Friday Night at Pine Hill (Patreon)

“I don’t want to do that,” she said timidly, biting her lip.

“But you would, yes? If I told you to?”

Her breathing became heavier and her cheeks glowed pink. She considered it for a moment - likely already knowing the answer, but just not wanting to have to say it aloud. “Yes sir.”

“But you’d rather do anything else?”

“Yes sir. Yes, Daddy. Anything.”

He didn’t even think he had asked for something that challenging, but clearly it had struck a nerve with her. He wanted to delve a little deeper and explore it, but that could wait . He could accept this, for now. Maybe it was a discussion for another day.

“Okay,” he said, nodding. “Then here’s your alternative. And you’ll have to choose: Either this, or the first option.”

She listened intently.

--

Pine Hill hadn’t been especially busy the last few weeks. It wasn’t tourist season - and while the tourists never came here, they at least pushed all the other locals who didn’t want to be around the tourists here. The Friday night crowd, the most reliably large group, was almost entirely responsible for keeping the lights on, and that was hardly a ‘crowd’ at all.

Drake wouldn’t have it any other way. He’d keep his fingers crossed for the long term well-being of his favorite watering hole, Pine Hill, but he relished this - the quiet season. It was the perfect place to unwind after a long week. He could chat with the other local regulars if he wanted, or he could just focus on a nice tall beer or three.

For this particular night, he did tell James and Doug that he’d be here. They said they’d be here. Doug’s SUV was already here, so he already knew he’d have a little catching up to do. That was fine by him.

“E-excuse me?” A woman’s voice came from between two cars in the parking lot - maybe the only two cars in the entire dark lot that were next to each other.

He spun around, spotting her silhouette. His first instinct was that she was in trouble. “Hi,” he offered.

“Can I bother you for a moment?”

“You’re not bothering me.”

“I...I have a favor to ask.”

He couldn’t gauge her emotions. She sounded troubled, or maybe just nervous - but there wasn’t necessarily a sense of urgency in her voice. “What can I do for you?”

“It’s more like...what I can do for you.”

She took a step or two out of the darkness. He wasn’t sure what to expect, but somehow it hadn’t been someone looking as normal as she did. She was cute. Simple. She didn’t seem to look distressed. Maybe they never do?

“I’m not sure I follow.”

“This is hard for me to say, sir, so I’m just going to be blunt with you.”

Sir? “Okay, shoot.”

“This was a dare. And I...promised to do something.”

“Okay…” If this is her being blunt…

“I need to...please a stranger. WIth my mouth. You know?”

He took a deep breath as he tried to process the surreal situation he was finding himself in right now. “You don’t have to do that,” he said.

“I want to. I have to.”

“Is someone making you do things you don’t want to do? I can call someone, you know.”

“No...no, please. I want to do this. If it’s not you, it’ll be someone else. So, are you interested?”

He wanted to weigh his options, but he didn’t know where to even begin. He quickly imagined her approaching James or Doug. They would jump on this opportunity in a heartbeat. Then they’d storm into the bar, boast about their good fortune and talk about it for years after. But he didn’t have to be like that. He could be respectful, help her achieve her goals, and then...he’d just keep it to himself. Surely this was the better path for her, yes?

She is really cute, though. Just look at that mouth.

“Do I need to be worried about some sort of...disease?”

“No sir,” she said while shaking her head.

“You’re not going to videotape me and put me online?”

“I have to send proof. But...I don’t need to show your face.”

“Who is making you do this?”

“Daddy.”

He scratched his head. He really wasn’t sure what to make of that.

“I have friends waiting for me inside.”

“I won’t take long.”

“My car is over there,” he said. “If you’d like to do it there”

“Can you pull it over there?” she asked, pointing to the more empty end of the parking lot. There wasn’t even a street lamp over there.

“I can.”

She followed him to his car, and as he got into the driver’s seat, she got into the backseat. For a few moments, this seemed like the most sensible arrangement. Yet, as he turned the car on and put it into reverse to pull from the parking space, he found himself awash in doubt and regret. Why was he playing into this? What if she wasn’t okay? What if this was somehow a trick or a prank? Could he be arrested for having oral sex with a stranger in a parking lot?

He talked himself out of the doubts, or he at least postponed further worry with the idea that he’d just drive over to the other end of the parking lot and see what happens. Maybe he would still talk her out of it. Maybe he’d still talk himself out of it.

Once parked again, he left the car and re-entered through the rear door, sitting beside her in the dark car. It was a surprisingly roomy backseat, he noted. It occurred to him that he had never sat back here before.

“So someone dared you to do this? And you just said ‘Okay’?”

She nodded. “I want to do these things. If I didn’t, I wouldn’t be here.”

“What’s your name?”

“I’d rather not say.”

“Are you local?”

“I’d rather not say.”

“Is there anything you are willing to say?”

“I’m sorry...this is already so hard for me. I don’t think I should say much else.”

“Did you approach anyone else before me?”

“No.”

“Then why me?”

“You looked nice.”

He had been told this before, but he certainly didn’t feel nice right now. He felt like a scumbag. Ten minutes ago, he wouldn’t have believed that he would have let a strange woman convince him to get into the back of a car with him in the parking lot of his favorite bar.

“May I start, sir?”

“Oh...are you sure?”

