The Boss' Baby Part 10 - Office Christmas Party

It wasn’t held in our office building. The company spared no expense as they rented out the ground floor and grand hall of an expensive hotel. Everyone I worked with was congregated around a giant Christmas tree in the middle of the ballroom.

My wife Amy looked positively radiant. She always looked beautiful, but tonight she was wearing a tight black sequin dress that sparkled in the glow of the tree. Her blonde hair done up perfectly in an elaborate bun. I was wearing one of my best, most expensive suits. It was a perfect night. Other than the diaper I had on underneath.

“What’s wrong?” She asked, noticing my discomfort. “I told you you didn’t have to wear that thing.” She nodded towards my pants where my diaper crinkled underneath.

But I do have to wear it... I thought. Boss’ orders…

Speaking of, Charles approached, smiling. He wasn’t married, so he didn’t have an official guest. But Stephanie was right next to him. She also looked glamorous. Her raven black hair framed her face perfectly, and her curves in her red dress made my cock twitch inside my cage.

“Hi! You must be Amy!” Stephanie said in that cheery voice girls use when they first meet each other. There was a hint of a wicked smile as she shook Amy’s hand, glancing at me. “Have you met Charles? He’s our Boss. Tom has definitely been sucking up to him quite well!”

They all laughed. I cringed. There were so many unspoken things going on that both parties knew about. Like the fact that I'd been blowing Charles. That he suggested (more like ordered) I be put in diapers, and that Stephanie was the one changing me during the day and was the other holder of the key to my cage.

Conversely, Amy knew I was in a diaper and cage right now too, but didn’t know Charles and Stephanie were the ultimate masterminds behind it.

“Yes, Tom has spent a lot of time bent over a desk, hard at work!” Charles chuckled. “There are talks of a promotion in the future!”

Amy gleamed. “Well that sure would be wonderful! I’m sure he’s learned a lot from a...powerful man like you Charles!” There was admiration in her eyes as she looked the chiseled man up and down. I was sure I saw a glint of something else in her eyes too.

“I’m going to grab something from the bar...” I said to Amy, trying to make things less uncomfortable. “Do you want anything?”

But it was Charles that answered, “I’ll take a Scotch on the rocks.” He said pointedly. “Stephanie will have a Cranberry Vodka and...Amy?”

“Champagne.” Amy said, a little taken aback by Charles' forwardness, but not seeming to mind very much at all.

I knew better than to argue, so off I went. Crinkling to the bar while Charles said something that made both the girls laugh.

“Scotch on the rocks, Cranberry Vodka, and two glasses of Champagne please.” I said to the bartender. Suddenly there was a hand on my shoulder.

“Tommy boy! There you are!”

I turned around to see George, the creepy old guy from corporate, smiling with that predatory grin of his. He was with another older white gentleman.

“Uh...hi George...” I stammered, praying the drinks would arrive sooner so I could leave.

“I was just telling Mike here that we need more...talent...like you moving up to corporate!” He chuckled as he slipped a card into my hand. “In fact...why don’t you make your way up to the 5th floor for a...debriefing. Within the next 5 minutes should suffice. Unless you...wouldn’t like to have a job at all” he looked down at me menacingly as he sipped his drink. I knew from how uncomfortable Charles was around him that he meant business.

“Yes sir...” I said as the drinks were placed on the bar. George and the man laughed as they turned back to the party. Before grabbing the drinks I glanced at the card George slipped me. It looked like a business card, with gold writing stenciled:

Admit One. Floor 5.

But what room was I supposed to go to? I guess I'd figure that out soon enough. I headed back to the group where Charles, Amy and Stephanie were still laughing.

“Honey, can I talk to you?” I asked, pulling Amy aside.

“What is it sweetheart?” She asked, sensing my tone. “Do you...need a diaper change?” She whispered the last part. Smirking a tiny bit.

“Wha? No I...” was caught off guard by that “i...i need to go upstairs...there’s...some guys from corporate...”

“Oh!” She gasped, as if understanding, “maybe this is about that promotion!” She clapped her hands in glee.

I sighed. “Yea...maybe...”

“Don’t say ‘maybe’! You got this! Give it your all! I’m sure they’ll be begging to have you!!” She kissed me on the cheek. “Now go! I’ll be...be fine down here!” And she turned back to Charles a little too eagerly.

********

There was a bellhop on the elevator.

“Where to?” He said.

“5th floor please.”

He stopped. “Do you have...”

“Oh...yes....” I said, handing him the card, my hand shaking. He examined it. Looked me up and down. Smirked. And nodded. Putting a key into the control board and turning it so that the button to floor 5 would activate.

I trembled as the elevator rode smoothly upward. There was a ding, and the doors opened.

