Alex gets hired as a "personal assistant" to the wealthy Ms. King, and to his surprise she's a beautiful woman despite being in her late sixties. But that's not the only surprise in store for him...
WARNING: Contains non-con.
For the first time in his life, Alex was riding a limousine. It was truly bizarre, how only a week ago he had almost been ready to sell one of his own kidneys in order to make ends meet, and now he was on his way to his new job, in the most fancy way imaginable. For a poor, young boy like him, the experience was both nerve-wracking and exciting at the same time, almost like something out of a movie. Even the person behind the wheel looked exactly like you would expect a limousine driver to look like, a middle-aged, handsome, mustache wielding man, fully suited up with a chauffeur’s hat and a pair of white gloves.
The advertisement for the job was peculiar to say the least. It had simply been titled Personal Assistant, with a de***********ion that didn’t offer any information other than the bare minimum required for an ad to be allowed on the website he had found it on. Aside from the one sentence describing his work duties, the only things he had learned was that his employer was a rich, elderly woman, living several miles from the city, and that the job required him to live at the place of employment. It seemed a bit much, but it was only a summer job after all, so it wasn’t exactly a huge sacrifice on his part.
In reality, Alex knew that personal assistant was just a pompous title for what was essentially geriatric care, as had been made clear in the ad, albeit not directly stated. But he figured that taking care of everyday needs couldn’t mean much else, especially considering that no prior experience was required. It was far from what he had hoped to have as his first job, but he was desperate, and a job is a job. Besides, spending the summer in what was probably going to be some sort of mansion? That would be an experience to say the least, work duties be damned.
When he was contacted with the information that he had been offered the job, it had come as a shock. Not only due to his low expectations and lack of any worthwhile skill, but also due to the fact that he hadn’t even been to an interview. Furthermore, he had been required to agree to an oral contract over the phone, binding him to the job over the summer with no possibility of quitting. It was shady, almost as if something criminal was at work, but he accepted regardless. He needed this.
“We have arrived, young master,” the driver suddenly said, just as Alex’s field of vision was filled with the sight of his employer’s home, making his eyes go wide. It was way fancier than he had expected, not to mention larger, almost like a castle. In front of it there was a garden spanning several acres, complete with a fountain in the middle and a rosebush-lined gravel path splitting off on either side of it, before merging again where it led up to the front door.
The car came to a halt, and before Alex even had the chance to scoot over to the door to make his exit, the driver was already there, holding it open for him. Young master he had called him. Strange. He couldn’t help but wonder why a simple caretaker like him was worthy of such treatment, but he enjoyed it nonetheless. It made him feel important for the first time in his life.
Immediately upon setting his feet on the ground, he was met with a new face, that of a tall, beautiful young woman, barely looking older than himself at 18. With a welcoming smile, she made her way over to Alex from the large gate in front of the garden where she had been waiting.
“Welcome,” she said, holding her hand out for the significantly shorter boy to shake. “You must be Alex. I’m Clara.”
“Um, hello,” Alex replied meekly, shaking the woman’s hand with a weak, nervous grip.
“Nice to meet you.” She held Alex’s hand tightly, eyeing him from head to toe, a strange little smirk on her pretty face the entire time. Alex silently looked up at her, gulping uncomfortably at the attention despite the woman’s charms and warm welcoming. “Let’s not waste any time. You have work to do.” Clara spun around elegantly in her high heels, making her long, black ponytail swing in a wide arc behind her. “Oh, and don’t worry about your luggage, we’ll take care of it,” she added, looking back at Alex as she began walking towards the gate.
The indication that he was supposed to follow her barely registered in his head, as he was too busy admiring the suit-clad curves of Clara’s ample body. It wasn’t until she turned around to see him blushing that he finally snapped out of it, and with a few awkward steps that almost had him trip over his own feet he caught up with her, his eyes embarrassingly looking down at the ground.
Clara giggled softly. “Are you nervous?” she asked, before an awkward silence had the chance to set in.
“A little…” Alex admitted, doing his best to put on an innocent smile. “It’s my first time working. And the job de***********ion was a little… vague.”
“Apologies. It can be hard to interpret Ms. King’s needs at times, but I do hope I managed to put together a somewhat acceptable ad.” She kept her head straight and her chin up as she spoke, her wide hips gracefully swaying from side to side, despite the threat of the gravel path throwing her off balance due to her less than appropriate footwear.
“Err, not to sound rude, but… who are you exactly?” He felt dumb asking her such a thing, but as far as he knew there had been no mention of anyone other than his employer, and this girl clearly wasn’t her.
The pretty girl turned to Alex with her eyebrows raised and her hand on her chest in embarrassment. “Oh, forgive me! I’m Ms. King’s manager.” She went back to her smirk from before, in an almost robotic fashion. “Everything that reaches her from the outside goes through me first.”
