Chapter 4: Tracy’s Mom
Tracy had the biggest crush on Tyler, and she was pretty sure he felt the same way about her. Tyler was a bit short at only 5’6″, but he had that slim young teen heartthrob vibe, and that just made him seem even cuter to the slightly shorter, petite Tracy. Both were eighteen, lived in the same subdivision, and had just finished their senior year in high school, but while Tracy had been crushing on him since she was a freshman, it was only in the past month or so that Tyler had started finding more and more excuses to come over to her house, to Tracy’s giddy delight.
It had all started when Tyler had begun mowing lawns in their neighborhood earlier that spring for some extra cash. The normally shy Tracy had convinced herself to slip into a one-piece bathing suit and set up shop on a reclining chair on her back patio, ostensibly to tan, from which she pointedly feigned a cool indifference toward the object of her affections as his shiny, sinewy body walked back and forth across her lawn, growing ever closer to her bare arms and legs with each pass.
He didn’t seem to take much notice of her, to Tracy’s chagrin, and to make matters worse her mother had appeared, fresh out of the shower and wearing nothing but a towel. Tracy wanted to crawl into a hole and die as her practically naked mother unfairly criticized her beloved’s hard work before turning a sly look on Tracy herself, fully aware of what Tracy was doing since she’d never tanned a day in her life, before dragging her embarrassingly voluptuous curves back into the dimly lit house like some sort of monstrous cave-troll.
Afterward, however, Tracy’s fortunes seemed to have reversed completely, and whether out of sympathy with Tracy or just out of having finally been made aware of her presence in the first place, she was excited to realize that Tyler was now taking frequent brief glances up toward the house, craning his neck in what had to be an attempt to see her body better. So, Tracy arched her back a bit and stretched her arms over her head to reward him, shocked at her own uncharacteristic forwardness, but finally bathing in the addictive attention of her beau.
Apparently Tyler had liked what he’d seen, and over the next few months Tracy’s yard was treated to twice as many mowings as any other house in the neighborhood, and Tyler kept finding excuses to come over and do other odd jobs around the house as well, even at reduced wages when Tracy’s mom complained about how much she was paying him. Even worse, her mom always found an opportunity to come out and criticize his work, and frequently did so wearing the tight, low-cut tops and heavy makeup she had taken to wearing recently, meaning that Tracy had to watch Tyler be constantly subjected to an embarrassing amount of her mom’s curvy, mature body.
Tracy’s dad had walked out on them a few years before, and though the divorce settlement had left them with a comfortable few million to live off in addition to her mom’s own modest income, Tracy’s mom’s unrealistically high standard of living meant that their finances had slowly dwindled. As a result, the brazenness of her mom’s fashion choices had grown as well, to the point where her constant desperate attempts to seduce handsome young tech millionaires into being her new sugar daddy meant that each time Tyler came over she was inadvertently showing him more and more of her large freckled breasts and thick, surprisingly toned thighs and hips encased in skin-tight leggings.
Still, Tyler never complained to Tracy about her mom’s embarrassing lack of modesty, and Tracy was flattered by the lengths her crush was willing to go through to see her, so she always made sure she was in her lawn chair wearing her one piece when he came over, so that the experience would be worth putting up with her mom.
Tracy knew he wasn’t interested in the money, of course. He was interested in her. And so she impulsively decided one day that she would find some of the Perfect Girlfriend Juice she’d heard about on the internet so that she could properly reward all of his efforts. She knew that it would change her, that it would irrevocably transform her into Tyler’s Perfect Girlfriend, whatever that happened to be, but that’s what she wanted to happen. Her beloved Tyler deserved no less than perfection, and Tracy was determined to make sure that he got it.
It had been surprisingly easy to find, and a few days later she was holding her small, cylindrical aluminum guarantee that she and Tyler would be perfect for each other forever.
And so, when Tyler texted to ask if he could come over to hang by the pool Tracy took his request as solid evidence that he finally intended to make a move, and this was even further confirmed when he asked if her mom had gotten back from her business trip yet. Clearly Tyler wanted the two of them to be alone together, and Tracy was more than ready to make it happen. She told him that her mom was back, but that the pool was still pretty secluded by the bushes in her backyard, and so he should definitely come over anyway. And, in a further stroke of luck, her mom had left to go shopping as soon as Tracy had hung up, guaranteeing that they’d have the whole afternoon to themselves.
Tracy wanted to make an impression on Tyler when she joined him by the pool, and wanted to up the ante from the one-pieces she’d been wearing, but she didn’t have any bikinis of her own. So, she borrowed one of her mom’s instead even though it was much too large for her, tightening the straps as much as possible even though it still left most of her small B-cups almost completely visible inside the giant cups that usually held her mom’s enormous double Ds.
