Pretty in Pink (Isn't He?) Chapter 5: Tuck and Cover

[justinedelarge]

Author: justinedelarge
Fandom: Supernatural
Pairing: Sam/Dean
Rating: R
Words: 2100
Warnings: Wincest, crossdressing
Disclaimer: I don't own what I don't own.
Summary: Sam completes his male-to-female makeover to surprise Dean. 

 Chapter 5: Tuck and Cover 

Vicki handed Sam a box of tissues. He took it without looking at her, and wiped his chest clean from the evidence of his orgasm.

“We promised each other it wouldn’t get weird.”

Sam glanced up quickly, and Vicki cocked an eyebrow at him.

Sam’s face creased into a huge grin. “You just quoted Austin Powers at me.”

“I did.” To Sam’s intense relief, Vicki did not look upset or creeped out in the slightest. Her cheeks were flushed pink, but her eyes, a striking blue, met his without a second of hesitation.

“Get dressed.” Sam slipped off the table and pulled his boxers on.

She paused, as if thinking hard about what she was going to say, and then spoke. “Thank you. For trusting me that much to let me share in such a private thing.” She stopped for a moment, considering her words carefully. “Very few people on the planet are as beautiful as you are. You’re breathtaking. And I say that as a clinical fact. My friends and I, we used to joke that there should be a federal mandate that people that beautiful could not be monogamous. By law.”

Sam erupted in a deep, hearty laugh, fastening the button of his jeans, face coloring from the praise. Which he drank up like a thirsty plant under a sudden rainstorm in summer.

“But very few people are as in love as you are with this man of yours. He’s lucky six ways from Sunday. And I get the feeling he’s been with you for a long, long time. Yeah?” She scrutinized his face closely.

He simply nodded. No way could he tell her everything, although he felt such a strong pull to do exactly that. Confess the whole thing to another human being. No, he corrected himself, to her. Just to this one, singular human being.

“So, not many people have ever seen what you just showed me.”

Sam blushed. “Yeah. That’d be a big no.”

“That was...” Vicki’s breezy confidence wavered. She shifted in place, busying herself at the side table, showing only her profile. “Ok, so that was the most beautiful thing I’ve ever seen.”

Sam’s hands, gripping his t-shirt, paused in mid-air.

“Sam. Do you even have a fucking clue? About how… I mean, it’s not just how you look. Although, holy fucking shitballs. But it’s more than that. You’re so… honest about your sexuality. Especially when you give yourself permission to let someone see you. And that was what was so beautiful.”

Vicki turned to face him.  “And that’s the only reason I’m being crass enough to talk about our little moment there. I was worried you were going to turn in on yourself, shut it down, feel embarrassed or ashamed.” Her mouth tightened. “Don’t do that to yourself. There’s enough bastards out there trying to make us feel that way about who we are. Who we love. They call us freaks.”

Sam’s hands clenched. That word had extra-sharp teeth to him.

“You know what I say to that? What I actually say to them?” Vicki tossed her head, flipping her platinum blonde hair over her shoulder. “‘You say freak like it’s a bad thing.’ I mean, so what? Being a freak is good. It’s normal. There’s a whole beautiful continuum of sexuality and gender. We’re just a little farther from center.” She blinked her eyes quickly a few times. “So fuck ‘em if they call us freak. We’re taking it back. Just like fag and queer.” Vicki was exceptionally good at hiding her true emotions. But Sam was exceptionally good at spotting what people felt but tried to hide.  

Sam put his hand on her shoulder. She smiled almost gratefully. “I’m not stupid. There’s a time and a place. But when the time is right and the place is safe? Let your freak flag fly.”

~

Vicki brought Sam into her small apartment above the salon, and made a light lunch of chicken salad wraps and green tea.

“So. Hair. What do you want to be? Blonde? Redhead?”

Sam blinked a few times in rapid succession. “I have no idea.”

“Eat up then, and we’ll try some on you.”

They ate quickly, and proceeded to the next stage. Wigs.

The pixie-cut white-blonde wig drew fits of laughter from both of them. “I look like a chicken.” Sam pulled the offending hairpiece off.

The sexy-Latina brunette wig with red highlights was better. Sam settled the long, straight locks around his face, toying with the ends. “A lot better. Hmmm…” Vicki set that one aside.

Black was deemed too much for Sam’s features. A soft honey-blonde pageboy looked beautiful, but wrong for the evening. “You want him to want to ravage you, not sell him life insurance.”

So, Sophia Vergara it was.

On to the clothes. Vicki led him into the bedroom and flung open her closet doors. It was jammed with women’s shoes and clothing of all kinds and a range of sizes—sequined/feathered drag outfits, sensible office clothing, body-conscious dresses for clubbing, everything a fashion-forward cross-dresser could need.

