Katherine let out a deep, soulful sigh as she lent back in her executive chair and took a despondent look at the clock mounted on the wall of her office. It was already 8 pm, and she still couldn’t go home—not until she’d finished reviewing the stack of quarterly reports in her inbox. There was still a discouraging amount of work to be done, and with each passing minute, the tight-fitting pantsuit she was wearing seemed to grow more and more uncomfortable. Not to mention the pain in her lower back. Katherine reached back and rubbed the tender spot at the base of her spine, grimacing. She was too young for this kind of pain, she told herself. She wasn’t even 40! Not for the first time, she asked herself why she was like this—single, and with a respectable career but little else. What were other women her age doing? She thought about all the soccer moms she saw in their SUVs on her morning commute, devoting their whole lives to their husbands and children. Katherine’s nose wrinkled. She didn’t find that any more attractive. Then she thought about all the wine moms most of her male colleagues her age were married to, prying themselves out of bed at 10 am and pouring themselves their first glass of red wine 10:30. Katherine smiled. Now that, she could see some appeal to. Spending all day in a tipsy stupor, and letting the maid and the nanny do all the hard work. Katherine could definitely go for a few days of that. At least, in her dreams. She knew she didn’t have it in her to give up on her career like that. It wasn’t about the money. That, she had plenty of. It was about the self-respect.
Suddenly there was a knock at the door of her corner office, followed by an inquiring voice: “Mrs Berkeley?”
Katherine sighed again. It was Taylor, the intern. “Come in! And it’s Ms Berkeley.” She kept having to remind that girl.
The door opened and Taylor stepped inside, carrying a small box. She was a small, slight girl with her hair in elaborate braids, her many tattoos not quite hidden by her outfit. She was smiling, although her smile wilted slightly under Katherine’s severe expression. “Wow, you’re really working late, huh?”
“Just like you should be,” Katherine reminded her humorlessly. She’d conscripted Taylor to stay late with her and sort through some files. “Or are you finished?”
“Well, not yet,” Taylor admitted.
“Then I’m not entirely sure why you’re here, instead of completing the task I gave you,” Katherine scolded. She knew people called her strict, or even bossy. She didn’t care. In Katherine’s mind, if an intern couldn’t handle a little pressure from her, they clearly weren’t suitable for a position at such a prestigious company. “Or aren’t you capable of that?”
“No, I am,” Taylor replied quickly, although strangely she didn’t look shaken by the reprimand the way she normally did. “I just… wanted to give you something.”
“Give me something?” That took Katherine by surprise.
“Yes.” Taylor stepped forward, right up to her desk. “I got you a… thank-you present. To express my appreciation for all the hard work you do, and for inspiring me to work hard too. You’ve been a wonderful mentor.”
Katherine raised an eyebrow. That was deeply, deeply out of character for Taylor. Normally the girl was irreverent, bordering on insubordinate. Katherine had practically written her off. She was too preoccupied with her weird, new-age, witchy hobbies to be corporate material. But perhaps a little of her own work ethic had rubbed off. That would be gratifying. “That’s very thoughtful of you,” she said. “What is it?”
“It’s a bottle of wine!” Taylor presented Katherine with the box. It was just a plain, unmarked, cardboard box, but it had about the weight of a glass bottle full of something. “I hope you like it. I actually made it myself.”
“You know how to make wine?”
“Sure! In fact, I know how to make all sorts of things.” Taylor winked at her, with a strange, unreadable expression on her face. “I promise you, you’ve never tried wine like this before in your life.”
“I see.” Katherine carefully kept her face and tone neutral. It was a nice present, but she was a little suspicious of Taylor’s motives. Perhaps the young intern was just trying to buy her favor. “Well, thank you Taylor. I’ll be sure to try it soon, and let you know how I like it. In the meantime, why don’t you get back to work?”
“Sure,” Taylor said agreeably, and headed back out of Katherine’s office.
