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12/15/2021 

Stephanie McMahon The Hottest Boss
Category: Roleplay Stories

Stephanie McMahon, the Chief Brand Officer of World Wrestling Entertainment is one of the hottest women on earth. And, she knows it. Guys... and gals... go crazy for her wherever she goes. Even if it's just to the market or the local deli. Someone is always hitting on her. She enjoys the attention. Her ego certainly enjoys it.

Stephanie also enjoys being the hottest boss bitch in business. She loves people groveling for her attention. Begging to be around her... and begging to please her.

That last part of that is the main job of Stephanie's personal assistant/secretary/lackey Mitch. He's a really nice, easy going, and quite shy guy. But, he's also very, very good at making... and keeping... his boss happy. That's why Steph is so fond of him.

Mitch is 20 years old. He left NYU to come work for Stephanie, full time, a year ago. He has a lot of work to do working for Stephanie. And he does it all very well. He's a real hard worker and he never complains, no matter how hard Stephanie pushes him work... or other... wise.

Mitch is a big guy. A fat, nerdy type. A red Jewfro hairdo, even though he's Irish. Big belly. Real sweet guy though. Everyone likes him. All of the women of WWE love to tease him and flirt with him since he's so shy and sweet. He just takes it and smiles... and keeps on working.

Stephanie herself gets in on the teasing action as well. She's always showing off her smooth, supple legs, or her huge, heaving cleavage to him. She even flashed him one time in her office when she got out of her shower and walked into the office with just a short robe on. She opened it and smirked at Mitch as he stared away, jaw dropped and all, then she closed it and blew him a kiss.

"For a job always well done, doll." Steph told him as she closed her robe. Mitch nervously chuckled, then thanked her for the sweet bonus.

Dude's got a huge crush on Becky Lynch. Can't blame him there. They're both Irish, but Mitch was born and raised in Westchester, so the only accent he has is that.

Stephanie knows about Mitch's huge Becky Lynch crush... so she's got a big surprise planned for him later today. It's his birthday.

"Where's Mitch?"

"Ummm... I saw him earlier talking to Naomi by the break room. She made him a birthday cake."

"Ok... thanks." Steph smirks. If only Mitch was an aggressive guy, this could really be a huge day for him, sex wise... since he's so popular with the ladies of WWE, she tells herself.

In the case of Naomi though, Mitch didn't really have to be too aggressive. Naomi handled that part for him...

"FUCK!!! YOU'VE GOT A GREAT COCK, DOLL! GOD, YES! FUCK ME, WHITE DADDY! UHHH!!!" Naomi rides Mitch in the break room. Naomi locked the door so she could give Mitch his cake... and present, all at the same time.

Mitch holds onto Naomi's gorgeous, bouncing black breasts. She's got them out of her black spandex sports bra, hanging over the top of it. She smiling at Mitch as she rides his super fat, pale white rod with the bright pink helmet on top. It's hooded, and thumping hard inside her silky slick, black pussy pie.

"Damn, baby. If I knew you had such a big beautiful white dick, I would've been fucking you way sooner. GIVE IT TO MEEEEEEEEEEEEEE!!!!!! FUCK, YES!!! WOO!!!" Naomi's huge smile so horny and electric. So beautiful and bright. She's hugging Mitch around his neck as she wildly bounces on his fat meat in the chair at the table. She leans in and kisses Mitch, who's sweating, but oh so happy.

Mitch's big white hands grope those gorgeous, dark chocolate C cups nice and hard as they swap spit. Naomi kisses Mitch nice and messy. Long strands of spit hanging from her lips to his as she breaks the kiss and leans back, smirking so naughty at the birthday boy.

Naomi grinds that meaty white cock, her black pussy sucking it all the way in and massaging it nice and wet with her juices as she grinds back and forth on it.

Mitch's big white belly sticking out, his red silk shirt that Steph bought him, wide open. His tight black leather pants that his boss also bought him getting a real nice rub down from Naomi's gorgeous, plump black butt as she grinds that portly white meat missile nice and fast. She's cooing with extreme delight as Mitch roughly massages her extra perky titties.

