The Boss’s Baby Boy
by EPJ
3 Aug 2023 10565 readers Score 7.7 (45 votes) PDF Mobi ePub Txt
It was late in the day that my boss called me into his office. He had been going over payroll all day. I had been careful not to distract him and only take messages as he was so focused.
“Tim,” he calls me as I enter his office. “I have to make some tuff decisions.”
“Of course sir. But I am sure you’ll do what’s best for the company.”
He nods deep in thought. “What would you do to keep this job?”
“Anything sir.”
“Anything?” He raises an eyebrow.
“Of course sir. I need this job, my girlfriend just lost her job. So I need this one so we can afford rent and food.”
“I see, I have two options.” He sighs. “I have to either cut your pay in half or you become my private assistant and I can maintain your pay.”
I don’t even think about it. “I will do it sir.”
He hands me a stack of papers. “This will be your new contract.” I sign it without reading, I need the money I don’t care what it says. “You don’t want to review it first?” He asks.
“No sir. I need the pay.”
“I see what underwear are you wearing?”
I stand there shocked. “Excuse me, sir?”
“You heard me what underwear are you wearing?”
“Calvins sir”
“Take them off, does your wife have silk or lace underwear?”
“Yes sir.”
“I want you to wear those from now on.”
“But sir they won’t fit me.”
He glares at me “It’s either that or we go to the store now and get you diapers. Your choice but underwear is for men. You are no longer a man. You are my bitch. Understand?”
“Sir?”
“You will live with me from now on and do whatever I ask. Is that clear?”
“But my girlfriend-“
“I’m sure she will understand. She wants to keep her apartment doesn’t she?”
I sigh “Yes sir, she really likes our place.”
“Good so panties or diapers?”
Not wanting to wear my girlfriend’s underwear I sigh “I’ll take the diapers”
“Good, let’s go then.” He grabs his keys and leads me to his car “Tonight you’ll come with me. Tomorrow at lunch you’ll pack what you need from your place. Your car will stay here a work. Understood?”
“Yes sir.” I get into the passenger seat and he drives us to the store. He takes me in and picks out a package of diapers. After I pay for them he takes me to the bathroom.
“Drop your pants.” He tells me. I blush but do what he says. I try to go into a stall but he blocks my way. “You can stand or go on the changing table. Doesn’t matter to me. Stalls for men that don’t need diapers.”
“I don’t-“ I try to argue but he gives me a look and I shut up. I drop my pants revealing my small cock. He takes out a diaper and puts it on me. I pull back up my pants. I look in the mirror and can see my ass and groin puff out from the diaper in my slacks.
He gives me a large soda as we get back in the car. “We will be at my place in five minutes. I want that empty by the time we arrive.” He tells me. He starts to drive and I nurse my drink.
We arrive at his house and as soon as we enter the house “take off everything but the diaper.” He orders. “When we are home that’s all you wear.” I don’t even argue at this point. I’m not sure why but it feels like the right thing to do. He then cooks us dinner. While he puts on Cartoon Network for me. I am engrossed in the show. I’m not sure why I haven’t watched cartoons in years. It doesn’t even cross my mind that I should be cooking as his assistant. I just want to watch this weird boy and his magical yellow dog.
He calls me into the kitchen for dinner. I want to keep watching but after he calls me a second time I huff and turn it off. He made a steak dinner but mine is precut and on a Scooby Doo plate with a matching fork. I sit down and eat, he watches me as he cuts and eats his steak.
After dinner, he takes me to my room for the night. “Here is where you’ll be sleeping.” He tells me. The room is fine definitely a guest room.
“Where is the bathroom, sir? I want to use it before bed. The soda you gave me is really going through me.”
“You are wearing a diaper.” He points out. “Use that and if needed I’ll change you before bed.”
“It’s okay. Never mind.” I tell him. I’ll just look for a bathroom after he leaves. I think.
“Ok if that’s it have a good night.” He tells me before leaving. As he closes the door I hear the door lock.
“What the fuck?” I say aloud. I try to turn the knob but it won’t move. With no other option, I go to bed and hope I can hold it until morning. As I drift off I swear I hear him talking to me but I can’t make out what he is saying.
***
I wake up feeling wet I look down and see I pissed in my diaper while I slept. I for some reason wait for sir to come in. As if he knew, he has a fresh diaper.
