A/N I have two parts to this and I was going to post it all together but the second part is taking forever for me to write so I thought I'd post the first and you guys can motivate me to write the second faster

Warnings: Alternate Universe - High School, Alternate Universe - Human, Anal Sex, Bottom Castiel, Top Dean, Blow Jobs, Hand Jobs, Crossdressing, Panty Kink, Older Dean, Younger Castiel, Age Difference, Dirty Talk

"You can do this. You are Dean Winchester. There is no way that you are going to screw this up." The words reflected back to him in his bathroom mirror as he adjusted the tie to his suit. He was dressed in a white button down with a black and white striped tie and black slacks. His suit jacket was sitting on the back of his desk chair in his room which he would put on just as he was leaving so he didn't wrinkle it. He definitely didn't want any wrinkles tonight. It was an important night and he did not want to screw it up.

With one final glance in the mirror and one more hand to his hair to flatten his comb over, he let out a sigh and headed to his room where he sat on the end of his bed. He bent down to put on his black leather shoes which he had just polished so they were shiny and clean before he reached over and grabbed his phone.

Leaving now. Be there soon. xox

He clicked send after typing the number he had learnt off by heart after five minutes of having it because even back then he knew it was a number he needed to remember. When the reply came in with a 'See you soon' and a smiley emoticon, Dean couldn't help but smile and feel some of the nerves that had been churning in his gut ever since he had been asked to do this, dissipate.

Castiel Novak was his boyfriend of three months and tonight was the night he was going to be introduced to his parents. According to Cas, they didn't care that their son was gay all they cared about was that the boy their precious son settled with was the right one for him. He knew, from what Cas had told him of his parents, that they had very high expectations for their son and that spanned over all aspects of his life including who he chose to date. The Novaks were proud people who were very well off and were rather selective with whom they chose to socialise with. There were times when Dean and Cas were alone that Cas would confess to not liking how his parents acted but he still loved them all the same. Dean knew he needed to make the right impression and by dressing in the suit he wore to his Uncle Bobby's wedding when he finally got his act together and married Ellen Harvelle, it was the first step to giving that impression.

The teen pocketed his phone making sure to put it on silent so that if it did go off during dinner he wouldn't seem like a rude teenager who couldn't be away from his phone for one measly dinner. He knew it more than likely wouldn't go off seeing as the only people that messaged him was Cas and his little brother, Sam. Sam knew all about the importance of the dinner and knew better than to text his brother but it was better to be safe than sorry. Once he had slipped his jacket onto his shoulders, Dean smoothed his hands down the front as he buttoned the top button and let out another breath before grabbing his wallet and trotted down the stairs. When he got there, he was greeted by his mother, Mary, who was beaming at him.

"You look so handsome. There's no way they aren't going to like you" she gushed. When he reached the bottom, she reached out and pulled him into a hug and whispered into his ear. "Stop worrying. Anyone with eyes can see how smitten you two are for each other. They won't do anything to jeopardise that" Dean nodded as he inhaled his mother's scent which never failed to calm him. She pressed a kiss to his cleanly shaved cheek which he knew Cas would hate but he didn't think his parents would appreciate the three day stubble he usually displayed. With a smile she pulled away from him and tapped his cheek lightly with her soft finger tips "Off you go. You don't want to be late".

"Yeah" Dean replied dumbly "I'll see you later" Dean kissed her cheek and gathered the keys to his Impala which had come into his possession almost two years ago on his sixteenth birthday and he had acquired his driving license. His father, John, had given it to him and told him to look after the vehicle which he did even if he did have to put in a lot of elbow grease to get rid of the stains he and Cas left in the back seat on a number of occasions. It was worth the sore arm any day to see Cas writhing and pleading for Dean as he hovered over the top of him teasing and giving him everything but what he wanted. But tonight, not even those thoughts could calm his nerves because he knew if he screwed things up with Cas' parents then he and Cas' relationship could cease to exist. But he couldn't think about that right now. All he had to do was do the best he could and hope for the best.

