Daily Free-Write April 5, 2020: Diaper Training My Boyfriend Pt. 10

Continuation of March 25, 2021, “Diaper Training My Boyfriend Pt. 9”

I shut off the water and pronounced Tommy clean and ready for the day.

“Alright, Tommy. Let’s get you padded and dressed,” I said, giving his bum a light smack and sending him into the bedroom with his towel covering his privates just in case he had a leak.

I started the change by putting an extra thick ‘soggy froggies’ diaper under Tommy’s butt and powdering him up. Next, I brought the diaper up between his legs. Even though his cheeks were tinged with pink, I could see him visibly relax as he felt the familiar sensation of a crinkly diaper hugging his bum. But when I stepped away without taping the diapers up and grabbed my phone, his expression turned to one of confusion.

“H-hey, wait! Aren’t you gonna finish?” he asked.

I held up my finger.

“Hold on, baby boy. I have to make a phone call really quick... And don’t even think about touching that diaper, mister.” I added, as I saw him reaching down to tape it up himself. “Those hands stay above your waist at home.”

He groaned and laid back down on the bed, resigned to waiting.

I dialed out and brought the phone to my ear.

“Hi, Nia. Yeah, it’s me, Tommy’s Daddy.”

“Oh my god…” said Tommy, putting his hands over his face. “You did not just call yourself that to my manager!”

“Hush little one,” I said, not bothering to cover the mic. “Or do I need to put in your pacifier? …Sorry about that Nia. This one is business, I’m afraid. Our little Tommy is having some tummy troubles this morning and he needs to take the day off.”

“Hehe, you got me,” I replied, rubbing the back of my head. “I’m gonna have to take away his big boy drinks and stick to grape juice and apple juice from now on. So, do you think you can get him covered? You’ll cover his shift if I cover his butt? Deal. Yeah, we’re still on for game night tomorrow, and he should be back to work by then. Maybe you can give him a ride here? Thanks a million,” I said, grinning to myself as the call ended. “You’re in the clear, Tommy. Nia said to say hi.”

“I can work,” he said, crossing his arms and huffing.

“Alright, that’s it. You’re getting the pacifier.” I grabbed his hair pulled his head forward to meet my cock, which had plumped up nicely. I glared down at him and he obediently accepted it into his mouth.  “Now you keep that in there or you’re going to have one very sore behind.”

“Yeth, Daddy,” he said, looking me in the eyes as his cheeks burned red. “Can I haff my diapow taped up now?”

“Hold on just a sec, baby boy. I have one more call to make.” I dialed out again and after a few rings, the phone picked up. “Hey, Cassie! Hi, good, good.”

“Catthie?!” Tommy squeaked, his eyes growing wide in alarm. I put my finger to my lips and continued with my call. “Cassie, do you remember what you said the other day after game night? Yeah, well, Tommy is sick with a hangover and I need to go to an important meeting out of town so… yeah, I need a babysitter.”

I pulled the phone away as her excited voice was loud enough to hear even at a distance. I gripped the back of Tommy’s head to stop him from shaking it ‘no’ and thrust forward lightly, burying my cock deeper in his throat and silence his whines. After couple more thrusts, I continued,

“Yes, I’m being totally serious now. I’m getting dressed to go as we speak. How soon can you be here? Hello?”

“She said she’s on her way,” I said, shrugging to myself. I unplugged his mouth and set my phone aside to tape up his diaper nice and snug. “Did you hear her? She sounded really excited to babysit you, Tommy.”

“No…” he groaned. “You can’t!”

“Oh, can’t I, baby boy?” I asked, grinning down at him as I held up his vintage Ninja Lizards shirt. “Because from where I’m standing, I see two options for you. Cassie comes and babysits my cute little boyfriend, or Cassie comes and babysits my cute little boyfriend with a red bottom.

“Are you getting a hard-on from this?” he asked. “Gods. You’re the worst.”

“Love you too, baby boy.” I said with a smug grin.

Despite his complaints he sat up, lifting up his arms for the shirt.

I beamed. “That’s my good boy.”

I slid the shirt down over his arms and tugged it over his head. Then I stepped back and admired my handiwork. “Perfect. You’re all dressed for the day!”

He looked down at himself in his green Ninja Lizards shirt and matching green diaper and back at me. “You’re kidding, right?”

“Not even a little bit,” I said, patting him on the head. “It’ll be easier for her to check your diapers without pants.”

“Check my diapers?!”

“You didn’t think you were going to get to change them yourself, did you love? That’s just a work rule – for now at least. Now hurry up and let’s get something in your tummy… unless you want Cassie to feed you herself.”

