πŸ“š what-if Part 44 of 23
what-if-44
EROTIC COUPLINGS

What If 44

What If 44

by nycrooftops_
19 min read
4.29 (5300 views)
adultfiction
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As is a theme for me at this point - friends to lovers with a build up. What can I say, it's fun to toy with the strange and new of something also comfortable? The (literal) feeling your way through. Hope you enjoy!

Content warning: mention of drug and alcohol use.

Worth note - this work (along with all my writing) is copyrighted and may not be reproduced in part or whole anywhere without my written consent. Thank you.

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"I want to watch you have sex with yourself."

"You what?"

"Tonight."

Her eyes are unflinching, settled - focused. I don't know how to think or move under that gaze. The gauntlet has been thrown down, there's no way out of it. Lessons have been learned, namely, don't talk a big game about 'whatever you say' when you propose a bet. She's not to be trifled with when she declares victory.

"I'll set the stage, you just have to show up... wearing only your pants."

That cool smile, it stirs something in me.

"This feels extreme."

"Excuse you, might I remind you of the last time I owed you a debt? I wound up walking naked through a pub."

"It was half four in the morning! The only people in there were you, me, Frank passed out in the corner, Jenna - who sees you naked daily, and might I add, why I chose the claim, since you boasted about being a naked person, constantly flitting about unabashed - and Colin the barman shied his eyes away because he is a gentleman."

"You looked."

"That was the point."

"And I have a point as well."

What she could mean by this causes me to swallow unintentionally. I feel my throat go dry.

"Well, I guess then -"

"Exactly, see you at eight!"

She hops out of her chair as airily as if she'd just said - 'See you at the game! Be sure to wear team colors!' There's a fluttering about my chest. The mix of turned on and freaked the fuck out I am is causing system wide malfunction, I go to reach for my drink and miss by a mile.

'Have sex with myself,' I think. All of a sudden, I forget entirely how to go about it. Conscious of the fact that I'll be watched - nay, observed, studied, by a wily goddamned minx - I feel my knees shake. If I was standing just now, this table would go down with me - and yet?

I let the idea play out in my head, before remembering I'm in public, and I snap to wondering who could have heard all that was said. I look around and everyone's wrapped up in their own intrigues, I'm alone with my very loud thoughts.

Right, what next. A shower, food? Should I bring her food? Stupid, this isn't a date. What the hell am I even thinking? What the ever-loving fuck did she mean by she 'has a point.'

I calm myself down long enough to pay the bill and set my course for home. I've got six hours to prepare for, whatever this is, and what the fuck do I do until then? I decide to hop on my bike and race around the city. If my pulse insists on being high I might as well do something with all this unsettled energy.

Exhausted, starving, sufficiently distracted, I'm back at mine and there's a text waiting for me.

'Is she mental,' is my first thought. This is not a lost bet, this is some kind of vengeance. Must not have like that pub stroll one bit, I'm realizing. She's toying with me.

On my phone is a photo of her legs - those ridiculously sexy, toned legs - in sudsy bathwater, the photo cropped just so I can almost -

'Eight years, countless trips, concerts, drunken nights - and all the opportunities that come with that foolishness, we get on like a house on fire and not even once an accidental kiss or flirty touch.' I proclaim to thin air, 'And now she wants to watch as I bring myself to orgasm.' That flush rushes through me again. 'What is her point? When I had her strip down it was to prove she wasn't as blasΓ© and liberal about her nakedness as she claimed. I was wrong, but -'

"Inspiration." reads the text bubble under the photo.

'Maybe she's trying to embarrass me like I may have her. This is her way of reclaiming some power. Lure me in and cut the string. Cheeky game, darling.'

These rubbish thoughts taken hold, like any idiot I'm now looking forward to tonight's antics and to prove she has no control over me. 'I'll put on a show and have her aching for me. Uno reverso.'

Dropping trou in the hallway, I'm on my way to the bathroom, mid polishing off a bowl of cereal, feeling pretty confident. It's only after I've had time to relax in the steam of the shower that the thought occurs to me - 'Do I bring protection? Is this presumptuous? Better to just be prepared? You stupid bastard what have you gotten yourself into. She's already in your head.'

'door's unlocked'

I see the text just as I'm turning onto her street. It's not too late, I can turn and run. 'Oh mate, you're doomed,' I think, 'best to just surrender to the moment.' Deep breath - my heart slams against my chest thinking about the look in her eye when she named her claim. It all manifests in an appropriate excitement for the task ahead. 'Calm down, calm down -'

"Hey! Emma!"

