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Nine.

It was 7:30 PM on the dot, and we both arrived at Maxwell’s at the same time. We had anticipated our first meeting being at the bar - a moment we had predicted would be a little awkward due to the lingering question of whether or not I had actually worn a diaper to our date.

But we practically ran into each other on the sidewalk in front, and with a quick glance in all directions to confirm that we were out of range of curious eyes, Lucy chose her first words to me carefully:

“Are you going to spin around so I can determine if you’re wearing a diaper or not?”

I felt my cheeks flare. “Here?”

“It’s either here or inside Maxwell’s. I’m going to guess you’d rather have me check here.”

I nodded, spinning around to face away from her without another word. She quickly pulled open the back of my pants and took a peek to see what was there. She wouldn’t be disappointed. With a single smack to my ass, the sound of the plastic padding ringing clear, her inspection was complete.

Spinning back to face her again, I had a more ample chance to get a look at her. And she looked amazing. More importantly - I felt that the photos on her online profile had done her justice. Her shapely body. Her thick brown hair that seemed to explode in every direction. Those lips.

She simply seemed too amazing to be real.

“You’re cute,” she said, beating me to saying it first.

It might have come off as some sort of bashful aw shucks act, but my reaction was genuine. “Oh I don’t know…”

“Boys are notoriously terrible at taking selfies for dating profiles,” she said.

“You’re probably not wrong,” I said. I liked that she used ‘boys’ instead of ‘men.’

“Let’s get some drinks,” she said with a smile. “I’m thirsty.”

“Yeah...me too.”

Did she wink at me? I swore that she winked at me.

“When we go in, do I ask them for a baby bottle for you?”

“Are you going to do this all night?” I asked.

“Oh, most likely.”

I was really happy to have heard that.

I followed her inside, and she found some seats at the far end of the bar. The place was far from busy, and so it felt like our seats were practically in a private room. Probably for the best.

We ordered some drinks. I went with a Maker’s manhattan in the hopes that she’d be impressed by my classically manly taste.

Instead, she asked me, in front of the pretty young woman tending the bar: “Are you sure? Not a sippy cup of milk? Some apple juice.”

The bartender seemed willing to accept that it was just an in-joke that she wasn’t privy to, but there was no doubt that she could see the humiliation Lucy’s words had caused me. Thankfully she laughed it off and prepared the more adult beverage I actually requested.

“You’re a handful, I see,” I said to her.

“Just having fun,” she said. “But what about you? Are you a handful?”

It was a surprisingly hard question to answer. Most of my diaper-baby fantasies had only ever taken place in my mind.

“Can I be honest with you?” I asked.

“I’d prefer that,” she said with a smile.

“I’ve never been...a baby. For someone else.”

She shrugged and nodded, showing no concern for this whatsoever. “Well then I think you should have that experience at least once. Don’t you?”

I nodded. “But… Not with just anyone, you know? I dunno. I guess I could’ve paid for whatever it was I wanted at any point. But I didn’t want that to be my experience.”

“I should be upfront with you,” Lucy said, sipping her just-delivered daiquiri, “people have paid me in the past for just that sort of thing.”

I nodded. I braced myself for the wind to be completely taken from of my sails. She was perfect in every way...for the right price?

“I’m not looking for clients,” she added - probably seeing the look on my face. I could tell that she had more to say about it, but I let it go. I had just learned a bit about her, and none of it upset me.

“I don’t know what I’m looking for,” I said. “If we’re being upfront. Yeah, I guess it would be nice to meet this amazing person who checked off all the boxes and was a kink-lord of some sort, but...I don’t know. I feel like whatever I’m chasing...I wouldn’t know what to do with it when I got it.”

“That’s not the worst thing,” Lucy said. “It just means you’re willing to put yourself out there. Experiment and try new things, right?”

I nodded. “Yeah.” I had never thought about it like that, and I appreciated how she helped me see it differently.

“I’m in a similar predicament,” she said. “The thought of another long term relationship is just exhausting to me. But, you know, if you throw a word like ‘casual’ around, suddenly everyone wants to treat you like a disposable fuck doll.”

“Guys are the worst,” I muttered.

“Oh, it’s not just guys though. Everyone does it.”