Now alone, Katherine opened the box and extracted the bottle from inside. It was red wine. It looked to have been bottled at home, just as Taylor had said. There was none of the usual information or branding on the outside of the bottle. Just a small label bearing the name of the wine—Cougar. Katherine placed the bottle on the edge of her desk, and then fixed her gaze back on her computer screen. But within just a few seconds, she found her attention drifting back to the bottle. It was awfully late. If she really wanted to finish reviewing the quarterly reports tonight, it was going to be hours more of work. Her energy levels were already flagging. Going home and having a couple of glasses of wine sounded absolutely heavenly. Normally, Katherine detested the thought of any delays, but perhaps she could tolerate it just this once. She had decided to just finish the current report she was reading through, but before long she gave up on even that. She just couldn’t concentrate anymore. It was useless. Katherine sighed, but then smiled to herself. She stood up, collected her things, picked up the bottle of wine and walked out of her office, bound for her apartment.
Half an hour later, Katherine made it through the door to her apartment. It was nice to be home, although unfortunately there wasn’t much homely about it. She kept meaning to decorate properly, but somehow she never found the time. As it was, it the decor was expensive, tasteful and completely cold and impersonal. Still, it wasn’t so bad. She normally didn’t spend enough time at home for it to bother her. Setting down her bag and shedding her suit jacket, Katherine went into the kitchen and retrieved a wine glass and a bottle opener. Her craving for a drink had only increased on her way home. She badly needed to relax. She headed into her living room, set the wine glass down on her rarely-used coffee table, and popped open the bottle.
From the moment she extracted the cork, Katherine’s nose was filled with a sweet, heady scent. She was no wine connoisseur but she’d been to plenty of fancy executive parties in her time, and from that experience alone she could tell Taylor’s wine was something special. She’d never encountered another wine with the kind of complex aroma as this, but already she was starting to salivate, and even feel a little intoxicated. She couldn’t wait to try a sip. Greedily, Katherine grabbed the wine glass and poured a glass of the red liquid. She had planned on pacing herself, maybe drinking half a glass at a time, but as she was pouring she zoned out for a moment, and before she knew it the glass was almost completely full. Katherine mentally scolded herself, although she couldn’t pretend to be genuinely disappointed. With as much restraint as she could muster, she raised the glass to her lips and took a sip.
It was ecstasy in liquid form. Katherine practically moaned as she swilled the fine wine around her mouth, savoring every little bit of its deep, delicious flavor. But not only did the wine taste incredible, it also had the middle-aged woman’s whole body thrumming with pleasurable warmth within mere seconds of drinking it. It was like an instant high. It felt fantastic. Almost immediately, her stress simply melted away. How could she be stressed when all she could think about was the wonderful taste in her mouth? Her body’s aches and pains, too, faded without trace. Katherine couldn’t believe it. Without hesitation, she raised her glass again and took another sip.
The next couple of hours were simply a blur. From moment to moment, it was all just a pleasurable haze. Katherine only snapped out of it when she tried to pour herself another glass of wine only to find, to her shock, that the bottle was empty. She’d drank every bit of it. That realization made Katherine giggle. She knew she was completely drunk. It wasn’t what she’d planned, but she was happy with it. More than happy; she was on cloud nine. Her stress was gone, and her body was buzzing enjoyably. She wasn’t nauseous, and she didn’t have a headache the way she normally did when she drank too much. Abruptly, Katherine realized that she had discarded her suit jacket at some point. Looking around, she saw it crumpled in a heap on the far side of the room—a far cry from how carefully she normally took care of her clothes. The creases would take forever to get out. Katherine laughed. She simply didn’t care. All thoughts of work were utterly gone from her mind, taken away by the delicious wine.
Looking down at herself, Katherine noticed that somehow, at some point, a couple of the buttons on her shirt had come undone, exposing the tops of her breasts. Experimentally, she used her hands to push her breasts together, forming a deep valley of cleavage. Katherine giggled like a naughty schoolgirl at prospect of showing that much skin. She never dressed in such a revealing way at work, but in that moment it was fun to imagine how people would stare. Even though she always wore conservative clothes, she’d never been lacking in the chest department.
