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PLAYTHING part 2 (fm:sex at work, 6004 words) [2/2] show all parts

Author: jwdoney
Added: Jul 03 2026Views / Reads: 71 / 57 [80%]Part vote: 9.35 (2 votes)
Michael's sexual dreams and fantasies continue at the lusty office as his 'MEAN' boss Jennifer submits to him, Katie gets what she wants and he can't wait to be with Lisa again, but then he meets Dakota and EVERYTHING changes.
 


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She wasn’t lying.

Regardless of how awesome it was when it was happening, I fucked up when I slept with Lisa and then blew it when I screwed Candy. The worst part is after dumping me in a clear and epic way, Carrie and I still have to work together. She's polite at work, but refuses to spend any time with me outside the office. She won’t even return texts or answer my calls.

In her words, “Done means done.”

It was during my second week, I had slept with Lisa multiple times in less than three days, her Mafia boss husband introduced himself to me, made it clear he knew I was sleeping with his wife, and demanded my discretion. Well, at least I was still breathing and had no broken bones. The sex and lust at the office continued when I had scorching sex with Candy from HR, was cued up for dinner and sex with Katie, and trying to figure out if Jennifer thawing out and considering dating me was what I wanted. Plus both Jennifer and Lisa had asked me to choose between them, both sexually and professionally. I mean, I wanted to fuck Jennifer for being hot, sexy and such a bitch, but was she relationship material like Carrie was before I blew it?

Like it or not, I was about to find out sooner than I expected.

I had just left Lisa's office where we found out a box had been delivered containing a large vibrating dildo, a remote control vibrator, and a collar leash combo. She claimed she had looked into it yesterday after we hooked up, saying I had lit the slut fire in her and caused her to make bad decisions. Something like that. I called her slutty, she said I made her slutty, words like that were said. She was trying to fuck me when my brain overloaded and I needed to think.

I grabbed the collar and leash then stormed out of her office in an erotic daze.

My blood was boiling, my cock was rock hard in my pants, and God help the next lusty woman in this sex starved office that I came across. I was outside the door to Jennifer’s office before I realized that I had walked there. I was out of my mind, not thinking straight, and really, really horny. I knocked, entered, and Jennifer gasped most of the oxygen in the room, maybe the building when she saw the collar and leash in my hand. The previously ice cold, all business Office Manager Jennifer was out of her chair, around her desk, poured herself against me and kissed me like I was on fire and she was trying to put me out. I was already rock hard, dizzy, and super aroused, so her sudden burst of affection did NOT help. Jennifer shut her door, locked it, then gasped, “How did you know? Who told you? How did you figure it out?”

Huh?

Jennifer stripped like her clothes were on fire, faster than Lisa had yesterday. We kissed again, and all while I stood there holding the collar and leash I had taken from Lisa. Once she was down to her sexy green lingerie and I saw just how truly amazing Jennifer’s body was, she panted with wild eyes, “Hurry Mike. Put the collar on me and make me submit. Fuck me like a pet. Make me do anything you want."

I didn’t even blink, I just dropped the collar and leash on Jennifer’s desk then stripped off my clothes. In a span of 48 hours, including my beautiful ex-girlfriend Carrie, Lisa and Candy, I had slept with three gorgeous women, very close to four with Jennifer and I on the verge, and still had ALEXA… sorry… Katie cued up for what sure seemed to be a hot date after work.

Carrie, Lisa, Candy, about to be Jennifer and potentially Katie.

Was it Christmas?

Jennifer kissed me furiously then blew my mind when she begged, “Please fuck me? It’s been so long and I’m tired of being nice and proper."

What the fuck was going on in this office?

Even as Jennifer took off her bra, I slid her panties down and she stepped out of them. Her body was a masterpiece and I just wanted to stare. Her eyes were sex crazed and she begged, “Put the collar on me. Make me do things." I ignored the collar and leash and said, “No. I’m going to fuck the bitch out of you." Instead of a clever reply, Jennifer just moaned, “Oh God” and pulled me to her. For whatever reason, her office was smaller, had no sofa or couch, so we just did it against her desk. All of the sex in these offices was great, but didn’t any of them want to do it in bed?

Or make out?

Maybe have some foreplay?

