Chapter Text
Dean was actually kind of enjoying this new school. It was his senior year of high school so he supposed he ought to enjoy it but it wasn’t just that.
First of all, it was big. Like, humongous. The main building could have easily fitted his old high school times two. And while the size of the buildings (that’s right, there was more than one) didn’t particularly matter it was rather the size of the student body that impressed Dean. It was about thrice as big as his old one and that ensured totally anonymity, even for the new kids. And that was awesome.
Dad had moved them here just three weeks prior and had told them that yes, this would be the one that stuck. Life had been wobbly there for a while, what with mom dying and shit hitting the fan, but apparently dad had decided that now that Sammy was entering high school too, well now they kind of had to settle down. Dean wasn’t even bitter his high school years had been spent school hopping, not as long as they stayed still now.
Wasn’t like he was going to go to college anyway. Or maybe he could actually go to State now? Possibilities started seeming endless as soon as they became stationary.
Also, the food in this school’s cafeteria was the bomb. Better than home cooked (not surprisingly since Dean was the one cooking at home).
Another good thing about this school was that people seemed friendly. He and Sammy had been kind of sticking to the house for those first two weeks in town but now, after only barely a week of school, they had both managed to get some friends. Dean supposed it helped that he and Sam weren’t the only new kids, not in a school this big. Was nice, not being the token oddball.
But the best thing, the indisputably, super best thing of everything? Well that was the cheerleaders.
Dad had given Dean the Impala so he could drive to school instead of him and Sammy having to rely on the bus but already on the second day of school dad’s truck had kind of broken down and he had ended up using the Impala for two days. Dean had grumbled while Sam had sighed and they had ended up walking to school, bus be fucking damned.
As it turned out, if they took a shortcut through the woods they ended up behind the football field and that ended up shorter than waiting for the school bus. Weird but true.
Anyway, Dean had stopped grumbling the second his eyes landed on the football field. Because there the cheerleaders were. Already in full practice mode, the team they were supposedly cheering for nowhere to be seen but fuck if Dean cared.
All he saw were long legs, flapping skirts, rustling pompoms, and swishing pony tails. Perfection.
There were some guys on the team as well and they did a really fucking good job of throwing the girls in the air, catching them in intimate embraces on their way down. Fuck Dean’s fucking luck for not being born an athlete.
So Dean might have gone back to that field only to notice that the cheerleaders seemed to be practicing almost every morning and who could fucking blame him for lingering? Jesus, they were like works of art.
Dean had always loved all kinds of women, short and tall, flat and curvy, long-haired and short-haired. Dean just loved women. And oh boy, the cheerleaders were something else.
Dean didn’t even like football and yet he found himself extremely inspired as soon as the girls started waving their pompoms around. Some stood out more than others, of course.
There was a redhead with a strong voice.
Imagine her screaming my name in ecstasy.
There was a blonde with a smile so cheeky he could see it from the bleachers.
Imagine the way she would challenge me.
There was a brunette with a thick ponytail.
Imagine running my fingers through that.
But all of them paled in comparison to this one particular girl.
She had hair so dark brown it almost looked black, it was cut in a boyish style, not nearly as short as Dean’s standard cut but definitely shorter than her friends. It suited her perfectly.
She carried herself with such dignity that it left Dean awed. He couldn’t see much details from how far away he usually was but he had been able to tell that her features were fine and sharp. And God, she just flew through the air as if she was born to do it.
Yeah, just about a week into the new school year, new school and everything, and Dean was already reduced to a gawking mess. This was going to be a fun year.
*****
Week number two started swimmingly. That was to say, it didn’t start swimmingly at all.
Sam had convinced Dean to start taking AP Math because apparently Dean was smart or something. This was all news to him but Sammy had been thoroughly unimpressed with Dean’s arguments. Plus, if he did really good he could maybe get into State after all. And maybe he wanted that now, he wasn’t so sure.
So instead of dilly-dallying about whether or not it was worth taking AP Math because he might or might not even apply for any colleges on which applications this particular class would look good, he just up and went with it.
Problem was, he had barely learned where all his other classes were and now he was suddenly overcome with the problem of finding this new one.
The map the student counselor had given him was of course useless but that was nothing new.
Nevertheless he had his eyes glued to it as he rounded a corner (probably the wrong corner) which was why he ended up smacking right into the girl coming from the other way.
She yelped and ended up on her rump, her books scattered between them and Dean was just staring like a goddamn moron. Because, of fucking course, out of everyone he could have bumped into and sent sprawling it had to be the sexy-as-sin cheerleader.
"Sorry." He stuttered (fucking stuttered!) and immediately sat down to help her gather her books.
Fucking shit, she still had her cheerleading outfit on. The skirt had risen when she sat down and showed off a creamy white thigh. Dean had to tear his eyes away.
"Thank you." She said when he handed her the books and just goddamn…
Her voice was a little deeper than most girls but it was rich in a pleasant way, sent fucking shivers down Dean’s spine and whatever. And God, her eyes.
So, okay, sure. Dean was a teenager but he wasn’t a blubbering fool. Usually.
The way he just kind of stared as the girl got to her feet would perhaps argue against that statement. Shit, he shot to his feet in the last second and realized too late what a great opportunity he had just missed. Should’ve offered his hand to help her up and then masturbate with that hand. No! Jesus, just fucking help her, nothing else.
Dean was a fucking mess.
"Are you new?"
Fucking concentrate, Winchester.
He looked down when he saw that she was pointing to the map he was still clutching (like a doofus).
"Yeah." He all but squeaked. Fucking puberty making his fucking voice crack. "I was just, you know, trying to find room A11, but…" he trailed off when she smiled a goddamn fucking dazzling smile at him. What the fuck was going on?!
