"Those challenges will take no longer than five days, today included. By the time we're due to return to shore, you'll have ended your obligation to me for the money."
"I understand," Anna confirmed. The thought of being bound to follow his commands in some strange challenge excited her. "Just tell me what the first challenge is," she said expectantly. "I'll do whatever you say, sir."
Phillips stopped in the walkway and twisted around to address Anna more directly. He looked into her eyes softly.
"Do you remember the man who helped you on board?"
"What?... Um, yes." She nodded apprehensively. Ahead, on the sunlit deck, she could see several crew members milling about. The afternoon sun scorched the deck, and their features were hard to discern. Looking out to them, and then back to Phillips, she asked, "Why?"
"His name is Rico but he's generally known on here as 'The Wolf.' Great member of the crew. Strong, vivacious... loyal."
"What about him?" Anna inquired.
"You like your men in control, don't you. I saw how you looked at him. Believe me, I pay attention to these things."
"Yes... I do," she confessed. "It's not just that, though. He paid me attention, and it made me feel good."
"And it turned you on, didn't it?" he asked rhetorically.
"Yes."
"I want you to have sex with him."
"What?!" The demand surprised her.
"Your first challenge is to let him have you, whatever his desires may be, in the privacy of your cabin."
"I've seen him once!" she said, exasperated. Still, the thought of the challenge from Phillips stimulated her, and got her adrenaline going. Actually hearing the request still caught her off-guard, though.
"Do you feel that this order is unfair, Anna?" Phillips asked, genuinely curious.
"It's a little sudden... but no, it's not unfair," she admitted. Anna thought about the sculpted, work-toned chest of the deckhand. She pictured his strong, sun-tanned arms and chest and his broad frame towering over her.
"So, if I were to call this man, you could comply and submit to him?" Phillips asked with gratification in his voice.
Anna didn't answer. She prepared herself mentally for the challenge she knew she would accept.
"Two million dollars, Anna," he repeated to her, leaning in. "More importantly," he added, waving his finger like a school instructor, "a test of loyalty. Can you take my orders? That is what I would like to find out. If I get some enjoyment from seeing your progress, so much the better."
Anna, hands on her hips, thought through his proposal. She undressed Rico in her mind. "They call this guy The Wolf?! ...I don't know how crazy he'll be in bed. But would it be so bad?" she asked herself, her mind racing to weigh her options. She had been with many partners in her time, and had tried a lot of different things. She enjoyed sex immensely and felt reasonably experienced.
She turned to face him squarely and pressed a finger down on her lips. "You're sure this is how you want to test me?" she asked seductively, already knowing his answer.
"Of course. My employees do not negotiate with me. My mind is settled on it. To change it now would go against the spirit of the proposal and the very purpose of this challenge."
"If I agree, what are the... limits?" she asked with a coy voice. She rocked and twisted her hips, anxious to get started. "I mean, when he's... with me."
"There are none. Anything goes. You are to serve him and his needs."
"Whatever they may be."
"Yes, Anna."
"I hope he's gentle. He's a big man."
"Yes, he is. I cannot promise or even suggest to you that he will be gentle or that his tastes are pedestrian. But, Anna, I promise you that you will suffer no... lasting harm."
Anna could feel herself getting wet at the talk of this. She looked down toward the crewmen again. They were laughing and rough-housing, enjoying their work break.
"Let's do it, then," she said determinedly. "Bring him to me."
"Good girl. I'm very pleased that you've made this decision," Phillips replied, walking back a bit and holding his chin thoughtfully with the thumb and index finger of his right hand.
"I want to see him now," Anna snapped back at him lustily. "I want to show you that you can be in control." Anna looked passionately at Phillips. "I want to show you that I like it."
"Yes, that's good. That's very good," he replied, before turning away. "Rico!" Phillips shouted down the corridor to the exposed deck beyond.
The sounds out on deck ceased. Footsteps could be heard moving closer from on the deck, then a figure appeared in the doorway.
