Daily Free-Write March 22, 2020

Continuation of Daily Free-Write, March 21, 2020: “Diaper Training my Boyfriend Pt. 6”

“Do you want me to pull over and change you in the back seat?” I asked, as we drove the winding road to the winery.

“No,” he said. “But I’m really soggy. My diaper is all swollen and squishy,” he said, wiggling around in his seat.

“I can tell, baby boy. I could spot a diaper bulge like that a mile away!”

I glanced into the rearview to catch him looking down between his legs.

“Oh my gosh, it’s so obvious! I felt so self-conscious at work today. Do I really have to wear diapers to work every day? Can I at least take it off before we get to the winery? I don’t want anyone to see me like this!”

“Yes, you must wear them all day every day. You wore to work and you got through it, so no excuses now why you can't wear around others.”

“But… they’ll know!”

“And they’ll have to deal with it. Get used to it baby boy, because those diapers aren’t going anywhere, unless you’re getting changed into a fresh one.”

He threw his hands over his face and groaned. He had been so ready to agree to self-diapering at work, but the closer we got to the winery, the less confident he felt. He was entering yet another unknown situation – unknown how he could operate in a diaper in the new environment. Unknown how Melinda and Carter would react. There were just so many unknowns.

“Take it easy, love,” I said, as I got out of the car and opened the back door. “This is supposed to be something for us to relax and enjoy. Now lay down.”

He looked around nervously. The open convertible provided little cover, even if there was almost no one parked outside. It was the middle of the week after all, and approaching sunset. We practically had the place to ourselves.

“I-I can’t,” he said, looking pale with fear. “W-w-what if someone walks out of there and sees us?” he asked.

“They won’t,” I said. “And I wasn’t asking.” Yet another thing he would have to learn was to trust me. I reached for his belt and undid it, pulling his pants down roughly.

“If you want to walk in there with pants on, you’d better stop squirming and let me change you. Otherwise everyone really will see you in diapers.

There. The balance of the threat was reset. Now relaxing and staying still was his best option. And he did, throwing his arm over his eyes to block out the surroundings and letting out a few involuntary moans as I untaped the front of his soaked double-stuffed diapers.

“I think we’d better choose something a little thicker. How about these,” I said, holding up some thick crinkly white diapers. I did my best to sell him on their virtues. I explained that they were nondescript, aside from their incredible bulk, and if anyone spotted them peeking out of his waistband, he wouldn’t have any explaining to do.

“Or I could put you in these fun ones with safari animals frolicking all over them. It’s up to you baby boy. Since it’s our anniversary I’ll let you decide.”

The old, give them a false choice tactic. He pointed a finger at the white one, and I smiled. I loved making him an active participant in his own diaper degradation.

“Good job picking your own diaper, little boy! So mature for your age, kiddo. Such a good helper for Daddy!”

He whimpered, as I unfolded it. I could already see he was turned on immensely by this situation, which I was happy to point out as I cleaned him up, slid the dirty diaper out from under his bum, and replaced it with a fresh one. I didn’t take too long because I didn’t want to miss the sunset, so I quickly powdered him, taped him and helped him into a seated position.

“Okay, buddy. Step out of the car so I can finish pulling your pants back up.”

“But, Daddy-,” he whispered.

“No buts,” I said. “Do you want a spanking in the parking lot? I thought you learned your lesson, but I’m happy to teach you again…”

He quickly jumped out of the car and stood there, shifting uncomfortably. I made sure to give his little package a squeeze through the padding and give his mouth a long deep kiss. Just then Carter poked his head out the door.

“Hey, guys. I just saw you pull up and- ohhh. Sorry, didn’t mean to interrupt. See you inside, love birds. Oh, and lookin cute, there, Tommy!”

Carter’s head disappeared into the winery. Tommy was devastated.

“He- he- he- he-….”

