Pretty In Pink (Isn't He?)

Chapter 1

"There you go. Spread your legs for me."

Sam blushed furiously.

"Sam."

"Ok. Ok…" and Sam eased his thighs open, revealing the pink satin panties Dean gave him earlier that day.

"See? What I tell you? Feels nice, huh."

"Yeah." Dean rubbed his fingers over Sam's cock through the satin. Sam moaned, and a dark flush of precum leaked through the fabric. Dean tongued it, and Sam's hips bucked upward.

"Gonna take care of you. Don't you worry." Dean slipped the panties to the side, exposing Sam's neatly shaven balls, drawing one into his mouth, then the other, holding Sam's thighs wide open with the palms of his hands.

"Fuck. Oh god. Oh god."

"Yeah, Sammy, you like that?

"Please…just, please."

"Please what?"

"Don't make me say it."

"Love to hear you say it. Not gonna if you don't say it. You know the rules."

Sam squirmed.

"…lick me."

Dean grinned up at Sam, green eyes glinting mischievously.

"Lick what, exactly? Want me to lick your cock through your pretty pink panties?"

Sam groaned, but that's not what he wanted.

"No. Want you to…"

"Come on, baby. Tell me what you need."

"To lick my…ass."

Dean dug his teeth into Sam's inner thigh.

"Uh-uh. That's not what we're calling it tonight, is it?"

"Dean."

"You want it, you gotta ask for it right. I'll do it. You know I want to. Can't wait. But I gotta hear you ask me right."

Sam blushed so hard, his face and chest turned bright red. He turned his head away, and whispered into the pillow, "Lick my pussy."

"Can't hear you, Sam."

"Fuck you."

"Not until you say it."

Dean placed one finger against Sam's jaw and with the lightest of pressure, tipped Sam's face back.

"Look at me."

Sam eyes fluttered, locked onto Dean's chest, then raised to meet his gaze.

"Give you everything you want. You just gotta say the words."

Sam swallowed hard. "Lick my pussy."

Dean groaned. "There you go. That's what I wanted to hear." Dean tugged the panties to the side, moved his tongue lower, ignoring his cock completely, pressing it lightly against Sam's perineum.

"Want me to eat you out like a girl, Sammy?"

Sam dug his fingers into the sheets and arched his back. "Please. Please."

Dean pulled Sam's legs closer, tugged the panties halfway down Sam's thighs, then pushed his legs back, pink satin stretched between them, Sam's ass exposed and accessible. He teased the tip of his tongue around the rim. "Say it again. So pretty when you say it."

Sam chewed his lower lip and looked Dean in the eye, his big brown eyes already gone dark from the pleasure high. "Lick my pussy. Please."

Dean plunged his face between Sam's thighs, eating him out like a starving man at a buffet. "Taste so good, Sam. Feel so fucking good." He swirled his tongue in circles, darted in to penetrate the first ring, curling up at the tip, making Sam gasp, then licked long and slow from the back all the way up to the base of his cock, pressing his thumb against the perineum the way that felt so good. He licked Sam good and messy, with lots of saliva to keep it slick. "Yeah, Sammy. All nice and wet. So good. Could do this for fucking days."

Sam tugged at the panties restricting his legs. "Off. Please. Off." Dean pulled them free and set them at his side, in arm's reach. Sam was then able to spread his legs wide, heels on the bed, and fuck up into Dean's tongue, gyrating against his face, hands holding the back of Dean's head.

"Tell me how much you love it or I'll stop."

Sam sobbed. "Please. Don't stop. Your tongue feels so good in my pussy. Love it when you eat me out. So wet for you."

Sam's cock was dripping with precum, all over his stomach. Sam pulled Dean's hand up so he could touch it.

"Fuck. Sam. Soaking wet." Dean brought his fingers to his mouth and sucked. Sam let out a helpless groan and grabbed the backs of his knees, spreading himself wide open.

"Don't stop, Dean. Fuck my wet little pussy with your tongue."

Dean held Sam's ass with both hands and rocked him up and down against his mouth, making him fuck himself against Dean's tongue. Sam cried out again and again, delirious with pleasure. Dean stabbed his tongue as deep inside Sam as he could, twisting it, opening him up.