"Yes, boss?" Rico asked with a thick accent, leaning his head into the shaded corridor.
Phillips pointed to Anna.
"Yes, boss," Rico acknowledged, upbeat.
"He's been told already," Phillips confided to Anna.
"I'm going to show you," she responded, as the crewman approached. Anna stared at Phillips. "I'm going to serve his needs, and I'm even going to enjoy it," she said to him defiantly.
"To be truthful, I didn't know what to expect from you," Phillips said, crossing his arms. "Your confidence pleases me. I'm not going to watch what he'll do to you, Anna, but I will listen in on you and see how you handle yourself."
Rico reached them and, taking one of Anna's hands in his own, led her back down the walkway toward the cabins without a word.
Phillips, at a leisurely pace, made his way to the cabins as well.
4.
The door to Anna's cabin closed shut behind her. Rico, The Wolf, stood at the door. As before, he was bare-chested. His broad shoulders and bulging pectorals were covered in a multitude of coarse, black hairs which trailed off the further down his torso they went.
Rico twisted the lock closed and turned around with a purposeful, expectant look. Anna faced him from the foot of the bed.
"Look, I heard you were nicknamed th-" her voice trailed off. Rico, ignoring her smalltalk, had unbuckled his trousers and dropped them to the floor. Stark naked from head to toe, his massive cock curved lazily down, awesome in its size even when flaccid. His eyes, staring at hers, were vacant and without emotion.
"Jesus Christ," Anna whispered involuntarily. Taking in the sight of his impressive physique, her tongue pressed hard against the back of her front teeth. Desiring what she saw, a dull ache came from the back of her throat.
Not one for conversation, Rico reached her in two strides and, quite roughly, spun her around. His arms and hands went to work, and the thin sun dress was off in an instant, exposing her underwear.
"Give me a minute, I can-" Anna explained to him without effect. Rico's hands were already at work at dragging her panties down her legs to the floor.
Anna breathed more shallowly, thrilled at the passion behind his forceful behavior. Helping him out, she adjusted her legs to assist him sliding down her panties. That being done, Rico reached up and simply ripped apart the back of her bra with his formidable seaman's hands.
"Hey!" she cried in mock protest, getting more and more excited at his abrupt, hungry behavior. "Please be gentle, I'm delicate," she lied in tone that told even the non-native English speaker that she was not being honest.
Rico answered by flinging the broken bra without concern onto the floor of the cabin. He grabbed her by the waist, cupping the flanks of her back with his palms. She could feel the course skin of his hands, toughened and strengthened from years of maritime labor against her smooth, soft skin. Rico, having taken her measure, pushed Anna forward with a great heave so that she landed face down on the bed.
Anna thought to roll over onto her back, but Rico, already upon her, restrained her with powerful hands.
"No. Stay on the bed like before," he told her in muddled English.
"What are you going to do to me?" Anna asked in a sultry voice, bending her head around so that she could speak out to him and not to the mattress.
"The boss says I can do anything to pretty lady, yes?" Rico inqu
ired.
"Yes," she admitted eagerly. He couldn't see her, but Anna had a filthy smile on her face. "You can do anything you want to me."
A rough palm slapped hard, very hard, against her bare ass. Anna didn't respond, though she knew it would leave a red mark. Suddenly, though, she felt a finger probing and wiggling its way, carefully but resolutely, into her asshole.
She moaned, squirming against the sensation. Instinctively, Anna tried to get up and away from him, but Rico, lurching to intervene, held her down with his weight.
"Just to get you ready for me," he explained, not at all apologetically, as he carried on with it. "You give me your ass. I start by being gentle. To open you up for me."
"Do what you want."
"Not a problem?" he asked, checking to make sure.
"Not a problem," she replied. "Just know that I've never done... that before." Anna continued to squirm as her body grew used to the feeling of him in her.
"This is okay, yes?" Rico asked as he continued to loosen her. "Take boss's test, yes?"