There was something off about Clara, something that couldn’t quite be placed. As if she was withholding information. There were plenty of things Alex wanted to know about the job before meeting his employer, and this woman didn’t seem like the person to ask, but he was damn well going to anyway.
“Alright...” Alex mumbled as they walked past the fountain, unsatisfied with the lack of incentive to enlighten him about his duties. “So, could you tell me more about what I will be doing here?”
“Oh, you know,” Clara said, with a dismissive wave of her hand. “Just helping Ms. King with a little bit of this and that. Nothing difficult.”
“... Specifics, please?” This was starting to annoy him. Though he didn’t let it show, of course.
Clara sighed. “You’re mostly just going to keep her company. She gets lonely fast and needs someone to talk to in order to stay in good mental shape for her work. But she might ask you to help out with simple tasks. Making her bed, bringing her coffee, turning on her bathwater… that kind of stuff. Easy, right?”
It did sound easy. Too easy. The pay wasn’t nearly bad enough to warrant such easy tasks. Surely, there must have been something more to it, right? A few worst case scenarios popped up in Alex’s head. Perhaps Ms. King was a putrid, angry beast of a woman, enjoying making less fortunate souls suffer. Perhaps he was expected to take care of her toilet- and cleaning related needs. He shuddered at the mere thought.
“I guess,” Alex said in a distant tone, as they finally made their way up the staircase to the large, wooden front door. “Another thing, how come there was no job interview?”
“There was no need for it,” Clara dryly replied as she swung the door open, revealing the lobby’s decorative interior which Alex began admiring while listening to the manager’s words. Despite looking just like what he had expected given how fancy the outside was, he still found himself in awe. Two staircases ran along either side of the round walls, coming together into a large balcony overlooking the lobby, a chandelier hung from the ceiling, and several chinese vases and marble torsos sat on pedestals along the edge of the floor. “Ms. King saw your application and that was it. You really stood out, apparently.”
“Really? Why is that?”
Clara shrugged. “Who knows. You’ll have the chance to ask her yourself soon.” She began taking her shoes off, which was a bit unusual but made more sense when Alex noticed the line of slippers along the edge of the doormat. He quickly followed suit, happy to get out of the worn out sneakers that he had walking around in for far too long. With Alex right behind her, Clara began walking up the staircase, giving him a view of her big buttocks rubbing against each other in her tight suit, and had it not been out of respect for her as a colleague, he would have had a hard time looking away.
“Slippers, huh,” he casually said, as if wanting to point out what an oddity it was.
“Yup. No outdoor shoes in this house. She’s a bit of a clean freak, you see.”
Thank god, he thought. That took care of at least one of his worries.
They were quickly approaching a large mahogany door at the end of the second floor hallway, with fancy flower patterns carved into the wood, and Alex knew immediately that his had to be the master bedroom — the heart of the mansion. Clara stopped in front of it, between two large paintings on either wall that looked like they belonged in a museum, before turning to Alex, whose nervosity was showing more than ever.
“Okay, Ms. King should be working at her desk right now,” Clara informed him, placing her hands on his shoulders. “She’s really friendly, so just go in and say hello, alright?”
“... Are you not gonna introduce me?” Alex asked worryingly. He had always been a bit shy, and having someone with him when meeting a powerful woman like Ms. King would have helped tremendously.
“She doesn’t like to be disturbed when she’s working, so I try to leave her alone. But she’ll welcome you with open arms, I promise you that.”
“Okay…”
Clara gave him a warm smile and patted him on the shoulders before letting him go. “I’ll leave you to it,” she said, looking at Alex while taking a few steps backwards. “Good luck!” Just as elegantly as before, she spun around and walked away, presumably back to her office to continue her work as a manager.
As soon as Clara was out of sight, Alex turned back to the large door and with a nervous gulp grabbed the golden handle. The idea of preparing a few lines for a hypothetical conversation occurred to him, but considering he knew so little about his employer he chose not to. He pressed down on the handle, feeling his heart beat faster and faster as the door slowly creaked open.
Little by little, the bedroom was revealed to him. What dawned on him immediately was just how immense it was, looking several times bigger than his own apartment. Although presumably it served as more than just a bedroom, as it had a fancy lounging area directly to the left, with the far left wall next to it being covered in a large shelf absolutely bursting with thick, leather bound books. The furniture was as fancy as you would expect, antique empire sofas and armchairs with a table in the middle, all made with carved mahogany. A large, at least 60-inch TV hung on one of the walls next to the area.
On the right side of the room was the bed, a fancy, king sized one. Just like all the other furniture, it too was made out of carved mahogany, and dressed in white, gold lined bed clothing. Next to it, there was another door, presumably connected to a bathroom.
A faint click could be heard, turning Alex’s attention towards the source of the sound, the desk in the middle of the room near the back wall, just in front of him. And there she sat. Ms. King, with one hand on a closed laptop in front of her and a satisfied smile on her face.
