Sex Stories

Sex Story: Office Affairs – Old Enough To Do It, But Young Enough Not To Know Better

sex story office affairs cassie
Written by Charlie Greene

“I call bullshit!” I said, grinning. “That’s not even POSSIBLE!”

Sarah laughed lightly and it was obvious from her over the top tone in her voice, she was being dead serious. “I’m serious! I was standing underneath the ladder – for support. He walked up to the top… and it ALL hung out.”

This was why my best friend Sarah and I were inseparable. She was this shy, introverted girl – I was this bold, no-holds gal. We balanced each other out. “What do you mean it ‘all hung out’?” I pried. I couldn’t help it, I just had to know details.

“Cassie, it was the biggest thing I’ve ever seen… I’m not even kidding.”  My eyes grew wide at the comment; it wasn’t like Sarah to just exaggerate – especially about this kind of topic.

Mike had just started working for our company a few weeks ago. He seemed friendly enough but very quiet. He was incredibly good looking, although a little older than what I was used to – my last boyfriend was only 18; but there was something about him, I just had to have.

“How big was it?” I asked, trying to get the mental image from my mind. “Like really, how big could it possibly be?” I watched Sarah turn bright red, the same shade as her shirt. She must have like him.

“Cassie, it stopped maybe an inch above his shorts.” Her grin told me that she really liked him, but unfortunately – so did I. I knew at that exact moment, I just had to get Mike to take my virginity.

* * *

We walked back into the office after our break, both grinning ear to ear. Mike was busy on the ladder again, working on some electrical panel in the ceiling. I casually walked underneath – to see if there was any truth to what Sarah had told me.

As I approached the ladder, I realized that Sarah was not only telling me the truth, she was down-playing the sheer size of it – a lot. Trying my best not to look obvious, I glanced up the shorts again, trying to assess just how good it must feel being inside someone… being inside me. My body quivered at the thought.

“Can I help you?” A husky voice asked, making me jump more than I would have liked. Coming back to reality, I became aware that the husky voice, was Mikes – looking down at me, from the ladder.

“Oh, I … uh… sorry” Shit. That’s all I could mutter? That was my game plan? I frowned outwardly, obviously disappointed, and started to walk away. “Wait!” Came the voice, as I stopped and turned on my heel. My head already spinning, I lost track of my balance and was sent spilling over the desk. I landed on the ground with my shoes hooked over the chair leg. I was stuck.

“Here, let me help you.” Mike called. He quickly ran around the cubicle, pausing a moment to assess the situation. I blushed slightly at the sight of him, thoughts of his huge dick pounding me at that very moment. I looked up at him helplessly, trying to figure out what was taking so long. I saw him staring down at my shoes? No, not my shoes – my ass, hanging out for the entire office to see. He gazed intently obviously enjoying the show. After all, it’s not every day you see a girl sprawled out across the floor with her heels hooked into the chair.

Gently, he unhooked my shoe from the chair and wrapped his huge muscular arms around my waist, helping me to my feet. As I stood, he pulled me in closer, when I could feel his hardening dick, pressed firmly against my belly button. Sarah was right, this thing is huge.

“Let me help you get some ice,” he said, leading me to the back kitchen. I wasn’t hurt, but I wasn’t going to tell him that. Slowly I walked, my arm securely around the backside of him – skimming over his firmly sculpted ass while we walked.

“I’m okay, “ I started, as we reached the kitchen door. My hand casually moved back toward his ass, skimming past his short hem, tickling the small of his back. “I’m just clumsy, that’s all.”

Mike frowned a little, as I moved casually away from him. I pulled my shirt down again, revealing far too much cleavage – perfect, I thought. “How are you okay? I saw you got stuck on the chair, seemed a little intense.”

I smiled coyly, remembering his intense stare. “I got a little flustered. But, maybe you should check out my ankle…” I paused, “you know, to make sure there’s no damage. I quickly took the opportunity to jump on top of the table, trying to ignore the already wet mess aching between my legs.

* * *

Mike was much older than I was used to – and it showed in the way he gently caressed my ankle, looking for an injury that didn’t exist. He paused for a moment, obviously looking intently at further up, trying not to get caught.

