Night Games (Patreon)

He sighed, but he couldn’t help from grinning ear to ear. This was how it started. This was always how it started. He had been minding his own business - honest to god, this time he really had been - and somewhere around the halfway point of his bourbon and soda, this brunette was giving him the eyes.

The eyes. Oh, he’d know the eyes anywhere. They were flirty, but not too flirty. The trick was to blend in a little bit of disinterest. He was supposed to be kept on his toes. Was she flirting, or was he just imagining it? Some were much better at the eyes than others. This one? Oh, she was good.

It was his turn to make a play. He glanced away from her, as if he hadn’t even seen her. He looked deep down into his rocks glass, spinning the ice a little, as if he needed a better view of the universe hidden at the bottom of it. He’d glance up once in a while, checking the TV or looking at who was coming through the door. From his peripheral, he’d keep tabs on her. Her head was down. Her head was up. She was looking at him. Her head was down.

He looked back into his glass again. The ice spun around.

“I’m guessing this seat is not taken.”

It was her. Of course it was her.

“Maybe they’re not here yet?”

“When they get here, I’ll move.”

He laughed. He liked her.

“What are you drinking?”

“I have terrible taste in cocktails. If it was up to me, I’d just keep ordering cosmos all night.”

“Do you like cosmos?”

She shrugged. “Are you a man who knows his vices? Maybe you can order something good for me?”

He flagged the bartender over. “Manhattan? With Makers.” He turned back to her. “This is your graduation to the exciting world of adult beverages.”

“How old do you think I am?” she asked.

“23?”

“24,” she said with a wry smile. “I’ll take it.”

“How old do you think I am?”

“40...45?”

He laughed. “What made you suddenly add five years?”

“Because you remind me of my father.”

“Of course I do,” he said, taking a sip of his cocktail.

Her cocktail was delivered then too. She took a sip of it, while he watched her eyes. She stared back. If any part of her was disgusted by the drink, she wasn’t showing it. Of course, he also assumed that this wasn’t her first time at the rodeo. She probably drank more top shelf bourbon than he did.

“Can I be straightforward with you?” she asked.

“I’d like that.”

“I’m in town for the night and I was hoping to find a nice guy I could call Daddy.”

His eyes widened and he nodded slowly. This was a new approach.

“Just going to come out swinging, hm?”

“What do I have to lose?” she asked with a shrug. “If it’s not you, it’ll be someone else. Maybe that gentleman over there?” She motioned towards another man sitting at a table by himself. He certainly wasn’t a bad plan B.

“No need to get competitive about it. I didn’t say no.”

“I’m a handful,” she shrugged. “Are you up to the challenge?”

“I’ve dealt with my share of young ladies before.”

“But what if I wasn’t like them?”

He laughed and shook his head.

“What? What’s so funny about that?”

“Look, no offense,” he said, shrugging. “But everyone thinks they’re the wild child, you know?”

“Do you need to see my credentials?”

“Do you have some references I can call?”

“Sooner or later,” she said, “I’m going to finish this drink.”

“And then?”

“I suppose that’s up to you, Daddy.”

“Earned that title already, have I?”

She shrugged. “Some men just get to be Daddy. Congratulations. It’s a girl.”

He kept his calm, smirking as he spun the remnants of his mostly melted ice in his glass. She really was something else entirely, and he wondered if he wasn’t at least a little out of his element. Normally, he felt like he was the one running the show. Whether he was or wasn’t didn’t matter so much as did the fact that she probably thought she was running it.

“I suppose you’re staying somewhere local?”

“I am.” She smirked. “And you?”

“I have a place in town.”

“I’d rather mine, if that’s okay with you.”

He nodded. This was unexpected, nor was it how he liked these things to go. There was a small part of him that considered just bailing altogether. Maybe he’d make an excuse. Maybe he’d just pay the tab and walk out without saying another word. There were an awful lot of people in the world - he’d never see her again.

Alas, he was curious. It was a terrible thing, really.

“Ready when you are,” he said, swallowing the watered-down final drops of bourbon in his glass.

“I’m Emma,” she said. It probably wasn’t her name.

“I’m Louis.” That definitely wasn’t his name. “Do you like your manhattan?”

“It’s strong.” She shrugged. “I like it.”

