Daily Free-Write January 28, 2021

“Darn. I’m going to need to buy new pants.”

I sucked in my gut as I tried to fit my khakis over my padded bottom, but the button just wouldn’t reach. My bedroom was littered with every other pair of pants I owned, and this was the final one. I let out a sigh and gave up. The fly hung open, showing a very colorful jungle print diaper cover.

I had just switched medication and I found myself wetting more frequently. Diapers that would normally last 8 hours were only lasting me four, and I had to go to thicker diapers with thicker stuffers and diaper  covers with cloth inserts just to make sure  I wouldn’t leak in the middle of my day. Unfortunately, as my diapers grew, my pants didn’t grow along with them. I dug through the hanging clothes organizer in my closet hoping for a temporary fix, and all I came up with was a pair of gym shorts, some pajama pants, and a kilt.

“Well… I can’t go out in pajama pants… those would just make me tacky, noisy, and more obvious. The gym shorts barely cover anything. I guess it’s the kilt.”

I gulped, holding it up. The utility kilt was just a hand-me down from my ex, and wasn’t something I ever wore out, but it would be much more forgiving than any of my pants. I just worried about the potential for exposure. I shook my head and sighed. “There’s no getting around it. Guess I’ve gotta go out in this.”

I managed to squeeze into the kilt, and waddled my way out to the car. It wasn’t a long drive to the Bullseye store, where I could find some relatively cheap dress clothes that weren’t threadbare enough to be see-through. As I pulled into the parking lot I cursed the fact that still I had an office job. If I worked remotely, I wouldn’t even need pants. Not to mention the hassle of changing them.

“Better get a new diaper bag while I’m at it…” I said, thinking about the added bulk those diapers took up in my regular drawstring backpack.

As I grabbed my cart and waddled around the store, I thought I really wasn’t so out of place in this unusual getup. I imagined myself on the website ‘people of bullseye’, sandwiched between pictures of people in pajamas and hair curlers, and people with no discernable pants at all. I could just see it now. Skylar, the Bullseye diaper boy. I chuckled to myself as I went through the men’s clothing section.

“Let’s see… I was a 34 waist… but now…” I looked down at my bulging kilt, as well as my baby belly which had grown a bit since the summer. “Now, I guess I’d better start looking at 38s.”

I blushed as I thought about how my diapers were actually forcing me to get new clothes. If I thought about it, I really had to adapt my whole life around wearing 24/7. Sure, it was second nature after five years in diapers, and most of the time I didn’t even think about it, but then there were times like these…

“Ahem.”

I turned around to see a sales associate standing behind me. He looked to be in his late teens or early twenties, much younger than my age of 32, and his red uniform vest, black slacks, and white dress shirt were clean and crisp. He was strikingly handsome with a button nose, freckles and short brown hair, and when I realized I was staring, I quickly recovered.

“Oh… I’m sorry, am I in the way?” I asked stepping aside. He chuckled and smiled.

“Oh no, no, no. I came over to see if I could help you.”

“Oh… Well I…” I could use some help but no way I was gonna tell him. I was much too shy around people I found attractive. “N-no… it’s… fine.” I said, meeting his gaze briefly before looking away.

“Let me guess,” he said, as he gestured to my kilt, undeterred by my reluctant response, “emergency trip to find pants that actually fit?”

I nodded, and he did as well.

“Happens all the time. Don’t worry about it. I’m guessing you’ll want to try some things on too, huh?”

I thought about it. “Yeah, I guess I’d better. Are the fitting rooms available?”

“Of course. Why don’t we see what we’re working with and get you all set up? I’m Steve, by the way.”

Steve made me feel very comfortable as I picked out pants. I was hoping he wouldn’t notice my thick diaper, but I had the feeling he had sussed that out pretty quickly.

“So we’re looking for something a little roomier in the seat. Darker colors are best, so you won’t have to worry about any stains or… spills.” He gave me a wink. He pulled out a measuring tape and held it up, poised to go around my waist. “May I?” I nodded and let him measure me.

“Alright, one sec.” He ran around and in no time he had about five pairs of pants for me to try on. I was grateful as he led me over to the fitting rooms and thanked him for his help.