"... Yes," Anna said with a slight moan in her voice. She embraced the challenge and accepted Rico's needs. She had to prove Phillips wrong. What Rico was about to do to her took her outside of her comfort zone, but she knew she could do it. Fearful excitement flowed through her and the anticipation of what was to come.
"Okay," he responded. "It is too big to go ahead from the start. I have to get you ready, yes?"
"Yes." She pictured his large cock. She had no view of it, but she could feel it pressing against her, warm and hard, as Rico sat on the bed next to her.
"Okay," he replied, again using one of his favorite words. His finger worked its way down and around, flexing and stretching.
"Ah!" Anna exclaimed as he manipulated her a bit more forcefully. The adrenaline flowed through her again.
"You are almost ready."
"Don't you have some lubricant?" she asked softly.
"No."
"Oil? Lotion? You must have something."
"No. You are almost ready. It will be good, yes?"
"Please, go slowly."
"No. Boss says I get anything from you," Rico replied, shaking his head. He remembered the rules and so did she. "Do not be afraid, you will be ready. I will make you enjoy it."
Anna moaned again as she took a jerk from the finger, which worked more confidently now. She began to feel a pleasurable burning from his activity. Then, just as quickly as he had started, Rico took his finger out of her.
"Okay," came the same accented voice from up above.
Anna braced herself. Before anything happened, she heard him spit. Immediately, she felt something wet hit her flesh and trickle down into her. His finger, returning, pressed back inside of her and worked the spit around.
"Okay!" strong arms pulled her midsection up into the air, setting her carefully into place as you would a piece of furniture. Anna felt herself getting more wet. She couldn't remember the last time a lover had manhandled her and taken control this way.
"I want you to fuck me," she whispered up to him. Fluid dripped down from her pussy onto her legs.
"Where do you want me to fuck you?"
"I want you to fuck my ass. Give me that cock," she commanded. She had never slept with such a stranger before, and the thrill of this had worked her up into a frenzy.
Strong, tanned feet planted themselves, one after the other, to either side of her as Rico squatted down above her. The mattress bounced about as he got himself into the proper position. Rico spat again, this time onto the palm of one of his hands, before rubbing it up slowly up and down the length of his cock. Satisfied with the moist shine that this produced, he dipped himself down into her.
Anna's mind was ready, but her body resisted him. She cringed and pinched the bedsheets with her hands as he stubbornly broke through into her with the broad, smooth head of his penis. There didn't seem to be any way it could fit, and her muscles struggled to contain it.
"I want you to break into me," she said, groaning.
Sensing that she was losing ground to him, Anna could feel every millimeter as it slowly worked its way inside. Her body eventually gave way. Once his head made it fully inside, Rico pushed downward forcefully and rapidly with a bouncing stroke, using his body weight. His cock tore its way down into her.
Neck muscles straining, she raised her head directly up and screamed out a raspy shout from the bottom of her lungs. The entire ship must have heard her.
The cock tested Anna's limits. At the best of times, it would have proved formidable. Here, with her inexperience, she struggled with her own body to accept it. She could feel its warmth burning her. Deep down, beneath the strain, she felt a twisted pleasure as it plowed its way inside of her.
Rico, lost in his own pleasures, paid her no attention. His colossal penis, with tiny, measured thrusts up and down, continued to fight its way inside. Anna, eager to submit but unable to cope with his immensity, clenched her muscles against the ongoing intrusion.
"Open for it," Rico instructed from above. "Accept it."
"It hurts," she said, no sound of complaint in her voice. "Uh!" she squeaked. "It's just so big. Can you... can you slow down?"
"It gets better," he replied, not answering her as he continued to struggle his way further inside. "Open for it! Relax it for me, yes?" he said with upwards inflections.
Anna's abdominal muscles strained themselves as her body resisted the advancement. Rico responded by drawing back out and then slithering back in more slowly. He probed down to where he had reached, her ass closing tightly around his impressive girth. She moaned hoarsely. Up above, he groaned in delight like a wild beast.