Carrie was snug as if fitted to me, probably after months of sex together. Lisa was tight but we were able to do it… and keep doing it. Candy was really tight and it took some effort, and pain on her part, but we were finally able to have sex. None of that mattered as I pressed against Jennifer’s wet lips and she panted, “Please?” I looked into her eyes and asked, “You’ll be nice from now on?”

She nodded, and I said, “I will fuck the bitch out of you if it takes all week.”

Jennifer inhaled, her eyes widened, and then I plunged into her tight, hot, very wet pussy. She was all in and gripped me as her hips began to move and rock immediately with my first few strokes. Gasping, Jennifer panted, “If you really plan to fuck the bitch out of me, we’re… we… we’re talking weeks, maybe months.”

As I drove into Jennifer’s elite body, all I could think was, “Worth it!

Considering all the sex I’ve had the last few days with Carrie, Lisa and Candy, plus now Jennifer, I felt a surge of energy and drove into Jennifer almost mindlessly. Something about the MEAN GIRL high-speed bitch combined with her fit, perfect, destined for ONLY FANS body and model quality looks drove me past limits I didn’t know I had. I fucked Jennifer hard, fast and deep, tried to focus so it would last, and through it all she gripped me and said, “I’m yours now and I don’t care who knows it.” I was incensed and wanted to turn Jennifer inside out. I was slamming her like a door when she gripped my sides and screamed through an orgasm so intense I felt it. Not only did she splash me with her pent up juices, but she shook both of us enough to make a milkshake or maybe a smoothie.

I let go, let the moment wash over me, and felt sheer bliss as I exploded deep inside Jennifer’s perfect body. I thrust and pumped, gave her everything I had, and then we just held each other as my brain, blood and body calmed. Jennifer was rubbing my back, soothing me, then asked softly, “If I try to contain the bitch, will you date me?” I eased out of my hot blonde boss, we wiped up with a cloth she handed me, then with a glance at the leash and collar that made her blush, she asked again, “Will you go out with me?” I stood there naked, spent and happy, somehow I was sure I could fuck her again, then shook my head. Jennifer inhaled, blinked rapidly, then asked, “Is it… is it because I’m a bitch?”

Still naked, I sat in the only chair, but Jennifer surprised me when she sat on my lap, also naked and warm. She held me, kissed me, and seemed to be purring, so I sighed then said, “Since you already know about it, I have my hands full with Lisa.” Jennifer nodded, then said, “Okay, maybe I can change your mind? Until then, I promise to suppress my bitchy tendencies and treat you like an equal, especially since word is that you chose to be Lisa’s assistant.” I exhaled and Jennifer said, “Which also means you’ll be fucking her at least as much as you’ll be fucking me.” I blinked as Jennifer blushed then said, “Yeah. We’ll be fucking at least twice a day and regardless of what you and Lisa get up to, I want you to choose me so you can sleep in my bed. We can exhaust each other fucking and then snuggle and fall asleep happy.”

Wow, there was no one like Jennifer.

I said, “Sure. And then the first time I sleep with someone in this office, you dump me like Carrie did? I’m not stupid Jen, and I’m a guy. I’m going to make poor decisions when it comes to hot women. And besides, at least I was honest about being with Lisa, whatever that means.” Jennifer touched my nose, traced my lips with her fingertip, then asked, “Where did ‘Jen’ come from?” I shrugged and said, “Usually it’s short for Jennifer.” Jennifer smiled and said, “As hard as it is to believe, other than Jenny, no one has ever called me anything but Jennifer. Jen is nice coming from you. I like it.” I said, “At risk of getting slapped or fired, I’ll make you a deal.” Jennifer started stroking my semi-hard cock and purred, “Mmmm, I like deals.”

She had me hard in no time, seconds really, and she pulled me to stand up, guided me between her legs as she leaned against the desk again, then said, “Make love to me while you tell me your demands. Who knows, maybe you can fuck some sense into me?” Besides being aroused and fucking Jennifer a second time, I was feeling myself and growled as I stroked slowly into Jennifer, “I don’t think I can deal with you expecting things your way all the time, plus, not to brag, but even when I mind my own business around here, I seem to get laid.” Jennifer exhaled and frowned, so I sighed and said, “I will think about it on two conditions.” Jennifer gripped my ass, kissed me hungrily, then held me and purred, “Tell me what they are.”

