The car stopped at 80 Columbus Circle, right in front of prestigious, nearly $700 a night Mandarin Oriental Hotel. This wouldn’t be his first time here, not by a long shot. He could remember many romantic nights and mornings rolling around in the satin sheets, his body intertwined with Marcela's, their tongues curling and twisting and darting out of one another’s mouths. Just thinking back to those good old times made his cock beat and throb in his pants. But that’s not what he wanted or needed, at least not yet. For the meantime, he needed to have complete control of himself because if he was unable to do that there was no way that he would be able to control the girl and that was his ultimate goal. He was going to be in complete control of this sweet Valentine’s Day encounter and she would be his slave, his obedient, dutiful slave, just like Marcela had been before she’d finally packed her bags, hopped on a flight at LaGuardia and headed back to Buenos Aires. Her departure had come as such a shock to him—a shock that he still hadn’t gotten over so many years later.
Chapter 3
Cara looked at the flashing screen on her phone. It was the agency calling and it turned out to be good news, very good news but she couldn’t help feeling that maybe the news was a little too good.
"If you stay with him for the next 72 hours, doing everything that he says, he’ll pay you $100,000."
"What?" Cara gasped. She must have heard that wrong. There was no way a client could be offering that much.
"Have you checked this guy out?" Cara asked. "How do you know that this isn’t some type of set up?"
There was a fit of laughter on the other end of the line. "You ask a lot of questions," the dispatcher said. "You should learn to keep your mouth shut and do your job."
Before Cara could fire back an angry response, the phone clicked off. She gritted her teeth and glared at the screen. What a fucking asshole! She said under her breath. Then she remembered the number that the client was willing to pay to spend time with her.
Her phone beeped and the screen lit up. The agency had texted her the rendezvous spot. After giving the driver the directions, Cara sat back in the seat and smiled. She pulled a cigarette out of her purse, lit it, and blew the first big puff of smoke out the window into the night’s sky.
"You’re not supposed to smoke," the cab driver said, shaking his head.
Inhaling deeply and blowing out large mouthfuls of smoke, while her mind jostled with a myriad of disconnected thoughts, Cara ignored the driver. This was going to be one of the craziest nights of her life.
Chapter 4
When Cara walked into the hotel room, She immediately locked eye with Bradley. The way he looked at her made her entire body tingle with desire. After a bit of small talk, they soon began tearing at each other’s clothes, falling onto the bed, rolling around and around.
They stayed in bed for the next couple of hours. They hadn’t yet exchanged many words but Cara could feel the intimacy slowly growing between them. She wondered whether or not he’d been quiet and hesitant to talk about himself because of his shyness or maybe there was something else holding him back from expressing himself. There was something in his eyes, smoldering green and deep set that made her heart skip a beat each time he looked at her.
Cara couldn't hold back anymore. She had to know what was on his mind. She stared deeply into his eyes and brushed a tangle of hair from his face.
“You still haven't told me why you wanted to spend Valentine’s Day with a girl that you don’t even know. An escort,” she said.
He looked away. There was so much more that she wanted to ask, but she almost felt guilty for forcing the issue. It really wasn't her business. She had a job to do, entertaining him, taking his mind off his pain and making him laugh and smile. That's all he hired her to do – or at least, that's what she’d thought. But from the moment she walked in that door, she had the feeling that there was something more to this transaction. Bradley wanted more than just a weekend of fun and fucking and that was fine with her. It would be a change from all the standard encounters that she had with her clients: walk in, take the money, small talk, fuck, get dressed, and plan to meet up in a week or so.
Bradley sighed deeply and raised his eyes to meet hers. There was so much emotion in that expression, so much raw emotion burning to be let out. He sighed again and shook his head, mumbling something under his breath.
Cara looked at him with a pained expression. “I'm sorry if I said something to offend you,” she said. “It's just…No one ever… no one's ever hired me to do something like this before, so I’m just a little curious.”
