Sticking It To The Boss Lady

STICKING IT TO THE BOSS LADY

This is for the 2025 'On the Job' Story Event.

©2025 by the author using the pen name Smuttyandfun

I had just got into the office and I had to head straight to the men's room. My hands were a mess, covered in grease from helping my boss Delores with her car.

But there was no way I could just leave her stalled in the middle of the driveway with a dead battery, especially on the one of the coldest days of the year. So, of course, I stopped and gave her a boost.

Just thinking about her put a smile on my face. While I was standing at the sink washing my hands, I could picture her flashing those pearly whites, smiling back at me, when she'd thanked me.

No matter what she was wearing, she always looked really sexy. She had the perfect body; gorgeous perky tits, tiny waist and a nice curvy ass. With her long, shimmering red hair and those big blue eyes, she was an absolute knockout.

So of course, I often wondered what she'd sound like when she came. Especially if she was coming with me buried inside her.

I noticed as I walked down the hallway toward my cubical, that everyone seemed to be feeling pretty festive. Holiday decorations were strewn around the desks. Some had sparkling fairy lights, and even a few tiny Christmas trees.

What I was really looking forward to was the end of the day, when I'd be picking up the 30 lb. turkey I'd ordered to bring to my mom's, to help her out with Christmas dinner.

Though she loved entertaining the family, now that she'd retired after working forty years as a seamstress, she couldn't really afford to foot the bill anymore. Since she was barely making ends meet with her pension, I was happy to help her out wherever I could.

Tonight, when they handed me my Christmas bonus, I'd not only be helping her out with dinner, but I'd be able pick up the new winter coat she'd been eyeing. Then she could finally toss out that old thread-bare thing she'd been wearing since I was a kid.

When five o'clock rolled around, I noticed no one was getting up to leave, because they were obviously waiting for their checks.

As the time ticked on, I thought it odd that our boss Delores wasn't coming around to shake hands and wish us all a happy holiday, like she always did.

I was really starting wondering what was up, when I noticed tall, skinny Cory from the mail room, dropping sealed envelopes on everyone's desks.

When I opened mine, I dropped into my chair, hardly able to believe my eyes.

Instead of a Christmas bonus, the fuckers were giving us the boot!

Within seconds, our whole department was in an uproar; crying, screaming and most of them swearing their heads off.

The women were so upset, they all tugged on their coats, grabbed their bags, and ran out of the office, wailing.

But the guys all stayed back, trying to decide what to do.

"I think we should burn this shithole to the ground, and teach the fuckers a lesson," Joe suggested, angrily eyeing the rest of us.

"Naw, it's bad enough we got fired at Christmas, I don't want to spend the holidays in jail," Mike reasoned, with everyone nodding.

Tony pointed up the hallway at Delores's office. "Well, I say, we go fuck them, like they fucked us."

"And how do you propose we do that?" I asked, curious.

"Delores had to know this was happening, and the bitch never said a word. I bet she's known for months. Yet she let us work our asses off, hoping for a bonus, when she knew damn well that they were planning to show us the door.

"Christmas is only a few days away, and I still have to buy stuff to put under the tree for my kids. And if I show up empty-handed, my ex-wife is gonna kill me. And I don't know how I'm going to face my family, and tell them I lost my job, when they were all looking forward to a nice Christmas," Tony said, shaking his head.

"I think Tony's right, and we should go fuck her, like they fucked us!" Larry agreed, with everyone nodding.

I led the way to her office, put a finger to my lips to warn them all to be quiet, as I carefully opened the door.

Delores was facing the other way, booking an Uber to take her to the airport, by the sounds of it.

So, while she was jetting off to enjoy a sun-filled holiday on some tropical island somewhere, the rest of us shmucks would be stuck trying to figure out how we were going to afford Christmas, and where we were going to find our next job.

When they first suggested fucking her over, I wasn't sure if I could do it, but now that I'd heard her planning a winter getaway, I was angry.

Angry enough to screw her, like she'd just screwed us.

Startled, she gasped and put her phone down when she turned her head and saw the six of us bursting into her office.

I could tell from the look on her face that she hadn't planned on seeing us again, and probably hoped we'd just clear out our desks and leave. Then she could go off on her holiday and enjoy herself, and forget all about what they'd done to us, while she was sipping cocktails on the beach.

"Get up on your desk, Delores, facing us," I said.

"What?" she asked, wide-eyed.

"You heard me. And take off your panties, and unbutton your blouse. Because we're going to do the same thing to you, that you just did to us."

"Nick, you can't be serious," she said, anxiously checking the door.