“Can I go to the bathroom?” I ask, not sure why being a grown man I was more than capable to get up and go now the door was unlocked.
“Why, you have a diaper on.” He comments.
“But-“ I begin to protest but he gives me a look and I stop. He lays me on my back and swiftly changes my diaper. He hands me a coffee in a sippy cup. I feel it’s odd but like so many things I don’t question it. He picks out my clothes, which for the most part are normal, and dresses me as I drink my coffee.
“Ok, boy let’s go to work.” He tells me. I get up from the bed and follow him still nursing my cup. I finish it right as we arrive.
I start to go and unlock the bathroom to use it when he takes my keys out of my hands. “That’s the big boy potty.” He scrolls me.
“But I need to take a dump!” I complain.
“You have your diaper” he states in a matter-of-fact tone.
I then whine like a kid “No I don’t want to use it.”
He sighs and pulls out a plastic potty training toilet and sets it next to my desk. “Then you can use this.” For some reason, this made me very mad and I threw the potty.
“No!”
He grabs then and bends me over the desk and starts to spank me. I’m shocked and humiliated. Thankfully we are the first to arrive but I feel so embarrassed. I’m crying by the time he is done hitting my padded bottom. “You going to be a good boy?” I nod wiping my tears. “Good if you are a good boy then I’ll change your diaper at lunch.” I just nod and sit at my desk.
The day goes on as normal but I find some tasks I normally handle so easily difficult. And when I talk to my coworkers I forget large words and complex thoughts.
At lunch, I enter my boss’s office. At this point, I have used the diaper both to piss and I took a dump. He closes the blinds on the glass wall and changes me on the meeting table in his office. He then gives me a bunch of Dino nuggets and applesauce. I’m so excited but I don’t understand why, this is a meal one would pack for a small child.
When I finish eating I feel tired and he gives me a pair of headphones telling me to take a nap on the couch as he makes a call. I put on the headphones and I hear his voice.
“You want to be a baby. You are okay using diapers. The toilet is not for you. Daddy will care for you. You are a good baby. You love Daddy’s cock. You want to be daddy’s slutty baby boy.” This plays on a loop. I feel I have heard this recording before but can’t recall where. I feel myself fading and a new baby me emerging. I want to take off the headphones but I can’t.
“It’s time to go boy.” He says shaking me awake. I rub my eyes and he picks me up like one might a child.
“I can walk.” I mutter.
“It’s fine son. Just relax I got you.” He says as he carries me down to the car.
When we get home I expect to sleep in the same room as the night before. But instead, I’m led to another room. This one is staged as a nursery. There is a large crib, changing table, baby toys, and a rocking chair. He helps me strip down to my diaper and puts on the headphones again. He pulls the back of my diaper and pushes something into my ass. “You need to learn to use relax this should help.” He undresses and puts me in his lap on the rocking chair.
I instinctively start to suck on his chest as he rocks. My stomach rumbles and I let out a fart. He rubs my back pushing me more into him. I feel his hard cock under my diaper. My stomach lurks again and my bowels unleash into the diaper. I moan as it feels amazing to release my wet shit. I feel him adjust his cock into my diaper. It slides along my crack. The wet shit dripping on his balls. He fucks my shitty diaper until cumming. “Soon we will start training you to take cock.” He kisses my forehead and places me in the crib before turning out the lights. The headphones still on repeat.
***
One Month Later
My girlfriend comes into my boss’s office. I sit in the corner playing with some dinosaurs in my diaper. Who she is completely escapes me. My daddy hands her an envelope. “As promised five years worth of his salary.”
He takes the envelope and checks the contents before looking over at me. “I knew he wasn’t a man.”
“What do you plan to do now?” My daddy asks.
“Not sure, probably go on a nice vacation. Then find another man.” She tells him.
“Well, if the new one isn’t much a of man. I can help you with that. There is an auction that happens every few months. The profits make that envelope look like chump change.”
She holds the envelope and smiles. “Maybe, I’ll be in touch.”
The End?
Note for the author:
Hi Everyone,
I hope you enjoyed this short story. Right now I don't have any plans for little Timmy and his Daddy moving forward but that could change. Let me know what you think should Timmy’s story continue? Maybe he and his Daddy come to Master’s estate for a playdate with One? Would love to hear your thoughts.
EPJ