Lady's Third Day - Evening

Check out Lady's 1st and 2nd Days for a more complete story.

Day Three - Evening

Once I wiped off the cum from Mr. Prick, I opened the gift he left for me. It was a small BVLGARI clutch, deep green with a delicate, silver chain. I caressed the smooth leather and shiny clasp.

As soon as I returned to my room, I perched the bag in my display closet beside my diamond necklace... the beginning of my collection. It wouldn't take long. A few months and I would have enough compensation to start the next steps. A few months of hot sex? I think I could handle that.

I showered and dried my hair before combing it back into a slick bun. Sir had requested my hair up.

Our meeting time of 7pm creeped closer.

Mascara and lipstick on my face, lotion on my legs, perfume on my neck, polish on my nails.

I slipped on the dress Sir sent to me. It was a bold red, with a high slit and low back. The neckline dipped almost to my bellybutton. I felt sexy and confident and half-naked.

News about my date with Sir had spread across the mansion. As I walked to the front door, girls pointed and whispered. A few followed me nonchalantly, and soon, there was a full crowd behind me.

I stood right outside the front door, waiting, when Rose wandered by. The whispering stopped immediately as the girls intently watched the scene.

I watched her approach me. She moved so gracefully. Her hips swayed back and forth with each step. Her long black hair was loose around her shoulders today.

Without hesitation, she stood before me and kissed me hard.

The whispers began again, loud and obvious.

But before I could respond, Rose winked and left.

Confused and self-conscious, I was glad when the limo finally arrived.

The driver ran around the car and opened the door.

My heart skipped a beat when I saw him. His piercing eyes and soft, curly hair. Sir motioned me into the car.

I slid in beside him, happy to be away from the whispers and stares.

"Lady." He greeted me and kissed my cheek. "Thank you for joining me tonight."

"Of course." I responded. My stomach was in knots. He was so handsome. I thought back to the first time I had seen him.

*I was 19 when we met. I had only been free from my past for a few months, and the world still seemed scary and big. He was kind and gentle. But commanding and strong.

It had been the best week of my life. A whirlwind of romance and excitement. He had taken me to expensive restaurants and trendy nightclubs. I had stayed with him each night in his luxury hotel suite and let him explore my body.*

Sir put his hand on my thigh. Immediately the skin he touched turned red hot. His touch felt electric.

"I think about that week a lot." Sir said suddenly, as if reading my mind.

"Me too." I admitted.

"What changed your mind?" He asked.

I looked at his eyes. They were sharp and dark, surrounded by thick eyelashes. I could have melted into them. Slipped away from reality and climbed into him. And I wanted to.

"Time." I answered. "When we met... I was in a different place."

"I'm glad you decided to join." He responded. "I wish you had decided earlier."

I smiled and looked down at my lap.

Sir placed his hand on my cheek delicately and turned my face towards his. Without any hesitation, he kissed me hard and slow.

My body turned on and responded naturally. In that moment, there was only me and him.

When we broke away, I sat dazed for a moment. Since the second he left me after that beautiful week together... I had been waiting for this moment.

After a while, the limo stopped, and a few moments later, the driver opened the door.

Sir stepped out first and held out his arm to assist me. The air was warm and windy, and I could hear waves crashing against a dock and the dull chatter of a small crowd..

Before us stood a magnificent boat. It was a sparkling white yacht with several decks and a shimmering pool in the front. The long dock leading to the boat was filled with glamorous gowns and dark suits: attendees waiting to board.

"Where are we?" I whispered as Sir took my arm and led me towards the boarding ramp. He nodded and smiled at several men as we passed, ignoring the queue.

"It's a benefit. For children or trees or something." Sir whispered back.

He saw someone in line that required a proper greeting. They shook hands and offered greetings and small talk to each other. Sir complimented the lady he was with.

"Delilah." Sir kissed her hand. "It's a pleasure to see you tonight."

She was familiar. Another accompaniment that I had seen around the mansion. She looked at Sir and then at me with confusion. Most likely wondering about Rose.

Once small talk exhausted, Sir wished them both a wonderful evening and took my hand. We continued to the boat.

**********

As the boat left the dock, Sir and I stood on the lower deck watching the waves crash around us.

We were mostly alone, with just a few others enjoying the night air. The majority of the attendees were inside waiting for dinner.

The boat followed the coast, and I watched the lights flicker along the shore.

Sir stood behind me, pressing his body against mine. He wrapped his arms around me and kissed my neck.

In that moment, with the wind gently attacking my face and the moon staring down at us and Sir's strong arms holding me tight, I felt safe.

"I missed this." I said.

A handsome gentleman approached us hesitantly. He nodded at Sir, and Sir responded with a gentle smile.

"It's a pleasure." Sir said, shaking his hand.

