The Pool Party: A Mommy and Baby A Story (Patreon)

He told me there was no way I could humiliate him.

I cocked my head to the side slightly at that remark and leaned back in my chair. The young man, with slightly graying hair for a 32 year old, was looking at me from over his computer screen as we negotiated the next scene we’d do together about a month from now.

“Are you sure?” I asked sweetly while looking into my computer's webcam. “There’s nothing I can do to humiliate you?”

“I mean… within the realm of safety of course. You know, our negotiations.”

“Well, sure,” I smiled again. I didn’t tend to smile with my teeth. I preferred a shy smile, one that left everyone guessing if it was genuine or not. Besides, my brain was moving.

We had agreed on several things during negotiations.

First, he was to use the safeword “umbrella” if we ever felt we had gone too far. We also used the typical green, yellow, red system. From our last few play sessions, I knew he never used the safewords. He saw it as a point of pride. I saw that as slightly reckless and made to check in often.

My goal was to get him to cry red this time. Bonus points if I could get him too umbrella.

The second rule we had was that when he was with me, he was to follow all of my instructions. I told him that I would never do anything that would jeopardize his safety. I’d never hurt him. As the dominant in this relationship, it was my job to protect him and keep him safe.

It was my sacred obligation.

I had no patience for doms who radiate this personality that the people who serve them are worms just waiting to be drained (cum or financially). It wasn’t how I did things.

No, I saw my throne not as a divine birthright, but as a pedestal to be earned. One that my babies give me willingly, as long as I protect the kingdom, they serve me.

The third rule was that when he was in my space, he would be wearing diapers.

That meant whenever he was in my presence, in my house, in my car, he would be diapered.

And he knew that it would be in his best interest to put on a diaper before he saw me. He knows that if I have to diaper because he was wearing silly big boy underwear, he’d be getting whatever I kept in my car or purse at the time.

He learned this the hard way.

***

The pool party at Trowl’s Rooftop was one of the events everyone looked forward to every single year. The owner would bring a remarkable DJ, dancers, lasers and all sorts of amazing food for an all night rager that was the party of the season.

This party had everything. You had the old guys trying to coax the young girls to the cabanas with the promise of free drinks if they’d just let “grandpa enjoy himself a bit.” An unfair exchange really. The bottle was at least $500. You can do better than Grey Goose sweetheart.

You had the young girls there, wearing their skimpiest bathing suits designed to remind their boyfriends that they should be the center of their attention, while the young guys were busy trying to keep their stomach and ass tight while they clowned around, pointedly ignoring their girlfriends peacocking.

No one wanted to look like they were drooling over their partners, but they so desperately wanted the attention.

That was how this all worked.

You also had the kids who had stumbled into the party who were there to splash around and have a good time. These normal people who were better adjusted than the average recovering mid life crisis jock turned used car salesmen, generally had more fun at these parties.

They didn’t leave crying most of the time.

They were drama free.

I am not drama free.

But when I walked up the steps, in my bright white bathing suit and white sarong that flapped gracefully in the slight breeze that wafted over the pool, my girlfriends and I looked around and smiled. The DJ was on fire. The lights were flashing. The dancers, both male and female, were shaking their hips, moving their legs and grinning to the crowd.

And there he was. My baby.

He was standing… no leaning next to a young woman who lightly grazed his lower navel with her fingers as she laughed at something he had said. The brown haired woman who couldn’t be more than five foot two held a beer in her hand and looked up at my baby, smiling and laughing a wide, jaw breaking grin.

No shy smile there.

He laughed at her joke and gave her a playful push on her shoulder. His hand lingered.

As I took my spot with my girlfriends in a cabana we had rented for the party, I inspected my baby from across the pool deck. He had an open button up and a pair of swimming shorts that hugged his quads. I narrowed my eyes slightly.

There clearly was no diaper underneath those shorts.

I glanced at my cell phone and scrolled back up over the text messages I had sent earlier in the day from when I first asked him if he’d be at the pool party.

Baby: Yes. I was planning on being there for a few hours. What’s up?

Me: Oh great. My girlfriends and I are going.

