Regular Check-ins

And, there he was again at your door. Dean gazed at you easily and you felt the calm that he always brought with him. It wasn't the first time he had come to check on you since your whole family was slaughtered, but every time it made you feel better. It probably shouldn't have because the memories of that horrible night always came back to you, but there was something about the green-eyed hunter that made you feel better.

Since that night, every time Dean and Sam were anywhere near your tiny Midwestern town he stopped in to do what he called a 'regular check-in.' Sometimes he would call first, or text that he was coming over. Other times, he would show up unannounced. When you weren't there right away, Dean usually found his way over to the bar and would come over afterward a little drunk. You never really minded because he was always respectful and would crash on your couch. There were even times where he would bring Sam with him and they would both take up your living room furniture.

Dean's presence was starting to be a regular thing, and you didn't mind. At first, you were a little awkward, but now he was almost like family. Plus, he was pretty nice to look at, let's face it. As time went on, you forced yourself to look at him more as a gay best friend or a brother. It was easier than the thought that he wasn't attracted to you, especially because you were clearly attracted to him.

Today though, you had been at work when Dean messaged that he was coming through town. Apparently, he dropped Sam off with some guy named Bobby, who was like his dad. This wasn't the first time you'd heard the name, and you had long ago figured out that Bobby must live nearby because that seemed to be where Sam would go when Dean came over for his 2 or 3 day stay with you. Of course, with you at work, you figured Dean would be coming over a little drunk tonight and boy were you right.

Now, you had been home for two hours and Dean had just arrived. That dopey grin on his face that was almost too adorable told you everything as you ushered the gorgeous hunter inside.

"Hey beautiful, how are you?" He slurred a little, which meant this was one of those times where you needed to get him some water and put him to sleep on your couch.

"I'm doing well Dean, pretty well. Come in and let's get you out of those shoes and that coat." You ushered him in, and he slumped onto the couch. You were quick to help him remove his coat and take off his shoes.

"You know, I can do that myself."

"Would you just stop? We can talk more tomorrow, but for right now you need some sleep drunky."

"Why don't we have some more drinks together and then we can both be happy?"

"Because you need to sleep, and I'm tired too. We can hang out tomorrow alright." And with those words, you got up pouring him a glass of water from your fridge. When you returned, he already had his eyes closed and his breathing had evened out. You put the drink down on the coffee table out of reach a little so he wouldn't hit it if he had one of those damn bad dreams that woke you both up sometimes. A quick blanket thrown over him and you were heading to your room.

That familiar calm surrounded you as you lay there, feeling the protection that came with having a hunter in the other room. You read a few chapters of your book and crashed out. The door to your room was open, and unlike usual you slept in shorts and a tank top. After all, the last thing you needed was for Dean to see you naked. You didn't need to see the disapproving look in his eyes at the sight of your less than perfect physique.

You left the door open, of course, because Dean might need something and the motherly part of you always wanted to take care of your savior. After the first time he stayed, you knew he had demons. That first night, Dean woke up yelling in his sleep and you had raced out of your room to see what was going on. He looked at you terrified and you had gone to his side holding him a little, until things calmed. He never wanted to speak about what was in his dream, but he was so thankful to have you there. That much you knew.

Of course, the bad dreams were better than the other two alternatives. There was the situation that you worried about a little tonight. When Dean had a bad time, he would drink a little too much and after the night he threw up all over your floor trying to find the bathroom, you were always on the lookout for the sound of him stumbling about so you could jump out of bed to help him. And finally, there was that unfortunate night where he was having some sort of PTSD flashback and was wandering around your apartment with his gun drawn. It ended with you terrified, and him visibly shaken. The shock of him storming around had you worried about going to sleep without knowing if he would throw your door open and take a shot.

All of that added up to you asleep soundly, but with one ear out for your guest to make sure he was okay. That's why you heard the noises at around 3 am coming from the living room. It was rustling that woke you at first. Your eyes popped open just a little, taking in the sounds to determine if it was worthy of you getting up or just him rolling over. When you heard the sound of Dean breathing heavier in the other room, well that was a signal. You figured he was probably having a bad dream.

