and kissed your cheek, laying his forehead against yours, the urge to move increasing with every second. "Your doing so good baby I promise it will feel good in a minute." You nodded and kissed him, kissing Dean somehow made everything better. You suddenly realized the pain was slowly turning into something else and motioned for Dean to move. He slowly began moving, coming in and out and circling his hips with skilled thrusts. After a few minutes you began to feel something building up in your lower half and couldn't stop the moans.  Deans name kept from coming out of your mouth in a breathy voice. 

"Dean, oh god!"

He knew you were close, he fought back his own release, he wanted to feel you come apart around him. Leaning down to kiss your neck and suck on the sensitive spot under your ear he twitched his hips at the same time and suddenly an overwhelming feeling of pleasure filled you. 

It seemed to go on and on and you rode out the waves happily. Dean continued to kiss and suck all the while pushing in and out trying to help you ride out your pleasure longer. After a few more thrusts you suddenly sat up and flipped Dean over once again. He made no move to stop you as you lifted yourself onto him and reveled in this new angle.

He had just given you immense pleasure and you were going to return the favor. After finding a steady rhythm you watched as Deans eyes closed and he threw his head back. You leaned down to pepper kisses along his chest and took one of his nipples into your mouth. Sucking the hardened tip caused Dean to let out a loud moan and you were very proud to coax that response from him. Dean grabbed onto your hips and began helping you ride him faster. 

"Fuck baby!" You suddenly felt deans release, you continued to thrust a few more times hoping to prolong his orgasm. Once he had ridden his pleasure out you slowly climbed off of him and laid down at his side on your back, suddenly feeling exhausted. Dean turned onto his side to face you, leaning his head on his elbow.

He stared at you with a big smile on his face, you turned your head towards him and blushed. Dean laughed at seeing your adorable blush and leaned down to kiss you sweetly. Using his free arm he gently pulled you up against his body, your back to his front. Reaching down he pulled the blanket over the both of you and wrapped both his arms around your body. Burying his face into the crook of your neck he placed a kiss there. "I love you Y/N."

You smiled sleepily and hugged his arms around you tighter, "I love you too Dean."