A happy family had always been a little hard to come by in Sam’s life. The relationship between his mom, Lucy, and dad for most of his life had always been strained and despite any efforts to hide the cracks from Sam as he grew up, he’d always sort of known.
As it became harder and harder to hide the fact of it all from him, they had put less effort into trying. Nights of silence, cold and bitter were replaced more and more frequently with nights of arguing, shouting or even absence, his mother or father opting to spend the night somewhere else entirely.
They’d promised themselves, apparently, that they would stay together until he moved out, for his sake. That plan had apparently changed to when he would turn eighteen. Then, to when he turned seventeen. In reality, they had split when he had just turned just sixteen and, in a way, it had been a difficult time, though he hadn’t had to make any hard decisions about who to stay with.
The house was in his mother’s name, inherited from her grandmother years before and with his father seeking to move across the country, there had never been any debate as to where would be best for Sam and though he saw his father now and then, their relationship strained with the distance.
The first few months of his mother’s newfound single life had been one of relief and joy for her, but as time went on doubts and worries had begun to creep into her mind. Her work, as a teachers assistant in a nearby school, helped for the most part to cover the basic costs, but she struggled with debts beginning to mount, their quality of life dipping and the prospect of having to sell the family home, her home for near enough all of her life, was starting to become a looming prospect.
But things had changed for the better for Lucy when she had met Cassandra. Unlike Lucy, who was a delicate little thing like Sam, closer to five foot than six with a delicate figure and light blonde hair, Cassandra was a standout. A little over six foot and with skin like dark rich chocolate, she had appeared in their life in what had seemed like a whirlwind romance with Lucy. She had been a temp at him mothers school and, after inviting his mother out for a few drinks on her last day had, for convenience, crashed that night at theirs. But something that night had changed, between them both stumbling home drunk and Cassandra leaving the next morning, something had sparked. A couple of drinks turned into a couple of dates, a couple of dates turned into many more besides and within six months she had moved in, living with Sam and his mother, halving the bills and making things more than manageable.
It hadn’t taken Sam long to find out just what the spark between Cassandra and his mom had been. Each night, without fail, for anywhere between fifteen minutes and, on some occasions, anywhere up to a couple of hours, he was forced to put his headphones in, lest he listen to the gasps, moans, pants and groans that emanated from their bedroom, permeating the entire house with no room for misunderstanding as to what was causing them.
In the early days it had been a source of embarrassment, he would blush and play loud music, trying to drown out the symphony of sex, but now, almost a year and a half on from when it had started, if anything, he was just used to it. No longer did he cringe and hide each night, though he still lost himself to the less pervasive noise of his own music.
His mom was completely infatuated with Cassandra and, for her part, Cassandra seemed to love her too, but her actions sometimes left Sam feeling more than a little bit off guard, especially after he turned eighteen. He had wondered what it would be like, having a step mom like Cass, and while he wasn’t sure what to expect it hadn’t been the sexual nature of the woman. Always sweet towards him in front of Lucy, every now and then he would come down early in the morning, heading to the kitchen for a drink or something to eat, and he would bump into Cassandra.
That in itself wasn’t unusual, but more often than not at these chance encounters she would be stood, her butt leaning on the kitchen counter, completely nude, save for a cup of steaming coffee clasped in her hands. She would smirk then turn to leave, as if she had been stood there just waiting to be caught, letting him see her in all her glory, her legs long and lithe but powerfully built, like a long distance runner, her hips curved, her waist thin, her breasts full and soft, slightly low as she was, after all, in her late thirties. Her smile was intoxicating even when he caught her in such compromising moments, often drawing his attention away from other more pressing matters, namely, the thick chocolate cock that slept between her thighs, imposing and threatening. Before he fled those encounters or she left she had always managed a flirtatious wink and a loving, “Morning sugar,” that set his cheeks aflame.
In other ways too, he was sure, she flirted with him, friendly hugs always lasted a few moments too long, her hand often squeezing him here or there as she did, her eyes would wander over his body and even when he caught her looking, she would continue, never ashamed to be caught by him.
Her comments too while seemingly sweet and innocent to his mom left different implications with him, Cassandra often commented on how much like his mother he was, with his small build, doe-like eyes, cute blonde hair and, she would always tease with a laugh, his big white ass. Playful jokes seemingly, but coupled with everything else it made him feel… A lot of things.