The dim lamp in the corner of the living room was the only light source as you crept down the hallway in your dark apartment listening. You would usually watch him to see if it was bad enough to wake him. There were times, he would wake a little and just roll over. You always tried to preserve his dignity by not being seen when it was just one of those. Something inside told you there was a whole lot that Dean had seen in his life that caused his nightmares, and the last thing you wanted to do was highlight that dark part of him.

Now, though, you heard a rhythmic shuffling and Dean's breathing was heavy. Fearing the nightmare was truly horrific, you made your way to the edge of the hallway. You could hide in the shadow here but still see all of Dean. Your face flushed immediately as you took in the full appearance of him before you.

Dean had his jeans undone and those and his boxers were pushed midway down his thighs. His shirt was drawn up exposing his gorgeous chest and abdomen, a tan landscape of hotness that was only broken up by a few scars. As if being on display like this wasn't enough to make you turn crimson, there was what Dean was doing. He had one hand stroking over one of his nipples in time with his other hand that stroked up and down his cock. It stood magnificently out, making your body quiver. You had never seen Dean in any real state of undress, but here he was and you could see every inch. Dean's cock was bigger than you expected and even his large hand didn't take away from the girth that was there. It was truly a riveting sight.

You should have left, but it was paralytic to watch him stroke up and down, playing with his tip every so often as a bead of precum would gather. His every sigh and moan had you in suspension as you watched him move faster and faster. If his eyes weren't opened here and there, you would have sworn he was jerking off in his drunken slumber. But, no, he knew exactly what he was doing - just not what he was doing to you. The crush you had on him forever was never going to go away if you kept watching as he jerked himself off on your couch.

"Huh...oh [Y/N]...yea just like that beautiful." Holy fuck, he just whispered your name. You froze, not sure what to make of what you just heard, but knowing that you were going to watch this to its inevitable conclusion.

"Uh...yes...oh you're gonna make me cum baby. Uh...huh...oh [Y/N]." With the last sigh of your name, Dean tilted his cock a little and looked down watching just as you were as cum shot across his stomach. It was mesmerizing to take in the sight of it. Dean's face pulled tight in pleasure, and then relaxed completely when he finished and lay there breathing heavily as he came down.

You watched him for another moment, until you saw him shift on the couch, carefully holding up his shirt as he reached over to your tissue box. Then, you panicked in your mind and scampered quickly down the hallway and back to your room. The last thing you wanted was to be caught spying on Dean like that.

From your bed, you heard him a few minutes later make his way into the bathroom in the hallway. He ran the water a little, and flushed the toilet before you heard tentative footsteps come down the hallway to your room. You heard him enter your room as you lay there curled up with your head buried in your pillow.

"God you're beautiful when you sleep. Fuck I wish I could hold you. Sleep well [Y/N]." He whispered the words as you pretended to sleep. How could this be happening? How could Dean even be thinking about you that way? He had told you about dozens of hot women and I mean come on just look at him. This was Dean Winchester and for some reason he was saying those things about you.

Long after Dean left and you heard him plop down on the couch again, you lay in bed pondering those questions. It was all so much and when sleep finally came back to you, your dreams were filled with oddities that signaled your anxiety.

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

The next morning you awoke to the usual. Dean was in your kitchen, coffee in hand, making breakfast. You had learned to always have some bacon on hand because he loved to make that as well as those damn crescent rolls that you bought tubes of at the store. He always wanted to make a full breakfast while he was with you, insisting that he didn't get to eat like this when he was on the road doing cases.

"Good morning, feeling good or hungover today?" You started off simply as you pulled your sweatshirt down over your tank top. You never wore a bra under those, so you weren't about to give Dean a show he may not want. Although after the night before you were starting to wonder. Mostly, though you were wondering if you had dreamed the whole thing up.