“I promise you, I am.”

“Okay. Let’s...do this.”

He started to unbuckle his belt, but she stopped him. “I’ll do it.” She quickly unfastened his belt and his pants, opening the fly to expose his black boxers. With barely any hesitation, she reached into them and grasped his cock, pulling it up through the waistband. The very idea of this interaction had gotten him halfway to being hard, and this foreign hand did the other half.

HIs back was pressed against the door, and she was on her hands and knees on the seats. He could barely see her face, as her dark hair cascaded down her head on all sides. In the dark, it looked as if a headless phantom was somehow bobbing up and down on his manhood.

He moaned, though he did his best not to be too loud. Likely, nobody knew he was over here. Likely, nobody would hear him. Yet his nerves were still on edge. This was unlike anything he had done before.

With every bob of her head, and as her mouth cleared more and more distance on his cock, he watched her body arch forward. Her black shirt rode up her body, and the back of her pants were in view. Perhaps it was her angle, but her pants seemed to be riding in the opposite direction. At first he thought that maybe it was just her awkward position stretching her pants, but as his eyes adjusted in the dark car, he realized that it was more that her pants were just barely fitting over what she was wearing underneath. Whatever it was, it was thick, padded, and white. Is that a...

“...diaper?” he said softly, finishing his thought out loud.

Her mouth slid off of his cock entirely. He couldn’t see her face, but her voice came from somewhere between his legs, underneath her dark hair: “Yes, sir.”

“Is this...part of your dare?”

“It is and it isn’t.”

Speaking in riddles now. That’s cool. “Okay.”

Her mouth was on him again. It was hungry and eager. He kept expecting hesitation and trepidation, but never encountered either. This did not seem like the tenacity of someone who was hesitantly accepting a dare. She wanted and desired this. She lusted for this. He could hear it in the muffled moans and groans coming from her own mouth. He was enjoying this, for sure, but he wondered if she somehow loved this even more.

Her hand fumbled for something, and when she found it she forced it into her hand. It was her phone. Her mouth released him again. “The camera app. Please?”

He wasn’t familiar with this type of phone or platform, but he saw where he could turn the camera on without having to log into the phone. “Photo? Or video?”

“Video, sir. Please. Make sure the flash is on.”

He set the phone to video-mode and turned the flash on, shining a light down his body, highlighting her as she bobbed up and down on him. She brushed her hair aside so that she could look up at the camera. A few more thrusts of her face on his cock, then she released again.

“Daddy, do you see? I’m a good girl. I’m doing as you asked. As I promised I would. And he knows I wear a diaper. I’ll say this now for you, and for him: I am wet in my diaper right now. Because I get so wet when I am used to bring others pleasure. I’m just a toy, daddy. A pathetic baby toy.”

“No,” Drake tried to interrupt, “you’re not a…”

“No, I am. Please fill my mouth, sir. Make me drink all of you so that I can go back to my Daddy and he can see my pathetic diaper for himself.” She smiled. “You can turn the phone off now.”

He did so, and her mouth was on him again. Truth be told, this was the greatest a woman’s mouth had ever felt on his cock. It never felt bad, but he sometimes worried that he took too long while in this position. But she was working some kind of magic on him right now, and with every single thrust of her mouth and flick of her tongue, he was nearing eruption.

It was hard to explain, but hearing her words as he recorded them, and replaying the last few minutes with her in his mind, he felt himself looking at the situation differently. She wanted to please him. She craved the chance to please him. It was her job to please him. And he wanted nothing more in that moment than to allow her that chance.

“I...I’m going to…”

He couldn’t even finish the sentence, as he felt himself release into her mouth. She had been ready, though maybe not as ready as she wanted to be. She braced herself but still seemed taken back by just how much he had to offer her. She gagged and coughed, but did her part in taking in every single drop.

He couldn’t move. He didn’t even want to.

Meanwhile, she ran her hand across her lips and straightened out her clothes.

“I have to go,” she said.

“May I have your name? Your number?”

“No.”

He had expected that answer. “Thank you.”

“You’re welcome, sir. Thank you.”

She quietly opened the door and left the car, disappearing into the light. He stayed where he was for a few minutes, pants down and dick hanging out.Everytime he tried to make sense of what had just transpired, he found himself hung up on another detail. Who was she? Who was this “Daddy”? Why did she come here, of all places, and how far had she come to get here? The diapers? The video?

Finally, he composed himself and zipped his pants up. He’d go into Pine Hill and have a few drinks, maybe one more than usual. He’d keep tonight’s events to himself. In a few weeks, maybe he’d start doubting that they ever occurred at all.

--

“You did very well tonight,” he said.

“Thank you, sir.”

“Was it hard to do?”

“Yes. The hardest thing I’ve ever done before.”

“And yet, this was preferable to the alternative? My original request?”

“Yes sir.” She paused, then added: “Yes, Daddy.”

“I suspect you wanted this. While it was challenging and humiliating for you, it wasn’t actually outside of your comfort zone.”

“No, sir.”

“You’ll have to do this again, of course.”

“I understand.”

“Maybe you won’t be wearing anything over your diaper next time.”

She swallowed, but nodded. “Yes, sir.”

“You’re a good girl. Come with me.”

She took his hand, blindly following him to wherever he wanted to go next.