Lupe

Jeff Feinstein begins establishing a harem to enjoy in his very early retirement, circa 2014. Yes, title character is based on who you'd guess.

Jeff Feinstein stood on the balcony of the Captain’s cabin of his new yacht, watching the approaching helicopter. Standing in a Hawaiian shirt, white slacks, and brown dress shoes, his brown eyes, partially obscured by his gold rimmed aviator sunglasses, followed the chopper as it circled the 250-odd foot vessel, giving his new arrival an areal view intended to impress.

Jeff himself was not especially physically impressive. In his early 40’s, his dark brown hair and goatee had an occasional grey hair here and there. His 6’1” body was lean, toned, strong but not heavily muscled. His face was handsome but he was no Brad Pitt. Everything about him physically was a bit above average, attractive enough to catch the interest of women, but not turn their heads.

He went inside when he heard the helicopter begin powering down. He had about an hour before his guest was brought to him. There was not much to prepare, and no need to hurry. Everything and everyone on this boat either belonged to him or worked for him, those in the latter category extremely well paid and interested in maintaining their employer’s goodwill.

It was good to be the king, Jeff mused.

He set a few items, including a small digital video camera and his phone, on the table next to his chair on the balcony. On the bar inside he set a tall glass and then carefully crushed two pills, brushing the pieces into the glass. They would ass a subtle taste to a beverage, but not so much as to rouse suspicion in someone drinking an unfamiliar brand of soda. A few other items needed to be set out, and then Jeff waited, drinking his favorite rum, smoking a Cohiba from Havana.

When the knock came, Jeff was ready, both in terms of preparation and mindset. “Enter”, he commanded.

Jeff’s eyes and voice were the only things about him that were extraordinary. Both conveyed complete self-assurance and a confidence that his commands would be followed, one way or another.
The first to enter was Suzy, his assistant who had been employed by him in various capacities for more than a decade. She was the quintessential MILF, in her mid-30’s, blonde and blue eyes, with the body of a porn star, and at present all of it was natural, although he had promised that he would pay for plastic surgery when needed.

The second was almost the polar opposite. Lupe was an under-sized 14 year old with the body of a girl who had grown up no stranger to hunger. Her hair was a lustrous black, hanging to her ass when not up in twin pigtails as it was now, held in place with two pink bows. Her face was adorable, with big eyes that had a haunting innocence. Her skin was a deep bronze, reflecting her Colombian roots, and shone with expensive body oil, or cream, or whatever it was women rubbed themselves with to get that glow. Jeff did not concern himself with such things. Her 4’8” figure was 28A-22-30. If she weighed 90 pounds Jeff would have been shocked.

Jeff had, in a way, watched Lupe grow up. Her mother was a prostitute named Carmen, and for 9 years he had made Carmen one of his regular fucks when visiting Bogota on business. Since he hired his whores for the night, pillow talk was normal between rounds of sex, and eventually Carmen had shown him pictures of the girl.

Thirty minutes before the helicopter had approached the yacht, Carmen had exchanged her daughter for a briefcase of money, passing her to Suzy and then being driven away by two men from the drug and human trafficking cartel that had arranged the sale. Carmen had no idea that the actual buyer of her daughter was her long time client.

Just as Jeff had no idea that, at that very moment, Carmen was bleeding out, her throat slit by the cartel members. They had decided to take the money for themselves, and had taken their time raping Carmen before murdering her. Karma is a bitch, though. Two years later they would have no idea that it was Jeff who had paid the cartel to kill them. Slowly.

Lupe was dressed in an outfit that was at once cute and adorable, and slutty. Her top was white lace, with one button to hold two flaps to cover her breasts, and sleeves down her arms, leaving her belly bare. She wore a short pink skirt that barely covered her pussy and ass. Jeff knew there was nothing beneath that skirt, including hair. White knee socks and black patent leather shoes completed the outfit.

“Sir, I have Lupe for you”, Suzy said by way of introduction. With that, she turned and left, softly closing the door behind her.

Lupe stood there, bashful, nervous. The daughter of a whore, she had no illusions about why she was there, why a man would buy her.

Jeff looked her over for a long minute, thinking. She would be the first of what would be a small harem of girls like her. It was important that she accept, even embrace, her new life so that she would then be a role model for those who would soon follow. That was the reason she had been selected to be first.

