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As they sat at their table, the conversation turned extremely vanilla, exactly the things that you’d talk about on a first date as you’re getting to know someone. He laughed as he explained how he feels he ‘eats like a child’ because he detests most vegetables, but will pretend to like them in social settings choking down a salad when needed. She talked about her love of food and how working in the service industry at a young age gave her a certain level of respect for every waitress and bartender. By the time their waitress approached, his earlier humiliation had faded, and he was feeling extremely confident. The young woman dressed in white with a striped tie beneath her apron looked at him, and asked if they were ready to order.
“Yes, I think we are, I’ll start with the,” he stopped suddenly as he received a swift kick under the table, so hard he had to catch his breath. “I mean, are you ready Mistress?”
He tried his best to hide how much pain he was in as she ordered an appetizer and entree for herself before saying her ‘companion’ will have the Classic Caesar Salad and a glass of still water. By the look on her face, he could tell he was in trouble. The waitress collected their menus and walked away.
“You are always submissive to me, whether we’re ordering food, or I am using my biggest black cock to destroy your asshole – I am in charge,” she raised her voice at the end, drawing some side eye from nearby tables. “Now go into the bathroom and put this in, and make sure you turn it on.”
She reached in her purse and placed a medium size, black butt plug on the table in front of him. The fact that everything on the table was completely white really made it stand out. He quickly reached for it and pulled it into his lap. As he felt it, he knew this plug, it was the kind controlled through the Lovense app, so he knew exactly where things were headed. He slipped it into his pocket and made his way to the bathroom, there was a part of him happy that on this journey through the crowd his hard on had subsided and pants had dried. He had used these enough in the past that he knew how to insert it, even without lube. He went into the stall and instinctively put the plug in his mouth and started the self-lubrication process. As he did, he felt his phone buzz, it was a simple message from my Mistress – ‘send me a pic of you right now!’ He quickly snapped a selfie with the black plug in his mouth and sent. He then lowered the toilet seat and sat down as he inserted the plug into his asshole, sitting on it to make sure it was all the way in. As he walked back, his gait had changed noticeably as he tried to make sure the plug stayed in place. As soon as he could see her, he saw her take out her phone and he knew what was coming next – she sent a series of pulses and vibrations to his anal accessory making him stop and take notice.
After he sat back down, the next hour of dinner was a completely balanced between mostly vanilla topics that made up their earlier conversation, and direct instructions on what she liked and how she wanted to be served. He knew exactly when to make a mental note, because she would always confirm he understood when it was something that was important to her. However, as she suggested they pass on dessert, but share an after-dinner cocktail, her demeanor and tone changed. She ordered two glasses of Tawny Port, and moved her seat much closer to his.
“Just so you’re aware, your commitment to me is both permanent, and all encompassing,” she took her right hand and ran it up her thigh under her dress as she spoke. “You will be expected to serve as a service slave typically would, but you will also have to keep me satisfied sexually. And I am a very sexual woman.”
As she made sure he understood exactly what she was saying, and as she did, she slid two fingers inside herself. She was so wet, she could feel her juices dripping down her leg. She pulled out her fingers and lovingly stroked his face with that same hand, being sure to cover him in her scent.
“I am ready to leave now, get our coats and call a car,” she stood up as he picked up his phone and scrambled to the coat check, raising her glass and finishing her drink in a mock toast as he returned. “Such an obedient boy, here’s to hoping you’re as successful in the next task I have for you.”
This time through the restaurant, they took the most direct way to the door, and right outside was an awaiting black Cadillac Escalade. He opened the door and let her inside. As she adjusted herself in her seat, she pulled up her dress creating easy access to her swollen clit.
“You have until the car reaches the hotel to make me cum using only your hand,” she whispered in his ear as she took his right hand and put it under her black leather dress. “If you succeed, you will enjoy a reward; but if you fail, you will not enjoy the punishment.”
He immediately started using two fingers to stimulate the outside of her swollen clit, as he did, she instinctively reached down and grabbed his swollen cock beginning to stroke. He was completely focused on his task, but he could not ignore the fact she had him ready to explode if not for the tight leather strap holding it back. As he explored her dripping pussy with two fingers, then three, she used everything she had to hold back from cumming – she had a plan and she was going to make sure it happened. By the time they were a block away, she was biting down so hard, it felt like she was going to put a hole in her lip.
“Stop, hands off,” she whispered as they sat at the light at the other side of Bryant Park, continuing to stroke his cock more ferociously. “You failed, and now you’ll be punished immediately.”
She continued to jerk him until she knew he had no control over his release. She reached down with her hand and pulled off the leather cock ring and pulled back her hand. His cock spasmed and twitched as he released a week’s worth of built up frustration all over himself. He had literally never came so much in his life. He pulled his coat closed to hide it as they pulled in front of the hotel.
“It is freezing out there,” she said as the Uber driver came around to open the door. “Be a gentleman, and let me wear your coat so I don’t freeze dear.”
Source: reddit.com/r/Erotica/comments/101ai7b/a_slippery_slope_part_6_romantic_bdsm_femdom