Fic: Pretty In Pink
Nov. 2nd, 2020 09:10 pm![[personal profile]](https://www.dreamwidth.org/img/silk/identity/user.png){kind=small}
ellerkayTitle: Pretty In Pink
Pairing: Dean/Sam/Castiel
Rating: Explicit/NC-17
Genre: Slash
Word Count: 5700
Disclaimer: All for fun, none for profit.
Summary: Dean has a secret: he loves to dress up in women's clothes. When Sam catches him at it, Dean fears Sam and Castiel's reactions to this hidden part of himself.
Warnings/tags: Incest, crossdressing, polyamory, human Cas, shame, acceptance, fluff and smut, hand job, oral sex
A/N: Written for the![[livejournal.com profile]](https://www.dreamwidth.org/img/external/lj-community.gif)
spn_reversebang. Thanks to the incredibly talented claraxbarton for providing the beautiful inspiration for this fic! Huge thanks as well to my beta, the amazing ![[livejournal.com profile]](https://www.dreamwidth.org/img/external/lj-userinfo.gif)
jj1564! Your comments and suggestions were invaluable.
Art: Imgur
Read on AO3
***
Dean lay on the Impala’s hood, head resting on his clasped hands, elbows splayed out. He stared dreamily at the ceiling of the garage in the Men of Letters bunker, not really seeing it. He felt the cool of the Impala’s windshield beneath his shoulder blades, above his pink corset. Baby’s waxed hood was pleasantly smooth and a little slippery under his feet, which were encased in stockings. He didn’t think about anything, just enjoyed the sensations.
There was something about being dressed like this that always somehow both excited and relaxed Dean. It let him turn his brain off like few other things did. Before, he’d get shaky with anticipation; after, he’d have to deal with the shame. But when he was in women’s clothes, Dean just felt good. A little dirty, in a fun way. And, as much as he always tried to suppress the thought, whenever he was in a garter belt or panties or whatever, he felt…pretty.
He’d never told anyone about this; not even Sam and Cas, and they were his whole fucking world. He tried to justify it to himself; this was his secret, his thing. He was allowed to have his own thing.
Which would have been fine, except that a part of Dean actually really wanted them to see him like this. He wanted to see love on their faces and desire in their eyes at this part of him, too. But every time he thought about telling them, Dean felt sick. It wasn’t that he thought they were prejudiced; and, in theory, there was nothing wrong with a little cross-dressing – for other people.
But other people weren’t Dean. He’d spent his life building his image as a cool, tough guy. He imagined the shock and confusion he’d see on Sam and Cas’ faces if he ever told them. They wouldn’t understand. Hell, Dean didn’t even understand it. And what if they were mad that he’d never told them? Not only did he run the risk of fucking stuff up with them, he could lose the refuge that wearing these clothes provided for him.
No; Dean would never tell them. He stretched his arms out, popping his shoulders, and kicked his feet gently, contented. He rubbed a hand over his bare thigh, thinking about jerking off. It was always extra hot in girl clothes. Sam and Cas had gone out for dinner and wouldn’t be home for hours. He had plenty of time to –
“Dean?” Sam’s voice came from the corridor. Dean’s eyes widened in panic. He sat up and scrambled down the hood of the car, almost falling off in his haste to get up. He looked around desperately, but he had left his regular clothes in his room.
“Dean, are you in here?” Sam again, closer now – he was in the hallway outside the door to the garage. Dean opened the Impala’s door and got inside, slamming it shut behind him. He looked in the backseat for a blanket or something – anything – he could use to cover himself up, but there was nothing. He sank low in his seat and prayed Sam wouldn’t come over.
“There you are,” Sam said, entering the room. “Didn’t you hear me calling?”
“Sorry, I had music on till a second ago,” Dean said. “Look, I’m in the middle of something, so – ”
“Are you okay?” Sam said, voice concerned. “You sound weird.”
“I’m fine, man, just gimme a second – ”
But Sam was already at the window. “You’re just in the Impala,” he pointed out. “What’s – ”
He fell silent as he peered down at Dean. Dean swallowed and forced himself to look into his brother’s face. Sam was frowning in puzzlement and he looked slightly surprised, which was better than the abject horror that had long haunted Dean’s imagination.
Sam was silent for what felt like an eternity but was probably only a few seconds. “Okay, Dean,” he said finally, in a gentle tone. “Take all the time you need. The restaurant Cas and I were gonna eat at was closed, so we’ll be in the kitchen.”
He smiled softly at Dean and left the room.
Dean leaned forward and rested his head on the steering wheel, wondering how hard it would be to find and perform a memory spell that would wipe both him and Sam clean of the last two minutes of their lives.
***
Dean made himself wait five minutes before getting out of the car. He listened at the doorway for any sound of Sam or Cas nearby, then sprinted to his room and got changed as quickly as he could. He very seriously considered barricading himself in until the next morning. This was supposed to be Sam and Castiel’s date night, after all. But finally he decided that might make things feel even worse and weirder, so he forced himself to go to the kitchen, say hi, and grab some food before leaving them alone.
They both greeted him perfectly normally. Dean did his best to give the appearance that he was totally fine and not dying a thousand deaths inside. He thought Sam’s gaze lingered on him longer than usual but couldn’t be sure. Well, if that was the worst thing that happened because of this, Dean would consider himself damn lucky.
***
It was not the worst thing that happened. Dean had to spend the next two days avoiding Sam and Cas as much as humanly possible, because he simply did not know how to act around them anymore. Sam knew, and if Sam knew he must have told Cas. Dean felt like he had been flayed alive. This deep, shameful secret exposed to the light. It felt like when he’d told Sam about Hell; except that had actually been better in some ways, because he’d made a conscious choice to tell Sam about it. Yeah, “I like to wear ladies’ clothes sometimes” wasn’t exactly the same as “I spent a decade cutting people up,” but still. At least in Hell there had been circumstances. He’d come to like dressing up all on his own.
Finally, on the afternoon of the third day, Sam knocked on Dean’s bedroom door.
“Come in,” Dean called with forced casualness.
Sam opened the door and took a step inside. “Hey,” he said. “Tonight’s our date night. What do you want to do?”
Panic gripped Dean’s heart. “Oh, uh,” he said stupidly. “Listen, I’m actually not feeling so great.” He coughed dramatically. “I think I might be coming down with a cold. I don’t want you to catch it. You and Cas can take the shared room tonight if you want.” They each had their own rooms in the bunker, but there was also a bedroom they’d set up for all three of them, or when any two of them wanted some alone time.
Sam’s expression morphed into one of sadness. He took another step inside and closed the door behind him. Dean could feel his fear mounting.
“Dean,” Sam said, then hesitated. He looked like he was considering his words very carefully. “Listen, I don’t want to force you into anything you don’t want to talk about, or share. But I…I want us to be okay, too. You’ve seemed pretty upset these past few days.”
Fuck. Damn it. Why did Sam always know?
“And I want you to know,” Sam continued, “that I don’t think you have anything to be embarrassed about. Or ashamed of. Not that I’m saying you are – but if you were, you have no reason to be.”
Dean could feel his face going bright red as he stared at Sam, unable to speak. Sam glanced briefly into his eyes, then away.
“I just want you to be able to be around me,” Sam said, mouth turning down at the corners. “But if you need more time before you’re ready, that’s okay.” He turned to go, reaching for the door handle.
Dean simply could not stand for Sam to look that sad and for him to be the cause.
“What did Cas say?” were, bizarrely, the words that seemed to explode out of his mouth.