“Welcome, dear,” she said, her tone like that of a loving mother with a slight quiver in her voice, likely due to her age.
Alex stepped in and carefully closed the door behind him, feeling a bead of sweat run down his face as Ms. King’s mere presence seemed to drain any confidence he could hope to make use of when making his first impression. She immediately began eyeing him up and down much like Clara had, but this time Alex didn’t even notice, his anxiety preventing him from even holding proper eye contact.
“I hope my employees have treated you well,” she continued. “Would you like something to drink?”
What Alex could make out from the quick glances he threw her way was that she was younger than he had expected, or at least looked younger. Still, her hair had clearly lost its color, and she seemed to have an overall style that reminded of a grandmother, like a big pearl necklace and cat eye glasses with a thick, black frame.
Alex let out a light cough. “No thanks, ma’am,” he replied, making a conscious effort to not let his nervosity show.
Ms. King took off her glasses and pointed her open palm towards the chair on the opposite side of her desk. “Have a seat, dear. We’ll begin discussing your work immediately.”
Reluctantly, Alex walked over to the chair and sat down as the old lady continued to stare him down. Despite his attempts at staying calm, he couldn’t help but nervously clutch his thighs tightly in his hands, watching Ms. King silently begin to flip through a bundle of papers. She paused to read one of them for a few seconds, then looked back up at Alex.
“Alex…” she mumbled. “You look just like in your picture.”
His picture. That’s right. He had almost forgotten that the advertisement had stated that a profile picture was required. Other than that, there really wasn’t much written in his resumé, he didn’t have any work experience after all. It was strange that he had been hired at all, especially without an interview.
Unexpectedly, Ms. King rose from her chair and made her way around the table, making Alex freeze in place as she stopped next to him with their eyes locked. Ms. King said nothing. It was difficult to determine what she was thinking from the blank expression on her face, but Alex couldn’t help but think that he was being judged somehow.
It wasn’t until now that he noticed how surprisingly beautiful Ms. King was. She must have been over sixty, but she had clearly taken good care of herself over the years. Her face was clearly that of a woman who had been supermodel material in the past, with blue eyes that almost seemed to glow, eyebrows that had stayed nice and full over the years, high cheekbones and an overall well-shaped chin and jawline. Her hair hung in two large, silvery-white braids from the back of her head and draped over her shoulders and chest. The only thing that stood out a bit was her quite long, hooked nose, but in Alex’s opinion it only made her more gorgeous. He had heard about studies done on female beauty, finding that women with a bit of a quirk or “flaw” were often considered more attractive, as it kept them from looking too plain, and this was a prime example of that. She did have wrinkles, as expected, but not nearly enough to make her look like an old hag. They were… charming, in a way.
Ms. King bent down and moved her hand towards Alex’s face, making him recoil slightly in confusion, but froze once again when she grabbed him under the chin and tilted his face up. She furrowed her eyebrows, clearly inspecting every part of him, her eyes moving up and down, while his moved away in embarrassment. His face wasn’t exactly a part of him that he was proud of. He had quite feminine features, a jawline that was rounded and smooth, puffy lips, and eyelashes that always looked like they had mascara applied to them.
“Umm.... Ms. King?” Alex mumbled, his face flushed and his heartbeat quickening.
“Please, call me Evelyn,” she cooed, turning Alex’s head from side to side while her eyes continued to scan him. Her alluring presence was so overpowering that he could barely move, with her gorgeous face right in front of his and her scent slowly creeping in. Not only did she look good, but damn, did she smell good as well. A sort of sweet, flowery scent, the type you just want to get right up in your face and take deep sniffs of.
“What are you doing, Evelyn?”
“What am I doing? Inspecting my new employee, of course!”
Alex sat quiet for a moment, as she ran her hands through his ear length, brown hair, before he decided to speak up. “I thought we were going to discuss my work…” His words seemed to stop Evelyn in her tracks, and the little smirk that he thought he could see on her face quickly faded.
“Oh my, forgive me!” she said, clearly feigning ignorance. She let go of Alex and went to sit down in her seat, before putting on her glasses and picking up the paper from before. “I can be a bit absent-minded sometimes. But you’ll get used to that.”
“Right…” Alex replied, his tone almost making his doubting obvious.
“Now, then. Did Clara tell you anything about the job?”
Alex shrugged. “A little. She said I was here to keep you company and help you with basic things. Like… making your bed and bringing you coffee and stuff.”
Evelyn held the paper in front of her, which had been made clear was Alex’s resumé. She silently read off of it while listening to him speaking, her eyes alternating between him and the resumé almost as if she were sizing him up, while a subtle grin slowly grew on her lips.