Dean started his Impala with a roar and relished the somewhat calming rumble of his vehicle. As he drove, he thought over what he would say and topics he would avoid. Particularly the ones that weren't ones you would share to anyone especially your boyfriend's parents and unfortunately how they met fell into that category.

It was at a Halloween party that they first met three months earlier which Cas' parents didn't even know Cas attended. He was supposed to be studying with his friend Anna but had snuck out to attend the party. Dean wasn't initially going to go but had reluctantly agreed when his friend Jo has begged him to go with her. He hadn't dressed up extravagantly instead choosing to grab a Zorro mask and a black cape as a last minute costume while he dressed in black jeans that were a little tighter than his usual attire and a black tee that hugged his figure well. Dean knew he was hot and there was no harm in showing it off.

When they arrived at the party, Dean found himself ditched. Jo had run off with a friend of hers leaving Dean by himself stood in the doorway in a sea of unfamiliar faces. Jo was a childhood friend but they attended different schools meaning not all Jo's friends were Dean's friends. Jo attended private school while Dean was in the public system. It meant that when Jo dragged him to rich-boy parties such as that one, he often found himself looking for someone to hook up with because Jo more often than not left him to socialise. That night though as Dean scanned the crowd he didn't find anyone that caught his eye. Of course it was still early so with a sigh Dean headed for the kitchen to find a drink. When he got there he was greeted to the sight of a fantastic ass clothed in a tight white mini skirt. As Dean moved closer, he realised the owner of the fantastic ass was dressed as a nurse and was in fact a very handsome guy. Dean had been open about his sexuality for a while and there was no way he was going to pass up the opportunity before him.

Once he was close enough, Dean grabbed a red solo cup and filled it with the liquid from the keg before turning his sights to the nurse. The guy was absolutely gorgeous and Dean's breath caught in his throat as he took in the teen's appearance. He had startling blue eyes that were a contrast to his almost black hair that was artfully messed beneath a nurse hat and the bright red lipstick spread over his gorgeous lips. He was about the same height as Dean but Dean was slightly taller and given by the soft features of the other teen, a little older. Dean's eyes raked over the teens form taking in the tight white blouse with a red trim that was unbuttoned to show a teasing amount of chest before moving lower to take in the long smooth legs that had obviously been shaved for the occasion before finishing at the black pumps that accounted for his height. It was obvious by the way the teen was stood that he was confident in his outfit but as Dean's eyes trailed back up to the teen's face, he smirked as he saw the scarlet blush that had filled his cheeks as he noticed Dean's stare. With the window open, Dean made his move.

"Hey I'm Dean" he greeted with his winning smile that never failed to get him laid.

"C-Castiel" the other boy stuttered and Dean couldn't find it utterly adorable.

"Well Cas, let me get you a drink" just as Dean went to move to get another cup, Cas spoke.

"Thank you but I don't drink" the boy said timidly.

"Oh come on. You're at a party. Surely one drink couldn't hurt?" Dean knew it was peer-pressure and he normally wasn't one that pressured people into doing something they didn't want to but the guy looked as if he was wound so tight and needed to let loose a little. The younger teen bit down on his lower lip chewing on it in deliberation before relenting and giving Dean a shy smile and nodded. As one drink turned into two and two turned into three, Dean discovered why Cas would rather not drink. The teen turned into a clingy, touchy drunk not that Dean minded one iota because it was him who Cas decided to hang off.

They sat on a couch in the living area which was filled with dancing bodies with Cas pressed into Dean's side as close as physically possible with Dean's arm draped over his shoulder Cas' hat nowhere in sight. He was whispering random facts about bees into Dean's ear and Dean couldn't help but laugh at how cute it was. It was strangely endearing and Dean found himself hooked to the strange teen. They had chatted over their drinks getting to know each other more and as they did, Dean found himself being drawn in by the teen's strangeness and unique approach to things. Dean had assumed correct in thinking the boy was younger and found out that he was a sophomore at Jo's school whereas Dean and Jo were both seniors. The night moved onward as Cas downed the rest of his drink marking his fourth of the night. With it Cas' forwardness increased and Dean's free hand that wasn't wrapped around Cas was taken by Cas' and placed onto the younger boy's inner thigh. Dean inwardly groaned at the smoothness under his fingertips as Cas slid his hand higher and underneath the hem of the mini skirt. Cas' hand stopped moving Dean's and Dean didn't dare move it any higher.