"Dean. Dean. Gonna make me come."

Dean pressed his lips tight against Sam's ass and sucked rhythmically. Sam started to shudder. "Fuck. Fuck. Fuck. Wanna come for you. Please. Dean. Let me come. Please."

"How do you want to come, Sammy?" Dean liked making Sammy talk dirty, liked making him say it. "With my tongue in your hot little asspussy? Or on my cock?"

"Your tongue. Please. Make me come with your tongue. God. Gonna come so fucking hard for you."

Dean flicked his tongue around and inside Sam's ass, scraping his tongue against him roughly, driving him hard now, listening to his gasps and cries. "Come on, Sammy. Come for me." He grabbed the pink panties at his side and wrapped them around the head of Sam's cock, sliding the slick fabric up and down lightly, just giving him a bit more sensation to tip him over the edge, driving his tongue as hard and deep inside Sam as he could.

Sam threw his head back and howled, shooting so hard that come spattered his chest and face, spasming beneath Dean.

Dean slid up and slid his cock inside Sam in one hard thrust. "Christ, Sam, look how sweet you took that." Sam's body didn't resist whatsoever, just drew Dean in deep, closing tight around him. "So fucking tight." Dean went deep and rolled his hips in a slow, grinding circle. Sam brought his legs all the way back and grabbed his ankles, tipping his ass up so Dean could take him as deep as he wanted. Dean drew back and plunged in to the base, and again, and harder. "Fuck, Sammy, Sam…" and with that, Dean was coming, his whole body convulsing uncontrollably, making rough, guttural cries.

After a moment, Dean pulled free and collapsed at Sam's side. When he'd recovered somewhat he brushed his lips against Sam's neck. "Was that good, Sammy? What you wanted?"

Sam buried his face in Dean's chest. "Yeah. God. So good."

"Fucking awesome, is what it was."

Sam smiled.

Dean pulled Sam closer. "Oh, and next time, Sammy? Next time you're wearing the skirt too."

Chapter 2

Sam was acting weird.

Ok, Sam usually acted weird, but this was different.

First off, he wouldn't let Dean shower with him. "Sometimes—just sometimes Dean?—a person needs a little privacy. Just to remember what it's like, ok?"

And he put on his clean clothes in the bathroom with the door shut.

And he turned down a perfectly good blow job when he came out.

"Dude. Something we gotta talk about?" Dean poured Sam a tiny cup of motel coffeemaker coffee, from the tiny motel coffeemaker. The cup looked like part of a doll set in Sam's massive hand.

"Nope. We're good." Sam's face was flushed, but his eyes met Dean's gaze without squirming away (Sam's tell for when he was upset about something).

Dean ran his hand along Sam's back and settled on the curve of his ass. "You'd tell me. If I pissed you off?"

Sam drank half the coffee in one gulp and grimaced. "Oh. You'd know. But you haven't. Promise."

Dean was usually the one who resisted cuddling and kisses and all of that bullshit, but when his insecurities flared—like now—he either got VERY demonstrative or he turned into a prick. Sam was very clear that he much preferred the first, so that's how he ran with it.

Dean nuzzled at Sam's chin like a dog trying to get some attention, and when Sam turned his face towards him, mouth twitching in a smile, Dean gently worried Sam's lower lip between his teeth, and then kissed him. A real Dean Winchester, "make 'em weak in the knees", phasers set to On Your Back Now kiss. With the little lip bite first looking at Sam's mouth, then getting lost in Sam's eyes, letting his lips touch Sam's oh so gently, the slow, sweet sweep of his tongue across the seam of Sam's mouth until Sam parted his lips for Dean, let him in, the hand at the back of the neck, the other hand on his face, thumb caressing his jawline, then pulling Sam's mouth open wider so Dean could slowly ease his tongue past Sam's teeth and possess his mouth…

He had Sam sucking on his tongue and moaning into his mouth in less than a minute.

"Ok. Ok. " Sam unzipped Dean's fly and sank to his knees. He took a swig of coffee in his mouth, held it there for a moment, then swallowed and sucked Dean's testicles into his mouth, one by one.

