I knew I was going to be punished, but like many subs, I still felt a need to resist, at least just a little.
"I'm really sorry, Sir....but I only came because the pleasure of your fingers was too much for me," I said in a quiet voice.
He looked down at me and smiled. I thought for a moment I might have won him over, but then he replied in a calm but stern voice, "You know the rules. And you also know that arguing with me over basic rules will only increase your punishment. Now stand up."
I sighed. I felt petulant, but I stood up. My legs felt a little shaky and I wobbled just a bit. I was glad that it was beginning to get dark outside and that the office light was still out, because otherwise my almost complete nudity would be easily seen from the street below.
"Put your other shoe back on," he commanded.
I must be in a haze, I thought, realizing that the missing shoe was likely not helping my ability to stand. But then, I always have trouble thinking after I cum. It is as if the world gets a little fuzzy around the edges.
I found the red shoe and slid it on, then stood again and waited for instruction.
He stood and pulled his khakis back up. He remained standing. He towered at least a foot over me.
"Did you have the toy with you?" he asked. The air between us seemed to crackle with energy.
"Yes," I replied hesitantly.
"Get it," he said.
I fished into my briefcase bag and located the toy in an interior side pocket. It was a medium-sized lavender phallic-shaped vibrator. Wide at the base to keep it from being fully inserted, it also came with thin elastic leg harnesses to help keep it in place. It was a toy he had instructed me to buy some time ago and to keep with me...and I still carried it, even now.
"Turn around, bend over and insert it into your pussy," he instructed. He sat back down in my office chair. While the room was darkening, and I could not be seen from the street below, my Master would have a perfect view for the show, even in the fading light.
I flushed red. Well, he certainly knew how to pick punishments, I thought. I had never had a man sit and watch me this way, and he knew it would embarrass me. But, I was going to have to pay the piper. I turned, and spread my legs wide and bent forward. I slipped the leg harnesses up my legs. My pussy was still slick from cumming and it was easy to lube the vibrator with my pussy juice. I knew he wanted a show, so I was sure to slide it in slowly, letting him watch the cock disappear into me. Once it was in, I paused.
"Do you wish me to fuck myself with it, Sir?" I asked.
"No," he answered. "But you can give me the other part of it."
He wanted the remote that came with it -- of course. Continuing to present my spread stuffed pussy to him, I slid my hand into the bag again and felt around for the remote. Finding it, I reached backwards to offer it to him.
"It has batteries in it?" he inquired before taking it.
"Yes."
"Interesting," he remarked. "Now turn and bend yourself over the desk and put your hands behind your back."
I bit my lip, excitedly wondering if I might get another spanking. The part of me that had good sense was completely silenced by now. That's the thing about me -- I'm a pleasure slut. My Master knows this. I would probably do just about anything if there was pleasure to be had from it.—I just have to be led into it.
I leaned forward over the desk again, putting my hands behind my back as he had instructed. I heard him stand and move behind me. He somehow managed to use my panties to bind my wrists -- and I could feel how they were still damp from earlier. I waited for the spanking to begin but none came. The silence as I waited was erotic. The room smelled like sex. I could hear how quiet the building had become, and guessed that everyone else had gone home. Wouldn't they be surprised by this show?
Then, suddenly, the vibrator began buzzing. I drew a breath in quickly, both in surprise and because I was trying to bear down against the intense pleasure so I would not come again without permission.
He gripped my butt cheeks, massaging them. He pressed his torso against my back and reached around and rubbed my swollen clit. The pleasure was almost too intense. For a moment I wondered if a person can pass out from pleasure. More pussy juice was starting to run down my thighs. I felt him catch some of it as he gently slid his hand up the inside of my left thigh, teasing my skin. I was breathing hard and uncontrolled moans escaped my lips.
I felt his thumb press against my anus, making little circles around it and teasing the hole. Barely thinking, I pressed my hips backward against the invading digit and I felt him press forward edging slowly into my virgin asshole. I had occasionally lightly fingered my anus during phone sex -- at Master's command -- but I had never actually...
I felt his thumb plunge past my tight sphincter. He paused a moment to let me adjust. Between the buzzing in my pussy and the intense feeling of fullness in my ass, I knew I was going to come soon.
"Master, may I cum?" I gasped.
"Very good, darlin'. You did well to ask. But no...not quite yet..." he said, and I felt his thumb begin to slowly thrust in and out of my ass.
Just then, the buzzing in my pussy stopped as quickly as it had begun. It didn't matter though. I was so far gone my heart kept beating fast and I pushed back against his thumb the best I could, beginning to fuck it so that he didn't even need to move it. I could barely hold back the orgasm.
"Master, please...please Master may I cum?" I begged.
"Yes, you may," he answered simply.
I managed to get out the words, "Thank you, Master," before I came, hard and noisily.
"Uuuuhhhhhhhhhhhhhhhhhhhhhhh.....uuuuhhhhhhhhhhhh...aahhhhhh..."
It felt like I came forever. I felt my sphincter repeatedly squeeze his thumb as I came, and it only made me cum more. Finally, it stopped and I lay spent on the desk, unable to move. Within the last half an hour, I had experienced the two strongest orgasms of my life, and I knew that there would be no way I could ever leave this man.
I must have fallen asleep in that position, because when I came to, my wrists had been unbound but my ass still felt...full.
"Sir?" I said into the increasing darkness. I heard him pull the drapes closed.
"I'm going to turn on the light," he said. "Keep your eyes closed for now."
I did as he said. I heard him flick on the office light.
"You're quite the sight, you lovely slut," he murmured.
I was confused and groggy...I knew I could feel something in my ass, but I also knew he was across the room at the light switch.