Following a quaint little ceremony, she became for all intents and purposes his new step-mom and her flirtatious interest in him didn’t dwindle as he had expected, to the contrary she had taken every opportunity when Lucy wasn’t around to make Sam the centre of her attention, as if tempting him with her gorgeous body while leaving absolutely no doubt in his mind about what she wanted to do with him.
It left him feeling conflicted, he’d never had much luck with girls and at nineteen he had never been in any kind of relationship. While, for the most part, her attention made him uncomfortable, her wanting gaze was the only one he seemed to get and it made him feel warm. Her cock, in particular, was a source of unsurety, he knew he shouldn’t want it, but he found himself drawn to it, curious about it, it was after all so much bigger than his own.
Whenever she squeezed him to her body or he caught her looking in an especially lustful way he would feel his heart flutter. He enjoyed her attention, though he hated himself for it, she was much older than him, she fucked his mom on the regular and, he had to keep reminding himself, she she had a huge black cock.
He always wondered if, given the opportunity, how far she would take things with him, but for the longest time the chance never came, Lucy so enamoured with Cassandra she was never too far away from home. At least, that is, until his mom was invited to a foreign school. Her own school had received exemplary awards for quality and, as one of the more outstanding members of staff she had been invited to take part in a school exchange program, staff would, for two weeks, switch with counterparts in foreign cities to share knowledge, hopefully with the outcome of both parties coming away with an increased understanding of how to best teach their respective classes.
His mom was simply thrilled, they had seldom been on holiday and never outside of their own country to be part of a small team selected to go to Canada to impart their knowledge, a destination she had always wanted to visit but never been able to was just the best thing in the world for her, outside of Cassandra and Sam, of course. Both of whom had been incredibly supportive, but in the week or so leading up to her trip, a full two weeks away, a tension had risen between the two of them, one that his mother, in her glee had completely failed to notice.
The night before she left, as she had a very early plane to catch, she had come in to see Sam before he had fallen asleep, hugging and kissing him, the excitement plain on her face as she had told him to be good with Cassandra, to look after her and to help out around the house and not to slack just because she wasn’t here.
He had of course promised, hugging her and wishing her a great time away, though a part of him wished he was going too, though his mother kept stressing it was ‘mostly’ a work thing, not a leisure thing and, that night, he had fallen asleep to the sound of a particularly passionate night just a couple doors over.
As morning rolled around Sam yawned cutely, stretching out under his sheets as his alarm bleeped at him from beside his bed, his phone telling him it was time to get up and get ready for an especially lazy Saturday. His mom, he knew, would’ve only left a few hours ago and would probably be at the airport waiting for her flight to Canada, she would be early but she always liked to be.
Stretching out again and letting out a whine of reluctance he slipped his legs out of bed, pressing them into the cool softness of his carpet before rising to his feet, stretching and arching his back before blinking sleepily.
He reached down and gently scratched his thigh through the simple pair white boxers he wore and glanced around his room, trying to figure out what he was going to do today, probably sketch he thought, or paint if he could find inspiration. But, swallowing, he winced a little, his throat was dry and his thirst was dire.
Padding barefoot from his room he began to make his way through the too quiet house, running his fingertips through his long blonde hair, pushing it back into some semblance of order, his bright blue eyes blinking slowly, wearily.
He stepped through the living room, between the deep couch his mom and Cassandra often occupied and the smaller one-seater that was often his own, then past the TV they often watched together towards the kitchen.
He paused at the threshold, instantly feeling more alert as, to his surprise, he caught Cassandra standing there, sitting hopped up onto the edge of the bench, the newspaper splayed out beside her, a coffee steaming beside it.
He stared at her and she looked over towards him, a smirk on her lips, “Morning sugar.”
Blushing furiously he turned to go but her words caught him, making him stop short, only half turned away from her, “Ah, come on sweetie, don’t be like that.”
He looked back at her, his voice uncertain, his eyes more so, not sure where to look, “L-like what?”
“Babe, you’ve seen me naked a hundred times, still not used to it?”
He shrugged a little, glancing towards the fridge, “It’s weird…” he said softly.
“It’s comfy. Go on, grab a drink if you’re thirsty.”
He hesitated, then did so, stepping closer towards her and the fridge, opening it and pulling out a bottle of fruit juice.
