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Laurel and Tommy watched Oliver walk out with Maggie, and then looked at each other. “Under different circumstances I’d say he’s doing good in the father figure department.” Tommy told her. "I'm gonna go check on Clay, though." He kissed her cheek. 

She sighed once she was alone and shook her head. She just hoped things worked out for everyone. As long as you were supported. 

Blinking, you rolled over to look at the clock. It was nearly four in the morning, so you decided to go check on the kids. You peeked in to where Maggie slept and your heart melted. Oliver was on his back, and Maggie was in his arms. The two of them made you feel warm inside. Moving towards them, you gently covered them up. 

You smiled at them once more before going to check on Clay. He was sprawled out, making you chuckle. He always had the most comfortable positions. You kissed his cheek and went to get yourself a glass of water. The quiet was nice. It gave you a moment to think about things. You'd hoped one day for a handful of kids, but that had gone out the window years ago. And this certainly wasn't how you'd hoped it would happen. You also couldn’t help but be sad that you didn’t have a husband to share the pregnancy with. You wouldn’t have someone to help name them, to feel them kicking, to help pick out baby furniture, or cut the cord. You wiped your eyes at that thought. Shaking your head, you knew you had to just accept that this was how things were. You’d be okay. You had to be. The most important people in your life depended on you.

You sat on the table and just focused on your breathing while you held your glass. “Can’t sleep?” Came Oliver’s voice, making you jump.

You held a hand on your chest before shaking your head. “Not anymore after I woke up.” You shrugged. “Figured I’d check on the kids, and get some water.” You sighed. “You seemed comfortable.” You chuckled lightly.

He smiled shyly. “Didn’t mean to fall asleep with her. One second I was checking for monsters and then I was out.” He explained. “I tried to tell her they won’t go after Arrow’s biggest fan, but she wasn’t buying it.”

You smirked. “She’s stubborn.” You agreed. “And once she attaches herself to someone, that’s it. I’m surprised she didn’t curl up with Laurel.”

“I am honored.” Oliver grinned and sat beside you. “She said she ‘loves’ Laurel, but she’s not the same as me. Whatever that means.” He chuckled. 

You hummed. “Could mean anything. Maybe you’re more squishy.” You teased. “I don’t know.” You sipped your water. 

He laughed. “I see how it is.” He shook his head. “Either way I’m glad I could be here for her. For all of you.” He said easily. He let them sit in silence, neither of you really finding it uncomfortable. 

You leaned into him after a while, closing your eyes. He shifted to put his arm around you. You hummed and nuzzled to him. “Yup. I see why Maggie likes it.” You whispered. “You’re warm.” You told him.

“Well, like Maggie, I don’t mind cuddling until you fall asleep.” He offered. “If you need it.” He said honestly. “Although, I probably won’t fall asleep. I’m wide awake now.” He chuckled.

You bit your lip. “Just laying there would be nice. If you’re comfortable.” You were kinda glad he wouldn’t fall asleep. The last thing you needed was the kids finding you asleep together. Maggie would likely get the wrong idea.

“I wouldn’t mind at all.” He promised, standing. “Let’s try.” He offered his hand. You took it, setting your drink on the table. “How’re you feeling?” He asked as the two of you walked towards your room.

“A bit down.” You said honestly. “Physically just tired.” You shrugged a shoulder. “But, I need to get used to that.” You’d be napping whenever you could. You’d been really tired when you were pregnant with Maggie, mostly because you were also entertaining a four year old. Now you’d be working, and taking care of two kids.

He nodded. “Let me know when you need a work break.” He laid down first and opened his arms. 

You shyly got comfortable and shook your head. “I don’t want to stop working until I have to.” 

“Okay.” He smiled and kissed your head. “Try to get some sleep. I’m sure the kids will be up and ready to play in no time.” He said softly.

You nodded and closed your eyes, listening to his heart beat. It was oddly soothing, and your breathing soon evened out.

Oliver felt some panic as he knew he was catching feelings. He knew he’d have to do something to combat this, or he’d be screwed. It was only Thursday, so he’d go out to have some fun to distract himself the next night. Wasn’t like this was even possible. This was something that would never, ever happen. Even he fell for you, it couldn’t. He stayed staring at the ceiling as a thought and knew he had to distant himself just slightly. 

When your alarm went off, you rolled over to your back. Oliver was gone, but you weren’t surprised. That wasn’t something you needed to get used to. It wasn’t the time. You rushed to take a quick shower before getting the kids ready for the day. Clay needed to get to school, and Maggie needed to get to daycare. 

Laurel had begun breakfast for the kids, smiling to herself as she felt this was something she could get used to. When you came out, Maggie was in your arms, and Clay was yawning behind you. She looked up and chuckled.  “Morning. Coffee is running and this should be done in a few.” She told you. “How’d you sleep?” She hoped to start your morning off on a good note.

“Actually, not too bad. I think I was so exhausted.” You sat Maggie down. "Woke up once, but it didn't take long to get back to sleep."

“Glad to hear it.” She smiled. "What time did Oliver leave?" 

“Uh, probably 6 maybe?” You blushed. “He was gone by the time I woke up, though, so I can’t be sure. Looked like Maggie was comfy cuddling him last night.” You tapped your daughter’s nose.

“He’s the bestest cuddle person!” She announced. “And he made sure there were noooooo monsters!” She smiled up at you. 

You grinned. “He is a good person to catch monsters.” You agreed. “But he can’t be here all the time to check, remember that. Okay?” 

She pouted. “Why?” She asked, not liking that. 

“Because he doesn’t live here, stupid.” Clay yawned.

Maggie frowned at him. “I not stupid! You are!” She shot back. “And so mean!” She pouted. 

“Guys, stop.” You sighed. “Oliver doesn’t live here, and I can check under your bed for monsters. Clay, you’re sister isn’t stupid.”  

Clay rolled his eyes and laid his head on the table. 

“Why can’t he live here?” Maggie asked. “It’d be so much fun.” She looked up at you innocently. Laurel thought it was adorable, and simply plated breakfast. “He could sleep in my room! Or yours, mommy!” She grinned.

You ran a hand through her hair. “Because Oliver has his own house with his own family.” You told her. “Okay?” You told her. “He has his own life.” 

That night, Oliver smiled as he walked into the club, his eyes wandering. He eyed people as they passed him, looking for someone to catch his eye. Anything that would distract him for the night, and hopefully start him pushing down these feelings. 

He saw a flash of skin and immediately followed onto the dance floor. He smiled at her as she began to dance with him. He inhaled the scent of her shampoo and shook his head as it reminded him of you. His jaw clenched for just a moment. He told himself to pull himself together and pulled the girl closer. He enjoyed how her body reacted to his. It would be a good night. 

Tommy watched from where he was standing at the bar, sipping on something. He was leaning on his elbow, letting out a sigh. He was glad that he didn’t think you were into Oliver with how his friend was acting. He really hoped your feelings stayed that way. He didn’t want you more hurt than you already were. Downing the last of his drink, he set his glass down and went to mingle. 

Oliver woke the next morning, hugging the person he was holding. Half asleep, he groaned. Forcing his eyes open, he looked down at the brunette in his arms. Hearing his phone, he reached over and grabbed it. It was a text from Laurel. 

We’re all going to the county fair. You want in? We leave in an hour. 

He tapped his chest. He could make it. Yeah, okay. I’ll go. He replied quickly. 

You had caved when Laurel mentioned the fair, and both kids begged to go. Neither of them had ever been before, and you knew that wasn’t fair. She didn’t mention that she’d invited Oliver, however. So, the moment Maggie saw him, she squealed and ran to him. “Oliver! Oliver!” She lifted her arms and nearly launched herself into his hold. He chuckled and lifted her, swallowing. “I didn’t know you were coming.” She said excitedly.

“Surprise.” Oliver hugged her and smiled over at you. You smiled back and he looked back to Maggie. “Excited for the rides?” He asked.

“Yes!” She cheered. “And cottonandy.” She combined the words. “It’s yummy!” She smiled.

“Then we gotta get the princess some cotton candy.” He grinned.

Going back to real life was interesting. At his parents’ the pair of you had been in your own little bubble. Now it was back to the real world. The first day back you mainly caught up on housework before sitting down to get some writing done. That trip had given you a few ideas that you were very excited to get started. There was the small town second chance romance with the football coach (starring your favorite character from a 90s rom-com), there was the new woman in town with the town grump (starring your favorite side character from another show), and then a rockstar stranded in town because his bike broke down (starring your favorite show’s character). 

Typing away, you quickly lost track of time. You knocked out the small town second chance in one go before starting the town grump one. You’d get what you could written before rereading and editing. Then you’d slowly get them posted. Hopefully your few readers liked them. 