Lupe had grown up accepting the concept of a woman treating her body as a commodity, it was what had allowed her mother to put food on the table. Growing up poor would mean that a life as a pampered pet for a rich man would seem like a dream come true. Watching her mother trade he for cash would make her desperate for acceptance and validation of her worth. Growing up without a father would likely have created an emptiness that a strong male authority figure could fill.

“Would you like something to drink?”, he asked suddenly. It was not really a question. Turning, he took a
can of Coke from the refrigerator behind the bar and opened it, slowly pouring it into the prepared glass. The motion of the soda as well as its acidity quickly dissolved the powder on the bottom.

Handing her the glass, he said “Let’s talk out on the balcony”. He turned and walked outside, and the girl obediently followed. Jeff sat down in his chair, a cocktail made a few minutes before waiting for him along with his half-smoked cigar. Pointing to a reclining deck chair facing him, he told her to have a seat. She did so, crossing her legs to keep her bare sex covered.

“So, Lupe. I feel like I already know you. I have been a customer of your mother’s for a long time.” The girl’s eyes widened at that revelation. “You know what she is. Tell me.”

The girl cringed. It was one thing to know, another to say to a stranger. Finally, she answered in a soft voice, “A…puta. A whore.”

Jeff smiled and nodded. “Yes, and an excellent whore she is. She sold you to me. You’re old enough to know why I would buy you. Tell me.”

The girl took a long sip of the pop. “To be your puta.”

Again Jeff nodded with a grin. “That’s right. But you should not be ashamed. Your mother was a puta. Suzy was a puta before she was your age. For the right price, all women are whores. Besides”, he added, “better to be a whore for a rich man than for some pimp.”

Looking at him, the girl nodded. Unbeknownst to her owner, she had always dreamed of being one of the girls in the background of the rap videos she liked so much. Living a life of luxury where it is a party all the time, never worrying about where the next meal would come from. Despite her young age, she knew what the men in those videos would have expected in return.

“In fact, girl, I think I will name you Puta.” His stared at her, and despite the lenses obscuring his eyes, she could feel the weight of his gaze. “Say it. Tell me your new name.”

Lupe looked at him, appearing on the verge of tears. She drained the last of her drink, surprised it was all gone. Imagining yourself as a whore was one thing, naming yourself one quite another. Finally, setting the glass down, she whispered, “My name is Puta.”

With a victorious smile, Jeff leaned back in his chair. He spent the next few minutes telling Puta about her new life. The yacht was just the start. In a couple weeks they would be at his private island. She would have her own suite of rooms. Servants would wait on her, and she would live a life she could only have dreamed about.

As he spoke, he could see the girl visibly relax. The narcotic was kicking in. He paid close attention, and she seemed to be breathing more quickly, her face appearing to go from nervous or frightened to hesitantly excited. That could be either drug.

“You’re a pretty girl, Puta. I want to see more of you. Unbutton your top, let me so your breasts.”

This sudden change in direction took the girl by surprise. A flicker or fear returned, followed by resignation. Slowly she reached her right hand up, undoing the single button that kept her top together. She let the two flaps fall open, her hand between her small breasts, as if wanting to cover them but knowing she could not.

“Beautiful, Puta”, Jeff said, and they were, if you liked small tits, which Jeff did. The skin was perfect, the nipples dark and small and quickly became erect in the cool breeze, or, perhaps, from the pills. The fact that she did not know she had been drugged would cause her to believe that her arousal was natural. That she wanted what was happening.

“Now, pull your skirt up around your waist and open your legs for me.”

Despite this being an even more invasive command, Puta responded with less hesitation this time. Her hands slid to her thighs, fingers hooking the hem of her skirt. She uncrossed her legs, spreading her knees a bit. Lifting her butt off the chair, she hiked the skirt up, revealing the perfect tan slit of her pussy.

He stared at her hungrily. She was perfect. He could get sex anywhere, from women who could make the Pope cum. But this appealed far more to him. Yes, he liked her youth and fragility, but the anticipation of corrupting her made him more horny than a dozen professionals.

“I know you have started masturbating”, Jeff said, causing the girl to blush. “Your mother told me she caught you, the last time I fucked her.” The girl’s blush grew deeper, both from the reference to his use of her mother’s body, and that her mother’s betrayal had begun even earlier than a few hours ago. She had told a stranger that she touched herself.

“Close your eyes, Puta. Pretend you are back home in your bed. Play with yourself for me. Just like you did there.”