Vicki was initially fixated on him wearing jeans and a short t-shirt, but Sam felt that was too close to what he normally wore. And besides, he’d shaved his damn legs.

So she tried him out with a few tight dresses. “Incredible. You look so good. It’s not even fair.” And Sam did, turning in front of the mirror, smoothing the fabric over his hips, wobbling only slightly in the black heels they’d found that fit him perfectly. He had been practicing in secret for a while now, with the heels Dean had bought for him along with the pink satin panties and skirt.

But nothing was quite right.

There, in the corner of the closet, he saw it. Just the edge peeking out. A simple black leather miniskirt. The kind of soft, buttery leather a man couldn’t stop himself from touching, whether it was on the seat of a car or stretched over a round, tight bottom.

“That. That’s it.”

And he was right. The black leather clung to his hips, framing his ass beautifully. He couldn’t keep his own hands off his backside.

“To quote the immortal bard, fuck me with a chainsaw.” Vicki chewed her lower lip and closed her eyes.

She rummaged around in a drawer until she found the perfect shirt: a woman’s low-cut t-shirt, cut off at the midriff.

“Led Zeppelin. How the hell…”

“Someone left it here. Guess I’ve been saving it for you.”

Vicki put a black bra on Sam, popping two inserts into it, settling them into place. “When you’re ready to get dressed for real, we’re gonna put a line of medical tape right here and give you some cleavage with your own skin, so it looks like the boobs are yours.” She slipped the t-shirt over it, and arranged the red wig on his head.

“You still need makeup, but what do you think?”

Sam stared at his reflection in the full-length mirror on the wall. This was going to work. Holy hell. This was actually going to work.

“So there’s one big thing we haven’t talked about.” Vicki’s eyes darted to the front of the skirt. “You said you wanted to do this right. So I need to show you how to do something. It doesn’t hurt. But it will feel weird at first. Before you go through puberty and your balls drop, they’re naturally tucked up inside your abdomen, and those little cavities are still there. So you can just pop them back inside and…”

“I’ve tucked before.” Sam’s face was painted with a curious mixture of embarrassment and pride.

Vicki just stared at Sam, mouth open slightly.

“You…you have?”

Sam turned around, dropped into a crouch, reached between his legs on the right side, then the left, then between his legs and stood up. He hiked up his skirt, a sly smile playing across his lips. The front of his panties was completely flat and smooth. Like a woman.

“Holy shit. Where did you learn to do that?”

Sam pursed his lips like he was the cleverest boy in the world. “Internet.”

~

Sam had been shaved, waxed, rubbed with soothing lotion, powdered and fed. He’d showered and cleaned himself thoroughly (using his special kit he brought with him to make sure he was completely ready for Dean), rubbed himself with soothing lotion again, tucked and taped himself with Vicki’s medical tape, donned the silk and lace bra and panty set he’d picked out himself, nestled the breast inserts inside, let Vicki run a line of tape across his chest to create surprisingly realistic-looking cleavage.

Vicki set down the makeup brush, and pivoted the chair to face the mirror. “What do you think?”

Sam couldn’t speak.

He didn’t recognize himself in the image in front of him. What was in front of him was a strikingly beautiful woman. Not a man in lipstick. A woman with full lips, beautiful brown eyes and luxurious brunette hair, with breasts and holy shit that was him.

“Stand up.” Vicki guided him to his feet and walked him to the full-length mirror.

The illusion was astonishing.

“I told you. Didn’t I tell you? You look beautiful in drag. Like a model.”

And he did. Sure, he was tall, and yes, well muscled, but he hadn’t been gym-rat ripped like when he had no soul for a long time now, and the muscles seemed softer now, not at all out of place on a woman. He looked like a female athlete who’d gone into modeling.

Suddenly, he shivered and rocked unsteadily on his heels. 

Vicki settled him down on the couch and brought him a shot of bourbon. “To steady your nerves.”

Sam tossed it back neat, with a stiff wrist, a long-practiced movement.

“Scared?”

“Yeah.”

Vicki sat down next to him. “Why? What exactly are you afraid of?”

“That he’ll freak out.”

“May I remind you that Dean bought you a pair of high heels, a skirt and blouse and a pair of shiny satiny pink panties? Bought them for you? Asked you to wear them?”

Sam smiled. “You’re right.”

“And what was his reaction again when you did wear them? Wait. It’s ok. You don’t have to tell me again. I remember.”

And so did Sam. Vicki was right. There was no reason to be afraid Dean would flip out on him. Sam knew in his bones how much Dean was going to love it.

“So, what else?”