The entire floor was filled with people. But unlike the party downstairs, it wasn’t filled with people in tuxes and dresses. It was filled with people in lingerie, latex, or very little clothing at all.

The bellhop shoved me out of the elevator forcefully, I turned around to try to get back in, but was grabbed by two big bouncers.

They held me still while the door closed. Once it was gone they released me. “You gonna strip or we gonna have to do this the hard way?” One of the big bouncers asked.

I trembled as I removed my very expensive tux and stripped all the way down to just my diaper. I would have felt out of place, but not 10 feet away from me were two sissies naked on their knees with their mouths open and a sign around their necks that said “Garbage”. I watched as a man in a suit walked over and spooned the remainder of his plate into the sissy’s mouth.

“Drinks?” Said a voice. I turned to see a beautiful cocktail waitress smiling at me holding a tray of beverages. I hesitantly grabbed a glass of champagne and downed it immediately, then grabbed another. She smiled. But then I looked down at her lingerie and noticed a cock cage like mine dangling between her legs. “Word of advise?” The sissy waitress said. “You’re in a diaper, so you might want to crawl around. Unless you wanna end up like them over there...”

She pointed to the far wall where 3 sissies were bound spread eagle to 3 big X-like structures. Men and women took turns taking a bullwhip to all of their backsides. Laughing as they squealed in pain.

I needed no further prompting. I gulped down my third glass of champagne and dropped to my hands and knees. Crawling my way through the crowd of kinky people. Not even sure where I was headed.

I made my way through a sea of legs. Not sure if the ones in heels belonged to actual females, or sissies like me. I felt my diapered bum being patted and groped by creepy strangers as I sauntered by.

I decided to follow the music, which led me to a stage with a bunch of lounge chairs surrounding it. A bunch of older men sat back as sissies serviced their wrinkly cocks with their mouths. On stage there was a sissy spinning around on a pole. They chuckled as they sipped their whiskeys and jizzed in the sissies’ mouths.

At another stage was a man with a microphone. He sounded like an auctioneer. Rambling on about the three “pigs” he had on stage. “This one squeals like a wittle piggy as soon as you put anything up his ass.” He said, smacking one of the fat sissies that was on all fours. He had a rubber pig snout on his nose.

There were men and (real?) women in front of the stage, holding up signs to signal for their bids.

I crawled away as fast as I could.

In the next area there was a group crowded around a sissy strapped to a sawhorse. Two machines on opposite sides of her, pumping giant dildos thut spun like a drill in and out of both her holes.

“Looks like she’s close to cumming boys! Place your bets! Over/under 30 seconds! 10 to 1 odds!” Hollered the man standing next to her.

In another corner was 6 sissies on their knees facing a wall. They bobbed their heads back and forth on what I presumed to be dildos. There were large meters above each one that looked like big thermometers. And every time the sissy went forward on the dildo they pushed a button with their nose, moving the little stick figure higher.

“Looks like #4 is in the lead, but #5 is coming in hot!” Called the announcer, “oh #3 is making a comeback, but will he make it in time?” The crowd around was hooting and hollering and holding up wads of cash. “Ohhh! And it looks like 5 is the winner!”

There were cheers and jeers as the sissy with number 5 around his neck was turned around and his arm raised. He was sobbing for some reason. It wasn’t until the announcer used a key around his neck to unlock his chastity cage that I realized they were tears of joy.

It was like some kind of sissy circus or casino. Everywhere I looked someone was getting fucked or sucked, and there always seemed to be money involved.

“There you are, Baby!” Someone said. I glanced up to see another one of the Corporate white men I met before. I think his name was Bruce? “You’re needed on the side stage!”

He pulled a collar and leash out. Wrapping it around my neck unnecessarily, and led me over to a small platform where people were already gathered. I trembled as I crawled up the ramp where there was another sissy waiting. This one was in much more elaborate attire than me. His large pink bonnett, bib, mittens, and booties were a stark contrast compared to me in just a diaper.

Bruce removed the leash attached to the collar once me and the sissy were facing each other on all fours. He picked up a microphone “good evening ladies and gentlemen!” His voice boomed. “If you’ll head to the side stage, you can see two sissy babies attempt to take on: The Pacifier!” He said this last bit with exaggerated flair. There was already a crowd forming around the stage.

Soon a large object was tossed in the middle of us. It was a large double ended dildo. In the midpoint of the dildo was a plastic ring shaped like the plastic part of a pacifier.

“Each end of the dildo will be placed in the sissies’ mouths.” Bruce explained, and as he did an assistant lifted the 2 foot dildo, forcefully putting the tip into each of our mouths. “In the center is a plastic ring. The sissies will try to move the plastic ring as far as they can to the opponent’s side using only their mouth and deepthroat skills. They have 5 minutes! Place your bets!”