Puta froze for several seconds, shame and embarrassment battling with the rising effects of the Flibanersin in her drink along with a naturally submissive nature. The cool breeze made her nipples ache pleasantly, and was beginning to have the same effect on her pussy. Slowly, on hand lowered, and she closed her eyes.

She had clearly been practicing, as her fingers knew exactly what to do. She rubbed her clit, then dipped one finger inside herself, slipping it back out coated with her juices, using it for lubrication. Her legs spread wider, and she began to alternate circling her clit with fingering herself. Meanwhile, her other hand was busy massaging her breasts, stroking and gently pinching her nipples.

Jeff took a moment to ensure the video camera was aimed for maximum effect, then leaned back to watch. He remained silent, only the sound of ice cubes in his glass clinking together interrupting the show. His right hand was in his lap, idly rubbing his cock through his short.

The girl did not take long to reach her climax, causing Jeff to wonder if it was the pill or, hopefully, if she was one of those girls who orgasmed easily. One second her breathing was coming in short panting gasps, the next her thighs clenched down on her hand and a high-pitched whine of delight escaped her lips. Soon, she relaxed, her legs splaying apart, her upper thighs and pussy gleaming wetly.

“That was good, Puta”, Jeff observed, “but you can do better. Again, but this time keep your eyes open and look at me. When you cum, I want the entire ship to hear you.”

Puta’s eyes widened, but she was more than willing to comply at this point. Her young body was eager for more, and her fingers resumed their work. She stared at her owner, and deliberately began putting on a show. She fingered herself, then brought the finger to her lips and sucked it clean. Her fingers moved faster, and she began using two small fingers inside pussy.

Her second orgasm took longer, and was much stronger. It began with her hips bucking, her back arching, and deep gasps of pleasure. She cried out, maybe not loud enough for everyone to hear but certainly everyone outdoors, and her cry was followed by a long drawn out moan of ecstasy, her eyes rolling up in her head.

When she came down from her high, she saw her master had moved. He was standing, and there was a cushion on the ground in front of him. His cock strained his shorts, and he pointed at the cushion.

Puta knew what was expected, and slowly obeyed. She had kissed a couple of boys. One had even fondled her and she had rubbed his cock through his pants. But other than seeing it on the internet, she had no experience of what to do.

When she was on her knees, Jeff stroked her cheek gently, then told her to take out his cock. She fumbled with his belt, then unzipped him, pulling his shorts down. She let out a little gasp. While Jeff was a little bigger than average, his cock was not huge. Still, it was larger than what Puta had felt through that boy’s pants. Much larger.

“Stroke it”, he cooed down to her. This would be the hardest part for Jeff, not turning having her suck him off into him raping her mouth. The girl reached out one of her small hands and wrapped her soft fingers around his steely shaft. “Good girl. Give it a kiss.”

Slowly, taking his time to enjoy the physical and visual sensations, he coached the girl on giving her first blowjob. His voice was soft as he directed the action, which was being caught on the video camera. Licking and kissing his cock. Cupping and stroking his balls. Keeping her eyes on his. Finally, taking him into her mouth.

He groaned loudly as he warm wet mouth stretched around the head of his cock. He smiled down at her as she began to bob her head back and forth, her twin pigtails flicking with each stroke. Without encouragement, she took more and more, until she gagged and pulled back with a gasp.

Jeff caressed her cheek and slid his hand to the back of her head. “You’re doing so well, my Puta. Try not to pull off when you choke. It feels so good when you do.”

Entranced, he watched as she began to suck on his cock with growing enthusiasm. He encouraged her, telling her she was doing well. It was a bit awkward when he said, “you’re as good a cocksucker as your mother”, but after a pause she seemed to take it as a challenge, to surpass her mother’s fellatio skills.

What she lacked for in skill she made up in eagerness and sheer loveliness. His cock disappearing into her angelic face, her eyes watering, drool seeping out of her lips and onto her beautiful little tits drove Jeff wild. She did not need to be told twice to use one hand on herself, and it did not take long before she was moaning her third orgasm out around his cock.

That pushed Jeff to the edge, and he pulled out. He told her to look up at him and use both hands on his cock. As she stroked him to his own climax, her beautiful, slutty face stared up at him. She knew what was coming and she braced herself for it, determined not to look away.