At first she wasn’t sure why she’d undressed, but then Katherine realized she was feeling warm. Very warm. She wasn’t sure if it was the room or the wine, but she could feel her clothes clinging uncomfortably to her sweaty body. She decided she had no reason not to undo a few more buttons. Her drunken movements were uncoordinated, but after a few minutes of fumbling she was able to unbutton her shirt and shrug it off over her shoulders. The feeling of the air on her bare skin was an immediate relief. But then, she realized how tight and constraining her bra felt. After even more fumbling, she managed to unclasp that too, and soon enough she was able to free her breasts, leaving her completely naked above the waist. Katherine sighed happily. With her inhibitions massaged away, it felt freeing. She’d never felt so comfortable, so in-tune with her own body. It was wonderful.
It was then that Katherine noticed her body was flushed with another, very different kind of heat. Without really thinking about it, she allowed her right hand to drift down her body and rest lazily between her legs, and without really thinking about it, she started pressing with it, effectively rubbing herself over her clothes. Immediately, her happy sigh become a moan of surprise. She was so sensitive. Normally, Katherine didn’t masturbate much. She didn’t feel the need, but now, it was like her body was crying out to be touched. Katherine didn’t have the restraint to stop herself. She kept rubbing herself, pressing against her needy pussy in small circles until her whole body was thrumming with bliss. It felt so good. Katherine found herself asking why she didn’t touch herself more often.
Soon, she became greedy for more. Her pants were only getting in the way. After yet more fumbling, she managed to kick them off over her ankles. Too impatient to remove her panties, she simply pulled them aside and started touching herself directly. Her moans rose and rose, still interspersed with drunken giggles, as the pleasure grew more intense. It felt to Katherine like the whole city would hear her, but she didn’t care. She was so wet. As she touched herself she squirmed and writhed on the couch, tossing her head one way and the other as she gradually lost control of her body. It felt good to lose control, for once. To not have to be composed and collected. To let herself be free and sexual. To Katherine, that realisation felt transformative. Why hadn’t she done this before? She was definitely going to do it again, she decided.
There was only one problem, Katherine discovered after a few minutes: she couldn’t cum. She just couldn’t. The pleasure built and built inside her, but no matter what she did, it wouldn’t reach its climax. It was like there was something in the way, some kind of barrier, preventing her from being able to cum. It was maddening, and only became more frustrating as time wore on. Katherine’s movements became frenzied. She put all of herself into each moan, not caring who might hear. She used her other hand to start pawing and mauling at her tits, greedy for more, for anything that might take her over the edge. Drunk as she was, her self-pleasure was clumsy and uncoordinated, but still, it felt amazing—but it wasn’t enough. She couldn’t cum. Her thoughts turned to fantasy, and she found herself longing for more than just the touch of her own hands. She imagined being held, being kissed, being teased. She imagined another’s hands instead of hers, running over her body and her curves. And most of all, she imagined being fucked. She needed to be filled. Her body was crying out for a cock or a strap-on to fill the deep need inside her. That fantasy was almost enough, and her plaintive moans filled the tragically-empty room. But still, it wasn’t enough.
Eventually, Katherine’s strength failed her. It had been a very long day and the wine had made her drowsy, and the warmth filling her was making her long for sleep. Her body, too, was growing tired and beginning to ache with the exertion of how hard she was fucking herself with her fingers. She wanted to cum more than anything, but she couldn’t keep it up. Her movements began to slow, and eventually her arm sank to rest at her side. Her body was still twitching with need and pleasure, unwilling to accept that she wasn’t going to get the orgasm she so longed for. But frustrated as she was, Katherine was happy. She couldn’t remember a time she’d felt so few cares. She was happy to let her strength drain away, as she slumped down onto the couch, enveloped in her own warmth. Her vision started to blur and the room span around her, but her head was still filled with shockingly explicit fantasies that she knew would stay with her for a long, long time. As her eyes finally fell shut, the last thing she saw was the empty bottle of Cougar wine resting beside her on the table.
