ddlb Sugar for Baby

[Lavellan]

Content Warning: This story will include sexual content as well as various other themes that may not be everyone's cup of tea. I will do my best to put content warnings behind every chapter, but do mind that this will contain diapers, ddlb dynamics, and sissy content. For this chapter specifically, I only need to give a minor sexual content warning as various things are mentioned but none are carried out. And with that, on with the story. 

Sugar for Baby: Chapter 1

 

"Good luck dude!"
"You'll be fine"
"Let us know how it goes."
 
Matthew sighed heavily as he slipped his phone into his pocket and grabbed his wallet and keys. The messages from the few friends he found in the group chat were encouraging him on his goal. His goal was an unusual one. Buy pull-ups from the store. It was unusual in the sense that, the pull-ups weren't for a younger sibling or a child. No, they were for him.
Matthew was 18 years old and 5’ 8” tall. He was smaller than most of his peers and more book smart than he was athletic. It was never much of an issue, though. While he had a few friends, they went off to college, leaving him back in his hometown to live out his gap year and find out what he wanted to do. His parents were upper-middle class, and they had no qualms about him taking a year to find himself. It wasn’t as if he was using it to slack off. He was never the type for that. 
and from a young age, he found himself with a fascination with diapers. His fascination went so deep that he made his parents think Mama Martha's Pizzeria was his favorite restaurant. It was a small, local business, well known in his town.

And while the food was nice and all, what made Matthew excited to go, was the bathroom.

Mama Martha's had two family bathrooms in the entire establishment. And in each bathroom, there was a large tub of diapers under the sink. On the front was a handwritten sign that said "Give a Pamper, Take a Pamper." Because it was a courtesy-driven thing. People would come in to change their baby, and if they found themselves out, they could take one from the bin, if they felt charitable, they could leave a couple behind for the next parent. Matthew always found an excuse to go to the bathroom before his family left the establishment. And every time, he would take one of the diapers (or pull-ups as he got older) and put it on before they left.

He loved the feeling of wearing them, he couldn't explain why. But he always had a smile on his face the entire ride home.

"Did you enjoy the pizza, Matty?" His mom would ask and he would nod to her.

Mama Martha's was a reward for him. They would only take him if he did well in class, or if he won an award. It served as great motivation for him to keep his grades up.
But soon enough, he grew too big to wear the ones at Mama Martha's.

It had been a handful of years since then. And he worked his way through school, saving up money for a car that his parents helped him buy. And went from working a fast-food job to being an online tutor. It paid well actually seeing as how he was a pretty good student and explained things well enough that his students hardly ever struggled.
It was how he gained most of his money.

But back to the present, Matthew cranked the ignition to his car, taking a deep breath as it started. Now was a good time for him to go to the store. Usually, his mom would want to tag along, but this time, she was out of town on a trip with her friends. And his dad worked and then went to a pool hall to have a drink with his friends before coming home. Since mom wasn't home, he wasn't coming home to eat dinner. Which was a-okay with Matthew.

It meant Matthew was free to go out on his mission.

The store Matthew picked was just up the road. And he picked said store for its self check out. The last thing he needed was to go red-faced at the check-out line and give himself away.
Parking towards the back as he usually did, he walked casually through the automatic doors and grabbed a hand-basket. Matthew took his time, grabbing a few other things before making his way to the diaper aisle. Low and behold, they had them all. Varieties of sizes and cases and brands lined almost the entire wall. Only being broken by the baby accessories. Clearing his throat, Matthew walked to the pull-ups.

The largest size they had should fit him just fine. His only conundrum was how many to get. Biting his lip, his hand reached out for the pack of 24 when someone stepping up beside him making him jump. Looking over, Matthew saw a man, a bit older than him, reaching up high on the shelf for a large 100 case of diapers. The man groaned as he pulled them down and smiled at Matthew.

"Word from the wise. Always buy in bulk." He said. "It's expensive, but better not to have to come back so soon."

Matthew nodded, looking back at the wall. He didn't want to carry out a case like the man beside him. He felt that would draw too much attention. Plus it wouldn’t fit in his hand-basket.

"You have a kid?" The man asked, sensing Matthew's thinking.