Tommy didn’t need to be asked twice. He hopped up off the bed, but then stopped and held his stomach, looking slightly dizzy from the sudden movement.

“Take it slow, baby boy,” I said. “The aspir-seltzer will help with the sickies, but you still need to rest and stay hydrated.”

I helped him to the living room and soon he was eating his oatmeal at the dining/game table like a good boy. The bell rang just as he finished and he looked over, clearly nervous. He instinctively hunched over the table, in a futile attempt to protect himself from being seen in diapers by his best friend.

“Don’t move a muscle, baby boy,” I said, holding up a finger. “I’ll be right back.”

I hustled over to open the front door. Cassie stood there, loaded up with bags and wearing a big bright smile on her face.

“Where is he? Where’s Tommy?” She asked, handing the bags off to me and pushing her way inside.

“Come on in, I guess,” I said with a bemused smile as she rounded the corner and let out a squeal of excitement. I smiled as I shut the door and came around the corner to see her cooing over a confused Tommy, pinching his cheek and gushing about how cute he was. He didn’t even have time to be bashful with her fussing over him.

“I can’t believe you’ve been keeping this cutie to yourself this whole time,” she said, looking at me in mock scorn as she hugged his head to her body.

He let out a groan and held his stomach.

“Careful with him. He’s fragile. He had a little too much funny grape juice last night and he’s still recovering.”

“Aww, I’m sorry sweetie. Did Daddy feed you too much happy juice? Don’t worry, Mama Cass will make you chicken soup later and we can watch Ninja Lizards.”

“Wow. I guess you’re known as the group mom for a reason!” I said as she took out a cloth from the diaper bag slung over her shoulder and wiped his face.

“Damn straight!” she said, with a smirk. “Hold still, Tommy!” she said, licking the cloth and scrubbing his cheek.

“Staawwwp…” whined Tommy, but Cassie was having none of it.

His diapers are in the bedroom closet. They won’t be hard to spot. You can ask him to show you his favorites when he needs a change.”

She grinned and looked at him. He was squirming like a worm in a hook.

“Feel free to put him down for a nap when he gets cranky. He is to listen to you and do whatever you say.” I looked at him pointedly as I said these last words.

“Any special rules I should know about?”

“Yes. He is not allowed in the bathroom without an adult and not allowed to use the potty. The toilets have locks on them, here’s the magnet key.” I took my keys out of my pocket and unclipped the magnet fob, handing it to Cassie.

“Got it,” she said with a giggling as she snuck a peek below the table. “Guess the little guy isn’t ready for potty training, huh?”

“Nope. And he never will be.”

“Oh, come on,” said Tommy.

“Oh, that reminds me,” I said. “I use the buzzy wand as part of his daily maintenance. We’re trying to help him develop positive feelings toward his diapers, since he’s going to be in them full time from now on.”

“Oh, you are, are you?” she said grinning at him.

“Don’t even think about it,” he said, starring daggers at us.

“I think it’s cute that you think you have a choice,” she quipped back, and he buried his hands in his face, turning bright red. He was so embarrassed he was shaking.

“Well, looks like you’ve got things mostly covered. You know the house well enough already, I said, checking my watch. “Just make sure he drinks plenty of fluids and call me if you need anything.”

“I’ve got a bottle with his name on it,” she said, with a self-satisfied grin.

“A bottle?! I don’t drink from bottles.”

“You do when I’m in charge,” she said.

“Daddy! Tell her I don’t drink from bottles!”

“You do what your babysitter tells you, sweetie. She’s in charge. I have to head out if I’m going to make that meeting. Do you have any other questions?”

“Nope, I’ll take it from here,” she said, then turned to my infantilized boyfriend.

“We’re going to have so much fun, little Tommy. I’ve brought all kinds of toys and games, and coloring books, and crayons, and all sorts of other fun stuff for us to do! Now why don’t we go and wash your hands at the sink and get you some juice. How does that sound?”

“I’m not two you know,” he said, his cheeks burning as she pulled him over to the sink.

“Of course not. You’re a big boy!” she said, giggling as if it were some kind of joke.

“I am a big boy!” he protested, as she thrust his hands under the water and rubbed them together to build up some suds.

“I think Mr. Grumpy pants is gonna need some cuddle time and a visit from Mr. Buzz Buzz soon,” she replied in a cheerful voice. “Right after I give you your baba.”

I left feeling confident that I had chosen a good babysitter for my bashful boyfriend. Still, she seemed a little too excited about this babysitting gig for it to be mere curiosity or adoration. I’d have to ask her about that later.