“It's okay,” Bradley said running a finger down her cheek gently, as he stared deeply into her eyes.
“It's a long story,” he said. “I'll try to make it short but, I won't be able to make it sweet, no matter how much I try.”
He smiled and shook his head. His face was full of sadness and bitterness but there was also something courageous there as if he were battling against the demons, trying to exorcise them, so he could move forward with his life. That's what this whole weekend was about, this crazy 72-hour date that would end up costing him $100,000 if Cara was able to stay for the full three days. What nonsense! What was he thinking? It didn't make any sense, but somehow to him it did.
Seven years ago on Valentine's Day, the woman whom he thought was the love of his life had left him. But maybe left him isn't the right way to say it, because she actually didn't even bother to show up. They were supposed to spend three days together at his home in the Hamptons. It was going to be the third Valentine's Day that they’d spent together and in Bradley's mind it was going to be the most special of them all. Why? Because he was prepared to take a step, a bold step, one that he'd been avoiding for so many years, one that he thought he would never take.
That Valentine's Day would mark the end of his bachelorhood. Bradley Jennings would be retiring from the New York single scene, a scene that he’d dominated for many years, hopping in and out of beds with some of the most beautiful and desired women in the city, but never taking any of them seriously. That was until he met the stunning 6-foot blonde model from the pampas of Argentina, Marcela Ignacio. He’d been smitten from the start. Never before had he met a woman who made him want to leave the single life behind, settle down, start a family, and begin doing all those things responsible adults were supposed to do, all those things that he’d been avoiding doing while he enjoyed his billionaire playboy life.
Everything seemed to be going so well, at least in his mind. If he’d paid a little bit more attention to Marcela leading up to that Valentine's Day, he probably wouldn't have been surprised when she didn't show up at his luxurious East Hampton mansion. He'd grown far too comfortable in the relationship, taking Marcela for granted, staying out all night, embarking on road trips, plane trips and train trips with his poker buddies, not telling her where he was until he’d been gone and on the road for days at a time. There was no way that she would be able to tolerate that life.
Bradley did his best to explain all of this to Cara. He’d never talked about the pain of that breakup. It was something that he tried not to think about but every year, around this time, all those bad memories came surging back, flooding his mind. He still hadn't figured out how to deal with it, but maybe, just maybe, talking, even if it was just to a stranger whom he just happened to be paying a hundred thousand dollars for 72 hours of her time, maybe talking to such a person is just what he needed. At least, that's what he hoped. As he looked into her eyes, he saw warmth and compassion that he rarely saw in his high-powered, New York friends. Everyone in his social and business circles was so cutthroat, cold and ruthless. There was something sweet and tender and naïve about this young girl that warmed his heart. She made him feel like one day, he would be able to open his heart again and take the chance of loving someone and letting someone love him.
After talking for several hours, they both dozed off to sleep. Cara was woken by the sound of her phone. Bradley had already told her that part
of the deal would require that she keep her phone off for the entire 72 hours. It was a risk that she would simply have to take.
Cara had never felt so confused in all of her life. There was no way that she could break the date off now with Bradley. Not only wouldn’t she get any of the money, she would also be hurting him in the same way that the love of his life had done. She couldn’t imagine being the cause of even more despair and loneliness for him. That would’ve been very hard to live with. But she couldn’t lie to herself that she was completely over Danny. There was no question that he still held a place in her heart and he most likely always would. Their relationship, despite or maybe because of its frequent up and downs, had left an indelible impression on her.
Maybe all she and Danny needed was a change of scenery. Life on the west coast would suit their wild and free spirits. New York was just too damn uptight for them. But after a few months, after the money ran out, they would be back to their struggling and hustling days. When those memories surge into her mind, Cara began to shake her head from side to side. She wanted out of this forever. Her desire to be done with this exploitative, degrading bullshit had to be stronger than her love for Danny. Didn’t it?