Sam turned back to him with a puzzled frown.
“When you told him about me,” Dean clarified. “What you saw.”
Sam’s frowned deepened. “I didn’t tell him,” he said, sounding surprised. “It’s your thing. It’s not my place to tell him.”
“Oh,” Dean said lamely, looking down at his bed. He couldn’t decide if this was good news or bad news. It had been horrible thinking everyone knew, but also, at least he didn’t have to have any awkward conversations.
Except that, obviously, he totally did.
“I – ” Sam hesitated again, then kept going. “I wouldn’t really know what to tell him, anyway. I mean, I know what I saw, but I don’t know what it means, for you.”
Dean leaned back against his headboard with a long-suffering sigh, scrubbing a hand across his face. “It doesn’t really mean anything.”
“No?” Sam was looking at him with that same careful, gentle expression. It was starting to annoy Dean.
“No,” he said. “And quit looming over me and looking at me like I’m going to break, would you? Sit down.”
A small smile flitted across Sam’s face. He took a seat at the edge of Dean’s bed.
“So, you’re ready to talk about it?” he asked.
“No,” Dean shot back. “I am absolutely, one hundred percent, not ready for this little chat. But it looks like it’s going to happen anyway.” He took a deep breath and tried to organize his thoughts. “Okay, so, when I was nineteen, right, this girl I was hooking up with got me to try on her panties. And I – I kinda liked it.”
Sam nodded, expression neutral.
“I wasn’t, you know, planning to make it a habit or anything. But I kept thinking about it, and finally, one day, I bought a pair of my own.” Dean tried to grin. “They were way too fucking small. Women’s sizes are super weird.”
Sam smiled.
“Awhile later I bought a bigger pair and managed to get the sizing right and I…put them on and…” Dean exhaled sharply. “I dunno, Sammy, I just liked how I felt. It felt…different.”
“More like yourself?” Sam suggested.
Dean shook his head. “No, look, I’m a guy, okay? It’s cool that some people with junk are ladies, but that’s not me.” He paused, frowning. “If anything, I guess I liked how I felt like a different person. It was kind of an escape, in a weird way.” He shrugged. “And from there it sort of spiraled. I mean, it’s not like I have a huge collection of stuff, not with the way we moved around.” He’d started to accrue a bit more now that they had the bunker to store it in, but Sam didn’t need to know that right now. “When I got time to myself, I just – dressed up.”
“And you never told anyone?”
Dean shuddered. “No fucking way. I mean, don’t you think it’s kind of ridiculous? Dean Winchester in a garter belt and shit?”
“No,” Sam said quietly. “I don’t think it’s ridiculous at all.” He paused, biting his lip. “I think you looked great,” he finished finally. “I mean, not that I got much of a look, but from what I could see…”
Dean could feel his face getting redder, if that was even possible.
“Yeah?” he managed to choke out.
“Yeah,” Sam said.
He met Dean’s gaze. Dean was thunderstruck to realize his brother’s pupils were slightly dilated.
“I’d love to see it again,” Sam said, words coming out in a rush. “Only if you want to let me, of course. If it’s your thing that you want to keep to yourself, I understand. But if you want to share it…” He exhaled in a shuddery breath. “I’m interested.”
For a moment Dean could only stare at Sam, excited and overwhelmed and completely not ready to seriously consider that at this moment. Finally he nodded a bit too quickly.
“Okay, man,” he said. “Cool, thanks, that – that means a lot.”
Sam nodded back and they fell briefly silent.
“Will you tell Cas?” Sam asked.
Dean groaned and rubbed his temples. “Yeah,” he said finally. “I’ll tell him. I don’t want to force you to keep a secret, and if you know, he might as well know.”
Sam smiled. “Okay,” he said, rising and extending his hand. “So, should we grab some dinner?”
Dean let Sam help him up. “Burgers. I deserve burgers after dealing with this conversation.”
Sam chuckled. “Anything you want.”
***
It took a day for Dean to psych himself up, but he finally managed to tell Cas his secret. Castiel listened attentively, head tilted slightly.
“All right,” he replied when Dean had finished.
Dean blinked. “‘All right?’ That’s all you have to say?”
“Dean, I am very used to you doing illegal activities.”
Dean spluttered. “What?! It’s not illegal!”
“Immoral?”
“No! I mean, some people think so, but some people are stupid.”
“Then why was it a secret?”
Dean shook his head, trying to figure out how to explain this. “It’s – it’s – it’s kind of weird, okay? Most guys don’t wanna wear women’s clothes!”
“Oh.” Castiel looked vaguely irritated. “This is a gender thing.”
“Yeah, it’s a gender thing.”
“I don’t understand gender.”
“Cas, you’ve been human for a couple years now. One of these days you’re gonna have to figure out gender.”
“Why?” Castiel sounded a little belligerent, but because of exasperation and confusion, Dean thought. He was tilting his head at Dean again.
“Because it’ll make things easier for you,” Dean replied.
Castiel frowned. “It doesn’t make any sense,” he said. “You say that most men do not wear women’s clothes, but in other societies and throughout human history, what men wore would look more like a skirt or dress to your eyes. The behaviors you associate with masculinity or femininity are constantly being performed by the one who is not ‘supposed’ to do it.” He raised his fingers in air quotes around ‘supposed.’ Dean rolled his eyes. “They also vary widely across history and cultures. I say that your narrow definitions of gender are foolish and illogical and serve no one.”
“Well, welcome to being human,” Dean snapped.
Castiel took a breath, his face softening. “What I am trying to say, Dean, is that I do not care what you wear.”
“Oh,” Dean said. He’d half-forgotten why they’d started this conversation. “Right. Thanks, Cas.”
Castiel touched Dean’s cheek and kissed him gently. “In fact, I would imagine that you look very aesthetically pleasing in those sorts of garments.”
He gave a sweet little smile as Dean blinked down at him, unable to think of a thing to say.
***
Dean’s birthday was a few weeks after these conversations had taken place. Sam and Cas hadn’t brought the subject up again, for which Dean was profoundly grateful. He was glad they knew, but he was still figuring out what – if anything – he wanted to do about the situation.
He hadn’t dressed up since he’d been caught. Partly because it felt weird, but mostly because he kept thinking about how Sam and Cas had seemed interested in seeing him that way. He wasn’t sure he could trust it. Not that he thought they were lying, but maybe they were only being polite.
Dean pushed these thoughts away as he enjoyed his birthday meal and pie. Sam disappeared after his slice, allegedly to get himself another cup of coffee. He came back with a large box instead.
Dean blinked at him. They’d only even started doing birthday meals a couple years ago. Presents hadn’t become a thing at all. Maybe something small and jokey. Not a large gift like this appeared to be.
Pushing away his confusion, Dean eagerly tore off the wrapping paper and opened the box. Inside were boots – shiny black vinyl knee-highs with big, chunky heels. Dean stared at them, his eyes going wide and his heartrate shooting up. They were beautiful, but he wasn’t sure whether to thank Sam or run for the hills.
Dean looked up at his brother; Sam looked eager, but guarded.
“It’s okay if you don’t like them,” he said immediately. “They’re returnable. I don’t know if they’re your style or anything you’re interested in, but I found this place online that sells this kind of shoe for bigger feet, and I thought…” He gestured randomly. “I thought maybe you’d like them.”
Dean swallowed around a sudden lump in his throat. “They’re great,” he managed to choke out. “Really, Sammy. Thank you.”
Dean glanced over at Cas, who was smiling. Dean realized he had pulled out a box from somewhere, too. Castiel pushed it across the table to Dean. It was much smaller than the shoebox, though hardly tiny.
