Daily Free-Write March 25, 2020

Continuation of March 23, 2020, “Diaper Training My Boyfriend Pt. 8”

“We’re sticking with grape juice from now on, kid,” I said as I dragged Tommy into the house and up to the bedroom with Carter’s help. He had been kind enough to park my car in the garage at the winery, and then take me home. Tommy was woken up to leave, but aside from a very brief protest about going out without pants on, he obediently started to get up before promptly falling right back asleep so that we had to carry him to the car and then up to bed once more at our place.

Carter saw the cartoon t-shirt and diaper still waiting on the bed before I pulled back the covers and we laid him down.

“You sure do take this Daddy thing seriously, Boss.”

I already had my hand on the front of Tommy’s diaper to see how wet it was when he said this (it was warm by the way).

“What tipped you off?”

“Well, there’s his enormous diapers, for one. And then there’s little things like these clothes. Oh, and the fact that he calls you Daddy. Not that it’s any of my business. He’s cute as all heck like that, to be honest.”

“Well, then maybe you can see a little of what I see. I didn’t know about his diapers when I first met him and believe me I was as surprised as anyone to find out. Now, I’m just helping him accept it and having some fun with it along the way.

“Well, that’s pretty sweet, boss. You got a tissue? I think I’m going to cry…”

“Get outta here!” I said, swiping at the air. “I oughtta keep the bonus just for that.”

“Hey! I’m just teasin’, boss. Just teasin’! Get some rest, and try to give the kid some water. He’s gonna have a mean hangover in the morning.”

*****

In the morning, I woke next to a groaning Tommy.

“Oh boy. Is my little boy alright?”

“Ugh… I’ll never drink again.”

“Damn right you’ll never drink again. From now on, it’s grape juice and apple juice instead of beer or wine, and you can forget about hard liquor.”

“Unh… don’t want it,” he groaned. “Did last night really happen, or was that just a dream?”

“Uh… which part?”

“The part where I lost my pants and got diapered by a bear?”

“Oh yeah, that. I mean you got most of the details correct. You got trashed, decided to do your best imitation of a waterfall all over the chair and the flagstone below, and Melinda had to diaper you up and put you down til we could go home.”

“Oh god…,” he said, holding his head in his hands. “I’ve never been more embarrassed in my life.”

“That’s what you always say,” I said, rolling my eyes. “Here, drink this. It’s medicine”

I handed him a glass of fizzy water, which he downed, grimacing at the bitter flavor.

“Yeah, well, when I’m with you, it’s nearly always true.” He went to get up but I held him down with a hand on his shoulder.

“And just where do you think you’re going, baby boy?”

“I have to get ready for work,” he said.

“Yeah, no. You’re still hung over, baby boy. You need to recover.”

“Yeah, well a hangover isn’t exactly an excusable absence,” he said, wincing as he tried to get up again. I pushed him down onto his back and held him there.

“I’ll tell you what, baby boy. You mess those diapers and we’ll get you changed, and then I’ll think about letting you go to work.

“M-mess my… wait, we’re not still doing that, are we? I can still use the potty, Daddy! Come on!”

I chuckled a bit at his use of words like Potty and Daddy. He was beginning to sound more like the little boy he was and he didn’t even know it.

“You begged me to keep you in diapers and that’s exactly what I intend to do. You’re going to use your diapers and you’re going to like it. And speaking of which, there’s a little daily maintenance we have to take care of. “I picked up the buzzy wand from the bed and held it up. “We gotta train you to feel good about diapers, especially when you use them like you should.”

He looked at the wand like it would bite him. “C-can’t I wear undies at least some of the time? Pleeeeease? I’ll be good, I promise! I’ll even ask permission when I have to use the potty!”

“No can do, kiddo.  Remember this is about developing…”

“Yeah yeah, good habits,” he said, crossing his arms and huffing.

“Aww someone’s a little grumpy pants today. I know what’ll cheer you up – a good dose of cum. Come suck daddy’s dick. That oughtta keep you quiet until you poop your pampers like a proper baby.”

I fished my cock out and stuck my nose between the back of his thigh and the diaper to get started. I sniffed long and deep, taking in the scent of baby powder and boy piss while my other hand plumped up my fat sausage nicely.

When it was nice and plump, I pulled away and looked down to find a nice bead of precum getting ready to roll down. I laid my cockhead in his mouth and he took it in, suckling eagerly while I brought the wand to the front of his diaper. I began to massage his tummy which caused him to squirm and whine, but with a mouthful of cock, there was little he could say. Shortly thereafter, He grunted and filled the back of his pampers, shuttering and whining as if he was having an orgasm while doing it. This, of course set me off and I could feel that I wouldn’t last much longer.

“Did you poop your Pampers, Tommy? Huh? Did the little baby dump in his diapees?”

Tommy just whined and nodded, turning bright red.

“That’s.. hhhh…. Right…. Baby Tommy… unh… You’re a good boy and you you’re your pampers when Daddy tells you to. You deserve a treat… don’t you think?”

He nodded.

“Yeah… fuck… Here it comes, baby boy! Drink up all Daddy’s milkies for me baby! Ahhhhhhh fuckkkkkkkk!”

I gritted my eyes shut and hunched over driving my cock into the back of his throat as my body forced out every ounce of liquid in my balls and prostate, sending it straight down Tommy’s throat. Where it all came from, I hadn’t a clue. Not after yesterday’s marathon whack-off session. Forcing my pulsing rod down his throat with the wand pressed firmly against his diaper seemed to be all it took to send him into a shuddering orgasm too. I pulled out, so I could hear his moans of pleasure and Daahaaahaaaddeeeeee. That’s what I loved to hear.

“Good boy, making cummies in your messy diapers. It must mean you really like being kept in them and making poopies, huh Tommy?”

Tommy shook his head.

“Are you feeling any better, baby boy?”

He nodded. “Yes, Daddy, but may I please get out of this messy diaper?”

“Yes, little boy. I’ll help you. Stay there.”

He looked at me questioningly, but when I returned with the changing pad and the wipes he looked concerned. “Shouldn’t I take it off in the shower?” he asked.

I shook my head.

“I said I’m not changing you in the bathroom, Tommy, and I meant it.”

I opened up the diaper, using the front to wipe away as much of the muck as I could, then got to work with the wipes. Once he was completely clean, I sent him off to the shower, following behind closely. He was hiding it well but I could tell he still wasn’t feeling one hundred percent as I soaped him up.

For one, he was a little bit paler than usual, and he didn’t have his normal goofy humor. I worried about sending him to work, but on the other hand, I wouldn’t be able to stay home that day because I had to fill in for Melinda, who was enjoying some paid time off thanks to her disturbingly good talent for extortion.

Tommy seemed to want to work, and Nia could always keep tabs on him and send him home if need be. If he stayed I would need a babysitter at least. And who would be willing to look after the little guy?

By the time I shut off the water, I had come to a decision.