"Me too." She said cheerily. "I’ll walk you."
"You’re in senior AP Math?" he cleared his throat when she tilted her head to the side questioningly. "I-I mean, not that you couldn’t be… I was more like, what are the odds, you know?"
She smiled again, smaller and more secretive. Were Dean’s knees shaking?
"I’m Cas." She held out her hand for him to shake.
Dean’s knees were shaking.
"I’m Dean."
Her grip was firm and her palm smooth.
Don’t think about where you’re gonna put that hand later. Just don’t go there. Don’t.
"Welcome to our school, Dean." Cas smiled.
Fucking don’t! What the fuck’s wrong with you?!
"Thanks." He mumbled and immediately started following Cas when she indicated that they needed to go.
"So, have you been in town long?"
How the fuck Dean managed to fumble and mumble himself through a whole conversation he would never know. But Cas was just so attentive. Listened so well to Dean when he told her about his dad getting a job here, about Sammy, and about the school in general. Listened and asked the right questions and Jesus Christ, it was hard to concentrate with her this up close.
Her hair was pulled back from her face by a thin headband and it curled nicely around her neck. It was short enough that it barely grazed her shoulders but looked so thick and shiny that Dean’s hands were practically shaking from the need to touch it.
Her blue eyes tracked Dean’s every movement and God, she looked at him as if she needed to memorize his every feature. Dean had never felt so seen.
She had a lithe build, which he already knew from what he had seen during practice but shit, seeing her move so up close was like a dream. She was just so… so smooth in her movements.
The skirt swished around her thighs and he tried really hard not to stare. It wasn’t like this was his first fucking time seeing a girl in a skirt for God’s sake. And he wasn’t a blushing virgin either so what the fuck?
But she smelled so good and looked so supple and just nngh…
She had a rather flat chest but Dean didn’t mind, not at fucking all. It suited her perfectly, made her whole visage proportionate and yeah, Dean was sweating by the time they reached the classroom.
"Here we are." Cas said cheerily and Dean smiled shakily.
As soon as they entered the classroom Cas’ friends called out to her. Dean immediately recognized the two girls as the blonde and the brunette from the cheerleading squad, and not just because they had their cheerleading outfits on as well. Man, they were pretty but Cas… Cas was…
Dean had to turn his head away so he wouldn’t get caught staring at her butt as she walked over to her friends.
And he had to talk to the teacher before class so he ended up sitting in the only seat left, which was just in front of the teacher’s desk but he didn’t mind.
This way he could spend the class imagining that Cas and her friends were looking at his back, tittering about him.
Best part was when he accidentally (he pushed it) dropped his pen over the edge of the desk and had to lean down to retrieve it. The angle made it easy for him to glance in Cas’ direction and to his immense pleasure he found her looking openly at him.
He winked at her and she smiled prettily back.
Dean came with a shout in the shower that evening. Sam’s bitchface was almost better than the actual orgasm.
*****
AP Math quickly became Dean’s favorite class. Not because he and Cas actually spent it talking all that much but because Cas was in it. Simply just there.
Dean had stopped stalking the football field, figuring he very well couldn’t be there for every cheerleading practice or it would look weird. He would either be labelled stalker or pathetic puppy and while that maybe wasn’t so wrong he’d rather avoid it.
Lord knew he tried other stuff, though.
He had befriended Benny, a cool guy with a southern drawl that Dean teased him for but secretly kind of thought was cool (and hot. Maybe?). With Benny had come other people that Dean had grown to like over the last couple of weeks. Garth, an incredibly nerdy guy, and Gordon, a street-smart kid.
Dean liked his new friends and had been a little surprised with how easily he fit in with them and how much they seemed to appreciate him. Another very good part was that they usually sat at a table in the cafeteria that made it easy for Dean to look at Cas, if she and her friends sat at their usual table. It seemed the only periods he had together with Cas was AP Math and lunch.
It was cool, though, Dean was a resourceful guy. He was sure he could find some way or another to get closer to Cas.
For one, the burn-outs hung out behind the bleachers (goddamn cliché if he ever saw one). They were kind of cool, in that detached way smoking weed and drinking could make a person. And they had no qualms about sharing with him (if he chipped in with some money, maybe perhaps?).
So he had thought about that, had shared a bum or two. But he liked Benny and the others more and besides, he had promised Sam to take his final year of high school seriously.
So becoming a permanent part of the burn-outs just to get an excuse to ogle Cas was a no-go.
His second brilliant idea was trying to join the football team. What a fucking riot.
Well, maybe he could have been good at it if he had put his mind to it but hell if he could concentrate when Cas was also out on the field. Plus, running around throwing a ball around like a jackass wasn’t that appealing.
Trying out for the cheerleading squad was out of the question. If he couldn’t even kick a goddamn football without straining a muscle, how the hell would he be able to throw girls into the air? Also, good luck concentrating on cheerleading with Cas bouncing around. Nope.
The day after Dean’s disaster of a football tryout Cas had asked him about it, sounding so cheerful that Dean wanted to splash himself with some cold water. Also wanted to die a little when he had to tell her that he didn’t make it.
But Cas didn’t sneer or scorn him. Just nodded as Dean explained why it had been a bad idea in the first place. Cas was always so understanding it hurt Dean’s heart.
Almost two months into the semester Dean wanted to call himself Cas’ friend but was fairly certain they were only acquaintances. He also wanted to shoot himself for being such a little pussy about this whole affair but that was another thing entirely.
Dean was usually pretty bold and suave with the ladies. His give-‘em-hell attitude was usually a sure fire with the females and he had always gone by the philosophy that you win some you lose some. But somehow it didn’t feel right playing it like that with Cas. Felt like she deserved more.