Dean gripped the edge of the table with both hands and swore, shuddering. Sam's mouth was wet and HOT and mother of all that's holy it felt good. "Fuck."

Sam sucked and lapped at Dean's balls, tugging on them with his lips gently, while Dean twitched.

Another mouthful of coffee, swirled in his mouth, and swallowed, and Sam sealed his mouth around the crown of Dean's cock and sucked the length of it into his mouth, slowly, inch by inch. Dean's bowlegs were wobbling by the time the tight seal of Sam's lips brushed against his balls, his big brown eyes staring up into his face, blown wide with admiration and lust and so much love it hurt to look at.

The molten, wet heat of Sam's mouth was too much, and Dean was spilling into Sam's mouth within what felt like seconds. Sam swallowed, and swallowed, and swallowed. Never let a drop spill.

Sam sat back on his heels, grinning. "Feel better?"

Dean tucked himself back in his jeans. "You have no idea."

Sam got to his feet, finished the last of his coffee, and made a face. "That shit tastes nasty."

"Most people say that about come."

"Most people haven't tasted yours."

Dean's face crinkled with a smile better suited to learning he'd won the lottery, not had his little brother tell him how good his ejaculate tasted. But everybody has their own definition of awesome things to hear. "Christ I love you."

"Are those tears in your eyes?"

"Shut up."

"Are they?" Sam gripped Dean's face

"You're so annoying." Dean swatted Sam's hand away.

"Gee, your come tastes terrific!"

"Seriously, Sam. Gonna kick your ass."

"You can try. Oh, and wrong verb." Sam grabbed his jacket. "Gotta get to the library. I'll call you when I got what we need." One last slow kiss, and Sam was out the door.

Dean didn't get it what "wrong verb" meant until Sam was across the parking lot.

It took him an hour to come down from his high and realize that Sam hadn't gotten off.

Hadn't even tried.

Chapter 3

It took every ounce of Sam's self-control to stop himself from stripping his clothes off and begging Dean to take him hard. But he couldn't. He had to keep the surprise he had planned meticulously for that evening.

And the first part of the plan involved shaving his legs smooth.

He'd showered by himself (after he pushed Dean under the steamy spray and told him to enjoy the moment alone), where he carefully soaped up and gone through two razors gingerly shaving his armpits and his legs baby smooth, making sure to rinse all the hair down the drain. The water was cold by the time he was done, but he hadn't nicked himself except on the hard round bone on his ankle.

He changed into his clean clothes behind the locked door as well.

When he came out, he could tell Dean was worried, amping himself up, fearful that Sam was losing interest, had seen someone hotter, younger, different. Everybody has at least one wound that won't heal, and Dean's was that he felt he wasn't good enough. For anything.

Sam reassured him, but knew that words weren't going to be good enough. Dean needed to see and feel Sam's love in the flesh, in practice, in concrete action, not abstract thought.

But when Dean slipped next to Sam and cupped the front of his jeans, murmuring an offer to take care of his little brother, Sam had no choice but to grit his teeth and deflect.

If Dean so much as tugged Sam's jeans partway down, he would see Sam's sleek, hairless thighs, and there'd be no graceful way to explain it without spoiling all of Sam's plans.

But that kiss. Christ, that kiss. Nobody kissed like Dean Winchester. Nobody in the history of anybody. Sure, Dean was a natural hunter, and was trained to frightening efficiency in hand-to-hand combat. He could track a falcon on a cloudy day. He could outshoot, outdrink and outfight anybody. But the thing Dean did best of all was kiss.

Dean could—and did—make Sam come just from kissing. Not kissing plus dry-humping, kissing plus dirty talking, or kissing plus touching him. Just kissing, only their upper bodies touching, breaking contact to look into his eyes, touch his face, then that mouth (that mouth that cocksucking mouth) pressed onto his, exactly the right warmth, firmness, softness, the way he slipped his tongue across Sam's teeth, along the underside of his lips where the skin is the softest anywhere on the human body, licking up inside, teasing the roof of his mouth—and since when was that hot? But it was. Christ, was it ever.