I nodded at the guys and they all lowered their flies, fished out their dicks and started stroking.

"Do we look like we're kidding?" I said, pulling out my own long, thick, solid eight inches, letting it slide through my fist.

Her eyes as big as moons, she shook her head, eyeing every dick in the room.

"Please don't take it personally, it's nothing personal. But sales are down, and we had to do something," she pleaded for us to understand.

"Well, then, you can take comfort in the fact that this isn't personal, either. We're all just going to fuck you, like you fucked us. Handing us all pink slips right before the holidays was a really shitty thing to do, Delores. And you should have thought of that before you agreed to fuck us over."

"Please, Nick, think about what you're doing."

Eyeing her tight pink pussy, now that she had done as she was told and tossed her undies and spread her thighs, I smiled. "Oh, believe me I'm thinking, alright. I'm thinking how good it's going to feel when I sink my rock-hard friend into your tight little cunt. And I'm gonna pump you so full of my seed, you'll be dripping for a week. Just so you'll remember not to screw with your employees."

The guys all standing around beating their meat, chuckled. I could tell by the pre-cum dripping onto the hardwood floors, that they were all pretty anxious to have a turn with her.

"Nick, you can't do this," she said, sounding a little frantic, her eyes shooting to the door, probably hoping that someone was going to show up and come to her rescue.

"Sure I can, I've been banging women since I turned eighteen. So, I sure as fuck know what I'm doing."

Her eyes went wide, when I walked over and slipped a finger into her pussy. She was so fucking wet, I could tell, no matter what she said, that she was aching for it.

"You know what I think?"

Chest heaving, she shook her head. "No."

I smiled, and gave her a little finger bang, making her lick her lips and moan as I suggested, "I think you not only want this, but you need it." I used my other hand, to unsnap the front closure on her bra, letting her magnificent tits bounce free. I smiled as I cupped one big, warm breast in my hand. "Look at these tits. Your nipples are hard as diamonds. And your pussy's so wet, you're just dying to be fucked, aren't you, Delores?"

"No." She shook her head trying to deny it, though her sodden pussy, rock hard nipples, and heaving tits were gave her away.

"So, tell me, when was the last time you had a man between your legs?"

"I don't think that's any of your business," she sniffed, turning her head and looking away, with her cute little nose in the air.

I took hold of her chin and made her look at me. "I'll bet you haven't been with a man in years, so I know you need this. And you just can't wait to feel this bad boy pumping its way inside you, can you?" I said, gesturing at my glistening cock, flying through my fist.

They all looked around at each other and grinned from the way she was gazing at my erection with a look of longing in her eyes, that she just couldn't hide.

"Say it, Dolores. Say, 'I want this.' Say, 'I want all of you.' Tell us that you're dying to be our fuck toy. Admit it. The company fucked us. And now you want all of us to sink our dicks into your hot little pussy and fuck you."

"I can't... I can't say that."

"But you're thinking it, aren't you? Look at your tits heaving, while I'm working your pussy into a climax," I said, adding a second finger, till everyone could hear her juices clacking. "You've been desperate for this, haven't you? You need to come really badly now, don't you?" I kept working her closer and closer to a climax, while she tried to fight it off, though she kept pushing against my hand.

I got down on my knees, grabbed hold of her thighs, and pushed them open wide. The instant I sank my tongue between her folds, and started giving her a little tongue-fucking, she couldn't hold back, and she tossed back her head and cried out, "Oooh, Yes! Yes! Yes! Oh god yes! Please!"

Smiling, I kept working a finger around her clit, penetrating her with my tongue, till I had her nearly sliding off her desk, looking almost boneless, she just looked so elated once she finally let go and climaxed.

"Now, say it. Say, 'Please, Nick, fuck me!"

"Please!" she brokenly whispered.

"Please what?"

When I let go of her legs and stepped back, she relented and gave in. "Please, Nick. I want you inside me."

"That's my girl," I smiled, while the rest of them chuckled.

She was eyeing my cock, like she dying for it, but she still looked around at the rest of them and said, "But I can't handle all of you. I can't possibly take on six men."

"Get your clothes off, spread your legs. And we'll see what you say after we've made you come, probably too many times to count."

Fuck me! In my wildest dreams, I never imagined how hot she'd look, naked with her big luscious tits heaving, legs spread, pussy glistening, just aching to be filled and fucked by six big, horny men. Starting with me, of course.

Cupping her pretty face in my hands, I thought I'd start off with a kiss, like I would with any woman I was about enjoy.

As soon as I sank my tongue between her lips, and gave her a taste of her juicy pussy, she moaned and wreathed her arms around my neck, and clung to me, while I made love to her sexy mouth.

