Daily Free-Write February 2, 2021

I keep meaning to wrap things up with this story but it keeps expanding! Too bad for Skylar ;-). I'm still experimenting with having more continuations in my free-writes, and perhaps even completing stories in this way since I can only do so many PDFs in a month - the PDFs are much more carefully edited and refined and just take more time. I may try to finish this story in the free-writes or take it to a word doc to finish and release as a PDF. If you have any preference one way or the other, let me know! 

Continuation of February 1, 2021 “Playing Dress-Up Pt. 4”

The next day at work I was constantly on edge. My only work pants were made to fit a triple diapered Skyler, and they had snaps in the crotch which anyone might notice if they looked too closely. As for the diaper bag which I had to bring everywhere I went, I decided to go with the baby bag. At least it was nondescript. I didn’t think I could walk into the office with a colorful T-Rex backpack and not get some funny looks and questions. At least this one I could walk in quickly and quietly and stash it under my desk without much notice.

I sat at my desk thinking about my strange weekend. How I was going to be thickly diapered from now on – wearing at least three layers during the daytime, and perhaps even thicker cloth diapers at night. How I was humiliated in the store. Forced to model all of my new clothes for Steve and Mr. Lee while they made comments and ‘inspected’ the workmanship. How I was changed in the family restroom by Skyler, and how I was then forced to go through the checkout line and buy all my new baby diapers, clothes, and accessories in nothing but a babyish T-shirt and diaper. A T-shirt that didn’t even reach past my belly button. And how back at home I was forced to throw away all my old pants, guaranteeing that I would have to stay thickly padded if I didn’t want to risk them slipping off while I was out and about.

But the most humiliating thing of all was the image that Steve sent me. The image of me in a diaper and T-shirt standing at the check out line with the caption ‘Bullseye’s Biggest Baby’ underneath. The image was on the front page of a website that anyone could see – People of Bullseye. And I knew that if any of the people at my work went on there, they’d see me, diapers and all. And it wouldn’t be hard to notice the outline of a diaper under my pants or hear the noisy crinkle and put two and two together. I was sweating under my collar. Was it the thermostat or my own nerves? This is one of those days I wished I didn’t wear a shirt and tie to work.

“Skyler Johnson!” I practically jumped out of my pants when a voice rang out behind me. Oh no. It was Ricky, the office prankster.

“Hey, Ricky,” I said, pulling out a tissue and mopping my brow.

“Howdy Sky. You workin’ hard or hardly workin’? Hahaha.” He slapped his belly as he laughed. He was a tall skinny man with sharp angular features. Skinny and sharp aside from his belly, a pot belly which stuck out from his body as if it didn’t’ belong, and which he beat like a drum whenever her thought something was funny. “I crack myself up. Hey, I see I’m not the only one growing a belly here, hey champ?”

He gave my belly a slap and I shrunk away from him.

“Hey! Hands to yourself!” I said, glaring. Working with him was like working with a kindergartener who’d drunk too much kool-aid. And his desk was right across from mine. You can imagine the fun we got up to. Well, it wasn’t fun for me.

“Geez, fine…” he said, stepping away. Then he shrugged. “Some people can’t take a joke.”

I shook my head and got back to my work. If nothing else I was grateful for the fact that he distracted me from my ruminations. I couldn’t think about how I had been completely owned and dominated by a handsome store attendant half my age. Damnit. I was getting hard again. I squirmed and tried to squeeze my legs together, anything to scratch that itch, but the diapers were too thick. They prevented me from sitting with my legs at anything less than a 90 degree angle and completely prevented any sensation from reaching my nethers, aside from the sensations provided by my wet and squishy diapers.

I turned to my computer. I had to stop thinking about what was between my legs and start thinking about my work. I had data to enter. Emails to answer. Coworkers to ignore. Namely the one behind me, who had just fired a spitball at my head.

“Seriously, Ricky?” I said, turning around and looking at him while he innocently whistled from his chair.

“What? Me? I didn’t fire a spitball at you.”

“I didn’t even mention what you did,” I said, closing my eyes and rubbing the bridge of my nose in frustration. I looked back up at him. “Listen. Dude. You gotta chill out. I seriously have a lot on my mind right now, so could you please just… not? For one day. Just leave me alone.”

