summary - She’s a teacher: sweet, innocent, and sometimes naive. He’s a mob boss: mysterious, cold, and sometimes dangerous. No matter how you look at it, the two of them together don’t make sense, but something about Alice Berkley intrigues Dean Winchester. Once she enters his life, he can’t seem to let her go. He knows keeping her close is a bad idea, but he never claimed to make good choices.
warnings - this series includes blood, violence, drinking, smut, age gap / daddy kink, physical abuse, sexual assault, miscarriages, and language (each part will be labeled with specific warnings)
A/N - I guess Dani’s favorite AU to write is the mob boss AU. I mean I do enjoy my fair share of Scorsese films. The Departed? *chef’s kiss*
mob!dean-charles chapman au
warnings: language, mentions of drug use
word count: 2.3k
series masterlist
Justin has been added to the character list so check that out before you read this chapter!
I didn’t really have many friends growing up. Not a lot of parents were crazy about their kids hanging out with Leo Stone’s son. You really couldn’t blame them for that, my dad is a fucking psycho.
Justin Martinez was my childhood best friend. My mom and his mom were best friends when they were teenagers and as soon as they had kids of their own, they wanted us to have the same friendship they did. However, when we were both six, Justin’s mom died of breast cancer which hit my mom hard, she wasn’t herself for a long time.
After her death, Justin had to move in with his dad who lived in Brooklyn which was around an hour away. Mom would usually drive me there and drop me off to stay the night but after her death, I’d have whatever nanny I had for the time being do it.
Justin’s dad was an asshole; not as much as my dad was but he was definitely up there. He was a drunk junkie and an abusive asshole that spent his days mooching money off of Justin’s mom’s side of the family and saying it was to “help take care of him” and sticking needles in different parts of his body. None of his time was spent taking actual good care of his son and none of the money he’d get was used for Justin.
As I grew up, I grew protective of him. I wasn’t afraid to call his dad a piece of shit to his face, or even throwing in a punch, knocking him out cold. It didn’t really take much to knock out someone that’s drunk or high, or both. One good hit will have them hit the ground so fast and passed out for a couple of hours.
I don’t know if it was because I couldn’t defend myself like that with my own dad and being able to help someone that went through the shit I did kind of comforted me in some kind of way. Or, maybe it was just because, in the words of my father, “I’m a fucking psycho”.
Whatever it was, I didn’t care, just as long as he was okay.
Justin’s dad ended up going to prison for 15 years for second-degree robbery when we were both 15. After this, he ended up moving away to Massachusetts to live with his aunt and uncle who were loaded with money.
Having to say goodbye to my best friend and my only friend really fucking sucked but I was happy for him, he deserved to have a chance at having a good life and be surrounded by family that loved him and cared for him.
After moving, he never tried to get in touch with me. He’d either send me short messages or just ignore me. He never tried to call, never answered my calls, and never made plans with me to visit or for me to visit him. I could understand though, once you move away from your toxic life and start a new one that’s actually not shitty, you never wanna go back.
It sucked to not feel needed anymore but it fucking sucked even more to lose what you needed.
_______________
My hands felt clammy, the collar of my dress shirt felt like it was choking me, and my leg couldn’t stop bouncing.
“Can you roll the window down?” I ask my driver from the backseat.
He rolls it down as one of my guards that’s sitting next to me looks at me with concern, “You okay boss?”
Boss. This dude was like 20 years older than me. Hell would have to freeze over before I’d call anyone younger than me “boss”.
I nod and stick my head out of the window just a little bit, “Yeah, I’m just hot.”
I was on my way to the “meeting” my father wanted me to have with one of his workers at the warehouse that our shipments of “goods” went out of. Since this was about missing money, I’m guessing this meeting is gonna be exactly like the one on the yacht. At least this time I wouldn’t have my dad and grandpa breathing down my neck and judging me for every fucking move I make.
I can’t lie and say that I’m not nervous, of course, I am, I’m human. There’s nothing wrong with it as long as I didn’t show that, when you start showing signs in any way that you’re not confident, people will automatically get the upper hand on you.
I ran through the plan on what I was going to do when I found the guy. Maybe act all buddy buddy to him and then just go all serious and scare the shit out of him until he gives me an answer? Or maybe just start it by beating the shit out of him and ask questions after?
I was taken away from my thoughts as the large warehouse came into view. I let out a deep breath before getting out of the car as it stopped right in front of the building, my men followed me into the entrance doors.
I approached the first worker I saw, “Is there a Justin that works here?”
He makes eye contact with me, his eyes slightly widen as he realizes who I am, “Uh yes sir, do you want me to get him or show you where he is?”
“Bring him to me, one of my men will go with you to get him then bring him to me. I’ll be out on the docks down at the water,” I say before turning around and walking out, down the hill to the water.
My two other men stood by my side as I waited for the guy to be brought out. I put my hand on my holster to prepare for any case where the guy comes out with guns blazing.
My heart was beginning to pound harder than it was in the car. I really should’ve smoked a cigarette first before I decided to just eagerly barge into the warehouse. I was just really ready to get this over with.
As I was internally fighting with myself on if I should just say fuck it and pull out a cigarette, two figures came down the hill. I recognized my guard as one of them and the other one was a bit smaller.
I fixed my posture and clenched my jaw as I gripped the handle of the gun that was still in the holster that was attached to my hip. I had a hard grip on it for maybe 15 seconds before I froze in place.
My heart began pounding faster than before, I could feel myself getting hot as I slowly began to recognize the figure that was next to my guard.
Holy. Fucking. Shit.
The look of confidence I attempted was completely wiped away. My guard stood off to the side as I stared at the approaching figure with wide eyes and my mouth slightly open.
“Hey, Dean.”
Justin fucking Martinez.
There he was, right in front of me, seven years older. He looks so different but somehow still the same. He was the same height as me and had the same face full of freckles but had facial hair and he seemed to carry himself in a way I can’t explain.
7 years is a lot of time and while everyone changes in that amount of time, he was different. He wasn’t that same vulnerable, scared, angry kid he was when we were friends.
He looked like he has been through shit but still carried himself with confidence and looked fearless.
He was attractive.
“You work here?” I ask, finally being able to find the words to speak.
He smirked, “You mean I work for you? Yeah, I do.”
As I go to speak he cuts me off, “No, your dad doesn’t know that I work here. He really wasn’t involved with the hiring process here. He has people for that. Or should I say had since they’re your people now.”
I was confused by his monotone voice yet playful look he had on his face. I don’t know if it’s the shock of seeing him again or the fact that I was about to have a “meeting” with my childhood best friend that made me feel so tense and uncomfortable but I knew he could tell I was. He automatically had the upper hand.
I sigh and look away from him for the first time since I saw him, “Listen, Justin, I’m just gonna ask you straight up.”
I look back at him, staring straight into his dark brown eyes, “Did you take money from us?”
He frowns and puts his hands in his pocket, he’d do that when he was nervous, maybe I had the upper hand now.
He shook his head and shrugged, “Why would I steal from you?”
“You didn’t steal from me, you stole from my dad.”
“Then why are you here?”
“Because-”
“Because your dad told you to? So you’re still listening to that asshole, even when you’re the one who’s supposed to be in charge?”
I had to stop and take a second to think about what he said. He wasn’t wrong, my father was making me clean up his messes or do his dirty work for him when it’s me that owns all of this.
“Guys, can you give us some time to talk alone? I’ll be fine,” I said to all my guards. They gave me an unsure look before nodding and walking back up the hill where they can still see me but can give me the privacy I needed.
“Just tell me, did you steal money? I’m not gonna kill you over it or anything like that. I just wanna know,” I asked lowly.
Justin sighed and looked out at the water, shaking his head, “I needed the money.”
I close my eyes and sigh. Why Justin, why?
“Before you freak the fuck out, just listen to me, please?” He begs.
I nod before sitting down on the edge of the dock, swinging my legs slightly as I look down at the dark waters below me.
Justin sits down next to me and sighs, “I won’t lie, life was pretty fucking great when I first moved to Massachusetts.”
Ow.
“I mean, not having you there felt really fucking weird and it sucked. I do still feel like an asshole for completely ghosting you cause shit, you were all I had after my mom died. But I was 15, I found a new group of friends, who were complete douchebags. Like seriously, the old me and you would’ve beat the shit out of them,” Justin and I chuckle at the same time, remembering how brutal we were to the arrogant assholes we went to school with.
“Anyways, after I graduated, things just went downhill. My uncle was a fucking prick and kicked me out because “his father kicked him out when he was 18 and it taught him so many things in life so he wanted the same for me” and all that shit but they fucking knew I had nothing planned out which, I will admit, it’s my fault but holy fuck they didn’t even give me time to try and get my shit together. They just threw me out and wouldn’t let me back in. So, because I was basically homeless, I got into the wrong crowd and just got into drugs and alcohol, just like my piece of shit sperm donor. But, one night I just got completely fucked and I ended up having to go to the hospital to get my stomach pumped which, of course, put me in rehab. Dean, the fucking place I went to was so fucking weird and shit but it helped me find a sponsor who basically acts as my babysitter just in case I almost relapse. And because of him, I got this job a little over a year ago.”
A YEAR ago?
“Wait, you’ve been working here for over a year and never thought to just try and get ahold of me?” I ask offended.
Justin chuckled, “Honestly, I thought you would’ve been out of here when you turned 18.”
Fuck, I wish.
“I should’ve but I just can’t go without figuring out what happened to my mom,” I say with a sigh.
“Yeah, I don’t blame you. But I swear Dean, I only took money to pay rent, I was so fucking behind that they were about to evict me and-”
“Justin it’s fine, I don’t give a shit about what you took from my dad,” I say with a smirk.
He lets out a sigh of relief and jokingly wipes his forehead, “Thank god. I’m not gonna lie Dean, you have gotten intimidating as fuck,” he exclaims.
I laugh and shake my head, “I have been learning from my wonderful father and grandpa.”
Justin rolls his eyes, “Fuck them. You are so much better and smarter than them. I hope you take this bullshit business from them and drive it straight into the fucking ground.”
As soon as he said that my plan instantly came into my thoughts. Justin is the only person on this earth that I have always trusted and that I know will always have my back. He could help me with it and greatly benefit from it.
I turn my head to face him, grinning slightly.
Justin faces me and smirks, “Uh oh, I know that look. What are you planning?”
I stand up and adjust my jacket as I look down at him, his dark eyes already focused on me, “I’m gonna take the business, but, I’m gonna drive them straight into the fucking ground…and I want you to help me.”
The end of the school day meant chaos in the hallways. Little kids with big backpacks were running to the front of the school, eager to catch their bus or meet their parents.
Things were busy for a few minutes as Alice stood on the curb and waved goodbye to her students. Just when she thought they were all gone, she realized one of her students was sitting alone on the grass. Her name was Lexi, and she was a total sweetheart. Teachers weren't supposed to have favorites, but this girl was hers. Six-years-old with brown hair and big brown eyes; usually she was all giggles and smiles, but when Alice looked at her, she was picking at the grass with a frown etched on her face.
Lexi's parents were both lawyers, and Alice knew they had busy work schedules. Everyday, Lexi came to class with a slip of paper that said who would be picking her up: Sam, Jess, Castiel, or Hannah. Alice realized just then that she hadn't given her a paper that day. She walked over to Lexi and sat beside her. Lexi wouldn't look at her. "Who's picking you up today, Lexi?" she asked. "You didn't give me a paper. Do you know?" She silently shook her head no. Alice looked at her watch: 4:26. Whoever it was was almost half an hour late, which was unusual for Lexi's pick-ups. "Well how about I call your mom and check in with her, yeah?"
Lexi nodded, so Alice stood up and walked a few steps away to make the phone call. She unlocked her phone and scrolled through her contacts, finding Lexi's mom's name quickly from when she entered all the students' emergency contacts. The line rang and rang, and just when she thought she would get sent to voicemail, Lexi's mom picked up. "Hello?"
"Hi Mrs. Winchester," she said, "this is Alice Berkley, Lexi's teacher."
"Is everything okay?" her mom said, sounding panicked.
"Yeah, yeah, everything's fine," Alice said. "It's just, school ended at 4:00 and no one's come to pick her up yet."
"Christ," she mumbled. "Sorry. That'll be my brother-in-law. He swore he'd be on time. I'm so sorry."
"It's okay," she said. "I'll just take her back into my classroom while we wait."
"I don't want to make any trouble for you," Mrs. Winchester said. "If you need to head home-"
"No, it's no trouble," she said. "I'm usually here for a while after school gets out anyway."
"You're sure?"
"Yes, Mrs. Winchester, it's okay," she said.
"Thank you," she breathed out, sounding relieved. "Also-" She laughed lightly. "-call me Jess."
"Okay," she said with a chuckle. "Well, Lexi and I will wait inside until your brother-in-law-"
"Dean," she said.
"Dean," Alice repeated. "Until Dean gets here."
Jess thanked her again, and Alice hung up the phone.
When she walked back over to Lexi, the girl sucked her lower lip between her teeth, looking like she was about to cry. Alice felt her heart ache for her. She reached out her hands for Lexi to take. "How about we go back inside while we wait for your uncle?" she offered. "I've got some snacks, and you know snacks make everything better." Instantly, Lexi's face lit up. She took Alice's hands, stood up, and put her backpack over her shoulders.
Alice was born and raised in Kansas, but it wasn't exactly where she wanted to spend her whole life. Still, it didn't take long for her to learn that things didn't always go to plan. Her plan was to go to college in New York and move there when she graduated. The first part she had accomplished with four years at NYU. The second? Well, there had been a few bumps that led her back to Lawrance. And now, she was a 22-year-old teaching at the same elementary school in Topeka that she had once attended.