“A good stiff drink can do wonders for you. A cosmo...it’s like drinking a glass of juice.”

“You’re so wise, Daddy,” she cooed.

He resisted the urge to glance around them to see if anyone had heard that. It probably didn’t matter. This younger guy sitting on the other side of her now? If he had heard that, he’d be jealous anyways. He’d probably cream his expensive looking pants.

She set her glass down on the bar, it’s hollow ‘clink’ signalling that she was ready to go. He reached into his jacket pocket, pulling out some cash and dropping it on the bar. He nodded to her, and she grinned. Standing, she linked her arm with his, and they walked out together.

“I’m down this way,” she said, pointing down 5th. “I think.”

“What hotel?”

“Greenleaf?”

“That’s this way, actually,” he said, pointing down the opposite direction.

She giggled, shaking her head. “Thank you, Daddy.”

They didn’t say much on the walk there. He’d glance at her face from time to time, but he just saw a satisfied and smug smile. Otherwise unreadable. She was a little enigmatic. It seemed troubling, but he wasn’t sure why. He didn’t believe she had ill intent - nor did he - but he wondered what her angle was. He disliked feeling out of the loop.

The Greenleaf was ahead of them. It wasn’t chock full of amenities like other city hotels, but it more than made up for it with its history. There was something simple and classic about it that he admired every time he came here.

“Sixth floor,” she said as they walked through the lobby. “Not the best view. But I’m in love with how soft their sheets are.”

He once had a similar observation about their sheets, but it didn’t seem appropriate to say so.

The light was already on in her hotel room, and it barely looked like she had spent anytime here. The room appeared to be in an immaculate untouched condition, save a small stack of suitcases and bags.

“Do you usually pack so heavily for one night?”

“One night here. But I’ve got other places to be after this.”

“You’re a busy little girl.”

“You have no idea. May I get you a drink?”

“What are my choices?”

She giggled again, as if triggered by a private joke. She opened the mini fridge, pulling out a bottle of wine. Nothing seemed especially funny about the wine, which only made him more curious.

“Pinot grigio,” she said. “Truth be told, I’m a riesling girl myself, but this is close enough.”

“Break it open,” he said with a smile.

She took two drinking glasses from a counter - unwrapping them from the plastic that signified that they were sanitized and began pouring them each a glass. While she did this, he stepped to the window, pushing aside the curtains so he could check out the view for himself. It wasn’t terrible. He’d seen worse.

He felt her presence behind him, and two hands emerged from between his body and his arms. He took the glass from one of the hands as they proceeded to wrap around him. She pulled herself close.

“I’m happy you’re here, Daddy.”

“I’m happy I’m here too.”

He sipped the wine - it wasn’t really his type of wine, but it’d do. He set it down on a small table before slowly turning in her arms so that he faced her. He wrapped his arms around her, adding a little extra strength to his embrace for that full Daddy Experience.

She moaned softly.

He felt a little off. He was enjoying this, but she felt unknowable and mysterious. That was his role.

If nothing else, she was nice to look at. Nice to hold. For as much as he had a type, she probably fit it well. Shorter. A few extra curves. That long thick hair. She’d look nice bouncing on top of him, for sure.

His hands slowly slid down her back. More soft, very soft, moans leaked from her lips. His head lowered, and her hungry lips eagerly met his. Her soft plump lips were like candy. Traces of her manhattan lingered, and she tasted naughty. As his hands reached her hips, she stepped back. Much to his disappointment.

“Get back here.”

She blushed a little. He liked that. It was actually a little bit of a relief. Maybe some of the advantage was coming back to him now. She hesitantly stepped forward again, throwing her arms around his waist. His hands picked up where they left off, finding her hips and slowly sliding back to cup her ass. He had been looking forward to this - her round and voluptuous bottom had teased him every time he caught a glimpse of it.

Yet now, with his hands on her ass, it both was and wasn’t what he was expecting. He couldn’t even make sense of what his hands were grabbing. It was...thick? Padded? Crinkling? She buried her face in his chest, giggling.

He wished he didn’t have to ask, though there didn’t seem to be much choice. “What am I feeling here?”

“May I show you, Daddy?”

“Please.”

She stepped back again, backing up until she reached the bed. She flopped onto it, landing on her back, kicking her feet up in the air.

“Help me with my pants, Daddy?”