"The pleasure is mine." The stranger replied, kissing my hand in greeting. "Thank you for meeting with me." He stared openly at me, gawking at my revealing dress. I watched his eyes travel up and down my body, focusing on my breasts.

Sir turned to me. "Lady. Would you excuse us for just a moment."

I agreed and stepped away, feeling the stranger's eyes on me as I left.

I settled in a comfortable seat a short distance away and watched the two men talk. I couldn't hear anything, but I could see the excitement in the stranger's mannerisms.

Sir looked composed and confident. He stood tall but not stiff, and his focus was fully on his conversation. He handed the stranger a business card, and they shook hands again.

The encounter didn't last long, and soon Sir returned to escort me to dinner.

I didn't ask, but he could tell I was curious. We began at the bar, and as I sipped my champagne, Sir answered. "A potential client."

"Oh." I said.

He handed me a business card. It was black and glossy. There was no business name, just a phone number in raised, white font.

"In this business, there's a fine line between privacy for the current clients and solicitation for future clients." He said.

For the next few hours, it was like I was back in that week. We drank and ate and danced. Sir held me close during slow songs; my head rested on his chest.

He brought me outside as the yacht made it's way back to dock, and we watched the lights of the city glow brighter as the shore got closer.

Soon, the limo was dropping us off at a small apartment complex in the outskirts of town.

"Are you ready?" Sir asked as we entered the dimly-lit apartment.

I smiled and nodded. As we moved into the bedroom, my eyes adjusted to the apartment lighting, and I could now see a large bed. Four bedposts with fabric ties cornered the mattress.

"Undress and Lay down." He commanded. His voice had changed already. He was in control now.

I took off my dress and underwear as he watched closely. I laid on the bed and held my arms and legs out like a starfish. He immediately began tying them to each bedpost.

As he knotted, I laid flat and open. I felt vulnerable... and excited.

After he tied the knots, he began rummaging through a large dresser.

I laid still, my pussy trembling already as I anticipated what was coming.

*I remembered our week together. During the days, I was his lady. A beautiful muse to protect and care for. He would buy me whatever I asked for and take me to any restaurant or show I wanted.

But during the nights, he was in control. He took pleasure in seeing how far he could push my body.*

And I remembered the rule: as soon as I orgasmed... it was over.

He turned back to me and fitted a tight harness around my hips, with a vibrator wedged between the straps, pressing hard against my clit.

"We'll start slow." Sir said as he turned it on.

The vibrations were soft and rhythmic. My body immediately responded, trying to squirm away from the instant, overwhelming pleasure. But the ties on my ankles were too tight.

I laid helpless and stretched out, focusing on each breath in and out. I wasn't going to last. The excitement for our date and the anticipation as we neared the end of the evening had built up an intense arousal. In only seconds, I was near a finish.

Sir left the room, and I could hear the clinking of glass as he poured himself a drink.

I couldn't help it... waves of pleasure jolted through me as soon as he stepped out of the room. I bit my tongue, forcing myself quiet as I came violently. But it wasn't satisfying... i longed for something slick and hard to enter me.

The insufficient orgasm was cut short abruptly as he reentered the room. He looked at me and my struggling breaths. "Did you..." he began to ask.

"—no." I lied immediately.

He smiled at me and sipped his drink. I couldn't tell if he knew I was lying.

For ten minutes, I laid there with the vibrations pounding on my clit. Each minute that passed, Sir sped up the vibrations. By the time he casually finished his drink, my pussy was raw and desperate for penetration.

Sir took off his shirt first, and then his pants. His tight boxers clung to his hard cock. I could see it bulging - begging to be released.

He removed my harness and the vibrator, and my inner walls clenched from the sudden lack of stimulation.

He moved around the bed, staring intently at my body, rubbing his bulge over his boxers.

Then I was blindfolded. I felt him tighten the straps on my arms and legs, pulling my body even more open.

I could hear him moving things. My body felt confused and vulnerable as I waited.

Then it got quiet. In the darkness of the blindfold, my ears struggled to make out any sounds. But nothing; it was silent.

Sir left me like this for hours. Or maybe it was only a few minutes. Without my vision, I couldn't tell. I squirmed and wiggled, trying to signal to him that I wanted more. Needed more. Immediately.

And after a while, I became quiet and listened for any sign that Sir was even still in the room.

Finally, I heard footsteps towards me. I felt his breath as he leaned close to my head.

"I know you lied." He whispered.

I heard his voice move as he walked around the room again.

"We'll start again." He said.

I felt him crawl onto the bed below my legs, and then I felt his tongue on me. He took long licks between my pussy lips and flicked his tongue on my clit.

He moved closer and his entire mouth pressed against my opening. His tongue slid in and out of my hole, encouraging my juices to begin to flow again. Mixing with the dried juices from our first session.

I gasped and moaned quietly, peering into the blackness of the mask. I could picture him in my mind... kneeling on the bed... slurping between my legs.