As soon as they were back inside and Alice had given Lexi a cookie, she found Dean's number in her phone as another one of Lexi's emergency contacts. She shot him a quick message: Hi, Mr. Winchester, this is Alice Berkley, Lexi's teacher. I already called her mom and told her, but Lexi and I are waiting inside in my classroom, just so you know! One of the secretaries will buzz you in through the office and show you to my room.
Lexi ate the cookie quietly at her desk, and Alice kept turning her phone over in her hands, waiting for it to miraculously light up with something from Dean. Where was this guy?
"I have a real good family," Lexi suddenly said. She licked her lips and looked up at Alice. "They have big grown-up jobs so sometimes they get busy. They still love me lots, though."
"Oh, I know that honey," Alice said quickly. She didn't want the girl to think she was judging her uncle, even though she sort of was. Lexi finished the cookie, and Alice stood up from her own desk. She went into one of the cubbies and grabbed some coloring pages, then sat across from Lexi at her desk and grabbed a box of crayons. She slid a coloring page to Lexi with a smile. "You did really good in math today," she said. Lexi smiled and grabbed a crayon to start to color.
A few blocks away, Dean had finally reached for his phone after a couple hours of sparring with Cas. He wiped the sweat from his brow, took a sip of his water, and unlocked his phone, seeing a text from an unknown number: Hi, Mr. Winchester, this is Alice Berkley, Lexi's teacher. I already called her mom and told her, but Lexi and I are waiting inside my classroom, just so you know! One of the secretaries will buzz you in through the office and show you to my room.
"Shit!" Dean said, almost dropping the water bottle to the ground. He managed to set it down and grab his gym bag.
"Where're you going?" Cas asked as he watched Dean stumble to get his car keys.
"I forgot to pick up Lexi," Dean said.
"Jess only reminded you a hundred times," Cas said. Dean flipped him off over his shoulder as he rushed out of the bunker and into the garage.
Dean got in his Impala and pulled out his phone to find the address of his niece's school, then sped off in that direction. He knew he must've looked like the shitiest guy ever to this teacher, and he knew he'd get an earful from Sam and Jess later on. He loved Lexi, and she thought he was the greatest uncle. He hated letting her down almost as much as he hated letting Sammy down.
Alice was in the middle of singing with Lexi to one of the songs from her classroom appropriate playlist -"Firework" by Katy Perry- when Lexi's eyes suddenly lit up. "Uncle Dean!" she cheered. Alice turned and saw a handsome man walking into the room. He locked eyes with Lexi and smiled brightly, then all but ran over to the two girls and lifted Lexi in the air.
"Hey, kid!" he cheered, placing a kiss to his niece's cheek. Lexi latched her arms around his neck and her legs around his side, clinging to him like a koala. Now, Dean turned to Alice. He not-so-subtly let his eyes rake over her. He knew he was staring, but he never tried to hide when he checked girls out. He didn't care. Why should he? He was Dean Winchester. Girls loved it when he shamelessly stared at them. But Alice didn't stare flirtatiously back at him. In fact, she quickly broke his gaze.
She knew she looked fine. She always felt confident in her teacher outfits. Today she was wearing a sleeveless rainbow-striped dress. Still, she felt weird under his gaze, like something about her was probably out of place. Not that this guy looked all that impressive. He was wearing basketball shorts, a t-shirt, and some black Nikes. His brown hair flopped messily on his head, and it looked like his bottom lip was healing from a cut. His hands were bruised, his knuckles a bit red. Still, he was hot. Undeniably hot. How could someone make such a sloppy outfit look so sexy?
Sexy? Dude, Alice, he's like easily ten years older than you. Plus, that's Lexi's uncle. Not cool. Not cool.
"You're Alice?" Dean asked.
"It's Ms. Alice, Uncle Dean," Lexi said, poking his cheek. "You've got to be polite." Dean cracked a smile, his eyes squinting in happiness as he looked down at his niece.
"I'm so sorry, Ms. Alice," he said, shooting Alice a playful wink. Her cheeks turned warm as she pressed her lips into a tight line to hide a smile. "I lost track of time," he explained. "I feel terrible."
"Don't worry about it," she said, waving a hand dismissively. She grinned at Lexi. "Don't tell the others, but Lexi is one of my favorites. I didn't mind spending some extra time with her." Lexi laughed and buried her head in Dean's neck. He chuckled and rubbed the back of her head.
"Well, it is getting close to dinner time," he said. "Your mom and dad'll have a fit if you're not home soon." Lexi nodded, and Dean turned his attention to Alice again. "What do I owe ya for watching her?"
"Seriously, don't worry about it," she said. "It's not like I bought her dinner."
"I have to pay you back somehow," Dean said.
"It's really fine."
Dean sighed and licked his lips. The two of them stared at each other for a moment, and she was the one to break eye contact again as she looked down at her hands.
"Well, we better get going," Dean said. "Thank you for looking after her. I promise, I will never be late again."
"I might hold you to that," she said back. Dean winked.
"Oh, I'm counting on it."
Alice walked them outside, watched as he buckled Lexi up into her carseat, then sent him a wave as he drove away. She went back to her classroom, cleaned up the small messes her students had left, packed up her things, and went out to her Jeep. While she was teaching in Topeka, she lived in Lawrence, so she had a 30 minute drive home.
As soon as she got to her apartment, she toed her shoes off and peeled off her jacket as she went into her bedroom. She changed out of her dress and into her pajamas, even though it was only a little bit past 5:15. Her stomach grumbled, so she decided to make some ramen. She liked cooking, sure, but after long days at school, she was always too tired to prepare anything. When she spent four years studying elementary education, no one told her how exhausted she would be everyday. Well, maybe they did tell her, but back then, she was still wearing those rose colored glasses. Teaching definitely was not all rainbows and butterflies, but she still loved it.
Her ramen spun in the microwave as she poured herself a glass of wine. She plugged her phone into the speaker that she kept in the kitchen and started playing some music. "Share Your Address" by Ben Platt floated through the air, and she stood on her tiptoes with her glass and danced around the kitchen. Once her ramen was done, she stopped her music and took a seat on the floor in front of her coffee table in the living room to eat. She flicked on the TV and opened the Netflix app so she could put on Criminal Minds, her current guilty pleasure. The show itself wasn't relaxing, but this was her only time to take a breath from work. Her routine everyday was the same. The monotony of her life made her feel like a middle aged lady who had already given up. Is that what all first year teachers felt like?
After watching an episode, she pulled out her folder of math tests to grade. Once she did that, she moved onto finishing the science lesson for the next day. Before she knew it, she was yawning and struggling to keep her eyes open. She crawled into bed and plugged her phone into its charger, then checked her text messages one last time, seeing she had a text from Lexi's mom: Hi Alice! Thanks so much for watching out for Lexi today. She told me you gave her a little snack. You so didn't have to do that! You're too sweet. Lexi absolutely adores you. Please let me know if there's anything I can do to repay you
She smiled at how kind Jess was as she texted her back: It was no problem at all. Lexi is a great kid. I already told Dean you don't need to repay me. I'm happy to help
Jess sent Alice a smiley face back, so she locked her screen and headed to bed.
-
Dean smiled as Lexi chatted throughout the entire car ride back to Sam and Jess' house. "I did so good in math today," she said. "Ms. Alice even told me so."
"That's great, kid," Dean said, glancing at her in the rearview mirror.
"My friend Emily even asked me to help her," she said, swinging her legs and kicking her feet against her seat. "Ms. Alice told me I should be a teacher someday. She's so nice. I wish she was like my aunt." She gasped, her jaw dropping as if she just made an unbelievable discovery. "Uncle Dean! You should marry her." The corner of Dean's lip curved up into a smirk.
"Yeah?" he said. "You think so?"
"She's so pretty, isn't she?" she asked. Dean licked his lips and let out a laugh through his nose.
"Yeah," he said. "She's very pretty."
Dean obviously couldn't tell his six-year-old niece what he really thought of her teacher. The truth was, Dean's thoughts were filthy the minute he saw her. She radiated innocence. He could see it when she looked away as soon as he allowed his eyes to rake over her body. Dean was usually one who liked experienced girls. He never saw the point in having a one night stand with a girl who didn't know what she was doing, but as soon as he saw Alice, he couldn't stop himself from thinking about fucking that innocence right out of her.
Dean cleared his throat and adjusted his grip on the steering wheel. Lexi said his name again like she had said it a few times while he was lost in his thoughts. "What's that, kiddo?" he asked.
"Should I tell her you like her?" she asked.
Dean laughed. "I don't even know her!"
"I do!" Lexi said. "I can tell you all about her. She's pretty, and she's the best reader I've ever, ever seen, and she's very nice, and she says I'm her favorite. I'm your favorite too, so you already have a lot in common." Dean laughed again and ran a hand through his hair.
"She sounds like a nice girl," he said.
"You should ask her on a date," Lexi said.
"Why are you trying to set me up with your teacher?" Dean asked, looking at his niece in the rearview mirror again. Lexi shrugged and looked out the window.
"Sometimes everybody's busy," she said. "Ms. Alice is nice, and if you're married, I can see her more."
Just when she said that, Dean pulled the car into his brother's driveway. He turned around to look at his niece, then squeezed her knee so she would look at him. "You okay, kid?" he asked. Lexi pouted and sighed.
"You forgot me today," she said. Dean could hear her voice shake, and his heart broke with guilt. "But Ms. Alice helped me when everyone else was too busy."
Dean sighed and got out of the car, quickly jogging around to get Lexi out of her seat. He picked her up and held her close to him. "I'm so sorry I was late," Dean said. "I'll never, ever, ever be late again."
"Promise?" Lexi asked, looking up at him with the puppy dog eyes she inherited from her dad.
"Cross my heart," he said.
"Good," she said, resting her head on his shoulder. They were both quiet as Dean placed a kiss to the top of her head and walked her into the house. "I still think you should tell her she's pretty," Lexi mumbled as she buried her head in his neck.
He chuckled. "Okay, kid. Okay."
Dean walked into his brother's house, and set Lexi on the ground so she could kick off her own shoes. "We're home!" he called. He and Lexi walked into the house and to the kitchen where Jess was finishing up dinner. Jess smiled at Lexi, though it didn't meet her eyes.
"Hey sweetie," she said, kneeling down to kiss her daughter's cheek. "Why don't you go get washed up for supper?" Lexi nodded and skipped out of the room. Dean put his hands on his hips and hung his head, knowing he was about to get an earful from his brother and sister-in-law. He walked over to the fridge and got himself a beer.
"Seriously, Dean?" Sam said, speaking up before his brother could even open his drink. "45 minutes late?"
"I know," he said, running a hand through his hair. "I was working out with Cas. Lost track of time. Lex already gave me the puppy dog eyes about it, so you don't have to make me feel bad too."
"You're just lucky her teacher is so nice," Jess said. "What if she couldn't stay with her? What if she was angry?"
"Well-" Dean shrugged and took a sip of his beer. "-good thing we'll never know." Jess threw her hands up with a sigh and left the room, presumably to catch her breath before she blew up. Dean watched her and took another drink from his beer. As soon as both men heard her footsteps fade, Sam shot Dean an annoyed look.
"Really?" Sam said to the older Winchester.
"Look, I really am sorry, man," Dean said, leaning up against the counter in the kitchen. "You know I'd die for Lex."
"I know," Sam said, running a hand through his hair. "Can you just be on time next week? You're on every Thursday from now on."
"100%," Dean said. "I already told her teacher I wouldn't be late again." Sam's eyebrows raised as a slightly amused grin grew on his face.
"You mean her cute, young teacher?" Sam teased.
"Young?" Dean asked, scratching his beard before drinking his beer again. "I hadn't noticed."
"Dude," Sam laughed, "she's like 22. How did you not notice?" Dean's lips turned down as he nodded and sipped his beer. "Dean," Sam said with a scoff, "you cannot tap my daughter's teacher."
"Lexi wants me to take her on a date," Dean said with a grin.
"She's hardly your type," Sam said.
Dean shrugged. "Maybe I'm a changed man."
"For a 22-year-old?" Sam said back. Dean shrugged again, a grin growing on his lips. "You're disgusting." Dean just laughed and sat beside Sam at the kitchen table. "How'd the handoff go?" Sam asked his brother.
"Crowley kept up his end for once," Dean said. "Teaming up against Lucifer's made working with him slightly less insufferable."
"Really?" Sam said, raising his eyebrows again.
Dean scoffed. "Emphasize slightly." Sam laughed, and Dean downed the rest of his beer. "How's party planning?" he asked as he walked into the kitchen to get rid of his beer bottle. Now, Sam laughed.
"Jess is thriving," Sam said. "I just want it to be over so we can actually start working."
Dean scoffed. "Classic, Sammy."
"Shut up," Sam said. Dean grinned and sighed.
"Alright," he said. "I'll catch you at dinner on Saturday."
Dean headed back out to his Impala and drove to his apartment. The whole time, his mind was reeling. Then again, his mind was always reeling. Between the job and Sam's firm opening up, he hardly had time to take a breath. Now though, he was thinking of Alice. Dean wasn't a creep, but when he had his eyes set on a woman, he got her.
As soon as she got out of the shower, Alice saw she had gotten a text from Dean.
Dean: Do you have a favorite movie?
She responded almost instantly: I have three
Dean: What are they?
Alice: The Princess Bride because it's funny, Matilda because it kind of helped me decide to be a teacher, and Good Will Hunting
Dean: You don't have a reason for that one?