The crowd erupted into calls. “100,000 on the pink one!”

“150,000 on A! It’s the sneaky ones that are kinkiest!”

“B’s got it! I’ll put 500 on it! Pansies that wear pink know how to take it!”

I noticed there was a large tag hanging from the other sissy’s neck that read “B”. Mine must say “A”.

“Begin!” Shouted Bruce, and a timer next to the stage started ticking down from 5:00 minutes.

The sissy opposite me immediately began pushing forward, causing the other end dildo to push against my throat. I still hadn’t learned to control my gag reflex. I choked, but the sissy kept pushing. Swallowing the other end of the cock until his nose was able to push the ring. He only moved it an inch or two, but it was easy to see it was past the red line that marked the center of the dildo. I tried to take the dick down my throat and push it back, but my gagging kept me from getting even close to it.

There was cheering from the crowd as the other sissy closed his eyes and leaned forward, forcing the cock even further down his throat, past the red mark, and nudging the plastic ring even further.

I glanced at the clock, 2 minutes left. Now that the ring was closer to me it was easier to reach. I nudged it forward, but it wasn’t enough to move it to the halfway point signified by the red line.

1 minute.

I drew in breath around the rubber cock filling my mouth and tickling my throat, then exhaled. Wincing as I forced the cock as far as I could down my throat. Encouraging shouts from the crowd helped. I relaxed my throat and blinked back tears as I nudged the ring forward, past the red line and over. I was proud of myself, and the cheers from the crowd made me feel even better about my dicksucking skills.

But there was still time left. 20 seconds. I was too tired to push any further. Instead it was the other sissy’s turn to swallow the dick and send it back over to my side. Just past the red line as time expired. “Baby B is the winner!” Bruce called. The crowd bellowed with a mix of happy and angry shouts. As if we were nothing more than a roulette wheel to them.

Me and the sissy both relaxed and let the dildo fall from our mouths onto the stage. Breathing heavily.

“Now...we have time for one more event...what should we make them do?” Bruce beckoned to the crowd.

“Ass to Ass!” One of them shouted. And the rest of them agreed. “Yea!! Ass to ass!!” “Ass to ass! Ass to ass!!!” The crowd chanted in unison.

Two assistants came and turned us both around. Untaping our diapers and lubing up our assholes.

“Awww! Looks like the last event got our wittle babies excited!” Bruce cooed. I looked down at my urine soaked diaper and noticed a string of precum making its way down from my caged cock. The other sissy’s was doing the same.

“First to cum completely from fucking their ass, wins!” The crowd cheered and started placing their bets. The assistants held each end of the dildo to our lubed up holes. “BEGIN!”

I tried to force myself backward on the cock. Feeling it bend as the other sissy did the same. With the help of the assistant, we managed to work it into each of our holes. Crawling backwards to snake more of it in.

This was as much of a team event as it was solo. As we both had to work in unison and build up a rhythm to work the dick in and out of our assholes. Money showered us from all directions as the crowd hooted and hollered. Soon both of our ass cheeks were clapping against each other as we bounced back and forth.

The rubbery cock actually felt good inside me. Stimulating my prostate and giving me the biggest sense of pleasure I'd had in weeks. My aching cock pressing inside its cage. Desperate for relief. But I could hear the sissy moaning behind me. He was getting close.

I tried to hurry. But a cheer from the crowd told me I'd already lost. I glanced back to see the sissy convulsing behind me. Goo shooting through his cage and down into his diaper. “And B wins again!” The announcer hollered. Some onlookers yelled at me for losing.

“Pathetic!”

“Fucking faggot!”

“Learn how to take a dick!”

I sobbed pathetically as the assistant put my diaper back on.

*********

“That was quite the meeting!” Amy said in the car on the way home.

“Yea...sorry about that i...i wish i didn’t have to stay so long...” I mumbled. I was back in my suit with my diaper underneath. But my hole was abused and my throat was sore.

“Well did it go well at least?” She asked.

“Not really...” I said. “But I did get a nice bonus!” I pulled out the wad of cash that was thrown at me on stage. “Almost $2,000!”

“Wow! Maybe we can do that trip to Cabo we’ve always talked about!” She gleamed.

“Yea...maybe...” I said, shifting in my diaper.

“What’s wrong?” She asked. “Is your diapy wet?” She giggled, reaching over to squeeze my crotch. Making my balls ache even more.

“No...it’s just...I'm sorry I had to leave you for that long...” I said.

“Oh...that’s okay...” she smirked, “Charles kept me company.” She had a weird look in her eyes. One that would haunt me for the rest of the weekend.