Once Sir determined I was wet enough, he backed away, and I felt a strap across my stomach and thighs. He secured my body tightly, so I couldn't even squirm.

Then I felt the machine. With my legs forced open and my body tied down, I felt the slow and steady repetitive penetration. The toy was thicker than most cocks and ripped me open again and again.

It was moving incredibly slow... in and out of me. My pussy clung to it each time it entered me, and I moaned each time it exited.

Sir drizzled a lubricating oil on it, creating a slick movement that began to get faster.

It moved in and out, and I felt myself cresting. But it was still too slow. My pussy ached for aggression.

I tried to squirm, but I was held tight by the restraints.

I felt Sir sit on the bed beside me, probably watching my tits jiggle up and down with the machine's movements.

"When you show me you can handle this speed, we'll go faster." He said.

I calmed my breaths and tried to relax my hips. Almost immediately, Sir turned up the speed.

The sudden change caused me to moan involuntarily. I begged for faster still, but Sir responded with silence.

The new speed felt amazing, and I moaned and squirmed at the pleasure. After enjoying a minute of the faster penetration, I began to calm myself. I slowed my breaths and held my hips still.

Noticing my determination, Sir sped up the machine again. It inserted itself over and over again. I could barely breathe, and even with the blindfold, I felt my vision blur from the excitement.

Then I felt Sir straddle my body. He was naked now, and I felt his cock brush against my breasts. He poured the lubricating oil on my tits, and I felt him slide his cock over my slippery nipples. They perked up in arousal, excited to be included.

The constant toy penetrated my pussy over and over again, and I felt Sir begin to slide his cock in between my tits. He humped my breasts and then moved up more, so his cock rested on my lips.

I could feel his body hovering over me, and I began to kiss his cock. I let my tongue move all around the tip, making out with the swollen head.

He moaned as I worked. We stayed like this for minutes. The only change was the progressively faster speed of the toy in and out of my vagina. I was taking the unbearably pleasant assault on my pussy out on his cock, licking and slurping with comparable aggression.

He adjusted his position, so he could shove his entire cock in my mouth. Saliva and pre-cum dripped down my chin and neck as he began pumping.

I laid still with my mouth open, unable to concentrate on anything other than the cock in my mouth and the dildo in my pussy, both thrusting roughly in and out.

His head swelled inside my mouth as I felt him near his finish. As he approached the orgasm, he fucked my face even faster. His cock stabbed the back of my throat and I gagged.

Then he moaned loudly. As he groaned, hot semen squirted into my throat. He continued moaning as streams of saltiness shot onto my tongue, mixing with saliva and oozing out the corners of my mouth.

The excitement of his cum brought me to finish and I felt myself tense and ride the waves as the toy continued to pump in and out of me. My inner walls restricted and grasped the toy tightly.

We climaxed together, gasping and groaning. His fluids dripping into my mouth, my fluids coating the dildo.

He pulled out of my mouth, shaking drops of cum and saliva on my lips and cheeks.

I felt him move off the bed, but the toy continued pumping. He must have adjusted the speed because it suddenly slowed down to the original slow and torturous thrusts.

As I calmed from my orgasm, I found my voice again. "The rule." I spit out. "I came. Is it over?" Part of me wished for a "yes" and part of me wished for a "no".

The only answer was the constant, slow pumps of the toy.

It didn't take long before I was excited again. With the nonstop penetration, I couldn't fully come down from my climax. I sat hovering in excitement, wanting more.

I felt the restraints on my stomach and thighs loosen. With new freedom, I squirmed with the machine, pushing back against the dildo.

A warm, soft cloth rubbed across my face, wiping the cum and spit away. His touch was gentle and the toy was moving slowly. A new sense of intimacy washed over us, a softer and more gentle sensation.

The toy stopped suddenly, but I continued circling my hips, aching for the movement. I felt him kneel on the bed and pull away my blindfold.

My eyes took a second to adjust to the new light. I could see his face inches from mine. His sharp eyes under dark, thick eyebrows looking directly into my eyes.

He was on top of my body; my limbs were still strapped to each corner of the bed. I felt his cock where the toy just was, hovering over my opening.

He pushed forward gently, letting his hips move to mine. The head of his cock slowly pushed into my swollen pussy lips.

He pulled out and quickly untied the restraints. With my arms and legs now free, I melted into his embrace.

He entered me again and again, watching my breasts bounce in rhythm.

His pumps quickened, and he began grunting as he moved. Aggressively, he pushed himself into me hard, pressing his body tightly against mine as he convulsed.

I felt a new stream of cum, much less than his first one, shoot deep inside me. I moaned quietly in pleasure as he humped the resulting waves away, holding him tighter with each thrust.

He pulled out satisfyingly slow and laid beside me, wrapping his arms tightly around my chest.

In the silence, I could hear his heartbeat pounding and breath shaking.