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Pick Me Up

Summary:

After some rough days on the road, Char is offered a pick-me-up by his longtime friend Cindy.

Notes:

(See the end of the work for notes.)

Work Text:

"Wherever y'all are headed next, I'm sad I can't come with," Cindy says, with an affectionate squeeze. "But, somehow... I don't feel we'll ever be too far apart."

The hug between Char and Cindy continues for a moment, but breaks away eventually.  “Thank you Cindy, seriously.”  Char smiles, but it doesn’t quite reach his eyes.  “It’s been… A rough few days on the road.  Gettin’ to see ya again, and now this jacket… It’s the best thing to happen to me in a lil’ while, I mean it.”

“Ah Char,” Cindy coos, patting him on the shoulder as her eyes flutter shut for a second in a smile.  “Ya sure do know how to make a gal feel special.  But..” She trails off, eyes opening again as she looks intently at him.  “...I feel like you're the one who needs to feel a lil’ special right now.”

Char chuckles, shaking her hand off his shoulder.  “Shucks Cindy, the jacket ain’t enough?”

“Not right now it ain’t, look at ya!” Cindy says, stepping forward.  “I’ve known ya long enough to know when you’re hurting, Char.  I see it in those eyes, ya look like a puppy that’s just been kicked.  Lemme help get those bad days off yer mind, even just for a little bit.”

Char knows better than to argue with her when she’s like this.  “Allllriiiight, Cindy,” he drawls.  “What is it exactly you’re thinkin’?”

Cindy’s grin, originally full of kindness and flecked with concern, suddenly grows almost mischievous.  “Ah’ knew you’d see it my way.  Well, it’s just you and me here, and the beds here are mighty comfy, so Ah’m hoping I don’t gotta spell it out for ya.”

Char froze.  Well, his muscles did.  He was still as a statue, even as most of his blood rushed to his face, and some to somewhere unmentionable. 

“Ah, Cindy, that’s, uh.  Cid?  You’re with Cid ain’t ya?  I- I ain’t wanna get between y’all-”

Cindy simply laughs as Char tries to stutter out some sort of response.  “Cid and I have an agreement.  When we were making arrangements and such for me to be traveling about all the time, we realized something.  Frankly, we both have such a big drive for this sorta stuff we thought we might both go a bit nutty if we were apart for too long.  So, he’s got a bunch of local cuties who know I appreciate them keeping him company while I’m on the road.  He’s real popular, to be rather honest.”  She sighs, briefly staring off into space.  “And ancestors do I get it.  I’m a lucky gal, Char.  The way he makes me feel…” Cindy shudders.  “He an’ I are soulmates, gotta be.  But, to the topic at hand, that means I also make do with the folks I meet while traveling.  Made some real interestin’ friends this way, lemme tell ya.”

Char stands there, not even blinking as Cindy explains things to him.  His eyes dart up and down, looking at the friend he’s known for about as long as he can remember, but now entirely in a new light.  Not entirely new, he’s been crushing on her for a while, but he’d always figured those thoughts best left to fantasy, especially once she got with Cid.  He liked Cid, and he liked seeing Cindy happy, and he didn’t wanna get in between that.  But if this was what made Cindy happy…

“I want to.  I wanna do this.  I’ve wanted to do this for a long time but reckoned I woulda been a bad friend for asking while you were with Cid, and I've never done this with anyone before, and-” Char blurts out all at once.

Cindy laughs, openly and joyously, interrupting Char’s well meaning outburst.  “Well shoot Char, I guess I had my nose buried too deep in my work most of the time, I never noticed. But,” she claps her hands on both Char’s shoulders, pushing him gently and marching him backwards towards the bed.  “We can make up for lost time now.”

Char only has to step back a few times before he feels the bed against the back of his legs.  With a thump, he falls back into a sitting position, and Cindy slides into his lap, smooth enough that he can tell she’s done this many times before.  Her lips are against his mouth before he can do so much as react.  He’s never kissed anyone before, but he vaguely understands the concept of kissing at the very least.  He tries to lean into it, rather clumsily, but Cindy manages to make it work.  Her arms wrap around his shoulders while his hands settle on her hips, as they slowly get used to making out.  It’s certainly a learning experience of some sort for Char, one that ends all too soon.

Though when Cindy slides off his lap to her knees and starts fussing with his belt, Char finds he doesn’t mind the kissing ending so soon all that much.  Cindy quickly gets his pants undone, and slides them down just enough that his cock is freely exposed.  Cindy gives it a quick kiss, turning her gaze up to look at him.  “So this is what I’m working with tonight, huh?  Nice sight, you certainly don’t disappoint, Char.” 

