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Playing with the boss
Posted:Nov 10, 2021 1:15 pm
Last Updated:Nov 11, 2021 9:26 am

I have been in lust with my boss Gary from day one. I am even his work wife. Will sneaking into a party he is attending help convince him I want to him by day and by night?

What would you say a -day weekend? Gary asked, and I could have rung his beautiful neck even suggesting such a thing.

Why? I asked, turning from the filing cabinet in his private office face him. I had been digging something I hadnt actually needed, which I did about five times a day simply have an excuse go into Garys office.

Why? You dont say Why? when your boss offers you a -day weekend. You say, Hell yes, boss. idea Ive ever heard.

I pursed my lips at him. Why? I asked again.

You and I both worked weekend last weekend, Gary said, leaning back in his vintage leather swivel chair. He put his hands behind his head and raised his eyebrows, waiting contradict him. I envied the hands on his hair. Gary was a silver fox, and didnt seem mind at that he was mid-forties and already mostly gray.

No big deal. I waved my hand and sat in the club chair across from his desk. When I crossed my legs, I watched him, hoping hed look at my legs. He did for a split second before meeting my eyes again. Its not like I didnt do overtime. And its not like I hadnt loved every second of it. Weekend work meant Gary out of a suit and in jeans and his favorite ratty concert T-shirts. Saturday had been Pink Floyd. Sunday belonged Eminem.

Gary leaned forward, rested his elbows on his desk and looked me in the eyes. Brown eyes, bright but tired.

Katie broke with , he said.

What? Why? Breaking with Gary seemed as insane as setting a Rembrandt fire. Who did that?

This is awkward. Gary wrinkled his face , and it was as handsome wincing as it was smiling.

Me? I asked.

She said I spent more time with my assistant than I do with her.

You do.

If you werent, you know, you, it wouldnt be a problem. But you are you and thats a problem. For her, not me.

Did you just tell me Im pretty?

Gary glared at me. You know you are. Katie wouldnt care about that if I didnt spend my weeks with you and my weekends with you. She says you are my work wife.

So why the -day weekend? You trying get rid of ? I asked.

Never, he said vehemently, and I cherished that vehemence. Jacks taking me out tomorrow a recovery day of hiking and drinking. Then hes forcing me entirely against my will go a party at a friends house Saturday night. And if Im not here, theres no reason you be here.

-day weekend it is then. I stood and smoothed my skirt down. œAnd thank you. I got invited a party too this weekend, I said, a lie. It wasnt a party so much as brunch with my sister. Maybe its the same party as yours.

Gary stood and walked around his desk. Gently he lifted the gold Star of David pendant I wore a necklace. His fingers were so light my skin I felt goosebumps over my arms. And Gary stood so close I could smell his light cologne.

No offense, but I dont think you go to the same parties Jack and I go to. Although if you want to come with us, you can. Beautiful women are always welcome at that house. He said it like a dare, like a challenge.

Is it one of those parties? I asked as Gary played with the -corners of the star. We are as comfortable with each other as people who worked in close quarters had be. I had smacked his hand when he reached for my food. Hed let sleep his shoulder when we took red-eye flights to London. But this moment felt different, felt personal.

One of those parties, yeah. He looked a embarrassed and I adored him it. Hed been careful keep his personal life separate from his professional life, even with me. But one Sunday afternoon Id had run his apartment reasons entirely work-related, and while hed been on the phone in the other room, Id glanced through a half-open door and seen Garys bedroom. A leather flogger sat on the pillow and handcuffs dangled from the headboard. When Gary had caught me looking hed blushed and stammered an apology. Id told him I didnt care as long as what he was doing in his free time was consensual. It had been the first thing Id thought of to say and only later had I realised it made me sound boring, virginal and utterly vanilla. What Id wanted to say was, The handcuffs? The flogger? Gary, thats nothing to apologise . Its sexy as hell, and I volunteer as your next victim. There hadnt been a night since I hadnt fallen asleep dreaming of his body, that bed, and those handcuffs on my wrists while I made myself come.

I wrapped my hand around his fingers holding my pendant.


Gary let the pendant go like it had burned him.

You work me, he said.

I know. I know. I raised my hands in surrender.

I knew. I knew. We had had this discussion once before on a night flight when neither of
us could sleep but seemingly the rest of the plane could. Hed admitted his attraction me, and me him, and the only thing that had stopped us from joining the mile-high club had been Garys innate sense of decency that kept him from sleeping with an employee two years his elder. I knew if i made the first move it would happen. But I just couldnt bring myself to do it.