Katherine knew was that her whole head was throbbing. For a long time after she woke up, that was all she knew. Something wasn’t normal. Eventually, she managed to pry her eyes open, and was momentarily dazzled by the light in the room. Mercifully, she didn’t have a migraine but her head still felt like it was full of cotton wool. Her thoughts came slowly. Once her vision cleared, she realized she’d woken up on her couch. That was weird. She tried to piece back the events of the previous night, but it was a blur—at least, until she saw the empty bottle of wine, and it all came flooding back.
Instantly, she was mortified. She couldn’t believe how shamelessly she’d behaved. The only consolation was that no-one had been around to see it. Her second response, though, was a strange sense of satisfaction. She felt like she’d proven something to herself. She’d proven that she wasn’t as boring or strait-laced as everyone else seemed to think. That she could have some fun after all. Katherine smiled, as she started uncurling herself from her uncomfortable sleeping position and struggled up into a sitting position, still dizzy. Maybe she would have to get drunk more often.
Then, though, Katherine found her phone, and saw what time it was. Nine. Exactly the time she needed to arrive at work. For a moment, it was like her heart stopped beating. She flew into a panic. What was she going to do? She was going to be so late! But then, strangely, she relaxed as she realized there was absolutely nothing she could do. She was going to be late, whether she liked it or not, so what did it matter? It was out of her hands now. So… why not make the most of it? A crooked smile spread across Katherine’s face as a naughty idea occurred to her. She unlocked her phone, opened her email, ignored the many, many important emails for her and typed out a very quick message for her boss, telling them she was sick and wasn’t coming into work today. Katherine hit send. She giggled. She’d never done that before.
Suddenly, Katherine was confronted with the possibility of a whole day to use freely, however she wanted. Sure, she had reports to read and emails to respond to, but perhaps that could wait, just this once. So then, what would she do? Normally, the first thing she did each morning on waking up at five AM was exercise—some yoga, or a jog. She liked to keep herself trim and in shape. Katherine looked down at herself, and was surprised at what she saw. Her body was different. Her breasts seemed to have grown. She had a small, chubby paunch on her belly. Most of all, her hips had become huge and full to an almost unbelievable degree. It was like she’d gained fifteen pounds overnight—but in all the right places. How many calories had been in that bottle of wine? A familiar urge told Katherine that she needed to get up and go for a nice, long jog, to start to burn off all the weight she’d just put on. But with surprisingly little internal conflict, Katherine decided she wasn’t going to. She didn’t want to. Punishing herself with exercise sounded boring and exhausting, and that wasn’t how she wanted to spend her day of freedom. She wanted to have fun.
No matter what, Katherine reasoned, she was going to have to get dressed. Waltzing around her apartment naked all day was a bit too risque. She rose from the couch on unsteady feet, and made her way into her bedroom. She opened her wardrobe, but after several minutes of consideration she couldn’t see anything that she wanted to wear. It was all so formal, so restrained, so boring. She needed to wear something that expressed how she was feeling. Something freeing. Something that made it clear she was looking to live, laugh and love. She spied a small bundle, tucked away in the bottom corner. It was a sheer, black, satin robe. She’d never worn it. It had been a Christmast present from a colleague a couple of years ago. Katherine had considered it completely outside her tastes, but had kept forgetting to throw it out or regift it. For the first time ever, she was grateful for that. A robe seemed like the perfect thing. She picked it up, unfolded it, and slipped it on around her shoulders. The soft, thin, shimmering satin felt so luxurious against her skin. The lace detailing around the edges lent the garment a touch of elegance and extravagance that perfectly suited Katherine’s mood. There were just a couple of problems. Firstly, it was so sheer it was practically see-through. Looking at herself in the mirror, Katherine could easily make out the silhouette of her body under the robe. Secondly, it didn’t quite fit anymore. Even when she pulled the drawstring tight around herself, the robe bulged around her new curves in a way that was far, far more overtly sexual than Katherine had expected. But in the end, even though it bordered on indecent, she decided it was exactly the thing to wear to help her feel sexy.