At this, she hesitated. She did have a reason, but the reason led into her talking about her dreams of pursuing a masters degree which would inevitably lead to her talking about Greg which she didn't want to do. So, she simplified.
Alice: There's a lot of reasons. It's complex and tragic but also moving and beautiful. It makes me feel feelings lol
Dean: Got it. You coming over soon?
Alice: Just gotta pack my bag and I'll be right over
When Alice got to Dean's building, she went inside the lobby and saw the usual man at the reception desk. She walked over to him. "Derek, right?" she said.
"Yes ma'am," he said. "You're a friend of Mr. Winchester, correct?"
"Yeah, Alice Berkley," she said, reaching her hand out for him to shake.
"How can I help you, Ms. Berkley?" he asked. She felt herself blush at his formal tone.
"You can just call me Alice," she said to him.
He smiled. "Well how can I help you, Alice?"
"You can tell me how to get to Dean's place without Dean," she said. "Every time I've been here, he's been with me."
"Well, you would need Mr. Winchester's key or key code," he said.
"And I don't have either of those," she said with a chuckle. "I'll just give him a call then."
"I would let you in myself," Derek said, "but I can't break protocol."
"It's fine," she said with a wave of her hand. "Thank you though."
She called Dean, and he was down in less than a minute. He greeted Derek before taking Alice's hand and walking with her over to the elevator.
"I would write down my key code for you," he said, "but I don't like anyone having it written down anywhere just in case it gets into the wrong hands. You can always memorize it though."
"Or I can just make you come down whenever I come over," she teased. Dean playfully rolled his eyes.
"It's six digits," he said. "091305."
"Is that a date or something?" she asked.
"Nah," he said. "Just some random numbers. I try not to make any codes dates because those can be too easy to guess. You'd think putting my mom's birthday or something would be smart, but those dates aren't as safe as you think, especially not for me when I've got about a hundred people who are always out to get me." She nodded in understanding just as the elevator doors opened. She was surprised to see Dean had brought her up to the terrace and not to his apartment. "What're we doing up here?" she asked.
"I'll show you," he said. She furrowed her eyebrows but nodded. When they walked over to the couches, she noticed a huge screen opposite them. Her jaw dropped as she looked at him.
"When did you get this?" she asked, motioning to the projector. He just smiled and sat down on the daybed, patting the spot between his legs for her to sit. She did, and he grabbed one of the blankets and pulled it over their bodies. She noticed then that there was a fire going in a fancy looking pit next to the bed.
"Is this why you asked for my favorite movie?" she asked. He, again, rather than answering, picked up the remote and turned on the projector, showing that he had The Princess Bride queued up on Disney+. Just after he pressed play, he handed her a glass of wine. She hadn't even noticed the snacks and bottle of wine on the table next to them. "You're too much," she said to him with a smile and a shake of her head.
"You say that like it's a bad thing," he said, kissing her cheek with a grin.
"Well I feel a little outmatched," she said, "considering I took you bowling and you're literally fulfilling a dream date of mine I've had since high school." Dean lifted her chin and turned it so she was looking at him.
"This isn't a competition," he said. "I'm gonna love any date you ever plan as long as it means I get to spend time with you."
"Aww," she teased, "you're such a sap." Dean grinned and rolled his eyes.
"Watch your movie."
She thought at first that it would be hard to concentrate on the film when she was so close to Dean, but she underestimated how much she loved The Princess Bride. She didn't even notice Dean watch her as she mouthed the words during some of her favorite scenes or the way her eyes lit up and the corners squinted with every smile and laugh. He liked watching her so much, he almost forgot to watch the movie.
As the movie got closer to the end, Alice did find her mind started to wander. How was she going to tell Dean she wanted to do something? What did she want to do? She wasn't ready for sex yet, but she wanted more than just humping his thigh like the last time. But if she wanted him to use his mouth on her -the thought alone made her shiver, but she was able to pass it off as being cold- didn't that mean she had to do the same for him? She wasn't sure she was ready to give him a blowjob. But that was selfish, right? Didn't guys expect mutual reciprocation? Was she stupid for not being ready to give him a blowjob? Was that something she should always have been ready for? Was she making it a bigger deal that it actually was?
God, she thought to herself. Why am I like this?
The movie ended, and Dean turned off the projector. She put down her wine glass -it had been empty for a while now- and turned to face Dean. He looked at her, somewhat amused, as she straddled his waist. He didn't get to keep that amused look for very long, because she pressed her lips to his. He put one hand on her waist and the other on the back of her head. She could get drunk off his lips, and kissing him made a lot of her fears of the moment go away.
She broke her lips away from his and started kissing his cheek, jaw, and neck up to his ear. "Dean," she breathed in his ear. He hummed back. She couldn't see him, but his eyes were closed as her lips ghosted over his skin. Instead of saying anything, she took his hand and brought it down her body, prompting him to cup her clothed pussy. She sighed against his skin, and his eyes popped open. He hesitantly started rubbing her, and she gasped at the feeling.
"Do you want me to make you cum again?" he asked. She nodded, glad he got the hint without her having to say it. "What do you want me to do?" She bit her lower lip. Maybe he was going to make her say it. She really didn't want to. Why was she so bad at this? Why would he want to be with someone who was so bad at this? He must've been able to sense her nerves, because he started tracing his fingers up and down her spine. "It's okay, sweetheart," he said. "Maybe I can ask you if you want something, and you can say yes or no, okay?"
"Okay," she whispered. While he had one hand on her back, his other hand was still lightly cupping her pussy.
"Do you want to ride my thigh again?" he asked. She shook her head no, and he tsked. "Want you to use your words," he said. "Talk to me like a big girl."
Why did those words make her tummy clench?
"No," she whispered.
"Okay," he said, kissing her neck and rubbing her pussy over her shorts. "Do you want me to get you off like this? I can rub just like this-" He pressed a little harder, and she jumped at the action. "-and get you off real nice. Do you want that?"
She swallowed thickly. "No." Dean smiled and lightly bit the skin of her neck.
"Do you want me to eat you out?" he asked. "You want me to put my mouth on that pretty pussy?" She shivered and gripped his biceps in her fingers.
There it is, Dean thought to himself.
"You can say it, sweetheart," he whispered. "Just say yes or no." Her eyes squeezed shut, and she rolled her hips against his hand.
"Yes," she whispered.
"Yeah?" he pressed.
She nodded. "Yes."
Dean rolled her over so she was on her back, and it made her squeak in surprise. He smiled and kissed her softly, hoping to ease some of the nerves he could tell she still had. He kept his lips on hers while starting to untie the top she was wearing. "I want you to know," he said, kissing down her body as more and more skin was exposed, "that you can say stop whenever you want, and I'll stop."
"Okay," she whispered. She looked down at him and felt her heart leap in her throat. He wasn't looking up at her because his eyes were too focused on marveling at her body. He pushed the top open and helped her sit up to pull it off. He licked his lips when he saw she wasn't wearing a bra, and he kissed her chest, sucking one of her nipples between his teeth, and lightly bit on the flesh before releasing it. He did the same to the other, smiling at the way she was already squirming.
"I'm gonna take these off now," he said, playing with the waistband of her jean shorts.
"Okay," she whispered again. He tugged them down, kissing each inch of her thighs that was exposed. She was wearing a plain pair of black underwear, but Dean wasn't sure he had ever seen anything sexier. He looked up at her through his eyelashes to see she wasn't looking at him. Her eyes were trained up at the sky, her lower lip caught between her teeth. He nuzzled his nose against her thigh and kissed it, then tucked his thumbs in the fabric of her underwear, slowly pulling them down her legs. He tossed the underwear to the side and pushed her legs open.
Alice swore she heard him sigh when he finally opened her up to him, and it made her close her legs and put her face in her hands. "Oh my god," she muttered, "did I do something wrong? Did I mess up?"
"What?" Dean asked, flashing his eyes up to her. "What do you mean? Did you mess up having a vagina?"
"No!" she whined, moving to cover her face with her arms. She mumbled something that she knew Dean didn't catch. He leaned up and moved her arms away from her face.
"What are you talking about?" he asked. She didn't even want to look at him. She was so embarrassed. Finally, she just puffed a breath of air out past her lips.
"I shaved down there for the first time for you and I heard you sigh and I thought I did something wrong."
She immediately covered her face with her hands again, wishing internally that the bed would swallow her whole so she could get out of this moment. Dean moved her hands away again. "You shaved down there for me?" he asked, his eyebrows furrowed but his eyes showing slight amusement. She just nodded, feeling like her cheeks were never going to go back to their normal tint. "Sweetheart, you didn't have to do that." She started playing with her hands and looked down so she didn't have to look at him.
"I didn't want you to think I was gross," she mumbled. As she glanced back up at Dean, she saw he was frowning.
"Alice," he said, "you don't ever have to change anything about yourself for me. Not where you grow your hair or don't grow your hair, or what clothes you wear or don't wear, or anything like that. If you want to shave, that's okay, but do that for you, not for me."
"I just know most boys don't like hair down there," she told him. At that, a little smirk grew on his face.
"Well, maybe boys don't," he said. "But men, well, men don't care about that at all."
"You don't?" she asked, nibbling on her lip.
"Honest," he said. "I just want you to be comfortable." He paused and stroked her cheek. "Are you comfortable?" She nodded, and Dean smiled. "Okay," he whispered. He pressed a kiss to her lips, then moved back down her body to push her legs apart again so he could see all of her. He kissed her thighs gently, and she let out a shaky breath. Alice didn't know what to do with her hands, so she ended up resting them above her head and gripping her own hair that was fanned out onto the pillow. She could feel Dean's beard scratch her thighs as he moved his lips closer to her pussy. His hot breath fanned over her, and the suspense of waiting for him to do something was killing her.
"Have you ever touched yourself?" Dean suddenly asked her. Her mouth closed as she looked down at him. As soon as her eyes met his, she tilted her head back up and closed her eyes again.
"No," she whispered.
Dean wanted to take his time. This was the first time anyone touched her pussy. That was something to savor. He looked up at her and saw that her eyes were closed and her lips were already parted. God, if he could take a picture-
Was he lucky or what?
He hummed and kissed her thigh again. She waited, heart pounding, for him to do something, and she jumped when his tongue finally touched her. He pushed his tongue between her lips, sliding up and down with long, slow strokes. Her thighs moved closer to his head, but Dean held them apart with his hands. He held them close enough to him though that she could still feel the scratch of his beard against her skin. With every lick of his tongue, he moved deeper and a little faster. At one point, he moaned, and the vibration caused her lips to part as she let out a breathy, "Oh."
Dean smiled against her and moved his tongue a little faster until finally, he flicked her clit and looked up at her for her reaction. She shrieked and grabbed his head, so he stopped his movements. She didn't say anything, and her eyes were still closed. With a smile, he tentatively pressed his tongue flat against her clit, massaging it in slow circles. "Daddy," she whined, lifting her hips.
Dean's actions froze, and he looked up at her. Alice's eyes had grown wide, and she refused to look down at him. She was mortified. Did she really just say that out loud? Crap. Crap. Stupid Christine putting the daddy kink thoughts in her head. That felt like ages ago. Why was it coming to her brain now?
"Look at me," Dean said, his voice commanding. She obeyed immediately. He kept his eyes on her as he pressed his tongue against her clit again, massaging it even more slowly than he had before. She closed her eyes, and Dean growled, lightly nipping her thigh. "Eyes on daddy," he ordered. She tugged her fingers through his locks, nodding her head and looking down to meet his gaze. "Good girl," he said. "Now, what do you want?"
"I, I don't know," she whimpered, her breathing heavy. "More."
"More?" he repeated.
"I-" She whined and lifted her hips again, fighting against his arm that had loosened its grip on her. "I don't know, Dean. More."
"Can I try a finger?" he asked. Her head was hazy with pleasure, hating that he was doing so much talking and not so much doing.
"Yes," she said. "Just, please, daddy."
Her words made him growl and bring his lips back down to her core. He had to stop himself from shoving his fingers in her without warning. The things she did to him. He licked slowly across her lips again before focusing on her clit once more. While keeping pressure on her clit, he brought his pointer finger to her opening and slowly slid it in. She whimpered, and Dean noticed her thighs tense. He pulled his lips away and kissed her thigh. "Are you okay?" he asked.
"Mhm," she hummed, not looking down at him. "Just feels different." Dean nodded and pulled his finger out to drag some of her slick onto her clit. He slid his finger back in and used his thumb to rub circles on her clit. "Dean," she moaned, her grip on his hair getting tighter. He could feel her squeezing his finger, and he couldn't imagine how she would squeeze his cock once the day came. For now, he focused on easing another finger inside her. She was writhing on the bed, and he used his free arm to once again hold her down to the bed.
"Dean," she said through heavy breaths. "I think, I think I'm gonna cum."
"I can feel you getting tighter," he said, kissing across her thighs again. "Cum for daddy, sweetheart." When he curved his fingers, finding her g-spot with ease and pressing up against it, she let out a soft cry and came around his fingers. The feeling clearly caught her off guard, because she tried to scoot away from Dean's touch. He held her down and shushed her, slowing his fingers down, removing the pressure on her clit, and helping her ride out her orgasm.
When her body relaxed, Dean pulled his fingers out of her. She whined at the feeling, and he chuckled before sucking his fingers clean. She hadn't moved, and her eyes were still closed. Her cheeks were flushed, and she was opening and closing her mouth like it was dry. "Sweetheart," Dean said, lightly tugging her leg to get her attention.
"Hm?" she hummed, not opening her eyes. He couldn't hide his grin.
"How about I run you a bath?" he offered.