I said, “No matter who I fuck or who fucks me, you cannot get bent because like you said, sex is sex, but either I’m the luckiest guy alive or the women in this office are really horny.” Jennifer raked her nails along my back and hissed in my ear, “I will tolerate some random sex, try really hard not to get jealous, but you have my word, if you want to fuck, make love, or just get off, find me and fuck me.”

Damn! Who knew?

I stroked deeper, Jennifer moaned and kissed me hungrily, then she panted, “What else?” I said, “I want you to get along with Lisa.” Jennifer moaned, then we kissed so furiously that I slowed and stopped fucking her. Jennifer was a great kisser and seemed to be riling herself up as we kissed. When she finally panted breathlessly, “Fuck me”, I bore down and gave her everything I had. She had a massive orgasm that was close to the first in sheer power and effect. Either she was extremely pent up or was a squirter, both of which bode well for me. A hot as fuck, horny, willing and wanton, pent up blonde?

I could write my own sexual ticket.

I came, it ached, but I came and spurted what I had into Jennifer who breathed in my ear, “Just know you can fuck me like a slut and turn me inside out, but I can’t get pregnant.” I gasped, “God, why aren’t you married?” She shrugged and answered, “Like you said, I’m a bitch. Who wants to deal with a strong willed, intelligent and mouthy blonde long term?” I said, “That’s what I have been trying to say. You are hotter than the sun but can flip the bitch switch with seemingly zero pause. It’s a lot to deal with, fucking you or not, so curb the bitch or I’ll curb it for you.” Jennifer smiled a scary smile and said, “Just so we’re clear right from the start? If you ever put your hands on me in anger or frustration, I will break several of your bones and drop you off at the police station.” I blinked, then Jennifer smiled seductively and purred, “However, in the correct time and place, if you feel you need to make me do something, then by all means, treat me like your personal property.”

Damn.

We cleaned up again, and still naked Jennifer kissed me and asked, “Knowing what you know, knowing you want a sexual relationship with no barriers or boundaries, if I meet your conditions, I have one as well.” I nodded as she touched my face and said, “I want, need, deserve and demand complete respect at work. Behind closed doors, fuck me like a slut and treat me like a whore. In front of others, I am your supervisor who just happens to be your favorite fucktoy.” I said, “Deal, I agree.” Jennifer kissed me warmly, then said, “Also, you can call me Jen. I like it.”

We got dressed, but Jennifer was suddenly moody, so I asked, “What? What happened?” Jennifer asked, “So no matter what I say, do or promise, you want to keep things sexual? No romance, no relationship and you prefer Lisa?” I sighed and muttered, “Why are you making me feel bad for being honest? I am seriously into you Jennifer but based on the past week or so, I just don’t think you even realize how you act or talk to people.” I felt bad for saying it, even if it was true, and Jennifer just stared at me wide eyed and open mouthed, almost as if she were shocked or stunned.

Probably no one had ever called her out for being a bitch.

I said, “I might as well tell you this now rather than have you castrate me later, I have a dinner date with Katie tonight after work and I have an overnight date with Lisa on Saturday that was made before you and I hooked up?” Jennifer flared but I saw it, she caught herself and true to her word about trying to contain the bitch, she exhaled and asked, “We hooked up? Is that what I’m worth to you?” I said, “First, I have wanted to be with you since the day I started and each day I spent around you, minus the cold shoulder bitch who made sure I knew my place, I put you on top of my mental ‘must fuck’ list.”

Jennifer inhaled, blushed, blinked then said, “Hell, I forgot what I was mad about.” I said, “I also have to go out of town with Lisa this weekend for some trip or meeting or something.” Jennifer smiled, “That I’m aware of. I think maybe it’s time to tell you something you might not like or understand.” I sat down in the chair, she sat back on my lap, and after a warm kiss, Jennifer said, “Richard is my brother.”

WHAT THE FUCK?

Did not see that coming.