“That’s right,” she said in an upbeat tone. “There isn’t that much more you need to be told, honestly. Perhaps it would be better to put you to work immediately.” She put the paper back down on her desk, as her grin grew wider yet. “You wrote that you used to intern at a massage parlor, yes?”
Alex sat dumbstruck for a moment. Surely she wasn’t expecting a massage, right? Not that it was a difficult task, but it was a far more intimate one than he had expected. “Err, well yes… But only for half a year.”
“Oh, that will do just fine. I could really go for a neck massage right now.” Without skipping a beat, she stood up and began unbuttoning her purple business suit. “I’ll need to use your chair. Mine’s too tall.”
It took Alex a moment to realize what was going on, as Evelyn once again walked over to him. Did she actually expect him to give her a massage? This was all going way too fast.
“Go on, get up! This is your first task!”
“G-giving you a neck massage?”
“You’re not gonna refuse, are you?” she purred, leaning down until her face was right in front of his. “This is your job, Alex.”
Alex gulped. “Umm… okay, I’ll do it.”
Reluctantly, he got off his chair and went to stand behind it, watching the elderly woman continue to unbutton. He only noticed now that she was quite tall, towering over him by at least half a foot. Not that Alex was anywhere near tall, of course. If asked, he would have insisted that he was five foot five, but in truth he was barely above five foot four. He also noticed that her height was accompanied by width, with child bearing hips that were beautifully rounded and connected to a slim waist. It was hard to blame Alex for becoming entranced with the way Evelyn looked, especially considering she was undressing right in front of him. Could she really be that old?
When she reached the last couple of buttons, it dawned on Alex that she wasn’t wearing anything under her suit jacket. Her flat tummy was partially revealed, and as Alex’s eyes traveled up they were met with another beautiful sight. A large pair of breasts, held up with a sexy, black bra, the type you would never expect a woman of her age to wear. It clearly struggled to contain those big tits, almost as much as Alex struggled to avert his gaze. Evelyn took notice of his reaction and giggled softly in response.
“Oh, Alex,” she teased, her voice strangely affectionate. “Don’t tell me you’re actually staring at my chest?” She held her arms back and pushed her chest out, letting the jacket fall to the floor, and giving Alex an even better view.
He blushed and looked away. “I-I’m sorry, Ms. King!”
Not even five minutes had passed since he met her, and already he had been caught staring at her breasts. He was off to a bad start. But truth be told, most men would have reacted the same way upon seeing what he had seen. Evelyn was full of surprises. Even the skin on her breasts and belly were well preserved, with only the slightest bit of sag and wrinkles, and a few moles here and there.
“Don’t be, sweetie. I’m 68 years old, you know. I appreciate every bit of attention my body gets.”
68 years old?! Alex thought to himself, the number echoing in his head, almost sending him into a daze. He couldn’t believe he had been fawning over a woman who was old enough to be his grandmother. As he stood there, dumbfounded, he didn’t even notice when Evelyn sat down on the chair, ready for her massage.
“Now then, Alex,” she said, turning her head to look him in the eyes, while sliding the straps of her bra off her shoulders. “Show me what you can do.”
“Y-yes, Evelyn,” he stammered, reaching out with his trembling hands. His heart was racing. Was this really okay? Giving a massage to the person who was going to be his boss during the summer, while she was topless for that matter? He almost felt as if time stopped while his hands slowly closed the distance between them, as if the universe was trying to tell him that this was wrong, and that he should stop before it was too late.
But when his hands finally connected to Ms. King’s shoulders, all his doubt went away in an instant. Feeling the warmth of her smooth, somewhat loose skin against his palms calmed him down right away, and the old woman clearly enjoyed it. Almost immediately upon feeling his hands on her stiff shoulders, she let out a sigh of relief as she closed her eyes and leaned her head slightly backwards. It had been a long time since someone had touched her, and she was happy that it was at the hands of someone with experience when it came to just that: touching people.
“Mm… don’t hold back now, I’m not frail,” she instructed, her voice mellow and soothing.
Alex obeyed and silently started squeezing and rubbing her, just like he had been taught at his internship. He was a little rusty, but Evelyn didn’t seem to mind. She began moaning softly, adding fuel to the fire that was the erotic scenario taking place, causing a slight stirring in Alex’s pants.
“You’re good at this…” she said between moans, just as Alex’s hands pressed against her upper neck. “I just know you’re going to be perfect for this job.”
“Umm… how come you chose me in the first place?”
Evelyn chuckled. “Not very confident, are you?”
“Well… It just seemed strange. I’m a high school dropout without any work experience.”
“That doesn’t… mm... matter,” Evelyn moaned, her voice almost giving out from pleasure. “The job isn’t very hard, you know.”
“But still, why me?” Despite the uncomfortable dialogue taking place, his hands worked Evelyn’s stiff muscles diligently. His muscle memory didn’t betray him, as he moved his hands over her shoulders and practically felt her tension dissolving in his hands with every squeeze.