Ever since waking up, Katherine had been nursing a deep craving. She’d been trying to ignore it, but it was proving completely irresistible. She wanted wine. No, she needed wine. She wasn’t sure why. It was unusual for her to be longing for a drink. Perhaps the hair of the dog was the perfect thing to lift the fogginess from her mind—not that it was particularly unpleasant—or perhaps the previous night had simply revealed to her how good a glass of wine could be. Either way, she was pining for one. But she had to wait, she told herself. She couldn’t start drinking so early in the morning. Or could she? It was almost nine-thirty, she reasoned. Practically mid-morning. And since she had taken the day off of work, what harm could there possibly be? In a matter of moments, Katherine was seduced by the temptation. She headed to her kitchen, seeking out the open bottle of wine she had leftover from cooking the previous weekend. To her disappointment, when she poured it out it turned out to be holding little more than half a glass. Her disappointment quickly evaporated when took a sip. It was so good. Not as heavenly as the Cougar wine Taylor had gifted her, but still, to Katherine it tasted amazing. She felt invigorated by it, and giggled as she was flooded by bubbly confidence. She didn’t have a care in the world.
Except one, perhaps. She was out of wine. That wouldn’t do. One measly glass for the whole day wasn’t even close to cutting it. Katherine considered going out to the store, but that would mean having to get dressed, and she definitely didn’t want to do that. So, she went into her home office and booted up her laptop, and started shopping around. She’d meant to only buy a single bottle to keep her feeling fun and frisky for the rest of the day, perhaps two, but in the end, she found herself ordering four boxes of wine from Franzia, two white and two red. Fortunately, the local Whole Foods she was ordering from had super-express delivery, meaning the wine would arrive at her door in just a few hours. With that knowledge putting an extra skip in her step, Katherine picked up her glass of wine and headed back into her living room, curled up on the couch, and turned on her TV to try and find something to watch to pass the time. There wasn’t much on, but in the end she settled on a Lifetime movie.
With the occasional sip of red wine to keep Katherine tipsy, the time passed much quicker than she expected. She spent much of it casually touching herself—it was so much easier through her thin robe, and it made her feel so good. The Lifetime movie proved surprisingly engrossing—sure, it was shallow, but it was certainly a fun little fantasy to indulge in. She was just wondering whether or not to devote her day to binging TV movies, when the doorbell to her apartment rang. It was her wine delivery. Bouncing with excitement, Katherine got up and raced to the door, glass of wine still in hand, heedless of the fact that she was still wearing nothing more than the sheer robe she’d put on that morning.
“Good afternoon ma’am,” began the delivery girl, when Katherine opened the door. “Can I… uh… um…”
The delivery girl trailed off, Katherine realized that she’d noticed what she was wearing and how revealing it was, and was having a hard time not staring. Katherine should have been mortified, but instead she felt exhilarated. Why not let the girl stare? She was young and kind of cute, in that delivery uniform and with her hair in such neat, tight braids.
“Can I, um, carry this in for you?” the delivery girl asked once she’d recovered some of her composure, gesturing at the boxes of wine on the ground next to her.
“Please do,” Katherine replied. Her voice came out husky and sensual, and she saw the delivery girl almost gasp. Katherine’s smile widened. It was good to know she was still hot. She stepped aside, allowing the delivery girl into her apartment. She stood by and watched the girl haul her wine inside, sipping the last dregs of her glass as she did. She made no secret of the fact she was admiring the delivery girl’s body. The uniform fit her very well, and she was clearly in good shape. For her part, the delivery girl was clearly nervous, but also seemed to welcome the attention, pushing her ass out behind her as she picked up the boxes of wine and set them back down again.
“Now I just need you to sign this,” the delivery girl said, offering Katherine a clipboard with a form on it. She was blushing faintly. “Do you have a pen?”
“Let me see.” Katherine decided to make her move. She felt powerful. She felt hungry. She wasn’t going to let this chance go to waste. She was going to seize the day. All the teasing she’d done to herself had left her so needy. “I think I have one in my bedroom. I could go and get it… or you could come with me.”
Her tone of voice made it absolutely clear what she was implying. The delivery girl blinked and stuttered for a few moments, turning bright crimson, but eventually she said: “Let’s go.”
