Daily Free-Write April 19, 2021: Diaper Training My Boyfriend Pt. 11 (Patreon)

Continuation of April 5, 2021, “Diaper Training My Boyfriend Pt. 10”

I spent the day texting back and forth all day getting updates from Tommy's new babysitter as I went about my business. I had an important meeting with a big wine distributor, and a full day after that filling in for Melinda at the winery, but every message seemed to make the day go by a little easier.

First, they cuddled up to cartoons and she ambushed him, holding him in her lap and buzzing his diaper til he squirted. After, she said, he seemed to settle down a bit, which was good because she wanted to make sure he rested and took in lots of fluid. I smiled to myself when she complained that he was a fussy eater, but was apparently able to get a selfie of Tommy pouting and blushing while being fed pedialyte through a bottle.

She had many things to say but most of all, she just couldn't get over how damn cute he was.

"How's the little boy?" I texted, a little after noon.

"Cute as a button. Take a look." She sent me a picture of a sleeping Tommy snuggled up in her lap.

"I just put him down for his nap," she texted. "He fussed but a little visit from Mr. Buzz Buzz calmed him right down. He made the most adorable noises when he came in his pampers, then he went all limp in my lap and went right to sleep. "

"Good trick! I'll have to remember that. He give you any trouble?"

"Oh, he keeps whining about wanting to use the potty, but it's nothing I can't handle."

"Good, don't let him push you around. If he tires, call me and I'll set him straight."

I didn't expect her to call, but later that day as I was wrapping things up in the fields, my phone went off. I excused myself and started walking back toward the road as I picked up the phone.

"Hey, what's up, Cassie? Everything okay?"

"I'm fine, we're having a little tantrum here is all. Tommy demands to talk to Daddy."

"Oh, he does, does he?"

"Oh yeah…hold on…" her voice got a little more distant as she went to speak to Tommy. "No sweetie, you don’t use the potty anymore."

"But I-"

"Shhhh.... you’re just not ready for that, sweetheart. You go in your diapers now."

"But-"

"No more buts. Now you use those diapers like a good little boy."

"Hnnn I…"

Cassie returned to speaking with me. "Well, I think that argument just ended. He's holding his crotch like he's trying to stop his peepee, but I see someone's diapee getting a lot bigger all of the sudden. Oh! That is warm."

"You tell Tommy Daddy says no more asking to use the potty or he's going to get a red bottom when I get home, or you can give it to him."

"Tommy… your Daddy said no more asking for the potty or you're getting a spanking from BOTH of us. Got it? No sweetie, you don’t need a change yet. Your diaper can hold a lot more… I'm sorry to waste your time on this," she said, though her voice sounded anything but. I suspected this call was simply to make a point for our little Tommy.

"It's okay, he's just getting adjusted. This is good for him."

"Well, we can all do our part to help little Tommy feel comfy being himself. That's right, little Tommy! I'm talking about you!"

I could hear Tommy's annoyed voice. "Ah! Hey! knock it off! Don't boop my nose!"

"Aww, Mr. Fussy is back. Mama Cass knows how to take care of that! Cyrus, I'm gonna have to let you go. This little one is gettin' ornery again."

I heard the click of the buzzer go on before she hung up and I chuckled. She must have buzzed him a dozen times by the time I got home.

When I got home, I was almost afraid what I was going to walk into. But I came in and there was no broken furniture, no big mess left by an angry toddler. In fact, when I came in, Cassie got up holding Tommy's hand and he followed where she led him, meek as a lamb, coming right up to me.

"Okay Tommy. Remember what we practiced. What do we say?"

"Hi, Daddy. Welcome home!" he said, with a shy smile.

"And then?" she asked, expectantly.

He came up and gave me a big hug and kiss on the cheek.

"Thank you for being my Daddy and helpin me learn how to be a good boy."

Cassie clapped and Tommy blushed deep red as she praised him. "That was so good, Tommy!"

"Aww, thank you sweetie!" I said, Ruffling his hair and giving him a kiss on the forehead. "It looks like you're feeling better too!"

"He is," chimed Cassie. "The little boy just needed a little TLC, isn't that right, sweetie?"

"Yes, ma'am," he said, brushing his hair back behind his ear and looking so adorable and shy.

I couldn't believe how obedient he was acting. Just to test him, I turned him around and stuck my two fingers in the leghole of his diaper. He didn't so much as flinch, just stood there and took it.

"Looks like he's dry," I declared.

"Just changed him," she said, smiling proudly.

I handed Tommy back his cellphone and sent him off with a pat on the butt, then I pulled out my own.

"Thanks for coming, Cassie. You really saved my bacon. Can I pay you with Pear Pay?"

"Yeah, sure. Heck, I'd do it for free for a cutie like him! I haven't had this much fun in ages! And after all, he is my friend, and he did need looking after with that nasty hangover, poor dear."

"Well, maybe we can work something out tomorrow at game night, but for now I'm definitely paying you. How did you get him to be so good?"