Matthew shook his head, "No! I'm just. Uh...shopping for my sister."

Matthew had no sister. But it was the quickest thing that came to mind.

The man nodded. "Well, I'll leave you to it." He says grabbing the case and heading to the checkout.

Matthew, now feeling much more paranoid, grabbed for the girl's pull-ups instead. Diapers were diapers. And in this case, he didn't care what they looked like. The sister excuse was a pretty good one. Grabbing a 40 pack of them, Matthew dropped them in his basket and beelined it for the self check out. He scanned his items, bagged them up, double bagged the pull-ups. And went out to his car, heart hammering in his chest. He was so caught up in the adrenaline of his purchase that the drive back home passed in a blur.

He took all the bags up to his room as soon as he got home. Even the bits and bobs he meant to leave in the kitchen. Taking his phone out, he pulled up the group chat. It was a large chat with over 300 members. He'd found the link on a diaper fetishist website and had been a member for almost a year now. He had even become an active and known member.

"I'm home." He texts. And immediately the three dots signifying that someone was typing popped up. But he quickly added, "I panicked and bought girl ones."
The three dots stopped for a second but immediately started again.
 
TexBB: Awww that would look adorable
Wishmebaby: It's not that bad.
DipFranks: Have you tried them yet?
MaddMatt: No... I just got home.
Wishmebaby: Wha- Try them!
 
That piece of wisdom followed by several more agreeing messages is what spurred Matthew to open the pack and take one out. It was all pink beside the brightly colored princesses dancing on the front. Setting it to the side, Matthew sighed and started kicking off his pants. His hands were already shaking as he opened the pull-up and started to step inside. Just like the commercial, the pull-ups slipped up his thin legs. It took a bit of maneuvering but soon it settled snugly on his hips.

Looking at himself in the mirror hanging behind his door, Matthew paused. The pull-up fit a bit tightly but if he used it he didn't think it would leak. For giggles, he took his phone and snapped a photo of him standing there, one hand on the phone and the other fiddling with the waistband. Making sure the photo didn't show his face, he sent it to the group chat.
His phone was quickly discarded. Using both his hands, Matthew felt up the Pull-up, pressing the padding into himself. The same rush of pleasure from back in the day came, but this time, with the pulsing of his dick. A flash of realization came over him...he could masturbate like this. With a shaky breath, Matthew stepped away from the mirror and grabbed his phone again. He bit his lip as he unlocked it and displayed the group chat by default.
 
Thatfatcat: That's cute
Wishmebaby: Aww
TexBB: Congrats bud
 
But something struck his attention. In the top left corner of the screen displayed a glowing red number 4. He had 4 private messages. Which was 4 more than he had before he sent the photo. Arousal momentarily forgotten, Matthew clicked over to his inbox. He found the 4 messages came from 3 different people. Clicking on the first, he almost dropped his phone in surprise.

Someone had sent him a dick pic.

Quickly, he blocked that person without replying. He never expected to get that kind of response. He never put much thought into his sexual orientation, mostly because he nor his parents cared. He knew that made him luckier than a lot of other teens, but still he never explored it. So while he wasn't much bothered by it being a man that texted him, what did bother him was the unsolicited nature of it. He clicked on the next one feeling less excitement than before.
 
DomBrady: Text me on QuickChats @DomBrady. I make videos disciplining sissies like you.
 
Immediately, another block. Matthew was offended by the onslaught of vulgarity that he almost just deleted the last message preemptively. After all, the track record wasn’t great. But, seeing no photos or links, he read it instead.
 
MaverickW: Hello, MaddMatt. I share the fetishist group chat with you and I saw your recent posts. It's great to see your first experience unfolding. I wanted to message you a proposal of sorts. I'd be interested in paying you for exclusive (meaning nobody but me would receive) content. And perhaps, if you felt comfortable with it, some requests as well.

The first message confused Matthew to no end, but it continued.
 
MaverickW: I'm fully capable of paying you for any correspondences from this point. I'd be open to discussing a possible arrangement with you. But feel free to ignore this message if you feel I've crossed a boundary.
 