With pleasure.

He gripped either side of her pants at her waist, the tops of fingers rubbing against her panties. Maybe they were her panties? They felt slick. Plastic. Again, his mind couldn’t grasp what it could be. He gave her pants a good pull, sliding them down to her knees. Another pull brought them down to her ankles. As he stepped back to get a better look at what he was working with, she kicked off her pants the rest of the way.

This was an interesting development.

“That’s a…”

“Diaper. Yes, Daddy, it is.”

The thick plastic garment wrapped around her curves almost perfectly. In the back of his mind, he knew there were people who did this, though he had never really given it much consideration.

She lifted her legs again, kicking them in the air playfully. As her legs distanced themselves from each other, he had a clear look at her bulky padding. Notably, the padding between her legs seemed discolored. Darker. Damp.

“And you’ve gone and had an accident too, I see?”

“Yes,” she moaned. “While we walked here. I looked into your eyes as I did it.”

Regardless of how alien this was to him, he liked that.

“Do you need a change?” he asked. He looked back to her suitcases and bags, wondering if he had stumbled into the need for her heavy packing.

“We haven’t even had any fun with this one yet, Daddy.”

He approached the bed. Her arms were outstretched and her legs were kicked into the air. She looked inviting. Welcoming. She wanted him on top of her, and that was where he also wanted to be. He carefully lowered himself on her.

Her lips were on his again, offering a flurry of short wet kisses. She kisses his cheek. His nose. His lips again. His neck.

His hand wandered down to her diaper. How could he not be curious? It made its way between her legs, feeling the difference between the dry areas and the area that had been saturated. It was warm and squished between his fingers. She moaned softly in his ear between kisses.

“Were you a naughty little girl?”

“Yes, Daddy. So very naughty.”

“There’s things we do to naughty little girls who can’t keep their pants dry.”

She moaned again. “Please, Daddy. Can you show me? I need to learn.”

He rolled off of her, sitting up on the edge of the bed. Regardless of what she was wearing, some things still felt the same as they always did. Another bad girl in need of Daddy’s hand. He pulled her up into a sitting position too, before hoisting her over his lap, face down. Her diapered rear stuck up in the air, and while there was some extra padding - it was still quite the spankable bottom.

His flat hand struck the diaper without warning. He doubted she could feel it too much, but the surprise had at least elicited a yelp. Truth be told, he liked the way his hand sounded, rebounding off the synthetic material and padding. Again and again, his hand connected with her bottom with a loud slap. She moaned through it, intermittently adding an extra noise or two.

“Are you just a little girl?”

“Yes Daddy.”

“Tell me what you’ve done.”

“I...I...wet my diaper.”

“But it wasn’t an accident, was it?”

“N-no. I wanted to do it. I like pissing myself?”

“Naughty. Disgusting.”

“Do...do you really think so?”

“Oh yes. And what a sneaky trick. You approach a man at a bar, hiding the fact that you’re an overgrown toddler wetting her pants?”

“I...I’m sorry. I should’ve been more upfront. I should’ve told you - right there at the bar.”

“Maybe you can practice right now,” he said, his hand continuing to slap her thick bottom. “Pretend you’re approaching me at the bar. What would you say?”

“I...well… Hello, sir. I’m...a little girl. Because I wear diapers.”

“No, no. That won’t do. Yes, you want to be upfront about the diapers and how much of a pathetic toddler you are. But you also want to make it clear that you’re there to serve them too. They’ll get more out of this than just having to be a babysitter, yes?”

“Yes… You’re right, Daddy.”

“Try again.”

“Hello, sir. I was looking for someone I could call Daddy tonight? Someone who, uhm, could keep me in my place?”

“This is better,” he said, recalling how their conversation started not that much earlier. “Suppose he shows interest?”

“Thank you, Daddy. But, uhm, you should know...that I’m a very naughty little girl.”

“Are you? How so? Tell me.”

“Well, Daddy, I… See, I wear diapers. And sometimes I have accidents in them.”

“Why do you wear diapers? This is important.”

“Daddy,” she said, starting over, “I wear diapers too. Because I’m a pathetic little girl who likes to piss herself.”

