Regular Check-ins

"Hey wait, don't do that. Come here and let me take care of you." He reached out and you couldn't even make eye contact with him.

"That's okay Dean, you don't have to."

"I know. I want to. I don't know why my body's not cooperating."

"It's not cooperating because you can't force yourself to be attracted to me. It's alright. I know I'm no prize." The last word came out with a tear that welled up in your eye as you moved to your desk and pulled a sweatshirt from your chair further covering yourself from his eyes.

"I'm not forcing myself. I...this isn't you...I mean it must be the booze." He sounded so beside himself as he spoke, but you still didn't look up.

"Forget it...I just...I have to go to the bathroom." You left quickly and made your way into the bathroom in your hallway. In another minute, you were on the floor with the door locked crying silently into your hands.

You stayed there for what seemed like an eternity. When you heard no sound for a while, you slowly opened the door peeking out. You could just see into your room, and there was Dean sprawled out snoring lightly. You closed the door behind you and made your way out to the living room. The world had crashed around you and you had no idea what you were going to do next. Dean was practically your best friend and you had ruined it all by coming on to him when he was clearly too drunk to say no. Now, he couldn't even force himself to be with you, and that gave you the final signal. There was no way that you were recovering from this. After your excitement at seeing him, now you knew that you would never see him again.

A few hours of pacing, and you finally wrote a note for him. You threw on flip flops and grabbed your purse slipping out of your own apartment at about 5 am. You taped the note to the back of the door and let it close softly.

It said what you didn't have the guts to say in person:

"Dean, I'm sorry I tried to force you to be with me when it's not what you wanted. I wish I hadn't because now I know what a fool I was for hoping. Can you please leave before I get back? I can't bear to see you right now. And I'll completely understand if you never contact me again. Thank you for all the fun times and please remember me without the embarrassment of what I did last night."

A few hours later, after a quick breakfast and a mini nap in your car, you pulled back up to your apartment with caution. When you saw that the Impala was gone, you parked and made your way up the stairs to your place. When you went inside, you searched through the rooms, assuring that Dean was gone and then sat down on the couch. Your phone sat on the coffee table, and you breathed a sigh of relief because you thought you had lost it somewhere when it wasn't in your purse.

You picked it up to see if there was a message, and found a note folded up on the table beneath it. The paper was folded up into fourths and you didn't unfold it. After the night before, you just wanted to forget Dean Winchester and you figured you knew what that note was going to say. It would be full of apologies and trying to make you feel like you weren't the ugly, fat girl that you knew you were. That was the last thing you needed was more pity from Dean Winchester.

At some point that day, the note went into your room, in the back of the paperback you were reading and that was that. There were no texts or calls from Dean on your phone and your life went back to normal. The occasional memory would surface over the next few months and you would push it out of your mind, hoping that it would fade as time went by. The note made its way from one novel to the next as the months went by.

*************************

Everything seemed to be okay until the day you pulled up to your apartment and saw that familiar black Impala parked outside. Your heart sank. The thing you had been avoiding all along could no longer be avoided. Dean had come to put the final nail in your coffin after six months of not seeing or hearing from him.

You grabbed your bag and made your way up the stairs. Sure enough, the gorgeous man sat on the floor outside your door as you approached. When you stood before his feet, he lifted his head in silence.

"Why are you here?" The question came from your mouth as you marshaled your best defense against the hurt you felt at seeing him again.

"You didn't call or text so I wanted to hear it from you in person." He said the words as he stood up.

"What are you talking about?" The words he said didn't make sense - hear it from you in person? What the hell did that mean?

"You got my note right? So, you didn't text me or call me to answer. I gave you six months to the day and nothing."

"Dean I got your note, but I didn't read it."

"What? Are you kidding me? I've been waiting for six months to get an answer and you didn't even read it? Well, do you still have it?"

"Maybe. What does it matter? I know what it says. Just go away Dean." The words stung you as they came out.

"No. I'm not leaving until you read the note I left. Now, go inside and get it and come back here so I can watch you read it." He was stern, almost frightening as he spoke and grabbed your arm pointing at the door.