She let out a sound that was something like a moan mixed with a giggle, and laid her right hand on his left. “Because you’re an adorable boy, Alex. And the fact that you can give a great massage? It’s like I hit the jackpot.”
Alex blushed deeply. He stopped his massage in embarrassment, still holding on to Evelyn’s shoulders, while she began caressing his hand. Casting a glance back at him, she noticed his flushed face and smiled in amusement. Alex met her gaze and looked away, his mouth awkwardly opening and closing repeatedly as he tried to think of what to say.
“... W-well, surely the job must get harder than this?” he stammered, convinced that Evelyn was hiding something.
“You could say that,” she said in a sultry tone, with her eyes still fixated on Alex’s. “Here, I’ll show you right now. Come stand in front of me.”
He eyed her for a moment, trying to deduce what she wanted from him, before reluctantly following her order. As he went to stand in front of her, he now had a full frontal view of her large chest, barely covered by the black fabric of her lingerie, and it was almost too much for him. His mouth went dry as he stood there, gaping like a fool at what he saw, though not for long, as Evelyn suddenly reached out and grabbed him by the chin.
“Come here, you sweet little thing,” Evelyn purred, pulling his face towards hers as she leaned forward. In one quick motion she let go of his chin and grabbed the side of his head instead, doing the same with her other hand. The distance between them quickly closed, as did Evelyn’s eyes. Alex’s breath left him as he realized what was happening. And he let it happen.
Their lips connected in an aggressive kiss, at least on Evelyn’s part. Her left hand moved to the back of Alex’s head, pushing him firmly against her as their lips flattened against each other. She held him there for a moment, before letting them separate for a fraction of a section, eliciting a lewd smacking sound from both of them. Their lips touched again, this time far wetter than before. Evelyn couldn’t hide her eagerness, as she moaned loudly, almost seeming like she wanted to eat Alex alive, going absolutely wild with her wet, wrinkle-lined lips around his round, full ones. Her hands held him firmly in place, and this time she wouldn’t let them separate again.
Alex’s mind was completely clouded in both excitement and confusion. He was absolutely loving this. It felt incredible having someone so eager to kiss him despite him having done nothing to instigate it. She was kissing him because she wanted to kiss him, and that made him feel like a million bucks.
But why were they kissing exactly? Why was this his task? But then again… did it really matter? Ms. King was an old woman, but she was stunning and seemed sweet and gentle. Perhaps it was best not to think about it too much.
Suddenly, Alex experienced something completely unexpected. Evelyn’s eager tongue pressed past his lips, and without any shame she started exploring every crevice in his mouth, making erotic slurping noises. Alex’s eyes shot open at this new, alien feeling that was turning his brain into mush. He felt the old woman’s saliva start to flow into him, and he swallowed it like it was sweet nectar. It was strange how the thought of kissing a 68 year old woman would have disgusted him a week ago, but now it was driving him nuts.
Alex grabbed Evelyn’s head just like she had his, and reciprocated by meeting her tongue with his own. They were both making muffled moaning noises as their tongues wrestled each other, and their hands were furiously rubbing and gripping one another’s neck and hair.
For a moment, Evelyn let go of Alex, to quickly reach behind her back and unclasp her bra, then threw it on top of her jacket lying on the floor. Normally, the cleanliness-obsessed woman would have never done such an outrageous thing as throwing clothes on the floor, but now, there was only one thing on her mind:
Breaking in her new boy-toy.
She grabbed Alex by the hands and guided them to her huge tits hanging free in all their glory, pushing his palms against them, prodding him to fondle her. He immediately began squeezing them, sinking his fingers deep into the soft, mildly sagging flesh, making sure to apply his massaging skill as well as he could. His hands traveled with hard grips all over them, from base to nipple, as if wringing them out in a hope of there being a deposit of mother’s milk.
Sure enough, the added sensation of his skilled fingers going wild on her breasts brought Evelyn even greater pleasure, increasing the volume and frequency of her moans as she held Alex even tighter. And of course, causing a massive flow of blood into the one part of her that was going to be the star of the show, the one part that separated her from other women.
She really had struck gold. Little Alex was just too cute! A love-starved, shy and effeminate boy eager to please what she could only assume was his first woman. He wasn’t exactly the dream partner to the average girl, after all. But to her? Hell, he was basically a gift from above.
And the poor thing had no clue what was about to happen. Evelyn almost felt bad for him, but he would most definitely struggle when it came to love out there in the real world, with normal girls who had normal standards. She was doing him a favor. It was a win-win situation.
The bulge in her pants was prominent, but not yet noticed by Alex, who was still focused on the passionate kiss they shared. Evelyn became more and more impatient, as the aching caused by her tight clothes turned the kiss into a frustrating teasing to her, despite how pleasurable it still was. She couldn’t stall any longer. She wanted to know how well her “assistant” would handle his real duties.