A few minutes later, Naomi is bent over the table with Mitch railing her from behind, that enormously fat white dick making her very happy black pussy squirt violently all over it.

"Can I please fuck your ass, Naomi? You've got such a beautiful butt. Please?" Mitch is sweating, his huge belly resting on Naomi's gorgeous, firm badonkadonk.

"Ok, but go SLOWWWWWWWW!!!!!!" Naomi could barely get the words out before Mitch shoved his entire white rod up her tight black booty. He's shaking from the intensely beautiful sensations. Naomi lurched forward onto the table from the extra large, surprise anal entry.

"GOD, THAT'S BIG! FUCK!!!" Naomi throats her head around, her long and thick, frizzy black hair flying wildly as she screams out in pure, anal banging bliss.

Mitch powers up her butt, the force of his deep dicking pushing the table around with Naomi laying on it, face down, smiling so happily as her gorgeous ebony rump is battered beautifully by Steph's sweet, fat assistant.

Mitch ends up cumming into Naomi's wide open and waiting mouth as she kneels in front of him, her tongue licking under the fat head as all of that sweet, thick cream explodes into her mouth.

Naomi very eagerly swallows a mouthful, smacking her very voluptuous lips with loving delight at the taste, then she gets another mouthful that she keeps in her mouth.

She sucks that fat crown nice and hard after Mitch stops cumming, then opens her mouth and sloshes the cum around for Mitch to see, gulping it all down quickly, and opening up to show him it was all gone. Naomi smiles and winks at him, blowing Mitch a real sexy kiss, then she sucks his pale pink dick some more, shaking her head as she sucks it, really putting on a slutty show for the birthday boy.

"Happy Birthday, baby. I'm gonna make you my new side dick. My hubby doesn't have to know a thing about you. Mmmmmmmmmmm." Naomi keeps on sucking.

"Thanks... and thanks. I'd love that. You're so beautiful, Naomi." Mitch smiles, all shy, but also real freaking happy.

Naomi rubs his big thighs through his black leather pants, and winks at him as she sucks him clean.

A little later in Stephanie's office, she has her short, white silk robe on again. Steph loves to shower at work. She'll use her treadmill of do some yoga to relax while she's working, so she showers afterwards to get all clean and sweet smelling.

She leaned back in her chair, a cigar in her boss bitch mouth as Dale... a potential new investor for a side project of hers... details his terms for their possible new venture.

"It's non negotiable by the way. Take it or leave it." Dale is super confident. He doesn't realize who he's dealing with though.

Stephanie stands up and slowly walks around to the front of her desk, sitting on it, directly in front of Dale, who his leaning back in his chair, all cocky and full of himself.

Steph uncrosses, and slowly recrosses her long, smooth legs. She rubs up them nice and easy, smoking away on that fat cigar, smirking right at Dale. He smirks back. He thinks that he's got her hooked, and that he's gonna get everything he wants.. including Stephanie. But wait...

"No." Stephanie keeps it simple. She raises her eyebrows at Dale, and blows a puff of smoke at him. She's even more confident than Dale was.

"Excuse me??" Dale can't believe Stephanie would turn him down so abruptly. The deal was all her idea. She came to him. He sits up in the chair, and looks at Steph, still cocky, but also confused.

"I said no. You will give me what I want... when I want... how I want... at the price I want." Stephanie gives Dale a very wicked grin, smokey and all, as she leans back a little on the desk, her legs still crossed.

"Oh really? And what makes you think that, lady?" Dale... the 65 year old chubby billionaire... feels challenged, so he challenges back.

"Well... man... I'm Stephanie McMahon. I always... always... get what I want. I'm the hottest boss bitch there is. I know it, and..." She slowly does her robe. Her perfect, curvy front right there for Dale to drool over. Those huge, enhanced jugs. So big and firm. That clean shaven pussy. Those long, supple legs. Steph is a goddess, and Dale knows it. "... You know it. Now... eat my pussy, bitch. We can sign the contracts later." Steph opens her legs, motioning very confidently for Dale to come over and eat her fucking pussy. She opens her slit for him to see how beautiful her pussy is.