“I got you something, too,” Castiel said.
Feeling a little nervous that there was a theme coming, Dean silently unwrapped and opened the box. Indeed, it was full of makeup. Dean stared at it.
“I can return this as well,” Castiel said, uncertainly.
“We weren’t sure if you were interested in makeup, either,” Sam said, sounding apologetic. “It’s really not a big deal if you’re not.”
Dean cleared his throat. “Uh, I mean, maybe,” he said. The truth was, he was very interested in makeup. But the one time years ago that he’d tried a little lipstick, the results had been so disastrous that he’d thrown it out and vowed never to go that route again. “I just – I don’t really know how to do that stuff.”
“Oh, that’s fine,” Castiel said, relief in his voice. “I can put it on you.”
Dean frowned at him. “Since when do you know how to use makeup?!”
“There are many tutorials on YouTube,” Castiel replied. “I have learned a lot. I believe I can make you look very glamorous.”
Dean couldn’t help but laugh at that, as much to release tension as in response to what Castiel had said. Sam and Cas smiled with him.
“Of course, you could play with the makeup on your own, too,” Sam hastened to add. “Whatever you want.” He paused for a long moment. “I don’t know if you decided you wanted to keep this private, or if you’re still thinking about it…” He trailed off, trying and failing to look casual. Dean could see the contained desire in Sam’s slightly too-wide eyes, in the bobbing of his Adam’s apple as Sam swallowed reflexively. It made Dean’s breath catch as he thought about it. Thought about showing off for them.
Dean looked to Cas, who was smiling fondly at him. Of course, Cas didn’t see anything unusual or taboo about this, so it probably wasn’t the same turn-on. But he’d sounded genuinely interested in the aesthetics when Dean had told him about it.
“Well,” Dean said in a thick voice. He rose suddenly, chair scraping out from under him. “I – I guess I’ll go try on the boots, then, and you guys can tell me how they look.” He half-fled to his room without a backward glance, heart hammering in excitement and fear.
***
Dean pulled out all his special clothes and laid them on the bed. He dithered over them for a full five minutes, even though he didn’t actually have that much stuff, before finally deciding to wear the pink corset, pink panties, and stockings with garters combo he’d had on the day Sam caught him. He’d been wondering ever since what Sam would think if he got a real look at Dean in that getup.
Well, now was his chance to find out. Hands shaking a little, Dean took off his regular clothes and got into the other ones. Last of all, he pulled on the boots. They fit like a dream.
Dean stood up slowly. He’d bought heels a few times, but never worked up the courage to try the shoes on in the store and so he kept getting bad fits. The one time he’d gotten close, he’d fallen over after a few steps and decided to give it up.
But Sammy’d taken care of him, somehow finding the perfect shoes for his feet. And the chunky wedge heel meant that walking wasn’t too difficult. Dean couldn’t help wondering if he could eventually learn to walk in sexy stilettos, but firmly pulled his thoughts back to the present. No good running before he knew he could walk in these way easier ones.
Dean took a few turns about the room, feeling pretty comfortable pretty fast. He turned towards the door and took a deep, steadying breath. He felt okay walking in them, anyway. Showing them off – all of this off – to Sam and Cas was a whole different manner.
“What the hell,” he muttered aloud, with more confidence than he felt. Trying to convince himself. “What are birthdays for, right?”
Dean opened the door and walked towards the map room. The hallway had never felt so long. Dean had never felt so exposed. It was terrifying, but it was exciting, too. He was way too nervous to get hard, but he could feel just the beginnings of arousal low in his pelvis.
“Okay,” Dean called, as he approached the entrance to the map room. “I’m coming in, so, uh, brace yourselves or whatever.”
Suddenly, deliriously, Dean decided he should just go for broke on this. He raised a hand above his head and rested on the doorframe, leaning into it, putting his other hand on his hip, elbow bent.
“What’s up, sailors?” he said, and then felt absolutely ridiculous. Was he out of his mind? Saying that? Dressed like this?
But it was too late. Cas and Sam were looking at him and they had most certainly heard him.
Castiel’s face broke out into a smile that made the corners of his eyes crinkle. “Dean,” he said happily. “You look beautiful.”
Dean could feel a flush creeping up his chest and neck at the unexpected word. “What? Shut up, no I don’t,” he said automatically, but the words lacked bite. Castiel just nodded as though Dean had agreed with him.
Dean’s blush deepened as he looked at Sam. Sam’s mouth had gone slack as he looked Dean up and down with an unmistakable expression of hunger.
“You look amazing,” he said finally, voice low. Dean gulped, the stirrings of arousal a little more insistent now.
“I see that the boots fit,” Castiel said, as if this was just a normal pair of shoes.
“Uh – yeah!” Dean said, looking down awkwardly at the gorgeous boots. He looked back up at Sam, giving him a lopsided grin. “Thanks, man. They’re great.”
“Would you like to try the makeup, as well?” Castiel said.
“Only if you want to,” Sam added hastily. Castiel gave him a look.
“Of course, only if he wants to. That’s why I asked if he’d like to.”
Sam’s dimples flashed. “There are nuances of politeness and obligation, Cas, since you gave him the makeup as a gift, and he’s tried on my gift. I can tell you more about it later. I just wanted him to know it was really okay if he didn’t want to do the makeup.”
“Oh. Thank you.” Cas turned back to Dean. “Yes, please do not feel obligated, Dean.”
Dean’s brain had stuttered at the thought of the makeup and was just now catching up with things again.
“Makeup,” he said dumbly. “Yeah. Fuck it. Let’s do this.”
***
The three of them moved to the large bunker bathroom. Castiel had Dean sit down sideways on a bench, straddling it. But before Cas could sit in front of Dean, Sam grabbed his arm.
“Hang on,” he said. “It’ll be easier if I shave him first.”
“I can shave myself,” Dean protested.
Sam raised his eyebrows at him. “Well, you can if you want,” he said. “But you usually use an electric razor, and it’ll be a closer shave if you let me do it with an actual blade.” He smiled softly. “And, it’s your birthday. I want to take care of you.”
Dean blinked and, after a second, nodded mutely. He watched Sam gather supplies: safety razor and shaving cream and a small basin which Sam filled with warm water. When he was ready, Sam stood before Dean, towering over him. Sam lathered Dean’s face and then went to work. He was careful and methodical. Dean found himself relaxing, lulled by the warmth of Sam’s hands and the gentle scraping sound of the razor on his skin in the otherwise silent room.
It seemed like no time at all before Sam was running his fingers gently over Dean’s cheek and chin to check for missed spots. Sam pronounced his work done and Castiel handed him a damp, hot towel. Sam scrubbed it gently over Dean’s face before patting his skin with a dry one.
“All the videos say moisturizing is important,” Castiel said, a trifle anxiously. Sam grinned.
“Dean has a bottle in the cabinet behind the mirror,” he said.
“Dude, shut up,” Dean muttered. Sam ignored him and took the bottle from Cas, applying the lotion over Dean’s face.
Finally, he stepped back. Castiel took a seat in front of Dean and got to work. Sam began prowling around, circling them slowly as he watched.
As the actual makeup application began, Dean’s relaxation from the shave faded. He was so freaked out and turned on and happy at the attention, indulgence, and – oh fuck it, pampering – of the two people he loved most in the world that he felt like he was going to explode. He shoved it all down and focused on Castiel’s face in front of him, with its expression of deep concentration, and on the feeling of the various brushes and stuff on his skin. Dean was on tenterhooks, wondering what he was going to look like.
