Taking A Risk

Author's note - This may be my last story in this series for a while unless anyone wants to comment a prompt... Enjoy!

Please note that this story contains the words 'pussy' and 'clit' being used for a transgender man. If this triggers you in any way, I wouldn't advise reading on.

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Work mixers -- is there anything worse? The small talk, the cheap alcohol, the fake smiles, and pretending that I actually like these people. I look over at Jason laughing with some co-workers at the other end of the room, his tie is loose but still it hangs around his neck. Okay, maybe there is someone I actually like, but pretending that we have no relationship isn't easy at the best of times but tonight it is a lot harder.

We had much better plans than this. It's our six-month anniversary weekend and he had booked us to stay in some cabin for a couple of nights out of the city. Then the big boss arranges this mandatory mixer, scuppering our plans rather unfairly. Jason told me that we could still go, just tomorrow in the morning but the long drive doesn't seem as worth it so we're going to have another weekend of sneaking around the city instead. I'm trying not to be disappointed, but I am. "Are you even listening to me Mikey?" Karen, one of my more irritating co-workers asks, and honestly, I had no idea she was even standing by me.

"What?" I gormlessly mumble at her making her frown. "Sorry. I'm not feeling great. I think I'm going to head home."

"Oh, okay." She frowns but this time with concern not from disgust that she wasn't being listened to. I almost feel bad for not listening to her in the first place. "Feel better soon." I nod and start to head out, fleetingly meeting Jason's gaze as I do.

I'm waiting by the elevator when I sense his presence behind me. I turn and produce a lopsided smile, trying to tell him that I'm fine and that none of this is his fault, but I can still see the worry written all over his face. He opens his mouth to say something, but he doesn't and instead, he's looking back at the closed door behind him where the mixer is going on and then he's stepping forward to wrap his fingers around my wrist.

The elevator pings as it arrives but he's already tugging me in a different direction, past where the mixer is happening and to the door at the end of the corridor to the main body of the office. In there are so many office cubicles but on the far side there are proper offices with doors, walls and some windows that thankfully have blinds. He leads me into his and closes the door behind us before his lips sweetly connect with mine. It's a short kiss, barely a peck, but it instantly boosts my mood. "I am sorry about this weekend, baby."

"Please don't stress about it, Jason. It isn't your fault."

Jason is shaking his head before I've even finished what I was saying. "But Mikey, I am stressed. You weren't the only one looking forward to this weekend you know." He then winks playfully, and it is like I may melt just by him looking at me. "This isn't how I imagined our six-month anniversary weekend would be."

"How did you imagine it?" I don't need to ask this question, I know the answer, but the answer is so gorgeously sexy that I must hear him talk about it again. Jason smirks at me.

This is risky. Six months of fucking and companionship and -- dare I say it -- love and we've managed to keep it completely under wraps. We've never once crossed a line at the office but with him stepping into my space so I can feel his hot breath and the hunger in his expression tells me that we are about to cross that line... but I don't even care.

A silence settles that it is so pumped with sexual tension that it's almost stifling. The blinds may be shut, and the door may be closed, but anyone could come in and interrupt us, which somehow makes it even more thrilling. My chest rises and falls heavily with anticipation, waiting for him to make his move, sensing my patience running out. If he doesn't do something soon then I may jump on him and wrap both my legs around his waist.

I drag my bottom lip between my teeth teasingly and this is all it takes, for his mouth to crash against mine eagerly as he backs me up against the wall. I can taste the cheap red wine on his tongue as it mingles with mine, with an energy that always surprises me especially after a long week and as a middle-aged fella. He has better stamina than me!

I subconsciously close the small gap between us, the buzz from our connection thrusting my hips forward so I brush against his pelvis. Jason moans from the friction into my mouth and his handle travels up to trace my jaw and grip the nape of my neck firmly. I don't think we could get even closer as we kiss, the flat of my stomach is even pressed against his body, but I need more. My core is throbbing with need.

His mouth leaves mine only so he can smatter kisses over my clothed collarbone as he starts to unbutton my maroon shirt. When I go to do the same to him, I have to pull the striped tie from around his neck first off before I have access to the buttons, my fingers work quickly but they are still slower than him, yet he pushes me away with a noise of mock disapproval. "Patience, Mikey." He brings his hands up to my sides which he strokes upwards until his thumbs can paw at my nipples.

