Daily Free-Write March 21, 2020

Continuation of March 9, 2020, "Diaper Training my Boyfriend Pt. 5"

I was glad I remembered the anniversary by some stroke of luck. I had never been into things like anniversaries but for tommy he was all about that sort of thing, and I was sure it would be on his mind, when he wasn’t totally freaking about about who might know about his little potty problem. The latter could be solved by gradually introducing his diapers to those around him, while at the same time desensitizing him to that exposure. He needed to understand that he really needed them, and I was sure others would be quick to accept that as well. If not, it wouldn’t be hard to prove.

I readied myself to pick my little barista up from work, the main task of which was to repack his diaper bag. I pulled out a soaked diaper from the bag. It was bright yellow, swollen, and very squishy. I was glad to see it had been well used. I was also pleased to see that he had used up all the stuffers in the bag. I made sure to grab the thickest diapers and stuffers we had and put them in the bag since we were going to be drinking. Wouldn’t want my little one to have a leak too soon.

The sun was getting lower in the sky by the time I turned up at the coffee shop to pick up Tommy. I wondered how soggy his diaper would be after work. I thought about him crinkling around the café and wetting himself in the middle of a bustling shop. My cock started to chub up once more, despite having achieved a ridiculous number of orgasms since I stopped by to get him his diaper supplies. Why it turned me on so much to see my boyfriend helplessly diapered, I couldn’t say. All I knew was it did it for me – and it was clear it did it for him too. Why question it?

I had made sure to arrive a little before the end of the shift so I could come in and make it more obvious that Daddy was picking up his little boy from work.

I walked in to the shop and waved at the cutie behind the counter – my cutie.

Some of his coworkers seemed to recognize me, because they had their eyes glued on me the moment I walked in. One ended up overflowing the coffee cup he was filling as he stared, only to stop when another employee, also staring, elbowed him in the ribs.

“Can I help you, sir?” asked a tall blonde woman by the coffee pickup counter.

“Oh no, I’m just here to pick up my little chipmunk. I guess I’m a little early.”

“Your little, chip-” she looked around, confused about what I was talking about.

“Oh there he is, behind the register.”

She zeroed in on him immediately and looked back to me, turning slightly pink as she stifled a giggle.

“I’ll… I’ll let your, hehe, little chipmunk know you’re here.”

“Just tell him his papa bear has come to pick him up.”

She was practically hyperventilating to keep from laughing out loud, and had to just bite her lip and nod as she turned around and walked toward my beautiful boyfriend. She tapped him on the shoulder, and pointed my way, saying something I couldn’t hear.

I waved toward him, and he waved back, returning to his conversation with the customer before doing a double take, his mouth hanging open. He quickly shook himself out of it and finished handing the older woman in front of him her card back, but I could already see the red rising in his cheeks as whatever she said sunk in.

Nia walked over, wiping her hands on her apron and she smiing at me.

“So, has my baby boy been staying out of trouble?” I asked with a grin.

“Little Tommy? Oh, sure. He’s pretty easy to keep in line. Especially since I warned him that I’ll report his behavior to his Daddy if he doesn’t behave.” She gave me a toothy grin. “He knows to be good. Not like some people who work here,” she said, glaring over at Jay Jay, who once again had abandoned his cleaning duties to drool over my red Aston Martin.

“JayJay! Back to work! You have 5 minutes to finish those windows or I’ll have you on toilet duty tomorrow!”

He jumped, as if startled, and started wiping the windows at double speed.

Soon, Tommy disappeared and came back out sans-apron.

“Ready to go, kiddo?” I asked.

“Oh no, not you with her again. I need to keep you two apart. There’s no telling what the two of you are planning,” he said, pulling me away from the counter.

“Don’t worry, sweetie,” she said, “all for your own good, we promise!”

“Yeah, kiddo. We’re just looking out for our little Tommy. Don’t worry your pretty little head over it, love.”

Before we were too far, I called out to Nia, “See you this Wednesday for Game Night!”

“Wouldn’t miss it for the world,” she said.

As soon as we got out of the store, I smacked his butt and wagged my finger at him.