Biting his lip, Matthew could not deny his curiosity. He even found his thumbs typing before he could stop them.
 
MaddMatt: What kind of content are you asking for?
 
The blue check mark rapidly turned green showing the message had been sent and read. And the three dots showed up just as quickly. Matthew waited with bated breath for the next message. He feared this person was much like the first. Only this time he feared they would want pictures of his privates. Although the promise of being paid was intriguing, he didn’t want them to end up in the wrong hands. 
 
MaverickW: Photos and/or videos. None of which you have to show your face in. I could make some requests, and then I send the payment in exchange for the media. We could have a small demo, of course, to prove I am legit. 
MaddMatt: That would be appreciated...
MaverickW: Excellent. Let's start with... Would you be comfortable sending me a photo similar to the one you posted in the group chat, but this time, having my username written on the mirror? In exchange, I'll send you 5 dollars on PaySmart? Or if you have another pay app in mind.
 
Matthew had PaySmart. He used it for his friends when they would buy each other food. Looking quickly, he saw that he had used the same username on the app rather than inputting his actual government name. It seemed handy for this.
 
MaddMatt: I have PaySmart. Let me take the photo.
 
Matthew set the phone down again and walked to his mirror with a dry erase marker. He wrote @MaverickW on the surface and grabbed his phone. Opening the photo app from the lock screen, he took a moment to pose. It was much the same as the one before, only this time, his hand was pressed against his stomach. Matthew meant it as a way to not block the sight of the pull-up, but it came out looking like one of the photos an InstaSnap model would post. He wasn’t so nervous about sending this one seeing as how he had already sent a similar one to the group chat. 

Sending it, Matthew wrote, "My user on PaySmart is the same as this one."

And he waited.

The sharp sounding DING from the PaySmart app almost surprised him signifying a payment.
 
$5 have been sent from Maverick W. for Photo
 
It was easily the quickest 5 dollars he had ever made. Going back to the group chat app, Matthew saw several messages waiting for him.

 
MaverickW: Your eagerness is endearing. But you don't have to send me the content before the payment is sent. Regardless, I've sent the payment. And I very much enjoyed the photo.

 
Attached to the message was a screenshot of the payment confirmation. Followed by another message.

 
MaverickW: Would you like to try some more? Same rate of 5 dollars per photo request?

Matthew's face reddened. He hadn’t thought that far ahead. 

MaddMatt: Sorry. I'm new to this whole thing. Thanks for not being a scammer though I guess... Yeah, I'd be up for more.
 
After all, it was a quick way to make money. At the very least, it could pay for his dinner tonight. And he could always block the guy if he made any outlandish requests. 
 
MaverickW: It's alright, Matt (If I can call you that?). I found it endearing. Good that you're up for more. For this round, how about three photos.
One, I'd like you to take kneeling in front of the mirror. Simple as that. The second request is a bit more complicated. I'd like you to put the phone on a timer and prop it up so that your hands are free. Same kneeling as before, but I'd like to see your hands flat on your knees. Lastly, I'd like to see your hand pressed against the front of your pull-up. Any way you'd like.
Are you comfortable with this? As soon as you tell me you have the photos, I'll send the 15 dollars payment and you can send me the photos.
 
Matthew's heart raced as he watched each message come in. And he blinked at the simplicity of the requests.
 
MaddMatt: I can do that. Give me a moment.
 
The first picture was easy enough. The second was a bit harder as he found himself having to turn around and flip the camera. He took a couple of pictures before he had one he was pleased with. For the final, he felt a blush journey down his chest. He took the photo in the same orientation except parting his thighs. And he raised his shirt to expose the pull-up. His free hand pressing against the front as he did before. Sitting down on his butt in front of the mirror, he turned his attention to his phone. Matthew deleted all the photos from before and emptied them from his trash, leaving only these three. Opening the chat app, he messaged the man back. 
 
MaddMatt: I have them.
MaverickW: Good job. I'm sending the payment now.
 
Like before, 15 dollars was delivered to his account. As easy as that. Wide-eyed, Matthew texted back.
 
MaddMatt: I got it. Here are the photos. 3 attachments
MaverickW: Very nice. I am confident in going forward with negotiations of this arrangement if you are as well?
 