Katherine’s wolfish grin grew wider. She shut her apartment door, took the delivery girl by the hand, and led her into her bedroom. “You got a name, cutie?”
“Valery.” She was obviously nervous, but her eyes were shining with desire and eagerness.
“Valery,” Katherine repeated. “I’m sure you need to get back to work soon, so let’s make this quick. Why don’t you come here and unwrap your present?”
Standing a couple of feet away from the younger girl, Katherine turned to face her. She folded her hands behind her back and pressed her chest out, fixing Valery with a smouldering look that promised everything the delivery girl might want. Valery was still blushing furiously but in contrast to her earlier stammering, she didn’t hesitate. She quickly crossed the distance between them and took a hold of Katherine by the hips, and pulled her in for a desperate kiss. To Katherine, the kiss was electric. She couldn’t remember the last time she’d been kissed at all, and she was sure she’d never been kissed like that. She couldn’t believe she’d been missing out on so much. Once again, she vowed she was going to do things differently from now on.
After a few moments, Valery pulled back from her and reached down to untie her robe. Katherine let out a sultry giggle, amused at how the delivery girl was so clearly torn between wanting to seem cool and composed and being unbelievably desperate to fuck her. In the end, her eagerness got the better of her, and she practically ripped Katherine’s robe open. But then, she just stopped and stared, her mouth open. She was practically drooling—drooling at Katherine, at her body. Katherine looked down at herself. She could understand why Valery was drooling. With her open robe and her newly voluptuous body, she was a vision of mature, confident sexuality. She wasn’t sure how it could be possible, but if anything, her curves seemed to have grown even more since she’d woken up. Her body was so soft, and the way the robe clung to her incredibly curvaceous, child-bearing hips made Katherine feel slutty and classy at the same time.
“What are you waiting for?” Katherine asked, her voice sultry and teasing.
Valery flew at her. Before Katherine knew what was happening she was in the delivery girl’s arms and they were pressing their bodies against each other. Valery’s hands were all over her, groping her and feeling her like she couldn’t believe Katherine was real. She dug her fingers into Katherine’s body, gripping her hips so tightly she left white marks. It was like she couldn’t get enough of the older woman. After thoroughly exploring her hips and her thick, juicy ass, Valery started raking her hands up and down Katherine’s back, her fingernails leaving distinct tracks and making Katherine gasp at the feeling. And the whole time, they kissed passionately, both of them utterly forgetting about shame or inhibition, until they were both left panting for breath yet too drunk on their own lust to pull back and compose themselves.
“Here,” Valery growled, placing a hand on Katherine’s waist and using it to shove her over onto the bed. Katherine didn’t resist. She was surprised to find Valery taking charge, but not unpleasantly so. She wanted the delivery girl to take her, use her, enjoy her. She could see the fire of want blazing in Valery’s eyes, and knowing she’d put it there made her feel so sexy. The wine only heightened the feeling, making the confidence and shamelessness feel easy and natural. She’d never realized she had this side to her, confident and sensual. She liked it.
“I need you to fuck me,” she purred. She saw that Valery was hurriedly removing her clothes, and Katherine took the time to tease the delivery girl even more. She crawled into the middle of the bed on her hands and knees, her movements languid and catlike. She looked back, and saw Valery’s eyes, glued to her hips, grow wider and wider as she pushed her ass out behind herself. Katherine shrugged her robe off completely and discarded it to the floor, leaving herself completely naked. Her nakedness only seemed to redouble Valery’s urgency to strip as quickly as possible. To further encourage her, Katherine bent forwards, resting her head and shoulders on the bed and raising her ass, using her hands to spread her fat, round ass. “Fuck me,” she repeated. It was just as much a plea as it was a command.
“God,” Valery breathed, her nostrils flaring. “I can’t believe this… I wanna fuck you. I’m gonna fuck you so hard.”
She was already completely topless, with her small, pert breasts exposed. When she removed her pants, it was Katherine’s turn to salivate. Between Valery’s legs was a large bulge in her panties that made it very, very clear what she was packing. It hadn’t been visible under her loose-fitting pants but now, the size of her bulge was making Katherine quiver.