“Off with your pants and underwear,” she growled after breaking the kiss, letting her impatience show.
Alex merely nodded, a string of spit still connecting the two, as he hooked two thumbs in the waistband of his tight jeans and pulled them down with a quick tug. Evelyn immediately resumed the kiss, diving in even harder this time. It was essential that Alex’s eyes didn’t wander too much, lest her plan be ruined.
The kiss was short-lived. As soon as Alex’s pants and underwear hit the floor, Evelyn grabbed him by the shoulders and spun him around, showing off a good portion of his girly ass under the hem of his flannel shirt. This was just getting better and better. Those smooth, bubbly cheeks were everything she had hoped for and more.
“Umm… Ms. King?”
The boy turned around to look at her, dangerously close to putting her secret at risk, prompting her to shift into high gear. With two surprisingly strong arms, she reached around his chest and pulled him back gently but firmly. Leaning back slightly, she had him sit down on the lower part of her abdomen, just above her bulge, holding him in place as she breathed heavily onto his neck from excitement.
“What are you doing…?” he asked timidly, feeling her fat, mature tits pressed against his back.
“I’m sorry it has to be this way, Alex.” She lovingly cupped one of his cheeks with a wrinkled hand, but judging from the excited tone of her voice she wasn’t sorry at all. With the same hand, she quickly grabbed the zipper handle of her fly, pulled it down and reached inside. From beside him, she watched Alex’s expression go from confusion, to shock, then finally to complete and utter horror. “Now then—”
“What the fuck?!” he screamed, interrupting whatever Evelyn was about to say. “Let me g-mff!”
“Hush, dear. I promise to be gentle, there is no need to worry.” With strength that no old lady like her would be expected to possess, she held her hand tightly over Alex’s mouth, muffling his continuous screams of protest. His flailing lower legs were easily bent back under the chair by her own, and each of his arms were likewise held in place by her stronger ones.
“It’s a bit larger than average, but it’s nothing a big boy like you can’t handle, I’m sure of.”
She casually rested her chin on his shoulder and proudly looked down at what had sent him into a panic. At the menacing anaconda between her legs that would have put porn stars to shame, long and fat, a shade darker than the rest of her somewhat pale skin, and with a bright purple, broad, flat tip, almost completely covered in foreskin despite her raging hard-on. She may have been old, but her cock seemed to have just as much vigor as if she were in her twenties, although the coarse, gray hair above the base was a clear contrast to that.
As it twitched and throbbed, the tip leaked precum like a broken faucet all over Alex’s crotch, quickly leaving a massive stain on the lower part of his shirt. Splayed out on the chair beneath it, Evelyn’s sperm tanks rested, each one the size and shape of a large egg, covered in a wrinkled, hairless sack.
A strong musk emanating from her cock battled the flowery scent of the otherwise squeaky clean old woman, turning into a strange mix of femininity and masculinity that somehow accentuated her already powerful presence. Even from way above, the shivering, panicked Alex could clearly smell it, somehow making him feel even more outmatched, as if the scent of her cock was proportionate to its massive size, in a display of complete sexual superiority. It was truly bizarre, not to mention humiliating, how she had him so completely beaten despite him being a young man and her being an old woman, if one could really call her that.
Alex’s fingers clawed into Evelyn’s thighs, desperate to escape her clutches, but the old lady didn’t let up for a second. She had one of his arms hooked behind hers, her hand still covering his mouth, while her other arm awkwardly fumbled with trying to hold his other arm back as she reached her hand down into her pocket. Having planned ahead, she extracted a small bottle of lube that she had left open, to ensure a quick and easy use. The sticky substance was already leaking everywhere, as she brought the bottle above her cock and began pouring out the content onto it, and as Alex took notice, his throes of protest noticeably increased in intensity.
“Shh-shh-shh, sweetie, it’s going to be okay,” Evelyn softly comforted into his ear, her arm now in Alex’s tight grip as he tried to pry it away but ultimately achieving nothing. “It will hurt in the beginning, but by the end of your employment you’ll never want to live without it, I’ll make sure of that.”
Her words filled him with rage and fear, especially considering how casual her tone was. Was she planning on keeping him as a sex slave throughout the entire summer? There was no way this could possibly be legal, regardless of him having accepted the job or not. And how come she had a penis? What was she?
Evelyn put the small bottle on the desk in front of them, then began jerking her slathered cock, pulling her foreskin up and down, revealing the fat, moist tip, until the entire length was covered in a sheen of lube. With her arms still tightly secured around Alex’s, she lifted him up a few more inches, trying to set him up for insertion but finding it difficult to angle him correctly while still trying to hold his flailing limbs back. Alex tried pushing his hips forward, desperate to get his butt as far away from the huge pole that was about to skewer him, but was quickly pulled back by Evelyn.