“You’re…”

“Bi? Yeah,” she said with a nod. “Are you straight?”

“Curious, at most,” I said honestly. I had no experience nor previous encounters that I could use as evidence for such a claim, but surely pure curiosity counted for something.

“Anything in particular that you’re curious about?” The little grin on her face suggested that she just wanted to make me say the words. I liked it.

“Oh...I’m sure my curiosities run the gamut from the most mild of interactions to…”

“Getting bent over so that a cock could slide into your bottom?”

I blushed, quickly taking a drink of my cocktail to shake off how flustered I had become.

“I’m teasing, I’m teasing,” she said with a laugh. “I have to admit. It’s kind of cute to watch you get all antsy.

“This is nothing,” I said. “I can get real antsy.”

Her fingers tip-tapped their way across the bar’s counter towards my arm, and when she reached it, she let her fingertips gently glide over my skin. My arm hair stood on end and I felt goosebumps rise across my body.

“So, the married life, huh?”

“It’s something,” I replied.

“You used the word ‘complacent’ the other day. It doesn’t exactly instil a feeling of confidence in your marriage.”

I was more blunt about the topic than I thought I’d be: “She’s seeing our neighbor - another woman. And she’s - our neighbor - she’s...incredible. And...I don’t know. Maybe if it was any other woman in the world I’d feel better about it. But this woman…”

“So you wish it was you?” Lucy said with a shrug. She was either very perceptive, or my tone and wording had made it incredibly obvious.

“Yeah.”

“What’s that quote?” Lucy asked, as if speaking to herself. “You miss 100% of the shots you don’t take?”

Lucy might have been right about everything else, but the situation with Ashley was more complicated than that. The diapers and the ageplay with Veronica and...the fact that we had made out that one night. I had somehow almost forgotten about it, and the very thought of it while in the bar still managed to get my heart pumping a little faster.

“I think that quote is missing a key piece of logic,” I said.

“Oh?”

“You don’t want to take every shot, right? Not every shot is worth taking.”

“Hmm,” she hummed, barely concealing a smile. “I’m not sure you get the spirit of the original quote. But that was cute, I’ll give you that.”

“You’ve alluded to having cared for some babies in the past,” I said, hoping to change the topic.

“A few.”

“And how did that come to be?”

She smirked. “Someone took a shot.”

“Care to elaborate?”

“I’ve always been a very ‘try-anything-once’ kinda gal, you know? I wear that on my sleeve. It tends to attract people whose interests fall a little outside of the norm. Or, maybe, I just have the personality that helps put them at ease enough to talk about these sorts of things.”

“Could be both,” I said.

“For sure,” Lucy said. “And so I was seeing this guy. Francis. He just sort of unloads all this on me one night. I think he had bad experiences in the past with telling girlfriends that he wore diapers and it had always ended poorly, you know? So this was an attempt at being upfront with me. Except he didn’t work it into a natural conversation. We were just watching Jeopardy and suddenly he was telling me about how he wanted to crawl around in a diaper.”

“Wow. So...how did you react to it?”

“I was like ‘Ok cool. Let’s do it.’”

“It was that easy?”

“I’m exaggerating a tiny bit, but yeah. At the end of the day, I was either going to be curious about it or reject it. And it was new to me, so I wanted to see how it played out.”

“And how did that go?”

“I loved it,” she said. “Absolutely loved it. I was like a pig in mud. It just fit me, you know?”

I nodded. I liked hearing her say that.

“We broke up. Not because of that. Just other incompatibilities, I guess. But he kept reaching out to me. And it wasn’t because he wanted to get back together again.”

It seemed obvious to me: “Because he wanted you to treat him like a baby.”

She nodded. “Basically. And, I don’t know, that doesn’t seem like the kind of thing you can do for just anyone - let alone an ex, you know? But I wanted to experience that mommy role again. So I tossed out the idea of him paying me for it. And he went for it. From there, I guess a little side hustle was born.”

“But you like doing it. Still?”

“Oh yes,” she said. “Love it. Except, now, I’d like to do it with someone I actually had a stronger connection to.”

I felt myself blushing. I wasn’t even sure why. We certainly didn’t have that connection yet - even if I so badly wanted it. Maybe it was just the fact that the possibility seemed real.