The first shot took her by surprise, hitting her forehead and oozing down around her left eyebrow. Her eyes and mouth flew open in shock, and the second landed as a thick white rope from her left eyebrow over the eye and onto her cheek, fouling her eyelash. She closed her eyes tight, feeling line after line painting her face, one large glob landing in her right eye, another shooting into her mouth causing her to retch.

All the while her owner looked down, growling in ecstasy, as he covered her teenaged face with his jizz, defiling her, marking her as his. When he was done, he shoved his cock back into her open mouth, ordering her to suck out every last drop. She started to reach her hands to her face to wipe the mess off, to at least clear her eyes, but he grabbed them and held them away, telling her to put them behind her back. He reached over, taking his camera to get a few good shots of her with his cock in her mouth and of her face drenched in filth.

She deserved a reward, he decided. Stooping, he grabbed her under her armpits and lifted her bodily into the air. She squealed, and he carried her inside, murmuring compliments, calling her his good little slut and the like. With her eyes plastered shut, she could not argue the point.

He laid her on her back on the bed, growling at her to leave her face alone. Spreading her legs, he knelt next to the bed. Jeff rarely ate pussy, seldom interested in the pleasure of his partners, but the girl had earned it.

Besides, he had plans for more.

Never had Puta felt such incredible pleasure. Her owner’s mouth, tongue, and fingers seemed to be everywhere at once. One finger slid delicately inside her, reaching for a spot she had no idea exited. In barely two minutes her hips were bucking in Jeff’s face as she came again, smearing cunt juices across his face as he continued to eat her.

Jeff continued through and after her orgasm. He wanted her on the edge, and when he got her there, he stopped. She whimpered in disappointment, but in a moment her whimper changed tone as Jeff began to push his cock against the entrance to her cunt. It was slick and ready, but she was tight, both from her size and from her lack of experience. But Jeff was relentless, forcing his cock past the tight entrance and then slowly, inch by inch as she whimpered and moan in pain and pleasure, he buried himself inside her tight hole.

Jeff paused for only a moment, adjusting her hips and his position, then began to slowly fuck her. One hand reached down, his thumb rubbing her clit, as his other lightly grabbed her throat, pinning her in place. Her right eye was still plastered shut, but her left was open, blinking rapidly in an attempt to clear the stinging cum that had seeped in. She was a mess, a glorious obscene mess.

And then she came yet again, for the fifth and final time for the morning. Her fourteen-year-old pussy clenched down on the cock filling it, and a scream of pleasure broke from her. He fucked her harder as she squirmed beneath him, enjoying every second of it.

When she was done, he flipped her onto her hands and knees. He made sure she was facing a large mirror on the wall, and then got behind her. The goo in her right eyes oozed down her cheek, allowing her to get it open, her eye burning, just as he entered her from behind. She got to watch herself as her master took her like a dog, and he got to watch her face as he fucked her.

She was lost in sensation, the afterglow of her orgasm, his cock sliding forcefully in and out, slowly building her towards an orgasm she was not sure she could survive. She barely reacted when he began to massage her anus with his thumb, did not notice the lube her was smearing around her tight little sphincter. She moaned in protest when he pulled out of her pussy, and did not have time to consider what was happening when his cock pressed against her asshole.

She screamed in earnest when Jeff forced it inside, splitting her open. He watched her in the mirror, loving every second of her face twisting in agony, her cries singing to his sadistic soul. He reached around to once again rub her pussy. Slowly her cries became whimpers, shame mixed with the receding pain as he used her ass like the whore she had become.

She did not suffer long. Jeff was too far gone, and his thrusts, painfully slamming into her bowels, were erratic. He stopped playing with her pussy, grabbing her hair and pulling her back, forcing her to watch as he violated her ass. Then he came. With a loud grunt, his balls emptied, pumping his load into her rectum as he stopped, buried to the hilt in her hole.

When he was done, he collapsed, pulling her into his arms. They lay there, his cock softening inside her before slipping out wetly. Her ass was on fire, her eyes stung, but she remained in his embrace. The drugs were wearing off, although she did not know that. But despite that, she felt oddly at peace. She was a whore, but a rich man’s whore. The experience had been equal parts painful, both emotionally and physically, and intensely pleasurable. His arms around her seemed to promise protection and warmth, while the opulence of his cabin promised a life of ease.

It seemed a fair trade.

His breathing had slowed, his breath warm on her cheek as he held her. She slipped out of his arms and climbed quietly out of bed, heading to the restroom.