He stuck out his lower lip.

“I’m sowwee buddy! I won’t do it again!”

I rolled my eyes and went back to my work. Promising myself I wasn’t going to kill him and lose my pension. Although it was very tempting. At least the next 30 minutes or so passed peacefully enough, until I got a text on my phone. It was from Steve.

“Diaper check” was all it said.

“I’m at work” I texted back.

“Diaper check. Now.”

“Give me a sec. I need to find a bathroom.” I set the phone down and huffed as I reached for my diaper bag. I saw the message pop up and stopped what I was doing.

“No you don’t. Just take a picture where you are.”

I looked around. Then texted – “But I’m at the office. Someone could see. “

“Not my problem,” he replied. “Don’t make me punish you, little boy. You won’t like it if I do.”

I gulped. What exactly did he have in mind? He’d seen my ID. My Car. What else did he know? What else could he do? Worse still, what if his punishment was to just never speak to me again? I had just met a hot cutie who wanted to diaper me. ME. Was it worth risking my career over? I bit my lip and looked over my shoulder. My coworker looked like he was actually working for once, and no one else seemed to be in view. I decided to make it quick. Just a little peek. If I scooted forward and took the picture under the desk, no one would be able to see. Right?

“OK” I texted back. Then I had a brilliant idea. I didn’t even have to take off my pants. I had snaps. From above no one would be the wiser, especially with me scootched forward as far as I could be and as quietly as I could, I unsnapped the first button. I squeezed my eyes shut as if I had just dropped a cherry bomb. I listened. I looked around. Nothing. Whew. I carefully unsnapped another. And another. Soon, I had enough of my pants unbuttoned to show off the front of my diaper for the camera. As surreptitiously as I could, I took the phone, looked around, and snapped a picture of my crotch. I looked at it. Damn. No good. Not enough light. I would have to scoot back from the desk a bit. I looked around behind me. Ricky was still engrossed in his work. I scooted back. Ever so slowly, just far enough for the light to reach my diaper. I took the shot and sent it.

“Johnson!” I slammed my chair forward so fast I nearly flew off the chair as I hear my boss call my name from right behind me.

“Oh… h-h-hi boss!” I was sweating bullets. Had he seen me?

“I just wanted to congratulate you on getting employee of the month.”

“O-oh,” I said, smiling as I leaned over on the desk and prayed he would leave me alone.

“Your spreadsheets have been the model every data entry clerk looks to, and I’d like to offer you a promotion. How does head data entry analyst sound? You’ll get your own office.”

“Oh you don’t need to sell the position to me, sir,” I said, looking over at my coworker from hell. “I’ll gladly take it.”

“Great,” he said, sticking out his hand.

Crap. Now I had to stand up and shake his hand or it would be rude. I had no choice.

“Thank you sir,” I said with a big smile, bringing my hand and elbow high up to meet his hand in an enthusiastic handshake. I figured I’d give him the ol’ razzle dazzle to hopefully distract from the stinkle crinkle.

By some miracle he didn’t seem to notice my diaper at all, and with our discussion complete, he left. I looked down and quickly saw why. Then I was standing, he front of my pants sat normally. You wouldn’t really be able to notice anything odd unless you were low to the ground. What a relief. I quickly plopped down into my seat and snapped up my pants. Then I looked over to my desk in horror. My screen was still on and showed a picture of my phone, and the words from Steve. “Good Boy. You don’t need a change yet.”

Shit shit shit. Had he seen it? If he had, he did an excellent job of playing it off. It was one of those moments that I just had to try and forget. Pretend it never happened. I’d never know for sure, so there was no point in thinking about it any longer.

“Hey, Skyler, congrats!” said Ricky. “It’s a big promotion. Your own office. Maybe even a pay raise. So why do you look so stressed?

“Its… nothing.” I said, glancing down at my phone. I could see the message alert pop up with a message preview.

“Go get some coffee. Drink three cups so you can be a good worker while you fill…”

“I’ll be I know what the problem is,” he said with a sly grin. Shit. What had he seen? “You’re gonna miss your old pall Ricky!” He gave me a pouty face, and I mentally sighed, relieved, and annoyed at the same time.