She reached across my leg under the bar counter, feeling the padded bulge between my legs. “How are you doing in there anyways?”

“Fine… Good.” I felt myself grasping for the response she might be looking for. “Dry.”

“Still? That’s a shame.”

I laughed - my cheeks had to have been a deep magenta color at this point. “Did you really expect me to wet myself here at the bar? In front of you?”

“Yes.”

Her answer didn’t surprise me, but I admired her blunt retort.

“How many more drinks will it take to make that easier for you?” she asked.

“More drinks would certainly make it easier,” I said. “But I could do it without the assistance.”

“Well then, you just tell me when you’re going to go.”

“You want me to...tell you?”

“Absolutely,” she said with a nod. “The moment it's happening, I think you should tell me so.”

“Okay,” I said. It was hard not to smile. I was feeling a little giddy - I never had someone talk to me like this - about this - before.

As effortlessly as she had got us talking about diapers people who were treated like babies, she steered us to lighter topics. The best tacos in the city. Rainy day music. Her love of clowns vs. my hatred of them. The best Kubrick movie.

We clicked, and it felt like we just kept clicking with every new topic. Even when we didn’t agree on something, it felt like a bonding opportunity anyways, with each of us eager to hear the other out on why they disagreed.

Somewhere in the middle of a lively discussion about the preferred preparation of eggs, I interrupted her with a very important statement:

“I...I’m wetting myself. Right now.”

“I don’t suppose you brought a change of diapers with you, hm?”

“No…”

“How unfortunate.”

“If I had, you would’ve...changed me?”

“I’d have wanted to,” she said with a nod. “I’d have wanted to put you up on this bar counter and change your diaper right here in front of anyone who’d care to watch. But, also, I was just more concerned about your bottom. It might be a while before you go home. I hope you don’t get a rash.”

My imagination was drowning with visions of what she had just described. I was sure that she was just speaking hypothetically. Right? Her comments about diaper rash drifted right over my head.

“Maybe next time,” she added.

“You think there should be a next time?”

“I’d like there to be,” she said. “Wouldn’t you?”

I nodded. “Yes. Very much so.”

“And you’ll wear diapers again for me?”

“If I’m being honest, I’d probably do just about anything you told me to.” I didn’t mean to blurt out such a desperate thing. But her laugh suggested that she didn’t think too negatively of it.

“Be careful. That’s a dangerous thing to tell me.”

I decided to roll with it and double down. “Try me sometime.”

“Don’t play games you’re not prepared to lose,” she said. “I’m feeling pretty confident I could have you squatting down next to my barstool while you push a big mess into your soggy diaper.”

I laughed, but she had definitely deflated me a little. I wasn’t sure which concerned me more: that she’d actually request such a thing of me - or that if told to do it, I probably would.

“Okay, you win,” I said.

“Oh, but you win too.”

She was certainly right about that.

Another round of cocktails was delivered. We teetered back and forth between talking about kinky things and more everyday things.

The necessity of coffee in the morning.

Did I ever use a pacifier?

The worst highways in the city.

Enemas.

The last time we actually bought a magazine.

Getting bottle-fed.

Another round arrived. Maybe another after that - though the details got a little fuzzy around that point.

Eventually her hand landed on my crotch to feel my soggy diaper through my pants - and it just remained there after. The conversations got a little less civilized and a little more flirty. Her fingers would occasionally squeeze the lump in my pants playfully.

In a buzzed fog, we kissed each other for a moment on the sidewalk before we split and went in our own directions.

The closer I got to home, the less real the entire night seemed. It was everything I wanted and needed and all I had to show for it were some foggy memories and a sagging diaper.

It was time to go back home to reality. Back to whatever it was that Veronica and Ashley were doing. Back to staring at my phone for the next message from Lucy.

By the time my key was in the door, I was daydreaming about playing with myself while thinking of squatting over the bar’s floor next to Lucy’s barstool as I pushed a firm load into my diaper, regardless of who was watching. I could already feel myself growing stiff from the thought, and I was looking forward to acting on this.

But no sooner than the door was opened, I was faced with Veronica and Ashley on the couch. Smiling. Waiting.

“Welcome home,” Veronica cooed. “You’ll have to tell us everything.”

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