The Real Deal

Part 7 - What She Does Best

Cassie sat quite uncomfortably on the high chair. She was forced to sit with cross legs because of the shortness of her skirt but the chair's footrests were too low so she just balanced on a stiletto heel. It was her first date as a sugarbabe and she had picked her outfit carefully. She wore a black suede skirt with a sheer crop top over a lacy bra. She wanted to look like herself but a sexier version. She had topped it with a pair of stiletto boots with a pointed toe. The guy was just a few years older than her, working in IT. They had met at a French bistro to eat oysters and drink champagne. It felt like a thing she would do with Bill so she felt comfortable. The guy actually reminded her of him. He didn’t possess that unique beauty that Bill had but he was just as tall and pale and fidgeted with everything he could reach. He watched her like she was a goddess of sex and it made Cassie feel that it was right. That doing it wasn't so weird after all.
"Have you lived here in New York for a long time?" He asked while dragging his napkin between his fingers.
"Like four years. You?"
"Just a year. I haven't really learned the city yet…"
Cassie nodded and thought to herself that he probably was lonely, that's why he was seeing her.
"Do you party a lot?" He asked and took a swig of the champagne.
"No… It's really not my thing."
She didn't want to tell him that she didn't really have any close friends. That the ones she called friends would probably disappear when she got a new job. The only close friend she had was Bill.
"Maybe you do other wild stuff?" He asked and bit his lip. She started to understand where he was going and with some nerves she laid her hand on his knee.
"I can be wild with you."
He closed his eyes and shuddered with delight.
"What are you wearing under that skirt, bad girl?” He asked with a low voice. She moved a little, spread her legs so he could see the lace hem of her thigh highs. If he leaned down he would also see the black lace of her panties, which he did. His eyes were heavy and once again he reminded her of Bill.
"Fuck… You are the sexiest girl I've met. I just want to play with that pussy. You're shaved, right?"
"Yeah," she said and tried to be natural even if it felt odd that a guy talked about her pubic hair in a restaurant.
"What do you do?"
"What do you mean?" Cassie felt stupid. Wasn't it sex he wanted?
"Bondage, spanking, threesome, anal, water sports… You name it."
He definitely didn't remind her of Bill when he talked like that. Bill could joke about sex but he would never ask such thing and definitely not without getting pink in the cheeks.
"Oh… I don't do butt things, or pee and… those things." 
The guy smirked and nodded a little. Cassie tried to hide how nervous she’d gotten but she could see that he noticed.
"Too bad but I still want to take you to my hotel room if that's okay?"
She tried to put on that sexy role again and smiled.
"That sounds good."

It was obvious what they would do in the hotel room and the guy didn't even try to hide that. As soon as they were in the room he was on her. It wasn't unpleasant but not  impressive either. He wanted to show himself as sexy, dominant and a bit mean but he fell flat. Cassie was near laughter every time he tried too hard to be some sort of Mr. Gray but she faked it. Everything from the fire in her eyes to an orgasm. Maybe Bill had taught her some acting under their long friendship.

They had an awkward goodbye, the money he had already sent to her Paypal at the restaurant. She left him pleased, drained and with a confidence on fire. She went home with 800 dollars, blushed ass cheeks and a new experience. Maybe she should have felt ashamed. She was a whore now, literally and had let a guy call her that while emptied his seed on her face but she just had spa treatments and Chloe handbags on her mind. A facial for a facial.

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Bill laid a hand on Cassie's hips, he didn't need to guide her because she knew what she was doing, he just wanted to feel with his hands how her hip bones moved. He was fully hard now and could see that Cassie was so wet her panties stuck to her skin.
"You're a big boy, right?" She said with a mischievous voice while crawling down to lay between his long legs. Bill didn't know what to say so he just smiled. Cassie looked at the imprint on his boxers. It was obvious he was big but not scary so, just the way it probably would fill her up better without being a struggle.