#chaoticcompersion

Second date. He’s my usual type—dark features, that Brooklyn Italian twang, late 20s, a nurse. We’d been texting, a little kinky but nothing crazy. He’d told me he was a switch, though he’d never had much of a chance to explore it. Then he mentioned something that caught my attention: a prostate plug.

"Bring it with you," I told him. "Just in case the date goes well."

He picked me up, and as we drove to the restaurant, I glanced over at him, all sharp in his business coat, his hands on the wheel.

"Did you bring it?" I asked, cutting him off from his in depth ramble on Pearl Jam.

A beat of silence. Then—“Yeah.” His voice was lower, almost hesitant, but there was something else underneath it.

I smirked. "Good. Keep it in your coat pocket for now."

He swallowed hard, nodding. Watching a man slip a plug into the pocket of his perfectly put-together coat? That did something to me. He had no idea what he’d just agreed to.

When we got to the restaurant, I saw a table tucked into a quiet corner, next to the window. "We’d like to sit over there," I told the hostess, not giving him a choice. He glanced at me but didn’t question it. He knew.

The next hour was slow, deliberate. I let the tension build, teasing him in small, calculated ways. I dragged my heel up his leg under the table, just enough to make him shift in his seat. When I leaned in to show him something on the menu, my nails barely grazed his upper thigh—higher each time. I felt him tense beneath my touch, his breath catching.

His cock twitched. I saw the way his hands clenched slightly, how his eyes flickered to mine with a mix of restraint and hunger.

I ordered our drinks without asking him. "I know you'll love it," I instructed. Another reminder of who was in control.

Between sips and conversation, I watched him, knowing the question had to be lingering in his mind. Why did I make him bring the plug?

And then, just as the first round of drinks arrived, I leaned back in my seat and locked eyes with him.

"Go to the bathroom." I let the words settle for a second. Then—"Plug yourself."

His lips parted, breath shallow. A rush of color spread across his cheeks as he shifted, his cock hardening beneath the table. He was silent for a moment, processing, wanting, needing.

He exhaled sharply. "Yes, ma’am."

Without hesitation, he stood and walked off. I sipped my drink, watching his back as he disappeared down the hall.

He returned faster than I expected, red-faced, his movements just slightly stiffer. He sat down carefully, and I caught the way his hips rolled slightly, adjusting to the stretch.

"That was quick," I mused. "You must’ve really wanted it."

His throat bobbed. He shifted again, eyes darting to mine. "It... slid in easily. I think I was just—" He hesitated. "Excited."

I smiled. "Oh, I know you were."

For the rest of the meal, I made sure to keep him on edge. My fingers teased along the insides of his thighs, so, so close. But never quite enough. His cock strained against his pants, throbbing, desperate, and every time he looked at me, his pupils were blown wide.

At one point, his voice dropped. "Please."

"Please what?" I asked, feigning innocence.

"Touch my cock," he whispered, swallowing thickly.

I tilted my head. "What was that?"

His jaw tightened. "Please touch my cock. Just for a second."

I arched a brow. "You're forgetting something."

His exhale was sharp, frustrated. But he knew. He recalibrated.

"Please, ma’am. Touch my cock."

A reward, then. My fingers brushed over his length, tracing the shape of him through his pants. He sucked in a breath, hips barely bucking before I pulled away.

"Good boy," I reminded him, satisfied.

He paid the bill.

As we walked to the car, I glanced at him, noting the stiff way he moved.

"How does it feel?" I asked. "Walking around with that plug in you?"

His voice was breathy, a little wrecked. "It… moves when I walk. I can feel it shifting inside me."

We reached the car, and he went to open the driver’s door, but I stopped him.

"No," I said smoothly. "This is happening right now. Get in the backseat."

His breath hitched. His hand fell from the door handle, and for just a second, he hesitated, blinking at me in the night air.

Then, without another word, he obeyed.

** pt two after this**