I asked, “So… so… you and Lisa are…?” Jennifer played with my hair, smiled, then said, “Yes. We’re sisters-in-law. She married my brother, we get along mostly, and we keep personal stuff quiet here at work. Also, regardless of titles or position, she cannot and will not fire me and the same for me to her. Richard lets the two of us run things while he does what he does.” I was confused and asked, “But at lunch you called him sir?” Jennifer said, “Mostly playing to his ego, but also, you are now the only person besides Candy who knows our well kept secret. Aside from HR, and Lisa obviously, no one in this building or this company knows he is my brother.” I grinned and asked, “What does he do?” Jennifer smiled her evil smile again and said, “You know that you don’t want that answer, so let your mind wander and leave it at that.” I gently nudged Jennifer to get up, she went around to sit behind her desk, and then we were both blushing as we stared at the leash and collar atop her desk.

Blushing she breathed, “Would you?”

Feeling bold, I said, “You’ll find out soon enough.”

I opened Jennifer’s office door and she breathed, “Fuck me later?” I stared into her beautiful eyes and said, “I have a tough task ahead of me, but I’m willing to go all in.” Jennifer blushed redder at my pun, then asked quietly, “And the task is?” I said, “Fucking the bitch out of you while fucking the slut out of you." Jennifer moaned, “Oh God” as I just walked away.

Mostly to just think.

I found ALEXA… sorry, Katie in my office and she asked, “Do you have a minute?” I said, “Yes, what’s up?” She pouted and said, “I’m so embarrassed. I need your help with something.” I had no clue with what, so I walked beside her as she chatted about our dinner date later and asked if I liked broccoli. I shrugged and said, “Not really, but I’ll eat whatever you give me.”

I swear Katie had a flashover right there in the hallway.

It was as if her knees or legs went weak. I held her, we went into an empty office, then literally panting, she asked, “You would eat anything I put in front of you?” I realized how it sounded and blushed, but Katie shut the door, then scooted up to perch herself on the desk. Katie hiked her skirt, yanked her silky blue panties down and off, pressed them in my hand, then purred, “Lunch is served.”

I did not need an engraved invitation as I moved between her legs and was about to lick her pink pussy when I asked, “Why does it smell like flowers and vanilla?” Katie blushed then asked, “What’s it supposed to smell like?” I didn’t know so I began licking, sucking and nibbling her moist lips and everything else. Either Katie was already horny, easily aroused, or really wanted to fuck me, because she was tuned up in what felt like a short period of time. She was moaning, raking her fingers through my hair, and begging me to fuck her, so I eased back, stood, and she smiled when she saw the large bulge in my pants.

Was there no rest in this office?

I just fucked Jennifer like minutes ago.

Katie breathed, “Make sure that door is locked” as she stripped in record time while I undressed as fast as possible. I was wondering what it would be like if we were all naked in this office then laughed because there was no way that a NAKED OFFICE could be possible.

Right?

Once Katie was naked, even though I was rock hard and ready to fuck, I stared at her until she blushed and asked, “What? What’s wrong?” I said, “You’re just… I mean… Katie, for someone so small, you’re just so fucking hot and in amazing shape.” Katie blinked then huffed, “I am not small. I’m petite. 5’ is not small dude.” It was probably dumb, but I said, “I don’t care, Your body is just so fuckable that I wish I could take you home and play with you all night.”

Katie inhaled then asked, “F… fuckable? P… play with me all night?” I froze because I had just made a weird pact with Jennifer that involved seemingly unlimited sex and possibly some dominance and submission. It was difficult to focus with Katie naked, willing and me so rock fucking hard. I said, “Sleep in my bed tonight and we can decide next week.” Katie gasped, “That makes no sense, so fuck me and yes, I’ll spend the night.”

Then came the true test of sex and insertion.

Katie was tighter than all the girls combined and not just because she was small… sorry… petite. I pressed the tip of my cock against Katie’s soaked slit and she panted, moaned and pulled at me for more, but there wasn’t any more to give. Her pussy was too tight. We worked together, Katie was both gasping and whining in pain, and I had only gotten an inch or so inside her. She was really fucking tight. We kissed furiously, feverishly and hungrily, and I even tried fingering her. I stopped fingering her just shy of an orgasm and with dazed eyes and panting, Katie begged, “What? Why? Why did you stop? I was so fucking close.”

I grinned and said, “It didn’t seem like you wanted it.”