Dale smirks again, but obeys. He dives in, sucking in Stephanie's silky slick labia, pulling them and sucking them, his tongue licking up and down those delectable pussy lips as he sucks them. Steph just puffs in that fat cigar and smirks at Dale, wrapping her long legs around his neck as he starts tongue fucking her billionaire princess twat silly.

Steph rubs Dale's face in her pussy as he tongue fucks it, wildly lapping away at each and every puffy inch of her perfect pink folds, lapping up her sweet juices as he goes.

Dale starts to stand up and unzip his pants, but Stephanie stops him. "You're my bitch, Dale. I get what I want... not the other way around. I'm the boss. We don't fuck til I say we fuck. Take it or leave it. It's non negotiable." Steph blows a big puff of smoke at him, her smirk so bossy and wide. Dale laughs, but he obeys. He wants Steph bad, but like she said... he only gets her when she says so.

Dale kneels again and starts tongue fucking Stephanie's very well toned ass this time, spreading those firm cheeks wide as he shoves his long tongue, chin deep, up in that billionaire butthole.

"Good boy. Now... toss my salad til I say stop, bitch. Hahahaha." Stephanie's cocky laugh is so sexy. She lays back on her desk and smokes, blowing the smoke up towards the ceiling as Dale tosses her supremely tasty salad for an hour straight. His tongue working overtime, rolling form side to side, lapping and licking furiously across those sweet smelling bowels. Stephanie grinning away... boss bitch style. Steph's always in charge, and Dale is learning that real damn quick.

Down the hall, in the waiting room...

"Damn, girl. You gotta try that dick. He's got a real big one. And soooooo fat. My God. He's such a sweetheart too. I told him that I'm gonna make him my new side dick." Naomi and her fellow WWE Superstar Carmella are talking about Mitch as Carmella waits to talk to Stephanie about something. "It's his birthday too. I gave him a cake... and a fuck." Naomi laughs.

"I'm sure he loved them both too." Carmella nudges Naomi's arm.

"Hell yeah! I can cook... and I can fuck. So, of course he loved them both." They laugh again.

It's turning out to be a hella good birthday for shy ol' Mitch so far.

Stephanie got Dale to sign off on the contract... at her price. And, he didn't even get to fuck her. She did invite him back tomorrow though... so maybe Dale's insatiable desire for the hottest boss bitch ever will finally be quenched then.

Carmella heads into Stephanie's office for her meeting with her. Dale walks over and strikes up a convo with Naomi. They gel very quickly. Dale can be charming when he wants to be. And he loves fucking another man's wife.

Naomi loves Mitch's big white cock, but doesn't even know that Dale's is even bigger. I guess we'll see if she finds that out or not.

After Carmella meeting with Stephanie, she runs into Mitch in the hallway, remembering what Naomi told her about his cock.

"In here, birthday boy." Carmella pulls Mitch into the ladies restroom and into a stall. "Ok, big boy. Let's see that thing." Carmella grins all naughty, very quickly unzipping Mitch's leather pants. She reaches in and pulls it out. "JESUS! THAT IS BIG!" Carmella is very impressed, her sexy Staten Island accent turning on Mitch very much. He starts sweating, his immensely fat dick throbbing and jumping before Carmella's beautiful, very intrigued eyes.

Mitch's pale pink rod is almost eight inches long, but it's so damn thick. Carmella puts her forearm next to it and Mitch's rod is wider than her forearm. She smirks real happy. Carmella absolutely loves thick cocks.

She quickly drops to her knees and laps at that huge monster. Grinning as she strings out some precum from the tip with her tongue. Carmella licks all over the fat, bulbous pink head. The foreskin covering half of the head.

Carmella sucks the crown in, sucking hard on it as her tongue lavishes the underside of it extra nice. Mitch growl happily, gripping the top of the stall divider wall as Carmella smirks at him, sucking more of his obese dick into her very experienced mouth. That bright pink head is turning Carmella on big time. She loves the way Mitch's mighty cock looks. The pale pink shaft, so thick and meaty. Veiny too. Nice and thick veins. The bright pink crown so thick and bulbous, slightly covered by the foreskin.