“Oh yeah,” she whispered. “You’re trans?”
“Yeah,” Valery replied.
Katherine’s only response was to lick her lips suggestively. Grinning, Valery clambered onto the bed along with her, positioning herself behind Katherine and gratuitously running her hands along the older woman’s hips and thighs.
“God,” Valery moaned, in awe of Katherine’s body. “You’re fucking incredible.”
Katherine purred happily. Her body was ablaze. Knowing she was driving Valery crazy felt so good.
“I can’t believe I get to fuck a milf like you.”
Katherine gasped. A milf? She knew the term, of course, but she’d never expected it to be used to describe her. Her first instinct was to try and correct the delivery girl; she wasn’t a mother. But her body took that choice away from her. A roaring heat spreading out from between her looks reduced her to panting and moaning, her mind too flooded with arousal for words. No-one had ever said anything that hot to her in her life. She couldn’t explain it, couldn’t put it into words, but being called a milf was simply perfect. It was exactly how she wanted to be, how she wanted people to see her.
“F-fuck me,” Katherine eventually managed to say. It came out needy and whiny.
“Oh yeah? You want this?” Infuriatingly, instead of fucking Katherine like she desperately needed, Valery instead slid her dick in between Katherine’s huge, round ass cheeks, gently humping her body to tease her with the prospect of her hard cock.
Katherine’s moaning grew to fever pitch. She couldn’t believe this. Her arousal was driving her past the point of madness. She’d been teasing herself crazy since the previous night. Her body couldn’t handle it any more. She tried to beg, but all that came out was weak mewling.
“You were so confident before,” Valery told her. “But I guess really, you’re just a slut.” Her voice was so self-assured and smug. Now that she was caught up in the mood of the moment, the delivery girl had turned into a perfect bully.
“P-please!” Katherine screamed. She started rocking back and forth on her knees, grinding her ass against the shaft of Valery’s dick. Apparently, Valery was also barely holding herself back. The younger girl moaned and, unable to restrain herself any longer, pulled back and buried her cock in Katherine’s dripping pussy.
Instantly, they both moaned as one. Katherine was so tight, and being opened up by the pretty young trans girl’s impressive dick felt earth-shattering. It had been far, far too long since someone had truly filled her up, and Valery had done it in one stroke. Her whole body sang with pleasure. She’d needed to be fucked so much. She hadn’t realized just how much until Valery was buried to the hilt inside her. Nothing was better than that. Nothing.
Then Valery really started pounding her, and all remaining thoughts left Katherine’s head. Valery pulled back and then started pumping in and out of Katherine’s needy cunt over and over and over again, striking a merciless rhythm that left the older woman no time at all to recover before the next stroke had her moaning and whining all over again. For her part, Valery was panting and growling like a lioness, using every bit of her body’s strength to keep fucking Katherine senseless. The delivery girl reached forward and took a firm grip on Katherine’s hair, and used it to pull the mature woman back towards her as she fucked her, pounding her deeper and deeper. Katherine didn’t mind at all. Through the haze of her tipsiness and arousal, every feeling blended together into an adrenaline rush of wild pleasure that left her begging for more and more. She met each of Valery’s thrusts with one of her own, pushing back harder and harder as she sought to drive both of them to fresh heights of pleasure. She just wanted more.
They fucked in a wild frenzy, and it wasn’t long before both of their strength was spent. Katherine had cum countless times. Apparently, having someone else fuck her was the key. Her body was still twitching and spasming with the aftershocks as Valery pulled out of her and slumped over besides her on the bed. Judging from the ropes of cum dripping out of her cunt, Valery had found satisfaction as well. Katherine, too, collapsed in a heap, and the two of them giggled and panted as they looked at each other. It was obvious neither one of them could quite believe what had happened.
“Oh shit,” Valery said after a minute or two. “I, uh, need to get back to my shift.”
“Of course,” Katherine murmured happily. She was on cloud nine.
Valery stood up off the bed and started hurriedly putting her clothes back on. Once she was almost ready to go, Katherine got up too, and slipped her robe back on. She led Valery back out to the front door.