“You’re not getting away, Alex,” she said matter-of-factly. “This is your duty as my employee. Just relax and let it happen.”
Alex’s body kept spasming as Evelyn finally managed to hold him firmly in place, while he refused to give up without a fight. But when he felt himself being lowered onto her massive rod, he knew there was nothing more he could do. He tried to clench his cheeks to deny entry, but it was hopeless, as if trying to stop a battering ram with a saloon door.
His pink little hole was soon pressed against her slippery tip as she impatiently tried to get inside of him, but it was just too tight. She lifted him ever so slightly, before attempting again, feeling his ring start to loosen up just a tiny bit, but not enough to let her in. She repeated the process again and again, and in one final, desperate act of protest, Alex turned his face to Evelyn, as much as he could with her strong hand over his jaws, and gave her a pleading look as the first of many tears started running down his cheeks. Evelyn had a wide grin on her face, in that moment reminding Alex of a witch, although perhaps that was just because of the anger he felt.
And then it happened. Evelyn breached his final defense, pushing her skin-covered glans past his sphincter. Alex let out a muffled scream through her fingers and threw his head back as his hole was stretched out more and more by the increasingly thick meat. A jolt of pain shot through his body, causing him to spasm out even more than before.
“Oh my god, Alex…” Evelyn moaned. “You just get better and better with every part of you that I explore… God, that’s tight.”
Pushing up from the seat with her ass cheeks while letting gravity do the rest enabled her to slowly start filling her boy-toy up with her mature cock. Little by little, it slid through him, making her moan loudly while Alex silently stared up into the ceiling, the froth from his mouth making itself apparent between Evelyn’s fingers.
Before long, Alex was sitting in her lap with Evelyn’s cock hilted near balls deep in his ass. He could feel her hot breath on his neck as she held him tight against her, her fat tits flattened against his back. Without saying anything, she began slowly pushing her hips against him, grinding her cock against his insides only ever so slightly, but increasing her pleasure tenfold.
“Mmm… you’ve gone so quiet, dear,” she purred into his ear, reaching out with her tongue to give it a wet lick. “Perhaps you’re enjoying this as much as I am? Ooh, I’m gonna fill you up so good...”
Tears streamed down Alex’s face, his exhausted body only managing to shiver slightly as he used his last bit of energy to fight back. But he knew that it was hopeless. He was being completely dominated by a woman 50 years his senior, his limbs held firmly in place, his asshole burning in agony from the double-digit inch dick rearranging him, and to add insult to injury, she was now gleefully licking his tears off his face, moaning as if they were the most delicious thing in the world.
“Granny’s going to take great care of you, sweetie,” she said. “I’ll make you feel good, I promise.
For a moment she stopped moving, as she found it difficult to push off the chair and into his tight little boy-pussy, but she had other techniques. Instead of thrusting outright, she instead began simply flexing her thick, strong glutes repeatedly, causing a sort of bouncing motion to take place, resulting in short, quick humps, bringing near constant jolts of pleasure throughout the old lady’s body.
This was the type of fucking she loved most. Slow, yet unrelenting. Loving and gentle, yet forceful. She sniffed Alex’s soft, medium length hair as her rutting continued, drawing in the fruity smell of his shampoo, enjoying every feminine aspect of him. His muffled, girly whimpering as she claimed him was music to her ears.
“You have no idea how I’ve longed for this… There are so many things I’m going to do to you, my cute little slave.”
Just thinking about all the nasty things they would be doing over the summer excited Evelyn even further, increasing her thrusting speed proportionally. But it wasn’t enough for her. She wanted to touch him, taste him, break him.
With Alex no longer possessing the strength to resist her, she used her free hand to unbutton his flannel shirt, revealing his tan, feminine curves. A thin waistline that blossomed out into a wide set of hips, and a flat, smooth chest with small, light-brown nipples.
“Gods… you’re— oh lord... so… damn… adorable!” she purred, licking Alex’s face, and gently massaging his nipples. Her words were strained with the pleasure of her continuous thrusts into his hot depths. “Mm, it should be a crime to cover up this body…”
The tight walls of his asshole felt better than she could ever have hoped for, as if this was his purpose in life, to be bred into a little cock-slut for her long-neglected urges. He had the looks, the tightness, the weakness, everything she needed in a lover.
Alex was completely out of it at this point. He hated himself, partly because he wasn’t able to stop her, but mainly because it felt so good. Throughout all the pain that she was causing him, there was undeniable pleasure, as her massive meat aggressively milked his prostate, keeping him on the verge of orgasm during the whole process.