She laughed. "I have my ways. But those will be my secret. A little incentive to keep hiring me!"

I laughed. "You've done more than enough to convince me of that. Okay, woman. Keep your secrets. And thank you." I said, giving her a big hug.

"So, see you tomorrow?" she asked.

"Tomorrow. Game night. Be there or be square!" I said.

She left and I set off to find my little guy. I found him rubbing his little diaper in the bedroom. He made a surprised little noise when he saw me.

"Uh oh. Is my cute little boyfriend rubbing his little wee-wee without permission like a naughty boy?"

"C-can't you knock?" he asked.

"Now that doesn't sound like the polite boy who greeted me at the door."

"Cyrus-" he began.

"It's Daddy now, remember?"

He gave me an exasperated sigh. "Daddy... we need to talk."

"We do?" I asked, sitting next to him and putting my hand on his thigh. My boy looked so adorable sitting there in just a diaper and Ninja Lizards t-shirt.

"Yes, we do. You can't have Cassie come to babysit me again."

"Oh, I can't?" I asked, smirking, and running my hand up his leg. "And why is that? Didn't you have fun today? I saw you were rubbing your… diaper." I  gave his package a little squeeze through the material every time I said the word diaper. "And I know how many times you came in your diaper today… That tells me you must really like being babysat..."

I could feel his pee-pee responding through his padding even as he shook his head.

"No way, Daddy. Mama Cass treats me like a little kid. She's even worse than you!"

I chuckled at his use of the word 'Mama'. Ironically, his denial sounded just like a little kid.

"I'm serious," he said, slapping my thigh. "She uses baby talk, she doesn't let me feed myself even when I tell her I don't need her help… She had me drinking out of a bottle for gosh sakes."

"Awww…. I'm sorry little guy," I said in a mocking tone, "that sounds really hard. But I don't get it. If you're such a big boy, why did you let her treat you like  a baby?"

"L-let her? What do you mean? I didn't have a choice!"

"You didn't have a choice but to listen to a woman who is half my size? Really?" I chuckled.

"Come on, Daddy. You know that's not allowed," he said, crossing his arms and getting all huffy.

"And so do you. And do you know why? Because you're a good little boy. Not a man," I said, speaking softly but firmly as I looked him in the eye. "And you know exactly how you should behave."

I pulled down my pants and hooked the waistband of my silk boxers under my balls so he could see me getting hard while he sat there next to me trapped in his diaper. He whimpered.

"See the difference between you and me, Tommy? A real man wouldn't let another man shave his little peepee and throw out his undies… A real man wouldn't beg another man to put him back in diapers for good…"

I began to run my fingers around round the leg holes of his diaper and over the front, teasing him as I listed every way in which he showed he was a baby.

"A real man wouldn't go around calling adults Mommy and Daddy… and let them feed him baby bottles… A real man wouldn't let another man tell him he needs to make all his stickies right… here…" I gave his little package a squeeze through the padding.

"So what does that make you?"

"D-daddy…I- unh… I'm not a baby..." he moaned.

"Really? Then why do you have a baby pee-pee? A baby pee-pee that can't even stop itself from piddling all over the floor when those diapees come off…"

"Th-that's not fair…" he whispered.

I stuck my nose into the leg of his pissy pampers and sniffed, jacking my cock to full mast. "Mmm… boy piss... You've just gotten changed and you're already wet. What does that make you, little boy?"

"Daddy, I…"

"Say it, Tommy," I said, sliding my fingers in through the legholes of his diapers and playing with his cock. "Say 'I'm just an incontinent little pants piddler…'

His face contorted as he tried to resist. I knew he was already losing the battle. His hips were thrusting as I teased his little dicklet. "I-I'm… an incontinent little pants  piddler…"

"That's right… doesn't that feel good to admit it out loud, little boy? I'll bet that feels so good."

He didn't respond, he just went redder and his breathing got more ragged as I brought him closer to the edge.

"You need this, little Tommy. And there's nothing wrong with enjoying it, and getting what you need, is there?"

"N… no…," he mumbled, doing his best imitation of a ripe tomato.

"So tell me one more time… are you a man… or a little boy?"

"L-little boy, he said, breathlessy…

"That's right. So there's no more hiding it, little boy. From now on you're going to be a good boy, let Daddy make all the important decisions, and do whatever Daddy and the other grown ups tell you from now on. Do that and, and I promise you it'll be the best decision you ever made…" I echoed the words I said when he first came into my life.

"Yes, Daddy," he said, nodding his head in understanding.

"Good boy. Good boy," I said, taking him past the tipping point to a screaming orgasm in his diaper. "It feels so good to obey Daddy, and do what he says… so good to give in and be a baby."

I could hardly tell if he heard me with all the shuddering and moaning he was doing. Eventually, his orgasm subsided to the occasional aftershock and I spoke.

"I trust we'll never have to have this conversation again?"

"No, Daddy," he said, quietly.

"Good. Now suck Daddy's baba. You got Daddy all horny and he's got a lot of cream for his baby boy."