“Shhh, shhh, shhh,” I said, putting a finger to his lips, before bending down and pulling up his pants. I buckled them up and grabbed his hand. “Nothing a little wine can’t fix. Come on, just enjoy the day. In a few minutes, you’ll have forgotten all about it.”

I pulled him in, and Carter greeted us enthusiastically, while Tommy was unable to meet his eyes.

“About time you two came together. What’s it been, Tommy? Almost a year since we got your little butt up here? Well, we broke out the best for you and the Boss’s anniversary. Set up a table and everything.”

“Th-thanks…” Tommy managed to mumble, his cheeks tinged pink from the knowledge that Carter had caught him with his pants down. Of course carter and Melinda already knew he needed diapers. I was sure to vet them ahead of time and make sure Tommy was in no danger of a negative reaction from someone at the winery. But of course he didn’t know that.

“Heyyy! Is the cuteone here yet?”  asked Melinda, walking into the storefront from the back. “I thought I heard someone new. Hey there, Tommy. Oh no, now don’t start with that handshake crap. Give mama bear a hug!”

His face went red as she squeezed him tight, causing him to rustle like a paper-wrapped gift.

“Gosh, he’s a cute one, boss. Hasn’t aged a day since you first brought him in. Hard to believe it’s already been a year, eh?”

“Harder to believe when you don’t live with him! This little guy can be quite the handful!”

“Oh, come on. Look at him! Could you see this adorable little fella bein anything more than a perfect angel? Don’t worry, sweetie,” she said, turning to him. “I’m not gonna let your boyfriend talk smack on you. Even if he is the big boss here. Let’s get you two something to enjoy that wine with. Cheese work for you?”

He nodded, while instinctively holding his shirt down to cover the already prominent bulge in his pants. Of course he was being polite (or just bad at saying no) – cheese often sent him running to the bathroom, but I figured it wasn’t much of a problem now that he was wearing his toilet, so I didn’t try to save him from this one.

Hey, check it out, guys. I got this 1948 reserve that we found by accident a while back. Found a whole case of it. I better not tell you what the other bottles sold for at auction or you’ll never drink it. Anyway, that’s just the first one. Let’s give it a taste, eh?

He poured four glasses of the wine and the four of us clinked glasses. It really was quite good, though Tommy was probably more grateful for the fact the the focus of the conversation had shifted away from him, at least for the time being. Mercifully for him, we were escorted to a table they had set up overlooking the vineyard, and we were treated to a heart-stopping vista of the golden sky over green rolling hills. Rows and rows of grape vines covered those hills, extending out into the distance where the early evening air cast a soft haze over everything.

“Wow,” said Tommy, almost taking a seat on thin air as he kept his gaze trained on the strikingly beautiful scenery. “It’s even more beautiful than I remember.”

“And you’re just as beautiful as ever,” I said, with a grin.

He rolled his eyes. “Where’d you get that one? Off a cracker-snack box?”

“Hey. It’s a classic American snack!” I said, shrugging and smiling.

“Speaking of snack, boys. Dig in. You’ll have to tell me how you like the cheese and crackers. Actually, we’re testing these out for the next tasting season,” she said.

“Melinda…” I said, in a warning tone.

“Alright, alright. I get it. No business during pleasure time.” She held her hands up, then moved one to the side of her mouth and whispered to Tommy. “Just tell me how ya like it after. One wink means good two means bad.”

“Melinda.” I said, rolling my eyes.

“Hey, try the wine guys. I wanna know how you like it! You should start at this end and progress through the wines. That’ll give you the best flavor progression.”

“Carter!”

“Sorry, boss!” He said, pulling his fingers across his lips like a zipper and throwing an imaginary key away.

I picked up a piece of cheese and Tommy picked up a wine glass. I took a nibble. He took a sip. We looked over to my two head managers and back to each other.

“Get outta here you two! Come on.”

“Fine! Enjoy the sunset. But I better have a chance to chat with him after,” said Melinda.

“Enjoy, boys,” said Carter, pulling Melinda along with him as they disappeared into the winery. I immediately saw their heads popped up in the window, and I just shook my head and chuckled.