She set a cup down on the counter beside him helpfully and he poured himself a glass before setting the bottle back, her smirk ever present, curious, enjoying the freedom of not having his mother to risk her for her lewd behaviour, enjoying his embarrassment.
He weakly smiled his thanks and picked up his cup, taking a step back towards the door before, again, he was stopped by her words, “So, two weeks together huh? Are you going to be this shy for the whole two weeks?” she said, a little teasing.
“Are you going to be this naked?” he asked back, not turning to look.
“Mm, maybe,” she let out a soft little sigh, tilting her head back and pushing her breasts forward, “It’s just so freeing, it feels wonderful… You really should try it sometime, it’d be nice to have that hot ass of yours on show walking around the house for two weeks.”
He blushed crimson and looked across at her, her eyes weren’t up to meet his, they were down, shamelessly staring at his ass through the confines of his boxers.
“You can’t just walk around the house naked for two weeks Cassie.” He said, turning to face her again, if only to tear her eyes away from his ass.
She looked up at him and grinned, “Oh? Can’t I sugar? I don’t see why not, I mean, you enjoy it after all.”
His eyes widened at the accusation, “N-no I don’t!”
“Sure sure…” She hopped off the bench, her full breasts bouncing slightly as she took a half step towards him, “Tell you what, I’ll put on some clothes right after I get a hug, how’s that sound hm?” She set her coffee cup down on the side and opened her arms, tilting her head, a playful expression on her face.
He bit his lip glancing aside, “Why are you being like this?”
“Like what hun?” She teased, but he looked up at her, his expression a little clouded.
“Like this! Wandering around naked in front of me all the time, flirting with me, touching me!” he said, raising his voice a little bit, which, given his usually demure attitude was quite out of character for him.
Far from impressed by his outburst, Cassandra shrugged a little, folding her arms under her breasts, boosting them up to sit fuller on her chest, “it’s for your own good darling.”
“How! How could this possibly be for my own good?” He said, a little exasperated as he looked back at her.
“Because girls like me aren’t rare, cutie. And sooner or later you’re going to go to college and looking and acting like you do? Baby, you’re going to be someone’s college girlfriend within a week… So you’ll need to know how to look after women like me.” She explained with a smirk.
“What do you mean, looking and acting like I do? I’m just another guy!” He pouted, hands on hips, not helping his cause.
She laughed a little, “Oh Sammy, baby, let’s see, how about your long hair, your wide hips, your thick ass, the tight jeans, your trimmed nails, the fact that you shave, the way you love to cook, you love to clean, you love to dance… I could go on?”
He frowned, “There’s nothing wrong with any of that! Guys can like to cook and clean and dance. And every guy shaves!”
“Every inch of their body?” She smirked.
“S-some do! It’s uncomfortable…” He said, defensively.
“Mmhm and then there’s all the shemale porn you watch.” She said casually.
“W-…Wh.. I…” He stammered and she tilted her head, his voice falling to a whisper, “H-how did you even know about that…”
She let out a soft little laugh, “Oh honey, I didn’t.”
He blushed crimson and fell silent, looking down at his feet, his arms folded a little uncomfortably over his bare stomach.
She took a step forward and slid a hand around his waist, pulling him into a gentle embrace. He didn’t unfold his arms, but he didn’t step back either as she pulled him against her, his cheek pressed to her chest, “I don’t know who you’re trying to fool sweetie, embrace your femininity, let me teach you what you want so desperately to learn…”
After a long moment he pushed himself from her, looking up at her with watery looking eyes and she smiled down at him, kind and reassuring.
“…You got your hug…” he whispered softly, before turning and leaving her with her hands on her hips, sighing softly as she watched him go, foiled again.
True to her word she dressed in simple clothing, though she didn’t see much of him. He kept to himself for the most part, locked away in his room expressing himself through his art, lost in his own thoughts as he turned over in his mind what she had said.
He had seen many, many women like Cassandra in porn but had assumed that they were rare in the real world. Thinking on her words, about them being common made him wonder about his friends and who among them might be packing.
He sighed a little and scrapped the picture he was working on, crumpling it up and throwing it into the corner narrowly missing his bin, letting it settle among several other failed attempts. His expression of self today was thrown off by not knowing who he wanted to be.
After a few minutes staring at a blank canvas waiting to be drawn on he pushed himself back from his desk and stood, stepping towards his door and hesitating, looking at himself in a narrow full-length mirror he kept in the corner.