Finally ready, she popped open the Perfect Girlfriend Juice and took a moment to enjoy the anticipation of her looming transformation before chugging as much of the tangy, mildly carbonated sports drink as she could.
Immediately she began to feel a bit strange as a new, unexpectedly powerful yearning began to grow within her. Oh good, it’s taking effect, she reflected dreamily to herself as her thoughts began to turn toward just how yummy boys were. She tried to keep her mind focused on Tyler out of the ardor and purity of her love for him, but almost immediately her thin veneer of adolescent fascination was washed away by a much deeper, primal need to be in the presence of a man, any man. Tyler would do fine, of course, since his masculine words and whims were just as capable of molding and directing the raw sexual potential building up inside her as any other male of her species, but Tracy knew that if she happened to see another guy before she made her way to Tyler, she wouldn’t be able to resist turning herself into their devoted Perfect Girlfriend instead.
Any metaphorical parallels between the capricious nature of her schoolgirl crush on Tyler and the ease with which she had been convinced to forget about him entirely were lost on Tracy, but it was too late anyway, and she had no choice but to go along with the Juice’s compulsions, growing more and more desperate to find a man to bind herself to and discover the answer to the question suddenly burning within her.
Soon, Tracy couldn’t help but go in search of what she needed, counting herself lucky that Tyler was likely already out back, not because she cared which guy turned her into a sex-obsessed, walking wet dream at this point, of course, but because he was likely the closest person who could.
She found him sitting by the pool, as expected, talking on his phone. She quietly snuck up behind him, her characteristic timid nature yet unchanged even as she was irresistibly drawn to his presence under the influence of the Juice.
“Yeah, I’m over at Tracy’s again… What? No, Tracy’s nice and all, but I definitely don’t like her. I’m here for her mom, man. Have you seen her? Such a milf.”
Her mom? Something about that didn’t seem right, and a feeling of unease began to filter through her haze of Juice-induced desire and curiosity, even as Tracy’s thoughts greedily latched onto the idea that her mom might be Tyler’s Perfect Girlfriend and her body eagerly prepared itself to grow and swell and mature.
Still, she couldn’t help but feel a bit miffed nonetheless. Tyler was supposed to be coming over because he liked her, not the curvy, unabashed sexuality of her milfy mom! If Tracy had known, she never would have drunk that stupid Perfect Girlfriend Juice in the first place! But Tyler was talking again, and Tracy couldn’t help but focus all of her concentration on his words, hoping that he’d drop another hint about what sort of woman he’d want to fuck so that she’d have no choice but to become exactly that sort of woman.
“I mean, I wouldn’t turn Tracy down, even if she’s a bit quiet and petite and stuff, but her mom’s just so much hotter! Like, have you seen those tits?? I was over here cutting grass like a month ago and she came out with just a towel on! Ever since, I’m over here every chance I get, man, and you know you would be too! And she’s definitely a total slut. I can tell she likes me from the way she stares, and she keeps wearing skimpier stuff when I’m around, showing her body off to me and all…
“Of course I’d fuck her! I’m telling you man, if her tits were bigger, and if she were even sluttier and had a thing for younger guys, she’d literally be the perfect woman! … What? No, I wouldn’t mind dating an older woman – that just means more experience! I could just let her take charge, show me a thing or two…”
All the while Tracy was hiding in the bushes, drinking in his words as the Juice successfully persuaded her own mind and body to reflect them. Of course Tyler wanted to fuck her mom. What red-blooded male wouldn’t? Suddenly the thought of being just like her mother, but even bustier and sluttier, seemed like the hottest thing in the world to Tracy. She knew that she should be absolutely horrified at how appealing that idea was becoming to her, but that knowledge paled in comparison to how much the Juice was making her want it, and so Tracy began to change.
Her mom had always been tall at almost 6 feet, and as Tracy’s head began to press into the limbs of the bushes above her, she joyfully realized that she was about to share that same trait, if not exceed it. Her hips began to widen to replicate the mature thickness her mother’s figure had taken on after her own birth, before surpassing it entirely as her thighs simultaneously swelled with toned muscle along with a healthy amount of nice, soft, jiggly fat. Tracy had always liked her petite frame, but all it had taken to change that fact was a few throwaway sentences from her former crush, and now she was incredibly eager to experience her mom’s voluptuous mommy curves being inflicted on her own body.
