Matt's BossStory by WamSam1224Posted saturday 311 views
You walk up to your boss's office, palms sweaty already. A big report was due and you had gotten too distracted to finish it on time. This hadn't been the first time you had gotten distracted before a deadline, but it was the first time you had been called in by the big boss.
You gently knock on the door, then when nothing happens, you knock again harder. "Come in," a cold voice answers. A slim, dark woman sits behind a large desk you swear her glare could pierce straight through you. You've always had a thing for Ms. Smith, but her reputation was known around the branch as being a hardass. You realize your armpits are starting to sweat through your shirt.
"II" you faltered, her gaze melting what little confidence you had left.
"Well? What do you have to say for yourself? That report was due days ago and yet here I am still waiting."
"I'm so sorry Ms. Smith, I'm not sure how I ran out of time. It was so close to being done andthen I just got distracted I guess."
"Distracted?!" She slams her hands on her desk. "I don't believe this... You are normally such a good little worker bee. And yet you've failed to get the report in on timetsk, tsk tsk Why couldn't you do it?" She smirks, then sits back and sighs. "I guess I'll just have to punish you for this..." Staring mischievous daggers at you, she points at the floor expectantly. Wondering where this is going, hope springs forth in your chest as she points at the floor.
"I'll do whatever it takes, boss. Just let me know. I'm very ready to please you. Ummmm so you want me down on the floor, like this?" You kneel down on the floor in the middle of the room. "I can beg. Please--please let me keep this job! I promise I'll get that report to you as soon as I can."
Leaning forward in her chair, her mouth curves into a vicious smile. "Mmm... Now that's what I like to see. You look so natural on your knees. Do you spend a lot of time on them?"
"On my knees, you mean, like, like working around the house?" She couldn't possibly mean what you hope she does. Snippets of fantasies you've had during her presentations flash by as anyone looking closely can see your pants grow tighter.
She chuckles, "Suuuure.... Let's say working around the house. Or maybe in a garden? Or maybe you walk your dog like that.... Maybe you ARE the dog to be walked."
Ms. Smith leans forward, unbuttoning her top button to reveal some cleavage. "Are you a good boy?"
You tilt your head up to catch a glimpse. "Uh, well Given the circumstances boss, I think I've been a bad boy. I have to admit that all the time I should have been working on that report, I've been watching porn"
Her mouth opens in shock - "Pornography?! You've been watching PORNOGRAPHIC MATERIAL on a work computer??? Oh my... You HAVE been a naughty boy... So that means you'll need to be punished!"
She finally stands up, revealing that she's been wearing her clear purple strap on this whole time. She crooks her finger at you: "C'mere boy, crawl over to me and get what you deserve."
"Oh! I I Yes, boss," you respond demurely as your blood starts pumping.
You make sure to crawl with your hands and knees firmly on the floor. This surely can't be good for your suit pants, but that's certainly not at the front of your mind.
Ms. Smith strokes her cock with anticipation as she walks towards you. "You were so foolish to watch porn at work. Is THIS what excites you-" she asks as she grabs the back of your head and shoves her dick in your mouth. She adjusts to find a good angle and starts pumping.
You wrap your mouth around her thick purple shaft her pace is frantic, sliding over your tongue and banging the back of your throat. She's enormous, especially compared to you
She pulls out of your mouth to allow you to catch your breath, enough to sputter: "I think I have a problem, boss. I just can't stop." Sheepishly, looking up at her you ask, "And how did you know that I watch lots of pegging videos?"
"Let's just say my shock wasn't completely genuine..." Ms. Smith winks before she stuffs her cock back in your mouth. "In fact, knowing that you enjoy porn so much" - she hits a button on her desk - "why don't you star in one, yourself?"
The shades on her office windows automatically start rolling up to reveal the entire floor watching behind the glass, some giggling into their hands, others pointing and unlocking their phones.
"Now then Matt.... Unbutton your shirt!" she commands, waving at our audience.
Simultaneously mortified and aroused you can't help but obey. Your fingers fumble down the front of your shirt. Why are they always so hard to open when you want them to!
She thrusts her cock and hits the back of your throat so much that you start slobbering. "Aw, isn't that sweet? My little bitch is drooling for more!" Our audience erupts into laughter.
Finally able to get your shirt off, she thrusts her cock and hits the back of your throat so much that you start slobbering. "Aw, isn't that sweet? My little bitch is drooling for more!" Our audience erupts into laughter.
"I suppose I should give you a little more then, eh? " she pauses, allowing you to catch your breath. "Turn around, pull down your pants and stick your ass in the air, " she orders strictly.
*Ggggaahhhhh* you slobber moan before she pulls out.
You glance at the audience and realize things are going to be very different around the office after this. You pull your pants down aw man, what a day to go commando!
Ms. Smith opens the top drawer of her desk to grab a large bottle of lube. She squirts some onto her hand and start massaging the slobber off her cock.
"Brenda? Could you bring the package in for me please?" she calls out. her personal secretary, a 5'4 bosomy blonde, strolls into the office with a large bakery box. She sets it onto the floor next to your face.
"Make sure it's placed properly," Ms. Smith warns her. Brenda nods, giggles, and breaks down the box to slide the large, colorful cake directly next to your face.
It seems like Brenda might have been expecting this. You have a hard time not watching her ass as she leaves.
You take a look at the cake Wow, they've really covered it with a lot of extra frosting!
"Are you ready to become the laughingstock of the office, my little porn star?" the boss teases with a smirk.
"Ummm Cake You really do seem to know all what I've been watching when I should have been working on that report," you cringe, mortified to remember she has access to your work computer.