You went inside heading for your latest book and pulled the note from the back cover. A quick walk back outside with only your keys and the note and you suddenly understood the fear that Dean could put in someone. You felt like you had to obey him, there simply was no other option.

"Good, now open it [Y/N]." You looked at him briefly before unfolding the stiffly creased paper. Your eyes went to the first word and you swallowed thickly.

"[Y/N], I'm not sure what to say to you. I know why you locked yourself in the bathroom and why you left. It's because I'm a piece of shit asshole. I waited all this time to finally do what I wanted to from the moment we met, and I fucked it all up. Please understand that you didn't force anything and you have nothing to be sorry for. And, you're no more of a fool for hoping than I was. The difference between us is that your body worked when you needed it to and mine was so full of whiskey that it apparently couldn't. You have no idea how many times I have thought about you and been rock hard and yet for whatever reason I couldn't get hard when I finally had the chance to show you how I really feel. [Y/N] know that I love you, truly love you and I think you are the most beautiful woman I have ever seen. Despite all my stories, I haven't touched another woman or even thought of another woman since I've known you. No other woman compares for me. I hope you read this and can think of me without the idiocy and embarrassment of what I didn't do last night. Please message me or call me to tell me if you feel the same way or if you just want things to go back the way they were, because I can't stand not having you in my life one way or the other. I'll wait until you respond to come back. - Dean"

You finished the last words and looked up into his eyes. He was pleading with you for an answer with no words. Suddenly, you saw it there, the dread, the hope, the way the six months of no contact had weighed on Dean.

"Well...don't leave me hanging here [Y/N]." He searched your face for an answer.

"I...I thought you were just doing that because you felt bad for me...I..." You didn't know what to say to his letter, no ideas would come to you.

"Are you kidding? I figured all the times you let me stay here and hang out you felt bad for me. I have only pitied you once and that's when you lost your family. I've watched a strong, beautiful woman since then, and just prayed that she would see me as more than a friend."

"What?"

"You kissed me that night, and I wanted so badly to believe you felt the same way. When you said yes, I wanted to give you every ounce of feeling I had for you that night. And then when I had whiskey dick...fuck...I was so angry. I waited for you to come out of the bathroom and then I fucked up again passing out. When you left, I just fucking lost it. Then, I waited for you to get in touch, just waited and nothing."

"Dean, I didn't know. I mean look at me and look at you. Why would you ever..." A tear came into your eye and you scanned his face for an answer.

"Why would I ever what? Drive 6 hours from where I live and pretend I was in the area just to see you for a day? Why would I force my brother to stop with me the one time we were only 2 hours away? Because I fell in love with you, that's why. And, I never want to hear you say that you aren't beautiful or question how your body looks. You damn near killed me when I got you naked. I haven't been able to get that incredible picture out of my head, and trust me I had no trouble getting hard thinking about just how you looked."

"Jesus, you really lied to me all those times about being in the area?" The question slipped out as you let everything sink in.

"Would you stop asking stupid questions and let me in so I can finally show you how I feel?"

Your words ended at the sound of gravel in his voice. You opened the door and went inside letting him follow. Dean turned locking your door. He stopped there, leaning down and took off his shoes. He pulled his flannel shirt off and tossed it towards the couch. You were frozen not sure what would happen next.

"Don't just stand there, strip. Or, I'll have to undress you." Your eyes opened wide at his words and you stood staring at him like a deer in headlights. "Okay, you asked for it."

Dean rushed at you seizing you by the hips and throwing you over his shoulder like a sack of potatoes.

"Dean? What the hell are you doing?"

"What I should have done a long time ago." He said the words gruffly and you went along for the ride.

When he reached your bedroom, Dean bent down standing you on your feet. Then, his hands were on you. He peeled your t-shirt up and off of you. His fingers unsnapped your bra quickly and both items found their way to the floor.

"Hello ladies, I've missed you." He gave you a slight grin and dropped to his knees. Your shorts were undone and being pulled off in the next instant he was pulling each of your shoes off. When he was done there, your panties followed leaving you stunned and naked at the foot of your bed.