Do I sound as high key to her as I do in my head?

"I thought I said in your briefs!"

"Wait, you truly meant for me to arrive here half naked in the dark? It's legitimately starting to snow."

"Eh, minor detail, at least you're here, yay! I've the room all cozy for us, c'mon up."

This feels surreal - are we both living the same day?

Speaking of clothes, taking stock, she's wearing a button front thermal, and the way it clings to her breasts, the soft slope and the heavy droplet shape, the gentle bounce as she walks, I just -

"Hey Emma, I -"

"Want something to drink?"

"I want to ask you if you're sure. You know our friendship will completely change after this. We stand to lose a lot if we're not as sophisticated as we think we are."

"You can back out at any time, you know there's no obligation and if you're not comfortable that's absolutely not okay. We've always said that of our games and it's true. You only need to say the word, invoke the clause, and we'll grab a takeaway instead. There's a funny panel show on tonight."

She says it so coolly, a smirk playing on her lips.

Immediately, my ego flares - the impetus for all dumb things done on this planet - and I decide I'm more than game. I will not be announcing to all our friends that once, indeed, I did fully snog a magazine editorial page of Alison Goldfrapp in a moment of desperate, teenage horniness that tuned my tongue a weird color from the ink. Besides, the drugs were mainly to blame - both mushrooms and hormones - and goddamnit should I never have told her that. (Yes, you guessed it, more drugs led to that confession). And yes, there's a backdown clause, and it's each of us having to admit an embarrassing secret to our friend group if we don't make good on the claim from a lost bet. It's just now striking me that we play borderline cruel games, and - ah yes, the exact wrong time to notice it, after I upped the ante. I remind myself this woman, when dared, walked naked in public - with poise, and I'm specifically now remembering the the line her body draws from her shoulder, in at her waist, down her hip, up and around her ass. Oh fuck. Oh, fuck.

Snapping out of my abstraction I see a gleam in her eye. She fleetingly bites her lip and motions to follow her upstairs. Something shifts. I realize I've never even been to her bedroom, and I really want to be there, more than anything.

I hear the beers she's holding by the neck clinking in her one hand and I'm absolutely entranced by her ass swaying before me as we climb the stairs. If I don't start some kind of meditation this will be a very brief payback.

Her room is on the top floor where the ceiling slants in, her bed tucked up against one slanted ceiling side, red flannel sheets, some candles about. My senses heightened, I see the snow begin to cling and pile at the windowsill. She's got a tune on low through her record player.

"Inviting," I manage.

"I'd hoped so, I'm not trying to embarrass you or anything."

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There goes that theory.

"I'm just curious," she continues.

"Curious? Ha! You've requested that I touch myself in front of you out of curiosity?"

"Think of the roles reversed and maybe you'll get it."

Well fuck, she's right, and now I can't stop thinking about it. I feel myself press against my pant's front and wonder how this is all going to go down, get started.

Her hand outstretched, she's offering me one of the beers. I sigh and sit on the bed's edge, she settles in a comfy, wide chair just to the side, facing it near the foot.

"Cheers."

"Cin, darling," she says, with the widest grin I've ever seen.

I start undoing my shirt and she gets up to switch the record.

"Preference?"

"You know, I've a habit of diddling myself to Stravinsky - have Rite of Spring?"

"That's truly twisted."

Her giggle puts me at ease and I find I'm getting even more excited.

"For real though? Radio Department."

"Mmmm."

The Worst Taste in Music kicks on. I smile, shake my head, and pull at my belt.

"Is this all really not for a laugh?" I ask, while she's still back to me.

"No."

She doesn't turn, I see her foot lightly tapping. That shift in the air from earlier happens again. It feels like getting deep into something. I loudly drop my belt to the floor.

"Very good," she faces me and returns to the chair, slowly sinking back into it.

I think I see her own shirt a bit undone, but I can't be sure. I take one hard pull on my drink and - fuck it, shirt comes off, trousers next. I'm standing not far from her, just in my pants, and it's apparent I'm ready for this.

"Tell me to take them off," I test her one last time.

A beat of silence, but her gaze is unshaken - I think I see the corners of her mouth momentarily twitch into a smile.

"Take them off." A hand travels to her lips and she unconsciously, momentarily covers her mouth.