Hearing your phone, you glanced over to see a text from Dean. You don’t have to reply, but I thought I’d say goodnight :) It was then you noticed the time. You’d been writing for hours. 

It’s later than I thought!! I’ve been so caught up in writing I didn’t notice. And goodnight to you, too :) Sleep well. Once you hit send you finished up the paragraph you were on and closed out of the writing program. You knew you needed to get to bed. 

Maybe one day I’ll get to read your work. 

Did you want him to? While you didn’t think that he was judgemental, it was still a scary thought. Would it change how he viewed you? Chewing on your lip, you told him that you used tumblr, and your username, then locked your phone, plugged it in, and left the room. 

Dean was surprised when you replied the first time, then even more surprised when you told him where to read your writing! He had planned to tell you goodnight, crawl into bed, and get some sleep. Now he was wide awake and needed to read at least a couple things of yours. 

He scrolled a bit, intrigued about the variety of things you wrote about. You had things tagged ‘tooth rotting fluff’, ‘angst’, ‘HEA’ (he had to look that one up), ‘nsfw’ (with various tagged details), and a sprinkling of others. Opting to start light he chose one labeled ‘HEA’. Once he was comfortable he started to read. Instantly, he was hooked. 

After he had read a few things he made an account. He wanted to hype his girl up! He went back to what he read, liked them, reblogged them (with comments), and hoped that this was something that would make you happy. He also started a list of ideas for the two of you (that he planned on adding to). Before he knew it he’d read a quarter of your work. 

The next morning you sat at your computer to drink your coffee and check your tumblr. You froze with your coffee cup to your mouth when you saw Dean had not only made an account, but he reblogged a ton of stuff- with comments. You finally took a sip of your coffee as you scrolled to the first thing that he reblogged to read the comment. 

I was hooked by the second paragraph! My girl is so talented. Off to binge read instead of sleeping. 

You giggled at that, moving on to the next one. 

Uh, he was such an idiot for a bit there. How could he not see how that was bothering her? Glad he got his head out of his ass! 

“Me, too.” You agreed with a chuckle. Picturing him reading your work and getting into it like he did with your period romances was a fun picture. 

After you’d read all his comments, and reblogging with comments thanking him, you grabbed your phone to text him. Good morning. I can’t believe you read that much of my work! Thank you so much 😀 

With that, you started your day on a very very good note. You couldn’t remember the last time you started your day feeling that happy. 

You had no idea that every night before bed Dean read another one of your stories, took notes, and only sometimes reblogged and commented on them. He didn’t want to give himself away. 

When he knocked on your door that Friday evening you were surprised. As far as you knew, the two of you didn’t have plans. He’d had a busy week and he said he just wanted a relaxing night in. “Dean?” You smiled as he stood there with a bouquet that held a movie nestled in the middle. The flowers matched the coloring of the movie. “I thought you wanted to relax?” Taking the flowers, you lifted the movie. “The Greatest Showman?” 

He kissed your cheek as he stepped in. “Yeah, one of your characters said she loved it, but I had never heard of it.” He shrugged. “I looked it up and it looked fun. If you own it I can keep it at my place.” This way you didn’t have two copies hanging around. “And I never said where I want to relax.” 

“This is true.” You chuckled. “I haven’t made dinner yet, want me to make something really quick?” 

“Nope. Dinner will be here in about ten minutes. I got you Pad Thai from one place, then cheese rangoons from another.” Dean hadn’t talked to you above movie night that week because he wanted it to be a well thought out surprise date. And judging by the look on your face? He’d be doing this at least monthly. 

Your heart skipped a beat. “Why, thank you.” There was a light tint to your cheeks. “Let me go put these in some water and get us drinks.” You motioned to the kitchen before shutting the door. “I have some of your favorite beer in the fridge, or I have soda.” 

Dean got a silly smile on his face hearing that you now had his favorite beer on hand. “Beers good, sweetheart.” He told you. His eyes followed you as you moved around your kitchen. Then you stood in one spot to put the flowers carefully in the vase like they were the most precious flowers in the world. “Where do you plan to put them?” 

Looking over at him, you lifted the vase. “The coffee table for now. So we can admire them. Then after that I'll move them to the dining room table.” 

“Perfect.” 

Walking in the motel room, you let out a small breath. Sam was asleep in one bed, and you assumed that Dean went home with someone. As quietly as you could, you moved to your bag and pulled out a pair of sleep shorts. Glancing at Sam, you chuckled lightly. He looked like a kid when he slept.

Your hands were on your back as you paced your hospital room. Sam was sitting in the chair in the corner, not really able to do anything. Dean was on his way from work, which meant that he’d be a greasy mess. You just hoped that he didn’t get sent home to shower. “I’m never having another kid.” You groaned.

“I doubt Dean is gonna let another male that isn’t related to you near you after this.” Sam joked. “Heck, not just you but Cheyenne too.”

You glared at him. “She is never dating.” Sam laughed. “Oh you think I’m joking? I will never want her to go through this. This isn’t even the worst that it gets!”

Sam moved to stand in front of you, stopping your pacing. “Look I know you are scared but everything is gonna be fine.” You nodded. “I’m here, Dean’ll be here soon. Everything is gonna be okay.”

You looked at Sam, you knew he was just as nervous as you were but you were grateful to him. You were afraid of so much at the moment, labour, the pain, being a mother. What would happen over the next few hours would change your entire life. How could you not be scared?

Leaning your head on his chest, you half whined, half groaned. “At least I’ll be able to see my feet again.” You joked.

He laughed, nodding. “And get up without it being a workout.” Sam teased.

“Shut up.” You let out a partial chuckle.

Looking down at the test, you teared up. Pregnant. Fucking pregnant at 19. Your back hit the bathroom door and you slid to the floor. Pulling your knees up to your chest, you sobbed. The boys would be furious, and for just a split second you were thankful John wasn’t there.

You weren’t sure how long you sat there before you stretched your legs out in front of you and looked at the test again. “Why me?” You breathed, throwing the test across the room. As if it would help you any. You had a lot of thinking to do. And fast.

Once Cheyenne was born, and everything was cleaned up, Dean came back in. The man could deal with demons, monsters, and stitching himself up. Holding your hand during birth turned out to be another story entirely. At one point the nurse asked if he felt faint. “Hey, sweetheart.” He held up a small bear.

“Hey Dean.” You smiled up at him sleepily. “You wanna meet your niece?”

Dean moved closer, almost tiptoeing as to not disturb the quiet infant. “Look how small she is.” He sat on the edge of the hospital bed, leaning over slightly to see the beautiful baby wrapped in your arms.

“She hasn’t put her down once.” Sam told Dean. “I keep telling her she is gonna have to put her down eventually.”

You stared down at Cheyenne. “I will put her down soon, I know I need to sleep. I just don’t wanna put her down. What if she needs something?”

Dean placed the small bear on the nightstand, then reached out his hands. “What if I hold her? You need sleep sis. You trust me right?”

You tore your eyes away from your daughter, turning your head to look at Dean. “Of course I trust you.” You looked back to Cheyenne. “Okay baby girl, your uncle Dean is gonna hold you for a little bit okay. Just while mommy gets some rest.” You slowly passed her into Dean’s waiting arms. “Never thought I’d see the big bad Dean Winchester holding a baby.” You teased.

He smiled at you. “Only for you.”

Lying on your back, your shirt was up to your ribs. You were staring down at your still mostly unchanged stomach, your hand right below your belly button. Taking a deep breath, you tried not to start crying again.

It had been just a few weeks since you told the boys about the baby. And it had been spent with them taking turns comforting you while you cried. You were terrified, your heart was aching for your unborn child, and your hormones weren’t helping one bit.

You teared up, sniffling. “Don’t worry, kiddo. You’ll always have me and your uncles.”

Yawning, Dean shuffled out into the living room. It had been a week since you’d come home, and every time Cheyenne woke up, he woke up. Even if you got her quickly. “Coffee.” He stretched.

“Sam’s on it.” You motioned to the kitchen. “He has to be to work in a couple hours, so I think that you may need a second pot.” You chuckled lightly. “I need to bring her to her one week checkup, so you can catch a nap.” At least that was something for him.

“You sure you gonna be okay. I could always skip the nap, come with?” Dean shrugged.

“No Dean, you go get some rest okay. It’s just gonna be a quick trip.” You shook your head playfully at him. “We will both be fine okay.”

“Well if you’re sure?” Sam walked through just at that moment with three mugs balancing on a tray.

“Sure about what?” Sam asked. “Quickly though, Dean coffee for you, coffee for me and some tea for Y/N.” You looked at him deadpanned. “Hahahaha not really, it’s coffee.”

“You’re hilarious Sam.” You quickly took the coffee, relishing in it’s taste. “Dean was just asking if I wanted him to come to the doctors with me and Cheyenne. I said that me and her will be fine.”