So when Dean moved in for the kill (and Sam saw it in his eyes, saw what Dean was about to do, and knew he was fucked, was going to be fucked, and the secret would be ruined), Sam, in a word, despaired.

But somehow, he pulled out a save at the last minute. The coffee gave him the idea. The only flavor it possessed was bitterness. Its only saving grace was that it was hot.

So when Dean had rendered Sam practically incoherent with desire after less than a minute, Sam tried one last desperate measure: the hot liquid blowjob.

The only thing better than a blowjob from a mouth warmed by a hot beverage is one where the person doing the sucking alternates between sips of hot and ice-cold liquid. Sam made a note to drive Dean out of his fucking mind with that scenario another time.

But for the time being, he thought he could distract Dean with the hot part long enough to get out the door and get on with the rest of his preparations, which were extensive and would take him all day.

Sure enough, Dean fell to pieces, practically convulsing with pleasure at how Sam's normally unforgettable technique was taken over the top by how warm his mouth and tongue were. A couple of minutes and Dean was coming in Sam's mouth. And Sam loved it. Loved how Dean tasted. Other men Sam had sucked off tasted sharply bitter, deeply unpleasant, concentrated and mineral, like a decaying oyster. Dean tasted earthy, salty, but with a sweet, whiskey-tinged note. Sam loved it. Didn't dare tell Dean, because if he knew how much of a trembling and frantic thing Sam had for Dean's come there's no telling how much teasing he'd give him for it, but he would have gladly sucked his brother's cock every single morning for the rest of his life, swallowed every drop, and thanked god for it.

Apparently, Sam was as gifted at oral sex as Dean was at kissing, because he left Dean twitching and orgasm-stoned, and was able to make his escape without being found out.

Sam walked the three blocks to the library and went inside, just in case Dean was watching. After 15 minutes, he slipped out the back exit and made his way to the beauty salon.

He'd met Vicki running down some leads on a murdered drag queen that Sam and Dean had identified as the latest victim of a ghoul's nest. She was sweet and funny and a transwoman. It was clear she had an immediate crush on Sam, but she knew from the first second Sam and Dean walked in what existed between them.

Dean had left Sam to finish up the interview so he could return Bobby's phone call. After Sam had gotten the information he needed, Vicki tucked a lock of her blonde wig behind her ear and said to him, "You know, you've got gorgeous bone structure. You'd look so beautiful in drag." The series of expressions that flitted over Sam's face—shock, disbelief, a pure burst of pride, a heartbreaking flash of something hopeful and scared—told her everything he couldn't say.

And the hook was set.

When Dean was taking a nap in the afternoon, Sam snuck outside and called her. "Hey, what you said earlier? Could you…I… I'd like to…"

"Can I do you up? Sweetie, I'll do you male-to-female head to toe."

They talked for an hour. Sam spilled his guts to her about Dean (leaving out how they were brothers—and hunters), what they had been experimenting with, how it made Sam feel, how he wanted to go all the way with it and surprise Dean. They arranged for the plan to go down on Friday. Vicki gave Sam instructions on what to do over the two days before coming to see her as early on Friday as he could break free. Sam dutifully exfoliated his whole body as directed, and showered that morning with an antibacterial scrub.

When Sam walked inside the empty salon, Vicki flipped the Open sign to Closed and locked the door.

"Don't be scared. It's going to be fine."

Sam slumped on a swivel chair. "I'm freaking the fuck out."

"Don't even start."

"What if he—"

"He loves you. LOVES you. That comes off him in waves. Anybody can see it. Everybody."

"This… this is scary."

"He's the one that gave you the panties and high heels, Sam. He's the one that said next time, you're wearing the skirt too. He wants this as bad as you do, sweetie."

Sam pushed his hair out of his eyes. "Gonna look ridiculous. Tall as I am. Jesus, in heels I'm gonna be like 6'7." Sam stared at his hands.

Vicki took his hands in hers. "Sam. You're going to look like a goddamn Amazon princess. You'll be stunning. Trust me. I'm the best."

She led Sam over to a room in the back. "First things first, we're going to get started on the waxing."