“I think that’s the best we’re gonna get,” I said. Taking a sip of my wine. “Damn, that’s good.”

“I-it is pretty good,” said Tommy, taking a sip. Then another. Then another.

Before he knew it, he was well past tipsy and halfway to trashed. And carter didn’t show any signs of letting up with the wining and dining. I was getting past my limit as well, and I didn’t like to do that because it meant I might say something I wasn’t planning to say. A problem for someone who very much liked being in control. Unfortunately it also affected my coordination.

We watched the sun dip down to the edge of the horizon, grow wide, then slowly, slowly flatten until only a tiny sliver of orange was left. This was soon followed by a fantastic twilight, with blues, purples, oranges and reds painted across the sky. It was easy to just let all our daily concerns wash away. He forgot about being self-conscious, and I forgot about forcing him into ever thicker and more public diapers. For a moment, we were just there in the moment. Enjoying it together, like we had the day we met. And then, that moment was gone as I heard the splash of water dripping on the flagstone.

I looked down and saw a puddle rapidly forming under the chair. I followed the drip and saw they led up to his seat, where his pants had ended up soaked.

“Oh..no… Tommy1” I said, looking slightly concerned. “Looks like my little guy had an accident!”

He looked down and after a second or two delay, his eyes slowly widened in surprise to see that he had indeed soaked his pants.

“Oh jeezh… Whendithat happen?”

“I dunno, buddy. Don’t worry, I’ll get it.”

I stood up but quickly plopped back into my seat when I realized how dizzy that made me.

“Hey, are you two okay?” asked Melinda stepping out to check on us.

“I hadda accident,” said Tommy, pointing to his pants.

I giggled at his slip-up, but quickly covered it up by pretending I was coughing. I was in no condition to change a dirty diaper.

“I’m sorry, Mel. I think I’m gonna need help on this one…”

Melinda, not fully comprehending my words, followed his finger to see some very wet pants between his legs.

“Oh! Come on, come on.” She hurried him out to the back area of the château, wasting no time once she knew what the problem was. Past the open-air spot where employees snacked and rested, off to the side was a restroom with Spanish tile and a sturdy table butted up against the wall. I leaned against the wall and watched things unfold, no pun intended.

“I’m sorry, Molly, said Tommy, slurring his words. “I didn’t mean to ruin your birthday party.”

“Shhh. You are drunk, sweetie. Let’s get you out of these pants.”

She’d had the presence of mind to grab his diaper bag when she pulled him away, and with his pants off, she was now setting up the changing supplies on the table beside him.

“Bingo!” she said, as she got the thick animal print diapers from the bag. “Lay back buddy. There we go, don’t hit your head. Alright. Oh boy, hon, you are soaked! Let’s get these offa you.”

Tommie just played with his hands, oblivious to what was happening below his navel. He laughed as the wipes tickled his legs and said “whee!” as his butt was lifted in the air for more tickly wipes to reach his behind. Luckily this wasn’t the first diaper Melinda had changed, though it was certainly the largest, as she would later confess.

“You’re lucky you’re small, kid,” she said, unfolding the new diaper.

“Daddy says I’m itty bitty,” he giggled.

“Daddy, huh?”

Melinda raised an eyebrow at that and looked to me. I just shrugged and tried to look innocent as possible, but she gave me a look that told me we would be talking about this later.

“Okay, hon. Here comes the powder. Can you lift your butt up for mama bear? Good boy. Alright, now legs open wide! Just like that! Let’s count out tapes. One! Two! Three! Four! Great job!” She clapped, her demeanor having completely changed once she heard the word ‘Daddy’ leave his lips. The funny thing was, he responded. On some level, I guess that was just something he clicked with, and I was amazed to see how effective her technique was for keeping him happy and engaged.

I chuckled and shook my head.

“Don’t laugh now, mister, or you’re next!” she said, pointing right at me. Now it was my turn to blush.