The Boss’ Baby Pt. 04 – The Mess

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Good morning, Tom!”

“Good morning, Dave!” I said as we passed each other. Dave was the IT guy that Charles had used to find the incriminating porn on my work computer that got me into this mess.

It was the first time I’d seen Dave since the incident. I was terrified of how he’d look at me after seeing some of the things I’d searched for. But he didn’t seem to show any indication of caring and he didn’t seem to notice that I was waddling past him with a large plug stuck up my bum.

I tried to seem normal as I walked up to Charles’ office and knocked on the door.

“He took an early lunch” a beautiful voice said behind me. I turned to see the stunning Secretary Stephanie wearing a gorgeous red dress smiling at me through lips painted with matching lipstick. Her raven-black hair fell to her shoulders, and her eyes seemed to twinkle behind her black horned-rimmed glasses. “He’ll be back shortly if you’d like to wait over there…”

She pointed me to a set of couches stationed in front of her desk. Her heels clanked as she walked behind and sat down at her own desk directly across from it.

“Have a seat!” She reiterated when I hesitated.

I nodded and slowly waddled over to the couch, sitting down gingerly so as to keep the plug from pressing painfully further into my asshole. The cushions of the seat didn’t help, and instead pressed the plug deeper than it’d been all day. I cringed and tried to get comfortable. Which wasn’t easy with the nylon teddy and lingerie I also had on underneath my suit.

Stephanie eyed me suspiciously, but didn’t seem to pay me much more than a glance as she returned to her work on the computer.

After about 30 minutes of discomfort in Stephanie’s presence. My Boss Charles’ finally stepped through the door laughing with 3 other men. “…and then I said ‘YOU’RE FIRED!’ and he practically started crying!!” Said one of the older white men.

They all laughed in unison, but Charles’ deep baritone voice was the most prominent.

“Tommy boy! Sorry to keep you waiting! Come here and meet the execs at the corporate office!”

My stomach probably would have dropped out of my ass if it weren’t for the plug. My mouth was agape as I slowly scooted off the couch, wincing at the wiggling of my plug. I tried to keep a straight face as I waddled over to the small crowd of businessmen.

“Tom, meet George, Stan, and Bruce!” he said, introducing me as if I were one of his pals. I shook each of the wrinkly white men’s hands awkwardly. “Tom here is one of our rising stars” Charles bahis siteleri said, enunciating the last words in a strange way.

A sense of understanding seemed to wash over the men. One of them smirked at me wickedly. “Oh I bet he’s quite the…asset!” George said. His eyes wandering.

“He certainly is.” said Charles “he spends quite a bit of time bent over a desk.

Handling anything I throw at him! Don’t you Tom?”

He nudged me. “Y-yes. Yes sir I do…”

The men all laughed as if it were some joke I didn’t get.

“Well I’m sure we’ll see you around, Tom! Perhaps at the annual Christmas Party?” said Bruce, still sporting that wicked grin.

“You sure will!” Charles said, answering for me. “Now if you’ll excuse us, gentlemen. Tom and I have some…business to attend to.”


“Please fuck my wittle slut hole, Daddy!” I cried as I bent over His desk. Pulling my burning red cheeks apart, exposing the hilt of the pink plug in my bum, dressed only in the lacy black bustier around my waist, with straps that went down to garters and fishnet stockings.


“You can do better.” He said firmly. “Make it sound girlier!”

Each slap of his hand across my already fiery ass not only sent waves of pain up my spine, but caused my butthole to clench around the plug painfully.

“Unphh! Daddy, PLEASE fuck my wittle butthole!” I squealed in a higher octave than before. I tried to make it sound convincing. I knew what he would do if I didn’t. But inside I knew there was no way my virgin asshole could handle his massive meat. “I want to feel you inside me, pounding my insides like the wittle sissy whore I am!”

“That’s better.” He said. “But you need to learn to control your little clitty sissy!” I squeaked as he flicked the back of my balls. It was the closest he’d been to touching my privates in the two weeks since I’d been his personal panty princess.

“Your little dick is leaking precum all over my freshly renovated rug!” He barked.

“I’m sorry Daddy!” I exclaimed. “I’m not meaning to!” And I really wasn’t. It pained me how excited all of this made me. My 4 inch dick was rock hard and angled painfully downwards. Hopefully my panties around my thighs would catch most of my leakage.

“Now…where were we…” he said. I felt the plug being pulled. As as hard and painful as it was to get in this morning, it was even more painful on it’s way out. I gasped and gave a very girly sounding whimper as it finally plopped it’s way out of my poor little hole.