Vicki donned a set of purple gloves. When Sam took off his shirt, she erupted in a fit of coughing. "Goddamn."

Sam grinned. It had been a long time since he'd been shirtless in anyone's company other than Dean, and he did like the attention. He lay back on the sheet-draped massage table and rubbed his stomach.

"Flirt."

"Yes, ma'am."

Vicki smoothed baby powder all over his chest and dusted him off. Next, she smeared warm wax on a small section of his chest with a wooden stick. She covered it with a strip of white muslin and pressed her fingers over it firmly several times to make it stick. "I'm just going to pull gently forward." She pulled the fabric off quickly, immediately pressing her gloved hand on the hairless patch to soothe the sting.

Sam registered no pain. Vicki's eyebrows shot up. "Well, ok then." She proceeded to wax his chest smooth. The only time Sam flinched was when she waxed the area around his nipples.

She made him take a break and drink some tea, and pick out some new CDs. Sam selected Pearl Jam and Jeff Buckley.

Vicki waxed Sam's hands, the backs of his knuckles, his arms, and the treasure trail down his stomach, dusting each section with baby powder beforehand and slathering it with baby oil afterwards.

"You don't really have any hair on your back. We could skip it if you want."

Sam said, "I want to do it right."

When she had finished waxing his back, he sat up, smoothing his fingers over his body. "This is so weird."

"You're deflecting. You know what comes next."

Sam's face reddened.

"You said you want to do it right, right?" Vicki stirred a pot of dark red wax. "You want to make that pretty little boyfriend of yours, what were your exact words, lose his fucking mind?"

Sam bit his lip. "Yeah."

"Well, sweet cheeks, there's no way around it. We're simply going to have to wax that sack and crack."

Chapter 4

Sam pressed his face down into the cool cotton sheet covering the waxing table, and tried to pretend he was somewhere else. Anywhere else than buck naked in a salon about to get a sack-and-crack wax.

"Ok, I'm going to get started now. Are you ready?"

Sam thought back to all the foes he and Dean had fought, for the world, for each other. Vampires, rugarus, ghosts, demons, the devil himself. But the scariest thing he had ever faced was a transwoman named Vicki with a jar of ass wax.

"Yep." Sam sold the false confidence like nobody else. But Vicki was no fool.

She knelt alongside him, and took his hand. "Hey. It's normal to be a little nervous. But I swear, it sounds way worse than it is. Trust me. I have it done all the time."

Sam looked hopeful. "Yeah?"

"Yeah. Doing the hair around the nipples hurts worse."

Sam chewed on his lower lip. "Not the pain I'm worried about."

Vicki held his hand a little tighter. "It's a really intimate thing. I know."

Sam gave a shy little smile.

"I'm like you, you know." Vicki stood up and moved behind the table. "Total exhibitionist sometimes… but I'm also really shy."

Sam pushed himself up on his elbows and craned his neck to look behind him. "You really think I'm an exhibitionist?"

Vicki smacked Sam's bare ass. "Sweet cheeks, don't even try."

Sam lay back down. "Ok, here we go." When Vicki said, "Could you take your right hand and pull your butt cheeks apart for me?" Sam curled his head down and buried it in the sheet. "Oh god."

"Remember what you're doing this for."

Sam closed his eyes and thought of Dean.

He shivered as she laid a stripe of warm wax down the center. He gritted his teeth as she smoothed the cloth strip over it and yanked hard and…

"Huh."

"Told you. Sounds a lot worse than it is."

The searing pain he expected (and as a testimony to how much he loved Dean, the searing pain he fully expected to have to endure for this whole plan) simply didn't materialize. Sure, it was uncomfortable. Nobody would ever say that having the hair around one's anus waxed was delightful. But it wasn't that bad.

A few more strips and that area was clear. "Alright, Sam, I need you to turn over on your back. Ok, now bend your knees and hold your legs open for me." Sam turned bright red, on his back, hands on his thighs holding his legs open like he'd only ever done for Dean, so flush with desire for him that all inhibitions melted away. Not in a brightly lit beauty salon in the middle of a day with a sweet but unfamiliar person wielding a narrow wooden spatula dripping with wax.

