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I have to admit my newest client was growing on me. Most of my clients came to me wanting only one thing and that was whatever their kink happened to be. Some were really into pain, and only wanted to be beaten, caned, or flogged. Others only wanted to be my puppy for the evening. Still others just wanted to worship my feet. Dee-Dee on the other hand was slowly becoming one of my favorites. He seemed to like it all, and no matter what I did to him, he enjoyed it. That made him more interesting and fun for me to play with. I had taken delight in taking away his kink virginity, and he had paid me handsomely to do it for him!
He had called me on Monday asking for another appointment with me, and we had agreed on a regular time to meet each week. He had insisted that this was fulfilling him in ways he had not ever thought he could be fulfilled. I had known that it would after one glance at his “application.” Having steady reliable clients made me very happy. Being able to use them, flog them, and fuck them in the ass made me even happier.
Tonight was a special occasion. I had asked Dee-Dee to take me out for dinner and drinks tonight instead of our usual dungeon playtime. He had hemmed and hawed and been unwilling to do so, probably fearing that he wouldn’t get his kink fix. Little did he know that this was going to be another of those surprisingly fulfilling nights.
He was ten minutes early, and that was right on time. One of the first things my clients learned was to be “on time.” If you were early you were on time, if you were on time, you were late! I waited for him to knock on my office door, and when he did I opened the door and greeted him.
“Good evening Dean. So good of you to take me out.” I breezed out the door and closed it behind me, leading the way to his car.
“Good evening Ma’am, my pleasure.” He murmured, his eyes downcast.
I waited for him to open the car door for me, and slid into the passenger seat. He got in and started the car. He pulled into traffic driving toward the restaurant we had agreed on. I told him that I had changed my mind and wanted to go to a different restaurant as I applied lipstick. He asked me where I wanted to go, and I told him. This required him to turn the car around to drive back across town. Traffic was heavy, so this took him some time. I complained about the car not being clean enough, and ordered him to have it cleaned properly next time. I complained about his driving, and that it was taking far too long to get to the restaurant. I berated him about his lack of courtesy to the other drivers when he started swearing at them. He kept stealing glances at me from the corner of his eye as my dress rode up my thigh to reveal that I was wearing thigh highs and a garter belt. All of this was carefully orchestrated of course. I had done this a time or two before with some of my other clients, and had enjoyed it immensely.
We were nearing the restaurant when I reached over and began stroking his cock through his pants. It responded immediately; springing to attention. I continued playing with it as he circled the parking lot looking for a place to park. Once we were parked I pulled out a hot pink lace thong and handed it to him.
“Put that in your pocket, and once we are seated you are to go into the bathroom and put that on and bring me your underwear. Do you understand me?”
His eyes bulged at the thong he was holding, “Yes Ma’am.”
He stuffed the thong into his pocket and got out of the car. He held the door for me as I got out of the car, and I led the way to the restaurant. He held the door for me and I went in, walking right up to the hostess. I informed her of my name and what seating I would require. She showed us to a table and placed menus before us, informing us that a waitress would be along shortly.
I looked straight at Dean and said, “Now would be a good time for you to go to the bathroom darling. You know what you have to do.”
He bowed his head and said, “Yes Ma’am,” and left the table in search of the men’s restroom. I silently collected his menu, and smiled. Within minutes of his leaving a waitress had arrived to take our orders. I ordered drinks for us and asked her to give us a few more minutes to peruse the menu. Of course, I already knew what I was going to have, and I fully intended to order for Dean as well. He came back just as the waitress arrived with our drinks.
“Please do sit down Dean, don’t stand there looking so foolish.”
He blushed and sat down, and the waitress placed our drinks on the table for us. She looked at Dean and asked if we were ready to order.
“Yes indeed, I will have the shrimp fettuccini alfredo with garden salad, and please substitute cottage cheese for the dressing.”
“Yes Ma’am,” the waitress replied turning to Dean, “and what will you have sir?”
Dean blushed bright red. He had not had a chance to see the menu, and in fact there was no menu in front of him to even look at. His eyes met mine, and I smiled viciously. Dean’s napkin had suddenly developed a bulge under it.
“My little Dee-Dee will have an order of lasagna and a garden salad with cottage cheese. Thank-you.”
The waitress took the menus that I was holding out to her, grinned slightly, raised an eyebrow, stole a glance at Dean, and said that she would be right out with our salads. I looked at Dean and could see that his face was still a bright red, and he was looking at the napkin in his lap.
“Don’t you have something for me dear?” I asked sweetly.
“I…well…I…uh…you want me to give them to you now?” He seemed stunned that I would ask for them.
I smiled wickedly, “Yes of course I do! Hand them over!”
He stole glances to his left and right, and I’m sure he was hoping that no one would see as he pulled his black underwear out of his pocket. He reached down under the table quickly, trying to hand them to me. I laughed at his silly efforts.
“No dear, hand them to me please,” I said as I held out my hand expectantly over the table.
He had no choice but to pull his hand from under the table and place his underwear in my outstretched hand. I smiled again as I held them up for inspection with both hands. They were clean and serviceable with no stains, tears, or rips. He bowed his head and I’m sure he was quite humiliated. He was also still quite turned on I noticed.
“Very nice,” I said still smiling, putting them in my purse. Seconds later our waitress arrived with our salads. I thanked her, and began eating. I had to encourage Dean to eat his.
“C’mon Dee-Dee, eat your salad. It’s good for you.”
“Yes Ma’am,” he said sheepishly and began to munch on his salad. I began chatting to him about the weather, and my vacation plans for next year. He started to relax and by the time our salads were done he was no longer blushing. I fished into my purse and pulled out a medium butt plug. I handed it to him across the table, and he quickly tucked it under his napkin and into his pocket.