Sam looked at you. “Are you sure?”

“Not you too Sam. Look she will be fine, I will be fine. We will be fine.” You looked at them both exasperated. “Look I will call Dean when I get there, plus before we set off back home okay?”

The boys looked at each other. “Okay.” 

You were sitting at the bar sipping a glass of wine. You’d had no idea what to order and told the bartender you were waiting for your date, that it was a first date, and you weren’t a big drinker. She’d been sweet and poured you some Rose. Every time the door opened your eyes would dart over. Dean would be there any minute. Finally, there he was. You watched as his eyes scanned the dining room before they reached the bar and he saw you. His face lit up as he licked his lips, looking you up and down. It felt like he was devouring you and you loved it. 

“You look…wow.” He breathed once he was in front of you. You were you, that was for sure. But your dress was a little more form fitting (without being skin tight), you were wearing chunky heels, your hair looked beyond soft and he wanted to just run his hands through it (he made a note that if the two of you worked out he’d get your hair done just so he could mess it up after in the best way), your makeup was done, and you’d gotten a manicure. 

A light pink tint settled over your cheeks. Of course you’d been attracted to men before, but you had never felt attractive to men. Feeling like you were the only woman in the world to him was hotter than you could have guessed it would be. 

Dean offered you his hand. “Let’s go get this started, sweetheart.” His words said ‘tonight’, his tone said ‘forever’. If he had his way that’s exactly how it would work out. 

Smiling, you put your hand in his and slid off the stool. “Let’s.” 

The smile never left Dean’s face on that date. By the time he was driving back to his parents, he knew he was completely head over heels for you. “So, I know we’ve technically only had one date, but can I ask you to be my girl?” He glanced at you for a moment as the car sat at a red light. 

“I’d really like that.” You agreed. Dean had more than shown you that you could trust him and that he cared a lot about you. “I guess our movie nights are now date nights.” 

“I still want to take you out sometimes, too.” He let you know. “I don’t want to just have our dates at your apartment.” He didn’t want you thinking otherwise. 

“Good thing we live so close we can plan things for whenever we want.” You chuckled. “And…I decided to use my phone for more than work and emergencies. Lisa was showing me pictures and videos of her son. So many memories. I’d like for us to have those, too. And I’ll still prefer calling, but this way if we’re both really busy we can send a text.” 

Dean smiled softly at that. “As long as you don’t feel pressured to.” That was the last thing he wanted. 

You shook your head. “I’m not. It’s not like I’m going from one extreme to the other. I’ll still limit its use, but I won’t be as against it as I was.” 

“Then I’m glad. How about when we get back to my parents we take our first selfie together on your phone? And you can send it to me. Our first text will be us. And then I can make it my lockscreen.” 

It was like Disney wrote him or as if he had walked right off the pages of one of the fics you wrote. “I’d really like that.” Part of you wanted to ask if he wanted to sleep in the bed with you that night, but you were way too shy. Cuddling up with him all night sounded like the perfect way to finish the date. Was it too soon, though? Chewing on your lip, your eyes unfocused as your mind went a million miles an hour. 

“I can hear you thinking, sweetheart. Everything okay?” 

You’d already done so many things that scared you, so you decided to be brave again. “I was wondering if you’d like to sleep in the bed with me tonight instead of that cot thing.” Your cheeks were on fire. “I thought cuddling up together would be nice.” 

“Shit, sweetheart.” He beamed. “How’d you know I’m a cuddler?” Pulling into the driveway, he turned to look at you. “I am a very handsy boyfriend.” He winked. “But I will always ask permission first. You are the hottest woman in the world and I look forward to showing you that.” 

Your insecurities bubbled up a bit. “Even if I’m fat?” 

His eyes darkened at that. “You are a fucking babe.” His voice was low. “I have been imagining what’s under your cardigans for ages. And I know when I’m blessed enough to see that I will go nuts.” He watched as you shifted slightly in your seat, but not in an ‘I’m uncomfortable’ way. More like your imagination was going wild. “One day I’ll show you what I picture in the shower.” 

“Jesus.” You breathed, watching him slip out of the car and jog around to open your car door for you. 

“Hey, kids.” John glanced over at the two of you walked in. “How was your date? I can tell shopping went well.” He chuckled, noting the bags Dean was holding. 

You smiled. “Really well.” Which was putting it mildly. “How’s the game?” You motioned to the tv where he was watching some football. John and Mary were really easy to get comfortable around.

Dean leaned against the wall as you and John chatted. He could picture you there twenty years from now, his parents old and grey, kids running around, and he knew his dad was right. When you knew, you knew.

You were sitting at the bar sipping a glass of wine. You’d had no idea what to order and told the bartender you were waiting for your date, that it was a first date, and you weren’t a big drinker. She’d been sweet and poured you some Rose. Every time the door opened your eyes would dart over. Dean would be there any minute. Finally, there he was. You watched as his eyes scanned the dining room before they reached the bar and he saw you. His face lit up as he licked his lips, looking you up and down. It felt like he was devouring you and you loved it. 

“You look…wow.” He breathed once he was in front of you. You were you, that was for sure. But your dress was a little more form fitting (without being skin tight), you were wearing chunky heels, your hair looked beyond soft and he wanted to just run his hands through it (he made a note that if the two of you worked out he’d get your hair done just so he could mess it up after in the best way), your makeup was done, and you’d gotten a manicure. 

A light pink tint settled over your cheeks. Of course you’d been attracted to men before, but you had never felt attractive to men. Feeling like you were the only woman in the world to him was hotter than you could have guessed it would be. 

Dean offered you his hand. “Let’s go get this started, sweetheart.” His words said ‘tonight’, his tone said ‘forever’. If he had his way that’s exactly how it would work out. 

Smiling, you put your hand in his and slid off the stool. “Let’s.” 

The smile never left Dean’s face on that date. By the time he was driving back to his parents, he knew he was completely head over heels for you. “So, I know we’ve technically only had one date, but can I ask you to be my girl?” He glanced at you for a moment as the car sat at a red light. 

“I’d really like that.” You agreed. Dean had more than shown you that you could trust him and that he cared a lot about you. “I guess our movie nights are now date nights.” 

“I still want to take you out sometimes, too.” He let you know. “I don’t want to just have our dates at your apartment.” He didn’t want you thinking otherwise. 

“Good thing we live so close we can plan things for whenever we want.” You chuckled. “And…I decided to use my phone for more than work and emergencies. Lisa was showing me pictures and videos of her son. So many memories. I’d like for us to have those, too. And I’ll still prefer calling, but this way if we’re both really busy we can send a text.” 

Dean smiled softly at that. “As long as you don’t feel pressured to.” That was the last thing he wanted. 

You shook your head. “I’m not. It’s not like I’m going from one extreme to the other. I’ll still limit its use, but I won’t be as against it as I was.” 

“Then I’m glad. How about when we get back to my parents we take our first selfie together on your phone? And you can send it to me. Our first text will be us. And then I can make it my lockscreen.” 

It was like Disney wrote him or as if he had walked right off the pages of one of the fics you wrote. “I’d really like that.” Part of you wanted to ask if he wanted to sleep in the bed with you that night, but you were way too shy. Cuddling up with him all night sounded like the perfect way to finish the date. Was it too soon, though? Chewing on your lip, your eyes unfocused as your mind went a million miles an hour. 

“I can hear you thinking, sweetheart. Everything okay?” 

You’d already done so many things that scared you, so you decided to be brave again. “I was wondering if you’d like to sleep in the bed with me tonight instead of that cot thing.” Your cheeks were on fire. “I thought cuddling up together would be nice.” 

“Shit, sweetheart.” He beamed. “How’d you know I’m a cuddler?” Pulling into the driveway, he turned to look at you. “I am a very handsy boyfriend.” He winked. “But I will always ask permission first. You are the hottest woman in the world and I look forward to showing you that.” 

Your insecurities bubbled up a bit. “Even if I’m fat?” 

His eyes darkened at that. “You are a fucking babe.” His voice was low. “I have been imagining what’s under your cardigans for ages. And I know when I’m blessed enough to see that I will go nuts.” He watched as you shifted slightly in your seat, but not in an ‘I’m uncomfortable’ way. More like your imagination was going wild. “One day I’ll show you what I picture in the shower.” 

“Jesus.” You breathed, watching him slip out of the car and jog around to open your car door for you. 

“Hey, kids.” John glanced over at the two of you walked in. “How was your date? I can tell shopping went well.” He chuckled, noting the bags Dean was holding. 

You smiled. “Really well.” Which was putting it mildly. “How’s the game?” You motioned to the tv where he was watching some football. John and Mary were really easy to get comfortable around.