She really got into too, even sucking on my tongue, which had me smiling into our kiss.

I had a feeling one day soon, I'd be sinking more than my tongue into her mouth, and she'd be happy to feel every long hard inch of me, sliding down her throat.

I had two fingers in her pussy, getting her nice and wet, so she could handle the size of me. I wanted to fuck her, but I didn't want to risk splitting her in two. So, I knew I needed to juice her up enough to take me.

I could hear the guys groaning when, one after the other, I lifted her legs, and slipped them over my shoulders. Lining up my cock, they all watched as I eased my big, red, angry looking mushroom-shaped tip into her tight little hole, both of us moaning the instant I felt it pop in, penetrating her.

"How does that feel?" I asked her, flexing my hips and carefully starting to slide my way into her unbelievably tight pussy.

She flashed me a grin. "It feels pretty big. I can feel you stretching my insides to fit you."

"But you love it, don't you? Being taken like this, with everyone watching. Knowing they're all rock hard and just aching to have their turn with you."

She was quietly nodding her head in agreement, but I soon had her moaning, when I bent and licked each of her nipples in turn, enjoying a little suckle, and giving them each a little nip of my teeth.

"Ooh, yes!," she cried out, when I clutched her ass in my hands, and really started to ride her, hard, fast and deep. Jaw clenched, I couldn't hold back and started pounding her into the desk, as the tension began to rise, boiling up from my balls.

"Oh, fuck, here it comes," I warned her. "And I'm gonna fill you right up, and if I'm lucky, I'm gonna put a baby in you, too."

She was shivering so hard as she came, while I just kept pumping away, as the most indescribable sensation kept mounting, I gritted my teeth, and cried out, "Oh, fuck, yeah!"

Growling like a bear, I let go and came, shooting the biggest load I'd probably ever shot, right up against her womb. While Delores hung onto me like a lifeline, shaking like mad as she climaxed, clenching hard around my cock, till I knew she'd gotten every drop I had.

I took hold of myself, pulled out, and stepped back smiling, so the guys could see my seed sliding out of her swollen pussy.

"You have any idea how sexy you look right now, with your legs spread, dripping like that?" Leaning in, I kissed her and told her, "And we are going to be doing this again." She just smiled and nodded her head as she fought to catch her breath.

"You're up next," I said to Joe, who at a quick glance, looked to be about my size, but not quite as thick.

We all watched him slide two fingers inside her. And we noticed he was wearing a big pretty smile when he pulled them out, and showed us they were coated in lots of thick white cum. "Look at that. You really filled her up, Nick."

I just shrugged, while we all eagerly waited to see him push his way inside her.

"Ooh," she cooed, looking kind of blissed out, as he slipped the tip of his pinky finger into her tight back pucker, while he carefully eased his way into her juiced up puss, pulled back and thrust in a little deeper.

"Wow, you're a tight one," Joe said, as he gradually picked up his pace. "And wouldn't it be funny if we all put a baby in you. Then you'd have six babies growing in your belly. Be a good reminder of what not to do with your employees, if we all manage to knock you up."

Delores looked too elated to care, as he rode her to the finish line. Growling loud and deep, his whole body shaking, he threw back his head, and with one last deep hard thrust he shot deep into her body. Even after he'd lost his load, he still kept pumping, obviously smiling at the feel of her inner muscles clenching around him as we watched her pussy quiver.

We all laughed when he followed suit, pulled out and spread her legs, so we could see the thick white stream sliding out of her, and coating her luscious ass.

Joe chuckled, kissed both of her heaving tits, gave us all a thumbs up and stepped back, so that Mike could have his turn.

Mike quickly sat down in her chair, patted his lap and told her, "Now you're going to ride me, and show me how sorry you are about letting us go, instead of giving us our damn bonuses."

Delores just nodded, and did as he asked, got off the desk, slid a leg over Mike's thighs, and straddled him.

He was kind of on the long side, but he was really thick. So, I knew she was really going to feel it when she sank herself down, and realized how tight that much meat was going to feel packed in her pussy.

Mike was enjoying sucking on one of her titties, while she quietly moaned at the feel of him stretching her insides as slowly, inch by inch, she sank herself down, till he was buried in her balls deep, both of them groaning.

"Now you're gonna ride me, till I come. And now that you're impaled, you're really gonna feel it when I pump another load of baby batter in your hungry little cunt."

Her fingers were white, she was holding on so tightly to his shoulders, as she quietly mewled while he got off on toying with her breasts, licking and sucking and flicking her swollen nipples, while she bounced up and down in his lap riding his rigid cock.

