The Boss’ Baby Part 9 - The Shift

You know how when someone tells you not to think about something, that something immediately becomes all you can think about? Like, if I say ‘don’t think about the color Red’, which color immediately comes into your mind?

Well imagine that thing you’re not supposed to think about is cumming, but you have a constant reminder between your legs in the form of a cage that keeps you from doing just that.

After only a week in chastity, I felt like I was in a constant haze. Not being able to sleep because I wanted to cum so bad, and spending my days only making others cum.

Wishing it was me.

That being said, it was only my boss Charles I was having to pleasure this week. I guess Dave’s date with Stephanie went well, because he hadn’t called me into his office to blow him at all ever since.

Speaking of Stephanie, I needed to find her. I just made a very stinky, dirty mess, in my diaper and needed her to change me.

I prayed no one could smell me as I walked past their cubicles towards Stephanie’s desk at the front of the office. I’d be lying if I said I wasn’t aware of the whispers and rumors surrounding me in the office. I think people were slowly becoming aware that something was...off...about my constant squirming and the crinkly noises (and smells) coming from under my clothes.

I put that to the back of my mind as I approached Steph’s desk. But she wasn’t there. Maybe she was in Charles’ office?

I headed that way and knocked on the door. I could hear whimpering from inside. I saw someone peek through the blinds, assess it was me, and then the door opened.

I was not prepared for what I saw.

Dave was standing with his pants around his ankles. A soaking wet diaper around his waist. Bawling like a wittle baby. Dancing back and forth uncomfortably.

“I-i-ii’mm s-s-s-sssoo s-ss-sssorryyyy!!” He cried.

Stephanie was standing next to him, scolding him.

“You’re gonna be sorry after I'm done with you!” She growled menacingly. “Did you really think I would fuck you after just one date?! Is that why you forced yourself on me?! Is that why you tried shoving this into me?!” She grabbed the front of his wet diaper and squeezed.

Dave squealed much harder than would be expected from someone just grabbing a diapered crotch. He was crying and whimpering pathetically. It was a stark contrast from how he was last week when I was under his desk sucking his dick.

She kneed him hard in the crotch. He keeled over and fell to his knees. It was at this moment I noticed something green and leafy poking out the sides of his diaper.

“You’re fucking SCUM!” She barked, standing over him “but if you want to cum so bad, go ahead and do it. Right here. Right now. On the floor!”

“No!! NO!!! Please! Please no! I’ll do anything!! I’m sorry!! PLEASE!!” Dave begged. His face was panic stricken. I didn’t understand why he was so terrified of having to hump his diaper and cum, I'd do anything to do that right now after spending a week in chastity.

Stephanie ignored him. Walking behind him and digging her heel into his back until he was forced down flat onto the floor. With every rustle of his diaper Dave let out a squeal of pain.

“Cum bitch! It’ll be the last time you get to for a while!” Stephanie sniggered.

It was weird being on the viewing-end of someone else humping the floor in a diaper. All I could do was stand there awkwardly while Stephanie verbally degraded him and Charles chuckled from his desk. Eventually he seemed to notice me and gave a slight nod to his crotch.

I knew what that meant. I waddled over and knelt between my Boss’s legs. Unzipping his fly and pulling out his already throbbing cock. It was usually never this hard this quick, apparently he was enjoying Dave and Stephanie’s show.

All I could hear was Dave’s whining, crying, and pleading mixed with the rustling of his diaper as I slurped on Charles’ cock. Dave really sounded like quite the baby, I didn’t understand what the big deal was.

But I soon would.

Even through Dave’s crying I could deduce the sound of him about to cum, and with that, Charles’ own sounds came as his cock swelled in my mouth. His dick pumped jizz down my throat as I imagined Dave’s cock spurting a load in his diaper simultaneously.

“Changey time boys!” Stephanie said in her cheery Mommy voice. I wiped my mouth as I climbed out from under Charles’ desk and laid down next to Dave. He was glistening with sweat and tears.

“Oof Tommy!” Stephanie sneered, “you’re quite the wittle stinker aren’t you?!” I flushed in shame as she opened the tabs of my diaper, exposing the full load of poo mixed with my tiny caged cock. She cleaned me up, using the key on a chain around her neck to unlock my chastity device. I knew better than to get excited or expect anything. But that didn’t stop my freed cock from getting instantly hard. Once she had it clean she flicked it on the head painfully, making it retreat into a limp noodle before caging it back up again.

Instead of powdering me and putting me in a new diaper, she simply left me naked and caged as she shifted her attention to Dave.

“Did you like the addition I made to your diapy, wittle Davey?” She giggled as she opened his up. Finally I got to see what was inside that was making him so miserable. What was perplexing was that it ended up being just a bunch of leaves from some sort of plant.

But I couldn't help but notice how red and inflamed Dave’s cock was. He must have had some sort of allergy to the plant.

“Unfortunately I left fresh diapers in the car...” Stephanie said unconvincingly “guess you two babies will just have to wear each others diapurrs!!”

It was obvious this was planned all along as she pulled my still unwrapped poopy diaper over to Dave. “Lift up Davey! Time for the ‘ole switchapoo!!” She giggled as Dave whimpered. Squishing down on my soiled diaper and cringing as she wrapped the cold mush around him and taped it up tight.

“Your turn Tommy! Maybe you won’t be as whiney about the nettles as Davey was!”

As I lowered myself onto the sticky pile of leaves, I immediately understood Dave’s discomfort. It felt like I was being stung by a thousand tiny bees all over my ass and taint. I whimpered, pleading with her to reconsider as she lifted the front of the leaf-filled diaper.

“Please nooo” I begged. But she just laughed. Pulling it up and folding it over. It was the first time I was thankful to be wearing a cage, as it was less skin to come in contact with that devilish plant. My balls felt like they were on fire as she taped it tight around me. I wanted to scream. But I didn’t want the rest of the office—or the rest of the block—to hear.

“You will both report back to me for changes and spankies before you leave work today” she said matter of factly. Unfortunately that was still 6 hours away…

****

“Oh my goodness!” My wife Amy said as she opened up my diaper. “Wooks wike the wittle baby has quite the diapy rash!!”

The leaves were gone, but the inflammation from the nettles remained. Turns out having thousands of tiny little needles poking your pubic area all day can make you quite red down there. The spankings that Dave and I had to administer to each other while Charles and Stephanie watched made my ass even more blistered.

“Awww!! There there wittle baby!!” Amy cooed. She was really starting to embrace her motherly role. “Mommy knows just what to do to make it alllll better!”

She reached for a tube of lotion or cream and applied it to her hands.

The coolness of the cream and her touch made me feel instantly better. In fact, a little too much better…

“Awww! What’s wrong sweetie?! Is the wittle baby getting excited?!” She giggled. Noticing my cock pressing inside my tiny prison as she applied the cream to my balls.

I nodded and whimpered.

“Awww!! Do you want me to use this...?!” She asked as she fished the chain holding the key to my cage from between her perfect, perky tits. Dangling it tauntingly at me.

Again I nodded. “Please!! It’s been soo long...'' I sounded so pathetic. But I didn't care. I just wanted to cum.

She bit her bottom lip and considered. “Hmmm...nope!” She said, “We had a deal. One month of you not cumming! It’s only been a week!”

“B-b-but honey!! I really want to—mmmphh!“ but before I could say any more she had plopped a pacifier into my mouth.

“Shhh! That’s enough fussing out of you wittle baby! Now let’s get your diapy on before you leak all over the bed!”

To Be Continued