She had finished using the toilet and cleaning her face when he entered. Without a word he took her hand and led her into the shower. It was built for two, with a pair of rainfall shower heads on the ceiling, a paid of long flexible hoses, and a series of jets from the walls, all of which could be adjusted. Jeff turned the water on, and stepped in, pulling her behind him.

The water was warm, on the verge of being too hot. Puta closed her eyes and let it wash over her. His fingers worked through her hair, making sure it was thoroughly wet before he gently pushed her out from under the overhead waterfall.

He washed her hair first, using a fragrant shampoo, his fingers working it into her long tresses before using the showerhead to rinse it completely. Then her body, his fingers touching hers softly, rubbing liquid soap over every inch of her. His touch when he reached her breast, ass, and between her legs was not overtly sexual, but the sensual setting caused her to be aroused nonetheless. When he was done, she was clean from head to toe.

She was not the only one aroused, she noted. His cock was almost completely hard, sticking out proudly from his body. Jeff gave no order, but Puta knew what she should do. She dropped gently to her knees and took him into her mouth.

The blowjob was sensual, the girl offering her mouth for his pleasure and her master receiving it as his due. He did not hold back, allowing her to finish him before her jaw became sore. When he came, he held her head on his cock, the tip on her tongue inside her mouth. She choked, unable to swallow quickly enough, but he did not complain, and the water quickly rinsed the bits that drooled from her lips away.

Finished, he toweled her off with incredibly soft Turkish cotton towels before drying himself. A red bikini, gauzy white wrap, white and red hat, and big red sunglasses were waiting for her on his bed when they stepped out of the bathroom, and she gave a happy squeal, rushing to put them on. She knew enough about fashion to know that this one ensemble probably cost more than her entire wardrobe at home.

The afternoon was spent on deck, where a pool and a hot tub were nestled next to a bar. Jeff and Suzy sunned themselves in chairs, and Puta went back and forth between playing in the pool and sitting with them, asking questions. The fact that a pair of Filipino serving girls were on hand to bring her suntan lotion, drinks, snacks, whatever she wanted, excited her. Suzy showed her how to use voice commands to play music from speakers around the deck. Sometimes between her accent and the limitations of voice recognition the results were unexpected, but for the most part she got to play disk jockey.

It was midafternoon when Jeff called her over to him. It only took a glance at his crotch to know what he wanted. She pulled down his swim trunks and sucked him while she played with herself, pulling her swimsuit to the side. When her pussy was nice and wet she mounted him, riding his cock with her petite body. After a moment, Suzy got behind her, reaching around to caress her small breasts and then one hand slipped down to play with her clit.

Jeff just leaned back, watching his partner in crime fondle the girl, whispering into her ear loud enough for him to hear. Suzy, who had first taken money for sex at the age of twelve, had been a whore for a quarter century, the last six of it exclusively for Jeff. She knew how to make him crazy with lust while getting herself off, and she imparted that wisdom to her young protégé. Soon, Puta was rocking and bouncing in his lap, impaling herself on his cock, moaning, talking dirty to him. She came just in time to drive him over the edge, cock cock shooting his cum into her tight spasming cunt.

Under Suzy’s direction, Puta climbed off her master, getting back on her knees and sucking him clean of his mess and hers. Then it was time to pay for her lesson.

Suzy lay on her own chair, and Puta got between her legs. Puta had never dreamed of eating pussy, but she followed Suzy’s tutelage, knowing that her new life required new experiences. She lapped at her mistress’s pussy and clit, using her fingers as directed. Her hand was small and Suzy was nowhere near as tight as the young girl, and with a little work she managed to push her entire fist into the woman’s cunt.

After her orgasm, Suzy returned the favor. She did not do it as Jeff had, intent on bring the girl off quickly and efficiently. Instead, she dragged it out, working the girl into a frenzy, then backing off. Not until Puta was reduced to begging was she given release, squealing as she came on her mistress’s face.
When she had recovered, Suzy playfully asked, “So, Puta, who does that better, me, or your master?”

The girl giggled. “You do, Mistress. But Master does it faster.” They all laughed at that. Puta was clearly a pleaser.

Suzy whispered into the girl’s ear. With another giggle, she asked, “Master, may I call you Papi instead?”
Jeff raised an eyebrow. “If you’d like, Puta.”

His first acquisition was a big success, Jeff thought to himself.