After about five minutes, Sam joined them on the bench, sitting behind Dean and scooting close to him.
“You don’t want to watch?” Castiel asked, not pausing or taking his eyes from Dean’s face.
“Thought I did, but I decided I want to wait and see the final product,” Sam replied.
His warm hands landed on Dean’s hips. Dean closed his eyes and exhaled reflexively, relaxing a little again at his brother’s touch.
“Is this okay?” Sam murmured in his ear.
“Yeah,” Dean breathed. “‘S good, Sammy.”
Sam moved even closer. Dean could feel the hard line of Sam’s body against his. Sam’s thumbs on his hips made slow circles, and suddenly this contact was less soothing, though even more pleasant.
Sam started kissing his neck. Dean felt his cock twitch with interest, starting to fill. Dean realized that through his thin panties, Sam and Cas would be able to tell immediately. It made him harder and he squirmed with embarrassment and arousal.
Cas made a mildly irritated noise. “Sam, stop that. I need him to stay still.”
Sam shifted forward, peering over Dean’s shoulder and looking down. “Sorry,” he said, sounding amused. “I can see I’m not helping.”
Dean flushed again, but the embarrassment only made this hotter. Being exposed with Sam and Cas was simultaneously terrifying and safe as houses. Sam rested his hands flat on the outside of Dean’s thighs and kept them still; almost sexual, but not. Dean was grateful for the heat of Sam’s palms on his bare skin.
A little while later, Cas pulled back a few inches to examine Dean’s face critically.
“Is it okay?” Dean asked immediately.
“I’m not sure,” Cas said slowly. “I don’t think it looks like the videos.”
“Let me see,” Sam said, getting up. Dean missed the warmth and contact immediately.
Sam looked at him for a long moment. A slow smile spread across his face. He rested a hand on Castiel’s shoulder.
“I think you did a great job, Cas,” he said. He met Dean’s eyes. “Dean, you’re – gorgeous.”
“What? No way,” Dean said, automatic response kicking in again. “Lemme see.”
He stood up and walked a couple steps to the full-length mirror on the wall. For a moment he kept his eyes on the ground. Finally he took a breath and looked up to see…
Oh, shit. He was, actually, seriously pretty.
Cas hadn’t done anything too complicated, but Dean’s whole face looked softer. Cas had chosen a rose-pink lipstick that made Dean’s lips look even poutier than usual. A little eyeliner and green eye shadow made his eyes pop like whoa.
Dean stared openmouthed at his reflection. Sam came to stand next to him, grinning uncontrollably. Castiel joined them on Dean’s other side.
“Do you like it?” he asked uncertainly.
Dean swallowed hard. “Yeah,” he said. “Fuck – yeah, Cas, you did a hell of a job.”
Castiel looked gratified. “I’m glad you like it,” he said. “I think you look lovely, Dean.”
Sam’s arm snaked around Dean’s waist. Dean watched Sam in the mirror as he turned sideways and nosed into Dean’s hair.
“You like this, huh?” Sam said softly, breath on Dean’s ear. “You like us looking. Seeing you.”
Dean watched a flush spread across his chest as Sam brought his free hand to rest low on Dean’s stomach. His pinky finger just barely dipped under the waistband of Dean’s panties. Dean realized he was still half-hard and getting harder.
“Yeah,” was all he managed to say. Sam’s hand slipped down to cup Dean’s cock over his panties. Dean let out a small, involuntary noise.
Sam paused. “Is this okay? Do you want to stop?”
“Don’t stop,” Dean said fervently, pushing against Sam’s palm.
Sam chuckled and moved to stand behind Dean. He rubbed and squeezed Dean’s cock through the panties. The sensation made Dean feel crazy with need.
Finally, Sam slid his hand into Dean’s panties and started jerking him very slowly. Dean watched in fascination as a wet spot grew on the silky fabric where the head was pressed into it.
“Cas, you want to move his panties out of the way?” Sam asked casually, a few minutes later. Just the words “his panties” made Dean’s heart pound.
“Yes, although I was enjoying watching this,” Castiel replied. Identical grins split Dean and Sam’s faces. Dean grinned bigger at the sight.
His smile fell away as Castiel carefully pulled the panties down and Sam started stroking Dean in earnest; long, slow pulls that left Dean gasping. Castiel continued watching them. Dean’s gaze kept flitting from Cas’ rapt, joyful concentration, to Sam’s look of desire, then back to his own made-up face. His eyes looked freakin’ huge with the makeup.
“Would you mind if I finished him?” Castiel asked suddenly, very politely.
Sam dimpled. “Of course not,” he said.
He released Dean’s cock, making Dean whimper at the loss. His hips thrust forward a little, seeking more stimulation; he overbalanced in the unfamiliar heels and stumbled, but Sam was right there to catch him.
“I got you,” Sam murmured. Dean held on to Sam’s forearms and stared into the mirror as Castiel got on his knees. Cas eagerly licked a line up the underside of Dean’s shaft before taking his cock deep, making a pleased sound around it. Dean groaned helplessly. Castiel’s ability and pleasure in deep-throating had been a very unexpected but highly welcome reveal when they’d started dating him. Dean always wondered if it was a leftover angel power somehow.
And now it felt almost painfully good, especially when Sam slid a hand around to fondle and lightly squeeze his balls.
“Fuck,” Dean gasped, hips working even as he tried to hold back. This whole night had him so keyed up, he just knew he was about to embarrass himself. “I can’t last, fuck, you two’re – you’re – ”
“Dean, it’s your birthday,” Sam said low into his ear. “And you don’t need to impress anybody.” He nipped Dean’s earlobe. Castiel made an assenting noise that had Dean biting down on his rose-pink lips. “Come when you’re ready.”
“Fuck,” Dean repeated, because it seemed like the thing to say. He looked into the mirror at his own pretty face with its blown pupils, at his hands sliding into Castiel’s hair almost of their own volition, at Sam’s hungry look as he sucked a hickey into Dean’s neck. Dean couldn’t stop staring as he thrust faster and Castiel seemed to somehow, impossibly, increase his suction even more. Sam’s free hand slid up Dean’s corset to pinch his nipple and Dean couldn’t hold on anymore, making a guttural sound and gasping for breath as he came down Castiel’s throat.
And Dean still couldn’t stop staring into the mirror after he was finished. At the boots and the makeup, which Sam and Cas had given him. At his dress-up clothes, which Sam and Cas had accepted immediately and without question.
Dean felt so profoundly grateful for them that he was momentarily overcome. He just stared as Cas got to his feet and pressed a gentle kiss to Dean’s lips. Sam maneuvered so he could get one, too.
“Thank you,” Dean said finally, when he could speak again. “Th – thank you both.” The words were woefully inadequate to express what he was feeling, but from their expressions, he thought Sam and Cas probably got it.
Sam was still pressed against him and Dean realized suddenly that he could feel Sam’s erection against his ass.
“Oh fuck, sorry,” he said. “You two didn’t get to come or anything.”
Castiel frowned at him. “This is your birthday,” he reminded Dean. “Your pleasure was our paramount concern.”
“Yeah,” Sam agreed. “I don’t mind if you’re done for the night. I can get myself off, or me and Cas could have a quickie.” A grin flashed across his features. “Of course, if you’re interested, I have plenty of ideas for whenever you’re ready for round two.”
His eyes moved over Dean’s body again. Dean’s eyes widened.
He found that he was very interested, indeed. He leaned in towards Sam again and kissed him, long and deep this time. When he pulled away, they were both breathing hard.
