The Boss' Baby Part 8 - Busy Day

It was a busy day.

My morning started with Dave from IT emailing me to come down to his office. I knew exactly what that meant.

“What did she say?” He asked as I bobbed my head on his cock.

“I have to do her a favor first,” I said, using my saliva as lube to stroke him while I talked, “but that should be done today”

I was referring to the chastity cage Stephanie wanted me to wear in order to get her to go on a date with Dave. The plan was for my wife Amy and I to go pick one up after work.

“Did she say anything about me?” He asked while I sucked his balls.

“That she hopes you don’t have a small dick…” I said.

“Well…” he smiled, grabbing me by the back of the head and shoving his cock back down my throat, “at least you know that isn’t true.”

*****

“What’d she say?” Stephanie asked as she applied my makeup in Charles’ office. “About the diapers?”

“She took it…surprisingly well.” I said, trying to get used to the weight of mascara on my eye lashes.

“Of course she did,” She laughed as she pulled my hair into two tiny pigtails, “she’s probably thought a loser with a baby dick like yours should have been diapered a long time ago. Do you have the picture?”

I opened my phone and showed Stephanie the picture of Amy smiling as she changed my first poopy diaper. “She was happy to do it…she just didn’t want it to end up on the internet.”

“Well as long as you’re obedient it won’t have to. Now send it to me for my records.” She said.

Just then, Charles walked into the office, followed by the older white man from corporate, George. Again I expected someone to look taken aback when they saw me on my knees dressed like a girl. But George didn’t bat an eye. Just flashed a toothy grin.

“Ahh, so this is your rising star,” George said as he circled around me. Inspecting me like I was a piece of meat at a livestock show.

I knelt there trembling in my lingerie and diaper. Not daring to move. “Needs bigger tits” he said, groping my chest. “Open” He said, shoving a fat grubby finger into mouth, swirling it around.

“Teeth are a little big, but those can be removed eventually. Can we take this off?” He said, referring to my diaper.

Stephanie hurriedly rushed forward and removed the tabs to my wet diaper. Allowing it to fall to the floor.

George flashed a creepy smile. “Ohhh now there’s a nice piece of ass!” He said, squeezing my cheeks and making me yelp as he smacked my backside. “Why is this not caged?” He asked, pinching the head of my cock painfully.

It was the first time I’d seen my Boss Charles gulp uncomfortably. “He uh…”

“He will be getting one today, sir,” Stephanie interjected from the corner.

“Excellent. It’s very important to keep these faggots on edge. Makes them more eager and obedient” said George, smacking my ass again.

Charles cleared his throat “He’s quite the little slut, George.” He said, circling me as well. “Not the best at sucking dick yet, but what he lacks in talent he makes up for in enthusiasm.” I glanced over to see Stephanie stifling a snigger.

“Good…good…” said George, “well I want a quarterly report on his progress before we make the decision to move him up to corporate.”

“Of course, sir,” said Charles. It was weird seeing a big dominant black man like Charles seem almost intimidated by a frail, creepy old man like George.

“Very good.” Said George, removing his tie. “Now…let’s see how well the little bitch can take a dick.”

I spent the next hour bent over Charles’ desk getting spitroasted.

Charles took me from behind while I slurped on George’s wrinkly old penis. Stephanie stood to the side with a clipboard writing down notes as George called them out.

“Needs to learn to use his tongue more”, George would say, “Suction on the way up, not down. Drool more. And watch those fucking teeth!”

Then they would switch. Charles moving to my front and George to my back. George’s 5-inch dick was nothing compared to Charles’ 8.5, so I actually was okay with the switch. Even though Charles did everything he could to stuff his all the way down my throat.

“There you go! Take it you fucking faggot!” George moaned. Pulling on his tie that he had used to bind my wrists while he spanked my ass. Stephanie giggling in the corner.

Charles grabbed my own tie dangling from my neck and lifted it up. Wrapping it around his hand. Jerking it. Using it like I leash to yank me up and down his cock.