Dean leaned against the wall as you and John chatted. He could picture you there twenty years from now, his parents old and grey, kids running around, and he knew his dad was right. When you knew, you knew.

“Have sex with me-“

“Yeah, I- I heard you the first time, that’s not-“ Dean shakes his head, running a hand over his face. “It’s eight in the fuckin’ morning-“

“It’s eight fifteen.”

That earns you a flat look, and you smile innocently.

“That’s fifteen extra minutes, it matters-“

“Not for this. And- I ain’t even showered yet-“

Your nose wrinkles. “Why haven’t you showered?”

“I shower after coffee,” Dean mutters, turning his mug in his hands. “If I don’t, Sammy’s stinkin’ up the kitchen from his run.”

“Oh- Okay.” You clasp your hands behind your back, peering at his tight jaw, his mussed, soft-looking hair. “Is that… A yes?”

Dean’s eyes widen on yours. You’re worried he’s going to choke on the air this time. “Yes?”

“Are you going to have sex with me,” you clarify, and his mouth falls open.

“I- I’m- You’re-“ His throat bobs, and he starts to look around the room with a worried squint. “Are you fuckin’ with me?”

You frown. “Why would I be fucking with you?”

“’Cause, sweetheart, you can’t just-“ He lets out a sharp breath. “Is it Sam? Did he put you up to this? ‘Cause I told him- That kinda prank, it’s off the table-“

“What kind of prank?” You’re a little lost, and there’s shame starting to burn up your neck.

A prank. He thinks it’s a prank.

It’s not. You’re so serious it’s almost embarrassing. You wouldn’t have asked him if you weren’t. You’d almost talked yourself out of it, after spending too much time convincing yourself into it. Nights of tossing and turning in bed, an insatiable and aching heat between your legs and the sheets bunched around you in a mockery of a body. Weeks of watching the boys slip out of bars with women that seemed to fall into them like magnets while you spun around, alone on a barstool without any prospects.

Months, of watching Dean with a flush he never saw. An adoration written all over your face he didn’t seem capable of noticing. You’d tried to stomp it out. Your stupid, useless little crush. Dean was older. Seasoned and desirable in the way that made you wonder if he was even real sometimes. Out of your reach, tantalizing, and impossible to just forget about. 

You’d neglect your feelings in the hope they’d die, but he’d water them until they were in full bloom and overtaking your heart and mouth and head. He’d buy the snacks you like and let you chose the movie. He’d open doors and let his hand linger on your lower back, he’d smile at you in the dim light of the Impala and make you feel like the only person in the world, he’d call you when he was away on a separate hunt every single night, just to update you. He’d play wrestle you for the remote, and somehow never manage to wonder why he always won when he’d see you take down men closer to Sam’s size with barely a grunt of effort.

“Nice try, sweetheart,” he’d whisper in your ear, when he had you pinned on the floor beneath him, and you’d have to swallow down your moan.

He’d get up, turn on the TV, and leave you on the couch while he went to the bathroom. You’d sit with your knees to your chest and your breathing uneven, unable to focus on anything but the ghost of his body over yours. The heat of him, the way his arms had caged you in, his knee pressed far too close to your neglected core.

If Dean knew how you dreamed about him—how those moments followed you into bed, every single night—you’re so sure he’d never look at you again. He doesn’t see you like that, you’re sure. You’re the kid they took in, the annoying girl who’s got too much mouth on her and not enough experience, in every possible way.

You’ve never done sex. You sort of just missed the window, where it’s supposed to happen, and then it became too big a deal, then you met Dean and you were lost. What was the point of being with anyone else, when you had his shoulder bumping yours in the hallway. When you were so hopelessly in love with him, you think your heart might beat out of your chest like a cartoon every time you see him.

So you made a choice, a few weeks ago. A choice it took a lot of courage to work yourself up to following through on

You just need to have sex. With someone. Anyone. Preferably Dean. It just needs to be done and over with—one time, where he doesn’t know he’s taking your virginity, where he’s peacefully oblivious of your worship of his very existence—and then you can try to move on. Once you’ve had sex, it won’t be this big monster you shy away from anymore. It’ll just be another thing.

So you’re asking Dean. Outside of your alternate motivations, it’s a sound strategic call. You know about his prowess. He’s bragged to you about all his five-star reviews. And maybe that always made you gag over a toilet bowl after, but if it did, that’s none of his fucking business.

Maybe you’re not up to par with his usual partners, but you can do your makeup, or he can turn off the lights, or whatever else makes it easier for him. Anything that makes him touch you. You won’t even cry about it in front of him.

But he thinks it’s a prank. Why would he think it’s a prank.

“You know,” he says, watching you wearily. “Sammy gives you a tenner, you come and ask me for sex, everyone gets a good laugh at Dean. Good joke. Classy.”

You wrap your arms around your stomach, shrinking slightly into yourself. “It’s not a joke,” you mumble. “I- I was serious.”

“You were serious?”

He says it like it’s insane. You shrug, fixing your gaze on the floor. A joke. He thinks fucking you would be a joke.

“Sweetheart-“

“You don’t have to,” you take a step back, trying to sound casual. Like your heart isn’t being torn to ribbons.

You really hadn’t expected him to leap at the opportunity, but this is so close to cruel it hurts. Tears are threatening your eyes, and a lump is forming in your throat. Pathetic, a voice spits in your head. Why the fuck would he ever want to fuck you.

“Wait, just- Hold on-“

You look up, faster than you want to admit. Dean staring at you with pale face and slack jaw, throat working like he’s swallowing his own words every second. You wait, because you’re a fucking useless idiot. Bouncing nervously on your feet—they’re smarter than the rest of you, they want to run—and trying not to melt under his gaze.

“You’re actually askin’ me to fuck you?” He rasps, and you nod.

It’s the tiniest motion of your head. Dean shifts in his seat, staring at you with wide, dark eyes.

“Why?”

“Why?” You frown, saying the first, easiest, least embarrassing reason that pops into your head. “Because- You- You’re good at it?”

“I’m good at it,” Dean repeats. “You wanna fuck me ‘cause you think I’d be good at it?”

You wish he’d stop saying fuck like that. With a harsh ending and low drawl. “I don’t think,” you offer. “You’re the one who said you would be.”

Dean’s lips twitch, but he doesn’t look amused. “I could be lying, sweetheart.”

“I don’t think you are.”

He stares at you. His eyes flick up to the ceiling—maybe he still thinks he’s on a prank show—and he lets out a sharp, slow breath from his nose.

Then he shakes his head, and you feel the echo of your heart as it howls in pain.

“No,” he mutters. “I ain’t- Doin’ that. Not just ‘cause you- No.”

You blink at him, the world blurring a little. You stumble back, and Dean says your name, moving to his feet. You shake your head, moving back another step. Your eyes are stinging with tears, but that’s not his problem. He’s allowed to reject you. You’re also allowed to cry about it.

“Sweetheart-“

“It’s fine.” Your voice is too high. Too wobbly. “It’s- That’s okay.”

“No, just- Fuck-“ He rubs his jaw. “Listen to me, alright-“

“You don’t have to explain,” you shrug weakly. “It’s okay.”

Dean gives you a disbelieving look, but you move further back before he can try to make you feel better about the rejection. It’s not going to help.

“I’ll just-“ You look over your shoulder. To the door, just one more step back.

Dean says your name again. When you look back, he’s reaching to you, trying to beckon you back into the kitchen. You smile, tight and watery.

“Thank you for your consideration.” You say, because you’re a fucking idiot. Dean certainly looks at you like you’re one.

You flee the kitchen. He calls your name again, but this time you don’t look back.

Rejection is fine. You’re fine. You’re so fine, you lock yourself in your room for the rest of the day and eat so much ice cream your stomach hurts. Because it’s fun. It’s fun to cry over something you never even had.

At least you anticipated this. You have a very solid plan B.

If Dean won’t sleep with you, you’re going to find someone who will. You’re going to get it over with. This week.

You’re learning something about yourself.

You are not good at flirting.

The first thing you try is the bars. Sam and Dean slide into a booth, and you go to get the drinks. A guy makes eyes at you, and you smile sweetly in return. When you bring the drinks back, you set the beers down in front of the boys and turn back on your heels to give the bar-guy a shot.

Dean says your name, and you freeze. You always do that for him. It’s a habit you don’t think you’re able to break.

“Where’re you going?” He frowns at you, one arm slung around the back of the seat. Around where you’d usually sit.

“Bar,” you say lamely, and the lines on his face deepen.

“Why, you forget something?”

“No.”

“Then what-“

Dean cuts himself off, his gaze flicking over your shoulder. To the bar. To the man, waiting for you with a smirk, because you promised you’d be back.

Dean grunts your name, low and rough, and if he asked you to stay, you don’t think you’d be able to tell him no.