That plus the fact that Dean seemed incapable of holding a grown-up conversation with her. Why she was still talking to him he would never know.
The week before Halloween Dean found himself kind of dawdling in the corridor he knew Cas’ locker was in (stalker). Cas was standing by her locker, her friends around her talking about the Halloween party some girl was throwing this weekend.
Cas was smiling as she sorted through her books, two of her friends arguing over who got to wear what outfit. The sun was shining in through the windows by the stairs and it made Cas’ hair shine like a halo.
Or maybe Dean had accidentally taken some acid and was tripping balls. Gotta be one or the other, right?
"Cassie!"
Dean looked on as a guy in a peacoat approached the group of girls. Cas turned to him and so did the blonde (who Dean had learnt was called Jo, thank you very much). The others seemed uninterested.
"Fergus." Cas answered calmly. Jo looked angry for some reason but kept her trap shut.
"Told you not to call me that." The guy, Fergus, said with a grumble. Cas just smiled pleasantly.
"What can I help you with?"
"Going to Bela’s party?"
"Aren’t we all?"
Fergus rolled his eyes. "You know what I mean, honeybee."
He stepped between Cas and Jo so that Jo ended up behind his back, him crowding Cas against the still open locker door. Cas pressed her lips together and Fergus smirked.
"Fergus, please don’t."
Long-fingered hands casually flipped the hem of Cas’ skirt. A blue one today, not the cheerleading outfit, not every day. Cas shifted away and Fergus grinned.
Dean was stomping over before he was aware of it himself.
"Cas." He called in a booming voice, quieting everyone in the little group around Cas. "I forgot if we switched rooms today or not, walk me to class?"
Bold and stupid.
Fergus looked unimpressed. Cas’ eyes twinkled.
"Who the hell can’t walk to class on their own? Are you retarded?" Fergus sneered but thankfully straightened away from Cas. "Or maybe a scared little girl?"
Dean pulled himself up to his full length, towering over Fergus, chest out and eyes icy cold.
"Are you saying it’s wrong to be either one?"
"No one’s saying anything." Fergus grumbled but walked away without further arguments. Good, Dean would hate to have to punch someone in front of Cas. Or any of the other girls.
Jo snorted. "We could’ve handled him."
Well handle it fucking faster then.
Dean ignored her and the retort he had at the tip of his tongue and instead turned to Cas.
"You okay? Who was that fucking douche?"
Cas rolled her eyes but smiled amusedly at Dean. "My ex-boyfriend."
Dean tried (and failed) not to look disgusted. "Really?"
"Don’t look like that." Cas laughed. "He had his appeals but they wore off, nothing odd about it."
"We all think he’s a douche." Lisa (the brunette) supplied and Anna (the red-head) nodded solemnly.
"Cassie’s too nice." Jo muttered and looked to where Fergus had disappeared.
Cas rolled her eyes but didn’t look angry or offended. Dean shuffled on his feet, uncertain if it was okay that he was still standing there but really not inclined to leaving Cas’ side. Fuck she was pretty today.
"Well." Anna suddenly said and Dean got a little nervous when he realized that he didn’t know if he had been staring at Cas or not. "Class is starting, we’d better get going if we’re gonna have time to go to the bathroom first."
With that she hooked her arms in Jo’s and Lisa’s and the three of them started walking away, Jo grinning at Cas over her shoulder. Dean watched them leave but turned back to Cas when she closed her locker.
"Aren’t Jo and Lisa in our class?"
"They are."
Cas started walking to the classroom and Dean followed.
"Don’t you want to go with them?"
Cas looked at him with an amused expression that Dean couldn’t explain the reason for. Girls usually went in throngs to the bathroom, right? Wasn’t that what Cas’ friends were doing?
"To the restroom?" Cas asked. She pulled a lock of her hair behind her ear. "I’m good."
Dean just nodded and tried not to be weird. They walked for a while in silence, Dean almost panicking when he realized they were soon gonna be at the classroom where they would split up. He wanted to talk to Cas some more, wanted to ask about Fergus, and shit, just wanted to talk.
And maybe make out in a closet somewhere? Like this one, isn’t this a closet?
They passed the door without mishaps.
"You look really good in that skirt."
Wow. Literal foot in the mouth.
Cas blushed a little.
"Thank you, Dean." She smiled.
"I mean, you look good in general." Stop talking. "Just, you know, blue suits you."
"My sister bought it for me, said it brings out my eyes."
"Smart." God, it sounded like he was praising a fucking dog.
Just outside the classroom Cas stopped and turned to Dean. She looked shy all of a sudden and oh my God was she aware that she was biting her lip? Was she trying to make Dean pop a boner right now? And it was working so well too, holy fucking shit. Impending boner alert.
"Are you going to the Halloween party?"
Dean tried to swallow. Too much movement now and he would really be sporting a sticky. Goddamnit.
"I’ve been thinking about it. Benny and the guys are going so…" he shrugged.
He wasn’t really a fan of Halloween or costumes so he had thought to maybe sit this one out but…
"Well, maybe I’ll see you there?"
But on the other hand, Halloween was awesome.
"Yeah, maybe."
*****
The Friday that week, the day before the party, Dean sat out on the bleachers openly looking at the cheerleading squad as they practiced. The visual stimuli was almost enough to get his overly excited dick to perk up but the constant tugging it had been subjected to in the last week kept it in check for now.
He was chewing on his lower lip, thinking his costume options through. Sammy had told him to make it easy for himself and go as a cowboy. Dean would probably go as a cowboy or not dress up at all. He had considered James Dean as well but supposed that would be considered "too little" in the way of an outfit.
He wondered what Cas would be going as.