Char can’t help but blush once again.  He opens his mouth to respond with Ancestors-knows-what, but any halfway witty response dies in his throat as Cindy takes him into her mouth.  Instead, he moans as Cindy begins to bob her head on his cock.  She takes him slowly, almost methodically.  She teases her lips up and down his length, licking with her tongue.  Char breaths through gritted teeth, trying to bite back moans.  He is unsuccessful, to Cindy’s clear delight, as she giggles with him in her mouth.  She bobs a few more times, and Char barely knows what to do with himself as pleasure courses through him like he’s never experienced.  He reaches for the source of the pleasure, letting his hand weave into Cindy’s hair, softly gripping as she continues to bob.  She coos, leaning into his hand, only encouraging his grip to get tighter.  She takes him deeper with every bob, pausing briefly once she’s taken all of him.  She bobs a few more times, and with how deep she’s taking all of him now, Char doesn’t think he’ll last.

But it's just as Char is getting close, Cindy stops.  

With a pop, Cindy pulls off Char’s cock, smiling wide as she stands up.  “Think I got ya good and warmed up, but I ain’t want you finishing quite yet.  Now c’mon,” She says, slipping off the top of her coveralls, “much as I think my jacket looks cute on ya, take it all off, lemme see what I’m working with.”

Char is fast to strip down, his clothes coming off in a flurry.  His jacket and chef undercoat are quickly tossed aside, boots and pants soon following.  And yet, all the while, he can’t take his eyes from Cindy.  She’s not making a show of undressing, at least no more than he is, but ancestors he’s still enraptured by her.  Her coveralls are slipped off, boots kicked off, and all she had on underneath was a tank top and panties.  Those join the pile of scattered clothes quickly, and she notices his stare as they finish undressing.  “Like what ya see, cutie?”  She poses briefly, lacing her fingers behind her head, making sure everything is on display.  Char nods furiously.  He has no words for this.  The way Cindy beams lets him know the message was received.  “Good.  Now get on that bed again and lay back.”

Char happily obliges, laying back and getting comfortable with a pillow under his head.  Cindy is quick to hop onto the bed, crawling over to sit above Char’s lap.  Char once more takes in the view of his longtime friend, completely naked before him, and almost whimpers simply at the sight.  She is gorgeous, and he needs to be back inside her.

“Alright there sugar,” Cindy says, voice dropping to a husky almost-whisper.  “You just let Cin here take care of you now.”  She reaches down, taking hold of his cock, and slowly lowers herself onto him.  Inch by inch, Char slides deeper into her cunt, groaning at how wet she feels.  He almost can’t believe it’s him making her feel this way.  He can only hope she feels at least a fraction as good as she’s making him feel.  Cindy takes him all the way to the base, softly moaning as her thighs become flush with his.  Char shudders at the noise, at that little bit of extra confirmation that she likes having him inside her.  “Mm, fuck Char,” Cindy groans.  “Ya really do fill me up just right.”

“Fuck,” Char groans at that.  “Cin,” he huffs, trying to hump upwards, desperately trying to find some friction.  “I really don’t think I’m gonna last long.”

“That’s alright sugar,” Cindy says, placing her hands flat against his stomach, starting to bounce on his cock.  “I just want ya to fire off when you're ready.  Tonight’s for you, you can set whatever pace you need.”

Char swears again.  At least he thinks he does.  Everything is quickly becoming a blur.  He’s entirely too focused on watching Cindy ride him, watching the way her tits bounce, the way her hair sways, framing her beautiful face.  Watches the way she bites her lips as he does his best to clumsily thrust up into her, again and again.

“Cin,” Char moans.  “Cin, Cin, Cin, Cin-”  He’s cumming.  He can’t hold it back anymore.

“There ya go sugar, fill me up best ya can,” Cindy coos, and drops down onto his cock one last time, letting Char twitch and spill inside her.  His hands grip her hips tight, his fingers leaving indents on her flesh.  His back arches as best it can, and a strangled moan escapes his throat.

As quick as he starts, he’s done.  He takes a heavy breath as Cindy giggles.  She leans forward, sliding slightly off his cock, but not all the way, as she takes his lips in another kiss.  Char does his best to keep up, breathlessly returning her affection, but his mind is still swimming, and his lungs beg for air, so eventually he’s forced to turn away, and Cindy relents.

With the kiss broken, Cindy finishes sliding Char out of her, his cock falling limp between his legs, and she falls with a thwump , landing next to him, cuddling him close.

“I was, hah,” Char breathes, “A bit of a quick shot, huh?”

Cindy snorts.  “Ya were, but don’t worry, everyone is their first time.  Hell, even big manly boys like Hal can’t last long their first time.”