“Do you like it?” I asked, casually spreading my legs a little further for him in the process. The question made him blush. “I’m not sure I know what you mean, but your ankle looks fine.” He started, standing up, never breaking eye contact with my tightly covered pussy. I knew he could see my light pink lace panties. I spread my legs a little bit further, gently moving my skirt up a little bit higher on my thigh. His eyes followed my hands, expectantly.

Slowly, patiently, I traced my fingers up farther, intently watching Mike’s face. He licked his lips staring at my wet lips. Bringing my fingers farther up still, I noticed the bulge getting even bigger through his shorts. The thought of his huge dick, pounding my tight pussy made me quiver – closer to my panties my fingers went.

I waited until his eyes were staring constantly, licking his lips as my fingers traced outside of the thin material. My smooth pussy was aching to be touched; and Mike was eager to watch. I quickly moved the thin material to the side, bringing my ankles on to the table. Spreading my legs a little further, he smiled slightly – he liked what he saw. I glanced down, watching intently at my glistening pussy, it was swollen and starting to puddle underneath me. The thought made me grown, despite trying to remain calm.

“Do you like what you see, Mike?” I purred, bringing my legs up a little further still. I watched in amusement as he shifted his position, not entirely comfortable with what he was watching, unable to look away.

“How, uhm… how old are you sweetie?” He asked, after catching his breath. He was panting. I tried not to imagine how incredible his mouth would feel on my wet, dripping pussy.

“Old enough to do it, young enough not to know better…” I answered my voice just above a whisper. He frowned a moment, considering what I just told him. “Okay, but there are certain situations that can result in my going to jail…” his eyes I noticed never left mine.

“Mike, I’m legal… I promise. I turned 18 two weeks ago.” I began getting flushed – this was not how it was supposed to turn out. He was supposed to get excited, ravish me. He was supposed to fuck me hard with that monster cock of his.

“You’re 18?” He asked, stepping toward me cautiously. “Yes,” I answered. “I am perfectly legal to make bad decisions. So why are you still standing there?”

Mike quickly walked toward the door to the kitchen and propped it open a little, after checking to ensure no one was coming, he quickly ran back towards the table. His eyes shifted back to mine – he bit his lip.

“Mike, come here” I called, slowly moving my hands away from my underwear, moving carelessly up to my chest. Slowly, I left my blouse over top of my head, revealing my perky, size c tits. My nipples are hard from anticipation, they ache for his touch. They’re desperately trying to be touched, poking through the thin lace covering with anticipation. I see him consider me for a moment and then walk toward me. His erection is harder than ever, but he’s no longer trying to hide it. I stare intently at it, watching it, imagining it.

Finally, he’s pressed between my legs, his face is inches away from mine – studying me. “You know, I could probably be your dad.” I smile a moment and reach down firmly grabbing his massive cock. “But you’re not my daddy… yet.” I look up at him, his eyes wide in wonder. His hand skims over my leg, sliding up further and further, until it’s directly over my swollen pussy. He gently caresses it with his thumb, skimming his fingers over top of my lips, enjoying the wetness as it drips over his thumb.

I moan as he gently caresses my clit, slowly stroking it with his callused fingers. I’m ready to burst at the seams. I gasp for air, unable to find words. He mouth slowly lowers over top of my lace bra – his mouth gently kissing the silky fabric. His breath is hot as I try to focus on how good his dick is going to feel inside me. I’m trying to control my urges and enjoy this moment.

He slowly flicks his tongue against my nipple over top of the soft fabric, which sends chills down my spine – it’s hard to function when my body is sent into over drive. I manage to grab his rock-hard cock and squeeze it with ever ripple he sends through my body. “Cassie…” he hisses, trying not to let the urge to devour me take over. “I want to feel inside you”. I try to regain composure as his tongue skims underneath my bra, over my now swollen nipples. They’re puffy and engorged, waiting to be devoured. I know he’s ready too.

“I need you to lick my pussy Mike,” I purr, trying to find my voice. I can’t control it any more. I need to feel him. My pussy aches for him. He quickly obliges, bending down and pulling my ass toward the edge off the table. I lay back and moan as I feel his mouth devour me. His tongue circles against my lips, parting them softly. He growls as he continues to lick my tight sex, drinking every last drip as he pushes me over the edge.

I reach for my tits, feeling the waves overcoming me. I pull my bra down, exposing my swollen tits, playing with the nipples that eagerly wait for his mouth. The feeling is incredible; wave after wave, circle after circle – my body convulses as I try to contain my moans.  I can tell he’s ready to explode, as he moves back up to my tits, pressing his monster cock against my swollen clit. I moan again, trying to imagine him thrusting inside me.