Gary took a step back. I stopped myself from taking a step forward. Have a good -day weekend. ll see you Monday.

I smiled. œMonday.

Then I took my file, walked out of his office, and sat at my desk. I didnt trust myself to walk back into Garys office without declaring my lust for him, so instead I opened our messenger app and typed, Need car the party? Where? When?

Gary wrote back thirty seconds later. Yes, please. Saturday, . 2 Riverside Drive. Warn the driver we will ll be dressed weird.

How weird? I typed back.

Eyes Wide Shut weird.

I will make a note in the comment field.

And thats when it . I knew where the party was. I knew when it was. I knew I could go it if I wanted go it.

I wanted go it.

Gary had said Eyes Wide Shut weird and implied hed be dressed in some sort of costume. That would make it much easier slip in and out. I didnt want do anything but see him, and be part of his world a while. I wouldnt even talk him. But pass unobserved Id have dress the part myself. Saturday morning i made an appointment with my hairdresser who did my hair in a complicated and un-me updo. I bought a slinky white dress and a white masquerade mask. Gary had never seen me wear my hair like this. Hed never seen me wear white. And with the mask covering half my face, hed have no idea it was me. Since it was one of those parties, I also invested in a pair of white seamed stockings and a garter belt and white high heels with white ribbons that tied at the ankle. Once dressed I looked the opposite of my usual work self. My own mother wouldnt recognise me.

When oclock rolled around, I grabbed a cab. my way there I told myself that if the party wasnt my scene, I had do was turn around and leave. I could do this. Get in, get out, dont cause trouble. Dont reveal myself and whatever I did, no contact with Gary. None.

The cab dropped off. It took a couple seconds to work up the courage to step out and climb the stairs of the black-and-white -story townhouse. Through the door I could hear the sounds of music and laughter and the usual party revelry going inside. Before I knocked I tried the knob and found the door unlocked. As quickly and quietly as I could, I stepped inside.


, no.

Gary hadnt been exaggerating. It really was one of those kinds of parties.

Everywhere I looked I saw couples coupling. Kissing in doorways, draped over each other on sofas and in the room the left, some sort of sitting room, I saw a woman kneeling her hands and knees a coffee table while a man in a dark -piece suit and devil horns fucked her from behind. They werent alone in the room, not at . People stood around watching, cheering. Someone even held a stopwatch in his hand. Cash was scattered on the table around the womans hands and knees. From what I could tell it was a contest and The Devil was contestant number two. The previous contestant had fucked the woman twelve minutes and sixteen seconds before coming. The current contestant just fucked his way past the ten minute mark. Someone in the crowd said they were neck in neck. Someone else said they were cock in cock.

I stared, mesmerised by the scene. It was porn, beautiful, , playful live porn”and I couldnt look away. My nipples tightened under my low-cut dress and my pussy swelled at the sight of the woman taking the cock so casually in a room of a dozen people. I flushed and felt myself growing wet, and my vagina clenched at nothing, wanting something inside it.

Want play? came an accented voice from behind me. I turned and saw the man whod spoken. He wore a military-style long coat, white shirt open at the collar, plus breeches and Hessian boots polished a high shine. He was impossibly handsome, with shoulder-length, dark, wavy hair and a wolfish gleam in his dark eyes.

I no. Just watching, I said.

I shouldnt play anyway, he said with a dramatic sigh. I always win. Hardly fair, is it? He lifted my hand his lips at if kiss the back of it. Instead he flipped my hand over and pressed his lips the center of my palm. With a wink he walked away, no doubt seeking out more amenable prey.

I turned leave and came face bare chest with a man wearing nothing but leather pants. Nothing. Not even shoes. He had shaggy hair, brown skin and a wicked smile. I felt a sudden pang of attraction him.

, sorry, I said.

You must be new, he said, narrowing his eyes at .

Im new. , new.

We like newbies around here. He cupped my chin. Tell what you want, and I will l make sure you get it.

I opened my mouth, closed it, then saw Gary striding down the hallway toward the front door. He wasnt dressed nearly as oddly as everyone else at the party. He had on black trousers, a black vest, and a white shirt with the cuffs rolled to his elbows. His only nod to the party atmosphere was the black mask he wore over his eyes. Impossible not to know it was him, however. Not with that smile and that salt-and-pepper hair.