The bleachers rattled as Benny climbed them. He sat down beside Dean and just looked on as the cheerleaders jumped, waved pompoms, and just generally cheered. Everything looked so goddamn smooth.
"So," Benny glanced at him. "Liking the cheerleaders, are we?"
Dean rolled his eyes.
"They’re fucking hot, you know that too."
"Sure do."
"So how does it work at this school?" Dean shifted to sit straighter. Cas was leading a cheer. "Gotta be on the football team if I wanna date one?"
Benny chuckled. "Nah. Clichés like that belong in the movies, brother."
Or at Dean’s last school but whatever.
"Well lucky me then because I sucked at football."
"You tried out?" Benny’s eyes gleamed with amusement. Probably shouldn’t have said that. Dean looked away but could still see how Benny’s eyes softened. "I think that Sarah Blake is dating one of the football dudes but otherwise it’s pretty mixed up." He said. "I don’t even think all of them have boyfriends."
Dean nodded casually, tried to play it cool but shit. His heart leapt up into his throat when Cas was thrown into the air. Her skirt flapped and she nailed the landing.
They sat for a while in companionable silence and Dean really appreciated that. Benny was by far his favorite friend and moments like this confirmed it.
"Got your eye on someone special?" Benny asked suddenly and Dean shifted, uneasy with sharing the exact details.
He had never really liked someone this much before so he felt open and exposed.
"Maybe."
"You see the one with the braid?" Benny pointed to one of the girls. She was pretty, Dean had noticed her before, but not nearly as pretty as Cas, don’t be ridiculous.
"Yeah?"
"You’d do well not to drool over her."
Dean turned to Benny and grinned. "Yeah? She taken?"
It was Benny’s turn to shrug casually. "She’s… Andrea and me we have this dance."
Dean laughed out loud and clapped his friend on the shoulder. "Don’t worry, man. I’m not gonna try and take your girl. I just like cheerleaders."
Benny smirked. "Don’t we all, brother?"
*****
Dean felt ridiculous. Sam had told him he wore the cowboy outfit really well and Dean had made the mistake of trusting his fourteen-year-old brother. Jesus, he looked like a goddamn fool.
Well, at least he wasn’t the worst. Garth had actually dressed like the dude from The Fly, complete with a giant ass fly mask on his head. If Dean didn’t like Garth so much he would have been embarrassed to be seen with him.
On the other hand, Garth’s antics seemed a hit with the ladies and didn’t girls usually like men who could make them laugh? Dean didn’t know anymore, just felt like a wreck.
He straightened the hat for the tenth time since arriving (he needed to find somewhere to conveniently lose it or he would go mad), weaving his way through the throngs of people in this Bela girl’s house.
The music was loud and exceptionally bad. Dean had driven so he could go home when he wanted to, which he suspected would be the second after he’d seen Cas and gotten a heart attack. He’d spotted Jo and Anna and if Cas’ costume was half as slutty as theirs Dean wasn’t going to survive it.
He felt like he needed a drink to ease his nerves and to make him relax. With alcohol in his blood he was sure to be better at ignoring how atrocious the music was and how annoying anyone who wasn’t Cas was. But he had driven his beloved Impala and he didn’t want to crash her. Fucking shit, why had he even come?
And then he spotted Cas and it became blaringly obvious why he had come.
She was clad in a demure white dress, a pair of fluffy white wings on her back, obviously dressed up as an angel and for some reason the not-sluttyness of her outfit made her even sexier.
Dean had to hang back for a moment and just watch her as she talked to Lisa and some other people Dean didn’t know.
Grip. Gotta get a grip.
Needed a grip on his dick but that would have to wait. Nice choice to wear restricting jeans. And he could blame his choice in pants on the costume so it didn’t look weird. Should maybe have thanked Sammy instead of bitching about the hat.
And then Lisa saw him and he just wanted to rip the hat off his head.
"Dean!" she called, loud and clear, enough to be heard over the music and fuckfuckfuck, Cas turned at her friend’s word.
And then Cas smiled.
Dean’s world felt off kilter and he really fucking needed to get a hold on his boner-situation. Needed to make it a non-situation.
But too late, Cas was already coming over, her friends in tow.
"A cowboy? How original." One of the girls said. Dean recognized her as Meg, one of the burn-outs. Funny she was hanging with Cas and her gang. Guess this school really didn’t get hung up on cliques. Good to know.
"Catwoman?" he responded with a cheeky grin. "How original."
Meg sneered at him but Cas’ smile was too dazzling for Meg to ruin this moment for him.
"I think it suits you." She said almost shyly. Dean’s cheeks were burning. Good thing the lighting was dim.
"You want something to drink?" Lisa asked.
Dean thought about his Impala but decided that he needed at least one drink if he was to calm down.
"Beer?"
"In the kitchen." Lisa answered with a smile and they all walked over to the keg.
Dean was impressed, whoever this Bela chick was she certainly didn’t cheap out, that was for fucking sure.
They drank for a while, Dean mostly sipping his beer (wanted to quaff it). Conversations were easy and Dean was relieved to find that he kind of fit in with these girls just as he had fitted in with Benny and the guys.
At some point Benny and Andrea appeared, looking disheveled in a decidedly pleasant way and conversations shifted over to them instead.
"Do you want to dance?" Cas bit her lip again and Dean’s knees trembled.
Dean hated dancing but on the other hand this was a chance to have Cas pressed against him. Alone.
"Sure."
Cas led him to a bigger room (supposedly the living room with the furniture removed) and Dean couldn’t help staring at her perfectly round ass. Her fake wings bounced lightly when she walked and Jesus Christ, that dress was tight.