Her eyes lower in a way that makes my chest flutter and cock stiffen harder, if that's even possible. The rasp in her voice makes me shiver.

I pull my pants down, my cock drops into my hand near to her face. I think I notice her lips tremble and my mind is alert to how plush they look. I step backwards to the bed. Sitting deeper into it, I make myself comfortable, leaned against the headboard. My farthest knee up, the other leg dropped open towards her, I sit like this gently touching myself while the moment settles.

"Any directions, requests?" I ask. There's a slight edge in my voice, like I'm challenging her to give something away. That she's thought about this at length, about me.

"This is your moment, you call the shots."

"Ha, do I?"

"Maybe." Her eyes flash.

I begin tugging on myself - our eyes are locked, I feel like I have to remember to breathe. The eroticism of the moment is holding me like a vice. I stroke over my head and a pant escapes my lips. She shifts in her chair. I start to wonder - what if?

The next song comes on - Pulling Our Weight

"Penny for your thoughts?" she ventures.

"You, under me."

Noticeably, even in the dim light, I see how she sucks in her breath at my directness, this fantasy. I continue to stroke myself at a measured pace. I've got to keep my cool.

She opens her mouth as if to say something, takes a deep breath and then a drink instead.

"What if I were to tangle my hand in your hair and take your lips for mine right now?"

"What if?" she returns.

My eyebrow jumps up. I see her chest heave. I stop stroking and hold still.

"What if I were to come over there?"

"And then what?"

Shifting myself towards the end of the bed, holding myself in hand, she draws herself up in her chair.

The slowness, the charge in the room, do I dare really cross this line?

"What if I were to be in your mouth? What would that be like?"

"Well, first I think you'd feel my lips part around you, soon the sensation of hitting the back of my throat, and then, I'd swallow."

Is she fucking serious?

Standing up, I motion her to come to me. She untangles her crossed legs from beneath her and moves towards me. I reach for her and pull, wrapping an arm firmly about her waist and with my other hand cup her ass.

I travel both my hands up to her neck, place them delicately around and hold her chin up with my thumbs.

"Emma, please," I hear the need in my voice, "I really want to kiss you."

She nods.

Crushing my lips to hers, I soon press my tongue into her beautiful mouth and there's a tipping point, a passion overtakes us and the measured calm that held steady before this moment melts away. My nakedness is pressed up against the softness of her clothes and I feel electric.

I pull at the band of her joggers, slip a hand between her legs and my good fucking god if she isn't soaking wet and so very warm.

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"What if I were to be caressing... kissing... thrusting into you?"

"I'm certain I'd be begging for more."

"Goddamn it," I breathe out in shock, who is this panther I've known for years? "What if I were to make you shout my name?" I mumble in-between kisses.

"Would I do it right away? How loud would I be?"

"Softly at first, initially just a moan - nearly gasping my name."

Moving her backwards, gently directing her back down into the chair, we pause. Her eyes, looking up at me, seem beckoning. She did say I was calling the shots.

Slowly, I move towards her, run my fingers along her jaw and slip my thumb across her bottom lip, gently parting her mouth and dipping a finger inside. She ever so delicately drops her languid tongue out as she opens her mouth wider and the strength it takes in that moment to take a beat -

"Are you certain?"

"Very," she says in a hushed tone, rolling her bottom lip into her mouth.

"Tell me plainly."

A flash of mischief across her face, "I want this."

"All of it?"

"Every inch." Her eyes narrow as she says this.

My knees nearly abandon me. Fuck's sake, and I'll give it all to her. 'Deep breath, deep breath,' my head shouts.

"First though - protection?"

"You mentioned last week you were tested after your last fling?"

"Yes. I'm all clear."

"Same. And I'm on BC, so that's no worries."

Settled then.

She reaches for my thigh and draws me in closer, I lean down to kiss her again. She tilts her head and kisses my hip, my thigh, teases my balls with her tongue before slowly taking me in her mouth. My legs give a slight quake, her mouth is so soft and my need for her so fucking strong.

The ceiling being slanted down enough here that I can lean an arm against it, I bury my face into my bicep as I try in vain to stifle a moan. She wasn't kidding, she takes me deep and I feel my balls tighten.

"We must get these clothes off you."

I slow things down, I'm not going to last if I let her keep sucking my cock like this.

