It was late. Jeanie had been out late before, but not like this. Sure, Jeanie was old enough to be out on her own, 22, but she had always called when she would be delayed and her step-father, Ted, was worried. And excited.
Jeanie had gone to the hottest club in the city, a place where the young and beautiful would hook-up, sometimes for a dance or two, sometimes for the night. She had no trouble strutting past the velvet ropes, with her natural good looks, her slender physique, her perfect, plump little butt, and her long legs. Her sky-high heels and haute couture little cocktail dresses didn't hurt, either. Ted worked very, very had, was paid very, very well, and spent a lot of money on decorations for his beautiful ward.
Years ago, Ted had married Jeanie's mother. He was looking for something different and he found it in his demanding, sexy wife, Charlotte. She had been a handful. She saw little reason to stop her vigorous sex life simply because she had taken on a more-or-less full-time sugar daddy in Ted. Ted had built her a home, dedicating a bedroom with attached bath for her use as a boudoir. It had the largest closet in the house, and Charlotte furnished it with sachet-filled drawers filled with luxurious lingerie of every conceivable sort, fantastically high heels, and the latest in fashion-designer clothes. And a special, locked cabinet filled with every manner of deviant toy -- when she needed, she always chose very carefully among her accessories and toys. And Charlotte always wore the most jaw-droppingly sexy clothes that Ted could afford. And Ted was very, very rich.
She used this arsenal to indulge her principal hobby: Charlotte slept with men and women indiscriminately and her tastes were as diverse as they were obscene. She always came home to Ted, however, who reveled vicariously in the racy stories she would tell him while she took off her makeup. She made a ritual of removing it, then letting Ted peel her sweaty stockings from her flawlessly curved thighs, calves, and sexy little feet. Ted finished by pleasing her, orally. Before they would turn in for the night, Charlotte would conclude her tale, sitting on Ted's face and stroking his rock-hard dick with the ball of one foot and the arch of the other... He would usually blow his load, moaning into the cleft of her ass while she told him about the end of her filthy adventures.
Charlotte had other interests, aside from slutting around. She also thought that her son, Gene, wasn't much of a boy. Gene had been born after a youthful indiscretion that marked her move from high-spirited heiress and ingénue into the class of full-fledged adventuress. She had married Gene's obscenely wealthy father in a shotgun wedding, the divorced him, taking him for everything he had. She quickly ran through the funds she garnered in the settlement, but she just as quickly had moved on to another source of lovely things: Ted.
But, to repeat, Gene was not much of a boy. He never played with sports equipment and he seemed inordinately interested in removing the clothes from his "boy dolls": what the manufacturers laughably called "action figures." She took it upon herself to... encourage...
certain behaviors and discourage others, beginning when he hit puberty. It wasn't difficult. Gene had always been drawn to the amazing array of beautiful, slutty, and sexy garments her whorish mother displayed in the boudoir. Once, five years ago, Charlotte caught him running his delicate little hands through her panty drawer on several occasions and she quickly hit on a plan.
"Gene darling," Charlotte said, startling the slender boy. "If you like Mummy's things so much, I could buy you some to wear." A thin smile curled one corner of her full, red mouth. Gene snatched his hand back from the drawer, a lazy wisp of a thong still tangled on his thumb. His pale skin bloomed a full red blush. Adorably, the blush went from his face, down into the tank-top he was wearing. Charlotte must have known that his whole body would be enflamed at the prospect.
"Come here, sweetie," Charlotte said, in a tone that defied disobedience. "I know you have been wearing my things... don't bother to protest. Your step-father takes a great deal of pleasure in keeping his eye on me." Charlotte took Gene's birdlike shoulders in her impeccably manicured hands and turned Gene gently in the direction of the small, rectangular alarm-monitor high in the corner of the room. "Do you know what that is?"
"The monitor for the alarm," said Gene.
"Yes, sweetie, but there is a camera in that monitor, just as there is in EVERY monitor in this house," she said. Gene paled as the significance of this statement sunk in. "Did you know that, my darling... boy?"
"N-no," Gene stammered. His rosy blush bloomed again. Charlotte was charmed by the pink flush at the base of his long (for a boy) neck. "Does that mean that Step-Father has seen... everything... Everything I've been doing?"