Carmella slurps it so well, string her spit and Mitch's precum from his piss slit to her gorgeous lips, then lapping the strand up and swallowing it as she engulfs that huge head over and over.

Carmella bobs away on that fat pink meat, her long blonde hair swirling around as her lips race up and down the mighty shaft, her mouth stretched so wide.

"Mmmmmmmmmmm. I love your cock, baby." Carmella moans around it as she speeds up her sucking and bobbing.

Mitch's happy growls intensify, getting louder and louder. His fat boy shaking as Carmella sucks down his entire cock. He starts cum spewing. His thick cream blasting the sides of Carmella's throat as she sucks it down, cooing happily from the silky sweet taste. She drains that cock of every last drop of jizz, bobbing fast on it as Mitch sweats and growls, steadying himself on the divider and the back wall.

"God, you've got the best cum I've ever tasted, baby. Happy Birthday indeed." Carmella blows Mitch a big kiss, then sucks his cock in... the whole damn thing. Her deepthroat skills are the best in WWE.

"Thanks. God, you're good." Mitch can barely stand from the intensely awesome feeling. Carmella gives him a thumbs up as she keeps on sucking.

Carmella and Mitch walk by the waiting room and see that Naomi did indeed find out how big Dale's old white dick is. It's 11 inches long and fat. Not as fat as Mitch's, but still fat. Naomi's bobbing on it as she sits next to Dale, who's grinning at Carmella.

Carmella grins back, licking her lips at that huge old thing. "Happy Birthday." Carmella quickly kisses Mitch on the cheek, the n she heads over and sits beside Dale, leaning over to help Naomi suck off that huge meat missile. It's old, but it's rock hard and throbbing. Naomi smiles and kisses Carmella, then hands her the mighty old rod. Carmella very quickly sucks it down... Yep... the whole damn thing. Her tongue lathering those old wrinkled nuts as she loudly slurps on the massive rod.

Mitch watches from across the room, grinning wide.

"Mitch... come in here, please." Stephanie sees him and calls him from her doorway. She snickers at the sight of Naomi and Carmella both sucking off her new business partner while he sits back and smokes a cigar himself, grinning from ear to ear.

"Close the door, Mitch."

"Happy Birthday, Mitch."

Mitch closes the door after staring for a minute, jaw totally dropped, at his biggest crush, The Man Becky Lynch sitting totally nude on Stephanie's beige leather office sofa, smiling at him. Her thick Irish accent such a turn on to Mitch.

Becky is his favorite wrestler and his number one celebrity crush, so his shock and much delighted surprise is overwhelming for him.

Stephanie smirks as she sits back in her desk chair, legs crossed. Her silk robe still on. Cigar still in the corner of her mouth.

Becky motions for Mitch to come to her. He finally snaps outta his Becky crazed daze and walks over to her, standing right in front of her. "My God... you're the most beautiful woman I've ever seen... No offence, Steph." Mitch looks back at his boss, not wanting to upset her after he timidly smiles at Becky. He's super nervous.

"No... none taken." Stephanie assures him.

"Thank you, sweetheart." Becky smiles.

Becky reaches up and starts rubbing Mitch's cock in his leather pants. He almost faints. His biggest crush ever, rubbing his cock... on his birthday. "I see you really are a BIG fan. You weren't lying, Steph." Becky snickers as she rubs Mitch's growing bulge. She leans in and playfully bites it through his pants.

"Oh my God." Mitch takes a big gulp. His sweating intensifies as Becky's mouth plays with his cock through his pants. Becky slowly runs her lips up and down Mitch's black leather encased dick, kinky grinning up at him.

"Can I suck it? Pretty please?" Becky confidently snickers as she grins up at Mitch. She definitely knows the answer to that one.

"UHHH... Of... Of course you can. Thank you. Ummm... Thank so much." Mitch keeps nervously sweating, trying not to faint.

"Awwww. He's so shy. Suck him good, Becky. Maybe he can fuck me too. It is his birthday after all." Stephanie grins, all naughty and horny as fuck. Mitch lays his head back and starts mumbling to himself. His level of much excited disbelief is beyond words.