He ran his fingers through his long blonde locks, exhaling softly as he did, a frown pulling at his full lips. He trailed his fingers down the outside of the shirt, following the lines of his body, his narrow torso, slender waist, wide hips and found himself smiling ever so softly.
Slowly his hands traced back over the skin-tight denim fabric of his jeans, his fingers sinking briefly into the plushness of his ass.
“Oh, who am I kidding…” He asked his reflection softly. The idea of being a ‘girlfriend’ to a woman like Cassandra in college gave him real pause for thought, not the nightmare he thought it would be but some kind of secret heaven for him. He shook his head a little, unable to meet his own gaze knowing the person who looked back was who he wanted to be, someone he was too afraid to reach out and take a hold of. Atleast as he was.
After a moments reflection he sighed softly and stepped from his room, padding barefoot downstairs, heading for the kitchen.
He passed Cassandra, who was sat on the couch watching TV, in silence, not acknowledging her as he stepped into the kitchen, opening the fridge and poking about cupboards, seeing what was in.
After a few minutes he poked his head back through to the living room, meeting Cassandra’s gaze for a few awkward moments before he spoke, “Want something to eat?”
She smiled, “Yeah, sure sweetie. What’re you making?”
“I could do Italian? Pasta?” He said, smiling a little too, taking comfort in the routineness of their conversation.
“Sounds good. Need a hand?”
He shook his head, “It’s okay. I’ve got this. Would you like a drink while I’m up?” he asked as he turned and stepped back into the kitchen.
“Eh, yeah, sure, please.” She replied, her gaze on the swell of his ass as he returned into the kitchen before she looked back to the TV, enjoying her show and trying to give Sam a little space, not wanting to risk pushing him away again.
After a couple of minutes he returned and offered her a glass, with some surprise she took the glass of red wine, eying it and eying him with a curious smile, “Trying to get me drunk?”
He shrugged a little, almost coyly she thought, “It pairs well with what I’m making.”
She shrugged too and smiled, “I’m not complaining,” she settled back with her glass of wine and took her sip, typically she preferred whiskey or gin, but she wasn’t against a glass of red wine, though she had expected something soft from him.
Humming softly Sam began to prepare and cook, making a homemade sauce to go with penne they had in the cupboard. It was incredibly relaxing for him, able to let his mind drift as his hands worked.
He tasted what he was making often, seasoning with a variety of different herbs and ingredients to balance it out perfectly, the scents and aromas floating through the house, drawing Cassandra’s interest as his cooking always did.
“Mm, that smells delicious Sammy, what kind of sauce are you making?” She called through, her glass half empty in her hand as she reclined comfortably on the couch, running her hands through her dark hair.
“A bolognese,” he called back, “Need a refill?”
She eyed her glass for a moment then shrugged, “Couldn’t hurt.”
He came through with the bottle that she noted was missing more than one glass’s worth than wine and he proceeded to top up her wine.
“You had a glass too?” She asked, eying him curiously.
“Might have another.” He smiled a little coy and turned to leave again, going back to his kitchen as she sat, an eyebrow raised in thought, she wasn’t exactly going to stop him from lowering his inhibitions after all.
After a little while Cassandra found herself looking towards the kitchen as much as towards the TV, the gentle musical humming of Sam and the scents coming from the kitchen enticing her hunger more than the TV could hold her interest.
After a few more minutes and unable to help herself she stood, carrying her glass as she sauntered through towards the source of her mounting interest.
She leaned against the doorway with a smile, twirling a lock of her hair between two fingers as she watched him plate up, noting the empty glass of wine next to a now empty bottle.
“All ready?” she asked, smiling as she sipped from her glass, stepping forward to look at the delicious looking meal being plated up.
“Mmhm, help yourself.” He replied, looking up at her with those beautiful eyes of his.
“I thought the wine was to be paired with the food?” She asked with a smirk, tracing a finger down the empty bottle.
He eyed it and her then shrugged innocently, “I’ll open a new one then, shall I?”
“Sure.” She smirked, “Just bring it through hm?”
She smiled and stepped forward, reaching out for a plate and taking it. The meal was amazing, he was a truly talented cook and everything he made she enjoyed. They ate together, watching the TV and once she was finished he collected her plate, washing up before returning to the couch, pouring out two glasses of wine.
She took it and smiled as he sat beside her, tucking his legs up under himself, just like his mom would.