Him, I whispered. I want him.

You sure about that? the man in the leather pants asked. I couldnt believe Id spoken my wish aloud.

I am.

Then he kiss .

I kissed the stranger and found his mouth warm and his lips skillful. Id been so busy with work Gary I hadnt gone on a date in months. Whoever this man was, I didnt know, but I also didnt care. He had big hands that felt good on my waist, and a needed kissing sometimes. Even by a stranger.

And then I was off my feet. Entirely, completely and totally off my feet, being carried over the mans shoulder.

my God, I said, and the man heard .

Im a firefighter in real life, he said, slapping the ass. œTrust , I know what Im doing.

Glad one of us does.

Come on, man, he said as he carried me into a room. I caught something you.

Aw, you shouldnt have, Jack. I recognised Garys voice.

Youve had a hard week. Youve earned some fun.

So this was Jack, Garys kinky friend who dragged him parties? Is this something they did together? Share women? I wanted to be jealous if it was, but instead I found the prospect arousing, the thought of being passed back and forth between them.

I gripped the sofa cushion hard and tried to get my bearings. I was in a room, a nice but room with antique furniture like out of Pride and Prejudice something. Door closed. No lights on but the fire burning in the fireplace. No bed. Fireplace with an orn dark-wood mantel and a low fire burning. Other than the couch I and Jack sat , there was one armchair across from them and a huge steamer trunk that acted as a coffee table. Gary sat in the chair and held his wine glass lightly between his fingertips. He was watching me.

This is how it works, Jack was saying as he slowly eased my panties down my legs. Since you are new I do whatever I want do you and you say Red when and if you want me stop. And what I want to do to you is you while my friend watches. Then he will do whatever he wants do you. He wont be nearly as gentle with you as I will. Yes? No? Red?

I glanced at Gary, who grinned at Jacks warning.

I was scared, my heart pounding, my blood pumping so hard in my ears it sounded like the roar of an ocean.


I whispered the word so Gary couldnt recognise my voice. But Jack heard.

Good answer, he said, and casually unzipped his pants pull out his cock.

He reached a condom from the bowl of them on the steamer trunk. I couldnt believe this was happening as he stroked himself his hardness and rolled on the condom so matter-of-factly he could have been tying his shoes if hed been wearing any.

You can say Red anytime, Gary said from his armchair. We are big boys. We have self-control.

I nodded my understanding, taking comfort in his words. It made it easier when Jack pushed my legs wide open. Out of the corner of my eye I could see Gary leaning forward, lifting his chin see me better. Since Id gotten a wax yesterday, I knew he could see everything my open labia, my clitoris, my wetness and it aroused me even more to know Gary was seeing my body without even knowing it was mine. Jack inserted his index finger into me and rubbed along the walls of my vagina.

New and eager, Jack said with a dirty grin, clearly impressed by how wet I was. I realised quickly he wasnt talking to me, but Gary. I will open her you. You finish her off. Sound like a plan?

Gary answered, A perfect plan.

Jack gripped by the back of the knees and knelt between my thighs. This was happening. It was actually happening. I breathed quick, shallow breaths calm myself. It didnt work. Jack had his cock in his hand, and the tip pushed against my clitoris. A spasm of pleasure shot through , and I instinctively lifted my hips offer myself him. With one smooth stroke he was inside . He pushed my dress my stomach, gripped my waist and rode with firm steady thrusts. I couldnt believe I was doing this, letting a strange man while my boss watched. I lifted my head and watched Jacks cock pumping in and out of . No denying it. I was doing this. My head fell back the sofa and I turned toward Gary. I didnt mean to meet his eyes but as soon as I did, I couldnt look away. See me. I wanted to say to him. Look at me. Im not who you think I am. Im not just your assistant. Im a woman, and I need you like this. He saw me. Those brown eyes of his never left mine as Jack fucked me. If only he knew me, knew it was me. Its me. I told him with my eyes. Its me, and I want you enough I did this you, be with you.