“I want you to fuck me Mike, I want you to own me… as hard as you can” I say, my hands reaching for his thick hard cock. He smiles a moment as he undoes his shorts. “I want you to show me how to get fucked.” He pauses for a second, reaching into his boxers.

“What do you mean show you how?” He asks, his voice wavering.

“I’m a little inexperienced…” I say, my pussy aching for the monster he’s holding in his hand under his shorts. I can see the size of it, pressing against his boxers – my body quivers in anticipation. Mike stops for a moment, trying to understand what I just confessed. “Wait, Cassie – you’ve never … you’ve never fucked anyone?” He sounds a little apprehensive.

“No,” I start, my eyes focused on his massive dick. “But I want you to show me how.” I sit up on the table and reach at his boxers, his eyes widening as I do. “I can’t do this Cassie… It’s not right.” I frown a little and decide to persuade him. I firmly grab the thick shaft inside his shorts, moaning.

“My God Mike, it’s huge!” I smile and slowly bring my mouth to the tip of it. I gently lick the tip, bringing my mouth over the swollen head. I flick my tongue over top of the head, and playfully bite the tip. His breath catches and he sighs. I grab it with both hands, pushing it into my mouth, inch by inch. I nearly gag at the end, realizing the sheer size is almost too much for my mouth to handle. I pull back a little and look up at Mike, who’s staring intently at me.

“Keep going baby, that’s really good.” He purrs, pushing my head back on his huge shaft. He places his hands on the back of my head, grabbing my hair tightly. I moan in appreciation, eager to please him – my pussy aching once again for him. Deeper and deeper I thrust, taking him all into my mouth – rubbing my tits against the sides of his shaft. He moans even louder.

As he’s getting ready to cum, I quickly stop, making him wait. He looks down angrily. “Why are you stopping?” He demands. I grab his shaft in between my hands and lure him towards my swollen, dripping lips. “I want you to fuck me…” I cry out, sounding far too eager.

I continue to move his dick – using the tip of it to play with my clit. I can feel myself dripping again, and I won’t be able to control it anymore. Mike lets out this deep groan as my clit swells up more and more, his head dripping with pre-cum.

“Fuck me baby… Please?” I say, firmly pushing his hard shaft at my tight, swollen hole. The head feels tight against my virgin hole, but it feels incredible – I need him. I want him.

With a deep moan, he pulls my ass towards him, nearly off the table. My head hits the table hard, but I don’t notice. I’m too excited to notice. He firmly grabs my hips and tries to steady himself. I help him along, using my hand to push his thick cock inside. I moan as I feel him stretch me out. I look down and groan – he’s only a quarter in. Further he pushes inside me. I feel my tight pussy stretching, aching to take him all in.

Finally, grabs my hips and decides to push his dick further into me. He tries to be gentle, but can’t help but moan in the process, “Jesus Cassie, you’re so fucking tight. I can’t” he starts “—you can,” I finish, he’s NOT going to stop now. I grab his face and guide him towards my tits, which are desperately aching for attention. He bites my nipple and flicks it with his tongue. My body quakes at the feeling.

Another thrust. I feel him stretching me out – past the point of any man. Past the point of any toy. He hits a spot that sends a warm feeling through me, my pussy clinging to him like a glove. He pulls out, biting my nipple.

He quickly grabs my shoulders, holding me in place. My pussy is so wet, it’s ready to explode. Mike thrusts again and again. I feel my body getting close to exploding again. “Harder baby, fuck me harder” I beg. Mike starts going even harder than before, nearly thrusting me right off the table in the process. He grabs my ass and pulls me back toward him. Rubbing my ass as he thrusts faster.

His finger continues trying to press into my ass hole, tightening my pussy against his hard cock even more. Farther and farther he pushes his finger inside – my body shivers and I convulse.

“Mike, oh my God… I’m going to cum!” I start, and my body arches against the table. I shake uncontrollably, moaning and panting as he continues to fuck me harder. My cum has made me a little looser now, but still – he’s pushing as hard as he can.

“Fuck!” He shouts, as his body starts shaking. I can feel his thick vein pulsing inside of me – better than any sex toy I’ve ever used. He slowly removes his cock from inside me and stares at my stretched pussy. “That was the best thing I’ve ever done.” He reaches for my clit again and starts gently rubbing it again. My body starts responding again, sending me into over drive.