Katie was all over me and begged, “Fuck me please? I will do anything for you to fuck me.” I put my lips to Katie’s ear and asked, “Anything?” Katie kissed me hungrily, nibbled my ear, rubbed her fit body against mine, then said, “I will spend the night, the week, an entire month if you fuck me. I will move the fuck in and get engaged and fucking marry you if that’s what it takes for you to fuck me.” I was smirking as I stared into Katie’s sex drunk eyes and asked, “Anything?” Katie moaned, “Why won’t you fuck me?” I said, “I will fuck you on one condition. You can never say no to anything I ask and you have to do whatever I say or ask.”

Katie blinked several times, had wild eyes, was breathing deeply, and could not wait for me to fuck her. She grasped my cock with both hands, then asked, “You won’t ever hurt me or lie to me?” I said, “Never, but you can’t get mad at what happens in this office either.” As she held my raging cock against her needy pussy, Katie asked, “So are you going to fuck me now?” I asked, “Are you going to get jealous if I talk to other girls?” Katie said, “I could care less who you talk to or even who you fuck.” All that came to mind was ‘wow’, so I nodded, rubbed my cock against Katie’s needy pussy, and she panted, “Deal. I belong to you now, so fuck me.”

Despite the overload of sex with hot, willing women in the last two days, I was near mindless with my want, need and desire to fuck Katie. Something about her incredible looks, naughty smile, and fit, petite but perfect body drove me insane with lust. Even with her pussy soaked with excitement and her writhing and grinding against me, it took work to get another inch inside Katie. I was out of my mind and gasped, “What was it you wanted my help with?” Katie blushed, bit her lip, panted twice, and then breathed, “I was going to seduce you.”

I lost it and rammed my rock hard cock deep inside Katie causing her to scream, dig her nails into my arms, and contort beneath me. She was gasping, crying and panting as I held her and asked, “Are you okay?” Katie felt like she was shaking and hyperventilating as she said very quietly, “It feels like you broke me.” I felt bad despite the sheer desire to fuck Katie, and said, “I can pull out. We can stop.” Katie was breathing deeply, still gripping me, panted, “Wait…”, then asked, “Go easy?” I kissed her softly, her eyes were streaming tears, and she asked again, “Can we go easy?” I stroked slowly into Katie’s petite, athletic body as she stared into my eyes with what seemed like complete devotion.

Something was in the water or air in this building.

Why were all the women so dead set on sleeping with me and locking me down?

Well, except for Carrie, but I blew that one.

I was making love slowly to Katie who finally sighed a full body sigh, relaxed against and beneath me, then slid her hands to my back and asked, “Do you really like my body?” I smiled and said, “Yes, more than anyone else’s.” Katie sighed, used her fingernails to slowly tease my skin, and I was fucking her flat out before I realized it. She was gripping me while moaning, gasping and whining and then her pussy clamped around my cock, squeezed it, and she had an earthquake level orgasm that I felt for sure. Katie’s eyes rolled back, she somehow stifled a scream, and then I came deep inside her small but perfect frame.

I thrust and pumped, gave her everything I had, and then slowed before stopping and kissing her warmly. Katie was shaking as she purred, “We belong to each other now.” I held her until she sighed, “I think I’m gonna leave early and soak in a hot bath. I definitely can say now that I got fucked.” We laughed, but Katie’s eyes were still streaming tears so I kissed her softly then said, “I’m sorry Katie. I would never hurt you.” She inhaled, sniffled, kissed me on my lips, then said, “I believe you. I’ll text you my address. You can come spend the night or pick me up to go to your place, but I need to go soak if I have a prayer of getting some later on.”

I blinked and Katie smiled, put her lips to my ear, then asked, “So did we agree? You fucked me so now I have to do what you say, when you say it?” I was stunned into silence as we cleaned up, got dressed, and thought maybe Katie mentioned being on the pill. Katie kissed me softly, put her lips to my ear again, then purred, “Any demands or commands?” I gasped as she kissed me warmly, touched my face, then said, “This is going to be fun” as she hurried away.

I don’t even know how I got back to my office.

I was sitting at my desk trying to gather my thoughts when Carrie asked, “Are you okay?” I looked at her and said, “You look beautiful. I love you and I’m sorry." Carrie said, “I love you too, but I need some more time to figure things out. You really hurt me.” She sighed, I swallowed, then Carrie continued, “But I asked you a question. Is it true that Jennifer and Lisa are fighting about who gets you? How do you get yourself into these messes?”