He finally stopped slapping her diaper, and instead eased her back on to the bed. He stood and walked back to the table where he had left his glass of wine. She couldn’t see his face, but he was smiling. He had his power again. It took a little extra work, and there were a few extra hurdles. But, dammit, he persisted and it had been worth it. He tilted the glass into his mouth, quickly downing a good amount of wine. He set the glass down again, wiped his mouth clean, and turned around - finding that Emma had rolled over onto her stomach. Her legs dangled off the end of the bed, and her diapered bottom was presented to him.

“Daddy, please. Take me.”

He didn’t need to be asked twice. He unfastened his belt and unzipped his pants, pulling his hard cock out. He had been ready for this since he felt her soggy diaper with his hand.

He carefully pulled the back of her diaper down just below her ass cheeks. He let his hand glide down her crack, feeling the smooth baby-soft skin on either side, before he teased her dripping wet pussy. She moaned, partially muffled by the pillow planted under her face. No further welcome was needed - he guided his shaft into her, her tight wetness engulfing him.

It didn’t take long. It was hardly a humiliating length of time - but it never would’ve been enough. The way she moved against him, the way he seemed to fit perfectly within her, the soggy diaper bouncing off of his body as he entered her - it was better than he ever could have imagined.

“Please…” she said between deep breaths and moans. “Please...when you...come. I want it in my diaper. Come in my diaper. Please.”

“You’ll need to beg better than that.”

“Please. Please, Daddy. I need it so bad. I need you to fill my diaper with your come. I want to sit in it. I want to wear it. I want to piss on it.”

“Why do you want that so badly?” It was getting harder to contain himself. He hoped she could answer this query quickly.

“It’s because I’m a disgusting little pathetic baby. Daddy, I’m just this awful little toddler. Please. Make me feel disgusting and dirty. Fill my diaper up and…”

He cut her off with a primal grunt of his own. Clutching his cock in his hand, he pulled it from her and jammed it into her diaper, just barely making it before he exploded - shooting his sticky load into it as she had requested.

She twisted and bent before him. She wanted more. He dropped to his knees, plunging his face into her backside, taking in the musky mix of piss, come, sweat and, perhaps, baby powder as his mouth suckled on her clit until she also came, saturating his face.

Emma pulled her diaper back up herself, slowly easing back into its sticky new status quo. He landed on the bed beside her, panting and out of breath.

“Are you okay, old man?” Her wit seemed to have returned.

“Don’t you need a diaper change?”

“I think I’m going to stay in this one for a while.”

“Have it your way. I offered.”

It was a new game when it came down to navigating how the night ended. They had their fun, and they each got what they wanted. She’d be gone the next day, and there wasn’t much need for formalities. Still, nobody wanted to look heartless or rude.

“I enjoyed tonight,” he said later as he straightened out his shirt in the mirror.

“I’ll be enjoying it a little longer,” she said.

“Don’t get a rash.”

“I have cream just for that.”

“I bet you do.”

She’d walk him to the door, kissing him one last time. He had to be stoic, regardless of how badly he wanted more. The door closed.

He’d take a week off from the bar scene. It almost felt disrespectful to his own memories to attempt to make new ones so soon. He’d spend the nights, instead, navigating message boards and communities he never would have before. Maybe he hoped to find some sign of her - some other mark she had left in the world that he could follow. Or, maybe something new had awoken in him.

A week later, at a different bar, he was striking out. No bites. So nights were like this. Most nights were like this.

Behind him, at one of the small tables, he caught a small voice. “Hello, sir. I was...looking for someone I could call ‘Daddy’ tonight.”

He laughed. He had to.

“Oh?” a man’s husky voice responded. “I could probably help you with that.”

“Thank you, Daddy. But...you should know. I’m a very naughty little girl.”

“Is that so?” The man offered a hearty laugh. “I’m sure it’s nothing I couldn’t handle.”

“But Daddy, you see, I wear…” her voice disappeared, dropping to a whisper inaudible from where he sat.

“Can I get you a drink, miss?” the man said.

Louis, or whatever name he had tonight, stood up, having finished his drink. He turned, seeing Emma sitting closely to this new man at the table. Older. Handsome. She certainly had a type. He didn’t say anything, nor did she - though she did offer him a knowing look. A naughty glance, really.

He left the bar, laughing as he walked down the street. He wasn’t even mad. It was a tough game, and when you met someone who played it better than you did, what else could you do but respect it?