It had all seemed so easy so far...Matthew hoped there wasn’t a catch. But he felt safe at the moment. This man didn’t have his real name. All he had were photos of his body. And he didn’t think he was special enough to have a recognizable body. Nor did he have any tattoos. He had already made enough with a handful of photos to pay for his dinner that night. And, maybe he was greedy, but Matthew wondered just how much the man was willing to pay him. 
 
MaddMatt: Yes.
MaverickW: Good. First off, I tend to give a lot of praise. And I use terms of endearment. Are those alright with you? If not, I will refrain.
 
Matthew didn’t think that was a big deal. Maybe a little strange, but harmless. 
 
MaddMatt: I don't mind. Do you want me to use any with you?
MaverickW: Only if you are comfortable.
MaddMatt: I don't mind. They're just words...Do you have any you want me to call you by? I have no preference.
MaverickW: Only if you're comfortable, I'd very much like for you to call me either Sir or Daddy.
 
Matthew blushed bright red, clutching his phone in his hand. Honestly, he wasn’t stupid. He met the guy off a fetishist group chat. And who else would ask for pictures of him showing off his pull-up and kneeling than someone with more than just the one kink. Plus the Sugar Daddy aspect was hard to ignore. But...Matthew was glad to be given options. 
 
MaddMatt: Yes sir.
MaverickW: Good boy. I am very pleased. You’re doing well so far.
 
Matthew didn't know what to reply to that but he didn't have to as Maverick replied again.
 
MaverickW: I'm happy with the standard rate of 5 dollars per photo. If you are comfortable with videos I would be willing to pay 10 dollars per 30 seconds. Unless, of course, there are elements that you feel require more?
MaddMatt: I'm good with that.
MaverickW: Good boy. And is there anything you don't want to do? Anything at all and I won't ask you to.
 
This was Matthew’s time to place boundaries. He was grateful for the opportunity. He didn’t want to get through all of this only to get his first request and have to back out. 
 
MaddMatt: I don’t think I want to show you genitals. Is that okay? I'll take my clothes off, but I don’t want to be naked. And I don’t want to show my face for now. Calling me Matt is fine, but I don’t want to share real names. 
MaverickW: That is more than fine, baby boy. Thank you for telling me that. You can always tell me no and I won’t hold it against you. And as I said, I'd like this to be exclusive. Between you and I. I would like to be your only client. Is that doable?
MaddMatt: Yeah of course.
MaverickW: Good boy. And I will never share your videos or photos anywhere ever.
MaddMatt: thanks
MaverickW: It's alright, baby boy. I think that’s all the negotiations for now, but we will have more as things come up...are you ready for another request?
 
Matthew took a deep breath. Everything had been easy so far. He didn’t think anything could trip him up at this point. 
 
MadMatt: Yes sir.
MaverickW: Good boy. I would like you to- 
 

To be continued...

[Kaleros]

Good start. The suspense of MaverickV's next request is killing me.

[BobbyDrago]

I like this start and I can't wait to see where you go from here.

[WBDaddy]

This is probably the first time someone started with a "payoff" (Main character in diapers right out of the gate) where I was interested in what happened after. 

Good job. 

[Lavellan]

Content Warning: Nothing vulgar. It's all good. 

 

Sugar for Baby: Chapter 2

 

MaverickW: I would like you to send me a video. One of you kneeling like before. But you don’t have to do anything but talk to me. Are you comfortable with that? Me hearing your voice?

Matthew had to take a moment to think about that one. Sure, he knew he would be asked to send videos but he didn’t focus on him speaking in them. He just assumed that this man’s fascination was with the pull-ups and less with himself. 

MaddMatt: What do you want me to say? 

Because that mattered. It mattered a lot. Matthew never sexted anyone before. He’s spoken in the crude way high school boys did from time to time. But something about this man’s request seemed to Matthew like he wanted something more sensual…

MaverickW: How about...you tell me about yourself. Nothing too personal. Or just tell me about your interests in diapers. Either one. 
MaddMatt: All in 30 seconds? 
MaverickW: Take as long as you want. I’ll pay for however long it is. 