With pants down around your knees and your ass in the air, your cock throbs with anticipation.
"Go on, announce to our audience what you like to watch!" the boss taps her cock against your ass, preparing you.
"Ummm I like to watch videos of women fucking guys with big strap-ons, and I like to, uh, watch videos of people getting slammed with cream pies and cakes and other mess And I especially like to watch videos of all this happening together." You close your eyes and listen to the muffled laughter and guffaws from your coworkers.
Ms. Smith throws her head back and laughs triumphantly. She then angles her cock into your ass; as she pushes in, the force propels your face directly into the gloopy cake. All the extra frosting bunches up around your ears and for a moment you are blind and deaf. But she pulls out long enough for you to slightly lift your head to hear the audience cheering you can feel heat flushing your cheeks. Your boss starts to pump; each thrust pushes you deeper and deeper into the thick cake with a spongy base.
Your boss slaps your ass, and you jump. Blinded by the frosting, all you can feel are her hands grabbing your hips and her cock inside of you. It's impossible to tell what she'll do next, but you relish every humiliating moment. You try to say something, anything but your mouth and nose fill with cake.
"Aw, are you enjoying yourself?" she chastises. "Are you having fun getting dicked down by my fat cock?"
You spit out enough in between thrusts to exclaim, "Yes, yes boss!"
"Is this the kind of filth you like to watch while at work?"
"Yes, I fantasize - about chicks with dicks - throwing pies at me," you admit in between pumps. Her cock fills you up entirely, stretching your hole more than any toy ever has. You can feel a bit of precum dribbling out already.
"Hahaha, I thought so!" the boss mocks. "Oh, Brendaaaaa!" she calls out gleefully. She's clearly enjoying herself.
Brenda walks back in with a wheeled table full of pies. You feel her slide out of you only to forcibly flip you on your back. What's left of the cake provides a creamy pillow as your boss bends down to heft your hips onto her cock and slides herself back in again.
"Now Brenda, be a dear and pass me a pie?" Brenda obliges obediently and the boss starts slowly thrusting; she allows you to wipe your face only to drop the gooey treat right onto your face. Your mouth opens reflexively and fills with cream. Your ass clenches tight around her cock and your penis starts bouncing upright. Pie crust slides to either side of your face and coats the collar of your button up.
"That's a good little slut," your boss coos at you. You find your ass instinctively bucking and grinding to the rhythm of her thick purple shaft. You blink away the swirls of cream around your eyes.
Brenda shifts as she looks on, biting her lip. The boss notices her and asks, "Oh? Do you like what you see?" The busty blonde smiles big and nods, wringing her hands. "I see....," the boss says coyly, the gears clearly turning in her head. "Another one," she orders, and Brenda hands her a cherry pie. This confection gets tossed gently onto your face so that it splatters wide, including on Brenda's shoes.
"Oh no!" the boss feigns surprise. "Look what you've done, Matt! You messy slut, you've gotten Brenda's shoes dirty! You better lick them clean if you want to keep this job." Brenda gently sticks her shoe in front of your face. "Ye-yes boss," you comply, lapping at Brenda's shoes that she waves in your face. Your tongue dances over the rough, cheap leather, and you can't help but drool a little.
"I'm so sorry, Ms. Smith and Brenda. If I wasn't such a horny slut I wouldn't have gotten these shoes messy."
"Now, why don't you offer a different kind of apology? Brenda, if you will..."
Brenda hikes up her pencil skirt around the waist, crumpling the slick material. She crouches down over your face, her crotchless panties conveniently in the right spot. She opens your pants and starts licking the top of your already-wet cock.
You eagerly start licking her clit and pussy, moaning while she runs her tongue around the head of your cock.
Ms. Smith pulls Brenda up, slaps a pie onto your cock, and pushes her head down again. The crowd roars with delight.
After a few minutes of rhythmic pounding, Ms. Smith makes Brenda pause so she can slap a pie on your face before resuming. The cool sensation of the cream and overwhelming enthusiasm of your tongue make Brenda moan with pleasure. She squirms as her moans get higher and higher, and although you can feel your jaw start to ache, you know you must continue.
Brenda quivers as you feel her cum all over your face. As you feel it meld with pie and crust, Ms. Smith has her stand up. At this point, your cock is erect and ready to burst. Brenda is ordered to take a pie and cover your panting face with it. She splats three more on top, slowly forming a goopy mountain around your head. Meanwhile, Ms. Smith grips your thighs even harder and thrusts as hard as she can. Now that she doesn't have to worry about Brenda's pleasure, she uses your anus as her personal fleshlight.
You can't see or hear anything The world is almost silent, apart from distant laughter and panting from your feverish fucking. Ms. Smith slams so deep inside of you that it almost feels like your own cock gets longer, like an extension of her cock. You are Ms. Smith's personal fucktoy.
Finally, you cum to a cacophony of whoops and cheering, a mini creamy volcano erupting all over yourself. The sounds of everyone watching and laughing come flooding in, rudely awakening you to the pathetic mess you've become. Ms. Smith stands back and gives you a moment to collect yourself before making you stand up and take a bow. You stand awkwardly, your ass sore then Brenda pops up with the last two pies and slams them in a grand pie sandwich. Phones flash as your coworkers jeer at your utter humiliation. Ms. Smith finishes by making you grovel at her feet, kissing both her shoes and Brenda's for allowing you to keep your job.
Exhausted and dazed, you collect your shirt and pants, crumpled in the pile of cream and crust. Head hanging you make for the office door for your inevitable walk of shame past all your onlooking coworkers.
"Oh and Matt?" Ms Smith calls. "I expect that report on my desk in an hour." She smirks at you. "Tick tock."