Her client this chilly autumn night was Bradford Tolkien IV, thirty-year old scion of a wealthy banking family from the North Shore. She had accompanied him to dinner with the family, at which he'd introduced her as an old college girlfriend. Despite the obvious difference in their ages, no one commented.
She didn't like him. Sure, he was handsome. They all were, especially the wealthy ones. He was smart, too, and witty. But there was a caustic streak to his wit and an arrogance about him that set her off. She saw the same features in his father, but they were magnified in her client.
After dinner and cocktails at the bar, they slid into his Porsche and drove to his apartment. The twenty-minute drive was dominated by him telling her how good he was at work and how bumbling everyone else was. She'd heard this a million times before--they were all, to varying degrees--consumed by themselves and confident bordering on arrogant. He, however, stressed the quality of bloodlines, which unnerved her yet further.
When they arrived, they took the elevator to the forty-fourth floor and entered a spacious condo with a beautiful view overlooking Lake Michigan. She stood at the window with her back to him, watching the blinking lights from the breakwaters and the lighthouse. To the right, she saw the bright lights of the Chicago shoreline stretch for miles until it curved around as it reached Indiana.
"It's beautiful," she said.
"Just what I was thinking," he said behind her.
She stiffened as he reached under her dress and tore her panties down. His hand went back up and pushed into her vagina. She wasn't ready yet, and it hurt as he roughly forced a finger into her.
"You just enjoy the view while I enjoy you." With that, he pushed her upper body against the window and pulled her hips back out, his arm circling her waist and holding her there.
She looked back over her shoulder and said, "Settle down, Tiger. Let me get you ready."
His face was a mask of contempt. "I am ready." She felt him push against her dry lips.
"But I'm not."
"Not my fucking problem," he leered.
He thrust into her, and she gasped with the tearing pain. She turned back and faced the window, looking again at the lights before looking down and resting the top of her head against the window. She grimaced, trying to will herself to relax. She reached a hand underneath, seeking her clit.
He pushed her hand away and thrust into her harder and faster. "Don't bother," he said. "I'll get you going."
But he wouldn't, she realized. He was into pain, and he enjoyed her pain. Some of the other girls had warned there were occasional clients like this, but she'd never been with one. Now she knew what they were talking about. Tears started welling in her eyes as she leaned there and accepted his pummeling.
"Tell me how it feels, whore."
She said nothing, only grunting with the force of his thrusts. She felt a little moisture forming to protect her from the attack, but it wasn't enough to prevent the searing pain.
He started thrusting faster. "I asked you a question, slut." He punctuated this with the hardest, deepest jab yet and her tears started streaming.
"You're hurting me," she cried.
This only excited him more, and he kept up the hard, deep shoving in and out.
"Tell me how it hurts."
She didn't hesitate this time. "Like you're tearing me apart."
Maybe if she didn't cry, he'd lose interest. She tried to get the tears to stop. Then she felt him force a finger into her anus, and she threw her head back and stifled a scream.
"Oh yeah," he said, pushing deeper into her. "You think this hurts, just wait 'til I go in there."
"No," she cried. "Get it out. You know the rules. They told you when you called."
"Fuck the rules."
"But they took seventy-five hundred from your credit card. They'll keep it all if you break the rules."
He increased the speed of his hips and pushed his finger all the way in. "This is a virgin ass, isn't it?" When she didn't answer, he pushed his finger in hard. "I said-- "
"Yes. Yes, it's a virgin ass."
"I'd gladly pay an extra five grand to tear apart this tight virgin ass." He started moving the finger in and out. She was terrified. Her legs were way behind her, spread too wide to give her leverage. The arm clamped tight around her waist prevented her from twisting. She knew if she tried to hit him or kick him it would only get worse. That's what they'd told her. Just take it, try to think of better places, and pray to God you got out of there in one piece.
She opened her eyes. Through her tears, she saw her purse on the ground below her. She must've dropped it when he pushed her into the window and got her ready for him. She reached toward it, but he slammed her forward with a deep thrust.
"What're you doing?"
"Lube," she said. "It's in my purse."
He laughed at her. "You're not getting any lube, bitch."
She knew she couldn't reason with him, so she tried the only tactic she thought would work.
"Listen, baby," she said, her voice going low. "You're just so big. I've never had such a big cock before. That's why it hurts so bad."
"Yeah baby, take that big cock." His speed slowed a little as he listened to her.
"And my ass is tight. You don't get some lube on that monster, you'll never even get it in, baby."
He said nothing, but his slower thrusting told her he was thinking about it. She poured it on.
"Baby, you're so fucking huge you're gonna tear it apart either way. Might as well make sure you can at least get into it, right?"
She felt his finger pull out of her ass. Arrogant bastard, he really thought he had a monster cock?
"Yeah," he said, reaching his hand around her side. "Better give me some."
He stopped his thrusting, allowing her to reach into the purse. She fumbled around, looking for it.
"What's taking so long?" He thrust into her, making her yelp. "Hurry the fuck up."
She felt her hands brush the cool metal, and she grabbed it and pulled it from the bottom of the purse, spilling half the contents on the floor. "Got it, baby."
"Then hand it here."
She got her grip on in and twisted her back to look at him. He loosened the grip around her waist slightly, and her arm shot out to his face.
"You fucking bastard," she hissed, pressing her finger down and sending the pepper spray straight into his eyes.
His hands released her and shot to his face, his screams getting louder. She didn't release her finger, sending it over her hands then directing it down to his sagging cock.
"You into pain, you fuckin' freak? How's this for pain?"
One of his hands went to cover his exposed manhood and he tried to back away from her. The hand went away from his eyes and tried to swing out at her, but she stepped aside the flailing arm and directed the can back at his face.
"You fucking bitch." He crumpled to the ground, going into a fetal position and trying to cover his exposed skin. "You fuckin' whore, you'll pay for this."
She stepped behind him. "No," she said, "you'll pay for this. Seventy-five hundred, to be exact. You broke the rules."
"But I didn't get into-- "
"Doesn't matter. You tried to, and that's enough."