A Purchased Evening Pt. 01

A darkly dressed gentleman in his mid-30's sat at the tale for two, still alone but with the air of someone waiting for his company to arrive. He was tall, not really athletic but still had a good presence around him, Dark hair and brown eyes blended well with the dark clothes he was wearing. He sat browsing through the menu at first, and then later his phone as the restaurant buzzed around him. He was about halfway through reading article when he looked up and saw his date walking across the restaurant, wearing a low-slung white dress and matching heels. He put his phone down and stood, moving over to her as she reached the table.

"Lindsay?" He asked, cautiously.

She nodded once, standing in front of him, feeling his eyes scan her up and down. He motioned to her to sit, pulling out the chair for her as she sat down and then went back to his own seat.

Taking his own seat, he studied her for a second again. She was young,, he could tell, probably barely 18. Her hair was dyed blonde, you could see the roots showing brown. She was short but the dress filled out well, his eyes kept being drawn to the split between her boobs. He had to force himself to look at her eyes as he began to speak.

"Hello, Lindsay. My name is Matt, and the firm didn't lie when they said they had some beautiful providers on call, it would seem," he said with a smile.

"Thank you, Matt," she said with a blush and smile. She was still relatively new to the firm, this was only her third booking and while the first two had been nothing to write home about, this was the first one she had been asked to show up and have dinner with the client first. That was different, she thought, looking him over. He seemed confident in himself, which was a little different from her previous encounters. She caught him ogling her breasts in the dress and smiled a little bit before picking up her menu.

They sat in companionable silence for a moment as she looked over the menu, setting it down just as their waiter approached.

"How are you all doing today?" the young gentleman asked. "Drinks to get started?"

Matt ordered a fruit juice blend, not really into drinking soda or alcohol. Lindsay ordered a water and a virgin cocktail and the waiter disappeared. Once he was gone, Matt slid a small envelope from his pocket and pushed it across the table. "To say thank you for joining me tonight," he said, watching her pick it up and slip it into her purse."

"It does feel a little weird," she said slowly. "We are just having dinner tonight?" she asked carefully.

He nodded once, just as the waiter returned with their drinks. He ordered a big double burger and fries, she ordered a chicken caesar salad with extra dressing. The waiter disappeared again.

"Yes, just dinner tonight, I'm afraid," he said, looking at her carefully. "I wanted to have a chance to meet you and explain what our arrangement would mean for you. I want you to know that once i spill all the details, if you would like to say 'no, thank you,' i am okay with that, and you will still receive a five-star rating from me for your employers. So please don't think that you are obligated to say yes," he paused, watching her reaction as he paused. He saw a slight line of confusion appear on her forehead, and then continued.

"Especially now that I've seen you, Lindsay, I'd be lying if I said I didn't want to try to put my dick through you. And if you agree to see me again, believe me, I will do exactly that. I've never really been one for slow, vanilla sex," he said with a laugh, sliding a picture across the table. The picture was a grouping of sex toys, including a flogger, butt plug, cuffs, rope, clamps, a collar and a few other things Lindsay didn't quite recognize, holding the picture and blushing.

"You want to use these on me?" she asked quietly, studying the picture so he couldn't see the blush on her face.

"Yes, and probably a few others that are not pictured there. You should know that when you are with me, you are mine, and I will take whatever I want from you, and it may not always feel good. " He let her study the picture for a moment before continuing. "The most important thing for you to know, however, is that the entire enterprise is based on your consent. Without it, there is nothing. If you decide to have me as a regular client, you will have a safeword, and you have my solemn vow to honor it, should you ever use it. I like to have fun, yes, but it's no longer fun if you are not willing to participate."

Listening to him speak about consent, she put the picture down and studied him closely. She had fantasies of being tied up, controlled, things she had never really had a chance to explore with anyone before because most people either were too vanilla or couldn't last very long in the bedroom.

Seeing her studying him, he continued. "You are absolutely gorgeous, Lindsay, and I would do everything in my power to have you drooling, begging for release from me like a good little pet," he said, pausing as he saw the waiter arriving with their food. He disappeared again after setting their plates down.

They ate in silence for a few minutes, she was contemplating what he had said to her, letting her mind drift a little to the possibility of having some of her fantasies fulfilled. The cash helped, she thought, but he was very direct about what he wanted, and it made her pussy tingle a little bit. She might do this without the cash. She pushed her mostly finished salad away, and sat, looking at him as he finished his food.

Seeing her finish, he wiped his fingers with the napkin and looked at her again. "Remember, you can tell me no and I will still give you high marks for the firm. There is no obligation here. I only want you to do this if you feel it will be something you would enjoy."

She giggled at that. "So as far as today, there is nothing else you wanted to do?" She asked carefully. "Just dinner?"

He nodded. "Once we're done here you are free to leave. If you agree, I will text you with a time and an address where you should show up, along with maybe a few other instructions," he said with a shrug.

Lindsay had become used to guys wanting to fuck her on the spot. It was a hard truth of being a beautiful, young woman in the world we lived in. Being able to watch as guys (and some girls) undressed her with their eyes was something she had gotten used to. It didn't seem quite real yet that she was getting paid just to have dinner.

"I think," she said, picking up the picture of all the toys again, looking at it for a second before setting it back down and sliding it towards him, "that I am all-in on this. You seem like a good guy, and to be honest, the things you mention are things I've wanted to try but haven't found a good partner for. So, yes," she said, breathlessly as she looked up at him for approval.

He smiled, and took a thicker envelope from his pocket, sliding it across to her. "This one is specifically for you, just some money for any clothes you may need to buy, or anything else you might need for when we are together. If you ever find yourself in need of something, you are free to call me, should the need arise."

She opened this envelope, surprised to find $1,000 inside. She quickly closed it up, holding it up. "You're sure about this? That's a lot of money," she said.

He smiled. "Consider it a bonus. Now, let's go ahead and decide on your safewords now, so that way we can have it already decided before we meet again. Did you have one in mind?"

She considered for a moment. "Periwinkle," she said quietly.

"Periwinkle?" he asked, "That's kind of random," he laughed.

"Maybe," she said, smiling, "but its also not something that I would normally say during sex, either," she shrugged.

"Alright," he said, "I will also tell you this, because there will be times when you will be gagged or, uh, otherwise have your mouth full. If I ever hear four repeated grunts, I will stop immediately and allow you to speak freely, whatever that may require. Removing gags, whatever. In any case, if you ever decide to use the safeword (or safe-grunt), I will immediately stop and check in with you. If you want to stop, altogether, we can, or if you just want to change what we're doing, or just have me lighten up a little, these are all valid uses for the safeword, okay?"

She nodded, seeing the waiter return with the check, depositing it on the table as he cleared the plates. He laid his credit card down over the check and turned back to the girl across from him. "Do you have any questions for me?" he asked.

She considered for a moment, before shaking her head. "Not really, just... when are you thinking we will meet again?"

He smiled, his eyes dropping down to see the split of her tits in the dress she wore again before meeting her eyes. "Oh, it won't be more than a couple of days," he said, with a smile as he stood. "Do you have a car here?" He asked.

She nodded. "Do you mind if I walk you outside?" He asked, offering his arm. She took it, letting him escort her outside to her car. She pointed to a white, older BMW and he guided her over to it.

"Miss Lindsay, I must say I am looking forward to our next encounter. Until then, stay safe, and take care of yourself," he said, reaching down to hug her carefully before opening her car door for her.

"Thank you, and you as well!' she put out as her door closed. She watched as he walked over to a sporty-looking black car, got in and disappeared.