I get on my knees, find the edge of her shirt. She instinctively raises her arms. Pulling the hem over the curve of her breasts, they gently drop from the fabric that once clung to their outline and give a slight bounce - my cock throbs, body tenses. As I have her shirt just pulled up to her elbows, I cross her arms to limit movement, holding them behind her head. My free hand slides up her waist and cups one of her impossibly delicate breasts in my palm. Tugging at one of her nipples, her hips give a slight buck, a soft sigh escapes her throat, followed by an amused laugh and a needy 'ohh'.

Kissing down her neck, I lick and caress, feel her body responding in little shudders. My face in her chest, rolling one pert nipple between my fingers and gently tugging at the other with my teeth, her thighs are pressed to my sides - and I desperately want to feel them wrapped around my head as I bury my tongue into her.

Hands traveling south, impatiently tugging at her waistband, she lifts her ass to let it glide over the gorgeous curve of her hips. Undies and all gone in one pull, her delicate scent sends my mind into overdrive.

I draw her face to mine and whisper -

"I want to drive you fully mad with pleasure," I tease a finger at the opening to her pussy, "I want you sitting on my face."

Scooping my arms under her thighs, I pull her up and have her on her feet. I turn so I can lay my head back on the seat of the chair and pull her down onto me. Immediately my tongue finds her clit and I press and lick against it like a man starved. I wrap an arm up around her waist and pull her tighter to me, I hear the first of many, many moans and go a bit more mad myself. Encouraging her to rock her hips, we soon find a rhythm.

I taste the honey of her pleasure and lap it up, I absolutely cannot get enough. I write the alphabet with my tongue on her throbbing little bud, having fun with it and spelling out dirty things I want to do next - it feels like her body gets the message. I plunge a finger into her tight, welcoming slit, encouraging her to give me more of what I want - more uncontrollable sounds from her lips, more instinctual grinding on my face - I feel her start to tense in waves and my passion is full tilt.

"Yes baby, please cum for me, cum all over my face, cum so hard it wrecks you," I manage to command between breaths and licks of that otherworldly delicious pussy of hers.

I think to call on oblivion to let this be my last ever memory. What more could I want?

...the answer is obvious.

She starts to shudder and I redouble my efforts, pushing a second finger inside and working a 'come hither' motion to coax her orgasm out as strongly as possible. I want her senseless when I'm through.

"Alex!!"

I hear her call my name and it absolutely sends me off a cliff - I need to be inside her, I need her to cum, I need every moment of this to stretch on forever.

Keeping my pace I let her rock onto me anyway she needs to get to that explosive moment of ecstasy - I don't have to wait long. I feel her thighs tremble and hear her begin to whimper in a way that jolts my core. I feel her tense on my fingers and cry out.

"Yes, yes Emma,' I encourage, "Come completely undone."

She collapses forward, catching herself on the chair back, heaving and trembling. I'm holding her to my face as she rides the little aftershocks, gently kissing and nuzzling, trying not to interfere with her winding down, but rather to entreat any other jolts remaining to crash over her still.

"Alex," she gasps.

I grab her arm and pull her down onto me, her ridiculously wet and warm pussy pressed atop my solid, aching cock, chests pressed together.

"I learned something just now."

"Do tell," she whisper pants, still working to steady herself.

"The sound of your voice calling out my name as you cum, kicks the absolute shit out of any music I've ever heard."

We laugh and she sinks further into me. Sighing out heavily, a clarity breaks through. We look at one another through fresh eyes, strange yet familiar, and begin to kiss deeply.

It doesn't take more than a moment before I feel her hips start to loll against me, and from this angle all it would take is a slight shift for us to -

Ohhhhhh, fuck. I slip inside her, ever so, and I can't believe how good it feels, just this little tease, barely the tip.

"Yes baby, take me inside you, press your hips into mine, fuuuuuuccckkkk," my head drops back onto the chair again.

"Alex, oh my god," her voice inflects up in a melodious way that makes my insides flutter.

I slip inside her, she rocks her hips onto me, and soon I'm to the hilt - and I cannot describe the feeling. Breathing heavily beside my ear, she takes my jaw in her hands and starts kissing my neck, pushing against me in a way that I feel her body's need.

Eyes closed, we continue rocking into one another, slowly, deeply. I press my fingers into that gorgeous pillowiness of her ass, pulling her harder onto me.

"Yes, Emma, ride my dick, it's all for you baby. Oh, fu-u-uck."

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