"I'm doing alright. Thanks for the water. I got up in the middle of the night, had water and aspirin and it seems to have done the trick."

"Great! So, you guys just finished a case?"

"Yep, Sam says hi by the way. We finished a Rugaru case, and then Bobby needed some help so we came through this way."

"Always happy to have you, even when you're a little drunk."

"Yea, sorry about that. I had to kill time, and well...you know.."

"You know I don't mind. So, how about a movie today once we're up and ready? There's a few classics showing at the cheap theater and we can get the matinee price. Maybe some crappy popcorn and candy, and then after pizza?"

"[Y/N], I swear it's like you can read my mind." He smiled that devilish grin at you and a flash of him half naked flooded your mind. What the hell were you supposed to do with what you saw the night before? Nothing you supposed, at least that's all you had the guts to do about it. There was absolutely no way you were going to make a move on Dean after all. The rejection would kill you.

The rest of the day found the two of you hanging out like the buddies you had become. When Dean was in town, it was like being a teenager again. He would agree to do anything with you and you were happy to oblige. You always had something in the back of your mind for the next time he came.

That night proved uneventful, and by the next morning, you knew he was heading out. Breakfast that morning seemed quiet, almost like he was going to miss you. You weren't sure what was going through his head, but you missed him too. It was just something neither of you said to the other. There was no heavy emotion mixed into any of the conversations you had. It was just fun hanging out and then a little small talk. Sure you would talk about your past or the cool things you were up to, but never anything beyond that. Even when the thoughts of Dean maybe never coming back invaded your brain, you still couldn't bring it up. There was no reason to sour this incredible thing you had whatever it was.

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

Dean visited another two times in the next four months, and no more awkward situations happened. It was when he left the second time that you had finally convinced yourself that it was either a dream of yours or a weird fluke that you caught him doing that. Maybe he had met a girl with the same name on some trip, and you had stumbled on him fantasizing about her. Either way, it was a dead issue.

The next six months were long. Dean hadn't texted or called and you started to wonder if that was it. He had been a temporary friend in your world, and now you just had to get past him and hope he was okay. You never messaged him unprompted. He had told you that you shouldn't just in case someone got his phone. He didn't want you to be exposed to anyone or anything in his world. That way, you wouldn't be in danger. So, now you were just left to pine after someone that had never really wanted you anyway. That dreamy mystery that was Dean wasn't coming back.

It was a quiet Friday night after that realization that found you in your living room curled up on the couch eating ice cream and watching some scary movie when another knock came. It had been a long day at work and you weren't expecting anyone, although on occasion one of your friends or a neighbor would stop by to chat. The one person you didn't expect to see was the man standing on the other side of the door.

"Hey beautiful. How are you?" Dean's smile took your breath away, and you let your excitement get the better of you. You pulled him inside and wrapped your arms up around his neck. A quick movement and your lips met his without even thinking.

You pulled back instantly at the touch, fearing the worst and looked at him.

"I'm so sorry. I didn't mean to Dean. I was just so worried that you were gone and seeing you... Well, I'm sorry I was just relieved." You blushed as you backed up and watched him carefully. He turned pushing the door shut and throwing your deadbolt without a word.

"Are you sorry like you didn't ever want to kiss me or are you sorry that you did it then?" His question had you on edge and you wondered how he had formed such a coherent thought when you could hear the slur in his voice that signaled he was a little drunk.

"Um...the second one." He approached you and you backed up. Dean lowered his head a little, staring at you like you were prey for a second. You weren't sure if he was angry or drunk or what, but that was a look you hadn't seen from him before.

"I've been waiting for almost two years for you to kiss me, so don't apologize for doing it now." He stalked towards you and you backed up until you hit the wall at the edge of your kitchen. He continued until he was only a few inches from you and tilted your head up with two fingers beneath your chin. "Baby...do you want me to kiss you?" His words were slow and thick as he spoke, eliciting a carnal response from your body. Moisture filled your panties as you looked from his eyes to his lips. Goosebumps erupted across your skin as time stood still.

