"Baby, don't be nervous." Her glossy fingernails rake against the buttonholes of his white shirt. Sweet-smelling fingers unknot Jimmy's wrinkled, navy-colored tie.

Chastity murmurs into his ear, grinning, "I'm going to take good care of you…"

Another wet, messy kiss with her palms sliding slowly over his stubble-rough jaw line. His own lips remain lax against hers, pliant and obedient when the woman's tongue presses past the seal of his warm mouth, but completely unwilling to return her over-enthused affection. She breaks the kiss, faintly scowling with irritated concern, staring down at him lying between her straddling, bare legs — that ugly, beige trenchcoat crumbled and pooling across the bed. His soft, black hair tousled and stuck up from fooling around.

She thinks that his blue eyes, such a sweet quality, examine her a little too intensely for them not to be heading to the main event. "What's the matter with you," Chastity asks, adjusting her spilling breasts in her white bra-top. "Can't get it up?" Checks by squeezing his crotch. Limp as spaghetti. She curls a lip, leaning in and sniffing the air.

"Don't tell me you're high."

The statement finally makes Mr. Mystery Man react, furrowing his dark eyebrows.

"I do not understand… I'm not situated above the ground," he says, all gruff voice, and she fights back the urge to laugh at how absurdly bewildered he sounds.


Technically, she's not supposed to drink while on the job.

But there's a bottle of chardonnay in an ice bucket on the table and a sexually confused Hottie McHottie in her assigned room, so, the rules can be overlooked for a while. "Cas, right?" Chastity watches the silent, purposeful nod over the rim of her fluted, clear wine glass, and picks up conversation. "And so… this Dean guy? He's not picking up on it at all?"

"It would appear so." He sighs. It sounds pretty frustrated to her. Must have been crushing on this guy for ages, bless his heart. "He's often preoccupied with his brother or women."

"Best way to let him know you're into him is to just be direct, y'know?" She pats the top of Cas's knee encouragingly and offers him a sip from her glass, lifting it to her lips when he doesn't move to accept it. "If he's crazy about blowjobs then get your flirt on, tug down his pants, and go to town on him, honey. It definitely would be sending him the signals."

"What if we're already located in a town? Should we perhaps then move to the next available one?"

Holy crap, she should feel embarrassed or something… she hasn't giggle-snorted since she was in grade-school.

"Omigawd, you're so cuu~ute." Chastity wipes at her mouth with her fingertips, smiling big when he cocks his head slightly. "Okay, if you're not into giving a blowjob, getting him off with your hands works just as well," she advises.

"You mean, allowing Dean to experience an orgasm through touch instead of penetration."

"Totally!" Her light brown eyes flick towards the clock. Oh.

"Well, baby, sorry but it looks like our time is up," Chastity says, shrugging and reaching down to straighten her bunched, white panties. "But, listen, you need to remember a couple things." She makes sure his serious expression and those ridiculously blue, blue, blue eyes are focused on her before Chastity starts counting them off on her salon-tanned fingers. "One: Life is short, okay? There's no chance at it again if you pass up on the things you love. Two: You're both insanely hot, so… Three: Why the hell not?"

Another knee pat.

This time, Cas smiles curiously back at her, and he may be emotionally stilted or something funky like that, but daaamn, he's fine.

Good luck with that, Dean guy.


Little Miss Walking Kismet comes right up to him with a sunny smile, flipping the end of her see-through nightie, playfully.

"He's all yours, sweetheart," she trills, glancing over her shoulder to wink coyly at Castiel before strolling past Dean.

Dean wraps an arm around his buddy, punching his shoulder lightly.

"How'd it go?" He asks, "Awesome, wasn't it?"

"It was oddly pleasant," Castiel agrees, somberly. "She was very informative, and her soul is… pure for her occupation as a wanton whore."

The hunter bites back a growing smile. "Atta way, champ." His hand claps Castiel's back congratulatory. "I knew you had it in you to loosen up a little." Moss green eyes light up as Dean steers him towards the brothel's exit, smirking. "Sex was freakin' good, right?"

Castiel shifts a moment and then frowns at him. "We did not engage in sexual intercourse," he says, dismissively. Dean's friendly arm removes itself from his neck and shoulders.

"Then what were you doin' in there for forty-five minutes?"

"Conversing. I have already mentioned that she was very helpful."

Dean scowls at him on the sidewalk with an outright 'you gotta be KIDDING me' look. Frosty vapor emerges from between his lips from the bitter cold as he growls, "Dude, I gave you five hundred in cash to get some tail, not advice from your hooker—"

"Dean," Castiel interrupts him, eyes intently tracing his features. "I think you and I should copulate." Dean's mouth slams shut from what remains of his angry ranting, green eyes bugging out, and his dick taking a lot of interest in the possibility as the angel suggests flatly, "Aggressively."

Generally, very little on the subject of sex could catch Dean Winchester off-guard — except fucking machines; he's never considered ever saying yes to one of those things. But, the Nerd Angel actually wanting to grind nasties with him? Uh, yah, color Dean surprised. Not that Castiel hasn't been a frequent round of his shower masturbation fantasies before…

But that's all they were… they were just fantasies.

"Dean," a repeated, breathy murmur.

He snaps back to attention, to reality, when Castiel presses them against the outside wall with his angelic strength, right beside the entrance door, Dean's head gently falling back against the bricks. Only two or three people roaming the district area pass by to stare, either with leers or in discomfort.

"Cas," Dean answers him, finding his arms freed.

He grabs Castiel's biceps, letting out a wordless, short groan when eyelashes tickle against the base of his throat. A closed, dry mouth brushes right under his left ear. The angel lifts his hand, pinching his thumb and index finger together and making a complicated, downward motion.

Dean's fly, painfully restricting him in his jeans, hurriedly unzips by an invisible force and he hisses out his approval, "Cas, fuck…"

"If that's what you want," a heated, devoted whisper, "but you're going to orgasm when I tell you to, Dean."

Dean can't manage it to suppress the lightning-hot quiver running up his entire body, at Castiel's quiet proclamation of dominance against the sweaty flesh of Dean's cheek. Jesus christ, he's going to bottom bitch, and… freakin' love every second of it.


"Night, Todd," Chastity yells back, blowing a sly kiss to the burly security guard waving in her direction and closing up the brothel. He offered to walk her to her car tonight, but it's only across the street, and plus, the white stilettos in her right hand were good and sharp.

She grasps her thick, faux fur-lined jacket closer to her body as the blonde woman runs across the empty street, digging for her keys. She thought about Hottie Mc—Cas, for a brief second, and hoped at least he and his gay love interest were having a late night coffee. Or having a beer at one of their apartments. Something, anything to get the ball rolling.

The all black Chevy parked two spaces from her car rocks in place, enough for her to give it a double-take. Fogged up windows. No interior lights on. Two dark shapes in the backseat.

Chastity snickers into her hand, unlocking her car door.

Must be nice to be that carelessly in love.


DeanCasKink prompt:

"Prompt: Dean/Cas, Chastity made them do it

Alternate version of 'Free To Be You And Me' where instead of pissing the whore off, Castiel refuses to join her and finally comes out of the closet."