“Oh, we’re not done yet,” he said as he held open the door to the fitting room. “I’ll still have to measure you once you’re dressed. You don’t want them to trail to the ground and get all torn up, do you?”

I shook my head no, and walked into the fitting room. He had given me the handicap one so there was plenty of space for me to change. My heart was beating so hard it was threatening to jump out of my throat as I imagined him on the other side of the door. I unbuttoned my kilt and set it aside.

*Crinkle*

I reached over to try on my first pair of pants.

*Crinkle*

I pulled them up and buttoned them, sighing in relief to be in a pair of pants that didn’t make my face turn red with effort whenever I bent over.

*Crinkle Crinkle Crinkle*

Normally I would have tuned the noise of the diaper out completely, but now the whole space seemed to be filled with the sound of plastic crinkling. I shook my head. No getting around it. I tried on all five pairs, turning this way and that to see how obvious they made my diapers, squatting and bending over to make sure I could actually move in them. One thing I needed was a belt, since the ones I had were all on their last notch.

“How you doing in there?” he called.

“Good! I… I think I’ve made my choices.”

“Oh great. Come on out when you’re ready. I’ll you in them.””

I blushed as I opened the door and came out, holding them up with my hands.

“Here, follow me to this three-way mirror,” he said, walking back toward the entrance to the fitting rooms.

I blushed and held on to my pants for dear life as he instructed me to squat and bend over a few times. Every time I did so, my wet diapers would rub on my already sensitive dick, and I had to bite my lip to keep from moaning out loud. Finally he was satisfied and I was grateful as I was a hair’s breadth from blowing my load right in front of him. While I thought about what a close call that was, he quickly got into position to measure. His face was mere inches from my padding as he held the tape against my pants, and I closed my eyes and prayed he couldn’t tell what was going on down there.

“We’re going to have to get you a new belt. Let’s see… Oh, excuse me,” he said, bumping my hand accidentally as he tried to put the measuring tape around my waist once more. I quickly lifted my hands out of the way.

“Sorry!” I said before I realized too late that there was nothing there to hold my pants up. “Oh!”

In an instant, my pants were around my ankles and his little nose was inches away from my thick and colorful diapers. The intoxicating scent of piss, baby powder, and horny boy wafted up up to hit my nose full force and I could see him wrinkle his nose a bit as the smell hit him as well. I fumbled to pull up my pants, apologizing profusely, but he stopped me.

“Hey. Don’t worry about it. Go back and grab another the rest. I’ll keep these.”

I wanted to say something but I couldn’t think of any excuse or explanation that would help my situation. I didn’t have to, though, because he did the thinking for me.

“Come on, step out,” he said, holding the waist so that I could step out easily. I stood there awkwardly for a few moments before he reminded me to go get the pants I wanted to keep, and I quickly toddled back toward the dressing room, crinkling loudly as I did so. Each moment that passed left me with the worry that someone else could come around the corner and see me in my diapers.

The measurements continued for three more pants, and every time I came excruciatingly close to losing control and cumming in my pants right there. Finally, with the final pair, he pulled up on the front of my waistband to adjust the pants and I lost it. It was obvious what I’d done from my expression and the way I shuddered and squeezed my legs together. I was not quiet about it either. Then my bladder emptied its contents into my diaper, which began to leak. The cloth all-in-one did not do its job, and I felt a wet patch growing at the back of my thighs.

“I think these pants will do just fine,” he said with a smile, before he sent me back to get re-dressed.

He took my contact information when I got back and handed me my receipt for the tailor.

“Come back tomorrow, same time, and bring your diaper bag,” he said. “You should know better than to leave home without it.”

I just nodded and apologized, relieved that it was all over. I knew I would have a story to tell when I got home, but I had no idea that my story was only beginning. When I got home, I got a text message from Steve. There was a recording of the scenario, complete with me waddling back and forth in a diaper, and coming to a final shuddering conclusion as I climaxed in my pants.

“Thought you might like to revisit today’s little escapade. It was cute to see you play dress up, trying to look like a big boy. Don’t think it will be your last time creaming your pampers in public, diaper boy. The fun is just getting started.”

I gulped. Was I really going to go back tomorrow? And what was going to happen with the wet pants? I was nervous and excited, and I immediately started rubbing the my diaper bulge as I watched the video again and again.