"Um...okay." It was all you could say as he stood back up and looked you up and down. Your hands went up to cover yourself, and he gently guided them back to your sides.

"Shhh...just let me look for a second." He pressed his fingers to his lips as you stood there waiting, terrified. "Alright, now raise that beautiful face for me." You complied, waiting for his next command.

"There we go perfection. [Y/N] you are completely perfect. I love your face. It's so kind and bright, and god those eyes haunt me." He walked up placing his hands on the side of your face and tilting it up to look at him. His lips descended placing a kiss on your lips softly before he pulled back again.

"I love your neck, it's so soft. He leaned down placing a kiss on the side right in the spot that made you shiver.

"And, these, well my god they are a work of art." The back of his hands grazed your breasts as he looked into your eyes. His mouth descended then as his arm went behind you leaning you backward so he could place a kiss on each of your nipples.

In the next moment, he picked you up and laid you back on your bed while he still stood at the foot looking you up and down. You were still taking all this in, trying to make it make sense and afraid to make a move and end it.

"This stomach, is so beautiful. I love the way your sides dart in leading me down exactly where I want to be." He knelt down and placed a kiss on your belly button and you sighed.

"Oh, these hips, my god, how juicy. I have wanted to taste these so bad since I left here." He kissed each of your hip bones before leaning to the side and licking a stripe up your left outer hip. He moaned at the taste.

"Dean...I..."It was your first interruption and met with a quick look.

"Nope, no talking yet." He raised a finger at you. "Now, these feet are just perfect. You always have your toes painted, and it drives me crazy. I wonder every time I show up what color will be on these and I'm never right, not once. Even now, I figured yellow for summer, but no they're silver. I mean silver?" He kissed along the top of one foot and then the other.

"Now these legs drive me crazy. You wear those damn sleep shorts every time I'm here and I think about how soft they look. You have this silky smooth skin, and I can't wait for you to wrap those sexy legs around me." Dean placed alternating kisses up your legs softly caressing the skin in a perfectly chaste way that was making you get hotter by the second.

A grin spread across his face as he stood up. Then, in a flash he flipped you over on your stomach, scooting you a little further up the bed as he did it.

"Your back is even beautiful, damn. I mean I don't think I've even seen these little butterfly tattoos, but now...well..." He leaned down placing kisses across your shoulders where you had a dozen small butterflies tattooed dancing across the skin.

"Now as for this ass...I mean come on. How can a guy look at this ass and not have dirty thoughts. You have got to have the hottest ass I have ever seen on a woman." He placed a kiss on each of your butt cheeks and then flipped you over with ease once more.

"Then, there's my favorite part. The one place I didn't get to see that night, just feel. Fuck, I didn't want to wash my hand after I left. I could smell you on my fingers and it was driving me crazy. I almost cried when I had to take a piss because I knew I wouldn't smell like you anymore. But, now..."

Dean motioned to you to slide up the bed and you did as ordered making your way to the pillows. This was all so surreal and you wanted nothing more than to do as he asked.

He climbed onto the bed at your feet and reached one arm over his head pulling his shirt off easily. Dean's pupils were blown wide with lust as he leaned down circling your legs with his arms. He planted a slow kiss on each of your inner thighs and then dove into your pussy. It started with slow kisses along every surface and then he plunged his tongue into your wet heat.

"Oh fuck Dean." The words sighed out of you on their own as he continued. His tongue slowly circled your clit and then just as quickly as he began he stopped. Your eyes had gone shut and now you opened them looking down at him.

"There you go, now keep your eyes open. I want you to watch how much I enjoy you." You focused on his face as he went back to licking and sucking at your core in ways that had never been done to you. With everything, you had forgotten how nervous it made you to be eaten out. Now, you were completely caught up in the feel of Dean's hot breath on you and how good it felt.

"That feels so good Dean." You spoke to him as he looked at you with nothing but lust on his face.