“Let’s go to my room,” Dean said. He heaved in a breath and said the next words all in a rush, before he could change his mind. “I have some other outfits I want to show you guys.”
Pairing: Dean/Sam/Castiel
Rating: Explicit/NC-17
Genre: Slash
Word Count: 5700
Disclaimer: All for fun, none for profit.
Summary: Dean has a secret: he loves to dress up in women's clothes. When Sam catches him at it, Dean fears Sam and Castiel's reactions to this hidden part of himself.
Warnings/tags: Incest, crossdressing, polyamory, human Cas, shame, acceptance, fluff and smut, hand job, oral sex
A/N: Written for the
spn_reversebang. Thanks to the incredibly talented claraxbarton for providing the beautiful inspiration for this fic! Huge thanks as well to my beta, the amazing jj1564! Your comments and suggestions were invaluable.Art: Imgur
Read on AO3
***
Dean lay on the Impala’s hood, head resting on his clasped hands, elbows splayed out. He stared dreamily at the ceiling of the garage in the Men of Letters bunker, not really seeing it. He felt the cool of the Impala’s windshield beneath his shoulder blades, above his pink corset. Baby’s waxed hood was pleasantly smooth and a little slippery under his feet, which were encased in stockings. He didn’t think about anything, just enjoyed the sensations.
There was something about being dressed like this that always somehow both excited and relaxed Dean. It let him turn his brain off like few other things did. Before, he’d get shaky with anticipation; after, he’d have to deal with the shame. But when he was in women’s clothes, Dean just felt good. A little dirty, in a fun way. And, as much as he always tried to suppress the thought, whenever he was in a garter belt or panties or whatever, he felt…pretty.
He’d never told anyone about this; not even Sam and Cas, and they were his whole fucking world. He tried to justify it to himself; this was his secret, his thing. He was allowed to have his own thing.
Which would have been fine, except that a part of Dean actually really wanted them to see him like this. He wanted to see love on their faces and desire in their eyes at this part of him, too. But every time he thought about telling them, Dean felt sick. It wasn’t that he thought they were prejudiced; and, in theory, there was nothing wrong with a little cross-dressing – for other people.
But other people weren’t Dean. He’d spent his life building his image as a cool, tough guy. He imagined the shock and confusion he’d see on Sam and Cas’ faces if he ever told them. They wouldn’t understand. Hell, Dean didn’t even understand it. And what if they were mad that he’d never told them? Not only did he run the risk of fucking stuff up with them, he could lose the refuge that wearing these clothes provided for him.
No; Dean would never tell them. He stretched his arms out, popping his shoulders, and kicked his feet gently, contented. He rubbed a hand over his bare thigh, thinking about jerking off. It was always extra hot in girl clothes. Sam and Cas had gone out for dinner and wouldn’t be home for hours. He had plenty of time to –
“Dean?” Sam’s voice came from the corridor. Dean’s eyes widened in panic. He sat up and scrambled down the hood of the car, almost falling off in his haste to get up. He looked around desperately, but he had left his regular clothes in his room.
“Dean, are you in here?” Sam again, closer now – he was in the hallway outside the door to the garage. Dean opened the Impala’s door and got inside, slamming it shut behind him. He looked in the backseat for a blanket or something – anything – he could use to cover himself up, but there was nothing. He sank low in his seat and prayed Sam wouldn’t come over.
“There you are,” Sam said, entering the room. “Didn’t you hear me calling?”
“Sorry, I had music on till a second ago,” Dean said. “Look, I’m in the middle of something, so – ”
“Are you okay?” Sam said, voice concerned. “You sound weird.”
“I’m fine, man, just gimme a second – ”
But Sam was already at the window. “You’re just in the Impala,” he pointed out. “What’s – ”
He fell silent as he peered down at Dean. Dean swallowed and forced himself to look into his brother’s face. Sam was frowning in puzzlement and he looked slightly surprised, which was better than the abject horror that had long haunted Dean’s imagination.
Sam was silent for what felt like an eternity but was probably only a few seconds. “Okay, Dean,” he said finally, in a gentle tone. “Take all the time you need. The restaurant Cas and I were gonna eat at was closed, so we’ll be in the kitchen.”
He smiled softly at Dean and left the room.
Dean leaned forward and rested his head on the steering wheel, wondering how hard it would be to find and perform a memory spell that would wipe both him and Sam clean of the last two minutes of their lives.
***
Dean made himself wait five minutes before getting out of the car. He listened at the doorway for any sound of Sam or Cas nearby, then sprinted to his room and got changed as quickly as he could. He very seriously considered barricading himself in until the next morning. This was supposed to be Sam and Castiel’s date night, after all. But finally he decided that might make things feel even worse and weirder, so he forced himself to go to the kitchen, say hi, and grab some food before leaving them alone.
They both greeted him perfectly normally. Dean did his best to give the appearance that he was totally fine and not dying a thousand deaths inside. He thought Sam’s gaze lingered on him longer than usual but couldn’t be sure. Well, if that was the worst thing that happened because of this, Dean would consider himself damn lucky.
***
It was not the worst thing that happened. Dean had to spend the next two days avoiding Sam and Cas as much as humanly possible, because he simply did not know how to act around them anymore. Sam knew, and if Sam knew he must have told Cas. Dean felt like he had been flayed alive. This deep, shameful secret exposed to the light. It felt like when he’d told Sam about Hell; except that had actually been better in some ways, because he’d made a conscious choice to tell Sam about it. Yeah, “I like to wear ladies’ clothes sometimes” wasn’t exactly the same as “I spent a decade cutting people up,” but still. At least in Hell there had been circumstances. He’d come to like dressing up all on his own.
Finally, on the afternoon of the third day, Sam knocked on Dean’s bedroom door.
“Come in,” Dean called with forced casualness.
Sam opened the door and took a step inside. “Hey,” he said. “Tonight’s our date night. What do you want to do?”
Panic gripped Dean’s heart. “Oh, uh,” he said stupidly. “Listen, I’m actually not feeling so great.” He coughed dramatically. “I think I might be coming down with a cold. I don’t want you to catch it. You and Cas can take the shared room tonight if you want.” They each had their own rooms in the bunker, but there was also a bedroom they’d set up for all three of them, or when any two of them wanted some alone time.
Sam’s expression morphed into one of sadness. He took another step inside and closed the door behind him. Dean could feel his fear mounting.
“Dean,” Sam said, then hesitated. He looked like he was considering his words very carefully. “Listen, I don’t want to force you into anything you don’t want to talk about, or share. But I…I want us to be okay, too. You’ve seemed pretty upset these past few days.”
Fuck. Damn it. Why did Sam always know?
“And I want you to know,” Sam continued, “that I don’t think you have anything to be embarrassed about. Or ashamed of. Not that I’m saying you are – but if you were, you have no reason to be.”
Dean could feel his face going bright red as he stared at Sam, unable to speak. Sam glanced briefly into his eyes, then away.
“I just want you to be able to be around me,” Sam said, mouth turning down at the corners. “But if you need more time before you’re ready, that’s okay.” He turned to go, reaching for the door handle.
Dean simply could not stand for Sam to look that sad and for him to be the cause.
“What did Cas say?” were, bizarrely, the words that seemed to explode out of his mouth.
Sam turned back to him with a puzzled frown.
“When you told him about me,” Dean clarified. “What you saw.”
Sam’s frowned deepened. “I didn’t tell him,” he said, sounding surprised. “It’s your thing. It’s not my place to tell him.”