"Can I tell you a secret?" Cas whispered into his ear.

"Mmm? And what's that baby?" Dean hummed in reply which earned a giggle from the teen. Before Dean's alcohol clouded mind could register what was happening, Cas moved to straddle Dean's lap his knees pressed either side of Dean's hips with his hands on his shoulders. Dean's body reacted faster than his brain and moved his hands to grip Cas' hips.

The younger teen moved in so his breath was ghosting over the shell of Dean's ear causing a shiver to pass down his spine. "I'm wearing panties" he breathed before he gripped Dean's hand and slid it up his thigh so his fingers pressed against silk fabric. Dean let out a small groan when he felt them while Cas let out a small sigh while pressing Dean's hand further up his leg so Dean's fingers were pressed up against his crotch. "I want you to bend me over and fuck me in them" Cas demanded into Dean's ear.

Dean didn't waste a second. He moved his hand from Cas' hip and placed it into the brown locks where he pulled tight which forced Cas' head back so Dean could look him in the eye. As soon as he could see him, he leant in and placed his lips onto the other teen's. When Dean licked along Cas' lips he couldn't help but groan as the other teen opened up so willingly for him to enter his mouth. His tongue plunged inside mapping out every nook and cranny and the spots that made Cas' hips buck into Dean's. As Dean's tongue explored, Cas' hips continued to rock into Dean's until the friction was too much and not enough at the same time. Dean yanked on Cas' hair pulling the teen away from him and smirked at the whine the nurse let out.

"How 'bout we find somewhere a little more private?" Dean purred into Cas' ear who quickly nodded before gracefully sliding off Dean's lap and stood to his feet. Their twin erections were glaringly obvious along with the red lipstick that was no doubt smudged across Dean's lips as they walked towards the back of the house where the bedrooms were located. Cas led the way as he had told Dean earlier that the person throwing the party was a close friend of his so he knew where to go. Dean didn't mind one bit as he followed Cas through the house unashamed to be openly staring at Cas' ass. Once or twice Cas had turned around and caught him staring only to blush a deep red and turn back to look where they were walking. No one bothered them as they walked and soon enough they were stepping into a dark bedroom with a double bed in the middle. "Whose room is this?" Dean asked not really caring for the answer but curious all the same.

"My friend's, Gabriel" Cas replied with a smirk while he shut the door and moved towards Dean confidently even while still wearing the black heels. "He's a bit of an ass at the best of times." Dean let out a chuckle at that and saw that it had Cas smiling at him.

"Well then, let's deface his bed" Dean said with a grin before cupping Cas' cheek and guiding their mouths together. Cas moaned into the kiss as his hands cupped Dean's cheeks. Cas moved away prematurely and Dean frowned in confusion before his hands came up to remove the mask that was over his face and threw it aside. With the mask removed, Dean leant forward again and pressed their lips together again already addicted to the taste of Cas. As their tongues tangled, Dean walked them backwards towards the bed where he sat down and pulled Cas into his lap just like they had on the couch. His hands rubbed up the smooth texture of Cas' thighs and stroked teasingly over the fabric of his panties.

When the need to breathe became a necessity, Cas pulled away and slipped off Dean's lap where he parted Dean's legs so he could nestle between them. Nervous hands fumbled with the zipper and Dean ran his hands through Cas' hair in a soothing gesture to calm the teen. Dean hissed when a warm hand wrapped around his dick and pulled him out into the cool air but any thought other than Cas was pushed from his mind as the teen looked up at him through his lashes as he wrapped his smudged lipstick clad lips around his cock.