“So, um,” Valery began, sounding nervous again. “If… I wanted to do this again, any way that I could get in touch?”
“Oh, don’t worry.” Katherine giggled and reached over to the boxes of wine Valery had hauled in, and picked up the little marketing pamphlet. “I’ve got your number, and I’ll be sure to call.”
“Hi Katherine!” Taylor greeted her, standing outside the door to her apartment. “I brought you that wine, just like you asked for.”
“Oh, wonderful!” her boss—or rather, her former boss—replied. “Although, I’ve decided to go by ‘Karen’ now. So much less uptight.”
“Karen?” Taylor had to struggle to control her laughter. “Oh, that’s perfect. It really did a number on you, huh?”
“What do you mean?” Karen asked, puzzled.
“Oh, nothing.” Taylor waved away the question. “Can I come inside?”
It had been a week since the night Taylor had given ‘Karen’ the bottle of Cougar wine, and in that time, so much had changed. For one thing, Karen was no longer her boss. A few days earlier, Karen had given her notice and told her boss she was going to use her remaining sick days to avoid having to come in to the office at all. She didn’t want to waste all her time on her job anymore. She was entering middle-age—the prime of her life—and she had all sorts of other plans. She was going to travel. She was going to move out to the suburbs. She was going to embrace her creative side, and start making jewelry—maybe opening an Etsy store and seeing what she could sell. Her life felt so fresh and full of new opportunities. But most of all, she was going to drink wine and get laid.
Karen led Taylor inside and into her kitchen. There had been big changes there, too. Free from her job, Karen had finally found the time to redecorate. The whole place was covered with all kinds of warm, kitchy decorations. Taylor snickered at the ‘Live, laugh, love’ sign hanging on the wall.
“Here you go.” Taylor set down the large crate of wine on Karen’s kitchen counter. Eight bottles of Cougar. “You might want to pace yourself with it. I’m pretty sure it’s safe, but I’ve never given anyone this much before and, well, you’re already pretty far gone.”
“If you say so,” Karen replied. She’d been craving more Cougar ever since the first bottle had run out. She’d been drinking plenty of other fine wine in the last week—mostly delivered by her new friend Valery—but it just wasn’t the same. There was something special about Taylor’s concoction. “But I’m sure it’s fine. It’s just wine, after all.”
Taylor grinned impishly from ear to ear.
“You know, I really can’t thank you enough,” Karen continued. “If not for you, I’d still be stuck in that boring job. Instead, I’m reinventing myself.”
“You’re welcome,” Taylor snorted. “I didn’t do it for you, I did it so I wouldn’t have to deal with such a stuck-up boss anymore. But I guess you’ll never really be able to understand that, huh?”
It was true, Karen didn’t understand, but she laughed good-naturedly anyway. “I suppose I was pretty stuck-up.”
“You were a total bitch,” Taylor said emphatically. “But now… you make an adorable wine mom. My wine worked better than even I expected. Anyway, I guess I’ll leave you to it. Give me a call whenever you need more. I’m kinda curious to see how you end up, Karen.” She laughed again.
“Are you sure you need to go right now?” Karen was feeling horny. Nowadays she was always feeling horny, but she’d only just noticed how cute Taylor was. She was wearing her silk robe, just as she had been for most of the last week, and she started toying with the hem suggestively. “I have a bottle open. I could easily get you an extra glass. It’s really the least I can do. I’m sure we’d have a great time.”
Taylor found herself gulping nervously. Through Karen’s translucent robe, she could see everything. It wasn’t just her mind that had changed beyond her expectations. Her body, too, was now nothing short of incredible. She was perfectly soft everywhere, with curves to put a stripper to shame. She looked like a goddess. The perfect milf. Taylor had never seen someone exude such raw, sexual energy. Perhaps she’d created a monster. Despite the contempt she held for her former boss, she couldn’t help thinking of this Karen as a different person, and being tempted by what she was offering.
“Sure,” Taylor eventually replied, and let the cougar lead her into her bedroom.