Baby: Oh cool. See you there?

Me: Only if you are going to follow the rules.

There was a long pause in his texting after I sent this last note. I was shaving my legs at the time and stared at the phone expectantly. I watched as the bubbles popped up and vanished a few times and smiled. He knew what I was talking about.

Me: And what are the rules?

Baby: Maybe not today?

Me: Are you planning on being a naughty baby today?

He was quiet again. For about five minutes.

Me: So you’ll be wearing your diapers to the party when I see you.

Baby: Yes.

Me: And you’ll submit to the diaper check?

Baby: Yes.

Me: Yes?

There was this long pause as I no doubt suspected he was struggling with his internal demons.

Baby: Yes mommy.

Which is why, right now, as I inspected his swim trunks from across the pool and only saw him, just him and now crinkly slightly bulging plastic, I was disappointed. He had promised me he’d follow the rules.

That was our agreement, our compact, our promise.

I told my girlfriends that I’d need the cabana for the next hour and they gave me a knowing smile. They didn’t know what it was exactly I did with the boys in the cabana. But they knew that I had several young men who would come by and visit for some fun.

Besides, I paid for the cabana. Complaining wasn’t going to get them further than a credit card.

I put my large white floppy hat back on and made my way to the other side of the pool.

I could see the young men watching me as I walked on the edge of the pool. I take care of myself, my soft brown skin glowed slightly amber in the sun and contrasted nicely against the sun.

Sweat caused my body to shine.

About halfway around the pool he noticed me and froze.

I could see what was going through his mind. Was he going to say red, was he going to umbrella? What was he going to do? He had told me there was no way he was backing down. He could take whatever I gave him.

I guess today we would find out.

Before he knew it, I was standing right next to him.

I exchanged hellos with him and his friends who didn’t even hide their staring. Carlos, his best friend, was suddenly rubbing the edge of his swim shorts slightly. I had that effect on people. All white is always a bold choice at the pool party.

“You look good,” I told my baby who quickly took a quick sip of beer and was looking me up and down.

“You too.”

I smiled the shy smile. “Thank you.”

I then leaned in and whispered into his ear, while squeezing his diaperless bottom. “Where are your diapers?”

He didn’t exactly jump at that sentence, but he did drop his beer, causing that short woman from earlier to jump backwards and shriek. His friends, now slightly preoccupied, helped her out while another scooped up the now fizzy can.

“Can we not?” my baby asked, clearly flushing a bit. He had this slightly hardness in his voice.

It’s always hard to tell if he’s blushing or not because of his dark skin. But his broad shoulders had slumped slightly, a somewhat good indicator of his feelings.

“You know what you have to do to get out of this,” I smiled and looked him dead in the eyes. I could see his face was scanning the pool party, trying to figure out if anyone was overhearing the conversation. His friends were still obsessing over the short girl with the bouncing tits in the green bathing suit.

She was enjoying the attention.

“I just think…”

“Hold on now baby,” I said, fingering the front waistband on his shorts. “You know what happens if you say the safeword.”

He nodded.

“Do you want to tell me, baby?” I drew out the last word with a slight, mocking husk in my voice.

“I can’t see you for three months.” He hissed.

“Exactly.” I smiled. “So what do you want to do?”

I watched his brain continue to run the gears, do the calculations in his mind.

Some of you might think that this rule was harsh. Safe words should be consequence free, a way to stop a scene that’s making you uncomfortable. I agree with that. But the reality is, I require a grace period afterwards so my babies can access if this relationship is right for them. Nothing like 90 days of diaper free, mommy free, clarity to help them decide on this issue.

“Fine,” my baby said.

“Fine what?”

He nearly stamped his feet. I saw his leg twitch.

“I want my diapers mommy.” He refused to make eye contact.

“Good boy,” I said. “Tell your friends you’ll be back. You aren’t leaving for a few more hours. You’ll have your crinkly protection on after all.”

***

The walk back to my cabana went by quickly for me, but I’d have to imagine that for my baby, it was a long walk. It was simultaneously walking the green mile, while speeding down a path of light towards a stargate. Somehow, his mind was breaking physics, speeding up while taking forever to accomplish this task.