Matthew blinked at his phone screen. That was...awfully generous. 

MaddMatt: What if I take 10 mins? 
MaverickW: I’d be very surprised if you could talk about yourself for 10 minutes straight. But if you somehow managed, I would still pay you of course. 
MaddMatt: That would be 200 dollars though. 
MaverickW: Which I am more than capable of paying. 

The three dots stayed on the screen meaning MaverickW was still typing. Matthew leaned against his door waiting. 

MaverickW: I am quite a wealthy man. I don’t mean that as a brag. I mean it honestly. I appreciate any concern you may have for my financial situation, but you don’t need to worry. I would not be offering an arrangement like this unless I knew I could handle it. 

Matthew could believe it. The man casually sent him 20 dollars for 4 photos. 

MaddMatt: Okay...give me a sec. 

Propping the phone up as he did before, Matthew set a 10-second timer. It gave him plenty of time to get into the kneeling position while also making sure his face was out of frame before the recording started. Even so, Matthew felt like a deer in headlights as the red blinking light told him the camera was rolling. 

“Um...hi.” He says awkwardly and shifts. The pull-up rustles between his thighs as he moves. “As I said, you can call me Matt. It’s part of my name...I’m 18 years old. I’ll be 19 in about a month.” 

It was hard thinking of things to say that wouldn’t give away too much information about him. “I joined the group chat a while ago. Everyone in there seems pretty nice. But this is the first diaper experience I’ve had since I joined.” He gently fidgets with the waistband of the pull-up. 

“I didn’t mean to get the girl ones. I was just nervous at the store.” Matthew parts his legs just slightly to expose the pull-up a bit more. “I’ve looked at the diapers online, you know, with the prints on them. I haven’t decided which ones to get. Plus, I think I’d need to open a PO box just in case I’m not home when it arrives.” 

Matthew caught himself slowly slipping out of the kneeling position and straightened up quickly. He placed his hands down flat on his thighs. “I like diapers.” He admits for the first time out loud. “I have for as long as I can remember. The prints on them, the way they feel when I put them on, I haven’t tried using them, but the idea is appealing.”

He fights down the urge to touch himself again as he clears his throat. He could go for a glass of water right about now. “It’s both a sexual and nonsexual interest for me. I have a feeling you’d like both in this arrangement? Or maybe just the sexual bit? I don’t know.” Matthew shrugs and figures that’s a long enough video. Leaning forward, he grabs his phone and presses the stop button before pointing the camera at his face again. 

There’s a moment where he scrolls through to video to make sure he didn’t show his face and sense that it’s fine, he sends a message to MaverickW. 

MaddMatt: It ended up being 3 minutes long.

Well, it was 3 minutes and 12 seconds. But Matthew wasn’t going to make MaverickW pay the dollar or so it was for 12 seconds. 

$60 has been sent from Maverick W. for Video

Matthew gets the PaySmart notification and immediately sends the video through. While he waits for MaverickW to watch it, he goes downstairs and grabs a bottle of water from the fridge. Almost half of it is gone by the time Matthew makes it back to his room. And it’s as he shuts the door behind him that he realizes he went downstairs with no pants on and a pink pull-up poking from under his shirt. He’s so very lucky his dad was staying out late. 

Checking his phone shows him several message notifications. Upon clicking on them, he sees several paragraphs and the three dots that signify MaverickW is still typing. 

MaverickW: You did very well, Matt. You seemed very shy but you worked through and kept going. I’m very happy with the video and I want to reply to a few things you said. 

I am 25 years old. I hope the nearly 6 years difference doesn’t bother you. I’ve been a member of the group chat for almost a year, myself. I mostly just watch, but if you search my username you can see some of my messages. 

I think you look rather cute wearing those pull-ups. Even if it wasn’t intended. There’s quite a variety of diapers out there. To find your preferred brand, there are sample packs that you can get online. And of course, it goes without saying that I would buy them for you if you asked me to. Even the PO box. That’s the sort of arrangement I offer to you. I’m sure you’re familiar with the term “Sugar Daddy”? It’s like that, although, a different kind of “Sugar”. 