A bath. That sounded heavenly. She nodded but didn't bother moving from the bed, and she heard Dean laugh again. "Okay," he said. He grabbed a blanket and wrapped it around her, then lifted her off the daybed and carried her bridal style back to the elevator. When they got back into the house, he brought her to the bedroom where he laid her on the bed, then kissed her forehead. Her eyes were still closed, and he couldn't fight the chuckle that left his lips as he stroked her cheek. "I'll go run you a bath and get you some water," he said, "and then I'll help you into the tub, okay?"
"Okay," she whispered.
Alice wasn't sure how long Dean was gone, but she hardly reacted when he lifted her from the bed, carried her into the bathroom, and helped her into the tub. The water was the perfect temperature, and she moaned in relaxation. Dean felt his still hard dick twitch in his pants, but he ignored it.
In time.
Dean took off his jeans just so he could sit on the edge of the bathtub without getting them wet and rested his legs behind her back. "Want me to wash your hair?" he asked.
"Sure," she said, her voice barely above a whisper. He couldn't help but smile. Had that one orgasm really worn her out that much? It was endearing.
"Can you get your hair wet for me, sweetheart?" he asked. She nodded and tilted her head back into the tub, her eyes closed, as she wet her hair. When she sat back up, he leaned forward and pressed a kiss to her cheek. She smiled, but kept her eyes closed. He squeezed some shampoo on his hand and worked it into her hair. She hummed contently, and he could see her shoulders relax.
He couldn't stop himself.
"So you want to call me daddy?"
Alice's shoulders tensed just as fast as they had relaxed, and he only felt a little guilty. "I'm sorry," she said. "It just, it slipped out. It was weird, I'm so sorry." She put her face in her hands, and Dean's guilt increased. He slid over so he was sitting on the side of the tub and moved her hands, then lifted her chin. She looked silly with the shampooed hair sitting in a pile on top of her head. Her face was wet now, and her lower lip was jutted out in a pout. Dean couldn't help but grin and reach out to lightly pinch her bottom lip between his thumb and forefinger.
"Don't say sorry," he said. "You don't need to be sorry for something like that."
"It's not weird?" she asked. Dean licked his lips, lifted her hand, and brought it to his still somewhat stiff cock. She took in a sharp breath, and he noticed her cheeks turn red.
"That's what you did to me, Alice," he said. "And that's not even the hardest I've been tonight."
"And that's cuz I called you daddy?" she asked. His dick twitched at the name, and her lips parted at the feeling. She got flustered and let her hand drop. Dean lifted her chin again so she was looking at him.
"That's cuz you called me daddy, came on my fingers, and cuz you taste so fucking sweet," he said, bringing his lips to hers. He kissed her gently and pulled away, keeping his lips close to hers as he said, "I'm half hard every time I'm around you, baby. That's what you do to me."
Dean finished washing her hair and brought down the detachable showerhead to help her rinse it out. He grinned, thinking about how someday he'd give her an orgasm with that. But not tonight.
He got her a clean towel and helped her out of the tub, wrapping the cloth around her body. She was complacent as he helped her into the underwear she brought in her bag and the Led Zeppelin t-shirt she usually wore to bed. In the bag she brought with her was a brush, so Alice got it out and untangled her hair so she could braid it over her shoulder. She noticed him staring at her, and she cocked her head to the side. "What?" she asked. Dean blinked as if he needed to refocus, then shrugged.
"Lexi always asks me to braid her hair," he said.
"Why?" she asked. "Don't Jess and Hannah know how to braid?"
"They do," he said, a smirk growing on his face. "But I'm her favorite." She rolled her eyes with a smile, and Dean changed into a clean shirt and joined her on the bed. She undid her braid and patted the bed behind her. He raised his eyebrows at her.
"C'mon," she said. "Let me teach you." He still looked skeptical. "Wasn't it you who said that if you're going to teach me stuff, I should be teaching you something too?"
At this, Dean laughed and obliged. Alice handed him the hairbrush, and he brushed out her long locks, pushing it to the side a few times so he could kiss her neck, which always resulted in her giggling until she made him focus again. "Should I teach you a normal braid or a french braid?" she asked.
"I think I can handle a normal braid without you teaching me," he said. Now it was her turn to raise her eyebrows.
"Prove it," she said.
Yeah, he needed help.
The pair spent at least twenty minutes in bed as Dean tried to braid her hair. He managed a regular braid after only two tries, but once she started to teach him the french braid, he got easily frustrated and kept taking it all apart and starting over whenever he got confused. When he finally gave up, she did the french braid herself and tied it off with the elastic she had around her wrist. "Don't worry," she teased, "we'll keep practicing. I wouldn't want you to let Lexi down."
Dean chuckled, and they both laid down under the covers. She turned on her side so she was facing him. He noticed the way she was nibbling on her upper lip. "What's on your mind?" he asked. She released her lip and sighed.
She had been so blissed out after everything happened that she hadn't thought about the reciprocity thing she had been so worried about earlier until she was in the bathtub. "Don't you ever want me to do anything for you?" she asked. Jo's words were running through her head again. "I know we haven't done a lot, but I, I feel bad that you keep doing things for me, and I'm not doing anything for you."
Dean turned so he was also on his side facing her, and she noticed the crease between his eyebrows again. She reached out and smoothed it out. "Don't think about what she said," he told her, like he was reading her mind. "I told you. I'm happy doing this at your pace."
"I just don't want to be the only one getting something out of this-" She hesitated.
What was this?
Dean had called her "his girl" at the meeting, but what did that mean? Was it too soon to put a label on this? They had been on two official dates, plus what had just happened on the roof. That wasn't counting the random time he showed up at her front door or the times she went to family dinner with him.
"Alice?" he said. It sounded like he had said her name a few times. She looked at him. "I'm not just doing this to get my dick wet, okay?" he said, referring to what Jo had said earlier. "Remember what I told you the other day? I like you." He stroked her cheek and brushed his thumb across her cheekbone. "And I'd like you to be my girlfriend, if that's something you'd like to be."
Alice tried to control the giddy look on her face, but Dean could see through her. Still, he decided not to embarrass her and just stayed quiet. "Yeah," she whispered, giving him a short nod. "I'd like that." He leaned over and pressed a soft kiss to her lips. "Still," she said when he pulled away, "I'd like to do something for you sometime. You'll just, you'll have to teach me."
When Alice got to school on Monday, she stopped in the main office to talk to the secretary, Joy. "Hey," she said, giving the lady a smile. "Remember that man who came a few weeks ago? He brought me flowers? Signed in as Dean Winchester?"
"Mhm," Joy hummed, her smile widening. "Handsome guy."
"Yeah," Alice said. "Um, he might try and stop by again. If he does, please don't let him in."
Joy's face changed to an expression of concern. "Is he dangerous?"
"No, no, it's not that," she said. "He just-" She hesitated, then sighed. "We're in the middle of a fight, and I know he might try and come talk to me. I'm just not ready." Joy nodded in understanding and gave Alice a sympathetic smile. Alice thanked her and headed off to her classroom.
There were three sets of doors visitors had to go through before they got into the building. First they had to buzz into the main building and state their business to the camera, then they had to buzz into the office and sign in before they could finally be buzzed into the school itself. Realistically, all a person had to do was say the right thing, and no one would bat an eye. Alice was sure Dean could say, "I'm Alice Berkley's boyfriend, and she's expecting me for a visit," and Joy wouldn't think twice. It wasn't that Joy was dumb at all. Dean was charming and didn't appear threatening, especially since he'd probably been seen around the school before picking up Lexi. If he didn't set off any of the metal detectors, he was just a man with a kind smile and a bouquet of flowers.
Alice made sure Joy knew everyday for over a week not to let Dean in, and Thomas agreed to send her kids off again at the end of the day. She definitely owed him a few favors with everything he had done for her thus far that year.
Over a week had gone by since the party, but Alice still hadn't contacted Dean. He hadn't reached out either. She had no idea if he had been coming to pick Lexi up or not, but he hadn't been texting her. Just like their last fight, she wondered if they were done. Even though she knew this time, she needed to be the one to reach out, she couldn't get herself to do it. Every time she considered picking up her phone, she would picture Dean throwing a punch at Jaden, and she would set it down again.
She was sitting at her desk, looking over the kids' spelling tests, when there was a knock at her door frame. She looked up and saw Thomas. "Hi," she said with a small smile and a sigh. "Thanks for taking the kids out again."
He chuckled. "You don't have to thank me every time."
"I know, I know," she said. "I just appreciate it." Thomas nodded and walked into the room, propping himself up against one of the tables.
"How're you doing?" he asked.
"What do you mean?" she asked. "I'm fine."
"Ah, ah," he said, holding his hand up. "Remember, my daughter's your age. I've heard the I'm fine lie enough to sniff it out." Alice scoffed and shook her head.
"Just petty boyfriend troubles," she said, "and I'm not good at confrontation."
"You plan on hiding in here forever?" he asked.
"Can I?" she asked with a sad smile.
He scoffed. "I'm afraid not."
Alice slammed her head against the keyboard which made Thomas laugh again. "Why didn't you ever set me up with your son?" Alice asked him, looking up at him.
"Ah, that would be because he's gay," Thomas said.
"Right," she said with a nod. "Small detail."
Thomas smiled. "So how'd the fella do you wrong?"
She sighed. "He's just a jealous guy. I'm trying to go easy on him. He hasn't had the greatest life, and I think he's just afraid of losing people. In fact, I know he is. I just wish he could express himself in a way that wasn't so aggressive." Quickly, she added, "He doesn't hit me or anything. He never would. He just-" She sighed again. "He's really complicated."
"Well," Thomas said, standing up from the table he was perched on and walking over to her. He clapped her on the shoulder. "If true love was easy, we'd all have it."
Those were the words that kept running through Alice's head that night. If true love was easy, we'd all have it. If this was what love was like, she wasn't sure she wanted it. Being with Dean was fun, and most of the time he was sweet and caring, but the few times that he wasn't were what she didn't want. Was she not deserving of a healthy, normal relationship? Had Christine been right all along? Was Dean textbook toxic? Had she just been blind to his charm? Was it inevitable that he would end up hurting her?
On Tuesday, Alice was sitting in her classroom after school again when there was another knock at her door. She looked up, expecting it to be Thomas. Instead, it was Jess and Lexi. "Hey," Jess said, giving Alice a smile.
She sighed. "Hey."
"Don't look so thrilled to see me," Jess teased.
"I'm sorry, I'm sorry," she said, standing up and walking over to Jess. She pulled her in for a hug.
"Lexi, you wanna go play while me and Ms. Alice talk?" Jess asked her.
"Can't I listen to big girl talk?" she pouted.
"Mm, not today, sweetie," Jess said, kissing her daughter on the head.
"You can go grab your chromebook if you want," Alice offered. "Watch some videos." Lexi nodded and did as Alice suggested. Alice knew she'd grab headphones, which meant she could talk to Jess without any fear of Lexi overhearing.
"Talk to me," Jess urged her, pulling up one of the adult-sized chairs to sit beside Alice. "I only heard that Bobby had to pull Dean off of Jaden."
Alice explained what had led up to Dean's outburst, and Jess sighed when she finished. "I'm sorry," she said. "I get why you're mad."
Alice sighed and asked the question she had been mulling over for a while. "Was he like this with Lisa?" Jess looked at her and sighed as well.
"No," she said. "Not really."
"Then why is he like this with me?" she huffed. "I don't understand."
"Well, you're not Lisa," she said. "He's not going to treat you like you are."
"But why does he have to baby me?" she asked. "If it's because of our age difference-" She hesitated. "-I need to know if that's something he's ever going to get over. Because I can't do this forever."
"He just wants to keep you safe," Jess said. "Try to go easy on him."
"I won't let him keep beating people up to protect me," she said, putting quotes around the last two words. "I'm done with men who think violence is essential in a relationship." Jess was quiet, and Alice ran her hands through her hair in frustration. "Jess, do you think he'll ever hurt me?" she whispered.
"No," Jess said without hesitation. "Never. Don't think like that."
"I can't help it," Alice sighed. "I'm so-" She paused. "Dean knows how bad my last relationship was, but he still does the things he does. I don't want to be afraid of him, but-"
"You should talk to him about this," Jess said. "If he knew you felt this way-"
"What about that fight we had at your house?" she said. "It was over the same thing. The whole Brent thing, remember? It was the same thing. I told him I didn't like how possessive he was, but it didn't phase him. So he knows, but he doesn't care."
"I'm sure he cares," Jess said. "Dean's just-"
"Complicated," she finished. "I know."
"I'm not saying how he acts is justifiable," Jess said.
"No, I know," Alice said. With another sigh, she added, "I just want him to understand what he's done and why I feel how I do and say he's sorry."
"I know," Jess said. "I understand."
-
Dean was alone at home taking a sip of yet another glass of whiskey when his phone rang. The sun had already set, but it wasn't too late yet. Still, he was a little surprised to see it was Jess. Jess didn't call him very often. If he did, it was almost always related to Lexi. He picked up quickly. "Hey," he said. "Is everything okay?"
"Depends on your definition," Jess said on the other end.
"What does that mean?" Dean asked, leaning back on the couch. He pinched the bridge of his nose. He knew this tone of voice. He was in for a lecture.
"I just saw Alice," she said. He sat up a little straighter.
"Where?" he asked.
"I picked Lexi up," she said. "They let me in."
"Of course they did," he muttered. "She must have me on some no-fly list."
"Because you scared her, Dean," Jess said. "She's not ready to face you yet."
"God, I know I messed up," he said with a heavy sigh. "I'm just working on how I can make it better."
"I get it," Jess said. "Just know that I think she's ready to talk to you, but you're probably going to have to be the one to initiate it."