I could hear George grunting from behind as he pounded me. I was beginning to learn the universal sound of a man orgasming first hand. His dick pulsed and throbbed inside my rectum and then erupted. The warmth filling my insides.

“Not done yet, Charles?” George asked as he pulled out and wiped his own brow with a handkerchief.

Charles said nothing, but I glanced up to see beads of sweat forming on his face. He abandoned the tie, grabbed me by both of my tiny pigtails, and started thrusting.

It is incredibly difficult to breathe when your esophagus is getting invaded by a big black monster. My nose was leaking many different fluids and mixing with my drool as it rained on to the floor. Charles is going to punish me for that later. I thought.

“On her face.” George commanded, apparently also understanding the universal sound Charles was making.

I could see the disdain flash across Charles’ face at the mess this would make on his carpet. But he said nothing. Just pulled the python from my throat and stroked.

I decided it would be a good idea to hold my mouth open and try to catch as much as I could to keep it off the carpet. The big black veiny cock was staring me in the face as I waited. Slack jawed.

I thought about all those girls in poorly edited porn videos that had to just sit there with their mouth open and wait an uncomfortably long time for the giant cock to pump jizz in their mouth.

I didn’t have to wait much longer. The first shot sent a line down from my forehead to my chin. The next one hit my mouth. I could tell Charles was painting my face with his cum in a way that would appease George, but also not get too much on his carpet.

The three shots that hit my cheeks and eyes next made me feel like a glazed donut.

I cracked open a cum covered eye to see George chuckling as he grabbed his briefcase and the door and left.

“Get it all in your mouth and not on my floor, Tommy.” Charles said, his voice a little deeper than usual. Like he was trying to reassert his dominance over me now that George was gone.

After using my finger to squeegee the cum into my mouth, I made to stand up from the desk. But Charles used one hand to force me back down.

“Ah ah ahhh!” He tisked. “Aren’t we forgetting something?”

Then he channeled his frustrations into my spankings.

*****

“Try to enjoy it,” Stephanie said as she sat on the floor next to me, playing on her phone. “This might be the last time you get to cum for a LONG time.”

I was on the floor of the women’s restroom again. Humping away in my wet and poopy diaper.

“Jesus, you stink.” Stephanie scoffed, wrinkling her nose “what did you have for lunch today?!”

Dave’s cum. I thought. I spent my lunch break under his desk again. He was insatiable. It was my 3rd time blowing him that day. “I’m not gay.” He reiterated several times, “I'm just really excited for my date with Stephanie.” He’d peruse her social media pages on his computer while I sucked him off.

I wonder if she’s texting him, I thought as I squished inside the disgusting mess of my diaper. She didn’t seem interested in me. I tried to enjoy my last chance to cum before being put in chastity. But all I could think about was how my life was spinning out of control as I spurted a weak load into my diaper.

“Changey time!” Steph said. Laughing.

*****

“And you’re sure you want to do this…?” My wife Amy asked incredulously. Holding up the small plastic cage that would be a prison for the foreseeable future.

We had just gotten back from the Sex Shop. The same one where I bought the lingerie and buttplug. Of course it had to be the same clerk to check us out too. I hoped and prayed that she wouldn’t say anything to my wife just then, but instead she just looked at the chastity cage, at me, my wife, then back at me, and just sort of nodded in a way that said “Yep. That makes sense…”

Now as Amy sat on our bed between my legs holding the tiny device, I contemplated telling her everything. My Boss is making me be his personal slut, my Secretary is the one that’s keeping me in diapers, and the guy who has a crush on her got 4 blowjobs from me today.

“Y-yes…” I said, visibly worried. I wanted to sound more confident and less terrified, but I failed miserably. “Me not cumming will give us a better chance to conceive a baby!”

She narrowed her eyes at me and I could sense how stupid it all sounded. But instead of arguing she just shrugged. Taking the ring and securing it around my balls and wiener. Then sliding the plastic tube around my shriveled member.

“Say bye bye to cumming for a whole month!” She said as she slid the tiny padlock between the ring and the tube.

And with one tiny *click*, the lock —and my fate— were sealed.