They sat in relative quiet for a while, simply relaxing in front of the TV in each others company until they had each, at last, finished their wine. At four glasses each, even with the full meal, Cassandra was feeling the alcohols buzz.
Sam collected the glasses and bottle stepping away, placing them in the kitchen before returning, sitting beside Cassandra, albeit much closer this time.
She looked at him with a playful smirk as he bunched up next to her, but he simply blushed and looked away towards the TV. With no other option, she raised her arm and slid it around his waist, watching as he tucked in close to her, his head resting against the swell of her chest through her top, his legs tucked up under him, the two of them cuddling exactly like she often would with his mom.
After a little while, as they relaxed, her hand gently caressing the skin of his arm, he worked up the courage to speak, nestling a little closer into her embrace, “Did… You mean what you said earlier?”
“What about?” She asked while giving him a little squeeze, something he seemed to respond positively to.
“Women like you… Not being rare…”
She shrugged a little, “We really ain’t, I don’t know the numbers but one in every eight? Every ten? Something like that.”
He paused, not saying anything for a few moments.
“It won’t seem like that to you, though,” She continued.
“No?”
“No.”
“Why not?” He pressed, looking up at her with his doe-like eyes.
She glanced down, meeting his blue eyes, a glint in her own, “Because girls like me? We’re predators. And honey you’re just the sweetest gazelle. I bet all your friends are girls huh?”
He was quiet and she knew she was right.
“Any reason you haven’t had a girlfriend yet?”
“I just… Never thought I’d be able to treat them right. They want a man, someone who can look after them, be strong for them, you know, all that.” He sighed softly.
Cassandra laughed a little, drawing a little bit of an ireful look from him, “Aw Sammy, I’d put good money on most if not all of them packing heat. I bet they all want to be strong for you, to look after you,” she hesitated, “…To fuck you.”
He blushed and looked away and mumbled something softly.
Cassandra tilted her head, leaning a little closer, “What was that?”
“Mfm mm..”
“I can’t hear you, honey.”
“…Teach me.” He said, his cheeks crimson.
She smirked a little and placed a hand on his warm cheek, turning him to face her.
“I’m sorry, what was that?”
“I… I want you to teach me. I don’t want to feel like this anymore. I want to be me. Whoever that is,” he said, his voice quavering with emotion as he bared himself to her, pressing his cheek to her chest.
“Alright. I’ll teach you.”
He smiled shyly, so beautiful, so much like his mother and she thought about all the things he’d need to learn, about how to act and behave, how to walk and talk, how to use his skills to please his women. But as she looked at him with his delicate and familiar features, his gorgeous long hair, the slight haze in her mind from the wine mirrored in his own look, she knew, the less animalistic lessons would have to wait for tomorrow.
“Starting tomorrow, I’m going to teach you how to be a proper little lover for a woman like me.” She assured him, but he bit his lip a little.
“What about tonight? Is it too late to start today?” He asked, having already taken the first step it was hard not to want to take a second.
“Nah, tonight I’m going to see if you sound like your mom does.”
He opened his mouth to query that, but she took his hand, pressing it into a growing bulge at her jeans, soft and hot under the denim fabric, his fingers closing around it almost on instinct, his eyes going wide.
“Y-you mean-”
He was cut short as she pressed her dark lips to his own, small and sweet, forcing him back to lay on the couch as she scrambled on top of him, his whines and squeaks of protest drowned out by her mouth and tongue as she eagerly kissed him, letting go all the pent of desire she’d held onto for him for so long now.
Sam fell back, feeling the soft cushions of the couch under him and the soft plushness of her breasts atop, his hands moving to her waist as her own pinned his shoulders, his eyes closed, his cheeks flushed as he felt her tongue press between his lips, filling his mouth with the unique sensation of being frenched.
He squirmed against her, feeling her tongue swirl eagerly around his own, exploring his small mouth, but after a few moments she pulled her much fuller lips back, his eyes fluttering open to stare into her luscious brown gaze.
“If I put something into your mouth, you suck it.” She said, her voice breathless but firm, he simply nodded meekly in response.
In a moment she was upon him again, his eyes rolling back as he felt her strong hands glide up his smooth stomach and chest under his shirt, squeezing at his flat chest and small pink nipples as her tongue once more pressed its way between his now much more willing lips.
A quick learner, he sucked on her tongue as she made out with him, grinding her cock against him through the increasingly tight confines of her jeans.