Things have been strange, since the kitchen. Neither of you have brought it up, and Dean hasn’t stopped treating you the way he always has, but there’s something charged beneath it. A live wire that frays and crackles, every time your fingers brush or your eyes meet. You’ve caught him staring at you with an open mouth a few times. Last week he tried to talk to you, alone in the Impala while Sam got snacks from a gas station. You announced that you had to shit, and scrambled out of the car.

You don’t want to talk about it, and Dean has no right to make you. He’s not the one who got his heart broken. He’s not the one who sort of wants to cry, whenever your eyes meet.

He certainly has no right to glare at you, when he puts together what you’re doing. He said he wasn’t going to sleep with you, and you’re a grown woman. You can, if you so please, have casual sex with a stranger. It is your right.

“You can’t be for real, sweetheart-“

“Dean.” Sam stares at his own beer, looking like he wants to vanish into the floor, and Dean scowls.

“C’mon, Sammy- Tell her she’s being crazy-“

“Crazy?” You snap, and Dean leans back in surprise. “You fuck around all the time, how is it crazy that I’d do the same thing?”

“It’s not- You just- You don’t-“ He swallows. “You don’t do this-“

“I do now.”

“Sweetheart, just- Sit down-“

You flip him off, and march back to the bar before he can ask with a little more conviction. You just need to break out of his orbit. To force yourself to realize that there are plenty of other men, and not having Dean isn’t the end of the universe.

Unfortunately, you sort of just keep proving the opposite.

“What’s a pretty little thing doin’ in a place like this?” The first guy at the bar asks, and you fumble.

You have no idea. You giggle nervously and spin in your chair, speaking words you can’t really hear. He seems into it—no matter how pathetic you must be coming off—until his fingers brush your arm, and you flinch back because his skin is cold. It sends a shiver up your spine that’s not the hot rush of Dean’s touch, but the sliver of a snake.

You go home alone that night, and you don’t look Dean in the eyes. He tries to talk to you, before you retreat to your room. You ignore him, because that’s the only way this is going to work. 

But you try again and again and again, and you never get anywhere. They always touch you, and it all falls apart. You look at them too long, and you can’t manage to squeeze them into a Dean shaped hole in your heart, and there’s no way forward. You try dating apps. That goes worse. Every dick pic you get sent just makes you wonder if sex is even something you want. They’re all worm-shaped and ugly. At least dildos come in nice colors. Maybe you should just buy a dildo.

No. You’ll just pretend it’s Dean all the time, and that’s the opposite of what you’re supposed to be doing here.

So you keep trying. And you keep failing. And Dean’s been looking at you weird—brow pinched and jaw set, every single night—and you’re getting desperate and fuck it.

“Sam.”

Sam hums, not looking up from his book. You clear your throat, leaning further over the table.

“Sam.”

“I’m listening, what’s-“

“Have sex with me.”

Sam, to his credit, doesn’t choke. He just goes very, very still, and looks up at you with an expression close to horror. He says your name slowly, and you shake your head, holding up a single hand.

“Just- Listen-“

“No?” Sam gapes at you. “I’m not- I’m not going to listen to that- Jesus Christ-“

“Come on, we could turn off the lights, and- I wouldn’t make it weird-“

“It’s already weird-“

“You’d be doing me a favor-“

“I’d be making a death wish!” Sam’s voice drops to a hiss. “Dean would fucking kill me.”

 You roll your eyes. “Then don’t tell him, dumbass.”

“No, I- I’m not doing that.” Sam shakes his head, like he’s trying to jolt the image free. “To you. Or him.”

“To him?” You narrow your eyes. “I- What the fuck would this do to Dean?”

Sam gives you a puppy-eyed, hopeless look. “I… Can’t say.”

“Sam Winchester-“

“Why are you asking me?” Sam whines. “I’m not- You’re not even into me-“

“Exactly, there would be no strings attached-“

“That’s not healthy-“

“Fuck off, like you don’t have casual sex-“

“I mean, I do, but I’m not-“ Sam cuts himself off, sighing dramatically. “Just- Why would you even want to have sex with me?”

You flush, but shrug. It’s just Sam. It’s easier to tell him than Dean. “I want to get it over with.”

“Get it over with?” Sam echoes. “It- You mean sex?”

You nod, and Sam blinks.

“Are you a virgin?”

“Maybe.”

“You- You’re-“

“Don’t be an asshole-“

“No, I’m not- I mean- It’s fine. It doesn’t matter. It actually-“ Sam frowns at the air. “It makes sense, I guess.”

That makes you scowl. “It makes sense?”

Sam shrugs, giving you an apologetic smile, and you can’t even think of an argument. You sigh, your shoulders slumping, and Sam clears his throat.

“You know I’m not going to sleep with you, right?”

“Yeah.” You sigh, and he nods slowly.

“Does Dean-“

“No.” You point a stern finger at him, and Sam raises his hands in surrender.

“I think you should-“

“Sam. I’ll cut your balls off.”

“I- Okay.”

You give him one last glare, and go to leave. But before you can go, the question scratches up your throat. You turn around, hands tucked behind your back, and speak softly. “Would you?”

Sam blinks. “What?”

“If you didn’t- Know me,” you mumble. “If we weren’t like- Friends. And you just met me, and I asked you- Would you?”

Sam snorts, and you scowl.

“I’m serious-“

“Yeah, I know you are.” Sam’s lips twitch. “It’s just- Yeah. I would. Of course I would.”

You stand a little taller. “Really?”

“Yeah, I mean- You know you’re attractive, right? If you just didn’t, like, annoy me. I’d be in.”

“I do not annoy you-“

“You’re annoying me right now.”

You laugh despite yourself. Sam smiles, his voice dropping to something gentler.

“Anyone would be lucky to have you,” he says your name slowly. “I just- Don’t want to be lucky.”

You huff in amusement—if Sam isn’t lying, aversion to luck is a family trait—but dip your head. “Thanks. I think.”

“You’re welcome. And-“ Sam pauses, looking you up and down with a strange expression. “I’m sure the whole- Thing will work out for you. There are… People. I think you’re going to figure it out.”

“You need to sleep with her.”

Dean needed to stop drinking coffee when people walked into the kitchen. This was the second shirt he’d ruined in as many months, and it was because everyone kept saying crazy fucking shit.

“Sammy, what the fuck-“

Sam said your name, and Dean’s hands fisted on the table.

Again. Son of a bitch, he was about to go through this again. The first time had been bad enough. You’d looked at him with glossy, hopeful eyes, practically begged for him to fuck you, and Dean had wondered if he’d died in his sleep last night and been dragged back to hell. Forced to experience some new kind of torture Crowley was developing, where everything he’d ever wanted was just a stretch away from his fingertips, and he wasn’t allowed to take it.

He had to be the noble one here. The wise, old asshole who didn’t take advantage of you. Taking you up on that offer would be one of the worst things he’d ever done. It would be selfish, and cruel, and a worse fate than anything else. To get what he wanted, for one night, then never fucking have it again. To get hooked—because he would, he fucking knew he’d never be able to kiss and touch you once then go back to just living—and turn into an addict willing to do anything to get another hit.

Dean would’ve turned into a bigger creep than he already was. Instead of stares and long, shameful showers with his cock in his hand and your name on his lips, he’d stuff your panties in his pocket and press them to his nose while he fucked himself raw. He’d get possessive, he’d snarl at anyone else who got to close, he’d fall to his knees and beg you to stay if you ever decided you had enough of him.

And he knew that last thing was going to happen eventually. You had a whole life ahead of you, and he was stuck here. In this dim bunker with blood on his hands and under his feet and staining his past and future all at once. He swam in a river of it. In front of him, behind him, washing over him all the time, there was just fucking blood. You deserved better than that. Better than Dean. You deserved the fucking world.

So he’d told you no, and you’d looked at him like a wet fucking kitten he’d kicked into the rain, but it had been for your own good. You’d get over it. Dean was the one who had to watch you flirt with douchebags at the bar. Who couldn’t get in another bed anymore, because he kept getting kicked out for moaning your name.

He was the one who was rooted here forever. You’d find something softer. Something good.  He’d accepted that, with a lot of beer pushing it down. You’d find something better, and that was what he wanted.

Sammy knew all that. Dean had gotten drunk once and confessed his stupid, undying feelings, then sworn Sam to secrecy in the morning. He’d kept his word, only shooting Dean sad looks whenever you went off to flirt and smirking whenever Dean called you on a hunt.

But now he was asking Dean to sleep with you. Like he’d lost his damn mind.

“No,” he grunted, and Sam rolled his eyes.