When Dean got off the phone with Jess, he finished off his glass of whiskey and sighed. He was sorry. He really was. All he needed was a big, grand gesture to prove it to her.
And so, the wheels started turning.
-
On Friday, Alice got home after school and checked her mail. She didn't have anything in the box, but there was a package with her name on it on the ground. She furrowed her eyebrows and picked it up, searching for the address label. There was none. While she knew that probably should've raised a few red flags, she took the box anyway and headed up stairs.
She crossed into the threshold and dropped her keys and the box on the counter. She slowly started to open it and found a black jumpsuit and a pair of wedged sandals. There was a handwritten note on top of the shoes:
I know you're mad at me, but please be ready by 7:00. I swear I'll make it worth your while x
Alice pressed her lips into a tight line and dropped the note. Was she ready for whatever Dean had planned? Was she ready to face him again? The reality was, she couldn't ignore him forever.
When 7:00 rolled around, Alice was ready. Dean buzzed into her apartment, and she let him in. She paced back and forth, unable to stop herself from chewing on her thumbnail. Why was she so nervous? This was her boyfriend. This was Dean.
Dean knocked at her door, and she took a deep breath before opening it. He looked as handsome as ever: black slacks and a white button-up. In his hands was a bouquet of roses. "Hi," he said, giving her a smile.
"Hi," she said.
"These are for you," he said, handing her the bouquet.
"Thank you," she whispered. "They're beautiful." She stepped back into the apartment to put the flowers on the counter, then turned back to face him.
"Ready?" she said.
"Mhm," he hummed. He stuck his arm out for her to take, and she did. It was a little chillier outside than she expected, but she knew they would be in the car so she didn't really mind. Dean opened the door to the Impala for her, and she thanked him and slid inside. While she would normally slide as close to Dean as she could in the front bench seat, she stayed respectfully on her side.
Dean noticed but stayed silent, though his heart did break at the sight.
"So," Alice said, clearing her throat as Dean put the car in drive, "where are we going?"
"Come on," he teased. "It's always a surprise."
"Right," she whispered, staring out the windshield. She fiddled with her hands on her lap, and Dean sighed as quietly as he could.
This would be okay. They would be okay.
Dean turned on his music, and Alice's eyebrows furrowed when she recognized the tune. "Is this Ben Platt?" she asked. She leaned forward and turned up the volume slightly, hoping to catch the words of the tune.
You say there's so much you don't know. You need to go and find yourself. You say you'd rather be alone. Cuz you think you won't find it tied to someone else.
"Yeah," Dean said, a small smile growing on his face. "I thought I'd make a cassette."
"Of Ben Platt songs?" she asked. Dean shrugged but didn't say anything. Alice looked over at him and studied his profile. The sun had already set, so she could only make out little things, like his sparkling eyes and the slight glisten of his lips after he ran his tongue across them. The length of his stubble made her want to reach out and touch him, just like she always did. She held back though and forced herself to stare out the windshield again.
Alice was surprised when they pulled up to Dean's apartment. Still, she got out of the car when Dean opened the door for her. He put his arm around her waist and smiled to himself when she didn't jump away. "You gonna tell me what we're doing yet?" she asked as they walked towards the elevator. She gave Derek a smile as they passed, which he returned. As they waited for the elevator, Dean stood in front of her.
"I want you to see how much I care about you," he said, "and that I feel terrible about what happened at the party." Alice hung her head, but Dean lifted her chin. "I do," he pressed.
"'S okay," she mumbled.
"No, it's not," he said. The elevator dinged, and Dean put his hand on the small of her back and guided her in. "So I thought I would bring in a little surprise."
"Bring in?" she repeated.
"Mhm," he hummed. He pressed the button to the rooftop terrace and swiped his card to get access. She looked at him with raised eyebrows, but he just smiled.
When the doors opened, Alice could hear another familiar tune playing. They rounded the corner, and she froze at the sight in front of her. It was a small stage -nothing too fancy- and a group of people on stage with one man standing front and center. "Dean," she whispered, unable to get her feet to move. "Is that-"
"Welcome to your personal Ben Platt concert," he whispered in her ear. She looked up at him with a dropped jaw before a guitar started to play on the stage. She laughed in disbelief and ran over to the stage.
Ben smiled at her. "Hey, Alice," he said into the microphone. "How's it going?"
"It's-" She laughed again. "It's great now!"
He laughed as well. "Alright, well let's do this."
The concert was so great. Ben would stop in between songs to chat for a while, occasionally asking if she had any requests. Every time, she just told him to play whatever he was planning next. She didn't stand up and dance at all, but she bounced in her seat and sang along to every word to every song. Ben was an amazing performer, and for that whole time, she forgot why she had ever been mad at Dean in the first place.
When Ben started to play the last song, Dean stood up from the couch and held his hand out to her. "Dance with me," he said.
Just like that, her perfect bubble popped, and she remembered why they were fighting. Still, she nodded and took his hand.
Dean wrapped an arm around her waist and held her close to his body. He laced his fingers with hers, and she rested her head on his chest and her free arm over his shoulder, playing with the hairs at the nape of his neck. Ben's voice filled the space around them, and Alice closed her eyes, trying to stay in the moment and not overthink everything that had happened the past few days.
I may not be wise, and I won't save the day, but look in my eyes, and know I'll always stay. And I won't run away.
As soon as Ben finished the song, Alice broke out into cheers and applause. Ben laughed and put his hands together, bowing in a silent thank you. Alice looked at Dean. "Could you go get me some water?" she asked him. "I want to go talk to Ben."
He smiled. "Course, sweetheart." He kissed the top of her head, and she whispered a thank you. As soon as he was out of earshot, she walked over to Ben.
"Hi," she said. "It's so great to meet you. You were incredible."
"Thank you," Ben said. He offered her a hug, which she accepted. She tucked a piece of hair behind her ear and looked behind her to make sure Dean hadn't come back yet.
"Can I ask you something?" she whispered.
"Sure," Ben said.
"You don't know Dean, do you?" she asked. He shook his head no. "So did he just, like, pay you a lot to be here?" Ben hesitated. "I won't be offended or anything. I'm just curious." Her eyes grew wide for a moment. "Oh my god, did he threaten you?"
"No, no," Ben laughed. "No. You were right the first time. He offered a pretty big hunk of money."
Alice nodded and thanked him again just as Dean brought her some water. Within the hour, Ben and his band were all packed up, and Alice and Dean were alone at the apartment. They stayed on the terrace, cuddled up with each other, staring at the sky. Alice didn't know what to say to him. What he had done was sweet, but it didn't solve the real problem at hand. She needed to get her feelings out, and she wasn't sure Dean was going to be the one to say anything.
Just when she got up the nerve to say something, Dean turned her chin so she was looking at him. He leaned forward and tried to kiss her, but she pulled away, and he hung his head and sighed. "How are you still mad at me?" he asked. Her lips parted in shock as she shook her head and stood up from the couch.
"I knew it!" she said.
"Knew what?" Dean asked.
"You think the normal way to make up after a fight is to do something like this?" she said. "Bribing my favorite artist into performing for me? That's not normal, Dean!"
"God, again with the normal thing," Dean said with a slight roll of his eyes.
"You're really going to roll your eyes at me?" she said.
"Are you saying you didn't like the concert?" he asked, folding his arms across his chest.
"I'm not saying I didn't like it," she huffed. "It was a private concert by Ben Platt, of course I liked it."
"Then I don't understand-"
"Exactly!" she shouted. "You don't understand! You don't understand how a normal relationship works! You think you can solve every problem with money or, or sex or murder! It's just, it's too much, Dean."
"So what are you trying to say?" he asked.
"Nothing!" she said. "I'm not-" She groaned and threw her hands in the air. "I just wish you could be normal! I wish this could be normal! I wish-" She sighed. "I just wish I could be in a relationship that made sense."
"So what, are we breaking up?" he said.
"We're-" She rubbed her forehead and hesitated. "We're taking a break, okay? I need a break. I can't do this right now." She grabbed her bag and started to walk to the elevator.
"Alice," Dean said. "Come on." Alice didn't say anything as the elevator opened. She knew if he really wanted to follow her, he would. And as the doors closed behind her, she realized he didn't.
Tears started to fall from her eyes as she called an Uber. It was there within five minutes. In that time, Dean never came down to talk to her.
Did she really just walk away from that relationship?
Dean rubbed his face with his hand in frustration. Okay. So that didn't work. He was running through every moment of the night. Alice seemed to have been enjoying herself. He was sure it was all okay. What had he missed? Now, was it his place to reach out to her again? Was the ball back in her court?
Did he really just let her walk away from that relationship?
----- ----- ----- -----
A/N - when I wrote this I had just watched Ben Platt’s Netflix concert (it’s so good don’t even start with me) so if ya’ll don’t listen to him you’re missing out for real
warnings - language, thigh riding, Dean is so sweet your teeth will hurt
additional notes at the end
(previous)
On Saturday, Alice was excited to get breakfast with Christine. Even though she knew Christine would tease her endlessly about her date, she also knew she'd give her so much support. Christine was very vocal about how much she hated Greg, so she had been ready for Alice to jump back on the dating horse ever since she pulled back into Lawrence. She knew Christine would be over the moon that Dean was as amazing as he was.
Alice beat Christine to the cafe, but as soon as Christine walked in, she all but ran to the booth. She slid in and waved the waitress over. "Hey AJ," she said. "We'll have our usual." AJ laughed at Christine's assertiveness before nodding and leaving the pair. Christine put her elbows on the table and her chin in her hands. "Tell me all about him."
And she did.
Alice raved about the flowers, the dinner, and the drinks they had after. She decided not to spare any details, sharing how respectful Dean was when she didn't want to go any farther but also how badly she wanted to keep kissing him forever. "Wow," Christine breathed out, smiling dreamily. "He sounds perfect. What does he look like?"
"Mm," she hummed. "Tall, but not too tall. Muscular, but not too muscular. Sharp jaw. Gorgeous eyes. The perfect amount of stubble on his face."
"How old is he?" Christine asked.
Ah yes. The question she was dreading the most.
"He's a little older," she said, sipping her coffee.
"How much older is a little?" Christine asked. She was on the verge of smirking, able to see right through her friend. Alice didn't say anything, just kept her mouth on her coffee mug. "Alice," Christine pressed. "How old is this guy?"
Alice sighed. "41. I think."
"41!" Christine repeated. "Alice, you're 22."
"I know how old I am," she said. "It's not like he's a grandpa or anything." Christine laughed. "What?" Alice said. "I like him. He's nice, and he's hot! And he's mature, and he has a real, adult job, and, and he respects me." She shrugged. "Plus -I don't know- he takes care of me. We're not even together-together, but it's like I already know he'd protect me if I needed it. Not that I would, but-"
"Dude," Christine said before sipping her own coffee. She put her mug down, leaned back in her chair, and folded her arms across her chest. "You have a daddy kink."
"What?" Alice almost hissed, getting closer to Christine as if to tell her to quiet her voice. "I do not!"
"You so do," Christine laughed, sitting up in her chair again and putting her elbows on the table. "You love this age difference. You want him to take care of you, and-" She laughed again. "God! You're his little sub already. I'm so ready for this guy to pop your cherry."
"Why are we friends?" Alice asked, rolling her eyes and drinking her coffee again to hide her blush.
"You'll tell me all about it, right?" Christine asked. "Like how big he is? And how much of a dom he is? And-"
"I'm not gonna tell you about it because today is the last time I'm ever going to hang out with you."
"Shut up," Christine said with a grin. "You love me." Alice rolled her eyes and took a bite of her eggs. "And he was nice when you told him you were a virgin?"
She nodded. "Yeah. He felt bad for asking. Said it wasn't his business." The corners of Christine's mouth turned slightly as she nodded with a quick shrug.
"He's not wrong," she said.
"I don't even know why I said anything," Alice said. "It just came out. I was so flustered."
"Well, you've had a weird week," Christine said. "I'm surprised you're handling it all as well as you are."
Alice shrugged. "You know me. I've been through worse."
-
Dean walked into Sam's house with a smile on his face. Hannah had an event through work that evening, so they pushed family dinner to Sunday. Still, Dean thought he'd stop by and visit his brother. "Anybody home?" he asked.
"Living room!" Sam called. Dean walked through the house and plopped on the couch beside his brother.
"Where're Jess and Lex?" he asked.
"Shopping I think," Sam said. "Told me it's a girls' day. I'm not allowed to know." Dean laughed, and Sam looked away from the TV and at Dean with furrowed eyebrows. "What's got you so happy?" Before Dean could even answer, Sam's eyes grew wide in realization. "Your date with Alice," he said. "You're telling me that's got you like this?"
"It might be," Dean said with a shrug, trying to appear casual. Sam shoved Dean and turned his body to face him.
"I never thought you'd actually tap my daughter's teacher," he said with a laugh.
Dean shook his head. "I didn't hook up with her." Sam looked confused. "No, we went out for dinner and had some drinks back at her house."
"And you didn't sleep with her?" Sam asked.
Dean scoffed. "Is that all you think I do?"
"Pretty much, yeah," Sam said. "I thought you weren't one for the dating game."
"I went on the date for Lexi," Dean said sarcastically.
Sam rolled his eyes. "So you didn't even try to sleep with her?"
"Well, I wouldn't say that," Dean said, folding his arms across his chest. "I started to, you know-" Sam nodded and waved his hand so that Dean wouldn't explain any further. "She freaked out. Told me she's a virgin."
"A virgin?" Sam repeated. Dean nodded. "I thought you only liked experienced girls."