Breaking the kiss for a moment, letting her plush lips press against the pale skin of his cheek and jaw she whispered in a needy voice, “Take my cock out, stroke it.”
He gasped and arched his back as her lips worked lower, biting and sucking at his neck, his hands finding a way between the two of them, small nimble fingers perfectly suited for the task of finding and working the zip of her jeans, his small hand slipping inside and around the thin fabric of her underwear.
She groaned and kissed over his neck as she felt his soft warm fingers brush against and wrap around her meaty python and she felt a shiver run up her spine as he pulled it free.
In a swift motion she had sat up, her ass moving up so she was sitting on his chest, her cock, free from her jeans and rock hard bobbed above his face and, as he opened his eyes, he got his first look at her ebony monster.
With his hands still wrapped around it he gave it a couple of experimental strokes, completely caught off guard by its sheer size and the deep ebony colour, slightly darker than the rest of her skin, admiring each ridge each vein, the way it pulsed and throbbed in his hand.
“Well?” she said, smugly, knowing how impressive her size was.
“C-Cassandra… It’s huge.” He said, breathlessly, his cheeks maintaining their bright hue, his eyes practically sparkling in wonder.
She smirked and rocked her hips forward, pressing the length of her cock up into his face, making him all but moan in a sudden impending desire for more of her.
“Yeah it is…” She took it in her own hands, brushing his aside and angled it, pressing the lightly coloured tip of her black cock against his pouted lips, his eyes going wide as he realised her intentions, “Remember your first lesson, baby?”
He did. He let his jaw drop, then had to force it wide as she pressed her hips forward, a moan escaping her lips as she felt her cock sink into the wet heat of his small mouth.
“Oh honey that’s so good, come on, give me what I want, treat me right, yeah…”
Spurred on by her words his desire rose, he started to suck on the thick cock head that was now making its home in his mouth and he soon felt himself pressing his tongue against it out of curiosity, wanting to experience it and learn everything he could.
To his surprise he wasn’t as hard as he thought, while overall the length was hard and steely, the outside was soft and silky, the tip of her cock could be depressed by his tongue as he poked at it and swirled it around, the skin on the tip of her cock the softest he had ever felt.
“Mm, fuck, I knew you’d like it, you little slut, gods that feels so good.” Cassandra moaned, reaching up to lift her shirt up over her head, casting it aside. Her figure wasn’t as tight as it had once been, her stomach with a bit of softness to it, but she was on the whole still confident in herself, though her breasts were less firm than she once had enjoyed, so for now at least she kept her bra on, the fullness of her breasts well displayed in the half cup underwear.
“Yeah use your tongue more…” she urged, working her hips slowly forward and back, making her wide tip drag across his tongue and caved in cheeks, each time she did so her crown briefly breaking the seal of his lips, drawing a lewd sucking noise out of him, to her glee.
To her glee he complied and she felt him doing his absolute best to pleasure her thick cock, his tongue working in an amateur but still wonderful way around her tip and length whenever she pressed deeper in, her hands moved to her jeans, undoing the button to relieve some of the tightness still present around her cock, letting the jeans and her underwear move a few inches down her thighs, just enough room for her to free her heavy smooth nuts which she cupped and squeezed, loving how they felt.
Before long she had her lips parted, moans escaping with each breath as she looked down at the boy, at Sam, hardly able to see him for the likeness of his mother. She could only imagine him as a younger version of her, skin smoother, body more supple and lithe, lacking curves above his waist maybe, but his body new and inexperienced, ready for her and, for the next two weeks at least, hers alone.
Even as his jaw grew sore, his eyes looking up at her half-lidded, clearly displaying the lust he felt, he felt nothing but a growing desire for her and what she meant for him. She might have been his stepmom, his mother’s lover and life partner, but to him here and now she represented everything he could be, everything he wanted to be. His chance and first step.
He moved his hands up and Cassandra gasped in surprise as she felt his hands slide under the cups of her bra to freely hold and support her soft breasts, his fingers seeking out and squeezing her hard dark nipples, playing with them, teasing them, enhancing her pleasure as she fucked his pretty little mouth.
“Oooh fuck honey, you’re going to be such a good fucking girlfriend to women like me,” she grinned, “all fucking women like me, aah fuck, suck it, yeah just like that, mm, you’re going to be such a good little slut for so many girls.”