“I’m gonna go get a coffee.” I said, standing up to go.

“Whoa, Skylar!” he said. “I see I’m not the only one who’s put on weight.”

“Excuse me?” I said, looking down. I wasn’t that obvious, was I?”

“You’re storing a little junk in the trunk I see. Saving up all those nuts for winter, I presume?”

“Tch. Knock it off, Rick.” I said, waving him away and turning my head to hide my blushing cheeks.

“Aww, it’s ok. I’ll tell you what. I’ll let you play my belly if you let me play your butt!” He smacked my butt, which let off a loud WHOOMPH. He pulled back, looking confused and cocked his head.

“Hey!” I yelled, stepping back, then quickly lowered my voice, speaking in a hiss so as not to attract more unwanted attention. “That’s totally inappropriate!”

“I’m sorry,” he whispered back. “Did you want to go first?”

“I’m going to get my coffee now. If you touch me again, you’re going to lose that hand.” I said, quietly. If he wasn’t half my size, I would have clobbered him then and there, but I didn’t want to spend the rest of my day in jail. I made a mental note to update my log of grievances and find a good lawyer before I brought this up with HR. I thanked the stars that I would be moving to my own office soon. For me it couldn’t be soon enough.

I waddled away with as much dignity as I could muster, wincing at the volume of the crinkle that followed me with every step. The crinkle of the diaper as I walked toward  the break room was impossible to ignore  in the quiet office environment. And yet, no one seemed to really look my way.

I poured myself a cup of coffee with cream and sugar and threw a few cubes of ice in it to cool it down, then I drank it as quickly as I could. I repeated this process twice, taking a picture each time I emptied my mug as per Steve’s instructions. Then I washed it down with a cup of water to dilute it a bit in my stomach. I opened the fridge and bent down to grab a snack from my lunch bag, when a voice called out from behind me.

“Oh, honey. Your, um. Your shirt is riding up a bit there.” It was Marie, the Boss’s assistant.

“Oh!” I said, standing bolt upright and pulling down the back of my shirt. “Um. Thanks.” I was so embarrassed, I didn’t even know what to say. I just closed the fridge and walked away so stiffly I probably looked like a robot.

What was happening today? I felt like I was being exposed to and by everyone around me. Not that I blamed Marie, or my boss, or even Steve. It was just a step outside of my comfort zone and I was understandably on edge. So naturally, I chickened out. I surreptitiously went into the bathroom and pulled out my phone.

“I can’t do this anymore,” I texted Steve. “I’m a total mess right now, and I’m afraid my coworkers are going to notice my diapers. It’s too much.”

He called me, and I picked up.

“What’s going on, Skylar. What can’t you do?”

“I can’t wear these diapers,” I said into the phone. “They’re too thick. I can’t go to work like this because people will notice! I think some people already have… I…”

“Skylar.” He said, and I stopped. “Listen to me. You need diapers. That’s all there is to it. You need them, and you need to wear diapers that get you through the day at work so you don’t have any more leaks.”

“I know,” I said, “but It’s so obvious. I’m looking at myself in the bathroom mirror and my butt’s sticking straight out like… well, like I’m wearing a diaper. I look ridiculous!”

“You can’t hide at home forever and call in sick because you’re embarrassed about your diapers. Now I’m telling you I’m 100% sure everyone knows about your diapers already. I’m sure they just assume you have a medical condition – and you do. You’re just doing what you need to do to stay protected. Do you understand?”

“Yeah.” I sighed. “I guess… I guess so.  But what if they think I’m some sort of weirdo? What if… I don’t know what if…”

“Skylar, calm down. Just because they know you wear them, doesn’t mean they need to know that you enjoy them. And there’s nothing wrong with enjoying them. You get to wear the underwear you want, and no one gets to tell you what you can or can’t wear under your clothes… except me that is.”

I nodded. His pep talk as making me feel better about my decision and making me feel little huffy as well. He was telling me what I wanted to hear… that it was okay to wear my diapers... that I needed my diapers… And naturally I found my hand wandering down to the front of my padding and rubbing. However, I was only frustrated by its thickness.

“Why are you making those noises, little one? What are you doing?”