"Good?" he asked, grabbing together a bunch of her hair in his left hand.
"Okay," she forced herself to reply in a guttural tone, using one of his words. The intensity of his lovemaking pushed Anna to the limit, despite her excitement. "It's so big... Oh God!" she exclaimed as a thrust sent chills of sinful pleasure shooting up her frame. She shivered.
"Good," he said, continuing to beat his way down into her. His left arm, clinging tightly to her hair, yanked her head back in a rhythm which matched his thrusts down below.
"I'll beat your challenges," she cried out with closed eyes, not to Rico but to the thought of Phillips, who she pictured doubting her ability to submit to him. She could not accept that.
"Yes. Take the challenge," Rico replied, continuing to drill her mercilessly. He had by now managed to open his way far down into her.
Paradoxically, the further Rico went, the more Anna found herself beginning to relax.
The initial jolts of pain had eased. Though still testing Anna's endurance, the act became more and more enjoyable.
"Fuck me!" she cried.
Rico let go of Anna's hair. Both hands closed down around the flanks of her lower waist. Groaning in pleasure, he had found rock bottom. Withdrawing slowly, and then thrusting downward once again, he sank himself deep inside of her. Anna felt herself bloated to the limit, her insides fighting against the volume he had placed inside of her body. The rapid pulse and warmth from the massive cock produced a euphoric sensation that radiated outward into her.
"Good?"
"Yeah!" she blurted out with crude enthusiasm. Anna had never been dominated so wildly by any lover, let alone a stranger. The recklessness of this encounter ignited dormant passions.
Rico pulled out entirely. He let himself dangle above her for a moment, ominously. Then, squatting back down slightly, he allowed the tip of his penis to play with her, teasing itself around the opening. Her pussy dripped.
"Come back inside," Anna commanded from below, intent on seizing some control from him. Rico immediately complied. She felt herself part open for him as he slid back down.
The sensation this time was world's apart from three minutes earlier. Bought with the initial wave of pain, this new feeling was one of fearful delight. Her adrenaline continued to flow.
It was just as well.
Rico's cock slammed down against her more rapidly than before. She couldn't tell whether she had just grown numb or had simply been broken in, but to her surprise it felt good. Really good. Anna could now also feel Rico's balls lapping against her backside as the length of his penis pushed in to its very end.
Not interested in any back and forth conversation with her, Rico continued to groan lecherously as he worked away, dipping down again and again into her. Hearing him please himself made her even more aroused.
Anna kept her posture in a position to let him in easily. Her hands, no longer clenched on the bedsheets, relaxed as she took him in. She stayed still and accepted it, moaning faintly as his cock pleasured her.
So self-absorbed, he couldn't last forever, she knew. "Maybe he'll finish with me soon," she thought.
He did finish thrusting, but not as she had expected. Withdrawing from her, he pushed down on her back with his rough hands as he helped himself stand up on the bed.
"You wait," he said to her as he stepped down off of the bed. She did as she was told, and waited. She bounced in place as his weight transferred off of the mattress.
Anna heard Rico reach down for something. Before she could figure out what he had reached for, Rico ordered, "Come here."
Rolling over gingerly, she felt her muscles recover themselves. She swung around so that she could sit on the edge of the bed. Tired from being stuck in such a demanding position, she was more concerned with being able to walk. He had opened her up, and she already felt a powerful throb pulsing through her.
"Come here," he ordered again, in the same monotone but forceful voice as before.
Anna stood up. In his hands, Rico had her teal sun dress, scrunched up.
"Give me your hands," he commanded.
She held her arms out toward him. Without offering an explanation, Rico laced the dress around her wrists, which he pulled together. The thin, forgiving fabric provided good material for the tight knot he fastened.
Pleasure Boat (The Billionaire's Demands #1) Page 2