You and I share the same feelings when it comes to diapers. Although I prefer to see others wear them, I rarely ever feel the urge to wear them myself. Thank you for sharing your preferences with me. I’ll make sure to remember them so as not to step outside your boundaries with my requests. 

Matthew lays down in bed before MaverickW is done typing. This MaverickW guy seemed nice, all things considered. Matthew didn’t wake up that morning thinking he would become a Sugar Baby by the end of the day. But it wasn’t entirely unwelcome. Pretty soon, the phone stopped pinging with messages, and he picked it up once more. 

MaverickW: I know it must seem like I’m coming on strong. Feel free to tell me so and I’ll back off. But I see a promising long-term arrangement ahead of us. Which means I’m an open book. Ask me anything. And barring any sensitive personal information, I’ll answer. I’d like to get to know you outside of the fetish as well, if you’d be willing. 

In the end, Matt, you have complete control over this arrangement. I may make the requests, but you have all the power to stop this whenever you want. No hard feelings. Do you understand? 

Matthew did understand. And he didn’t doubt MaverickW at all. If he never replied, Matthew believed MaverickW wouldn’t push him. And the invitation for open communication, not just about the diapers but about other things helped Matthew feel less like MaverickW wanted him because he just wanted someone to provide him pictures. 

MaverickW: Take some time to think, if you feel you need to. I have no more requests for today, but the invitation for questions is still there. I have a meeting in an hour that prevents me from responding, but I’ll reply soon after that. If you’re still awake.
MaddMatt: All that sounds very nice and I probably will take the rest of the night to think about it all. But I would also like to get to know you as well. It’s 2 pm for me right now. I’d be happy with messaging back and forth whenever we have free time for the rest of the night if that’s okay with you?
MaverickW: Of course, baby boy. It’s 2 pm for me as well so that works out well. 

For a moment, Matthew felt anxious at the possible proximity, but then he remembered that time zones stretch across multiple states. And MaverickW only knew a portion of his name and age. It wasn’t as if he were able to drive up right outside his door. 

MaddMatt: So... you probably can’t tell me where you work, but what kind of business do you do? 

Almost immediately, MaverickW started to type a reply. But Matthew suspected it would take him a second to reply, so instead, he went to a delivery app and started to scroll through. He had missed lunch in all the excitement of his purchase, so he was happy to treat himself (or more accurately, let MaverickW treat him seeing as how it was his money that was paying for it) to some Chinese. Normally he’d go pick it up himself to save on delivery fees, but this time, he didn’t bother. 

After placing the order, he sent a text to his father explaining that he would have food in the fridge when he got home. And right around the time his father texted him back, MaverickW finished typing. 

MaverickW: I work in a security company owned by my father. Mainly, I oversee the day-to-day goings-on in the office. It’s mostly boring stuff. I won’t bore you too much. On average, the most exciting thing I deal with is someone taking someone else’s lunch out of the fridge in the break room. Do you work?

Matthew spent the next few minutes explaining his tutoring sessions. He had a few regular clients that he’d been tutoring for years now, but most of them hired him for the semester or a single school year. MaverickW seemed impressed though and praised Matthew for even something as simple as that. He assured Matthew that of course, it was a job. Teaching was a hard profession and anyone who did so had to be very intelligent and patient. Especially to have repeat clients. 

In the end, as Matthew slipped some shorts on over his pull-up and went to get his food from downstairs, he had a smile on his face. But right as Matthew sat down in front of his desktop monitor to eat and watch a movie, MaverickW texted him that his meeting was starting soon and that he would text again when it was over. It left Matthew feeling a little disappointed, but he pushed that to the side in favor of his food and the movie. 

About halfway through, however, a mischievous thought passed through Matthew’s head. The food was basically from Maverick. The generous tip he gave the delivery driver was because of Maverick. And Matthew hadn’t even thanked him for it. No, Maverick thanked him for a 3-minute video… 

Matthew propped the phone up on his desk and pushed his chair back. He kicked the shorts off and raised his shirt just enough to expose that he was still wearing the pull-up. With one leg, he propped it over the arm of the chair. He held the container of rice in front of him casually. A small giddy grin took up his face as he activated the timer and did some last-minute adjustments before the picture was taken. 