"Good. Lay back and just come undone for me." He sounded like pure liquid sex from between your legs and all you could do was comply. In another moment, a finger slid into your dripping core. He drug it out slowly stopping as the tip hit that perfect spot of flesh inside.

You gasped and your head fell back, eyes closing automatically.

"Hey, eyes on me." He tapped your inner thigh startling you. Your eyes opened and your head tilted forward. He smiled and went back to his ministrations on your clit.

"Fuck, you're so tight. Gonna feel so good on my cock." He moaned into you as he slid a second finger inside joining the first.

"That feels so good...oh, oh...Dean...please." You panted now feeling your muscles tighten as his lips pulled your clit in.

"Please what? Tell me what you want [Y/N]." He growled as a third finger slid into you and you moaned out loudly.

"Please make me cum...I'm so...close." You could barely think as you stared down into his burning green eyes. He was so insanely hot right now and completely focused on you.

"I want to make you cum all night." He said the words before sucking on your clit with full force and pulling all of his fingers up at once. He rocked them against the bundle of nerves inside connecting every place that felt good on you at once it seemed and you cried out his name. A hand flashed out and grabbed the back of his head as your pussy pulsed against him and around him at the same time. The orgasm ripped through you and you were left to pant and moan in its aftershocks as he pulled his fingers from you.

Soon he was up hovering his face in front of yours.

"Now, do you understand how beautiful you are?" He stared into your face holding your chin so you faced him as he held himself above you.

"Dean...I..."

"Say it. Tell me you're beautiful." He held you there transfixed.

"I...I..."

"Come on baby say the words. I want to hear you say it and believe it."

"I'm beautiful." It took everything in you and you felt a wave of strange relief and realization wash over you.

"That's my girl, now are those condoms expired by now?" He smiled at you and captured your mouth before you could answer.

You reached over to the nightstand, pulling a packet out and looking at the date. Thank god the answer was no.

"Nope, still have a few months. You saw me check last time?" You smiled faintly at him.

"Baby, I remember everything from last time. Now, what do you say you try to put it on me again?" He smirked at he rolled onto his back undoing his jeans. They slid off easily and his underwear soon followed. And your eyes fell to his dick, which stood hard and proud already dripping.

You opened the foil packet and this time slid the condom on him easily. It felt so good to have that hot skin on your hand, and if you weren't so damn excited you would have paused to give it a few strokes. You wanted him though, more than anything.

"[Y/N] that's all because of you. You made me that hard, not when I was eating you out. Oh no, long before that. The moment I even think about you my body responds. Do you believe me?"

"I...I want to but..."

"Whoa, no buts, that's the truth. I want you and only you. You turned me off from any other woman but you, so don't you dare question if I want you. This cock only gets hard for you now. So, tell me what you want to do with your cock." His words were thick with sex and you looked into his eyes searching for some deception. There had to be something wrong with this picture as you looked at the sexiest man you had ever known. But, no, it was just Dean, full sincere, open Dean.

"Please fuck me, please."

"On one condition." Dean rolled himself over your leg settling into a comfortable place with his lower stomach on your curls.

"What?" You were breathless with anticipation as he slid himself up until just the tip of his cock was at your entrance.

"Tell me you're beautiful again."

"Why Dean?"

"Because I'm gonna make you say it constantly until you believe it. I want you to see yourself the way I see you." Your eyes welled with tears again as you looked back at him.

"I...I'm beautiful."

"That's my girl." He moved up taking your mouth with his and slid himself inside of you slowly. It stretched you so well and reminded you of just how long it had been since you had been with anyone else. It was before your parents died, and the faint stings reminded you of that.

When Dean was fully seated inside, he pulled his mouth away staring into your face.

"Are you okay?" His words pulled you from your focus on breathing and adjusting and you looked at him.

"Yea...just need a minute to get used to my beautiful cock." You whispered it as you breathed slowly willing your body to relax and enjoy this moment.

"I'll try, but you feel so good...I mean...unh you're so tight." He was almost shaking trying to hold himself back and you were the goddess again in your mind. You had Dean Winchester inside of you and he had to use every ounce of strength to keep from pounding into you.