She felt her chest finally beginning to deform and distend inside the empty cups of her mother’s bikini top, swelling out from the small, perky young Bs riding high on her chest to heavy mommy milkers even larger than her own mother’s. They looked as she might expect her mom’s to look if she’d gotten herself knocked up again and pumped out a couple more kids, sagging a bit from their sheer size and weight but so full and soft and swollen that they retained their protruding rounded shape nonetheless, capped with large, dark areolas and nipples thick like Rollos. Tracy knew that they were perfect for letting Tyler know just how much of a mature and experienced milf she was, while also evoking the mental image of the massive pornstar tits she knew he had in mind when talking about how much bigger he wished her mom’s tits were. She could feel herself becoming a busty cougar out of Tyler’s wildest wet dreams, and she couldn’t wait to use her mature new body to make his dick all big and hard for her.
At this thought Tracy felt her arousal beginning to spiral out of control, her body filling with ravenous sexual need as her pussy swelled up fatter and fatter, knowing that Tyler’s words were currently turning her into a giant slut but welcoming her new complete lack of inhibitions nonetheless. God she needed a cock pounding her soft, sloppy pussy right now, especially if that cock belonged to a virile young stud like Tyler. It once again briefly occurred to her how disgusted she should be that she’d been turned into a pornographic version of her own mother against her will, but the truth was that Tracy had never felt so happy in her life. Or so horny.
Time to put this body to work, Mommy Tracy thought hungrily to herself, and stepped her towering, curvaceous body out of the bushes, surprised at how natural the extra weight packed into the now-tiny bikini felt hanging off her jiggly frame. She had absentmindedly loosened the straps as she had swelled, loving the feeling of her body filling it and conforming to its ever-shrinking constraints, until her mother’s significantly smaller cup size did more to reveal Tracy’s own obscene curves than hide them.
“Oh shit dude, I think she’s here! I gotta go!” she heard Tyler hiss into the phone before hanging up and whipping his head around.
“Hi, I’m, um, Trina, Tracy’s mom’s older sister!” Tracy fibbed, knowing how bad the impromptu lie had to sound even as she came up with it. Her mom didn’t even have a sister, for one thing, but Tracy’s overwhelming sexual desire for Tyler had severely restricted her mental bandwidth. “I’ve heard so much about you!” she gushed, sinking on to the lawn chair beside him and pulling him over into a tight hug. She let the astonished young man sink against her curves and rest his face on the naked skin of her soft, jiggly right breast, still poorly encased in the bikini top she knew she’d be shedding minutes later. She held him there for far too long, pressing him into her massive cleavage as she gently stroked his hair, giving him the milf treatment she knew he’d dreamed about.
“My sister Amy told me what a handsome young man you were, but I wasn’t expecting you to be this handsome,” Tracy purred flirtily when she finally released him, squeezing his arm and looking him up and down as though she’d never seen him before. “If I were a few years younger, well, I might be tempted to let you take advantage of me!”
“That’s, um, very nice of you, Mrs….” Tyler stammered as his bravado from seconds before crumbled at being confronted with exactly what he’d said he wanted. Tracy’s mom’s sister was somehow even hotter than Tracy’s mom, and as he tried and failed to avoid staring at the massive mound of flesh pressing against his entire upper arm he felt his dick beginning to stir inside his swim trunks.
“It’s Ms.,” Tracy said, giving him a knowing wink as she squeezed her massive, new-yet-oddly-familiar tits together between her forearms, relishing the hungry look on Tyler’s face even as his cheeks began to burn with self-conscious embarrassment. “I’m still looking for my Prince Charming. Someone who could really appreciate all that I have to… offer.” She squirmed in her own overpowering arousal as his eyes traveling up and down her curvy form at what her words implied. It was funny – Tracy could remember thinking that her mom’s voluptuous figure was gross and old less than an hour ago, but now, being even more obscenely curvy herself and knowing that this was exactly what Tyler wanted, she couldn’t help but think that there couldn’t possibly be a sexier body type in the world.
“Say, Tyler,” she continued, seizing the moment offered by his roaming eyes and pumping hormones to risk being a bit more direct. All of her shyness seemed to have evaporated alongside her youth and inexperience, and now that what she and Tyler both wanted was within her grasp, she was more than willing to seize the opportunity. “I’ve heard of young men having crushes on older women,” she said as she gently placed a hand on his thigh and began to lightly stroke. “Have you ever experienced anything like that, Tyler?”
He gulped and nodded, his eyes still not having made it up past her chest ever since her hug had enveloped him in her enormous breasts. Tracy glanced down and saw the bulge growing a few inches away from where her hand was stroking. God she loved watching young men get turned on by her body like this. They were so hormonal, their bodies wanted sex so badly, and Tracy loved how easy it was to turn them on and and make them give her what she wanted.