"Fuck." I curse, feeling my back involuntarily arch.

"You like that huh?" He whispers devilishly. He knows I like that, he has played with my nipples many times and kissed my scars.

Jason breathes heavily and I can see the doubt flitter through his mind. He wants me right here, right now, but the risk is making itself known. "Jason." I whine, telling him I don't care anymore just by saying his name. Because of our closeness, every time he breathes his body rubs against mine making the flame roaring inside me increase with every breath. "Please."

"Anything for you, my good boy." He returns to me, and his lips are quickly on my neck, sucking lightly at the skin there. He sucks harder when he reaches just below my collarbone, knowing that a mark here would be easy to cover. I moan as he bruises me and then I moan even louder when he pops open the button of my pants. He moves quicker then. He pushes the shirt off my shoulders leaving my top half completely bare before he tugs down my pants -- I help him by kicking off my shoes and stepping out of the clothing, leaving me in nothing but my boxers.

Jason isn't at all shy when he cups me through the fabric of my boxers. He presses the pad of his finger against where I throb, and I hiss as I grip his arms to stop myself from falling to the floor. He hums, clearly satisfied by how he can detect my wetness through the fabric, before he slowly rubs me through it, adding additional pressure every time he passes over my aching clit. I'm about to criticise him for teasing me when he pushes my boxers down too leaving me completely naked apart from my socks.

He wordlessly kneels to the floor, trailing kisses as he goes until his lips are teasing the inside of my thighs currently delicately, but I know he can snap at any time. His hand returns to my wet center which he massages just like he was doing before, but this time without the fabric barrier. I am already coating his fingers with my juices, yet I believe we are only getting started.

I gasp when he finally penetrates me with a finger. It is agonizing how slowly and gently he moves it as he continues to tease me. I whimper, suddenly feeling quite impatient, and Jason looks up at me with a look that reads that he could tease me for the rest of the night, and I know he has it in him. "Shall I stop?" He asks.

"Keep going. Need... need more." Jason smiles up at me mischievously and curls the singular finger that he has buried inside me. I am ashamed of how loud this makes me moan.

"I can't hear you." He taunts.

"Please, Sir." I beg. "Please, I need more."

Another whine leaves me because Jason removes his finger from me and instead draws it into his mouth. He tastes me with a humming sound, making me weak at the knees. "Well, since you begged..." He mumbles and then before I can even take in a breath, he buries two fingers into my pussy with the other hand he was using to before taking me by surprise. My head falls forward into his chest, my gasps from him pumping his fingers in and out muffled by the fabric of his white shirt.

He expertly works me up. Curling his fingers in a way that has moans tumbling out of me, his thumb occasionally joining the party by rubbing against my tiny dick. The closeness of our bodies has me sweating. Here I am with my back firm against the wall of his office, completely naked, with my boyfriend's fingers deep inside me, not far from where the company mixer is happening with none of our co-workers aware that Jason, a respected co-worker, was about to fuck me hard. It's incredibly hot, and maybe when the heat dies down, we will both understand the true risk that was taken, but our need for each other at this moment trumps any rational thought.

Jason's fingers work into me at an increasing pace as his teeth nip at my thigh, trying to grab my attention. He has it, but only briefly because of the tightness building in the pit of my stomach, telling me that I'm near to my release. I moan loudly but this time my hand flies to my mouth in an attempt to quieten it, but the determination in my partner's eyes tells me that he wants to hear me before he requests it, as he continues his rough assault on my pussy. "I need to hear you my good boy. I always want to hear your noises. I want everyone to hear what a good boy my Mikey is being. So obedient."

"Fuck." I cuss, not quite believing that he doesn't care if we are heard. "I could cum just with your words." I breathily laugh between my moans.

"That sounds like a challenge." He's then quickly adding a third finger, stretching me out for him, keeping me pressed against the wall. "Taking me so well baby... Now you're going to cum when I tell you to. Like the good boy you are."