As they joined the rest of the dancers Dean noted thankfully that this was a regular chance-to-grind-against-each-other kind of dance. Nothing fancy, just a bunch of horny high schoolers smashing their privates together. Awesome.
Dean grinned down at Cas when she snaked her arms around his neck. She smiled coyly at him and yep, Dean’s heart was seriously in danger of beating out of his chest. Just gotta do this right and not get a boner. Difficult, considering that had been a problem ever since he first saw Cas but totally doable. Yep.
They danced for a while, pressed tight together but nothing overly indecent. Cas smelled wonderful, her eyes so big and blue that Dean felt like he was drowning in them. And that was good, staved off the immediate arousal for a while.
And then the song changed to something more… intimate but bouncy. It was hard to describe and it wasn’t like Dean cared to try either. Not with the way Cas smiled in recognition of the song and abruptly turned around to dance with her back pressed against Dean’s chest.
Her wings got smashed between them but they were small enough that it wasn’t a problem. Dean just put his hands on Cas’ hips and loved the way they felt. Sharp and agile. Goddamn, Cas knew how to fucking move.
She grinded her ass back against Dean’s crotch like she wanted him to cream his pants and maybe that wasn’t so farfetched a thought. He pressed in close, hands gripping her hips and his lips grazing her smooth neck.
She craned her head to the side and put her hands over his, swaying her hips to the music and God…
Don’t fucking moan her name right in the fucking ear.
It was a hard-fought battle.
It took very little for Dean to become fully hard and he was very sure Cas must be feeling his dick even through his jeans but she just kept grinding back, almost chasing him.
Dean’s hands flexed on Cas’ hips, holding her tighter. His dick wept in his underwear. Cas gasped when he thrust once against her, unable not to.
"Fucking hell, babe." He murmured, lips pressed to Cas’ heated ear. "So fucking sexy."
"Dean."
Fuck, the way Cas just kind of sighed out his name made Dean thrust against her again. He was very glad that it was dark and the people around them were occupied with approximately the same thing he and Cas were engaged in. No one was paying them any attention and that was good because Dean didn’t think he could stop even if everyone was staring openly at them. In fact, that thought just made him even hotter.
"You make me so goddamn hard, fuck." He breathed harshly when Cas bucked back slightly. "Don’t wanna… I mean, you’re so fucking fine, wanna do things right."
Was he fucking drunk or what the fuck?! Why the hell was he admitting this to Cas for? How uncool.
Cas suddenly twirled around in his arms and he had an icy cold moment when he thought he had gone too far but then Cas was leaning in, just barely grazing their lips together.
"Wanna get out of here?"
Dean’s whole body shuddered. "Fuck yeah."
Cas took Dean by the hand and all but dragged him upstairs to an empty bedroom because apparently Dean’s life was a high school movie cliché. Not that he minded. Not when Cas closed the door before leaning against it and pulling Dean close.
Cas tasted sweet, probably like the drink she had been drinking earlier but beneath that was the underlying taste of Cas herself and sweet mother of everything sweet.
Dean groaned unashamedly and deepened the kiss almost immediately. Cas seemed to appreciate it. Her hands were fisted in Dean’s shirt and she tried to pull him closer.
His stupid hat bumped the door and he ripped it off only to throw it somewhere over his shoulder, not fucking caring. Goddamnit, two months of ridiculous pining and he finally had his lips on Cas. It felt like a fucking dream.
"Dean." Cas moaned prettily and tried pulling him closer again.
But Dean was holding himself back, for a number of reasons. One was that it was fun to tease Cas, her desperate little gasps fueling Dean’s arousal so good.
Two was that he didn’t want to indulge himself and rub against her like some horny dog. Cas deserved better than that.
And three was that Dean was pretty sure he would come the moment he started grinding. Couldn’t really handle kissing Cas and grinding. One thing at a time, at least right now.
"Fuck, baby." He mumbled, one hand on Cas’ hips, holding her still, and one hand coming up to caress her face. "You’re so fucking beautiful."
Cas blushed, Dean could see it even in the barely lit room. She looked down and bit her lip like she did when she was shy (much to Dean’s dick’s immense pleasure).
"Really?"
Dean just had to kiss her hard. "What do you mean, really?" he grinned, cupping her head, finally feeling that hair between his fingers. "I’ve fucking wanted you since I first saw you. Prettiest girl in school."
God, Dean needed to come. But needed Cas to come even more. Needed her keening and writhing as Dean fingered her. Needed her to come again when he was inside her. Needed to ruin her for other men. Needed her to be his.
"Prettiest girl?" Cas repeated in a question.
Dean leaned on the door, his other hand still on Cas’ hip, massaging her. Kneading, almost.
"No doubt. Never seen anyone better." He licked his lips self-consciously. Cas was looking at him with an unreadable expression. "Not gonna lie, Cas. I’ve been with a couple of women before but no one’s affected me like you. I’m a fucking mess around you."
"So you’ve had sex with women before and now you want to have sex with me, a woman, too?"
What the hell kind of question was that?
"Yeah." Dean pulled back a little when Cas looked down. "But shit, you’re not just like another notch or anything, don’t think that." Oh, panic was slowly replacing Dean’s arousal. "I’m just shitty at expressing myself. I’m sorry, Cas."
"I think…" Cas looked away, pulled her arms around herself and looked small. Dean took an actual step back. "I need to go."
"Shit, Cas. I didn’t mean anything bad." Dean’s whole body felt cold. "I didn’t mean you’re not special, I…"
Fuck, he had just said the opposite, hadn’t he? He was seriously panicking now.
Cas looked up at him through her eyelashes, a very small smile playing on her lips. "I know, Dean. I know what you meant." Immense relief washed over Dean but it didn’t really last when he realized Cas was still leaving.