“Look, Dean, I get that you’re being cool and righteous and whatever-“

“I’m not fuckin’ her, Sammy- I shouldn’t.” He shot Sam a glare. “You know why I shouldn’t.“

“Yeah, well, I think your why is pretty stupid.” Sam said flatly. “You’ve never even asked her if she’d be- You know. Open to it-“

“I know she’d be open to it,” Dean scowled at his coffee. “But that’s- I ain’t doing it, Sammy. Never.” Not like that.

Sam was silent for a moment. When Dean looked up, he was staring at him with wide eyes. “She asked you first, didn’t she.”

Dean frowned. “What’d you mean, asked me first-“

“To take her virginity.”

He hadn’t taken a sip of coffee again. This time, he managed to choke on nothing at all. “To- What?”

Sam leaned back slightly. “Did she not ask you to sleep with her?”

“No, she did, I just didn’t fuckin’- She’s a virgin?”

“I guess,” Sam shrugged. “You know that’s not a big deal, right?”

Dean grunted. His head was spinning. Of course it wasn’t a big deal, he didn’t care. He’d wanted you before, he wanted you now, that wasn’t the fucking issue.

But you’d asked him.

You’d asked him to fuck you. You’d wanted him to- Do it. Take it. Pop it, whatever. You’d chosen Dean, to be the guy, and he’d told you no, and then you’d started flirting around with other people, and you could’ve ended up with someone dangerous, someone who took advantage of you, who thought your inexperience was hot for all the wrong reasons and hurt you and-

Dean paused. He looked at Sam. Sam blinked, and Dean’s eyes narrowed.

“How the fuck do you know that.”

Sam swallowed, taking a small step back. “Uh…”

“Sam-“

“She might’ve… Asked me.”

“She what-“

“I said no!” Sam said quickly. “I told her I wouldn’t. But- You know.” Sam cleared his throat. “If you’d said yes to her the first time…”

Sam gave him a pointed look. He was asking to get punched in the fucking face.

“No.”

“Dean, just-“

“No. I’m not takin’ advantage of her, Sammy, I’m not-“

 “It’s not taking advantage of her if she wants it!”

“She doesn’t want it-“

Sam snorted. “Oh, fuck off.”

Dean blinked, leaning back in his chair. Sam turned a little red, wincing at himself, but didn’t back down.

“Wow, Sammy. Big claws, huh.”

Sam sighed, running a hand over his face. “Dean… Just- Think about her, okay?”

Dean almost laughed. “All I fuckin’ do is think about her-“

“Then think a little harder.” Sam said flatly. “Before both of you get actually hurt.”

Dean didn’t have an answer to that. Sam didn’t seem to be asking for one. He turned and walked out of the room, leaving Dean alone. With only his coffee mug and thoughts for company. A dangerous thing to do. Dean could talk himself into and out of almost anything, if the logic police weren’t there to stop him.

He was going to do something really fucking stupid and selfish, and it was all Sam’s fault.

“Come in!” You call to the knock on your door, glancing up from your laptop as the door creaks open.

Dean shuffles into your room with his head bowed. Your face heats, and you slam the laptop closed. He doesn’t need to see you scrolling through hookup websites and think any lower of you. You’re already losing sleep over the worry you’ve fractured something between you beyond repair.

“Hi,” you whisper, and he swallows.

“Uh- Hey.”

“Hi.” What the fuck is wrong with you.

Dean’s lips twitch. “Hey.”

You start to pull the sheets between your fingers, trying not to ogle him too obviously. He’s wearing sweats and a t-shirt, and it’s sexier than all the profile pics you’ve spent hours staring at. His hair is a mess, and there are bags under his eyes, and you don’t think you’ve ever wanted to climb over him more.

“You, uh-“ He glances at your computer. “You busy?”

“No- No.” Never for him. You shove your computer onto your bedstand, moving to sit on your knees. “What’s up?”

Dean’s throat bobs. He runs a hand through his hair, huffing something close to a laugh, and shakes his head. “Jesus.”

“What-“

“Nothin’.” He clears his throat, giving you a strange look. “Did you ask Sam to sleep with you?”

Your mouth falls open. You almost trip sitting down. “I- I didn’t-“

“You didn’t?”

“No, I mean- I- He wasn’t supposed to tell you,” you whine, avoiding Dean’s stare. “I didn’t- Fuck-“

“Hey- It’s- Woah-“

Dean crosses the room in a few strides, grabbing your wrists with firm, warm hands. You’d started to pick at your nails with the anxiety. You hadn’t even realized it.

“Don’t hurt yourself, sweetheart,” he mutters, his thumb dragging a circle on your wrist.

You nod, your voice only a breath. “Okay.”

He’s so close. You can count all his crow’s feet, map his stubble, trace his lips with just your eyes. He’s still frowning at your wrist, so you allow yourself to stare.

Then he looks up. And you freeze in panic, but don’t manage to look away.

Dean’s tongue flicks over his lips. Your breath catches. Neither of you move, and you let yourself have it. For a single second, you imagine that Dean is here, in your room, on your bed, and that means something. You get lost in the warmth of his proximity, the calloused but soft feeling of his touch.

“Sammy told me something else,” Dean mutters, scanning over your slack, flushed features.

“Yeah?” You whisper, and he nods tightly.

“Yeah. Said you’re, uh-“ He clears his throat. “Said you’ve never- You know.” He cringes. “Been fucked.”

Your mouth falls open. You think you’d like to die now. “Dean-“

“Is that why you asked me?” His grip tightens on your wrist. Not allowing you to pull away. “’Cause you just wanted someone to take it?”

You drop your gaze to his crotch. There’s a soft bulge there. You’d drool over it, if you didn’t think you were going to explode any second now. 

Dean says your name, and you shake your head.

“Don’t,” you mumble. “Don’t just- Feel bad for me- You said no, that’s- It’s fine-“

“What if it’s not.”

Your eyes shoot up. You’d think he was joking, if he didn’t look so fucking serious. His jaw is set. His eyes are blown out and fixed on yours. Your mouth hangs stupidly open, and Dean smiles softly.

“Huh?” You manage to choke out, and he almost chuckles.

“What if I wanted to. Help you.”

“But-“ You blink. “You don’t.”

Dean shakes his head. “Wrong, sweetheart. I do-“

“You said you didn’t-“

“I lied.”

You stare at him. He doesn’t back down.

“Would it mean something?” He muttered, reaching up to trace the curve of your cheek. “If I did it?”

You nod weakly, leaning into his touch. It sends violent, hot shivers through your whole body. Almost like a fever. You don’t want the cure. “Would it matter to you?” You ask, and Dean’s eyes flash. His fingers curl on your cheek. He leans an inch forward, then another inch. Your lips brush, the lightest possible touch, and you let out a soft, uncertain whine.

Dean pushes forward, his lips fully crashing into yours, his kiss demanding but certain. He presses over you, pulling you a little further up on your knees. You grab the collar of his shirt for balance, squeezing your eyes shut and trying to kiss him back with as much fervor as he’s offering you.

“De- Dean-“ You gasp against his lips. “Dean-“

He groans, his arm sliding around your back so he can pull you tight to his chest. You melt into his arms, and his kisses turn messy. Open mouthed and rough, his tongue dragging over your teeth as his fingers dig into your hips. You run out of air fast, but don’t try and pull away. You don’t want this to ever end, and you’re afraid that if you dare to break the moment, it will never be repaired.

High gasps start to escape your throat, though, and Dean pulls away. He cups your face between his hands, frowning slightly, and presses his brow against yours. You struggle for air, almost pressing forward to try and kiss him again, but he holds you in place.

“Breathe, sweetheart,” he mutters, rough and thick. It’s the same voice he uses on you during hunts. When he’s giving an order you didn’t ask for.

Usually, you protest or ignore him. Right now you’re putty in his hands. He could tell you to follow him to hell, and you would. You’d do anything, just for him to never let go.

You inhale unevenly, and Dean rubs your upper back. His hand slipped under your shirt, and his palm is broad and warm. It—annoyingly—helps a lot.

“There you go,” he murmurs, watching you under hooded eyes. “That’s a good girl.”

You whine again. “Dean-“

“Sorry. Couldn’t help it.”

He doesn’t fucking look sorry. His lips are twitching, and there’s a smug glint in his eyes that’s almost dangerously intoxicating.

“Better?” He asks, and you nod, slumping closer to his chest. He doesn’t push you away.

This might be real.

“Are you sure, ‘bout this?” Dean rasps, and you almost giggle.

“Yes.”

“I’m old, sweetheart-“

“I like it.”

Dean blinks, and you stutter, so sure you should shut up but not really sure how.

“I- I mean- I like you, so- I don’t care if you’re old- I like you old- I like you-“

Dean smirks, holding your face so firmly against his  you can’t shy away.