“Be a good boy and go to the bathroom and take care of that for me, won’t you?”
“You want me to do that HERE?” He asked incredulously.
“Of course!” I said brightly. “It would please me very much!”
He quietly laid his napkin aside and asked, “What should I use for lube?”
“Oh! Here you are!” I handed over a small sample tube of lube, and he glanced sideways tucking it into his other pants pocket.
“I want you to go now Dee-Dee, before our main courses get here.”
“Yes Ma’am,” he said as he got up to leave.
A few minutes later he returned to the table and sat down carefully in his chair. He kept stealing glances at the other patrons wondering if they could see that we were different from them.
“Dee-Dee, you look so ‘tight.’ You really should loosen up a little!” I activated the wireless remote control in my pocket for the butt plug Dee-Dee had just inserted, and watched as he jumped in his chair as it began to vibrate in his ass. He blushed bright red as the waitress arrived with our main courses. She had heard what I had said of course, but had no idea what I had meant by it. To her he was indeed acting a bit uptight, and needed to loosen up.
“Would you like me to bring you both another drink?” She said, this time looking directly at me.
“Yes, I think that would be lovely, but don’t bring another one for Dee-Dee. He can’t hold his liquor like he used to.”
“Yes Ma’am,” she said, and left to fetch me another drink.
I turned the vibrator off, and watched as Dee-Dee relaxed and his napkin fell to the floor. He retrieved his napkin and I turned the vibrator back on again. He flinched again in surprise, but managed to fold his napkin over his fully erect cock. We ate quietly after the waitress brought me my second drink and I reached under the table and brushed his leg with my foot.
“This is delicious isn’t it dear?”
“Yes Ma’am,” he replied knowing full well that I wasn’t referring to the food.
I let the vibrator run for a while, and then turned it off. Dee-Dee relaxed visibly, and ate in silence with his eyes on his plate. Had we been in a BDSM club I would have had him eating at my feet, preferably off the floor and naked.
When we were finished eating, I had the waitress bring our check. When he didn’t whip his wallet right out it gave me the opportunity to reprimand him again.
“Be a good boy Dean and pay the nice waitress,” I scolded as I activated the vibrator on the butt plug again.
He pulled out his wallet, wincing as he shifted his weight and wiggled the butt plug in his ass. He handed the waitress a credit card, and I spoke up telling her to be sure and add a 20% tip for herself. She smiled widely and nodded, as Dean hung his head.
“Don’t worry dearest,” I said to him “this won’t cost you any more than what you usually pay me.”
The waitress returned with his credit card and a receipt for him to sign. Much to his relief he saw that I had told the truth. The bill was only slightly more than what he usually paid me.
With that taken care of I turned the vibrator off again and we exited the restaurant and he drove me back to my office. When we were a mile or so away I spoke up.
“That was lovely Dee-Dee, we should do that again sometime.”
“Yes Ma’am, we should.”
“Of course, the evening isn’t over yet.”
“Ma’am?”
“Well no, it’s not. You have my butt plug up your ass, and I have your underwear. It seems that you are going to have to earn your underwear back.” I smiled knowingly.
Dean hung his head and said, “Yes Ma’am.” He already knew what I was going to make him do.
When we arrived at my office I unlocked the door, turned the lights on, and went in. Dean closed the door behind him, and I instructed him to sign the standard release form, and proceed to the dungeon. I had him trained now so that he knew exactly what to do.
When I walked into the dungeon he was kneeling naked on the floor. What a sweet sub he was turning into. His clothes lay folded neatly on the dungeon table. I walked over and picked up the wrist restraints. Call me greedy, but I wanted tonight to be special right to the end. I picked up my clean strap-on and fitted a larger dildo into place than what I had previously used. I lubed it up and strapped it on.
“Come dear,” I whispered into his ear, “I have something special planned for you tonight.” I noticed that he shivered as I buckled the wrist cuffs onto his arms.
I led him to the small room off the dungeon that he had never been in before. In fact, few of my clients were ever allowed in there. It was a bedroom with lavish furnishings of various shades of red and black. I made him lay down in the middle of the bed on his back. I attached the wrist cuffs to the headboard of the bed and stood over him.
“Would you like me to take that butt plug out Dee-Dee?” I asked sweetly as I turned the vibrator on again.
“Yes Ma’am.”
“Hmmmm, you don’t sound very convincing.”
“Ma’am, please take the butt plug out.”
I laughed loudly in his face. “Not unless you can beg better than that!”
He began to beg then in earnest, realizing that he might very well end up spending the night there.
“Ma’am pleeeease take the butt plug out of my ass, I’m not worthy to wear it anymore! I have disappointed you tonight, and I’m not worthy of your time and attention! Pleeeeeeeease take it out Ma’am! Pleeeeeease!”
“You are pathetic!” I said as I circled the bed. “Surely, you can do better than that.”
“Ma’am, pleeeease take the butt plug out of my ass! Please, please, please! I have tried to be a good sub tonight! I have tried to do everything that you asked of me! I know I still have a lot to learn, but you are a good Mistress, and you will teach me everything in time! I know how much you enjoy using me! Please Mistress, take the butt plug out of my ass and use me! I want you to be happy! You have been sooooo good to me tonight, and I am unworthy of you!”
I reached down and took his jaw in my hand turning his face to look at me.
“You are absolutely right. You are a miserable sub. You are not worthy of my time and attention! You are here only to please me.”
I released his jaw and he closed his eyes and turned his face away from me. I turned the butt plug off and pulled it roughly from his ass. He gasped and groaned, and his sharp intake of breath told me I had him right where I wanted him.
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