"God, shut up," Dean said with a roll of his eyes.
"You think you'll see her again?" Sam asked. Dean licked his lips with a small nod.
"I'd like to," he said. Sam was quiet for a moment. Dean could tell he was thinking something but holding back. "Spit it out," Dean said. Sam looked at his brother, then sighed.
"What's your endgame here?" Sam asked.
"What's that supposed to mean?" Dean asked.
"This can't just be one of your games," Sam said. "She's so young, man. She's got a whole life ahead of her. And whatever happens is gonna affect all of us. So what're you gonna do? Take her on a few dates? Show her what a good time is? Break her heart in the end?"
"Jesus Christ, Sam," Dean said. "You really think that little of me?" Sam shrugged. "Frankly, what I choose to do with her is none of your business," Dean said.
"Whatever man," Sam said, holding his hands up defensively. "Just thought I'd put the thought in your head."
It wasn't that Dean hadn't already been thinking all of that. He didn't know what his endgame was, but what people did? Did everyone go into meeting a person planning out their whole future? So he took her on a date. So he wanted to see her again. Maybe they wouldn't be forever, but what was wrong with living now? He didn't want to play a game of chase that just ended in him fucking her. Not anymore. Like he'd always said, if he wanted his dick sucked or a girl to fuck, he had numbers on speed dial. Hell, Amara, Jo, Bela, and Anna were practically on standby. He liked Alice. This was more than just adding a girl to his black book.
What that more was, he just wasn't sure yet.
The day wore on uneventfully. When the sun set, Dean was alone in his penthouse, sitting in bed and watching TV. He had this weird desire to text Alice, like his phone was burning a hole in his pocket. Was it too early to text her? He had only seen her yesterday. Should he step back?
He felt like a teenage boy. This was stupid.
Alice jumped when her phone buzzed on the bed beside her. She picked it up and held back a wide smile.
Dean: What are you up to?
She bit her lip and swiped to respond: Just in bed watching a movie
He texted back just as fast: What movie?
Her thumbs hovered over the screen. She could lie and say something cool, like an action flick or even a horror. Instead, she said, You're gonna laugh at me
Dean: Swear I won't
She smiled and decided to tell the truth: Tangled
Again, Dean was quick to respond: The Disney movie?
She pouted and wrote, You swore you wouldn't laugh
Dean: I'm not laughing!
Alice: It's a good movie
Dean: I'm glad you're enjoying yourself
This made her smile. I am, she wrote back. The only thing that could make it better is ice cream
Dean: Yeah? What's your favorite?
She laughed. Hmmm. That's a heavy question, Dean
Dean: Is it?
Alice: Yes. Yes it is. It varies from day to day. Right now I think it's Ben and Jerry's Cinnamon Buns. Sometimes it's Milk and Cookies
Dean: Hm. I've never had that
She furrowed her eyebrows. Those flavors or Ben and Jerry's? She grinned, then added, Or ice cream in general?
She could imagine Dean rolling his eyes. Ha ha, he sent back, sarcasm evident in the text. Ben and Jerry's
Her jaw almost dropped. What? That's crazy! It's the superior ice cream brand
Dean: Okay okay! I'll have to give it a try
She held down the text so she could react with a heart, then locked her phone and put it back down, resuming play on Tangled. After a few minutes went by, she got bored. She decided to grab a facemask from her bathroom and put it on and maybe do her nails. It had been a while since she had a nice, relaxing night. She picked one of her favorite clay masks and applied it, then picked a baby pink shade for her nails. When she pressed play on the movie again, Rapunzel was leaving her tower for the first time with Flynn. By the time they got to the Snuggly Duckling, her apartment's buzzer went off. She furrowed her eyebrows, paused her movie, and walked over to the intercom, trying not to touch anything with her wet nails. "Hello?" she said, pressing the speaker button.
"Hey, sweetheart. It's Dean. I come bearing gifts. Can I come up?"
Crap, she thought to herself as she remembered she still had her mask on. It hadn't dried yet, but there was no way she'd let Dean see her that way. She'd have to rinse the mask off before he got upstairs. "Yeah!" she said through the intercom. "Come on up!"
She buzzed him in and ran as quickly as she could to the bathroom. The mask was mint green, and she was bummed that she didn't get to have it long enough to do its job refreshing her skin. But there was no time to dwell. She washed the mask off -messing up her nails in the process- and patted her skin dry just as she heard the knock at her door. She ran over and whipped the door open. "Hi!" she said with a smile.
"Hey," Dean said. "I brought you something." She cocked her head to the side, and he lifted the grocery bag he was carrying. She was able to see through the plastic, and she smiled widely.
"Ice cream?" she said. He nodded, and she let him inside and closed the door behind him. He went into the kitchen and pulled out one pint of Cinnamon Buns and one pint of Milk and Cookies. "You didn't have to do that," she said, though she was so glad he did.
"I know," Dean said, placing a kiss on her forehead. When he pulled away, she noticed his eyebrows had furrowed.
"What?" she said. A smirk grew on Dean's face as he reached up and wiped his thumb on her forehead. He showed her his thumb which had a little smudge of green on it. "Crap," she muttered, putting her hand on her forehead.
Served her right for acting too hastily.
Dean laughed and put the ice cream in the fridge, then followed her into the bathroom where she went to wipe her face off again.
"What is it?" Dean asked her, leaning up against the doorframe as he watched her.
"I was doing a facemask," she said with a slight pout.
"Well why didn't you leave it on?" he asked.
"I looked weird!" she said. "My face was green like a martian."
"Your facemasks are green?" he asked.
"One of my facemasks is green," she said. "I have black ones and orange ones and clear ones and purple ones." Dean raised his eyebrows, and she just laughed and opened one of the drawers so she could lay out all of her facemasks. Dean whistled lowly before chuckling.
"What's the point of all these?" he asked.
"They do different things," she said. "Some of them are supposed to help your blackheads, and some are supposed to refresh you or make you feel cleaner. I think they're just fun." She looked up at him and bit her lower lip.
"What's that look for?" he asked, folding his arms across his chest.
"You could do a facemask with me," she said, putting her hands behind her back.
Dean laughed. "Yeah. No way."
"Please?" she whined. "I think you'll like it. It'll make you feel so relaxed."
No. He would stand his ground. He wasn't going to let her-
"Please?" she said again. And then she had the audacity to flutter her eyelashes, and Dean jutted his jaw out and sighed.
"You're lucky you're cute," he said. Her smile broke across her face and she stood on her tiptoes to kiss his cheek.
And no. He did not blush.
"Alright," he said, clearing his throat. "Which one are you giving me?"
She picked out a clear sheet mask for him and decided to grab one for herself too since she wasn't able to let the clay one do its job. She opened the package and pursed her lips at Dean. "You're too tall," she said. "I can't put it on you when you're, like, half a foot taller than me." Dean grinned then licked his lips and moved to his knees in front of her. He was eye level with her stomach, and she couldn't help the way she shivered.
"Is this alright, sweetheart?" Dean asked, lightly squeezing her hips. She giggled nervously and jumped out of his touch.
"Mhm," she hummed. "That's better."
She forced herself to focus as she unfolded the mask and laid it on his face, making sure the eye holes and mouth hole were where they needed to be. She tried not to burst out laughing. She was sure the last thing this tough, rugged, 40-year-old man ever expected he would be doing on his knees in front of a girl was applying a face mask. "Are you laughing at me?" he asked, attempting a serious expression under the mask. She bit her lip and shook her head no. Dean stood up from the ground and took a step towards her. Her back immediately hit the wall. "Nowhere to run," he said. She licked her lips and put her hand on his chest.
"Well," she said, "you can't kiss me with the mask on. And that stays on for twenty minutes." Dean scoffed, and she gently pushed him away so she could sneak past him and put her own facemask on. Dean stood behind her and wrapped his arms around her waist. They were standing in front of the mirror, and she couldn't help but grab her phone from the waistband of her sleep shorts. She opened up Snapchat and put one hand under her chin, snapping a picture of her and Dean. He laughed as she put a filter over it that said my face at 9:56 PM. She saved the picture and posted it to her story before she and Dean moved away from the mirror and went to sit on her bed in front of the TV.
"I'll grab the ice cream," Dean said.
"Spoons are in the drawer to the left of the sink," she told him. Dean came back with the two ice cream pints and spoons, handing her one of each. She looked and saw that he handed her Cinnamon Buns. She opened it at the same time that Dean opened his. She put the ice cream on the side table and got her phone out again.
"What're you doing?" Dean asked as he started to dig his spoon into the ice cream.
"I have to film this," she said. "This is a historic moment."
"It's ice cream."
"It's Ben and Jerry's!" she said back. "It's scientifically better than any other ice cream."
"Oh really?" Dean said patronizingly, cocking his head to the side.
"Yes," she said with a firm nod. "Ben-" Dean raised his eyebrows. "-co-creator of Ben and Jerry's," she clarified, "can't smell. And smell affects taste, so they put bigger chunks in it so he can at least feel their texture since he can't taste them."
Dean laughed. "Why do you know that?"
"Jeff Goldblum has a show on Disney+ and he talked about it on an episode," she said. Dean raised his eyebrows again and she rolled her eyes. "I like Jeff Goldblum and I like ice cream. Sue me. Now let me record your first bite."
"You know," Dean said, "as good as this might be, it's got nothing on, like, authentic gelato. You know that right?"
"Shut up and eat your ice cream."
Dean took his first bite of Milk and Cookies while she pointed her camera at him. He struggled to make sure his mask didn't slide off as he shoveled his spoon in his mouth. She looked at him expectantly, and Dean shrugged. "I've had better." Alice gasped and gave Dean a shove, still holding record on her phone. Dean laughed and pulled her onto his lap, and her finger slipped off the screen, promptly stopping the video. Her phone fell to the side as she straddled Dean's waist and played with the hairs at the nape of his neck. She wanted to kiss him, but she was not going to allow him to take the mask off. It would go against everything she had told him earlier. So, she adjusted herself on his lap and turned so she was facing the TV.
Dean held back a groan as she wiggled on his lap. He held her hips and watched as she picked up her phone, saved the video, and posted it to her story. She grabbed the ice cream she abandoned and took some of it with her spoon. They switched between ice cream flavors, sometimes feeding a spoonful to each other. After a while, they weren't hungry anymore, so Dean moved her off his lap and went to the kitchen to put the ice cream away before it started to melt.
It was time to take their masks off, so they went to the bathroom and took them off, throwing them in the trash. She rinsed her face off, patted it dry with a towel, and looked in the mirror to see Dean staring at her. "Why're you looking at me like that?" she asked, adjusting her shirt a bit.
"Sorry," Dean said, forcing his eyes to focus on hers again. "Just looking at your pajamas. They're different than the ones you wore when I was last here."
She chuckled. "Well yeah," she said. "I have lots of pajamas. Don't you?" Dean smirked and ruffled his hand through his hair.
"Well, I usually sleep in my boxers," he said. "So I guess I have a lot of pajamas, too." He could tell his words made her flustered by the way she blushed and looked away.
"Pajama sets are like a weakness for me," she admitted, quickly shifting the subject. "I buy them way too much."
Dean hummed in understanding, pulled his own mask off and rinsed his face, then dried it off before looking at her with a smile. "How do I look?" he asked.
"Refreshed," she teased. "You're glowing."
Dean's smile widened, and he wrapped his arms around her waist, pulling her close to him. "So," he asked, his lips so close they were tickling hers, "do I get that kiss now?" She giggled and put her hands on his cheeks.
"Mm, that is what I said, isn't it?" she said. Dean scoffed and leaned down to press his lips to hers. She kissed him back, letting her thumbs brush across his smooth skin. Dean surprised her by lifting her up and sitting her on the bathroom counter. She hooked her ankles around his waist and slid her hands to the back of his head, holding him closer to her. His hands moved under the back of her shirt, resting his palms on the small of her back. His hands were rough, covered in calluses he must've accumulated over the years. She wondered how. Office work didn't usually result in beaten hands.
And why was she thinking about this right now?
When they parted, she let her forehead rest against his. He chuckled and pecked her lips once more before stepping back so she could jump off the counter. "Alright," he said, "I gotta know how that movie ends."
They ended up back in bed, Dean's arm wrapped around her, holding her close to him. She had her head rested on his collarbone, and he kept trailing his fingers up and down her arm. She absolutely hated how badly she wanted to kiss him. She could hardly control the urge she had to hop on his lap and suck his face like her life depended on it. She hadn't even realized she had been wiggling so much until Dean squeezed her hip. "Why're you so squirmy?" he teased. She looked up at him as he ran his tongue across his lower lip.
She took a deep breath and sat up, straddling his waist. His hands immediately landed on her hips, and the playful glint in his eyes had vanished. She kept her hands braced on his shoulders as she leaned forward and kissed him. She slid her tongue past his lips, and he moaned and moved one hand to the back of her head. She didn't notice the way her hips had begun grinding against his, but she did notice the moan that escaped Dean's lips. He pulled away from her and started kissing down her neck.
His hand that was resting on her waist slid up slowly, palming her breast over her shirt. She let out a shaky breath and rolled her hips against his again. "Sweetheart," Dean said, fighting back another moan. "Ah fuck, you're killing me."
"Sorry," she whispered, stilling her hips and resting her forehead on his shoulder. "I just, I wasn't thinking." She let out a surprised gasp that quickly turned into a moan when Dean pinched her nipple through her shirt. He knew what was going on. Exactly what was going on, and he was sure she knew it too. She was just too embarrassed to say it.