This was the real fear. “That someone’s going to see me like this. Or see me with him. And kick my ass.”

She nodded. “I’ll be honest. That fear’s real. I know.”

Sam cocked his head. Waiting.

“I got jumped last year. Stupid of me. I left the club alone. Two guys dragged me into an alley and beat the snot out of me.”

Sam felt a familiar, protective surge well up in him.

“But one, you’re like 6’4” and I can tell you know your way around a bar fight. Two, we’re taking a cab to the bar, so you won’t be alone going in. Three, it’s a bar for trans people and allies, so it’s as safe as it gets. And four, you’ll be leaving with Dean. And that man would rather die than let anyone hurt you.”

She didn’t know how true that was.

But still, he was afraid.

“And if you’re afraid of someone on the street saying something mean? Trying to make you feel bad? Anyone who tries to tell you that you’re wrong for being who you are? For loving the man you love? They’re full of shit. They’re wrong.”

These words, carrying greater force for Sam than Vicki could possibly know, forced a few sharp tears from Sam’s eyes.

“Come here, you big baby. You’re going to spoil your makeup.” Vicki fussed and preened over him until he had composed himself.

There was a honk from out front. “Cab’s here. Time to go.” Vicki checked her watch. “We’ll have enough time to get a drink or two and get you comfortable before he gets there.”

Sam sucked in a deep breath as he crossed the threshold and stepped out into the indigo light of early evening. The sky did not fall. Nobody screamed, “Freak!” at him in horror. In fact, he received an appreciative look from a passing bike courier, and the cab driver held the door open for him, ready to take him to where he would meet Dean.

Comments

[sammichgirl]

Oh, the picture in my head. This is so damn hot, I cannot wait for Dean's reaction!

And, I love Vicki. I have friends that are transgender, and this speaks to me in such a positive light. Awesome character.

[justinedelarge.livejournal.com]

I do as well, and it's really important to me to get this aspect as right as I possibly can. I'm glad this character comes across to you in the way I tried to write her.

Thank you.

[kinkajou.livejournal.com]

OK, now you made me really-really want to see Dean's reaction! :D And also a picture. I wish someone made art for this :)

[justinedelarge.livejournal.com]

If you know of any Wincest artists you think might want to do something for this, please let me know, or them know. I would love that so very much.

[kinkajou.livejournal.com]

I don't really know people, sadly :( There is a possibility that I will give it a try myself, but I don't really think I'm able to do it right :(

[deansdirtybb.livejournal.com]

Loved this: “Don’t do that to yourself. There’s enough bastards out there trying to make us feel that way about who we are. Who we love. They call us freaks.” Vicki is a hero in my mind, made even more so by very real feelings and hint of insecurity behind her bravado. Every one of us who loves in some "non-traditional" way has been there.

[deansfangirl.livejournal.com]

yay yay yay! This is soooo great, and I'm completely astonished that I'm even reading it at all, lol. Just not my kink. But Sam and Dean can apparently make me love anything...with your help! :-) Can't wait for the next chapter!!

[justinedelarge.livejournal.com]

The funny thing is it's not my kink at all either. But I was writing a one-shot, and I swear, it's like the characters themselves wanted it to go this way. And they like it. So I like it. It's totally weird.

[kinkajou.livejournal.com]

LOL :D It's also not really my kink either, but you still made me like THIS story :)and I just KNOW that DEan will like it SOOO much, and it totally epic :) It already happened a few times before that I liked crossdressing fics... because, you know... J2/wincest... if THEY do something, that makes it hot, no matter what :D) I think the only part of crossdressing (if that even really counts)I've always liked totally in my own :) is a guy in panties. But the appeal is kindof the part where the guy is hard, and... so, the tucking part is... hehe, OK, I'll just shut up now :)

[justinedelarge.livejournal.com]

Oh, our baby boy is gonna untuck real soon... and give Dean a private show... and, oh, you'll see.

[melacreature.livejournal.com]

IT'S HAPPENING!!!! Dean's gonna be there in just a little while!!! Oh, but d'ya think he'll be a tiny bit upset that somebody else touched His Sammy? Oh, wow! And Vicki! I have several transgender friends and I think you're doing an absolutely fabulous job portraying her as a strong woman in an odd world. "Freak" will not be allowed to be used as an insult any longer, damnit! We are taking it back! Just like bitch and cunt and whore and fag and queer...they can't hurt us with our own compliments. Never, again! I like your mind, have I ever told you that? 'Cause, it's true. I can't wait to see Dean's reaction! I wonder if Sam'll even get to finish his drink before Dean's haulin' him out the door:) This is gonna be so fucking hot!

[masja-17.livejournal.com]

You made Vicki so real, thanks!

Love <3