Pushing himself back up to the desk, he scrolled to the camera roll and pulled up the photo. Seeing his smile captured in the photo, he went to crop it out, but right as he was about to, he paused. 

It was just his smile. Not even his nose was in the photo. Other than that, the only thing that could be seen was his dark brown hair poking from behind his ear. It wasn’t that obvious. Eventually, Matthew decided to save the photo as it was and sent it to Maverick’s inbox with the caption ‘Thanks for the food Sir.’ and a smiley face emoji. 

He knew Maverick wouldn’t see it until after his meeting, but the anticipation for a response was still there. Finishing his food and the movie, Matthew stood and stretched. He had finished his water a long time ago and was now feeling the need to use the bathroom. Still, he didn’t know if the pull-ups would hold completely. Deciding to play it safe, Matthew walked into the bathroom. Technically, the bathroom was out in the hall, so it wasn’t his private one, but he only shared with guests if they had any. 

Taking a breath, Matthew took off his shirt and stepped into the shower. It was cold in the bathroom and he immediately got goosebumps as he leaned against the cold glass of the shower. Matthew closed his eyes, leaning his head back as well, he forced himself to relax. All the experiences he’d ever read talked about how hard it was to suddenly let go when not near a toilet as if the body knew that and refused to let go. 

He felt that then as if there were a block on his bladder preventing it from releasing. Feeling annoyed by it, Matthew reached down and felt for where his bladder was bulging out slightly. Pressing on it made his need that much more insistent, and he even felt a small trickle leak out, but it stopped as soon as he eased up his hand. Still, the pull-up soaked up the few drops of urine easily. 

He tried a new approach. Instead of leaning back into the glass, he stood up, imagining a toilet right in front of him. One hand reached down to cup the front of the pull-up as if it would simulate him pointing himself at the toilet. Again, he closed his eyes and tried to relax. This method seemed to work better as he was able to get a full stream out. Fearing that flooding the pull-up would make it leak quickly, he forced the stream to stop. Matthew’s bladder protested. 

The front of the pull-up was much warmer now, and he could feel the material swell slightly just to accommodate. Only when Matthew was sure the pull-up had soaked up everything, he let go again. It was much easier this time. 

Like before, he tried to stem the flow so as not to flood the pull-up, although it was much harder somehow. You would think it would be easier seeing as how his bladder was emptier, but it wasn’t. Struggling, he finally managed to stop pissing, a small whine escaping him from the urge to grip his dick. He felt that close to the dam breaking. But even with a hand outside the pull-up, he could feel the material struggling to absorb it all. The front of the pull-up swelled to max capacity, and he could feel it trying to leak towards the back. Matthew leaned back against the glass again, now confident that he could release. The only problem was stopping. 

As he let go this final time, Matthew knew there would be no stopping. With a forceful hiss, Matthew started to wet his pull-up in earnest. Almost immediately after, Matthew felt the telltale feeling of warmth trickling down his leg. With a sigh of disappointment, he had no choice but to let it all out. The sound of urine flowing down the drain was deafening and embarrassing.

Eventually, his bladder was empty and the stream stopped. The pull-up sagged between his legs and a spurt of piss dribbled down his leg every time he moved. Matthew reached for the side of the pull-up and ripped it. Same for the other side. The pull-up was heavy in his hand and he set it down on the floor of the shower, before turning the shower on. 

Matthew ducked out of the way of the initial cold spray, settling back under as it warmed up. He made his shower quick but paid special attention to make sure he washed away all traces of urine on him. As he got out of the shower, he wrapped his towel around his waist and went to his room, leaving the pull-up on the floor of the shower for now. 

He didn’t go back to the bathroom until after he had put on underwear and pajama pants and grabbed one of the shopping bags from before. Putting the used pull-up in the bag, he tied it tight and threw it in the garbage outside. Finally back inside, Matthew grabs his phone from his desk and sees a handful of notifications. Before he checks them, he goes to flop on his bed. 

The first 3 notifications are from the group chat, miscellaneous people talking small talk that he didn’t feel like indulging in right now. But what caught his attention was a notification from PaySmart. 