"Cas, what’s wrong?" he wanted to reach out but instead just stepped back when Cas turned to the door. "I didn’t mean to move so fast and I’m sorry I’m always running my mouth."
Cas stopped his desperate ranting by putting a hand on his arm. "Dean, you did nothing wrong." She smiled a sad little smile. "Can we talk on Monday? Can you give me the weekend?"
"Sure." Anything, he would give Cas anything.
Didn’t stop him from feeling miserable when Cas had left him alone in the dark room, though. Fuck, he had managed to screw this up, hadn’t he?
Fucking shocker.
First time he actually liked someone and he had to ruin it by getting too eager. This was no one’s fault but his. And now Cas would think he was just some kind of pervert. Fuck, everyone would hate him.
He walked glumly downstairs and aimed to sneak away but of course Jo spotted him. Her look told him Cas had told her what had happened. He remained standing by the stairs as she walked up to him.
"Don’t beat yourself up."
"What?"
Hadn’t really expected her to say something like that.
She smiled kindly. "Just give Cassie some time to think and promise me that when you two talk you’ll keep an open mind. Cassie really likes you."
Despite everything he felt a little spark of hope at her words. "I promise." He mumbled, uncertain what she was talking about precisely but determined to obey her. Cas deserved it.
It was only when he got home that he realized he had forgotten the hat in that goddamn bedroom. Well fuck.
*****
"Are you going to mope all Sunday?"
Dean swatted away Sammy’s hand. "I’m not moping. I’m hungover."
"You weren’t even drunk yesterday and you got back before midnight. You’re not hungover."
Dean wished Sam would stop being so goddamn perceptive all the fucking time and start acting like a kid again (although he was well into puberty and growing taller every day. Would probably grow taller than Dean, bastard).
"Leave me alone. I just wanna sit this day out." Get back to school, talk to Cas.
True to his word he had made no effort at contacting Cas. Not that he really could have even if he wanted to (he really wanted to) because he had no way to contact Cas. No phone number, no house address. No nothing.
Just the phantom feeling of Cas’ body against him and a thrumming arousal that went nowhere. He was even too morose to jerk off, although Lord knew he fucking needed it. Felt wasted.
"Fine." Sammy snorted and got up from Dean’s bed where Dean was curled into a ball of self-hate. "Just know you owe me for the cowboy hat."
Fucking Halloween.
*****
Dean was not proud to admit that he all but ran into school on Monday, leaving Sam by the Impala to fend for himself. Not that the squirt needed him but whatever.
Cas was standing by her locker together with her friends and shit, she looked as beautiful as usual. She had on a simple white button down, short sleeved and tight. Her skirt today was a salmon colored thing with black lace along the hem and oh boy, Dean needed to focus to not let his eyes wander.
He cautiously walked over to the group of girls but was of course easily spotted. Jo gave him a smile and Cas perked up at the sight of him.
"Hi, um…" he rubbed at his neck, feeling stupid.
But Cas took his hand before he could make a fool of himself. "Can you talk right now? Do you have time?"
If it had been up to Dean they would have been talking Saturday.
"Yeah."
Cas smiled a little and pulled him with her as she started walking away. Dean glanced over his shoulder and saw that Lisa was smiling at him too. Okay, so maybe he hadn’t screwed up too much? Maybe Cas was just gonna let him down real nice? Sure, that would feel awful but it would at least be better than him being a fucking pervert.
Cas didn’t say anything for the whole walk. Just led him by the hand (it felt fucking fantastic holding Cas’ hand) and Dean didn’t question where they were going.
He frowned in confusion when Cas started leading him up a flight of stairs he hadn’t gone up before but he still kept silent. Cas’ swaying ass was right in front of him too and fucking shit, that skirt. Dean loved lace.
The stairs ended in a door marked Roof, no admittance and Cas just pushed the door open, clearly ignoring the sign.
"Wow." Dean mumbled and squinted in the sunlight. "Never knew you could go up here."
Cas quirked her lips. "People do it all the time. Mostly to hide from class, even though I suspect the teachers know."
She pulled him around the little house that made up the stair and door. On the other side was a park bench that looked suspiciously similar to the ones down in the quad. The floor around the bench was littered with old cigarette buds but the space was otherwise empty.
"Oh, good." Cas said and gestured for Dean to sit down on the bench. He did so slowly, only a little (a lot) sad to let go of her hand. "There was a chance that there would be people here. I wanted privacy."
Dean swallowed with a click that sounded overly loud to him. "Look, Cas—"
Cas held up a hand and Dean stopped immediately. "Dean, please let me talk first. I need to make this right." Make what right? Dean leaned back on the bench, just kind of staring at Cas who was standing before him, looking beautiful. "Are you okay with maybe missing homeroom?"
Dean wanted to snort because of course he was okay with that but he thought that would sound wrong.
"Of course." He mumbled. His hands curled into loose fists against his thighs when Cas smiled demurely at him.
"I want to explain why I stopped us at the party." She started and pulled a stray lock behind her ear. "I really like you Dean but you said some things that made me realize I haven’t been completely honest with you."
Dean frowned in confusion. "Cas, I didn’t mean to make you upset."
Cas smiled. "You didn’t. I just…" she sighed deeply. "I just have some things to come clean about. And this is really my fault. I’ve been doing this for so long and everyone close to me knows." Dean felt as if his face was permanently stuck in that confused frown. Cas shifted on her feet. "I mean, my whole family knows, the teachers know, all my friends know. And it’s not a big deal anymore. I’m comfortable like this and I just…" she sighed again, more frustrated now. "I guess I kind of forgot how not everyone automatically knows, you know?"
"Um…" Dean had never been so confused in his life. "Might wanna fill me in a little more, Cas."