“Oh,” Dean said lamely, looking down at his bed. He couldn’t decide if this was good news or bad news. It had been horrible thinking everyone knew, but also, at least he didn’t have to have any awkward conversations.
Except that, obviously, he totally did.
“I – ” Sam hesitated again, then kept going. “I wouldn’t really know what to tell him, anyway. I mean, I know what I saw, but I don’t know what it means, for you.”
Dean leaned back against his headboard with a long-suffering sigh, scrubbing a hand across his face. “It doesn’t really mean anything.”
“No?” Sam was looking at him with that same careful, gentle expression. It was starting to annoy Dean.
“No,” he said. “And quit looming over me and looking at me like I’m going to break, would you? Sit down.”
A small smile flitted across Sam’s face. He took a seat at the edge of Dean’s bed.
“So, you’re ready to talk about it?” he asked.
“No,” Dean shot back. “I am absolutely, one hundred percent, not ready for this little chat. But it looks like it’s going to happen anyway.” He took a deep breath and tried to organize his thoughts. “Okay, so, when I was nineteen, right, this girl I was hooking up with got me to try on her panties. And I – I kinda liked it.”
Sam nodded, expression neutral.
“I wasn’t, you know, planning to make it a habit or anything. But I kept thinking about it, and finally, one day, I bought a pair of my own.” Dean tried to grin. “They were way too fucking small. Women’s sizes are super weird.”
Sam smiled.
“Awhile later I bought a bigger pair and managed to get the sizing right and I…put them on and…” Dean exhaled sharply. “I dunno, Sammy, I just liked how I felt. It felt…different.”
“More like yourself?” Sam suggested.
Dean shook his head. “No, look, I’m a guy, okay? It’s cool that some people with junk are ladies, but that’s not me.” He paused, frowning. “If anything, I guess I liked how I felt like a different person. It was kind of an escape, in a weird way.” He shrugged. “And from there it sort of spiraled. I mean, it’s not like I have a huge collection of stuff, not with the way we moved around.” He’d started to accrue a bit more now that they had the bunker to store it in, but Sam didn’t need to know that right now. “When I got time to myself, I just – dressed up.”
“And you never told anyone?”
Dean shuddered. “No fucking way. I mean, don’t you think it’s kind of ridiculous? Dean Winchester in a garter belt and shit?”
“No,” Sam said quietly. “I don’t think it’s ridiculous at all.” He paused, biting his lip. “I think you looked great,” he finished finally. “I mean, not that I got much of a look, but from what I could see…”
Dean could feel his face getting redder, if that was even possible.
“Yeah?” he managed to choke out.
“Yeah,” Sam said.
He met Dean’s gaze. Dean was thunderstruck to realize his brother’s pupils were slightly dilated.
“I’d love to see it again,” Sam said, words coming out in a rush. “Only if you want to let me, of course. If it’s your thing that you want to keep to yourself, I understand. But if you want to share it…” He exhaled in a shuddery breath. “I’m interested.”
For a moment Dean could only stare at Sam, excited and overwhelmed and completely not ready to seriously consider that at this moment. Finally he nodded a bit too quickly.
“Okay, man,” he said. “Cool, thanks, that – that means a lot.”
Sam nodded back and they fell briefly silent.
“Will you tell Cas?” Sam asked.
Dean groaned and rubbed his temples. “Yeah,” he said finally. “I’ll tell him. I don’t want to force you to keep a secret, and if you know, he might as well know.”
Sam smiled. “Okay,” he said, rising and extending his hand. “So, should we grab some dinner?”
Dean let Sam help him up. “Burgers. I deserve burgers after dealing with this conversation.”
Sam chuckled. “Anything you want.”
***
It took a day for Dean to psych himself up, but he finally managed to tell Cas his secret. Castiel listened attentively, head tilted slightly.
“All right,” he replied when Dean had finished.
Dean blinked. “‘All right?’ That’s all you have to say?”
“Dean, I am very used to you doing illegal activities.”
Dean spluttered. “What?! It’s not illegal!”
“Immoral?”
“No! I mean, some people think so, but some people are stupid.”
“Then why was it a secret?”
Dean shook his head, trying to figure out how to explain this. “It’s – it’s – it’s kind of weird, okay? Most guys don’t wanna wear women’s clothes!”
“Oh.” Castiel looked vaguely irritated. “This is a gender thing.”
“Yeah, it’s a gender thing.”
“I don’t understand gender.”
“Cas, you’ve been human for a couple years now. One of these days you’re gonna have to figure out gender.”
“Why?” Castiel sounded a little belligerent, but because of exasperation and confusion, Dean thought. He was tilting his head at Dean again.
“Because it’ll make things easier for you,” Dean replied.
Castiel frowned. “It doesn’t make any sense,” he said. “You say that most men do not wear women’s clothes, but in other societies and throughout human history, what men wore would look more like a skirt or dress to your eyes. The behaviors you associate with masculinity or femininity are constantly being performed by the one who is not ‘supposed’ to do it.” He raised his fingers in air quotes around ‘supposed.’ Dean rolled his eyes. “They also vary widely across history and cultures. I say that your narrow definitions of gender are foolish and illogical and serve no one.”
“Well, welcome to being human,” Dean snapped.
Castiel took a breath, his face softening. “What I am trying to say, Dean, is that I do not care what you wear.”
“Oh,” Dean said. He’d half-forgotten why they’d started this conversation. “Right. Thanks, Cas.”
Castiel touched Dean’s cheek and kissed him gently. “In fact, I would imagine that you look very aesthetically pleasing in those sorts of garments.”
He gave a sweet little smile as Dean blinked down at him, unable to think of a thing to say.
***
Dean’s birthday was a few weeks after these conversations had taken place. Sam and Cas hadn’t brought the subject up again, for which Dean was profoundly grateful. He was glad they knew, but he was still figuring out what – if anything – he wanted to do about the situation.
He hadn’t dressed up since he’d been caught. Partly because it felt weird, but mostly because he kept thinking about how Sam and Cas had seemed interested in seeing him that way. He wasn’t sure he could trust it. Not that he thought they were lying, but maybe they were only being polite.
Dean pushed these thoughts away as he enjoyed his birthday meal and pie. Sam disappeared after his slice, allegedly to get himself another cup of coffee. He came back with a large box instead.
Dean blinked at him. They’d only even started doing birthday meals a couple years ago. Presents hadn’t become a thing at all. Maybe something small and jokey. Not a large gift like this appeared to be.
Pushing away his confusion, Dean eagerly tore off the wrapping paper and opened the box. Inside were boots – shiny black vinyl knee-highs with big, chunky heels. Dean stared at them, his eyes going wide and his heartrate shooting up. They were beautiful, but he wasn’t sure whether to thank Sam or run for the hills.
Dean looked up at his brother; Sam looked eager, but guarded.
“It’s okay if you don’t like them,” he said immediately. “They’re returnable. I don’t know if they’re your style or anything you’re interested in, but I found this place online that sells this kind of shoe for bigger feet, and I thought…” He gestured randomly. “I thought maybe you’d like them.”
Dean swallowed around a sudden lump in his throat. “They’re great,” he managed to choke out. “Really, Sammy. Thank you.”
Dean glanced over at Cas, who was smiling. Dean realized he had pulled out a box from somewhere, too. Castiel pushed it across the table to Dean. It was much smaller than the shoebox, though hardly tiny.
“I got you something, too,” Castiel said.
Feeling a little nervous that there was a theme coming, Dean silently unwrapped and opened the box. Indeed, it was full of makeup. Dean stared at it.