$20 has been sent from Maverick W. for Breakfast.

This made Matthew sit up quickly, immediately clicking on the last notification, seeing it was a message from Maverick five minutes ago. 

MaverickW: You are more than welcome, baby boy. I needed the smile after such a boring meeting. It brings me great pleasure to take care of you even in something as simple as a meal. I’m sure you’ve gotten the notification from PaySmart already. I’d like for you to buy yourself a nice breakfast tomorrow morning as well. Or, if you’d like, spend it on something else. My point is that I enjoy caring for your needs. Have you ever heard of an app called Treat Me? 

Immediately, Matthew started typing. 

MaddMatt: I sent the photo as thanks, but I didn’t expect anything in return for it...Thank you though. I’ll be sure to go get some pancakes or waffles tomorrow. I haven’t heard of that app actually. What is it?

Even as Matthew asks, he goes to his app store and looks it up. 

Treat Me is a brightly colored app that seems to advertise itself to streamers or influencers. Its main objective states that it is “a way for viewers to send their appreciation in a more direct way to their favorite content creator. Completely anonymous and confidential for personal information.” 

That’s also the jist of Maverick’s explanation as well. 

MaverickW: You can attach things like a wishlist, or you can set up a meal request. Your viewer (me) can pay for them immediately and those things will be delivered to you. 
MaddMatt: And you’d want to do that? For me?
MaverickW: Of course. Matt, in most arrangements like this, the “Sugar Baby” gets a weekly allowance to spend as they please. I have a feeling you would be overwhelmed with something like that. So, something like this is a good compromise. 
MaddMatt: If you’re sure. 
MaverickW: If it makes you feel better, my motivations aren’t completely selfless here...I admit it does allow me to make sure you’re taking care of yourself. After all, if I bought you greasy take-out every night, that’s not exactly taking care of you, is it? 

Matthew felt his face heat up at that. It was true at least. 

MaddMatt: This feels like a lot.
MaverickW: Too much?
MaddMatt: Well...idk. I feel like I should be doing more for you though. 
MaverickW: You’re new to arrangements like these. We started slow. Eventually, you’ll do more and more in exchange. But it’s your comfortability that matters most. 

Looking back, Matthew wasn’t sure what possessed him to do something like this, but his fingers type faster than he can second guess himself. 

MaddMatt: Give me another request then. No money. Give me something to do to repay you so I don’t feel like I’m taking too much. 

For a few agonizing moments, nothing happens. Not even the dots signifying that Maverick is typing. For a moment, Matthew fears that he’s crossed some sort of line by making demands. And he’s halfway through typing an apology before the three dots rapidly appear and a message comes in a second later. 

MaverickW: Alright then…

Matthew gives a heavy sigh as the dots reappear and stay until another message comes through. 

MaverickW: I’m going to call you through this chat. And you’re going to talk to me on the phone. I’ve heard your voice before so this should only be a slight adjustment. Is that alright with you? 

Immediately it felt like an 808 drum was beating in his chest. Matthew expected something like another picture or another video or something. But this was simultaneously much easier and harder at the same time. Even so, Matthew asked for it. 

MaddMatt: Yes, sir. 
MaverickW: Good boy. 

A second later and Matthew’s screen lit up with Maverick’s icon and the text “MaverickW is Calling.” Matthew cleared his throat, hands shaking as he reached up and tapped the green check button to accept the call. 

Putting the phone to his ear, Matthew heard nothing. 

“H-Hello?” He stuttered, hand fisting in his sheets. 

A deep, purr of a voice came over the line. “Hello, darling.” The voice cooed so smoothly as if it had said it to Matthew a thousand times before. Matthew felt a breath catch in his throat. 

[BobbyDrago]

Dam that last line. You can tell he's someone with experience in these matters, with a statement oozing confidence like that.

[Little Baby Becca]

Hmmm...

[Lavellan]

2 hours ago, BobbyDrago said:

Dam that last line. You can tell he's someone with experience in these matters, with a statement oozing confidence like that.

I'm glad I portrayed that correctly! 

 

15 minutes ago, Little Baby Becca said:

Hmmm...

Oh?