“You- Can you- I mean- If it’s just- Just sex- You can forget I said- I think you being old is hot-“

He finally takes mercy, and shuts you up with a long, rough kiss. You hum, pushing further up on your knees, and climb slowly into Dean’s lap. He sucks on your lower lip, angling your head back as your core settles against his bulge, then pulls back with a low sigh.

“Not just sex,” he mutters, dragging his thumb over your swollen lower lip. “Not with you, baby.”

You nod, smiling wider than you probably should. “Cool.”

Dean grins back. “Yeah?”

“Mhm.”

“Cool ‘cause you like me,” he teases, shoving your hips down, right over his crotch. “Of ‘cause I’m old.”

You face burns. All you can do is stare and him and whimper, “You’re spritely.”

Dean huffs, in disbelieving amusement. “Spritely? You think I’m-“

“Youthful,” you babble quickly. “You’ve got a lot of…” You flush as he stares at you, sort of wishing he’d just kiss you and shut you up. “Youth.”

Dean’s mouth curves up. “Youth, huh.”

You nod, and he chuckles, pressing the lightest kiss over your lips.

“Hurts when I bend over now, honey, don’t think that’s very youthful of me.”

“So don’t bend over,” you mumble, and Dean snorts.

“Demanding, aren’t we?”

You shrug, trying not to turn into a puddle and miserably failing. Dean kisses your cheek, then under your eye, tracing his mouth down so he breath tickles your ear.

“Mouthy and demanding,” he rubs your hips, dragging your hips back and forth across his crotch. “Don’t worry. I’m gonna fix that.”

You whimper, and Dean’s grin grows.

“You like that, huh.”

“Dean-“

“Ah,” he kisses the corner of your mouth, moving away before you can chase his lips. “You wanted my help. This is how I’m gonna help, baby. Takin’ real good care of you,” he thrusts his hips up, and you whine as the hard outline of his cock hits your clothed pussy. “Just like this.”

 You nod, pressing your face into the crook of Dean’s neck. You don’t think you’ve ever been this turned on. It’s different, with Dean’s hands wandering your sides and his voice right in your ear. Your heart pounds and everywhere gets slick with sweat and arousal, just his dirty talk reducing you to a heap of confused nerves. Dean’s lips drag over your jaw, and you curl further around him, your nails digging into his shoulders as he nips at your throat.

“Just gotta do what I tell you, alright?” He mutters, squeezing a handful of your ass. “Can you do that, baby? Do it for me?"

You nod quickly, and Dean chuckles against your skin.

“Eager,” he drawls, pushing his fingers slowly under the hem of your shorts. “Eager and soft.”

He squeezes your ass again, his fingers brushing against the edge of your pussy. You grind backwards, trying to push him to where you need him so very desperately. He lets you, teasing his fingers over the lips of your pussy, and you whine in his ear.

“Sit still,” he grunts, and you have to bite your lower lip, but you force your hips to come to a stop.

It earns you a sharp slap of your ass, and a kiss on the side of your head. Worth it.

“That’s right,” he mutters, letting those thick fingers dance back over your cunt.  “Good work, baby girl. You fuckin’ love the attention, don’t you. Eager to please me, eager to make me proud.”

You swallow, hugging him so tight you’re a little worried you’ll choke him. Dean doesn’t even flinch. He dips two fingers into the wetness of your heat and groans right in your ear, spreading the arousal everywhere between your thighs.

“If you’re gonna hide that pretty face,” he grunts in your ear. “At least fuckin’ kiss me.”

Nervously, you wander your lips over the strong curve of his shoulders, the arch of his neck. Dean moans in your ear, his cock jumping in his jeans. His fingers keep wandering near and around your pussy, and you get a little bolder. Kissing up his jaw, over his cheek, the top of his lip. You’re panting, trying to focus on your job as Dean keeps pulling and teasing you with his touch.

“Shit,” he moans your name, tracing around your flutter entrance. “That’s it, baby, just like that-“

 Dean grabs your jaw with his free hand, like he can’t fucking help himself, and slams his lips against yours. You squeak in surprise, but kiss him back, grinding down onto his hand. His fingers dip inside of you for a moment, and you moan. Dean grunts and shoves those fingers inside of you.

Your mouth falls open, your eyes widening at the thick, pleasurable stretch. He feels so good, so fucking right, you’re worried his cock might kill you.

“Look at you,” Dean coos, smirking at your slack face. “Just my fuckin’ fingers, baby. Keep breathin’, or this is all we’re doing tonight.”

You take a deep breath, sharp and sudden, and Dean smirks in approval.

“Good girl,” he pushes his fingers a little deeper, scissoring them and bumping against a spot that makes your whole body jerk.

“Dean-“

“Shh,” he kisses you, crooking his fingers to rub against that hidden button, and you mewl against his lips. “You feel that, baby?”

“Mmm- Mhm.” You press your cheek against his, eyes fluttering as Dean keeps pushing and tickling deep inside you. “Feels good.”

“I know it does, sweet girl,” he wraps his hand back around your neck, guiding your brow to press back against his. “It’s that special little spot, gonna make everything feel good.”

His words are sweet and mocking all at once, and it sends a new gush of arousal between your legs. You watch him with wide, clouded eyes, and Dean’s smile softens for a single second. He kisses you, more gentle than before, and pulls his fingers slowly out of your cunt.

“Lie down,” he whispers before you can protest, and you swallow, but obey.

Dean hums in approval, rubbing a massive hand on your thigh.

“Everything off,” he says, and you go still.

“Everything?”

“Mhm,” he raises his brows at your flushed expression. “That gonna be a problem?”

You shake your head, wrapping your arms around your stomach. You don’t want to disappoint him, but he’s going to see you. Really, fully see you. God, you really don’t want him to see you and change his mind, and-

“Hey,”  Dean takes your hand, squeezing it gently. “You want my help?”

“Yes, please,” you breathe, and that’s all it takes. 

Dean rips off his shirt first—makin’ it even, he says—then makes quick work of his jeans. You don’t get more than a second to marvel him—flushed, tanned chest and thick everything, and heavy cock that does not look like a worm—before he’s touching you. He shimmies your shorts down, then peels your shirt over your head, leaving you in only your underwear. For a moment he just admires you, palming his cock with a tiny grin, and you roll onto your stomach.

Dean laughs, tapping your ass with a single finger. “Gettin’ shy, baby?”

“Shut up-“

“Ah.” He drags that finger down your clothed pussy. “Who tells who what to do?”

Your face burns, and you press your face further into the pillows. Dean chuckles, and you feel the bed shift as he crawls over your body. You can feel the heat coming off of him, feel the drag of his cock somewhere near your ass as he whispers in your ear.

“You were doin’ so well,” he drawls, unhooking your bra with a single hand. “Don’t get shy on me now.”

It doesn’t help. You keep grinding, trying to get some friction with the sheets. Dean’s hand comes down on your pussy with one, sharp smack, and you squeal, pushing back against his hand.

“Needy fuckin’ baby,” he mocks. “Can’t even help it, can you. Still tryin’ to be good for me.”

He hooks two fingers around your panties, pulling them tight so they push against your clit. You push back against his hand, and he smirks against your ear.

“You want a little more?”

You nod, and he snaps the fabric down, sending a tiny shock through your body.

“Say please-“

“Please,” you gasp, moving your arms up to hide your face. “Please, Dean- More- Oooh-“

Dean’s thumb finds your clit, rubbing in slow, tight circles. Your words fall off, and he fists a hand in your hair, tugging your head back to allow him to kiss you again.

He’s not cruel, with how he touches you. He’s generous, but controlled. Every stroke of your clit is deliberate, making your head spin and your mouth fall further open. That seems to be exactly how he wants you, though, because he pushes his tongue further down your throat and flicks his thumb back and forth, working you up into a writhing frenzy.

When his fingers finally push back inside of you, Dean almost seems unwilling to pull back and stop kissing you. You’re bent back and pliant under him, whimpering happily as he feeds his fore and middle finger into your hole.

“Greedy little pussy,” he rasps against your lips. “Know you’re gonna strangle my cock, baby, son of a bitch-"

He groans, like he’s the one being fingered into oblivion. He’s set a harsh pace with his wrist, snapping his fingers in and out of your cunt without relent. His thumb moved away from your clit, replaced by the heel of his palm, rubbing in tight, unrelenting circles on your swollen clit.

Every single time, he hits that spot inside of you, and your head is starting to get light. All the electricity and heat in your body is pushing down into your core, building like a bomb and threatening to explode. You almost sob, with how overwhelming the sensation is. Dean notices, kissing you a little softer.

“Poor girl,” he mutters. “Already like this and I’m not even properly fuckin’ you.”

“Your- Your hands,” you push out the word between sharp breaths. “They’re big.”

Dean grunts, his cock jumping near your ass. “Yeah, sweetheart? You like how fuckin’ big my hands are?”