“I can return this as well,” Castiel said, uncertainly.
“We weren’t sure if you were interested in makeup, either,” Sam said, sounding apologetic. “It’s really not a big deal if you’re not.”
Dean cleared his throat. “Uh, I mean, maybe,” he said. The truth was, he was very interested in makeup. But the one time years ago that he’d tried a little lipstick, the results had been so disastrous that he’d thrown it out and vowed never to go that route again. “I just – I don’t really know how to do that stuff.”
“Oh, that’s fine,” Castiel said, relief in his voice. “I can put it on you.”
Dean frowned at him. “Since when do you know how to use makeup?!”
“There are many tutorials on YouTube,” Castiel replied. “I have learned a lot. I believe I can make you look very glamorous.”
Dean couldn’t help but laugh at that, as much to release tension as in response to what Castiel had said. Sam and Cas smiled with him.
“Of course, you could play with the makeup on your own, too,” Sam hastened to add. “Whatever you want.” He paused for a long moment. “I don’t know if you decided you wanted to keep this private, or if you’re still thinking about it…” He trailed off, trying and failing to look casual. Dean could see the contained desire in Sam’s slightly too-wide eyes, in the bobbing of his Adam’s apple as Sam swallowed reflexively. It made Dean’s breath catch as he thought about it. Thought about showing off for them.
Dean looked to Cas, who was smiling fondly at him. Of course, Cas didn’t see anything unusual or taboo about this, so it probably wasn’t the same turn-on. But he’d sounded genuinely interested in the aesthetics when Dean had told him about it.
“Well,” Dean said in a thick voice. He rose suddenly, chair scraping out from under him. “I – I guess I’ll go try on the boots, then, and you guys can tell me how they look.” He half-fled to his room without a backward glance, heart hammering in excitement and fear.
***
Dean pulled out all his special clothes and laid them on the bed. He dithered over them for a full five minutes, even though he didn’t actually have that much stuff, before finally deciding to wear the pink corset, pink panties, and stockings with garters combo he’d had on the day Sam caught him. He’d been wondering ever since what Sam would think if he got a real look at Dean in that getup.
Well, now was his chance to find out. Hands shaking a little, Dean took off his regular clothes and got into the other ones. Last of all, he pulled on the boots. They fit like a dream.
Dean stood up slowly. He’d bought heels a few times, but never worked up the courage to try the shoes on in the store and so he kept getting bad fits. The one time he’d gotten close, he’d fallen over after a few steps and decided to give it up.
But Sammy’d taken care of him, somehow finding the perfect shoes for his feet. And the chunky wedge heel meant that walking wasn’t too difficult. Dean couldn’t help wondering if he could eventually learn to walk in sexy stilettos, but firmly pulled his thoughts back to the present. No good running before he knew he could walk in these way easier ones.
Dean took a few turns about the room, feeling pretty comfortable pretty fast. He turned towards the door and took a deep, steadying breath. He felt okay walking in them, anyway. Showing them off – all of this off – to Sam and Cas was a whole different manner.
“What the hell,” he muttered aloud, with more confidence than he felt. Trying to convince himself. “What are birthdays for, right?”
Dean opened the door and walked towards the map room. The hallway had never felt so long. Dean had never felt so exposed. It was terrifying, but it was exciting, too. He was way too nervous to get hard, but he could feel just the beginnings of arousal low in his pelvis.
“Okay,” Dean called, as he approached the entrance to the map room. “I’m coming in, so, uh, brace yourselves or whatever.”
Suddenly, deliriously, Dean decided he should just go for broke on this. He raised a hand above his head and rested on the doorframe, leaning into it, putting his other hand on his hip, elbow bent.
“What’s up, sailors?” he said, and then felt absolutely ridiculous. Was he out of his mind? Saying that? Dressed like this?
But it was too late. Cas and Sam were looking at him and they had most certainly heard him.
Castiel’s face broke out into a smile that made the corners of his eyes crinkle. “Dean,” he said happily. “You look beautiful.”
Dean could feel a flush creeping up his chest and neck at the unexpected word. “What? Shut up, no I don’t,” he said automatically, but the words lacked bite. Castiel just nodded as though Dean had agreed with him.
Dean’s blush deepened as he looked at Sam. Sam’s mouth had gone slack as he looked Dean up and down with an unmistakable expression of hunger.
“You look amazing,” he said finally, voice low. Dean gulped, the stirrings of arousal a little more insistent now.
“I see that the boots fit,” Castiel said, as if this was just a normal pair of shoes.
“Uh – yeah!” Dean said, looking down awkwardly at the gorgeous boots. He looked back up at Sam, giving him a lopsided grin. “Thanks, man. They’re great.”
“Would you like to try the makeup, as well?” Castiel said.
“Only if you want to,” Sam added hastily. Castiel gave him a look.
“Of course, only if he wants to. That’s why I asked if he’d like to.”
Sam’s dimples flashed. “There are nuances of politeness and obligation, Cas, since you gave him the makeup as a gift, and he’s tried on my gift. I can tell you more about it later. I just wanted him to know it was really okay if he didn’t want to do the makeup.”
“Oh. Thank you.” Cas turned back to Dean. “Yes, please do not feel obligated, Dean.”
Dean’s brain had stuttered at the thought of the makeup and was just now catching up with things again.
“Makeup,” he said dumbly. “Yeah. Fuck it. Let’s do this.”
***
The three of them moved to the large bunker bathroom. Castiel had Dean sit down sideways on a bench, straddling it. But before Cas could sit in front of Dean, Sam grabbed his arm.
“Hang on,” he said. “It’ll be easier if I shave him first.”
“I can shave myself,” Dean protested.
Sam raised his eyebrows at him. “Well, you can if you want,” he said. “But you usually use an electric razor, and it’ll be a closer shave if you let me do it with an actual blade.” He smiled softly. “And, it’s your birthday. I want to take care of you.”
Dean blinked and, after a second, nodded mutely. He watched Sam gather supplies: safety razor and shaving cream and a small basin which Sam filled with warm water. When he was ready, Sam stood before Dean, towering over him. Sam lathered Dean’s face and then went to work. He was careful and methodical. Dean found himself relaxing, lulled by the warmth of Sam’s hands and the gentle scraping sound of the razor on his skin in the otherwise silent room.
It seemed like no time at all before Sam was running his fingers gently over Dean’s cheek and chin to check for missed spots. Sam pronounced his work done and Castiel handed him a damp, hot towel. Sam scrubbed it gently over Dean’s face before patting his skin with a dry one.
“All the videos say moisturizing is important,” Castiel said, a trifle anxiously. Sam grinned.
“Dean has a bottle in the cabinet behind the mirror,” he said.
“Dude, shut up,” Dean muttered. Sam ignored him and took the bottle from Cas, applying the lotion over Dean’s face.
Finally, he stepped back. Castiel took a seat in front of Dean and got to work. Sam began prowling around, circling them slowly as he watched.
As the actual makeup application began, Dean’s relaxation from the shave faded. He was so freaked out and turned on and happy at the attention, indulgence, and – oh fuck it, pampering – of the two people he loved most in the world that he felt like he was going to explode. He shoved it all down and focused on Castiel’s face in front of him, with its expression of deep concentration, and on the feeling of the various brushes and stuff on his skin. Dean was on tenterhooks, wondering what he was going to look like.
After about five minutes, Sam joined them on the bench, sitting behind Dean and scooting close to him.
“You don’t want to watch?” Castiel asked, not pausing or taking his eyes from Dean’s face.
