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."
She circled him now, looking for the opening she sought. When she found it, she stopped. "And the next time you try to get off on someone else's pain, I want you to remember this."
She put all she had into it, and the kick connected squarely with his exposed nuts. The air went from him, and both hands went between his legs. He was gagging, gasping for air, and she leaned over.
"Ciao, Bradford Fuckin' Loser Tokien the Fourth."
She scooped the scattered items back into her purse, put the purse over her shoulder, stepped around his writhing figure, and went to the door. She heard him retching as she closed the door behind her.
On the train ride home, she phoned the Agency and told them what happened. She was shaking so badly she dropped the phone three times before managing to get the call through. They confirmed the penalty clause would be enforced, and Bradford Tolkien would never again be permitted to escort one of their ladies.
She sat alone in a dark corner of the train car, far away from the other five or so passengers, and watched the dark trees and roads speed past. Her tears didn't stop until she fell into her own bed and fell into dark, turbulent dreams filled with Bradford Tolkien IV. * * *
The evening had been a whirlwind. He'd arrived at the Club at five thirty, dinner with Mike and Justine, dancing to the jazz combo after. He'd run into Alexis, there with her husband, and they'd danced.
They were dancing again, slowly, to a soft version of some old Coltrane tune. He hummed along, trying to remember the name.
"I think Harry's left," she whispered into his ear.
He looked at her. He was feeling the drink, but he could still read the look. He pulled her in closer. "Then I'll give you a lift when this is over."
He felt her hands squeeze his shoulders. "That's not what I meant." Her voice was scratchy, sexy. He knew what she wanted, but he didn't answer.
She was tall, nearly as tall as him, with long blonde hair and a long, smiling face. She laughed easily, chuckling while she spoke, and David thought that was the sexiest thing about her. The tight, low-cut dress didn't hurt, either. Her breasts, though neither large nor small, were well served by her outfit, and she was now pushing them into him again. He felt her hard nipples against his dress shirt and tried to banish the thoughts from his mind.
"He won't care, you know. Harry won't. That's why he left me here. With you." She was giggling as she said it, a low, scratchy giggle, and it was intoxicating.
"How do you know. Maybe he just-- "
"Because we talked about it over dinner, silly."
He suspected as much. Once, about a month after the swingers night at Mike's, he'd gone to another one. He'd seen Alexis and Harry there, on a sofa in a corner of the basement. Alexis was on her knees, giving a long, sloppy blowjob to some guy while Harry sat next to him, watching and jerking himself off. Harry saw him and waved, and he'd waved back before leaving. He'd never gone back.
He and Cynthia had been friends with Harry and Alexis for more than ten years, gone out together, danced together. He'd never gotten even an inkling they were into this scene. But the whole thing made him realize that he didn't want to become a part of the scene. It also made him realize just how little he knew about his friends, and, in combination with Cynthia's betrayal, underscored how naive he was about sex.
"So what d'ya say?" she giggled.
"I say I'm taking you home." "My place or yours?"
"Yours."
She giggled. "Harry will like that."
David laughed.
Ten minutes later, they were pulling from the Club in David's Lexus. She was splayed across the passenger seat, her legs askew and pushing her dress to her hips. "It's a long drive," she said. He looked over and watched her eyebrows arch as her hand slid down her belly and into her panties. "Wanna play?"
His eyes went back to the road. She was insatiable, he thought. Even drunk, her voice exuded sexuality. No, there was more. Fun sexuality, he decided. She really was a fun person in all things, and she clearly wanted him to share in that fun.
"Seen Cynthia lately?" He hadn't seen her in nearly a month, since the night with Aimee.
He felt her hand reach over and rest on his lap. "Why you wanna know?"
"Just haven't seen her. Wondering how she's doing."
He felt fingertips trace the outline of his bulge, felt himself getting aroused.