"Yes, sweetie," Charlotte purred into his delicate little ear, brushing it with her lipstick. She slided her hands forward into the broad sleeves of Gene's tank-top, caressing his still-hairless chest and puffy little nipples. "Step-Father has seen everything. He and I have been talking about it for weeks now." She ran her long, slim hands down his belly, then withdrew them from the tank-top.
Gene arched his back, trying to prolong the contact. He need not have worried, because her hands quickly returned to the waistband of his jersey material shorts and slid them down. He blushed again as he realized she would see his naked ass -- he had skipped underwear when dressing so he could get dressed quickly when he entered the boudoir. Charlotte smiled up at the camera, knowing Ted would be as delighted by this development as she was. She turned Gene to face her and examined his now naked-from-the waist down body. Gene's legs were long and colt-like, with graceful, curvy feet, just like his mother. He was about his mother's height and weight, too... which is part of what made Charlotte and Ted's plan so...
Like his mother, Gene seemed to have discovered the pleasures of shaving his pubes -- they were hairless and smooth, either because of shaving or because he simply wasn't that hairy naturally. Charlotte was delighted by this feature... and amused by the incongruity of a now swelling, full-sized penis between such girlish legs.
"Yes, Gene... or should I say, Jeanie," Charlotte asked, stroking Gene's lightly-fuzzed thighs and looking directly at Gene's penis, with a clinical interest. "Your Step-father and I have been talking. We've been talking about your future. Now, sweetie, we both know what a miserable failure you are as a student. You're probably distracted by all those handsome young men in your classes... aren't you," she asked, suddenly gripping Gene's penis in her long-nailed hand, her eyes flashing with... not anger exactly.
Gene reacted predictably: he flinched and the blush showed on his belly now, beneath his flimsy tank-top.
"Aren't you," Charlotte purred again, moving forward so that Gene could feel her hot breath on his throbbing penis. "Aren't you, baby," she repeated, pumping his dickie.
"Yes," Gene murmured.
"Yes, what," Charlotte asked sweetly, digging her razor-sharp nails lightly into his penis, not hard enough to break the skin.
"Yes, Mummy!"
"Yes, darling, that's right."
She quickly kissed the head of Gene's prick, leaving a smudge of lipstick, then released him.
"Now, what you might not have known is that your step-father and I have been... hmm... changing our relationship. Ted (which is what you should call him now) is getting tired of me. No, no, don't object," she said, responding to Gene's surprised look and playfully caressing his balls. "Tired may be the wrong word. Ted's a man of huge appetites and he wants a new toy. Don't worry, baby... Mummy will still have all her delicious toys and scrumptious wardrobe. Ted likes the idea of me being a super-hot cougar on the prowl. He just wants something new to spice up his life. Eventually, I may want to move on, too... which is why your real education is about to begin."
Charlotte reached up and gently pushed Gene down to his knees. "Now, baby, lesson one is that when Mummy is talking, you can always be using your mouth productively... start by kissing Mummy's toes."
Gene blushed again, wondering whether Mummy had been looking at the nasty files he kept on his laptop... of course she had. Gene removed one of her insanely expensive high-heeled sandals and sniffing her patrician toes. She moved her foot forward, toying with Gene's puffy lower lip, then moving her big toe into his soft mouth. Spreading her legs and slowly bringing her arched foot up, she led Gene closer to her fragrant crotch.
"Now, sweetie, move your mouth from my sweet little toe to my even sweeter pussy," she said as he settled his mouth on her pussy. She placed a hand on each side of his head and guided it until he was licking just the right spot. "I'm going to call you Jeanie from now on, baby: spelled J-E-A-N-I-E. I've ordered you some darling little monogrammed underthings. I know, I know -- it's a little... ooh, that's right, that's where Mummy likes it... it is a little girly... but you can buy sluttier things for yourself when you get older. Mmmmmmm"
"Now here is your next lesson," Charlotte said, pulling Jeanie's cum-smeared face up from her pussy and turning Jeanie's face so she could breath her next words directly into his/her shell-like little ear. "If you play your cards right, you'll be able to bang as many hot boys and girls... and boy-girls... as you like, and you'll never have to work a day in your sexy little life."