“Thought I did, but I decided I want to wait and see the final product,” Sam replied.
His warm hands landed on Dean’s hips. Dean closed his eyes and exhaled reflexively, relaxing a little again at his brother’s touch.
“Is this okay?” Sam murmured in his ear.
“Yeah,” Dean breathed. “‘S good, Sammy.”
Sam moved even closer. Dean could feel the hard line of Sam’s body against his. Sam’s thumbs on his hips made slow circles, and suddenly this contact was less soothing, though even more pleasant.
Sam started kissing his neck. Dean felt his cock twitch with interest, starting to fill. Dean realized that through his thin panties, Sam and Cas would be able to tell immediately. It made him harder and he squirmed with embarrassment and arousal.
Cas made a mildly irritated noise. “Sam, stop that. I need him to stay still.”
Sam shifted forward, peering over Dean’s shoulder and looking down. “Sorry,” he said, sounding amused. “I can see I’m not helping.”
Dean flushed again, but the embarrassment only made this hotter. Being exposed with Sam and Cas was simultaneously terrifying and safe as houses. Sam rested his hands flat on the outside of Dean’s thighs and kept them still; almost sexual, but not. Dean was grateful for the heat of Sam’s palms on his bare skin.
A little while later, Cas pulled back a few inches to examine Dean’s face critically.
“Is it okay?” Dean asked immediately.
“I’m not sure,” Cas said slowly. “I don’t think it looks like the videos.”
“Let me see,” Sam said, getting up. Dean missed the warmth and contact immediately.
Sam looked at him for a long moment. A slow smile spread across his face. He rested a hand on Castiel’s shoulder.
“I think you did a great job, Cas,” he said. He met Dean’s eyes. “Dean, you’re – gorgeous.”
“What? No way,” Dean said, automatic response kicking in again. “Lemme see.”
He stood up and walked a couple steps to the full-length mirror on the wall. For a moment he kept his eyes on the ground. Finally he took a breath and looked up to see…
Oh, shit. He was, actually, seriously pretty.
Cas hadn’t done anything too complicated, but Dean’s whole face looked softer. Cas had chosen a rose-pink lipstick that made Dean’s lips look even poutier than usual. A little eyeliner and green eye shadow made his eyes pop like whoa.
Dean stared openmouthed at his reflection. Sam came to stand next to him, grinning uncontrollably. Castiel joined them on Dean’s other side.
“Do you like it?” he asked uncertainly.
Dean swallowed hard. “Yeah,” he said. “Fuck – yeah, Cas, you did a hell of a job.”
Castiel looked gratified. “I’m glad you like it,” he said. “I think you look lovely, Dean.”
Sam’s arm snaked around Dean’s waist. Dean watched Sam in the mirror as he turned sideways and nosed into Dean’s hair.
“You like this, huh?” Sam said softly, breath on Dean’s ear. “You like us looking. Seeing you.”
Dean watched a flush spread across his chest as Sam brought his free hand to rest low on Dean’s stomach. His pinky finger just barely dipped under the waistband of Dean’s panties. Dean realized he was still half-hard and getting harder.
“Yeah,” was all he managed to say. Sam’s hand slipped down to cup Dean’s cock over his panties. Dean let out a small, involuntary noise.
Sam paused. “Is this okay? Do you want to stop?”
“Don’t stop,” Dean said fervently, pushing against Sam’s palm.
Sam chuckled and moved to stand behind Dean. He rubbed and squeezed Dean’s cock through the panties. The sensation made Dean feel crazy with need.
Finally, Sam slid his hand into Dean’s panties and started jerking him very slowly. Dean watched in fascination as a wet spot grew on the silky fabric where the head was pressed into it.
“Cas, you want to move his panties out of the way?” Sam asked casually, a few minutes later. Just the words “his panties” made Dean’s heart pound.
“Yes, although I was enjoying watching this,” Castiel replied. Identical grins split Dean and Sam’s faces. Dean grinned bigger at the sight.
His smile fell away as Castiel carefully pulled the panties down and Sam started stroking Dean in earnest; long, slow pulls that left Dean gasping. Castiel continued watching them. Dean’s gaze kept flitting from Cas’ rapt, joyful concentration, to Sam’s look of desire, then back to his own made-up face. His eyes looked freakin’ huge with the makeup.
“Would you mind if I finished him?” Castiel asked suddenly, very politely.
Sam dimpled. “Of course not,” he said.
He released Dean’s cock, making Dean whimper at the loss. His hips thrust forward a little, seeking more stimulation; he overbalanced in the unfamiliar heels and stumbled, but Sam was right there to catch him.
“I got you,” Sam murmured. Dean held on to Sam’s forearms and stared into the mirror as Castiel got on his knees. Cas eagerly licked a line up the underside of Dean’s shaft before taking his cock deep, making a pleased sound around it. Dean groaned helplessly. Castiel’s ability and pleasure in deep-throating had been a very unexpected but highly welcome reveal when they’d started dating him. Dean always wondered if it was a leftover angel power somehow.
And now it felt almost painfully good, especially when Sam slid a hand around to fondle and lightly squeeze his balls.
“Fuck,” Dean gasped, hips working even as he tried to hold back. This whole night had him so keyed up, he just knew he was about to embarrass himself. “I can’t last, fuck, you two’re – you’re – ”
“Dean, it’s your birthday,” Sam said low into his ear. “And you don’t need to impress anybody.” He nipped Dean’s earlobe. Castiel made an assenting noise that had Dean biting down on his rose-pink lips. “Come when you’re ready.”
“Fuck,” Dean repeated, because it seemed like the thing to say. He looked into the mirror at his own pretty face with its blown pupils, at his hands sliding into Castiel’s hair almost of their own volition, at Sam’s hungry look as he sucked a hickey into Dean’s neck. Dean couldn’t stop staring as he thrust faster and Castiel seemed to somehow, impossibly, increase his suction even more. Sam’s free hand slid up Dean’s corset to pinch his nipple and Dean couldn’t hold on anymore, making a guttural sound and gasping for breath as he came down Castiel’s throat.
And Dean still couldn’t stop staring into the mirror after he was finished. At the boots and the makeup, which Sam and Cas had given him. At his dress-up clothes, which Sam and Cas had accepted immediately and without question.
Dean felt so profoundly grateful for them that he was momentarily overcome. He just stared as Cas got to his feet and pressed a gentle kiss to Dean’s lips. Sam maneuvered so he could get one, too.
“Thank you,” Dean said finally, when he could speak again. “Th – thank you both.” The words were woefully inadequate to express what he was feeling, but from their expressions, he thought Sam and Cas probably got it.
Sam was still pressed against him and Dean realized suddenly that he could feel Sam’s erection against his ass.
“Oh fuck, sorry,” he said. “You two didn’t get to come or anything.”
Castiel frowned at him. “This is your birthday,” he reminded Dean. “Your pleasure was our paramount concern.”
“Yeah,” Sam agreed. “I don’t mind if you’re done for the night. I can get myself off, or me and Cas could have a quickie.” A grin flashed across his features. “Of course, if you’re interested, I have plenty of ideas for whenever you’re ready for round two.”
His eyes moved over Dean’s body again. Dean’s eyes widened.
He found that he was very interested, indeed. He leaned in towards Sam again and kissed him, long and deep this time. When he pulled away, they were both breathing hard.
“Let’s go to my room,” Dean said. He heaved in a breath and said the next words all in a rush, before he could change his mind. “I have some other outfits I want to show you guys.”