I clench around his fingers in reply as he somehow increases the speed of his strokes, and I feel like I'm about to completely crash over the edge. I want him to fuck me so hard, no, I need him to. I need him to do anything that would make me his. "I'm close." I whisper as my eyes roll back into my skull. So. Fucking. Close.

"That's it, Mikey." He murmurs, continuing his rough pace, when his thumb from his other hand brushes over my tiny dick momentarily. I'm so close to the edge it is almost painful, I know I'm going to cum hard. "Ready?" He warns but I don't have a chance to reply because the thumb on my clit starts to rub quickly, crashing me over that edge.

"Fuck!" I loudly curse and claw at the fabric of his shirt desperate to feel every inch of him. He pins me against the wall to stop me from collapsing as I convulse in his hold, my legs shaking vigorously because of the throws of my orgasm. My vision has gone white, and it is like I am reborn. The only thing that really grounds me is the feeling of his hardness against my thigh.

I am moaning and panting as he aids me through the shockwaves, drawing it out as long as he can to the point that I'm starting to get overstimulated. I'm already a mess but I know that this won't be it, he will have other plans to wreck me further.

He sucks his fingers clean as soon as he removes them from me, but he's quickly engulfing me in his arms when my knees turn weak. I am no longer being supported by the wall, but by his strong frame as he holds me close. Jason's breath is hot near my ear, and it takes a few seconds for me to find any kind of strength to meet his gaze. I thought perhaps there would be traces of concern there, but it is pure lust.

He's patient with me, waiting for me to make the next move as his Adam's apple bobs with some kind of expectation. I listen past our breathing briefly, just to check that there is no noise from outside, but it is quiet. So I brush my lips against his and feel how he smiles before he presses his much firmer against mine, but there's something so doting about how he makes sure I'm steady on my feet.

Deciding that I've recovered enough to continue, I resume unbuttoning his shirt, and this time he lets me. I take my sweet time and he edges closer, pushing his pelvis into my thigh. I'm not sure if this is a conscious or an unconscious act but it gets the fire started again within me.

I try to tease him. My fingers draw patterns on his chest which shines a little with sweat, I litter gentle kisses on any patch of skin I can find, and one of my hands grazes over the bulge in his pants. He groans and bucks his hips at this, showing that I'm not the only needy fella in this office right now.

But I try my luck too far. He loses his patience with frustration taking him over when I brush a thumb across his bottom lip. Jason growls and then without any hesitation I am being swept off my feet. A very unmanly yelp of surprise leaves me as he does, and he effortlessly tosses me over his shoulder like I weigh absolutely nothing. He roughly spanks my ass once making me whimper and then he's striding towards his desk with a very sexy intent. Not caring about the consequences, he sweeps everything off it with one arm and then he's placing me down in the gap he created.

Jason removes the shirt from his body before he's passionately kissing me again. He's standing between my legs, and I can feel his hardness on my boy pussy through the fabric of his pants. It feels impossibly big, but I know it fits quite nicely. The thought has me kissing him harder, opening my mouth wider to welcome his tongue. It is a kiss that is beautifully messy and dripping with impatience.

I'm breathing heavily when he steps back to admire me needy from his touch. He drags his eyeline up and down my body as he begins to unbuckle his belt. "You've been naughty." He states and yanks the belt free. "Where's my good boy gone?" Then he's pushing down his pants and underwear in one move, letting his red cock spring free. It looks painfully hard, and he gives himself a few subtle pumps in an attempt to relieve some of the pressure. "Fuck Mikey. If you could see what I could see right now, my favorite person spread out and wanting on my desk, then you wouldn't be able to resist risking it all either."

"I am risking it all too." I kindly remind him with a brief glance at the door. "But I love you so much that it doesn't feel like a risk." He chuckles at this in a way that is both warm and emotional, like he doesn't believe that I'm real.

Jason gets close to me again and kisses me sweetly which juxtaposes the dirty action of him rubbing his dick over my entrance. I have to break the kiss when he starts to push inside with a gasp, my eyes screwed shut as I feel him deliver every inch to me slowly yet with an urgency. I arch off the desk, but he keeps me grounded by wrapping an arm around me. My head tilts back with bliss and he buries his head into my shoulder where he breathes heavily against the bare skin of my neck.