“Do you think I’m pretty, Tyler?” Tracy purred at the same instant that she allowed her finger to gently brush against his shaft for the first time, watching his eyes widen in surprise and lust as his cock throbbed against her. He nodded again.
“That’s good.” She used her free hand to reach behind her back and unclasp her bikini as she continued rhythmically brushing her fingers against his twitching cock, her actions instinctual and irresistible due to the Perfect Girlfriend Juice still running hot through her veins. “I just feel so comfortable around you for some reason, Tyler, like I could just completely open myself up to you.” She punctuated this statement by opening her thick thighs a bit wider, and was rewarded with his glance dropping momentarily to her crotch as his dick pulsed once again in her hand.
“I think we should get to know each other a bit better.” She finally allowed her bikini straps to fall down her shoulders, fully revealing her chest to him. “I think you’ll find that I have nothing to hide.”
Tyler stared slack-jawed as her mommy milkers suddenly bounced out into the open in all their glory. Tracy hefted them for him, pinching and rolling her thick nipples between her finger and thumb to make them all hard and puffy before offering them to the delighted young man.
“It’s fine, you can touch them. I know you want to.”
Tyler instinctively reached to do just that, before his upbringing and the reality of the situation came crashing down on him, and he pulled his hand back in uncertainty.
“Mrs… um, are you sure we should be doing this?” he asked, but Tracy impatiently swung a long leg over his torso and straddled him in answer, putting her swollen, heavy tits right in his face for him to play with. Tyler immediately forgot his reservations and began reflexively hefting and stroking them, enjoying how surprisingly soft yet weighty and solid they felt in his hands, like large bags of sand. They felt even better than he’d dreamed they would.
Tracy loved how gentle and tentative he was being, how nervous he was about what he was doing even as his teen hormones drove him to touch and caress her hypersexual body. She found it endlessly amusing knowing that within fifteen minutes she’d have him gripping and squeezing and slobbering and sucking on her veiny hooters like his life depended on it.
Even so, she briefly glanced around nonetheless, glad that though they were in the middle of the backyard, none of the neighbors could see in. Thank goodness for fences, and for her mom going shopping! Tracy could feel Tyler’s hard dick pressing against her labia through their thin swimsuits, nestling into the gap of the puffy, swollen cameltoe the Juice had given her early-middle-aged body. She began to slowly rub herself against him while he was distracted with her chest, enjoying feeling him intermittently twitch against her pussy as the sensations of her gentle dry-humping ran through his sensitive dick.
“We can stop if you want to. Do you want to stop, Tyler?” she asked, briefly slowing her pace even further in what almost seemed like a threat. He vehemently shook his head, though his greedy mouth never left her thick nipple in the process. Tracy grinned and resumed rubbing her sex against his.
She loved how much larger and older she was than Tyler, how her body fully covered his smaller frame, how she was already threatening to bury him in soft flesh before she had even begun enveloping his dick. She felt powerful, she felt wanted, and even though she could sense Tyler’s own unrecognized power in the insistent need of the masculinity throbbing against her receptive entrance, she derived endless satisfaction from the knowledge that she was the one in control, able to engulf and direct and release that masculinity according to her own whims.
Tracy felt that it was time to make that metaphor reality, so she reached underneath herself and pulled his swim trunks down, taking the opportunity to pull her thong aside to give him access as she did so, and was rewarded with the silky softness of her fat, swollen vulva and loose labia sliding directly against the skin of his cock for the first time. Tracy wasn’t sure of how tight milfs’ pussies were supposed to be, but she knew that hers was as slick and juicy and welcoming as Tyler could ever want, perfect to effortlessly sink himself into, to make his hard cock all nice and deliciously slick as he stroked himself to completion against her soft fleshy walls.
She seemed to have been correct in her assessment, and grinned in satisfaction as the suction of his mouth against her swollen teat increased and he gave a deep, throaty moan. Meanwhile Tracy continued to slowly and seductively grind against him, feeling her loose folds gently caressing and wrapping seductively around his cock, knowing just how much he was enjoying the new sensations now that nothing separated his dick from her pussy.
Mommy Tracy wanted his first time to be memorable, of course, and she continued her pussyjob, sliding herself against him with less and less friction each time as the copious lubrication from her gushing pussy coated him and readied him for penetration. With each pass, she slid a bit further up his body and leaned a bit further forward, both to bring her clit into contact with his shaft as well as to open herself for him, pressing her tits harder against his torso until she was practically dragging the entirety of her massive chest against his smaller frame with each movement. The overwhelming sensations were all completely new to Tyler’s susceptible male body, and the slick friction of her textured lips against his slippery shaft was already threatening to prove too much for him.