* * *

We both hear the door open at the same time, completely frozen. For a brief moment, I had forgotten we were still at work, naked on the kitchen table. I freeze completely, staring down at my naked chest and pink pussy – now dripping his sweet juice on the table.

“What’s going on here?” A deep voice says. I can’t recall the voice, but I’ve heard it before. Mike laughs slightly and walks toward the voice, his dick still hard from fucking me. I freeze, not sure what to do.

“Well, I had to check her injury Chuck” Mike starts, pointing at my ankle on the table. I recall the name Chuck quickly through my mind and lift my head up to see who has walked in the door. Facing me are both Mike and Chuck, both staring at my pussy with extreme interest. I smile meekly. Chuck is Mike’s supervisor, and dear friend. With a killer body and deep husky voice, Chuck is just as attractive as Mike, although he’s probably not as well endowed.

The two start talking for a minute, but I can’t hear them. I think about pulling up my panties, but I’m afraid to move – we were caught. While they continue to talk a dark thought crosses my mind. I imagine the two of them slowly fucking me at the same time, and my pussy starts to pulse for the third time in ten minutes.

Without thinking I reach down and begin rubbing my pussy at the thought. I can feel my body start to warm up in thought of the two of them pounding my body – fucking me at the same time, the same way as before.

I notice that the talking as stopped and slowly look up at the two men standing by the door. Mike simply smiles, while Chuck tries to avert his eyes. He had been watching the whole time, but I caught him – he’s embarrassed.

“Do you like what you see, Chuck?” I ask, sitting up completely. I never take my fingers off my pussy, still spreading my legs open so he can see the flushed pink pussy glistening against the table.

“I… I do… But this is inappropriate…” Chuck started, glancing at Mike. Mike once again had his dick in his hands, rubbing it smoothly.

“Chuck,” I purred. “Come here for a minute.”

He quickly responds by moving quickly toward me. I can see the outline of his hardening cock inside his pants. My breath quickens slightly, licking my lips. He stands near my pussy, his hands shaking slightly at the sight.

“Chuck,” I say slowly. “I think you need to feel this” I say, grabbing his hand and placing it against my tight pink pussy. He moans a little, staring at my swollen, tight nipples. “I want you to lick them Chuck.” I demand. He lowers his head and places his mouth over top of my nipples, sending ripples of pleasure through my body. I can’t help but moan. My head goes back again, trying to contain my excitement.

I glance over at Mike who was hard again, stroking his cock – watching me please his boss. Watching me please his friend. I grab Chucks cock through his pants, panting as he continues to suck my swollen nipples – feeling an intense need to fuck both of them at the same time.

“Mike,” I start, slowly waving him over. “I need you both to help me.” Chuck stares down at my hand, now gripping his hard cock intently. He lets out an intense moan as I squeeze his thick shaft with my hand.

Slowly, I watch Mike walk over to us, his hand rubbing his dick until it’s hard and thick again. I moan at the sight, remember how good it had felt inside of me. Needing to feel him inside of me again.

Mike slowly pushes Chucks hand toward my pussy, using his fingers to thrust deep inside while Chuck focusses on my swollen clit. I can see my juices dripping over both of their hands.

I squeeze Chuck’s dick tightly in my hand, working to undo his button. “I need you both to fuck me Chuck. I want to feel you both… okay?” I purr, pulling his thick, hard shaft out of his pants and into my mouth. I suck it hard, like I can’t survive without it – thrusting as deep as I can into my throat. Chuck moans out and clutches the table.

Mike continues to work intently on my pussy, rubbing my clit over and over in a circle until it’s pulsing in anticipation. I continue to suck on Chuck’s dick until the veins are pulsing. I turn to face Mike, grabbing his cock firmly. Slowly, I push it into my pussy –holding him for balance. When I get my balance, I grab Chucks cock and slowly push it into my ass.

“It’s so tight,” Chuck says, trying to push it in a little harder. I stand facing Mike and bend my ass toward Chuck, who thrusts his dick into my ass as fast as he possibly can. He bites my back shoulder as ecstasy takes over his body. I let out a moan so intense that I hardly recognize it myself.

