justinedelarge | Pretty in Pink (Isn't He?) Chapter 4: Sack and Crack Wax

Author: justinedelarge
Fandom: Supernatural
Pairing: Sam/Dean
Rating: R
Words: 1260
Warnings: Wincest, D/s, crossdressing, graphic description of waxing
Disclaimer: I don't own what I don't own.
Summary: In order to complete the physical preparation for Sam's male-to-female makeover to surprise Dean (who loves his Sammy in pretty pink panties), Sam needs to let Vicki wax his ass crack and scrotum.

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 made a sound. 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.”