“Thats… thats good,” Char manages to breathe out, finding some comfort in that.  And as oxygen slowly returns to his lungs first, and brain second, the implications of Cindy’s comforting words are absorbed.

“Hal?  You were Hal’s first time too?”  Char asks suddenly.  “You and Hal fuck?”  He adds, completely redundantly, totally flabbergasted by the admission.

“Well, we have quite a few times, to be honest,” Cindy says, gazing at him all the while.  “Don’t tell him I told ya though, the big guy gets real flustered talkin’ ‘bout this kinda stuff outside the bedroom.”  Cindy sighs, gently nestling her cheek against Char’s shoulder as she gets comfortable.  “Shame, cause he’s real good at it too nowadays.  His ropework skills?  Not just fer lassoing cattle, y’know?  He’s real handy too, you should see some of the equipment he’s built.  Get me thinking about that breeding bench a’ his and I’m liable to start blushing, thinkin’ ‘bout all the time I’ve spent bent over it.”

Cindy says she would blush thinking about it, and yet Char is the one blushing at the thought of it.  His two closest friends, one tied up, the other fucking her over a handmade livestock contraption.  And with one of those friends to be with him now, to still be very much naked, and very much pressing that naked body into his as they cuddled…

Char’s cock didn’t stay limp for long.

“Hey, uh, Cin,” Char says, as he feels himself getting hard again.  “I don’t think I’m done.”

“Didn’t think ya were, Char,” Cindy says, separating from him only slightly, kissing him on the cheek as she lets her face hover over his.  “Want me on top again?”

“Actually,” Char starts, taking hold of Cindy and rolling them both over, something she happily yields to.  “I wanna try bein’ on top this time.”

“You’re the boss tonight, sugar,” Cindy drawls, getting situated under Char as he takes a moment to line himself up with her.  “I do rather like when cute boys take charge; show me what ya got.”

Char slides back into Cindy, moving slowly, carefully, getting used to being on top.  It’s new to him, but somehow it feels right.  There’s a barely audible squelch as Char fills her up once more, pushing some of his own cum out onto her thighs.  Slowly, he experiments with rolling his hips, practicing the motion, getting comfortable with it.  He seems to be a quick study, and quickly figures out that Cindy likes it when he snaps his hips forward fast, if the way she bites her lip is any indication.

“There ya go, sugar,” Cindy coos once more, “Keep doin’ that, that feels real nice.”  Char wasn’t planning on stopping anyway, but now he definitely isn’t.  He feels good, she feels good, everythings going just fine.  Better than fine, it seems, as Cindy’s breaths start to come quicker, sometimes interrupted by little moans.  She’d stolen his breath with a kiss earlier, and now Char reckons it’s time to return the favor.  He leans forward, something that he finds to be a surprisingly difficult maneuver.  He steadies himself by placing a hand next to her face, making it look like he planned it by cupping her face with it as he dips down.  Their lips meet clumsily, only barely staying together as Char keeps thrusting into her.  But barely is enough.

“Hah, Char, lookit you,” Cindy says as Char kisses her cheek, missing her mouth on this thrust.  “Gettin’ me all riled up.  Keep doin’ what yer doin’, if ya wanna see what I look like when I cum.” 

Char, obviously, needed to see that.  Though he already felt the rising tide of his own orgasm on that way again, he was already much more effective at staving it off.  He did exactly as Cindy asked, keeping the pace steady, thrusting into her deep, keeping his hand cupped against her cheek as she nestled into his palm.  Her moans slowly grew louder, from whispers to wanton sounds, and suddenly, her legs were wrapped around his hips.  With Char trapped, Cindy began rocking her hips in time with Char’s thrusting, making his movements so much easier, and a bit less clumsy.

“There we go, there we go, ah, hah, there we go- ha-ah!”

With a sharp intake of breath, Cindy cums, and Char is treated to the delightful feeling of her fluttering and contracting around him, her leglock tightening as she pulls him in as deep as he can go.  And ancestors, the face she makes is the real prize.  Eyes screwed shut, mouth totally agape in a silent moan,hair beginning to stick to her forehead, having long grown moist with sweat.  There’s nothing Char can do but lean in, sealing her mouth with a searing hot kiss, filling the space with a moan of his own.  

Cindy twitches under Char a few times, her body shivering with waves of climax, slowing after some time.  The two friends are left panting as their lips separate, both sweaty, drained, and smiling like fools.

And yet, not quite done.

“Go on now,” Cindy says, rolling her hips again.  “Don’t stop on my account, ya got one more in ya, ain’t’cha?  I said tonight was ‘bout you, even if that means you gotta use me like a toy t’ finish off.”