“Unh.. I’m… erf… sorry. It’s all that coffee. It’s making me really excited, and… these diapers are too thick to do anything about it.”

“Well I guess you’d better hurry up and fill them so you can take them off and get a little stress relief.”

“Y-yeah,” I said. Then my tummy rumbled as if in agreement. “Erf… I-I think that coffee is going to make that happen sooner than expected – in more ways than one. I have to go…”

“Hold on. What do you have to go do?”

“You know…”

“I want you to tell me.”

I looked at the door nervous someone might walk in at any moment. Then I said in a hushed tone.

“I have to go… get my bag.”

“What bag, little guy?”

“My… my diaper bag.” I stammered. I was very turned on at this point, and could already feel my hard on poking in to my increasingly soggy diapers, the first spurts of coffee-scented pee spurting into he front of the padding, soaking it with warmth. I could already smell it, and I knew that I had made a mistake. Coffee scented piss had an unmistakable odor and I was going to be covered in it.

“You sound like you’re enjoying yourself, little one,” he said. I hadn’t realized I had been moaning as I felt my bladder release and flood my diaper. “Do you like going peepee in your diaper little one?” he asked.

“I-I do….” I admitted, bashfully.

“You do what?” he asked. I could practically hear his naughty grin on the other end.

“I like… I like going peepee in my diaper…” I said.

“And poopoo too?”

“Yes….”

“Say it, little one…”

“I like going poopoo in my diaper too…” I said. I couldn’t believe he as making me admit these things out loud.

“Good, because that diaper isn’t coming off til you’re completely empty. Unless, of course, you want to try and hold it for the rest of the day.”

There was no way that was happening.

“No, I don’t’ mess at work. Please…”

“The potty is off limits for you. From now on you use your diapers for everything. You do remember your promise don’t you?”

Damnit. I had agreed to do everything he said. And with the information he had already, he had me by the balls.

“Yes, sir,” I said, finally.

“Good. And I want proof. Otherwise, I’ll have to come over there myself and make sure you use them properly.”

“N-no! You can’t do that.” I said.

“Well now I have to come over. I’m coming over at lunch time. I’ll be introducing myself as your boyfriend. And if you don’t agree with everything I say while I’m there, I’ll correct myself and introduce myself as your Daddy instead. Is that understood?”

“H-how do you know where I work?” I asked.

“Skylar Johnson. 35. Working at DataDyne Systems. Just got promoted to … head data entry analyst! Well done! And you’re employee of the month. I could go on. Ask me anything. I’m an expert. After all, you did agree to do what I said.”

“B-but that was just in Mr. Lee’s office… because I had to …. I mean… That wasn’t for everything….”

“Oh? So your word isn’t good enough? It’s a shame. But if your word isn’t good enough your signature certainly is. You signed a contract with Bullseye, remember?”

“I…What?”

“Check that video I sent you again. Maybe it’ll jog your memory. I think I’d better let you go before you have an accident. See you at lunch. Oh, and just in case you’re still thinking of chickening out, I’ve got someone keeping tabs on you. They said you look very cute crinkling around in your new pants, and they’ve left you a little surprise on your desk. See you at lunch time, little one!”

I hung up. Oh shit. What had I gotten myself into? I was terrified and excited. I felt crazy to be so turned on by this turn of events, but I also felt like things were quickly spiraling out of my control. I took a second to steady myself on the sink. After many deep breaths, I was able to center myself and get my heart to stop beating like a jackhammer. Ok. I was okay. That’s when I heard a toiled flush and my heart leapt out of my throat.  Out of the stall walked my boss.

He leaned over the sink to my right and washed his hands. Then he looked over to me, cool as a cucumber. “Sometimes I like to use the employee restrooms. They’re much more colorful than the executive washroom. But… if you want more privacy, you’ll find the key in your new office.”

My mouth hung open. I was mortified. Had he heard all that? How did I still have my job?

He dried his hands off and tossed the paper towel into the garbage can.

“A three pointer. How about that? I still got it. Well, I’ll see you around the office, Sky.”

He turned and left.

I felt a lurch in my stomach, and it wasn’t just the complete and utter humiliation I felt. It was soon followed by a loud gurgle, and I was out the door like a flash to get my diaper bag.

-Written by Champ