I feel so complete with him fully seated inside me and his groan from the heat of my pussy makes me tingle. All we do is breathe heavily for a few seconds as he lets me adjust to his size. Trying to compose himself, he swallows before he guides me to settle my back on the surface of his desk. His strong hands are then pressing into my thighs as he pushes them apart gently to give himself some room. A whimper leaves my lips as soon as he starts to move.

His movements may be slow initially, but I still feel him hit deep inside. I love how he still manages to stretch me out after all this time, and I'm addicted to the feeling. I claw at the edge of the desk, needy and wanting, and Jason grunts, clearly trying to remain restrained when in reality all he wants to do is animalistically fuck me so hard to make me his.

I bite my bottom lip again which flips his switch. He speeds up with his balls slapping at my skin. A gasp escapes me thanks to his rapidly increasing pace, and I have to bite down on my lip to keep myself from screaming out his name. My hands tangle in his hair, and I pull at the locks there in the way he likes. He grips at my hips in response, and pulls me towards him even further, making him hit depths I don't think I've ever felt before.

The motion rips a moan from my throat as mutterings of praises and moans of his name leave me with every snap of his hips. The intensity of his strokes is so strong that it is like I could become bruised from them. I can feel him twitch inside me as he chases his climax whilst I'm still in the process of coming down from my first. It is overstimulating. A mixture of pain and pleasure with me wanting him to stop but needing him to keep going.

Jason moans as he bends over me creating a new angle that has him pressing more against my G spot than before. I hook my arms around his shoulders to keep my convulsing body steady. He feels as I get closer to my release when I begin to clench around him with my breathing turning shallow. He anchors himself by wrapping his strong arms around my back, making it easier for him to slam roughly into me. His dick is soaked with my juices and the noises that this makes are obscene. "Jason I..." I lose the ability to say anything else, my head is foggy the more the coil winds in my gut.

He leans forward to kiss me almost out of support and then with one arm still firm behind my back, his opposite hand sneaks between our bodies so he can find my stiff tiny dick. His fingers begin to play with it and I'm close to jolting off the desk completely. A sound that is a mix between a whine and a moan is muffled by his mouth and I'm bucking against his touch for everything he has. "You're being such a good boy for me, Mikey." He murmurs against my lips. "I'm nearly there, just hold on for me baby."

I find it impossible to reply coherently but Jason seems to understand my agreement from my senseless babble. He slaps into me fiercely, faster than I think he has ever fucked me before. The desk shakes loudly with every movement, but I don't have time to think about how sturdy it is because Jason starts to groan more frequently and the dazed expression on his open-mouthed face tells me he is there.

I wrap my legs tightly around his waist as his ministrations on my clit quicken. "I-I can't hold on much longer." I warn as I sense the tension inside me about to snap.

"Come on then baby boy. Cum for me." The instruction has hardly left his mouth when my vision turns white along with my release.

I moan loudly, almost a scream, as I completely unwind on his cock. The shockwaves make my legs cramp inwards, shoving Jason even further into me. He groans at the action, with his hot, sticky cum coating the walls of my boy pussy. His pulsating dick is hilted right inside of me, pouring out his seed with a sort of primal instinct to breed me. The sounds of his moans are so sexy, I have thought that ever since our first night together, but I've noticed how they've changed. How they're more personal almost than before. He lets me hear every noise he makes, not just the super masculine macho ones showing a kind of trust.

I hold him close with my head buried in his hairy chest as we both continue to ride the waves of our orgasms. Neither of us says a word as we let ourselves come down, feeling the final twitches of our organs. Jason is the first to pull back. He doesn't pull out immediately but looks down at the sight of him buried inside of me. He smiles to himself and squeezes my waist as he does pull out carefully, letting his seed drip out of me and down my thighs, making quite the mess of both the floor and his workspace. "We made a mess." I finally manage to mutter, and he chuckles warmly.

"Don't worry about that. I've got it." And I believe him because he always seems to have a hold of everything. Maybe, subconsciously, it is one of the things that drew me to him. "You just sit there and look sexy and, well, thoroughly fucked." He cups my cheek as he says this with true adoration in his brown eyes. "You know the journey to the cabin is only three hours. We could be there around midnight."