Cas bit her lower lip and looked down, fisted her skirt slightly. "My full name is Castiel. I’m a boy and I just like to dress like a girl."
The world seemed to slow down as Dean was trying to catch up with what was going on.
"Uh…"
Cas sighed (again!) and lifted her skirt a little. Underneath she had on a pair of white panties and holymotherofeverythingholythatwasadick. And balls. A dick and balls trapped snugly in a tight pair of white panties.
Dean’s eyes budged out and his hands cramped against his thighs.
"I’m not like transgender, if you want a label." Cas continued but Dean barely heard her—him! Could only stare.
It looks like satin. Wonder what it feels like?
"I actually enjoy my gender, I’m just." Cas shrugged. "I’m a boy that likes to cross-dress. A transvestite I suppose, if you have to label it. And gay, for the record."
Dean was slowly reaching out a trembling hand. Cas’ thighs were still as creamy white, her—his! (goddamn pronouns) eyes still as blue. Lips still as plump.
"I just really like you, Dean, and I hope this won’t come in between us. I mean, I get it that you thought I was a girl and that you might not like boys. I’m not asking anything like that, I just hope that we can at least remain friends. And I’m sorry things happened the way they did, I would really like for us to—what are you doing?"
Dean looked up at Cas’ question, only then realizing he had put one hand on Cas’ thigh and the other on his own dick. Also realized just now that he was fucking hard as a fucking rock.
"Uh, I, um…"
Cas’ grip on his (hah! Got it right!) skirt tightened but he didn’t lower it. There were so many things Dean wanted to ask right now but all his blood was in his dick. Plus, he had always been kind of a moron around Cas.
"Boobs?"
Fucking hell, Winchester!
Cas blinked. "Are asking about my breasts?"
"Maybe." Dean breathed. His hands were massaging now. Cas’ thigh and Dean’s dick alike. Cas’ eyes looked hooded but maybe it was just the sun.
"They’re fake. It’s just a padded bra. I don’t even wear one when I’m cheering, I thought you would’ve have seen." He bit his lip again. Dean’s dick jumped against his hand. "I’ve seen you watching us."
"You." Dean swallowed to get some goddamn moisture in his mouth so he wouldn’t sound like a frog. "I’ve been watching you."
"I was hoping." Cas tilted his head to the side, quirking his lips. "Do you like my panties, Dean?"
"Fucking hell, Cas." Dean groaned, rubbing his dick harder when he realized he was grazing the panties with his fingers. "So fucking hard for you."
Careful now, don’t wanna scare him off again.
Dean didn’t know who that rational voice was but he tried his damndest to obey it. Even though his dick was already leaking and fuck, he had needed to come for too long. And here Cas was, standing with his skirt lifted for Dean to see everything.
Cas’ breath hitched at Dean’s words. "You want me?" he asked, his tone reverent. "Even though I’m a boy?"
"I just—fuck—I just want you." Dean gripped Cas’ hip, tried pulling him closer and Cas stumbled forward.
Dean was rubbing his own dick continuously now and it hurt to be trapped in his jeans but it hurt so good.
"Even if I dress like this? I tricked you, Dean."
"Didn’t do it on purpose, right?" Dean mumbled, hardly understanding his own words. Cas’ dick was certainly perking up at the sound of Dean’s hushed voice. It jumped against the restricting panties. Dean bit his own lip at the sight. "Fuck you look so hot, baby. I can’t even…" he looked up to see Cas staring down at him with eyes dark from lust. "I’ve never been with a guy, never wanted to. But I… Can I touch you? Please?"
Cas gasped sharply and then nodded, licking his lips once. He remained standing still as Dean let his hand roam over his body.
His thighs, his hips. Back to squeeze his butt and fuck, that made Cas’ hips jerk and he moaned lowly. Up and beneath the shirt to rub Cas’ stomach, toned and flat and so fucking smooth.
And down over Cas’ dick and balls. He felt smaller than Dean himself but still clearly manly. No fucking mistaking this part. Dean’s dick ached and jumped and spit out more precome.
"So fucking perfect." Dean rasped. Cas’ grip on the skirt had his knuckles go white. His hands were shaking. Dean rubbed furiously on his dick, so ready to come now. "Turn around, wanna see your ass."
Cas mewled (fucking mewled) and turned around. He lifted the skirt over the swell of his round cheeks and bent forward just a little, spreading his legs just a little, arched his back just a little.
"Fuck!" Dean groaned and bucked up into his hand even as he was grabbing Cas’ ass, kneading the meat, pulling him closer. "Gonna make me fucking come in my pants, Cas. Fuck, baby."
Cas gasped. "Dean, are you…?"
"So fucking close." Dean’s breath came in short stutters. The bench was groaning along with his desperate movements. "Need you Cas, don’t care if you’re a boy or girl, need to be inside you."
Cas twirled around so fast Dean almost got dizzy from the sight of the flapping skirt. And then suddenly nothing mattered anymore because he had his lap full of Cas.
The boy’s knees pressed against Dean’s hips, his skirt spread out over their laps, his crotch against Dean’s, and his lips against Dean’s.
And Dean came with a strangled shout that Cas eagerly swallowed.
He gripped Cas hard, pressing the lithe body down against his dick even as he thrust up and fucking shit, he saw stars with how hard he came. Cas kept grinding down against him, his own hard-on prominent but he didn’t seem to be as desperate as Dean.
"You look so good, Dean." Cas mumbled, their lips still almost connected even if Dean was contributing very little to the kiss. His whole body went lax after his orgasm and he felt content to just sit there and let Cas pet him. "So handsome when you come for me."
"S-shit." Dean mumbled, barely aware of how hard he was clutching Cas. He nosed against Cas’ neck, reveling in how nice the boy smelled. Boy! Fucking hell.