I wasn’t thinking clearly when I muttered, “Sex.”

Carrie blinked twice then just walked away.

I stared at my computer screen, read the same email four times, then finally went to Lisa’s office. She was talking to a tall, redhead that was about my age and had a really nice body. I was confused though because while all the women dress nicely, maybe borderline sexy, this redhead was the first person I saw in the office wearing a miniskirt.

A very short, skimpy, micro miniskirt.

It was schoolgirl style, with red, blue and white plaid, fit her well despite being loose and flirty. It hung low on her shapely hips, and both sides of her thin blue thong waist straps rode high and boldly above the skirt which started or ended at her extreme upper thigh or just below her ass. It was daring to say the least and her flirty blue, backless half top exposed ALL of her tan back except for the thin string holding it in place just below her shoulder blades.

My God besides being top level fit and hot, she was closer to naked than dressed and had my FULL attention. Once I stopped looking at her gorgeous long red hair and bare back, I was staring at her long, smooth legs in her 5 or 6 inch blue heels when Lisa blushed, smiled past the woman, and asked, “Mike? Are you staring at my stepdaughter?”

Stepdaughter?

My brain froze calculating the odds of finding a redhead with blue eyes when she turned to smile at me. She was easily 6’, had light blue eyes that sparkled, a beautiful, captivating face, a large chest that visibly strained her small, fitted, backless top, and from the front, the shortness of her skirt had a sledgehammer like impact on my heart, brain and cock. I truly, deeply understood lust, desire and want at that moment.

I also instantly forgot about all the other women on the planet.

Lisa seemed to be purring as she said, “Mike, this is my beautiful stepdaughter Dakota. Baby, this is my personal assistant Mike.” Even as I surveyed and catalogued every inch of Dakota, she seemed to be studying me for a test that I sure hoped she would take. I tried to think, to focus, to breathe, but Lisa had to push as she guided Dakota closer to me and I swear besides smelling cotton candy, I could feel heat coming from Dakota’s fit, perfect body.

Yes, all the women have fit, perfect bodies, but Dakota’s is just levels above.

I don’t know how, why, nor did I care, but Dakota and I ended up hugging and I lost my mind, sanity and composure as I whispered in her ear, “You are so fucking hot.” I felt her hands gripping me, her fingers holding my clothes, and she panted in my ear, “I like you too.” We eased back, stared into each other’s eyes, I thought we were about to kiss, then Lisa was purring in my ear, “Ask her out. Be a man and…” I blurted, “Will you go out with me?” Dakota was still gripping my clothes and breathed, “Yes” and hugged me again. I held her, she was so warm, so hot, so perfect, and then Lisa said, “Oh my God, I just remembered. Dakota, can you hurry home and get me that black skirt I keep borrowing from you?” Dakota was still holding me, my clothes, and I was dizzy with excitement no question.

Dakota practically panted, “Right now?” Lisa said, “Yes. No. Wait. Oh crap, I forgot. I have so much on my mind today. Forget the skirt. Take Mike with you to your photoshoot and after, we can have dinner. Your father and me, you and Mike. My treat for my two favorite people.”

Photoshoot?

I forgot every promise I had made to Lisa, Jennifer, Katie and maybe even Candy.

Did I make Candy a promise?

In the elevator, I realized we were holding hands and it filled me with warm joy. Dakota tried to say something three times, then pushed ‘3’ and gripped my hand in hers. I was putty and for the first time in my life, could not think in the presence of a female. When the doors opened to ‘3’. Dakota led me to an alcove and we kissed. It was the hottest and best kiss of my life and I was floating when she took my phone and added herself.

Dakota said, “Let’s take your car so we can talk. When Lisa said photoshoot, she kinda undersold it. It’s a lingerie shoot.” I stood there wide-eyed and open-mouthed as Dakota waved a hand in front of my face, both grinned and blushed, then said, “Well this is gonna be fun.” She took my hand, we got back on the elevator, and then she purred in my ear, “Imagine your surprise to find out I’m a lingerie and swimsuit model.”

What?

No fucking way…

… without question, to be continued!

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