Char almost cums at the way Cindy insisted upon using her.  Almost, but he manages to hold off.  For a few thrusts at least.  He rolls his hips, snapping them forward about four more times before once more spilling into Cindy, filling her enough that she is leaking when he pulls out.  He only just barely manages to roll to the side, rather than collapsing right on top of his friend.

“Fuck, Cin,” is about all Char is able to say.  “That was incredible.”

“It was real nice, Char,” Cindy hums, smiling as he cuddles into her.  She rolls to her side, looking him in the eye now.  “Feeling better now, I hope?”

Char had pretty much forgotten his difficulties on the road by this point.  Way too much else swimming around in his mind now.  And now that it had been banished, he finds it’s easier to not let those thoughts about himself creep back in, at least for now.  “A lot better, to be honest.  I feel… good.  You made me feel real good, Cin.”

“Aw,” Cindy coos, “Ya made me feel good too, Char.”

“...I’m no Cid yet, though, am I?”  Char says with a laugh.

Cindy snickers.  “Hon, no one is like Cid.  Trust me on that.  That man can fuck.   Though, hmm…”  Cindy briefly loses herself in thought.  “Maybe next time we’re all in the same place, I’ll get ‘im to show ya first hand.  See if he can’t teach ya a thing or two.”

Char gulps at the offer.  “That sounds real nice, and yet mighty intimidatin’.”

Cindy laughs again.  “Well, no one can fuck like Cid, but that don’t mean ya can’t be pretty good too one day.  We’ll get ya there.”  Cindy gives him a quick peck on the cheek.  “Yer just gonna need a lot of practice.  Cid’s got quite a head start, so anytime you wanna go again, you come find me, ya hear?”

“Any time?”  Char echoes.

“Any time.”  Cindy confirms.  “‘Cept maybe tonight.  I’m a bit beat now.  Lemme go get cleaned off and we’ll call it a night here?”

“You’re not leavin’, are ya?”  Char asks as Cindy gets up, making her way to the washroom. 

“And miss out on cuddling ya tonight?  Not a chance, cutie,” Cindy answers over her shoulder.  She’s only gone a minute before she’s back in bed, settling into Char’s arms.  Char wraps himself around her tight, and she seems content to let him be the big spoon.  

Comfortable and spent as they both are, it does not take long for sleep to find these two friends, closer now than they ever have been before.

Char is woken the next morning to the sound of birds singing and fabric rustling.  His eyes slowly crack open, and he sees Cindy nearby, tugging her coveralls up her legs, yet still topless.  He is treated to the timeless sight of her chest jiggling as she bounces a little, working the fabric up her legs.  He sits up, which is finally enough for Cindy to notice he’s awake.  

“Ah, mornin’ sunshine,” Cindy smiles at him.  “Didn’t wanna wake ya, was hopin’ to get back out there and look at that magitek you brought me.  Sorry fer tryna sneak out on ya, but I’m just real curious, y’know?”

Char laughs.  That's the Cindy he knows alright, can’t keep her mind off magitek.  Unless she’s in the mood where she can’t keep her mind off fucking, as he learned last night apparently.  Though, seems he’s not much better right now, ‘cause watching her dress, watching her walk around topless…  He’s already feeling himself stir again.

“Be a gentleman and hand me my top there, wouldja?”  Cindy asks, pointing to where the garment lay on the bed next to Char.  He grabs it, standing up to hand it over to Cindy, only to pull it back right at the last second.

“So, last night,” Char says, while Cindy cocks her head to the side in a brief bit of confusion.  “Ya did say anytime.”

Cindy laughs, her eyes narrowing as she looks him up and down.  “Goodness, insatiable, ain’t ya?  Maybe I’m gonna be the one in trouble when I get you and Cid in the same room one day.  So whatcha thinkin’ this time?”

“Well,” Char says, dropping her top and remembering how ‘she does rather like it when cute boys take charge,’ takes her hand into his own and leads her back to the bed.  With a sudden movement, he spins her around, placing his palm between her shoulder blades, pushing until she bends over.  He yanks her coveralls back down to her knees, and places his hands on her hips, lining himself up.  “Thinkin’ something like this.”

“Well, I’m all yers, cutie,” Cindy says, looking over her shoulder. “Take me how ya like.”

“Don’t worry ‘bout not getting to your magitek,” Char says, “I still don’t think I can last long, ‘specially with you, but,” Char thrusts into Cindy once more, moaning as he does.  “Practice is practice, right?”

Cindy hums in agreement.  “Practice with me all you like, cutie, yer gonna need it when I get you with Cid.”  She winks over his shoulder before letting her face fall against the bedspread as Char begins fucking her in earnest.  “When we gang up on ya, yer gonna need it.”

Notes:

Turns out all I have energy to write right now is original fic. More to come? Maybe?

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