He placed the plug on the canlı bahis siteleri desk next to me. Opening his drawer to grab something. All I could hear was the click of a cap, then felt a cold, gooey liquid slide from my tailbone and down through my crack. He then placed the head of his hard dick to my now slightly gaping butthole.

“Now, you’re going to have to relax sissy. This is going to hurt…a lot…”

And with that he pressed into my hole. Just the head invading me was enough to make me squeal, flailing my arms and knocking over papers as I reached for the edge of the desk.

“Ow! OW! Daddy! It’s too big! I…I don’t think I can handle it! Maybe if you let me suck it it’ll go in easier!” I made to stand up but he slammed me back down on the desk. Hard. Tears started welling up as he pressed his dick onward, I felt like I was being split in half. Panic set in.

“I can’t! It’s too big! Please! PLEASE!” I flailed my arms again. Desperate for anything to keep him from invading me. But he grabbed both my arms and pinned them down behind me.

“Hold. Still.” He grunted. I felt something being wrapped around my wrists. Probably my neck tie.

He spit down my crack and continued to work it in despite my pleas. I tugged futilely at my bonds as he pressed onward.

By the time it was all the way in, my tears had made a puddle on his desk. I sobbed pitifully as he took me from behind. This was not how I pictured my first anal experience to go. The sissy’s in porn made it look so easy and pleasurable.

After about 10 minutes of him using me, my hole finally started to relax and accommodate the massive python snaking it’s way in and out of my insides.

All of a sudden he started hitting a certain spot inside me. To my surprise, it sent waves of pleasure throughout my entire body.

“Unhhh….” I whimpered. Except it wasn’t a pained whimper like before, it was more of a moaning, needing whimper.

“You like that you little slut?” He chuckled.

I didn’t know what to say. I just hoped he would hit that spot again. And he did. Again and again. Soon my blubbering cries turned to moans of pleasure.

I had to be certain not to make too much noise. But I couldn’t help it. It was a pleasure I had never experienced before.

“Don’t you fucking cum on my floor, sissy!” He growled. Picking up the pace now. But with each thrust he was hitting harder and harder on that special spot.


I don’t know what happened. This huge wave of pleasure enveloped me like never canlı bahis before. My legs quaked. My body convulsed. And suddenly I could feel warm, sticky goo running down my legs and onto the floor.

“GOD. FUCKING. DAMNIT!” He yelled. I could feel his anger with every thrust as he grabbed my bound wrists and started pounding me relentlessly.

“I. TOLD. YOU. NOT. TO…CUM!!” He emphasized each word with a slam of his hips against my backside. As soon as he said the word I could feel his dick pulsing inside me. I could feel each spurt of hot goo being pumped into me. His breathing was heavy as his cock withdrew from my ass and he plopped down on the chair.

“Look at the mess you made you fucking whore!” I’d never seen him angry like that.

With my hands still tied behind my back, I lifted myself up and looked down at the huge puddle of my own jizz staining his carpet.

“Get down there and lick that up.” He barked.

I’ve never dropped to my knees so fast. His rage was terrifying. I started lapping up my mess like a scolded puppy.

After slurping as much of my semen as I could off the floor, I looked back up at him. Hoping his anger had subsided.

It hadn’t.

He pressed the buzzer of the intercom. “Stephanie, will you bring me those D.P.R. forms please?” There was a short pause for a couple seconds. Finally, followed by “right away, sir.”

Oh shit. Stephanie was coming. She could be here any minute and would see me in my slutty lingerie.

I tried to crawl underneath his desk and hide. But His legs stopped me. “Na uh, I think you’ve had enough of MY dick today you little slut”

I started scrambling. I had to get my clothes on before she came in and saw me like this. But that’s easier said than done when your hands are tied behind your back.

I didn’t even get my panties back up around my waist by the time she walked in.

Her eyes immediately met mine. I expected her face to be horrified as I stood before her. Frozen in my ridiculous lingerie. But she barely spared me a once over before turning to her boss as if nothing were awry.

“I have the um…forms you asked for, sir.” She said. Clutching a clipboard to her chest.

“Excellent.” Charles said, standing up. Unapologetic about his dick swinging between his legs while he pulled his pants up. “If you’ll administer them to Tom here, I will be back shortly.”

And with that, he pulled up his pants and stormed out of his office without another word.

She smirked and turned to me as soon as he left. Pulling the big white form out from behind her clipboard.

“So…what did you do to earn this?” She asked. Smiling wickedly as she held up the big white form.

But at second glance I realized it wasn’t a form. It was a very large diaper.

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