Dean started kissing her neck again. "It's okay," he muttered. He grabbed one of her thighs and moved it to rest in between his legs so she was straddling his thigh instead of his hips. She wasn't meeting his eyes, so he lifted her chin to make her look at him. Instead of saying anything, he pressed his lips to hers. He bit her lower lip, drawing out a soft whimper. He started kissing her neck and tugged at the hem of her shirt. "Can I take this off?" he whispered. Dean noticed her grip on his shoulders tightened. He moved his face from her neck so he could look at her again. "You remember what I said yesterday?" he asked. "I don't want you to be nervous around me, and I never want to make you uncomfortable. You can say no. You can always say no to me."
Alice swallowed nervously, and Dean stroked her cheek. His lips curved up in a small smile. "I can just see you're a little-" He hesitated with a chuckle. "-frustrated." The apples of her cheeks turned pink, and she hung her head again. He lifted her chin. "You can say no," he said. She took a deep breath in through her nose and out through her lips.
"Can you take yours off first?" she asked. She didn't want to be the only one without some clothes on, and even though she knew showing him her breasts was a lot different than him showing off his pecs, she didn't want to be alone. Luckily, Dean was sweet. He smiled and placed a chaste kiss to her lips.
"Course," he said. She pulled back from him so that he could grab the collar of his shirt and pull it over his head. He tossed it to the side and ruffled a hand through his hair. She put her hands on his chest and ran her fingers over a tattoo that was on his left pec. It was a star in a circle with some sort of black waves around the circumference.
"I like this," she whispered.
Dean chuckled. "Thanks. It's kind of a, uh, family crest." She nodded and still didn't meet his eyes.
Okay, she thought to herself. It's not a big deal.
She grabbed the hem of her shirt and pulled it over her head, immediately looking down rather than meeting his eyes. "Hey," Dean whispered, "look at me." She did. He pinched her chin and smiled. "You're so beautiful, sweetheart."
She never did this sort of thing. She was with Greg for almost two years, and it took her almost a year to feel comfortable without her shirt on in front of him, and that was as far as they ever got. She had known Dean for a week, and she was already submitting to what he said, melting under his words and soft touch.
She was already in deep.
Dean kissed her, cradling her head in his hand, before trailing his lips down her neck. She felt him suck and leave a mark on her skin before kissing it and moving down to her breasts. He noticed a scar on her upper left side. "What's this?" he muttered, letting his thumb brush across the mark. She flinched, and he stopped kissing her chest to look up at her.
"'S nothing," she said, shaking her head. "I'll tell you another time."
He nodded, respecting her boundaries, and moved his left hand to knead her breast, pinching her nipple as she let out a shaky breath. He kept doing that while bringing his lips down to her right nipple. The feeling made a shiver run up her back, and she instinctively put her hand on the back of his head. She could feel him smile as he flicked her nipple with his tongue, sucking it between his lips until it was hard. He switched actions then, putting his mouth on her left nipple and keeping his hand on her right.
Soon enough, she was grinding down on his thigh. Her movements were nervous and hesitant. Dean pulled his lips away from her chest and put his hands on her hips to start guiding her movements. He made sure she moved slowly but firmly, dragging her clit up and down his thigh. She could feel whimpers in her throat, and she was embarrassed by how much she liked what was happening. She rested her forehead on Dean's shoulder and continued moving her hips with his hands. "You look so pretty like this," Dean muttered, kissing her shoulder softly. "Does it feel good, sweetheart?"
"Mhm," she hummed. "Feels, feels so good." Her fingers that were gripping his shoulders started digging their nails into his skin as she let out a soft cry. She could feel something building inside her. She may never have orgasmed before, but she wasn't so naive that she didn't know what was happening.
"Dean," she breathed out. She buried her face in his neck, and her eyes were squeezed shut.
"That's it, baby," he said. "Cum on my thigh." Her breath caught in her throat as the coil inside her snapped. She whimpered his name, and her nails dug stripes across his shoulder. Dean praised her softly in her ear, and he helped her slow the movement of her hips to a stop.
She was breathing heavily, her body collapsed against him. Dean wrapped his arms around her and ran his fingers up and down her spine. "Good girl," he cooed. He kissed her cheek, and she let out a breathy laugh.
"Wow," she whispered. "I can honestly say I didn't expect this when you brought ice cream to my door."
He laughed. "Neither did I." He kept tracing her spine. "Was that okay?"
"Yeah," she said, her voice coming out barely more than a mere breath. She laughed lightly. "I think I'm gonna put on some other pajamas." He chuckled and kissed her cheek again.
"Not a bad idea," he said.
Alice got out of bed and walked over to her drawers to get out a new pair of pajamas. She excused herself to the bathroom, and as soon as the door was closed, Dean let out a heavy breath. His cock was throbbing in his shorts, and all he wanted was to take care of it. Instead, he forced himself to think of anything to get his mind off of it.
By the time she came back out of the bathroom, he had gotten his erection under control. He smiled at Alice. The look on her face was a mixture of post-orgasmic bliss and pure innocence. He had never seen a look like that on anyone's face before, and it was so cute on her. She walked over to the bed, seeming somewhat nervous. "You don't have to stay if you don't want to," she said, playing with the hem of her shirt. "But, you can if you do want to."
Part of her felt pathetic for saying it. How needy was that? Sure, a small part of her wanted him to stay. Okay, maybe a big part of her, but that was so clingy. She quickly shook her head. "Nevermind," she said. "You don't, I mean, like, you can stay, but I totally get that you probably don't-"
"Alice," Dean said with a chuckle. "Do you want me to stay?" She shrugged, her teeth worrying into her upper lip like they so often did. Dean shook his head with a grin and patted the bed next to him as he got under the covers. "You're on breakfast duty tomorrow," he said.
She tried not to show how eager she was as she skipped over to bed and got in beside him. She immediately cuddled up to his chest as he put his arm around her. He kissed the top of her head, and she hummed contently. "Goodnight, Dean," she whispered.
He smiled. "Goodnight."
He may not've known what his endgame was, but one thing was for sure.
He was already in deep.
----- ----- ----- -----
A/N - I never thought I’d find a video of Jensen doing a face mask but here we are
warnings - language, blindfolds, bondage, oral (m and f receiving), unprotected sex (you can’t go wrong if you shield your dong), ice play, fingering, squirting, daddy kink
additional notes at the end
(previous)
The following Wednesday, Alice went shopping with Jess and Hannah after school. At first, it was awkward. They were, after all, helping Alice shop for lingerie, and Alice was not as confident as they were. But then, after a while, she started to have a good time. Jess and Hannah were making it fun and lighthearted, so Alice was able to relax, and the girls helped her find the perfect look.
When Friday rolled around, the plan they had concocted the previous Saturday was in motion.
The men, per Jess' request, had made dinner plans. This gave Alice time to head to Dean's apartment and get ready. Of course, her nerves made it so she couldn't do it alone. So, she brought along Jess and Hannah. She greeted Derek as soon as they entered the lobby. "Do you need me to let you in?" he asked.
"Nope," she said. "I actually remember the code."
"Mr. Winchester will be impressed," Derek said with a smile.
"Oh, I'm sure he will be," Jess said. Alice slapped Jess' arm, and the girls hopped on the elevator. As soon as they got into Dean's place, Alice made her way to the bathroom to change into the outfit. She stared at her reflection in the mirror, now wearing a g-string and stockings, and she was holding the corset up to her chest. She reached around to hook it closed, but couldn't quite reach it properly.
As humiliated as she felt, she stuck her head out of the bathroom. "Can one of you come help me?" she said. She heard both Jess and Hannah stand up from the bed and walk over to the bathroom.
"Hot damn, Alice!" Jess said.
"Shut up," Alice said, a blush creeping onto her cheeks. "I just can't get this fastened. There's too many hooks." Hannah smiled and had her turn around so she could get all the hooks in their right place. Since Alice wasn't facing either girl, she took the moment to speak her mind. "What if he hates it?" she asked, her voice sounding small.
"That's impossible," Jess said without hesitation. "I've known Dean a long time. He may be all tough and strong, but deep down he'd melt if you took charge."
"This is perfect, Alice, don't worry," Hannah said. "He'll love it." She fastened the last hook on the top and gave Alice's shoulders a pat. "All done," she said.
"Okay," Alice said, letting out a puff of air through her lips. "Now, the stockings hook to these bits, right?" she asked, tugging on the straps at the end of her top. The girls nodded. "Okay," she said again. "I think I can do the rest of this. How much longer is he gonna be out with the boys?"
"As long as you need," Hannah said. "Cas said they're just getting to the restaurant. Just shoot one of us a text when you're done, and we'll tell Sam and Cas to call it a night." Alice nodded and looked at herself in the mirror again. All she needed to do was her makeup and curl her hair. If she worked fast enough, she figured she'd be done in about two hours. Her stupid hair took so long to curl.
Hannah and Jess both wished her luck and said goodbye before leaving her alone in Dean's apartment. She fastened the stocking to the top, then pulled on her black skater skirt and the grey Led Zeppelin shirt she usually wore to bed. The skirt was just long enough to cover the tops of her stockings, so Dean wouldn't be able to see the lingerie under her outfit. She sat down on the floor in front of Dean's floor length mirror to do her makeup and hair. She hated standing in front of a sink for too long, so she had a tendency to sit on the floor when she knew she had a lot to do.
She played some music on her phone as she got ready, trying to calm down her nerves. It was her instrumental playlist of songs she used when her students needed quiet work time. It put her kiddos at ease, and it did the same for her.
Once she was finally ready, she sent a text to her group chat with Hannah and Jess. Jess replied that she would text Sam, and ten minutes later, she texted again saying that Dean should be on his way back to the apartment. Alice put a chair from the dining room in the middle of his room and placed two of his ties on top of the dresser so she could easily access them later. Lastly, she slid on the black heels she had bought to complete the outfit.
She heard the key wiggle in the front door, so Alice took a seat on the chair, crossing her legs and taking a deep breath. Dean's footsteps came closer to the bedroom, and she started to fiddle with her hands. When he finally walked into the room, he almost jumped out of his skin. "Jesus Christ," he muttered, putting his hand on his chest. "What are you doing here?"
She shrugged. "Thought I'd give you a surprise."
"Yeah?" Dean said with a smile as he toed his shoes off. "Well, it's good to see you." Once he had kicked his shoes to the side, she stood up from the chair and took his hand.
"C'mere," she said. "I want to show you something." Dean looked amused as he scanned her outfit.
"You dressed up your sleep shirt," he said with a smile.
"Mhm," she hummed, walking him over to the chair she had been sitting in. "Is that okay?"
Dean chuckled. "You look incredible, as always. What're you all dolled up for?"
"I told you," she said, pushing him down onto the chair. "I want to show you something."
If there was any time to feign confidence, it was now.
Dean's eyebrows furrowed as Alice walked over to where the ties were. She stood behind him, and he was trying to turn his head to look at her as she placed her hands on his shoulders, slid them down his arms, and brought them behind the chair.
"Alice," Dean said, his voice carrying an edge of warning. "What are you doing?" She didn't say anything as she held his wrists and tied them together. He grunted when she threaded her fingers in his hair and ran her hand from the base of his neck to the top of his head. She moved her hand across his shoulders as she circled his body, the other tie still in her hand. His jaw was clenched, and she was sure she had never seen his eyes look darker. She had never seen him like this at all, and it made her feel good to know she was doing this to him.
She hummed. "Show you might be the wrong word." That was when she put the tie over his eyes and tied it around the back of his head.
"Alice," Dean said, though he knew it sounded more like a growl. "Untie me right fucking now."
"I don't think so," she whispered. She walked forward and sat on his lap, tugging her fingers through his hair. He groaned and fought against the restraints.
"How'd you learn to tie this so well?" he asked.
She giggled. "I can be full of secrets too." She lifted his head and pressed her lips to his, kissing him as hard as she could. He moaned against her lips, and Alice ground down against his hips. "Wish you could see yourself," she whispered, a smile on her face. "You look so hot like this, Dean. Can't believe you're all mine."
Dean could feel her lips close to his again, and he swore she was going to kiss him. Instead, she trailed her lips down his neck, leaving red lipstick stains in her wake. She sucked a mark on his neck, and he growled and fought against the tie again.
"Alice," he said. "Fuck."
"You wanna touch me?" she whispered.
"Fuck, yes," he groaned. She just giggled and stood up from his lap, kneeling on the ground as she unbuckled his belt and jeans. He lifted his hips so she could drag his jeans and boxers off his body. His cock sprang free, and she licked her lips at the sight. She braced her hands on his knees and spread his legs, then ran her tongue up the underside of his cock, swirling it around the tip. Dean's arms fought against their restraints, and he started to lift his hips. She pulled back and dragged her nails up and down his thighs.
"Sit still," she whispered, kissing his thighs.
"Alice, if you don't let me out of this-"
She cut him off by wrapping her mouth around his cock again, taking him so far that her nose hit his pelvis. She gagged slightly, and the sound made Dean moan again. She moved slowly and purposefully, her tongue swirling around him. The slurping sounds she was making were killing Dean. He dropped his head back, deciding not being able to touch or see her was worse than any torture he experienced in the past. Alice could feel his cock start to twitch, so she pulled away, and Dean practically whined. She giggled and bit her lip as she looked at him, feeling power swell in her chest. "Please, sweetheart," Dean said, not being able to see her start to take off her skirt and t-shirt. He opened his mouth to say something again, but stopped as soon as he felt her start to undo the tie around his eyes. He blinked a few times, letting his eyes adjust, but as soon as he saw her, he let out another moan. "Jesus Christ, baby," he muttered. "Look at you."