Jack was fucking me hard now, and I opened my legs wider him. Gary moved from the chair and sat on the steamer trunk next them. I wasnt ready him touch me, but touch me he did, pressing his hand onto my lower stomach and pushing down as if trying to feel Jacks cock moving inside me. Then Gary dipped his fingertips into his wine and touched my clitoris with them. I inhaled sharply, nearly flinching at the sudden coolness on my burning body. He grinned as he rubbed the swollen knot of flesh, toying with it at first before giving it the serious attention it needed. My hips moved in tight circles as Gary touched me and Jack fucked me. sensation was concentrated in my pelvis, in my . Gary worked my clitoris with two fingers and it more than I could take. This man I adored and lusted after touching so intimately while I was being fucked. I came with a cry and a shudder, my hole gripping and grabbing at Jacks cock still pounding me. He slammed his orgasm into me as I lay back, closed my eyes and took it.

I was empty inside again and my body felt warm and drowsy. Somewhere I heard a door open and close. I was being lifted into strong arms. Limp and spent, I let the strong arms pull me upright and press me into the back of the couch. Thighs nudged my legs open and someone penetrated me again. I opened my eyes and found myself in Garys arms, my chin on his shoulder, my legs wound around his waist, as he pinned me to the back of the couch with his cock inside me.

His hands were on my back, lowering the zipper on my dress. I stiffened, suddenly wide awake.

We are alone, Gary said, kissing my bare shoulder as he slid the straps of my dress down my arms. Down, down it went until hed pushed my dress to my waist, baring my breasts him. œDont be shy.

Shy? I was finally having with the man Id adored two years. I leaned back, arching him, offering my breasts him. He ran his hands over them, squeezing them lightly, holding them in his palms as he licked and sucked my nipples. Gary was sucking my nipples and it felt better than anything had ever felt in my life. Fucking me softly at first, deeply, and then harder and harder. Jack had warned me Gary would be rougher with me than he was. But Jack hadnt warned me it would feel this good. He was fucking me so hard now I could feel it in my stomach. I loved it, needed it, had needed it ever since I went to work Gary. He pulled out of me but only turn me, bending me over the sofa arm. He entered me from behind and fucked me deep, his hands holding my breasts and squeezing them, tugging the nipples until I moaned.

You like this? he asked, and his voice sounded so unlike him. So forceful and dominant.


When Im done fucking you Im going flog you. Then you again. You want that?

Yes. I was so wet from his thrusts I felt it dripping down my thighs.

I knew you would.

But how did he know? He didnt even know it was me.

He didnt know

Red, I said.

Gary pulled out of me immediately as I yanked my dress back up.

Whats wrong? he asked, looking scared, concerned. He touched my arm. I didnt hurt you, did I?

No, I said, scrambling off the sofa. Im sorry.

He reached me again as I headed the door, but I kept walking away from him and out of the house.

What was I thinking, having with my own boss without telling him it was me? Jack knew he was having anonymous with a hed never met before. But Gary didnt, and that wasnt right. No matter how much I wanted him, how good it felt, it wasnt right.

By Monday morning, I had pulled myself together as as I could. I dressed in my normal clothes, did my hair the normal way, prepared act as normally as I could. I wouldnt blow my cover. I wouldnt confess. I wouldnt put Gary in a horribly awkward position because Id followed him his party like some lust struck puppy. I would be a grown-up and carry the secret. In the break room I poured two cups of coffee and marched into his office like it was any other day.

Morning, I said, handing him his coffee.

How was your weekend?

Good. Yours? I asked, keeping my face empty of expression.

Good. Too short.

Typical, right?

Right. But back to work. Can you bring me the Close Brothers file?

I walked to the filing cabinet and opened the top drawer. When I pulled out the file, something fell out onto the floor.

I bent to pick it up and found a black mask in my hand.

I looked at it, then looked at Gary who was smiling smugly at me with his hands clasped behind his head.

You tan easily, you know, he said. But your Star of David pendant blocks the sun. You have a -pointed pale spot your chest.

You knew it was ?

The whole time

II didnt mean . Jack was there and he asked what I wanted and I said you. Whats going happen? My heart pounded outside my chest, the mask clutched in my hand, memories of his mouth my breasts and his fingers my clitoris setting blushing and flushing and burning inside and out.

Gary stood and walked over . As he passed the door, he closed it and locked it.

What would you say a four-day weekend? he asked. Before I could answer he dipped his head and kissed slow and deep and long, his tongue touching mine his hands on my lower back and roaming lower, and his hips pushing into mine. I pulled back from the kiss and stared at him. He knew. And I knew. And wed done it anyway. And now we were going do it again.

I would say Hell yes, boss. Best idea Ive ever heard.

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