Finally, almost unexpectedly, instead of sliding tantalizingly along her pussy as Tracy slid back down his body, the glistening tip of his dick popped over the edge of her entrance, and he slid smoothly inside her for the first time. Tracy stared intensely at the young man’s face as his eyes widened at the pleasure, slowly sinking herself further and further onto him until he was buried up to the hilt.
“Does that feel nice?” Tracy cooed, letting him soak for a few seconds before she started moving again. Tyler could only nod as he continued to grope and suckle her tits with helpless need, buried under his former friend’s soft curves on the straining patio chair. The fear was still present in his eyes, but there was also a frowning intensity, the meaning of which Tracy knew all too well thanks to the years of sexual experience the Juice had given her. That was another thing she now loved about young men – how easy it was to get them to pop inside of her. Far from being a turnoff, however, making them lose control so quickly just made Tracy feel that much sexier. She wanted his cum inside her as soon as she could get it, and knew that Tyler’s overstimulated young body was more than ready to give it to her. She flashed him a knowing smile as she slowly slid herself off his cock, feeling his body practically convulsing with need underneath hers, and as expected his eyes widened with impending finality as his eagerness and inexperience began to get the better of him.
For his part, Tyler had loved feeling the voluptuous milf on top of him, around him, engulfing him, and had allowed himself to sink into her with abandon, but he was unprepared for the intensity of the sensation that flooded his body when her slick lips tugged along his sensitive shaft as she slowly pulled herself off him, and he was ashamed that her mature, experienced body had already forced him to the edge of his control after just one thrust. Tyler’s face burned with embarrassment, knowing that he was about to out himself as a virgin, but even though he tried to hold himself back like a mature, experienced lover, his young body needed to cum too badly, and he felt his cock beginning to tighten anyway. “Wait, Miss… um… I think I’m gonna-” he started to say, but then Tracy put a freckled finger to his lips and enveloped him for a second time, sealing his fate.
“Shhh…” she whispered encouragingly, and as she slowly slid him back into her, she watched his wiry arm muscles tense up as his eyes lost focus, and then she could feel his dick jerking inside of her, filling her with a heavy load of his potent semen while his slim hips bucked up against hers with all of the the surprising power of his young male body.
Not bad, only two strokes, she thought giddily to herself, filled with pleasure and satisfaction as she rode out her inexperienced partner’s heaving orgasm. Tracy didn’t mind at all that she hadn’t cum, of course – she was just happy to have taken care of Tyler’s needs, and she knew that the brevity of this little session would give her masturbation material for weeks to come.
“Thanks, lover, that was nice,” she cooed, bending over once more to give him a soft kiss on the lips as she slid his deflating dick out of herself. Even after having lost its rigidity, Tyler’s limp cock continued to twitch desperately against his slim abdomen in the aftershocks of the strongest orgasm of his life, while Tyler himself lay motionless on the lawn chair, still seeing stars after cumming so hard he almost lost consciousness.
It had been much more than just nice for Tracy as well, but she was a proper milf now, and had to play the part of the experienced older cougar no matter how delirious with pleasure she was at having successfully fucked the object of her sexual fixation.
“I’ll be in town for a while yet – I hope we can see each other again,” she said as she stood up to head back toward the house, still loving the way her mature curves bounced and hung off her body as she moved while Tyler’s copious jizz slowly oozed out of her juicy pussy.
“I, uh, I’d like that,” he stammered as he finally began to regain his senses. Tracy appreciated how cute and out of it her young lover looked as he pulled his swim trunks back up to cover himself before gingerly picking up her bikini top from where it was lying across the arm of the chair.
“Don’t you need this?” he called after her, eyeing the large, empty cups as the full weight of what had just happened finally began to sink in.
“You keep it,” she said, giving him a wink. “Same time tomorrow?”
Tyler nodded dumbly, fully aware that he wouldn’t miss it for the world. He knew it might be wrong, but he was in love with Tracy’s mom…’s busty, slutty cougar older sister.
Author’s Note: Thanks for reading! If you have any feedback, comments, or questions, I’d love to hear from you! If you find yourself enjoying my stories, please consider supporting my work on Patreon (Fidget1). Patrons get a full two months of early access to my stories, input into which stories I write, and some other fun perks. Every little bit helps, and your support is what enables me to keep doing what I love!