"Fuck" Dean groaned as Cas' tongue swirled around the head his fingers clenching tightly into the locks beneath them. His cheeks hollowed as he sucked and glided his lips lower taking more of Dean into his mouth. "Jesus" he panted as Cas continued to slide until his nose was pressed into the brown curls at the base. Cas never moved his eyes away from Dean's as he sucked so eagerly on the dick in his mouth and Dean found he couldn't look away caught in a trance of pleasure. Cas pulled back up to the head and rolled his tongue over the slit lapping at the pre-cum before swiping along the bundle of nerves under the head. Dean's eyes nearly rolled back into his head as Cas worked on trying to suck him off but Dean wasn't going to give him the pleasure of tasting him. Not yet anyway.

He pulled harshly on the hand that was locked around the brown hair yanking Cas off his dick with a wet pop. The needy whine Cas let out had another pearl of pre-cum drip from the tip. Cas eyed it with wide eyes as he licked his lips. Dean followed his line of sight and smirked before moving his free hand to swipe a finger over the drop and reached it towards Cas' mouth. The teen eagerly grabbed on and sucked on Dean's finger. Dean pulled back after a moment before slipping two fingers inside which Cas easily swallowed around his tongue working over the digits just like they had to his cock just minutes ago.

"That's enough" Dean growled and Cas obediently let the fingers slip from his mouth which had Dean letting out a small groan "Fuck you're so obedient aren't you baby" Dean praised before he pulled at Cas and settled him in his lap once again. They kissed some more Dean savouring the taste of himself on Cas' tongue before he pulled away and turned them so Cas was settled on his back. Dean buried his face into Cas' neck biting and licking his way down the expanse of skin. Cas was letting out needy little whines as his hips bucked up into Dean while he worked. "Needy little thing aren't you?" Dean teased while he worked on the buttons of the tight white blouse. Cas' chest was heaving as Dean worked staring down at the newly revealed skin with hungry eyes. He wanted nothing more than to taste and mark every inch of skin that he could but it would have to wait for another time because he was unbelievably turned on and there was no way he could wait much longer.

With the buttons undone, Dean lifted Cas up to remove it from his shoulders before he undid the button of the skirt and slipped it down Cas' legs to reveal the black silk panties that were straining to keep him held inside. He threw the skirt in the general direction he did the shirt while his hands gently slipped the heels from Cas' feet and let them fall to the floor with a thud but his eyes were still firmly locked on the black panties. There was a large damp spot in the front from where he had started to leak through and Dean couldn't help himself as he leant down to suck at the spot. A cry of Dean's name filled the room as he mouthed at Cas' cock through the fabric which had Dean grinning before pulling back.

"Hands and knees" he demanded and Cas scrambled to comply positioning himself as Dean had instructed with his head buried in the pillows. He was shaking where he sat with need and Dean pitied him slightly. "So fucking gorgeous you know that?" he praised as he worked on the tie of his cape and let it fall to the floor. Next to go was the shirt followed by his jeans and boxers. He searched for his wallet in the back pocket of his jeans and removed the small packet of lube and the condom he always kept in there for situations exactly like this one. He threw them on the bed close to Cas who looked down at them and visibly shivered in anticipation. Dean slid onto the bed on his knees and inched closer to Cas where he positioned himself between his spread knees.

When his hands pressed against the teen's back, Cas pressed back into the touch a silent plea for more. Dean was more than happy to move things along and slowly slid his hands down to the waistband of the panties. He pulled them down and over the globes of his ass and nestled them below his sac. Cas gasped at the touch but didn't utter another sound as Dean grabbed hold of the lube. He ripped open the packet and squirted half of the liquid onto his fingers where he rubbed them together to warm them up. Once satisfied, he pushed at Cas' knees with his dry hand in indication to spread them wider. Cas did so which exposed the pink rim of his hole which looked virgin tight. Unable to control himself much longer, Dean raised his dry hand to Cas' hip while his lube slick fingers traced over the rim. Cas groaned and pushed back against the touch.

"Please" he whined while Dean continued to tease. "Dean, please" he said again when Dean made no move to enter him.

"Such a needy little slut aren't you Cas" he teased while he watched his fingers as they played with the tight muscle before he slipped the first finger in easily watching as Cas' body sucked him in eagerly. Cas' head hung low as Dean's finger worked inside him and his hips tried to fuck back onto the digit only to be held in place by Dean's hand. Castiel let out a grunt of frustration as he resigned to the fact that he had to stay still which had a low chuckle escaping from Dean.