Mike watches my body, continuing to rub my clit – with the head of his dick inside of me. My body starts shaking in pure joy. Excited and aroused. Chuck starts moving his cock out of my ass slowly, ramming it back in quickly. Hard. Fast. My pussy becomes so wet, it’s practically dripping on the floor.

“Fuck me Mike,” I purr, holding him for balance. He looks intently at me, thrusting his hard cock inside my tight pussy; now even tighter than before because of Chuck. I moan out so loud I can hardly contain myself. Thrusting harder and harder, I scream in bliss, my pussy pulses and convulses. I feel my body start gushing as it pulses through everything inside of me. I let myself enjoy the intense orgasm – feeling the two thick cocks pushing up inside of me from every angle. As much as I try to relax, it’s nearly impossible, with every thrust sending me into an orgasm again and again.

I start to feel Mike’s hard dick begin to throb, as he lets out a stifled moan for the second time. He continues to thrust, his body shaking in pure pleasure. It doesn’t take Mike long to catch up with me in pure ecstasy – grabbing my nipples and rubbing them as he begins pumping me full of his thick, sticky liquid. I moan as I feel him cum – my body slowly filling with his silky juice. I purr out even more as I feel his liquid begin to drip down my leg, mixing with my own sweet juice.  Chuck sees Mike playing with my tits and decides to send me for one final ride. Slowly he moves his hands around to the front of my body, grabbing my swollen clit between his thumb and fingers. Rubbing it gently up and down, my body continues to rebuild again. I feel my pussy start to moisten and ache. Chuck continues to pound into my ass, his thick cock reaching higher than ever before.

Soon, my body is convulsing again, as I lean against Mike for support. Chuck grabs my ass and starts to shake and without hesitation, he shoots my ass full of milky cum,  panting in excitement.

As Chuck finishes, I grab his balls tightly. He lets out a loud yelp, taken by surprise and thrusts even harder. I can’t contain my moaning, it feels even better now that he’s thrusting harder. Especially now that there is a lot of milky cum inside me. He eventually stops and slowly pulls his pulsing dick out of my ass, squeezing any remaining cum onto my ass – which is sore from the constant squeezing and pumping. My clit pulses happily at being well-used for the first time in a long time. This was definitely better than any toy I’ve ever used – I couldn’t have picked a better first time.

I smile as I watch the two men high-five and talk about how incredible that was. I can’t help but laugh when I hear Chuck talking about my tight ass – how he loves my pussy too, but that ass is incredible.

“Your ass is out of this world Cassie, I’m going to hit that again real soon, okay?” Chuck says, staring at my naked, dripping ass. I smile back at him, “you had better hit it again soon – I’m horny all the time.” He smiles coyly at me, without missing a beat. We had definitely just started something really good here on the kitchen table – something that no one would ever know about, except the three of us.

I move my panties back over top of my sore, swollen pussy – now dripping with both of their semen. I hesitate slightly as I feel the slick liquid dripping through my underwear, it feels warm and thick. I move my fingers down quickly and taste some of the saltiness that is pulsing through me. My cunt aches for them; I need to have more of them.

I slowly stand back up and fix my shirt, I look down at my tits, they’re still hard and swollen – turned on is beyond an understatement. I look over at the two sexy men and smile. Mike is definitely bigger, but Chuck is amazing to take in the ass.

For the first time, I realize that I might not have to worry about my job for a long time – after all, I know that if Chuck has his doubts, Chuck and Mike will be able to discuss matters further. I looked up quickly at Mike who was now smiling at Chuck, “hey boys, does this mean that I can have a few more injuries this month?” I snort, “because I feel like our kitchen needs a first aid room to assess all of my injuries further. Mike and Chuck laughed, looking at my body knowingly.

And I began to find a way to tell my best friend, that Mike did, in fact, have a monster cock – without admitting that I fucked my boss too.

About the author

Charlie Greene

Our sex expert, Charlie, is a long-time professional in the adult industry, specialized in screenplays for several major production houses. She is direct, have zero tolerance for weak and insecure men, loves to get in bed with another woman from time to time, and consider herself borderline nymphomaniac. Enjoys writing explicit sex stories that are mostly based on her own experiences. A loud advocate of sex toys and sexual liberties. Enjoys kink sex and admits to having one particular fetish that makes men addicted to her.

"Every time I lie on my bed to write a new script or a sex story, I get all wet. If there's no man around at that moment, can guess how it ends."