Or would she end up being one of those women who turned themselves into a martyr for a no-good man? She’d seen other women do that before, throwing away their best years only to be stamped on and kicked around.
When she walked into the hotel room, Bradley was out on the balcony smoking a cigarette. He had on his silk robe and pajamas. Cara smiled as she noticed that he seemed to have regained some of his swagger, which seemed to be very natural, over the past few hours.
While she watched him blow his smoke into the night sky, Cara couldn’t help wondering what her life would have been like if she’d ever dated a man like Bradley—wealthy, successful, and handsome and not the losers, bad boys, and addicts that she usually fell so hard for. But it wasn’t that she found Bradley to be some over sensitive wimp for a metrosexual dude. She was definitely not attracted to those. She needed a man--a real man that could sweep her up in his arms and make her feel loved and protected. That’s what she’d been wanted for so long but never seemed to be able to attain.
The sound of the patio door slamming shut startled her. She raised her head, body quivering, eyes flooded with fear. Bradley stared at her with a wicked smile playing on his lips.
"Is everything all right?" He asked, as he slowly came across the room towards her.
She crossed her arms over her chest and took a step back. For the first time in the evening, she found herself feeling slightly uncomfortable around Bradley. There was so much that they still didn’t know about each other. There was so much about this 72-hour date that made absolutely no sense to her.
"Yes, everything’s fine," she barely managed to say, as the words seemed to get stuck in her throat.
She took another step backward and kept her arms tightly crossed over her chest. Bradley stopped walking towards her and the expression on his beautifully chiseled face turned from lusty to concerned.
"I hope that I’m not moving too fast for you," he said. "But you’re the only thing that I’ve been able to think about while you were gone."
Cara wiped a lock of auburn hair behind her ear and timidly raised her eyes. Bradley took that as a cue to boldly come forward and tightly wrap his arms around her. She didn’t fight against him. It felt too right. Too damn right. This strength, this warmth, this affection was what she’d been yearning for. Now that she had it, she knew that she would never let him go.
She reciprocated his tight squeeze, wrapping her arms firmly around his muscular frame. She pulled her head back momentarily as she felt something big and hard poking her in the stomach. Her eyes, playful with mirth and lust, fixed on Bradley. Her lashes fluttered as her hand clasped around the hard cock that squirmed around under the silk robe. Through the fabric, it felt long and thick. She couldn’t wait to see just how big his cock was. Bradley leaned down and kissed her hard on the mouth. Within seconds their tongues were darting in and out, swirling up and around, each other’s hungry mouth. Bradley's hand’s roved up and down her body. Electric sparks went off from head to toe. She could feel her panties getting wet, so fucking wet. She’d waited so long to be taken forcefully, to be ravaged by an experienced man, a man who would understand the ebbs and flows of an erotic encounter.
Her hands tore at the belt to Bradley’s robe. It quickly dropped to the floor. For a few moments, all she could do was admire the beautiful specimen of masculine beauty that stood before her. Eyes wide and mouth gaped open, she let her hands graze every inch of his muscular flesh. She was mesmerized by how hard and muscular his pecs felt. Then the hands slid down to his abs. She’d seen six packs before but never as perfectly sculpted as his. Each of the hard abdominal muscles seemed to be on the verge of exploding. She’d never realized just how attractive a hard body could be. But what caught her attention more than anything else was the fat slab of cock that hung between his legs.
She picked it up, held it in front of her face, and stared at it for a few seconds with a big, mischievous grin. She was turned on by the massive dimensions but also a little bit afraid that she might not be able to take all of him inside her.
"That’s a wonderful cock," she said, planting a few soft, wet kisses on the large, purple mushroom head.
"It’s fucking huge," she said.
Bradley brushed away the comment, trying to play it as cool as possible. Despite his apparent nonchalance, he actually took a fair amount of pride in the size of his prodigious member and Cara was certainly not the first woman to shower him witty compliments while gazing at his hard cock. But no matter how many times he heard those words of praise, they never got old.
