Daily Free-Write January 29, 2021

Continuation of January 28, 2021 “Playing Dress-Up Pt. 1”

“It’s past noon… I really ought to get going…” I thought as I checked the time on my phone. I had been restless all day. Checking my texts and doing whatever chore or bit of work I could think of to get my mind off of going to Bullseye to pick up my clothes. Steve still hadn’t texted me back, and I was beginning to think it was all a dream. Only the video told otherwise.

I popped my medication and checked my diaper in the bathroom… not too wet. I decided to forego the cloth diaper cover this time opting instead for a discreet onesie. This time it was easier to fit my butt into the kilt, and I nodded with satisfaction. As I made to leave, I paused. Steve had said to bring my diaper bag.

I went and grabbed my drawstring backpack, just big enough to fit a couple diapers in and some wipes. That would have to do. I had been so flustered by my encounter with Steve the day before that I completely forgot to buy a new diaper bag. A tote bag or similar would have done. I just hoped this would be enough to hold me over til I got home.

I parked and walked into the Bullseye, once again I was acutely aware that just under my kilt was my thick and crinkly padding. The only thing keeping it hidden was gravity. I sent out a text when I got inside to tell him I as here, and got a quick response.

“Tailor’s office. West side.”

Which side was west? I made a big circle around the store and eventually found it. There was Steve chatting with the tailor.

“There he is,” said Steve, as I came near. The tailor, an old Chinese gentleman named Mr. Lee, gave me a knowing smile and walked deeper into his workshop to grab the proper items. It was slightly embarrassing because I had had him do my alterations before and he would easily see I was a little bulkier in the belly and downstairs. However, I was even more embarrassed when he returned with the pants and more.

“What’s that?” I asked, pointing toward two outfits I had never seen before.

“Your order of course. Three pair of pants, and two custom outfits,” stated Mr. Lee. “These are very cute. Easy for changes too thanks to the snaps.” He held up the pants.

“Snaps?” I asked. My eyes widened when I noticed that he had indeed put crotch snaps in all my pants. They were the same color as the fabric so I didn’t see them at first, but once I did, I couldn’t miss them.

“Isn’t he the best?” asked Steve, looking excited.

“Yeah…” I said, as if in a daze. This was both exhilarating and terrifying at the same time. I had no Idea Mr. Lee would make these kinds of alterations, or I’d have asked him a long time ago. But could I really wear thoseto work?

Mr. Lee showed me the other two outfits next. “Footed sleeper. I turned the feed backward and installed a locking zipper. Much more comfy and secure, don’t you think?” He said. Of course I could only nod, as I tried to hide the discomfort of my erection trying to break free of its padded confines.

The last outfit was a complete surprise. “Is that…”

“I saw you looking enviously at the kid’s section yesterday,” said Steve. “So many cute things! Shame they don’t make any of that stuff in your size. Luckily, Mr. Lee was able to throw something together.”

“Throw something together is an understatement,” I said. “This was the exact outfit I was looking at yesterday.”

The outfit Mr. Lee had made was a pair of gray shorts with elastic cuffs and waistband, and deep blue short-sleeve t-shirt with a big paw outline on the front, matching the paw print on the leg of the shorts.

“Well,” said Steve. Why don’t you try it on?”

“What?” I asked, suddenly snapping out of it. “Here?”

“Of course! We have to see how it fits.”

“But… but… the whole store can see me!” I said.

“Come on,” said Steve. “Don’t insult Mr. Lee. He worked very hard on these, and besides, we have to make sure they fit.”

I reluctantly reached for the buckles of my kilt, looking around to make sure nobody was nearby. I stepped out of my shoes and took off the kilt, reaching for the outfit to put it on as quickly as possible.

“Shirt too,” said Steve, holding his arm out to stop me.

“R-really? Come on… I can’t be seen like this…”

“Then you’d better hurry up and take off that shirt,” said Steve.

“You’d better do as he says,” said Mr. Lee, chuckling. “He means business!”

My heart was beating hard now, but I knew the faster I obeyed, the faster I’d be covered in something other than a diaper, so I took off my shirt.

“Okay, there. Now can I please try on the outfit?”

“Hold it!” said Steve, walking up to me to get a closer look at my diaper. “You’re soaked! You need a change.”

“What? I am?!” I looked down Can’t it wait? I just want to try on the clothes before anyone comes by.”

“Aww, the young man is excited to try on my clothes,” said Mr. Lee, smiling. “That’s the best compliment I could ask for.”

“Yeah, but I wouldn’t want him leaking on them like he did yesterday. You did a great job getting those cleaned up, by the way,” Steve intentionally made eye contact with me so he could see me blush and squirm when I realized Mr. Lee had seen the results of my accident.

“Please,” I begged. Steve came right up to me and I stiffened up as he cupped my diaper bulge in one hand.

“Hmm, I don’t know. I’d better check.” He rubbed and squeezed it a few times, causing me to grunt and bite my lip, and buckle my knees in an effort to remain composed. “Well, Skylar. I suppose a change can wait… if you agree to do as I say.”

I nodded so fast I thought my head would fall off. “Yes. Please. Anything!”

Steve smiled.