"More" Cas demanded and Dean was well over teasing now. He slipped another digit in and was surprised by the lack of resistance to his digits. His fingers slid in and out easily without much complaint from the teen below him instead he was groaning into the pillow below his face and his fingers were clenched into the sheets.

"You finger yourself before you came baby?" Dean asked as he slid in another finger. Cas nodded and let out a little whine as Dean spread his fingers wider "Expecting to get lucky huh Cas? Bet you were picturing a fat cock in your ass as you did it. Dressed up like a slutty little nurse just begging to be fucked aren't you?"

"Yes!" Cas keened "Please Dean. Fuck me. Want it so bad"

"I know you do baby" Dean taunted as he pressed his fingers against the bundle of nerves he had been purposely avoiding. He watched as Cas bowed into the touch and let out a high pitched yelp at the sensation. His muscles clenched around Dean's fingers and Dean couldn't stop the groan that was let out as he imagined his dick being inside the heat. Dean pulled his fingers free watching as Cas clenched absently around the emptiness while he blindly reached for the condom. He tore open the package and rolled it on before retrieving the half empty packet of lube and smothering it on his dick. He couldn't help but groan at the pressure as he stroked himself taking the edge off slightly after having ignored it for so long. Satisfied he was slick enough, Dean placed both his hands onto Cas' hips and lined up with his stretched entrance. Dean didn't even have to wait before Cas was sliding back onto him with such a force that he was sure it was going to hurt him but the high pitched moan that he let out told him otherwise.

Dean's balls slapped against Cas' ass as he bottomed out and he had to grip tighter onto Cas' hips to stop him from moving. Sure Cas seemed to be okay but Dean was so close to the edge he just needed a minute or it was going to be over way too soon.

"Dean" Cas whined "Dean move"

"Hold on baby" Dean panted "I need a minute" Cas obliged although he started to clench his muscles around Dean and Dean growled at the motion which earned him a small smirk from Cas over his shoulder. "Little shit" Dean snarled before he pulled out and slammed back in which had Cas keening into the air.

"Fuck" Cas gasped as Dean repeated the motion over and over pulling Cas' hips back onto him as he thrust forward. Needy little pants of air fell from Cas' lips as they moved together along with a string of curses and Dean's name. "Fuck… harder Dean" Cas pleaded his fingers clenching even harder into the sheets causing them to bunch under his palms. Dean snarled as he picked up the pace before he pushed Cas' head down into the mattress to change the angle and give himself more leverage. Dean pushed himself to his feet slightly so he could slam into Cas even harder. Cas had turned his head to the side so Dean could still hear the breaths being punched out and the gasps to catch it again. "Oh god Dean" Cas panted as he writhed and clenched down hard on Dean's cock.

"Just can't get enough can you Cas? Such a greedy little slut bet I could just stop right now and you'd keep fucking yourself to get more" Dean grunted as he continued to pound into the tight heat his hand still pushing Cas' head into the mattress. He knew by the way Cas was groaning and clenching that he was close and Dean wasn't doing much better himself. It was going to be over soon but he was going to make sure Cas got there first. Dean repositioned to his knees and draped himself over Cas' back his hips continued to rock as he reached around and slid his hand into the silky panties where he pushed them down to Cas' thighs before he fisted Cas' hard cock. Cas groaned as Dean took hold and started to strip him in a tight fist. Cas' hips were rocking back and forth between Dean's cock and his fist. "Come on Cas. Fuck yourself on my dick. Get yourself off and cover yourself in cum. Do it baby" Dean whispered into Cas' ear before he moved to suck on his neck leaving a bright red mark which he soothed with his tongue while Cas' hips continued to move doing exactly what Dean had asked. "Mmm just like that baby" Dean cooed into Cas' ear.