Alice smiled and sat on his lap again, bracing her hands on his shoulders. She rolled her hips against his crotch, not quite allowing him to slide inside her. She raised her hips slightly and pushed her g-string to the side. Instead of sinking down on him, she gripped his cock and only allowed the tip to slip inside before pulling away again. "Alice," he said, that dark and warning tone returning. "Untie me. Now."
"Shh," she said. "I'm in charge."
Dean breathed out a sigh of relief as she sunk herself onto his cock. She buried her face in his neck and lightly bit it. He moaned as she moved her hips slowly against his, doing her best not to let out any of her vulnerable whimpers. She was in charge. He was the one who should feel weak and submissive. Not her. Not tonight. She was proving that she wasn't just the naive girl he thought she was. "Your cock feels so good," she said, flicking his earlobe with her tongue. "You fill me up so good." Dean moaned and tried to thrust his hips up, but she just kissed his neck again and shushed him. "Relax," she cooed. "I told you to sit still, daddy."
"Alice, I swear to god-" Dean grumbled. She cut him off with a giggle and another roll of her hips. They both moaned as he hit deep inside her causing her to clench around his cock.
"Want you to cum first, daddy," she said, trying to stop the shake in her voice. She looked down at him and pressed her lips to his, rolling her hips faster as her tongue worked its way into his mouth. When she bit his lower lip, he groaned and shot his load inside her. She pulled her lips away from him and buried her face in his neck as she tangled her fingers in his hair. He was panting as she continued rolling her hips until she felt his dick soften. She let out a sigh when she got off him, feeling his cum slide down her thigh.
The room was silent except for Dean's still heavy breathing. Alice got behind him and untied his wrists, then pulled his Led Zeppelin shirt back on. When she turned to look at him again, he was already right in front of her. He pushed her onto the bed and kissed her, all teeth and tongues, with his hands gripping her wrists and pinning them to the bed. She smiled against his lips, and he pulled away. "You think this is funny?" he asked.
"I liked watching you whine for me," she said. His eyes darkened, and his nostrils flared. "What do you want, Dean?" she whispered. She could tell he was holding back, and she didn't want him to.
"Can't do what I want to do," he muttered, bringing his lips down to her jaw. He left a mark on her jawline and she sighed.
"Yes you can," she whispered. He pulled away and looked in her eyes, his eyebrows furrowed. His eyes darted between hers, searching for some hesitance. He found none. "Show me how you want to use me, daddy." Dean lost all resolve and kissed her so hard, he knocked the wind out of her.
"You say red, and I stop right away," he said. "I don't want to hurt you."
"Don't hold back," she said, scratching her nails lightly across the stubble on his face. He licked his lips before kissing her again, then pulled the t-shirt over her head. He pushed her flat onto the bed, then stood up and looked at her. She started to prop herself up on her elbows, but he pushed her back down.
"Stay," he said. She sighed and laid back down, letting her hair fan out around her. Dean came back with four ties, and she licked her lips as she watched him take off her shoes and tie her arms and legs to the four bed posts so she was spread eagle to him. If she thought she was good at tying people up, she had nothing on him. Then again, he probably had a lot more experience. The ties didn't hurt, but she knew there was no way she'd be budging.
Dean stood up from the bed and licked his lips, rubbing his face with his hand like he was admiring his work. He reached in his back pocket and pulled out his phone. "Can I take a picture, baby?" he asked. "You just look so pretty like this." She blushed but nodded, turning her head to the side because she was too embarrassed to actually look at the camera. He chuckled and snapped a few pictures before putting his phone on the bedside table. He crawled on top of her and kissed her neck and down her chest to the fabric of her corset top. "Sweetheart," he muttered, his lips still against her skin, "I'm gonna make you cum so many times tonight." She took in a sharp breath and nodded. "But first," he said, "I want this-" He tugged at the corset. "-out of the way."
Before she could say anything, Dean gripped the corset in both hands and ripped it open. She gasped at the action and arched her back, and he pulled it out from under her. Dean surprised her by standing up and grabbing another tie. "I just realized," he said, "it wouldn't be very fair if you got to see everything when you didn't let me see anything."
"But-"
"Shh," he teased, "daddy's in charge now. Just like he should be." She bit her lip as he tied the final tie around her eyes.
"You know," she said, "does one man really need all these ties?" She jumped when he kissed her again, lightly biting her lower lip.
"Don't make me gag you too," he said.
Alice couldn't tell for sure, but the room got so silent that she swore Dean had left. The thought was confirmed when she heard him set something on the bedside table. What had he gotten? She jumped when something cold landed on the middle of her chest.
Dean hovered over her and put the ice cube in his mouth, bringing it over to her right nipple, swirling it around the bud until it hardened and the ice melted. He got another cube and did the same to her other nipple, enjoying the constant whines he was getting out of her. When the second ice cube melted, he grabbed her g-string and ripped it from her body, then grabbed another ice cube, putting it back in his mouth and dragging it down her torso before running it across her clit. "Oh," she gasped, her hips trying to lift and meet his mouth. Dean pulled back, bringing the ice cube back up her torso
"Sit still," he said, using her words against her. She bit her tongue, and forced her body to stay against the mattress. He took a fresh ice cube and went back to her pussy, keep it in his mouth and swirling it around her clit again. The contrast between his warm tongue and the cold ice cube were sending shock waves through her body. He let it slide into her slit before slurping it back into his mouth and bringing it up to her clit again.
"Dean," she cried, her head digging into the mattress. The ice was starting to melt, so he brought it back to her slit, pushing it past her folds, his tongue following. She cried out as he started fucking her with his tongue, and before she knew it, she came, squeezing her eyes shut and seeing stars.
Just as she started to come down from her high, Dean untied her legs so he could hook his arms under her thighs and lift her pussy up to his face. He dove in, slurping her juices up and sliding a finger inside her. His tongue flicked against her clit as he worked in another finger, pumping in and out as he sucked her clit until she practically screamed. His finger curved and pressed against her g-spot over and over again. "Dean," she said. "Dean, I-"
"I told you," he said. "You're gonna cum over and over tonight. So cum on my fingers." She did, her hips jerking against his face. He laid her legs back down, but before she could even fully recover from her second orgasm, he dragged his fingers out of her pussy and started rubbing her clit.
"Dean," she cried. "I, I can't. 'S too much."
"Yes you can," he said, his voice almost a growl. He continued rubbing her clit while bringing his other hand back inside her pussy, thrusting three fingers inside her now. She felt her orgasm building, but it felt different.
"Wait," she said. "Something, it's, it feels-"
"I know, baby," he said. "You can do it. You're right there."
Alice let out a choked cry as she came, not even caring about how loud she was being. Dean watched in awe as she squirted all over his arm. "There you go, sweetheart," he said, licking his lips as he watched her. "Fuck, fuck you're so perfect, baby." It took her a minute to catch her breath, and when she finally did, he pulled his fingers out of her. She whined at the feeling, and Dean grabbed his phone again. "I gotta take another picture, okay?" he said. She barely answered, just nodded and continued to focus on catching her breath. He brought his fingers down to her pussy, dragging the moisture across her slit. She jumped and tried to wiggle away from him.
"What, what happened?" she whispered. "What was that?" Dean untied her blindfold, and she blinked a few times to adjust. He kissed her softly, and she could taste herself on his lips.
"Sweetheart, you just squirted," he said.
"W-What does that mean?" she asked.
He chuckled. "It means you're even more incredible than I thought you were." She just furrowed her eyebrows, and he grinned and untied her wrists. She looked at the sheets as she sat up a bit and noticed she had stained them.
"Oh my god," she said, her cheeks turning red in embarrassment. "I did that?"
"Hell yeah, you did," he said. "And it was the hottest fucking thing I've ever seen. Now-" He grabbed her by her waist and flipped her over. She instinctively braced her elbows against the mattress. "-I'm going to fuck one more out of you." Dean was quick to kick his jeans and boxers off, his cock feeling trapped as it had gotten unbearably hard watching her. He put one hand on the space between her shoulder blades and kept her pressed against the mattress, then lifted her hips so her ass was in the air. He groaned and buried his face in her pussy again. He still wasn't used to how fucking delicious she was. She whined and squeezed her eyes shut, wiggling against him. He chuckled and pulled away, then pumped his cock in his hand before thrusting it into her. She moaned and grabbed the sheets in her fist.
Dean had never been rough with her before. He had been very careful to not let go, but tonight, he lost all resolve. His balls slapped against her skin, and his fingers were leaving bruises on her hips. Alice's breath kept getting caught in her throat, and she swore she was going to pass out from the pleasure. Dean wrapped his arm around her waist and pulled her back up so that her back was pressed to his chest. They were both sweating, their bodies sticking together, but neither of them cared. He slid his hand down her stomach and started rubbing her clit. He was right there, but he needed her to cum with him. "I know you can do it, Alice," he said. "Just one more. Be a good girl and cum one more time for daddy." Her body felt weak, but she mustered up all her strength to put her hand on the back of his head and pull his lips to hers. In seconds, she was cumming again, and her squeezing his cock was all it took for him to shoot his load inside her. Once he was able to catch his breath, Dean pulled out of her. For the second time that night, he watched as his cum dripped down her thighs.
Alice collapsed onto the bed in exhaustion. Dean chuckled and brushed his fingers through her hair. "Alice," he whispered, "why don't you go to the bathroom before you go to sleep?"
"No," she muttered. "Can't get up."
Dean chuckled. "Yes you can." He swatted her butt playfully. "Go." She whined but did as he said, also using the time to take her makeup off. By the time she came back, Dean had already changed the sheets, so she fell onto the clean bed. He smiled and walked over to his drawers to get her a clean pair of his boxers to wear. When he walked back over to her, he crouched on the floor and pulled her closer to him so he could roll each of her stockings down her legs, smiling when he noticed her eyes were still closed. He started to pull the boxers up her legs. "Sweetheart," he said softly, "gonna need you to stand up so I can put these on for you."
She whined. "You're not supposed to take care of me tonight." Still, she stood up on shaky legs and braced her hands against his shoulders as he helped her put the boxers on.
"I like taking care of you," he said when she sat back down on the edge of the bed. "Now, be a good girl and lift your arms." Alice sighed and lifted her arms so Dean could pull the Led Zeppelin shirt back on her body.
Dean went to use the bathroom and change into some clean boxers, which gave Alice a chance to think. She sighed and sat up a bit so she could pull her hair into a ponytail. She felt like nothing had changed. No matter what she did for him or let him do to her, he would still treat her like she was fragile in the end. How long before he got sick of that? Sick of her?
As soon as Alice heard the bathroom door open, she got under the covers and turned on her side, facing away from the side Dean laid on. Dean got into bed and ran his hand up and down her arm. "What'd I do wrong?" he asked, noticing how upset she was.
"Nothing," she mumbled. Dean sighed and turned her so she was facing him.
"Obviously I did something wrong," he said. "You won't even look at me." He paused. "Was I too rough? You didn't use your safe word, so I thought-" She forced her eyes to meet his which made him stop his words in their tracks.
"I don't want to be a phase."
Dean looked at her with furrowed eyebrows. "A phase?" he asked. "What are you talking about?"
"I know I'm-" She hesitated. "I know I'm so much younger than you, and, and I don't know a lot about sex, and I know you think you're having fun with me right now, but I don't want you to get sick of having to take care of me. And that doesn't mean I don't like when you take care of me. I do. I really do, but I just-" She cut herself off and hung his head.
Dean didn't know what to say. His heart was breaking. He could see how much this was hurting her, and he had no idea she had been feeling that way. Before he could say anything, she continued.
"So I thought I would show you that I could, I don't know," she said, her voice sounding so small. "That I could take charge or that you could be rougher with me and you would see that I'm not boring and that I can do more if you want me to."
Dean sighed and put his arms around her, pulling her onto his lap. She curled up against his chest, and he stroked her hair. "Sweetheart, I like you just as you are," he said. "You're not, you're not a phase. I may be older than you, but that doesn't mean anything to me. I've told you before, you don't have to change anything about yourself for me." He placed a kiss to her temple. "That's not to say that I didn't love what we just did and what you did for me," he muttered against her skin, hoping she could feel him smile. He knew she did by the way she cuddled up closer to him. "But it's okay if you like being submissive. It's okay if you like to be taken care of. I told you. I like taking care of you. I like how innocent you are." She sighed, and Dean could see her cheeks turn pink. He lifted her chin so she was looking at him. "You act like being innocent is a bad thing."
"When you're dating a mob boss, it feels like it is," she muttered. Dean sighed and shook his head.
"My whole life," he said, "I've been surrounded by hurt and violence and anger and pain. I never had a moment to be innocent. So when I look at you? I see someone who gets to be who I never got to be."
"A 22-year-old girl?" she teased. Dean smirked and lightly flicked her cheek. She just giggled and kissed his cheek, then his face grew a little more serious again.
"Innocent," he said. He hesitated and brushed some hair away from her face. "I've spent so much time running from anyone who could mean anything to me. Anyone who could show me that part of my life that I missed. It was just easier, you know? But then I found you, and you've-" He paused again and licked his lips. "It's like you've opened up this side of me that I didn't even know I had."
"So you like that I'm innocent because you never got to be innocent?" she asked, putting her chin on his chest.
"I guess," Dean said. "I don't know. I'm not making much sense am I?"
"S'okay," she said, drawing random shapes across his skin. "I think I understand. Just crazy that, that I'm the one you found."
Dean could tell she was getting more and more sleepy as the minutes ticked on. He laid her down next to him and turned so he could spoon her. "I just really like you, Dean," she whispered. "Don't want you to leave me." He looked down at her as her breathing became more steady, and he was sure she had fallen asleep. He kissed her neck again.