As Becky unzips that tight leather pants, lapping at Mitch's fat meat as it plops out and smacks her in the face, Steph gets up and slowly undoes her robe, letting it fall to the ground, as she walks over to Mitch. She stands behind him and licks his sweaty neck, nibbling it also as Becky starts sucking on his insanely hard cock.

Steph makes sure to rub those huge breasts of hers on Mitch's back as she nibbles his neck. She and Becky both pull off his tight pants. Becky's mouth never leaves that hefty rod. She slurp it wildly, bobbing away on it, her long, blondish red hair with braids on the sides flying around as her mough ravenously sucks on the fattest dick she's ever seen. Becky can't stop moaning as she sucks. She squeezes her gorgeous, milk dribbling jugs, shooting the milk at Mitch, laughing around his cock as she furiously sucks it. Spit hanging to the floor, her tongue racing side to side underneath the massive shaft as she loudly slurps.

"HOLY FUCK!!!" Mitch starts shooting his creamy wad into Becky's very welcoming mouth. She drinks it down, bobbing fast on the cum spewing monster as it deposits it's creamy dessert into her mouth, battering her tonsils with huge globs of thick jizz. Becky very eagerly drinks it all... every fucking drop.

"Well... at least you'll have good stamina when you fuck me." Steph kisses Mitch's neck, then walks around to the couch and bends over it all slutty, wiggling her firm milf booty at him as an invitation.

Becky sucks that dick some more, then rubs it up and down Stephanie's dripping wet pussy pie. She slides it in, and Steph coos so happily. "So fucking big. Mmmmmmmm." Stephanie grins, her hands on the back of the couch as she bends over the front of it. Mitch grabs her hips and starts fucking her. His huge sweaty belly slapping on her ass every time he thrusts his mighty dick up her ridiculously juicy twat.

Stephanie's huge tits hang down and jiggle under her. Becky crawls under Stephanie and starts sucking both huge knockers, squeezing them while she sucks them as Mitch power bangs Stephanie's billionaire princess coochie. That super fat rod thumping and throbbing at it pounds over and over and over up that beautiful, clean shaven pussy.

"Do me, Mitch. Fuck me harder! Fuck Yeah!" Stephanie snarls back at him, full of animalistic sexual fury. Mitch slams up Steph's vibrating cunt even harder, his huge belly battering her booty as his thighs slap it as well. The loud slapping sounds ringing out in the office.

That big fat dick pummeling Stephanie's pussy, making her squirt two times in a row. Mitch keeps going, his stamina top notch after already cumming in Becky's mouth. He grips Steph's curvy hips nice and hard as he drives that monster dick so hard into her pussy, stretching it out as he pounds it out.

"GOD, YES!!!! FUCKKKKKKKKKKK!!!!!" Stephanie screams out. Becky shoves one of her milk shooting titties into Stephanie's mouth, and Steph sucks on it ravenously. Becky's milk splashing the back of Steph's mouth as Steph mercilessly sucks that milky C cup tit silly.

"OH FUCK!" Mitch grunts, pulling his dick outta Stephanie's violently spasming cunt. His cum spewing everywhere.

Becky and Stephanie both quickly kneel before him and take facials from that cum spewing super cock. It's so thick and throbbing so hard as the thick cream explodes from the tip. Becky sucks on the massive crown, drinking down the last of the sticky load. She and Stephanie lick each others faces clean, then suck Mitch's mighty cock nice and clean, spitting all over it, then taking turns feverishly sucking it dry.

They kiss afterwards, moaning so loud for Mitch's enjoyment. "Happy Birthday, stud. I think we should make this a weekly thing. What do you say, Becky?" Stephanie smirks, licking her cum glazed lips clean.

Becky wipes the corner of her mouth, and grins real wide. "Most definitely. It'll be our tasty little secret." Becky and Steph laugh, then both suck on Mitch's half hard cock some more.

It's definitely been the best birthday Mitch has ever had. And it's all thanks to him having the hottest boss... Stephanie McMahon The Hottest Boss.

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