“Mh- Mhm.”

You try to kiss him again. He pulls back, moving his hand impossibly faster against your cunt.

“Words,” he grunts. “You’re not stupid enough to not speak, not yet.”

“Like it,” you breathe out. “Love- Love it, Dean, oh- Oh my god-“

You moan again, and Dean grunts. His hips are starting to jerk near your ass, making him rut against you as his fingers work.

“Your close,” he mutters, pressing his fingers fully inside and crooking them against that gooey spot. “Cum for me, pretty girl. Now.”

His voice must have some kind of supernatural power over you, because that pressure in your lower tummy bursts, and your orgasm rips through you link a hurricane. Your thighs clench, trapping Dean’s hand between your legs, and he groans, rubbing his fingers harsher and harsher against your g-spot. You’re shaking and rolling beneath him, and he has to grab the back of your neck and pin it down to keep you still.

Dean works you through your orgasm, whispering low praise in your ear as you float back down to earth. Your pussy feels empty, when his fingers finally pull away. Your eyes are slightly crossed, and your smile is dazed and a little stupid.

You don’t even squeak, when Dean grabs your thigh and flips you over. You keen, back arching and body twitching, but you’re mostly just staring stupidly and happily up at him. Dean swallows, his chest rising and falling fast, and leans down to press a soft kiss to your lips. You hum, eyes fluttering shut, and cup the back of his neck to hold him against you.

He drags his fingers lazily through the mess between your thighs, sending pleasurable little shivers up your spine. He drags your panties fully off your body, holding them up to his nose and taking a deep, long whiff before tossing them off to the side. He gathers your arousal on his fingers and slowly pulls away, rising over you with parted lips and gleaming, almost wholly black eyes.

Dean sucks your juices off his fingers, lapping them up with his tongue and a lazy, knowing smirk. Your breath catches. You almost push up to try and grab him, but you’re still foggy and boneless from the orgasm, and he shoves you back down with a broad hand splayed over your tummy.

“Dean-“

You cut yourself off under his stern gaze, swallowing nervously.

“Please?” You try again, and he chuckles.

“You’re cute.”

“I- I am not-“

“Yeah, you are. Cute when you cum for me,” he dips his fingers back into you, smirking lazily. “Cute when I touch you. Cute when you beg.”

“Deeeean-“

“Deeean,” he mocks, squeezing your upper thigh. “Listen to you. Fuckin’ adorable.”

You flush, a new wave of arousal hitting you like a rising tide, and you don’t even understand how you could possibly be ready that fast. Dean watches you pussy tremble and flutter, letting out a slow, rough breath.

“Son of a bitch,” he shakes his head, his hand moving to rub against his cock. “You got no idea what you do to me, baby, no fuckin’ idea.”

You swallow, watching him move against himself, almost enchanted. He really is prettier than is fair, in every possible way. His cock is thick and long, flushed at the head and leaking pre-cum against his thumb. Your tongue flicks over your lips, as you try to mentally measure the girth and length of him. You’ve taken toys before, when you got really curious. He’s bigger.

“You wanna touch, sweetheart?” He prompts, and you nod, your tongue flicking over your lips.

Dean pushes his hips forward, slowly taking your hand and guiding it against his shaft. He’s warm. Warm and hard. You dance your fingers down the length of him and he grunts, a vein ticking in his neck.

“Easy…” He rasps, and you nod nervously.

You find his balls, give them a light squeeze, and Dean catches your wrist.

“That’s enough.” He mutters, twining your fingers together. “Jesus, woman, gonna blow it before I even get inside of you.”

Your eyes widen. You’d almost forgotten about that part.

“That’s not going to fit inside of me.”

Dean chuckles. “Yeah, it will.”

“No, I mean like- It can’t-“

“It can.”

“Dean, I’m serious-“

He shuts you up with a quick rough kiss, and you go embarrassingly limp. His cock rubs between the folds of your pussy, bumping and pressing against your clit, and your breath hitches. Oh, God.

“Just do what I tell ya,” he mutters. “We’re gonna make it fit.”

You do. It is very easy to do what Dean tells you, when he follows through on all his promises. When he gives you such low and certain orders, and you find yourself molding perfectly around his cock.

Because it does fit. Somehow, Dean spreads your legs and kisses your pussy once—as if he can’t help himself—before crawling over you and slowly pushing the head of his cock inside of you. It’s tight at first. He grunts, pressing his brow to you shoulder, and rubs tight circle around your clit with his thumb.

“Open up for me, baby,” he rasps. “C’mon.”

You go limp with every inch he feeds you. The stretch is glorious, pulling you apart with every drag over your fluttering walls, every low grunt of your name from Dean’s lips. His determination to tease you seems to dissolve, by the time he’s fully seated inside of you, his balls pressed against your ass. He pants in your ear, hot and heavy, and cradles your body in his arms like it’s fragile.

“Slow,” he mutters, and it sounds like he’s talking to himself more than you. “Gonna go slow.”

You keen, at the first, lazy thrust of his hips. A lewd, wet sound fills the air, and the head of Dean’s cock pushes right up against that already abused spot inside of you, making stars dance behind your eyes. Every roll of Dean’s hips makes your whole body spark. He kisses all over your face, his own voice thick and wrecked as you clench around him.  

“Takin’ me so well, baby,” he rasps. “Feels good, doesn’t it. Feels so fuckin’ good, bein’ filled up with cock like you deserve-“

His words fall into a moan, his hips snapping forward, and the air gets knocked from your lungs. A sound you’ve never heard escapes you, and Dean chuckles, kissing your open mouth as he repeats the motion.

“Yeah, you like that.” He pulls almost fully out, then slams back forward. “Say it, baby girl, say you like it-“

“I like it,” you gasp out, sounding drunk to your own ears. “Love it, Dean- Fuck- Fuuuck-“

Dean captures your mouth in another kiss, and sets a brutal, drilling pace. You’re split open with every thrust, your every nerve on fire as he fucks you like a machine. He never gets too fast, just hard. Over and over and over again, until you’re gasping for air and clawing at his shoulders. That pressure turns molten and demanding, threatening to burst. Dean’s fingers dig into your hips. He moans in your ear, his own words staring to slur.

“Tight,” he moans. “So fuckin’ tight- I- I can’t- Shit-“

Dean’s hands fumble, dragging over your thighs and as he gropes for your pussy. Two fumbling fingers find it, rubbing tight circles, and you cry out, clenching down on his cock.

“Let go, sweetheart, need you to let for ‘f me- Fuck-“

Your orgasm hits you even harder than before, and your vision goes white. Your pussy flutters and clenches, something hot gushing out as your body trembles with overwhelming pleasure. It’s a strange sensation, but not bad. Not even close. You think you scream with pleasure, but Dean slams his mouth over yours and muffles the sound.

His hips stutter and jerk. You whine his name and he grunts, slamming forward and burying himself at the hilt as his cum spurts deep inside you, mixing with your own release.

You’re almost gone to the world. Dean lies over you, kissing you as you float back down, murmuring praise you can barely hear.

“Gonna clean you up,” he grunts, and you whine when his weight disappears.

“Deeean.” You grab at the air and catch his bicep. “Stay.”

You pout at him, eyes watery and hopeful. He just chuckles, kissing your knuckles before drawing back up, and promising to return.

He better. You really don’t want to let go of him now.

Dean brings a wet, warm towel, and cleans between your thighs. You didn’t realize how sore you were until he touches you with such light hands, but it’s a good kind of sore. When you moan, it’s not even really in pain.

He brings you water. A snack and a fresh shirt, that he bundles you in like a penguin. You somehow end up curled against his chest, half asleep and smiling against his bare, warm chest.

“I like you,” Dean says suddenly, and you beam. You don’t think you’ve ever felt so bubbly in your life.

“I like you too-“

“No,” his jaw works, the words low and tight. “I like like you- Like- Fuck-“

He runs a hand over his face, shaking his head. It’s almost adorable.

“You- You’re just- That really wasn’t nothin’ for me, sweetheart, not even close-“

You take his trick. You push up on his chest, press your lips together, and kiss him until he shuts the fuck up. He kisses you back immediately, cupping your face between shaking hands. You smile against his lips, pulling back just enough to whisper, “I like you too.”

Dean’s eyes snap open, his voice hoarse. “Really?”

“Yeah,” you flush. “A- A lot.”

Dean grins. He smiles wider than you knew he could, and slams a shorter rougher kiss against your lips before pulling back again. Like he can’t stand not to look at you for too long.

“Can I take you out?” He says, and you nod.

“Can we have more sex,” you whisper, and he laughs, pressing another kiss against your lips.

“Any time you want, baby.” He says. “You’re mine now.”

✦End note: drooling for him ✦

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