"Yes." A single word and Dean leaned in claiming your mouth. The heat and softness of his lips surprised you as you let the taste of whiskey and beer slide into your mouth with his tongue. He moaned softly as he kissed you deeper and deeper, pausing only to switch sides with his head.

You were a mess by the time he moved to your jaw; only able to think about all the times you had dreamed of this moment, hoping desperately that Dean would claim you as his. His tongue slid haphazardly over your throat and you pushed your hands under the shoulders of his jacket. He got the hint, quickly shedding it without even stopping his onslaught on your neck.

His body pinned you against the wall with his hips flush to you holding you steady. When your fingers threaded into his hair, he groaned. Nails across his scalp had him leaning down to seize your ass in his fingers pulling you from the floor. You wrapped your legs around him and he carried you to the bedroom. No sooner did he throw you on your bed than he was stripping off his clothes like a mad man. You were transfixed, taking in each inch of freshly exposed skin and drooling as you watched. When he was down to only his boxers, he flung himself at you reconnecting with your mouth even as you tried to get your bearings.

He had you pinned and was soon making his way down your skin. When he reached your neck, he let his hands move downward taking the hem of your t-shirt and pulling it up over your head exposing your flesh. His lips seized on a nipple and his tongue flicked over it lightly. You were moaning before long and when he started to head downward you held your breath. Your imperfections seemed to not matter to him, and you felt like a goddess as Dean peeled your shorts and panties from your body.

He laid a few kisses along your hips before rejoining your mouth. His fingers brushed along your already wet core and you groaned at his touch. Your hand moved down his stomach taking in the muscles that you had only looked at before.

"Dean, please..." You needed him now. It was wonderful to have his fingers on you and maybe someday you would get past your insecurities and want his mouth on your pussy as well. Today, though, all you wanted was to feel Dean inside of you. Your pussy ached for him.

"What baby? Tell me what you want." He cooed the words out, the whiskey scent ghosting from his lips still as he looked down at you.

"You...please...I want you inside me." You whispered it staring into his eyes with intention.

"Condom?" A single question had you reaching the nightstand by your head and pulling it open. You produced a foil packet and then stopped to take a quick look to assure it wasn't expired. You didn't really use them very often to be honest.

When you turned back, Dean had his boxers off and was eyeing you eagerly.

"You want to do the honors or shall I?" His smile was wide as he spoke, and you could think of nothing more that you wanted in the world than to put a condom on this god of a man so he could take you.

You didn't respond, just tore open the packet with your teeth and reached down. At first, you thought you were being stupid, but then you realized why you were having trouble. Dean wasn't hard, not even a little. The proud cock you saw cum so many months ago hung limp against his leg. You would say nothing, you decided, and instead assumed he had that much control. Your fingers wrapped around his soft shaft and you moved up and down. He hummed a little, but still nothing.

"You need help beautiful?" He asked the question and you looked up into his eyes. Your mind reeled and all your anxiety flooded in.

"Dean, I can't because...well you're not hard enough." There you said it, but the words made your heart sink.

"What?" He looked a little puzzled and then glanced downward. A shock registered on his face. "Shit, um...give me second." His own hand came down and he gave his soft shaft a few pumps. "I'm sorry, this...shit...this never happens."

"It's okay. I understand." In your mind, his body had responded the way he would have sober. He didn't want you, not really. All that excitement and everything was a show, a response to the pity he felt for you and nothing more. Your heart sank and your self-esteem sank even faster. The great Dean Winchester was trying to force himself to get excited by you.

"Hang on maybe if I..." He reached out his hand and latched on to your breast kneading it gently. A wave of disgust flew through you and you pushed him away. You stood up from the bed searching for your t-shirt and your shorts.

You didn't speak as you started to put your clothes on. Dean lay there for a second as if stunned.