It wasn't long till Mike was crying out, "Oh, fuck me, yes! Here it comes. Can you feel that, Delores? Can you feel me painting your insides with another big, hot load?"

Elatedly tossing her head from side to side, she cried out, "Ooh, yes! I can feel every pulse."

Everyone chuckled, watching the two of them shudder as they came, and really fucking hard by the looks of it.

Mike laughed as he took hold of his cock and pulled out, gesturing at her pussy. "Look at all that cum dripping out of her. It's like a fuckin' river, dripping all the way down to my feet. Looks like we really pumped her nice and full, guys."

"And there's still three more to go," I said, nodding at Tony, Larry and Dave, still jacking themselves, as they watched the rest of getting off.

"Okay, I guess you're up next, Tony," I said, smiling at Delores, still shivering in her chair, fighting to catch her breath. And I could see why, considering she'd just climaxed at least three times in a row, and taken three big loads.

Tony's cock was bouncing as he strode over to her desk. And he didn't waste any time telling her what he wanted. "Get up on your desk, on your knees. I want that juicy cunt right on the edge, 'cause I want to take you doggystyle, so I can watch that pretty ass jiggle while I slam you."

Delores was still shaking, but she nodded and did as she was told, carefully crawled up onto her desk, turned and got up on her knees. Careful not to fall, she inched her way back, and spread her legs open wide, so Tony could slide his way in and take her from behind.

Reaching around, Tony was filling his hands with her tits and tugging on her nipples, and groaning like mad, as he got off on the feeling of sinking his cock into her well-fucked pussy.

"Oh, fuck yeah. This is nice," Tony said, getting into a steady rhythm with her pushing back to meet his every thrust. He chuckled. "Now I'm wondering why we've never done this before. Because we're all getting off, and really enjoying banging your sweet little pussy, and watching you come."

Delores didn't answer, she just shivered and gasped, and cried out, "Oooh, yes, just like that," when he must have hit her inside, right where she needed him.

Getting closer to reaching to the peak, Tony reached under and worked her clit, till they were both gasping at once, "Oh, yes!" As they both came, the rest of groaned, watching his seed gushing out around his cock, coating his balls and splashing onto the hardwood floor. We chuckled, hardly able to believe our eyes. We had her so full, after the four of us had filled her up, her pussy was overflowing, like a white-hot guyser.

I looked at the other two and asked, "Anybody into cream pies? 'Cause I think you're going to need to eat some of that up, before you get in there and pump in another load."

Larry stepped up, slid a finger into her pussy and rolled his eyes. "Oh, yeah, she's really floating. And lucky me, I do love the taste of cum."

We all watched as he carefully laid her on her back, pushed her knees up to her chest, got his head between her legs, slid his tongue into her, and made a meal out of her creamy pussy. I gotta say, hearing him grunting and groaning as he lapped it up, was pretty arousing.

Once he'd had his fill, he stood up and wiped the back of his hand across his mouth, shaking his head. "You guys got her so juiced up, I bet I can pound her as hard as I want, and she won't even feel it. And who knows, maybe my seed'll take, and I'll be the one breeding her."

Though she'd initially claimed that she couldn't possibly handle all six of us, I noticed she had her legs spread, coyly smiling, silently inviting Larry to get his cock in her and plant his seed.

"Oh fuck, you feel good," Larry told her as he drove into her over and over, swiveling his hips, to get into her nice and deep, while also managing to hit her g-spot, making her shiver and shake like crazy.

Gasping for every breath, Delores clung to his forearms like an anchor, while Larry did as he'd promised and fucked her almost raw.

"You love this, don't you? Being used and bred, by six horny men. I think this is something you've been craving, but just never had the nerve to try. Maybe we'll come and see you again one night. And we can do this again, and fill you up, till you can't take another drop. This is what you've been aching for, isn't it, to be treated like nothing but a fuck toy. You've been so desperate to get yourself off."

Her big blue eyes locked on his, Delores told the truth. "Yes! I've needed this so badly, I can't even describe how incredible this feels."

Larry winked and smiled back at us, and we all looked around at each other and grinned. Though all we'd planned to do was pay her back for firing us the way they did, without any warning. I gotta say, it did feel pretty nice to know that she was enjoying herself as much as we were.

And who knows, maybe one of us might get the job done and breed her, and give her a baby to remember us by.

Dave stepped up last, and shook as head at how hot our boss looked with his legs spread open wide, and her tits heaving as she fought to breathe, while almost begging him to breed her.

I'd never seen anything like it. Her pussy looked sexier than fuck, after the five us had been in her, she was all pink and swollen, and just oozing with cum.

