A Night on the Town

"Carly, I want you to go introduce yourself to that man at the bar," Sir gestured toward a well-dressed, dark haired man sipping his drink at the bar. "I want you to proposition him and see what happens."

I stared across the room, and the man caught my eye, offered an appraising look, and turned back to continue talking to his friend. Sir and I were seated in a booth at his favorite upscale bar in the middle of downtown. The Thursday night crowd was full of faces I recognized, some Sir's coworkers, some his friends.

Sir raised an eyebrow as he looked at me and I quickly recovered. "Yes, Sir," I replied. I took one last sip of my wine and stood. Sir knew I loved a challenge and a chance to let my exhibitionist side out. But, he'd never had me try something in such an unstructured environment and I was a little nervous.

Always up for a challenge, though, I stood up straight, squared my shoulders and strutted over to the bar to take the seat next to the dark haired man. "Well, hello beautiful," he said before I could say anything.

I turned toward him and flashed a bright smile. Up close, he was quite attractive and also slightly familiar. I couldn't place him and figured he must have been at some function I'd attended with Sir. "Hello, yourself," I purred.

He caught the bartender's eye to order me a drink. "Were you drinking wine with Mark? Would you like another glass?" he asked me.

"Ah, yes, I was. Pinot grigio, please." He ordered it and turned back to me, slightly closer than he had been when I sat down.

"I'm Rob, by the way. I know Mark from some parties around town," he smiled at me slyly.

I see, I thought to myself. This wasn't as unstructured as I thought. Sir knew exactly what Rob's response was likely to be. This wasn't so much a test of obedience as it was a bit of fun for me. I relaxed and turned on the charm.

"I'm Carly. We're here rather often and I'd hate to think I'd never noticed you before. It doesn't seem possible," I smiled and put my hand on his arm. Rob took that as an invitation and tucked a strand of hair behind my ear before draping his arm over the back of my chair.

"Oh, I'm not here very often. I'm usually rather occupied and don't get out much during the week."

"That's a shame. All work and no play?" I asked, turning into him more so that my legs were straddling his thigh as he stood next to me.

"I wouldn't say that," he winked at me. "I certainly know how to unwind."

"Shall we see if that's true?" I asked him. I looked up at him coyly, quite close to his face. He turned to face me fully, and my legs spread, hiking my short dress up my thighs, dangerously close to exposing my pussy.

Rob glanced down and smiled as he slowly looked up to my breasts and then met my eyes. He licked his lips as his smile intensified. "Absolutely. Lead the way."

I slid off the bar chair slowly, pressing myself against him. I left my glass on the bar and grabbed his hand and pulled him toward the back of the room. I'd been here often enough to know that the bathrooms were well set apart and large enough to have powder rooms. Not that it mattered because women were rarely in attendance at this bar; it was more of an evening club for the wealthy downtown than a bar for the masses.

I pulled him into the women's restroom. As the door closed he pushed me up against the wall and kissed me. His hands hiked my skirt up and he grabbed my ass. I could feel his cock getting hard and it turned me on even more than the fact that someone could walk in at any moment.

I pulled back and sank down to my knees, my eyes on his the whole time. I unbuckled his belt, unzipped his pants, and pulled out his thick cock. "Mmm," I said blowing lightly over him teasingly. "I bet you unwind all the girls with this."

Before he could answer, I put my mouth on him and licked the length of his shaft. I swallowed him, inch by inch, until I had all 9 inches of his thick cock in my mouth. Slowly, I released him and started over again, deep throating his cock as he got harder and harder. He grabbed the back of my head and held me against him, balls on my chin, until I choked on his dick.

"You are good," he said, pulling me back up to standing. "That mouth could certainly relax me every day."

I moved over to the couch in the powder room and he followed me. He pushed me over the arm of the couch and pulled my skirt up to my waist. I arched my back and pushed my ass up. He ran his hands over my ass and slid two fingers down to my pussy. He ran his fingers back and forth for a minute, teasing me. When I gasped, he stopped.

"You have such a wet pussy, Carly. Are you always this wet, or is this just for me?"

"It's your cock, Rob. I want your thick cock inside my wet pussy," I panted.

"Oh really?" he said teasingly.

I turned and looked at him over my shoulder. "Yes, I want you to fuck me with that gorgeous cock."

His eyes darkened as he smiled at me, taking in my very compromising position. He ran a finger down my spine, making me shiver in anticipation. Then he grabbed his cock and rubbed it up and down against my clit, just as his fingers had teased me. I moaned and he stopped.

"You are a little cock slut, aren't you?" he said.

"You have no idea," I replied. I stood up and pulled my dress off leaving me in black heels and nothing else. I sat on the edge of the couch, legs spread, and pulled him to me. I teased his cock, kissing and licking the length of him, before slowly taking him in my mouth again. This time, he didn't wait for me to swallow him; he held the back of my head and fucked my face until I couldn't breathe. When I choked on his cock for the second time, he stopped and let me catch my breath, but only for a second before he fucked my mouth harder and deeper, stopping to hold his full 9 inches deep in my throat.

"Kneel on the couch," Rob said and I complied, knees on the edge, hands on the back. I felt the head of his cock teasing my clit just as hid fingers had and I arched my back again, grinding my ass back against him. He took the invitation and pushed into my pussy deep and fast. He reached around and grabbed my tits while he fucked me hard. His hands slid down to my hips to hold me in place as his cock slammed into me over and over, driving me completely wild.

Rob pulled completely out and I whimpered at the sudden stop. He pulled me off the couch and pushed me down to my knees again. I kept my eyes on his as he stroked his cock and came all over my face. Still watching him, I wiped the cum off my cheeks and chin and licked my fingers.

He tucked his shirt back in and helped me up. "You were right, you definitely know how to unwind," I said as I retrieved my dress from the end of the couch.

He chuckled. "See you around, Carly," he said from the door and he walked out leaving me to put myself back together.

A few minutes later, I left the restroom and returned to Sir's booth to find a fresh glass of wine waiting for me. "Rob brought that over for you. He said you earned another drink on him. Good girl," Sir said, pulling me into the booth next to him. I smiled and relaxed into my place next to Sir.