“That was very rude, little boy,” I said. “You shouldn’t tell the grown-ups what to do. This was the first time, so I’m letting you off with a warning, but do it again and you’ll be over my knee with your pants around your ankles. I don’t care if it’s at work or anywhere. Got me?”

“Aww geez, Cyrus, come on,” he said rolling his eyes.

“Cyrus huh? Okay, you must really want this, then.” I reached for his pants, and he scooted away from me.

“I don’t know where you think you’re running, baby boy. You’re still gonna have to come over here and get in the car.”

He continued to back off until he bumped into a slumped over Jay Jay, checking his watch and looking dejected.

“Oh! Sorry, man,” said Tommy. Then he noticed Jay Jay’s body language when he barely reacted, too lost in his own troubled thoughts.  “Uh, hey…. What’s wrong?”

“I don’t’ know if I’m gonna make it at this job, man. I keep getting yelled at by Nia. And I missed my bus, so I guess I’ll have to take a cab… so much for my daily earnings…”

“Hey,” I said, jerking my thumb back toward my convertible. “Want a ride?”

His eyes lit up, and he broke into a big smile. “Hell yeah!”

“Jay-Jay, right?” I asked.

“Yes, sir!” he said, shaking my hand and smiling. I patted him on the back and led him over to the passenger’s seat.

“Get on in! Little Tommy can sit in the back. It’s safter for boys his age anyway.”

The comment sailed right over Jay-Jay’s head as he was too enthralled by the interior of the car. He hadn’t wasted one second getting into the seat and buckling up, almost like he was afraid I’d change my mind.

Tommy glared at me, annoyed.

“Aww, you okay, love? Do you want a change in the back seat before we leave?”

Blushing, he shook his head. “Oh god, please no…”

“Then hop in,” I said. “We’ve got places to go!”

I drove Jay-Jay to his place, which was a bit out of the way, and then dropped him off. He was having the time of his life on his ride-along, and I was more than happy to punch up the acceleration just for a little extra thrill.

“Hey, kid,” I said, even though I wasn’t much older than him. “You’ll do just fine working there. All you need is a little guidance. I can set you up with a friend of mine, if you like. I think he could really help you.”

“Uh, sure!” he said, shrugging. I handed him a business card for a Daddy friend of mine who had been looking for a boy for some time.

“If you take this, you have to promise you’ll call him. I only have one of these to give out, and this is not to be shared with anyone.”

“Oh, shit! Yeah, okay,” he said, suddenly looking much more interested. “And don’t try looking him up online. You won’t find anything,” I added, with a smirk. I had him hook line and sinker. By this time next month, he’d be a model employee, probably with slightly poofier pants, too.

After dropping him off, I headed straight for the winery.

As soon as he was out of sight, Tommy spoke up.

“Daddy?”

“Yes, love?”

“Can I bring my own diapers to work from now on?”

I feigned reluctance.

“I don’t know Tommy, that’s a big responsibility.”

“Oh come on. I can do it, You know I can. Pleeeease?”

I smiled. Today, Tommy had to rely on me to bring diaper changes, so of course he would be eager to bring his own diapers now. That was the whole goal of today, and I got there by going to a further extreme to make it seem like a compromise in comparison.

“Well… okay. But only if you agree to check in before you have a change, so I know what’s going on. Deal?”

“Deal,” he said, crossing his arms and smiling smugly. He was so sure he had won, and it was really quite adorable. He had no idea what his gullibility did for my libido, thanks to the seat blocking his view of my crotch.

“Wait… this isn’t the way home,” said Tommy, realizing we were taking a different route than normal.

“I know, sweetie. I’m taking you somewhere very special today.”

“Special?”

“Yes, sweet pea. Remember when we meet a year ago?”

“Oh my god. I can’t believe I forgot it. It’s our anniversary!”

That’s right, love. And do you remember I told you to trust me? And you did? Well, I think that deserves something very special to remind you how good a decision you made.”

“Awww…. Daddyyyyyyy!” he said, blushing and covering his face. “This is so sweet!”

“Anything for you, pumpkin,” I said, unable to stifle my creeping grin. This would be a very special treat for me as well.