"This part is going to be a little more intense." She smoothed the warm wax over Sam's perineum, and oh, what Sam feared would happen, did.

He should have expected it, really. He was an exhibitionist, in the right circumstances. He did love to be on display, to be desired and appreciated. And although Vicki was a consummate professional, it was clear to both of them that she was attracted to Sam. So there he was, spreading his legs for her so she could get to his taint and ball sack easily, completely exposed, and then the surprisingly erotic feeling of the warm, wet wax on that sensitive patch of flesh… his cock thickened immediately. Completely. Gloriously.

Vicki cleared her throat. "That's absolutely normal. A totally normal physiological reaction. In fact, if it didn't happen, you should worry."

Vicki smoothed the fabric strip along his skin. Her fingers trembled.

That made him even harder.

She tugged sharply, and ripped the cloth away, immediately smoothing her gloved hand over the skin to soothe the sting.

Sam cried out. But it didn't sound like a cry of pain. Because it wasn't. Not exactly.

They looked at each other for a moment without saying anything.

"Keep going." Sam got a tighter grip on the backs of his knees.

Vicki swallowed hard, and proceeded. A few more swathes of wax, and the perineum was clean. Each tug of the cloth made Sam's cock twitch and bob, pulling a grunt or choked cry out of Sam.

Sam thought he heard Vicki murmur, "Jesus Christ" under her breath.

"Keep going," Sam directed.

The first touch of the warm wax on his scrotum, and a clear drop of pre-cum welled up in the slit of Sam's cock. "Oh god." Sam didn't even know what to do with himself.

Thank god for Vicki.

"You must really love that man of yours. Doing all this for him."

"I do. I really fucking do," Sam choked out.

"You like doing things to please him, huh."

"You could say that."

"He's your Dom?"

Sam thought about it. "He's my everything."

Vicki pressed her gloved fingers against Sam's sack, holding the skin taut, and pulled the first strip off.

"Fuck!" Sam cried out, back arching involuntarily, his cock twitching violently, then hitting his belly with an audible slap.

"Does that… hurt too much?"

"No, it's not that. It's…" and Sam was unable to finish the sentence. His cock lay aching and desperate on his belly, and each jolt of pain, while Sam lay there spread open and watched, only made it worse.

"I bet your man would love to be here right now, watching me do this to you. For him."

Sam blinked at her, awash in gratitude. He couldn't believe it. She'd found a way out for him, a way to navigate this impossibly complex situation there on top of the waxing table, without compromising her integrity or breaking the solemn vow he and Dean had made to each other: only you. Only love each other, only sleep with each other, only come for each other.

"Yeah. He'd love it."

Vicki smeared more wax. "What would he tell you to do, Sam? If he were here watching you?"

Sam bit his lower lip. "Tell me to touch myself."

"Yeah?" Her voice shook almost imperceptibly. "I suppose you better, then."

She extended a container of lotion toward Sam, only meeting his gaze for a split second. Somehow, Sam felt like she didn't want to intrude on a moment between him and Dean. And Dean wasn't even there.

Sam pumped a squirt of lotion into his hand, and slicked his cock with it. He could not stop himself from moaning.

Vicki stretched the skin on his scrotum again and again, stroking warm wax on him, moving the applicator more slowly than before, pulling on the fabric strips with sharp jerks, and Sam worked his cock, gasping with the pain/pleasure of it.

"You're doing so well, Sam. Dean would be proud of you. Taking all this for him."

Sam increased his pace, punishing his cock, stripping it hard and fast.

"Do anything for him. Anything."

"I can tell, baby. Look how good you are for him." Her voice was lower now, more in keeping with the gender she was erroneously born with. "Are you going to come for him?"

Another tug of the cloth. Another spike of pain rushing through Sam, legs splayed open wide. For Dean. Balls waxed baby-smooth. For Dean. Fisting his cock. For Dean.

"Fuck. Yes. Yes." And as Sam's orgasm surged through him, witnessed by an open-mouthed Vicki, he chanted one word. The only word he ever said when he came. "Dean. Dean. Dean."