"Guess I'd better get in there too, and give you what you need, huh?" he said, kissing his way up her belly, and up over her breasts, making her smile as he sank his tongue between her lips, at the same moment he was sinking his shockingly thick, heavy cock into her quivering cunt.

"Sorry, honey, I know I'm big. So, it's just as well I'm going last. And though you're still pretty tight, luckily, you've got all that cock juice inside you, lubing you up. So if I take my time, I should be able to work my way in, so you can take me."

"Oh, my god. You're as big as a freaking horse!" she cried out, nervously laughing, as we all watched wide-eyed, as his huge, thick cock slowly, stroke by stroke, made its way into her clenching pussy, still gushing with our seed.

I reckon Dave had to be as thick as my wrist, and almost as long as my forearm, so I knew she had to be as shocked as she was overwhelmed at being plowed by that much cock.

We all watched amazed, at the way her pussy lips were stretching out, every time he nearly pulled out, before he thrust his way back in. "You do feel good, though," she said, smiling up into his eyes, as he made her grab her legs and hold them open wide, so he could look down and enjoy the sight of his big, thick monster slamming its way into her juicy cunt.

"And you feel like heaven," he murmured, gritting his teeth, as he really started pumping. "Oh man, I can feel it bubbling up from my balls. This is going to be one big load. I'm coming so fucking hard, it's gonna be gushing out of you like a river and flooding the whole freaking office."

Delores had her hands clamped around her thighs, hanging on for dear life, eyes rolling back in her head, shaking like mad, as they reached the peak and climaxed together. And no surprise, we were all hard as bricks, just from watching him pound the living fuck out of her beautifully swollen pussy.

Watching him nearly split her two with the biggest monster I'd ever seen, while she spread her legs even wider, silently begging for more, had to be the hottest freakin' thing I'd ever witnessed.

And no surprise, over the years, I'd watched some really kinky porn.

We laughed when we noticed we all had our cocks in our fists, all dripping with pre-cum.

"I wish we could go another round, but she looks pretty worn out. And I'm not sure she could take much more," Joe quietly murmured, as we watched Dave press a kiss to her lips, as he took hold of himself and gradually eased his long, thick member out of her quivering puss. Leaving what looked like a tsunami of cum in his wake, that gushed out of her gaping cunt and poured onto her desk, forming a big, white, milky pool of our co-mingled seed around her ass.

We were so absorbed in watching the two of them trying to recover, we all jumped when we heard a knock on the door.

"Oh, that's got to be my sister. We're going on holiday together. And she's meeting me here," Delores said, frantically looking around for her clothes.

We just stood and stared, amazed to see Delores's identical twin sister walking into her office.

Holy shit. Who knew she had a twin?

For a moment, she just stood, staring wide-eyed at the sight of her sister quivering on her desk with her legs spread open wide, and her red, gaping pussy still gushing from the six loads we'd just pumped inside her. Then she looked around at us, all fully erect.

Obviously, she didn't have to be a genius to know what we'd been up to.

Then the six of us looked at each other shocked, when she licked her lips, slowly began to smile and said, "Looks like you got a head start, sis."

Delores grinning at her sister, explained, "We're going to what's described as a 'Hedonist's Paradise' where there are no clothes, and no rules."

"You gotta be kidding me," I said, shocked to learn she was kinkier than I ever dreamed.

Then her sister sidled up to me and extended her hand, with her eyes locked on my erection. "I'm Shauna. And since we've got a bit of time before we have to catch our flight, I was thinking maybe I could take off my clothes, get up that desk, and you guys could let me have a taste of what my sister just enjoyed."

I noticed as Delores was carefully making her way off her desk, that she still looked a little shaky. But I guess getting ganged by six well-hung guys, and coming more times than she could probably even count, could do that to a girl.

Once she'd gather up her clothes, she looked around at us, gave us an awkward smile and said, "I'm going to have a talk with the company president in the New Year. And I pretty sure we can find some other ways to save money, so you can keep your jobs."

"Thank you, Delores," we all said at once, relieved to know we might still have a job to come back to after the holidays.

She winked. "I really hate the idea of letting you guys go, especially now that I know how hard you really work."

We all chuckled at that, since we were all sporting some pretty major wood.

Her legs clenched together, with our cum dripping down her thighs and pooling on the floor, Delores looked over at her sister and smirked. "Oh, and I should probably warn you, Shauna's the wild one. And it wouldn't surprise me if she wears all six of you out before we have to leave for the airport. So, while I go in and wash up..." She winked. "You guys have fun."