Once we reached the cabana, I closed the curtains and told him to lie down.

It’s funny, because the curtains do provide a very good level of privacy, but if the breeze were to blow too hard, someone who was standing in the right spot might see what’s going on.

All the more reason to hurry.

I was not going to hurry.

I pulled off my baby’s pants and softly folded the swim trunks. They’d sit at the edge of the cabana until I told him he could put them back on. I inspected my baby, pulling his shirt up so I could see all of him.

“It looks like you’ve done a good job shaving.” I observed, while inspecting his penis with my hands. “Good boy.”

I pulled out the diaper bag I had brought with me and handed him the Trest diaper to hold onto. The diaper, bright white and crinkly, looked odd in this very adult setting, but Baby didn’t say anything. He knew better at this moment.

He was breathing quickly.

It was probably the excitement of what was about to happen.

It was probably the fear of what was about to happen.

The music and voices outside continued.

I handed him the baby lotion and powder and told him to be mommy’s good boy and hold on to these things while I did my work.

I started with the bottle of baby lotion. First, I placed a dollop of it on my fingers and began to massage it into his penis, his balls, the crevices down there. I always took my time at this part because I knew he’d react. Sure enough, within a few moments, his pee pee was growing and getting excited.

“Looks like someone is excited for his diapers,” I said quietly over the thump thump of the bass outside. “Makes you wonder why you weren’t wearing them when you got here.” I looked him in the eyes. “Do you want to tell mommy how excited you are for your diapers?”

He was quiet.

So I asked louder this time.

He responded quickly after that.

No doubt, he didn’t want to risk everyone hearing him make his infantile confession.

I reached into my bag and pulled out an overnight booster and made sure my baby could see me while I worked. “Can you hand me your diaper please?” I asked sweetly?

He complied.

First I fluffled out the diaper, rubbing it between my hands to get it nice and poofy. Next I folded the overnight stuffer in half and lined it up on one end of the leak guards. The stuffer then lay perfectly against the leak guard.

My baby's eyes bulged as I pulled out the second stuffer and did the same, but on the other side of the leak guards.

“Hold on a second,” he started to protest.

“No, you don’t get a say in this,” I said, smacking his bottom and having him lift up. “You could have chosen what diaper to wear today, but since Mommy had to decide, this is what you’re wearing.”

As he put his bottom down, I pulled the diaper up between his legs and began fastening the tapes. Because of the leak guards positioning, the diaper looked like it was already full, something that was painfully comical to me. The diaper was thick and bulging and would only get thicker as the night went on. Those overnight stuffers were as thirsty as a fish.

After the diaper was taped snug, I had him stand up so I could check the fit.

It was funny, seeing the front waistband against my baby’s abs stand out.

The diaper bulged on all sides and contoured nicely against his legs. It made his bottom look round and full. Someone might think he actually worked out at the gym.

“Okay baby,” I said softly, positioning myself on the cabana and reaching back into the diaper bag. “Time to finish the last part of your punishment before I let you back outside.

When he saw the two bottles, he looked like he wanted to cry. But his shoulders slumped, he climbed back into the cabana and I placed him so he was lying down in my lap and he began to suck. I patted the front of his diaper as he drank, encouraging him to be a good boy and finish his bottles for mommy. As he drank, I’d pull the bottle back from time to time, to make him work for it. He grumbled, but I just told him that good babies finished their bottles like good boys and put the nipple back into his mouth.

Also, the pats on the front of his diaper sure didn’t hurt.

Finally, he was done and I put away the supplies.

“Can I put my shorts back on mommy?” he asked softly, looking around nervously as the cabana curtains started to rustle in the wind.

“We just have to do one more thing,” I grinned, reaching into my bag. I pulled out a bottle of baby lotion and massaged it into his chest and back. He’d smell like a baby while walking around this party, reminding him of his status.

Once I was finished, he pulled up his swim shorts, shorts that now fit tighter and waddled out of the cabana.

Next time, he’d wear his own diapers like a good boy. Otherwise the swim shorts would be optional…

***