It was late. Ted looked at his watch again and continued to think about the last few years. They were paying off as certainly the most pleasurable investment of his life. Shortly after their intimate, boudoir conversation, things had begun to change quickly. Gone were all of Gene's boy-things. In their place, a replica of Charlotte's elaborately equipped boudoir. Jeanie's mother had hired a lady's maid and a personal trainer to build the plaything that Ted desired. Periodically, doctors, manicurists, beauticians, tattoo artists, piercing artists, and stylists would consult, but the trainer -- an imperious little bitch, named Devon, selected personally by Charlotte, taught Jeanie everything she needed to know about pleasing boys and girls, as well as the slutty etiquette lessons Jeanie would need to enjoy her life.
Jeanie learned how to flirt outrageously, how to remove her underwear in public places, how to suck a cock or lick an asshole or pussy, how to gracefully remove a pubic hair from her mouth... and so on. Jeanie learned how to accommodate huge plugs in here tight little ass, and she learned to do kegel exercises to keep her ass-pussy as tight as could be expected. Jeanie also learned how to arch her toes in the way that Ted liked best, and, using a practice dummy at first, Jeanie also learned to ride a man's face, gently pushing out a load of captured semen into a waiting mouth.
Jeanie needed practice boys to do that training. She recruited them by hanging out at the nearby colleges and universities wearing a microscopic miniskirt that barely covered her silk-covered balls, let alone her plump, thong-split ass. She would wear high, platform heels, a cropped, v-neck top with long, loose sleeves, which showed off her spectacular new artificial breasts. Around her neck was a broad, velvet choker -- not to conceal her Adam's apple, which had been shaved almost immediately after beginning her new life -- but just to highlight her beautiful neck. Her long, honey-colored hair was drawn up in two plush pigtails. She was boy-bait.
She would bring the boys home to her special room and suck their sweaty boy-cocks until they didn't care that her dangling penis was often bigger than their own. They would let their tight balls slap her large, dangling ones, while they fucked her ass-pussy. Jeanie would look up at the monitor and wink, knowing her step-father was watching her training carefully. As the young swain blew his load in her perfect ass, she would blow a kiss at the monitor, and then quickly turn around, sitting on the training model, while licking the boy's cock clean. The training model would buzz pleasantly, its latex lips sucking shit and cum out of her asshole, while she extracted another load with her mouth.
It was late. The door down the hall from Ted's room opened and he heard the click clack of high-heels fading away toward Jeanie's room. Ted reached over, finishing his drink and following the sound down the hall. When he arrived in the doorway, Jeanie was seated in a way that he remembered Jeanie's mother sitting, after a night on the town. Back straight, gazing at her disheveled face in the mirror and removing her makeup.
In a moment, Ted would be at her feet, removing her heels sucking her toes as she told him about the men and occasional women that had used her. She would tell him about the big dicks, the slick pussies, the sweaty assholes she had orally pleasured. Ted would work his way up her long, long legs, kissing the runs in her stockings as he got to the silky tops of her stockings. Then, she would smile down at him and tell him to lie down on the floor. She would slip her heels back on.
Then, Jeanie would straddle his face, letting Ted worship her nearly empty ballsack for a while, smelling her randy sweat before he began licking her perfect, dirty, slimy asshole.
"Yeah," she would murmur. "Mmmmmmm... Where was I? Oh, yes. So Derek started pumping my ass with that short, thick cock of his. I could smell his cologne as he crushed my dick and balls between our bellies. My dickie got sooo hard, Daddy. Precum lubed my silky belly while he spermed my asshole. I pulled off of him and slipped in my usual buttplug to save his treat for you, Daddy. And then, Daddy... you know what?"
Ted mumbled from between her asscheeks, sucking her anus and slurping every bit of Derek's cum (and Jeanie's messy shit) from her hot little hole.
"You know what I did next," she repeated, then, suddenly, stood, towering over Ted in her heels. She squatted back down, bringing her swinging, filthy dick to her step-father's lips. "I fucked him in the ass until he cried like a little girl. Can you taste him on my prickie? Hm? Can you? Daddy? Can you taste his shit on my dick?"
Yes, in a moment, all that would happen. In the moments before it would begin, Ted savored the moment and smiled.
"Like Mother, like Daugther, right Jeanie?"