She reached around behind her and quickly undid the clasp to her bra, shrugging it off her shoulders and casting it aside where it landed half on the table. She then reached up and gripped his hands in hers, holding them tight to the fullness of her breasts, letting the soft flesh press against and between his fingers.
Panting hard she felt her pleasure rise, the boy was just too cute, so slutty and eager to please her black cock, so quickly corrupted, she loved it, “F-fuck, Sammy, baby, you’re gonna make me cum, do you want that huh? Ah, ah do you want to taste my hot fucking cum?”
He couldn’t respond, but he didn’t need to, the way he continued to worship the thick tip and steely length of her cock was all the confirmation that she needed to know he was hungry to taste her seed.
Eagerly she pumped her hips forward and back, loving how his soft pink lips looked stretched around her cock, his hands still kneading her breasts as she felt her balls tighten, the pleasure overwhelming as she began to cum.
“A-ah fuck! Sammy yesss!” she cried out, head tilted back, hips pushed forward as far as she could, the boy making a series of wet choking noises, his cheeks flushed as her cock poured cum into his mouth and throat, forcing him to swallow it.
Gasping and whimpering she worked her hips forward and back, spending her load deep in her new toys mouth, pulling back only after the first few pulses far enough to spend the rest of her heavy load onto his tongue.
Sam moaned out as he felt the thick hot liquid spill in rope onto his tongue, the taste wasn’t anything to write home about, but the sensations that came with it, the knowledge that he’d made her cum, that she’d used him for pleasure made him squirm in delight as he swallowed.
After a few long moments, her breath heavy and laboured, she leaned back, leaving just the tip of her slowly softening cock in his mouth, panting hard as she looked down at him both of them satisfied, but expectant.
“Oh… Oh my gods…” she laughed a little, biting her lip as she drew her tip out of his pursed lips, a soft pop sounding out as she moved up, resting her thick semi-hard cock across his face, pressing her balls to his mouth with he obligingly kept open, tongue working over the smooth sack, weighing and tasting each heavy nut, “You’re such a good little slut aren’t you? Fuck.”
Sam blushed as he sucked and kissed her chocolate nuts, as if thanking them for the gift they’d given him, “Mmfm…”
“Yeah I know sweety, you wanted me to fuck you and christen your new ass-pussy,” she smirked and reached down, stroking a hand through his lovely hair, his hands gliding down her body to rest on her hips, her breasts rising and falling with her breathes, no longer supported by his hands, “Don’t worry, we’ll fuck when we go to bed, my bed, our bed, you sleep with me now.”
With another muffled moan he nodded cutely, knowing his fate and looking forward to every single second of it.
Cassandra had promised him everything he wanted and, over the next two weeks, she more than delivered.
While he maintained his masculinity to a point, refusing her offer of becoming a woman like her, she’d certainly done a number on him.
That first night, still on cloud nine after sucking his first ever cock she had guided him upstairs, bent him over and pounded a new life into him, though her size and his inexperience had been an issue getting started, as the nights went by she taught him everything she could, training him to take her cock to the hilt, making him practice on her cock until his gag reflex was gone, teaching him every position, every hint and sign that a girl was interested in him, how to walk, act talk and flirt, even setting him a small workout routine focusing on his bubbly ass.
His wardrobe had changed, albeit subtly, the jeans tighter and more form-fitting, the shirts too clinging a little tighter to his body. Cassandra taught him that he was beautiful and had a body worth showing off, especially if he was trying to attract girls like him.
And that in itself, had worked. While he’d toyed with the idea of his friends, now able to more easily identify which of the girls were packing heat they’d all felt too close to him, too much like friends to take that leap to the next step like he had initially planned.
He’d been getting nervous, wondering if, when his mom got back, the flow of sex would cease, but, when he had been out with Cassandra at the mall getting his nails manicured the woman who had been doing his, a woman with short black hair and delicate Asian features had slipped him her number, asking him out on a date.
He’d gone out with her, Jin she was called and that night she had ended up back at his and he had shown her everything he had learned.
Cassandra had sat downstairs, a wide grin on her face as she watched TV, realising for the first time just how much the house carried the sounds of a hard, desperate fucking and she knew she’d be seeing a lot of this Jin. She’d be back every night to experience what she’d help create.
Though, listening to them, she realised they’d be competing for volume. A competition she was quite looking forward to.