Dean felt the urge to come build higher and higher in his gut until he couldn't take the pace much longer and started to slam his hips harder into Cas. Cas moaned in approval and Dean just pumped harder. They moved in tandem with Cas still fucking his hips back onto Dean's cock when Dean pulled back and his hand still stripping Cas' cock but the pace was erratic and electric sending pulses of pleasure through Dean until final Cas gasped out his name and came all over his hand and over the sheets below him. The pressure around his dick had him crying out Castiel's name while his hips stuttered and he came into the condom.

Panting, they both came down from their highs as Dean pulled out and collapsed to the side while Cas slumped down and stayed lying on his stomach. After Dean had caught his breath, he looked to the side to see Cas smiling shyly at him. Dean eagerly returned the smile before he raised his arm closest to Cas and reached over to pull the other teen towards him. Cas came willingly and snuggled into Dean's side with his head rested over Dean's heart.

"I gotta ask man," Dean said breaking the post-sex haze "Why a nurse?"

It was then the story came out that Cas' parents thought he was studying at Anna's house and how Anna had organised their costumes. Cas had a thing for cross-dressing and everyone knew as much so it wasn't a big deal for him to show up at a party wearing a skirt and heels. When Cas confessed that Anna had only provided the skirt and blouse the rest was from his own wardrobe, Dean's thoughts went to a dangerous place where he thought of what else Cas had in that wardrobe. It was dangerous territory at the time as Dean had never been in a committed relationship and he didn't even know if Cas wanted more than what they had that night. So to test the waters, Dean decided to subtly hint at wanting to see Cas again.

"Maybe you'll have to show me the rest of that wardrobe of yours?" he asked while he stared at the ceiling. The hand that had been tracing over his abdomen stopped and Dean felt the pressure of Cas' palm before the teen was rising up to look at Dean.

"You want there to be more than this?" Cas asked with his head tilted adorably to the side and Dean almost melted on the spot at the hope that glistened in his eyes.

"Yeah" Dean said his throat tight "Yes I do" he said again after clearing his throat. Cas had attacked him with kisses then leaving a hickey of his own into Dean's neck low enough for him to hide and another just below his ear which would be a lot harder to cover up.

After some more hefty making out, they were rudely interrupted by a cellphone ringing. Cas groaned into the skin he was working over on Dean's neck before he pushed himself up and fixed his panties back into place before he slunk off the bed to ransack through his clothes before he found his phone. He pulled it out and grimaced at the screen before answering it. It had been his mother asking him to come home and Cas had said he would be home soon they just had a few things they still needed to do for their assignment but he would text them when he left. Dean had tried to hide the hurt but apparently he wasn't very good. Cas had moved back to straddle him and placed a heated kiss to his lips which had promised more before he pulled back again and slowly started getting dressed. Dean watched idly from the bed as the skin he had been touching and licking was slowly covered up once again. He was confused for a moment when Cas searched through the drawers next to the bed but when he pulled out a pen and grabbed Dean's arm, he knew what he was doing. Cas wrote down his number onto Dean's skin and when he was done, Dean stared at the numbers and committed it to memory.

The next morning, Dean had called Cas and the rest was history. They would meet up after school with Dean picking Cas up after his various after-school commitments and they'd spend the evening together driving around in the impala and finding a secluded spot where they could do what they like. Of course not every time they met they would have sex as there were times when they would just go to a diner and talk over a meal. It was peaceful and it was perfect. Eventually, after two weeks of them being an item, Dean dragged Cas home to meet his family who welcomed him with open arms. His parents were accepting and didn't bat an eye at Cas the first time he decided he wanted to wear lipstick while he was over. But now it was Dean's turn to meet Cas' parents. They had put it off for so long because Cas was worried his parents wouldn't be accepting of Dean. His parents knew that Cas was seeing someone and had told Cas that they would like to meet him a month into their relationship but Cas had put it off saying it wasn't very serious even though that was far from the truth seeing they had talked about a future together. However, now that they were three months in, Dean had finally talked Cas around into meeting his folks. It was how Dean found himself driving over to his boyfriend's house nervous as hell that everything was going to crumble around them and Cas would be forced to leave him and not even the thoughts of their first night together was calming the pit of worry in his gut.

A/N Second part will be Cas' POV of the dinner :) Leave a review if you feel inclined :P