"You wanna suck on Daddy’s big dick?" Bradley said, looking down at her and taking the shaft of his cock in his big muscular hand.
Cara answered by nodding her head up and down submissively. She liked feeling that he was in control of her. She liked feeling that she could relax and trust him to take her to heights of pleasure and experience that she could have only dreamed of.
"I need to hear you, baby," Bradley said. "I need to hear you tell that you need me. Can you do that for daddy?"
"Daddy, I need your big hard cock in between my lips. And after I suck on it, I want you to stick it in your tight pussy."
Bradley’s eyes grew wide with desire. He closed his eyes as Cara took hold of his hard veiny cock and began to stroke it up and down. Her soft flesh and gentle touch moved rhythmically back and forth on the huge shaft.
"That feels so fucking good," he said, struggling to get the words out as pleasure gripped his throat.
Cara swirled her tongue around the head of his cock, then slowly began to take more and more of the shaft down her throat. She would take as much of it as she could. In her line of work she had the pleasure, or maybe it was a misfortune, to experience a wide range of penises. After two years in the business, she had begun to wonder whether or not she’d seen them all and she’d grown a bit bored and disinterested with the male member, formerly a subject of great interest. She had taken more than a few books out of the NYU library that dealt exclusively with the cultural history of the penis. The strange, sometimes imposing, sometimes delightful, sometimes grotesque male member had always fascinated. When she was first debating whether or not to get into the business, it had been her prurient interest in seeing a wide range of cocks that had finally helped her overcome her doubts and reservations.
Cara’s slurped and slopped on Bradley’s cock, her mouth overflowing with saliva, her green eyes dilated and on fire with lust. The cock felt so big and hard and full in her hands. Once she got tired of slobbering up the saliva-slicked shaft, she pushed her head down on it farther and farther and… she could feel herself gagging and she was forced to pull the cock out of her mouth. Panting and out of breath, she looked up at Bradley with a big slutty grin. It felt so good to suck so hungrily on a hot guy’s c
ock. For the last six months, since Danny had run out on her, the only dick that she had in her life came from her legions of very horny but unattractive clients.
While she sucked on his cock, she began to gently tug on his balls, giving them a nice stretch. Bradley closed his eyes and moaned. He couldn’t remember the last time that his cock had looked that full and hard. Could the last time have been that night all those many years ago? That wasn’t something that he wanted to think about at that moment. He was supposed to be doing this to purge himself of the bad memories.
Chapter 5
Cara and Bradley were laying in bed, smoking cigarettes and sipping champagne.
"But I know that you’re not really going to pay that much money," she said. "That would be completely crazy.”
Cara shook her head and smiled. From the moment that she walked into the hotel room, Cara had been waiting for Bradley to break the bad news that she wouldn’t be receiving the previously discussed fee because that was just a hoax.
"If you really don’t want the money," Bradley said, pausing to take a puff off his cigarette. "Then I don’t think I’ll have any problem finding another young whore."
Cara’s pretty face quickly filled with disdain. She narrowed her eyes and fixed them on him.
"What did you call me?" She said between clenched teeth.
Bradley recoiled slightly as the smile disappeared from his face. Before he could say anything to make up for the faux pas, Cara had gotten off her knees and headed off in the direction of the bathroom. The door slammed shut angrily.
"Fuck," Bradley said under his breath. Sensing that he might have pushed things too far by calling her a whore.
Cara paced around the bathroom, arms pulled tightly against her chest.
Sniveling and trying to hold back a torrent of tears, arms crossed tightly over her chest. She couldn’t help feeling that she had once again messed things up, letting her guard down too early and failing to restrain her hypersexual nature. Bradley hadn’t even been forcing the issue sexually. She had desperately wanted to taste his cock and couldn’t contain herself.
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