"Are you okay?" Cas mumbled after a while. Dean could feel that he was still a little hard even if it seemed to have diminished during their cuddling (oh boy, Dean was actually cuddling).
"Are you? Do you want me to…?" he didn’t know how to finish that sentence, which was ridiculous considering he had a dick too. He knew what could and should not be done to a dick.
Fucking man up, Winchester.
But Cas shook his head and leaned out a bit so that he was merely sitting on Dean’s lap. "It’s okay. Sex wasn’t my intention anyway."
Dean blushed so hard it hurt. "I’m sorry."
"I’m not."
Cas’ cheeky grin made Dean feel marginally better.
"No but I mean it, Cas." The skirt’s material felt nice under Dean’s hands. "I get it that you wanted to talk and this was serious but I just… I guess I’ve been a little pent up over the weekend." He grinned and it was Cas’ turn to blush. He did so with a continued smile, though. "And while I’m fucking surprised you’re actually a guy it really doesn’t matter." He looked down and frowned a little. "Feels like maybe it should but with you... I dunno," he shrugged and smiled again. "I just don’t care."
"Oh, Dean." Cas mumbled and caressed Dean’s cheek. He was sure the gesture was meant to be comforting but Cas’ tone had been too sad.
"Guys have told you this before, haven’t they?"
"Yeah."
Dean pursed his lips. "Did they hurt you?"
Cas shook his head but stopped abruptly to seemingly think it through. "Not physically." He said with a sad smile and Dean wanted to murder anyone who put that look on Cas’ face.
"Who was it, Cas. Was it Fergus?"
Cas raised his eyebrows in surprise. His hands fisted against Dean’s chest. "Not only but Fergus was… Well, I liked him more than I had liked anyone else and he said he was okay with it but I don’t think he really was. He never wanted me to wear anything feminine to bed and," he shrugged. "I was okay with it for a while but I don’t want to hide this side of me. Not when everyone else seem okay with it."
"And you shouldn’t have to either." Fuck, Dean felt protective and weird and hot (and in love. Who the fuck said that?!). "Why the hell is he sniffing around you now for, then?"
Cas blinked and then smiled so knowingly Dean thought he should feel embarrassed but didn’t. "Guess he thinks we could still work things out."
"You can’t." It was Dean’s turn to blink at his own words. Cas was just looking curiously at him. "I mean…" he coughed self-consciously and glanced to the side. "I suppose you could and all but you can’t—I mean shouldn’t!" he sighed and forced himself to look Cas in the eyes. "What I’m trying to fucking say is that even if you work things out with him I don’t want you to get back together with him."
Cas tilted his head to the side. "Might want to elaborate that a little, Dean." Well fuck, Cas was clearly playing with him, Dean could see from the cheeky glint in the other boy’s eyes. And Dean loved it.
"Can we just forget the last ten minutes? I mean, not the conversations, those stay, but can we forget my embarrassing behavior and start over?"
"I don’t know." Cas said teasingly. "I might want to relive it when I jack off later."
Dean’s breath stuttered on an exhale. "Okay." He squeaked. "Well, apart from that…" he had to clear his throat before continuing. "Would you like to try and date me?"
Cas smiled his dazzling smile. Dean was glad he was already sitting down or his knees would have buckled.
"I would."
"Don’t be so hasty in your decision." Dean warned but shit, his chest felt ten times tighter with how elated he felt. "I eat a lot and have no table manners. And I swear all the fucking time. I have no money and I tend to put my foot in my mouth."
Cas put his hands around Dean’s neck and leaned down to kiss his lips chastely. "I think I can live with that. Also, I have a few suggestions of what you could put in that mouth of yours instead."
"Holy…"
The next kiss was much deeper, Dean’s hand tangled in Cas’ hair and Cas cradling Dean’s face in his. It somehow didn’t feel odd knowing he was kissing a guy, maybe it was because he had come to know Cas as a girl or maybe it was because Dean was so wrapped up in Cas in general that he didn’t care. He couldn’t say and he didn’t fucking care, not with how good it felt to have Cas writhing in his lap.
"We should get to class." Cas mumbled after what felt like an eternity of bliss.
"We should." Dean mumbled and shivered at the sound Cas let out when he pulled on the boy’s hair.
"I need to tell the girls about this."
Dean cringed a little. "Not all of it, please."
Cas laughed and sat back a little. The come had dried in Dean’s underwear now and it was immensely uncomfortable but as long as it wasn’t visible he thought he could live with it.
"Maybe not, no." Cas conceded with a grin. "But about the part where you’d wanna date me even though I’m like this."
Dean frowned. "Don’t say it like that, there’s nothing wrong with you." He grinned suddenly and rubbed circles on Cas’ hips with his thumbs. "Still the prettiest girl in school. Prettiest boy too."
Cas laughed again, an elated sound that made Dean’s heart swell. "You know; the girls were really sure you’d be okay with this even though you were tricked. At least that you wouldn’t be angry."
"And you weren’t?"
Cas looked down and shrugged a little. "I hoped but since I’m a little more emotionally invested than them I guess it was easier for me to imagine the worst."
Dean got that and he wanted to say something comforting. But the truth was that he got stuck on more emotionally invested and couldn’t help his own feelings fluttering about like stupid butterflies or something.
The actual truth was that he wasn’t certain about having sex with a guy and maybe dating someone like Cas would be difficult, Dean couldn’t tell. All he did know was how right it felt kissing Cas and how much he wanted more. More time with the guy, more sex. Just more.
"We’re gonna make this work, baby." He murmured intimately and Cas smiled coyly, making Dean’s heart swell again. God, he loved that feeling.