He tried to think rational thoughts, that he shouldn’t like this at all, that Evelyn was nothing but a disgusting old hag who liked taking advantage of small boys, but he just couldn’t convince himself of it. He obviously wasn’t enjoying getting raped, but she was without a doubt a sexy woman, great at kissing and smelling of roses, and had it not been for her cock, Alex would have jumped at the opportunity to have sex with her.
All of a sudden Evelyn turned his head to the side, and in one quick motion removed her hand from her mouth as she hungrily planted her lips onto his. It ended up being as effective in keeping the boy quiet as holding her hand over his mouth, although perhaps that was just because he had given up. Alex did nothing to return the kiss, instead just keeping his mouth open for Evelyn to ravage him even more eagerly than when they kissed previously.
All the while, she kept humping away at him, feeling the pleasure building up more and more, churning a massive load of spunk inside her. But she wanted it to last longer. They kissed for another ten seconds or so, after which Evelyn suddenly ceased her movement all together, broke the kiss and then put her hand over Alex’s mouth again.
“I will remove my hand, but you will keep quiet,” Evelyn ordered, staring deep into his soul. “Nobody is going to help you anyway. Do you understand?”
Alex meekly nodded, his eyes drenched in tears as they looked back at her. Then, finally she released her grip, letting him breath with his mouth, but also making his pathetic sobbing apparent, somehow making him feel even smaller.
“Please stop…” he begged. “Why are you doing this? I hate it…”
Little did Alex know that his begging was only making Evelyn hornier. “Oh, Alex, you sweet boy. You signed up for this, remember? You let this happen. And it’s going to continue happening every day from now on. You might as well try to enjoy it.”
“... Doesn’t matter if I accepted the job,” Alex retorted, with a little more fight in his voice than a moment ago. “This is illegal!”
Evelyn snickered cruelly, cupping Alex’s cheek with her left hand. “I know, dear. But you don’t stand a chance against me in court. Nobody would believe anything you say. You’re a poor, young boy with nothing to lose, and I’m a wealthy old woman. People like you always try to extort people like me, it’s nothing new.”
Alex cast an angry glance at her, but she just smiled at him and licked her lips humiliatingly. Suddenly, she wrapped her arms around him in a tight hold and went back to humping him, with increased vigor from Alex’s cute, agitated expression. This time however, she pulled him down with each thrust, burying herself balls-deep within him over and over again.
This new-found stimulation was quickly getting too much for Alex to bear. Evelyn’s thick meat massaged his prostate even harder now, and the pain and pleasure was mounting up to a mind-numbing level. It was as if someone was tasing him in his anus each time she slammed into him.
Evelyn howled like a mad woman. Never had she experienced this type of pleasure, her entire shaft stimulated, the tight ring of Alex’s asshole clinging to the very base of it, all the way down to her pubic mound as if giving it a kiss with every thrust. The wet sound of her lubed up dick being massaged by his guts was hot in its own right, but paired with her slave’s delirious crying and moaning it was truly mesmerizing.
She was getting close. A massive wad was slowly building up inside her, to what would surely be the biggest cumshot in her life. And not a single drop would go anywhere but deep inside Alex’s tight bubble-butt.
“I’m getting close, Alex-sweetie,” she whispered in his ear. “Hope you’re ready for granny’s hot seed…”
The only thing missing was seeing Alex reach his own climax. A sight like that would surely send her over the edge immediately, and truth be told, despite all the pain she had caused him, she did want to pleasure him as well.
She started licking his ear, circling the edge of it with her tongue, sticking it inside and letting her hot saliva flow into it and run down his neck. With one hand, she pinched his right nipple, twisted and pulled it, drawing a cry of pain from him. With the other, she reached down to grab his small, twitching dick, and quickly began jerking it up and down with three fingers. Alex wailed in response, finally getting the stimuli needed to reach orgasm.
Evelyn slammed him against her harder and faster than ever, as his little prick began shooting out thin lines of watery semen. It was weak and pathetic, but still so fucking hot. She could feel her saggy, sweaty balls tighten, her fat cock twitching violently inside Alex, as a powerful surge coursed through her nether region.
“Oh, god, here it comes, Alex!” she shouted. “Take my week-old cum!”
As the cum forced itself through her cock, it practically exploded inside Alex’s asshole. One spurt of it contained more semen than Alex had produced in his entire orgasm, and Evelyn wasn’t even close to done. Throbbing each time, her baby-batter shot out again and again, hot, thick and creamy, pooling deep inside her broken little toy. She roared throughout the entire orgasm, holding Alex in an iron grip tightly against her pulsating cock as it painted him white from the inside. He felt himself filling up with her warmth, and at this point it just made him feel relieved, as it signaled that it was finally over.
After what felt like forever, the last bit of seed trickled out of her tip, her balls emptied and her cock slowly going flaccid. She breathed into Alex’s ear, as the boy simply laid there, his head resting against her thick, white braid running over her shoulder. With a soft chuckle, she gave him a wet smooch on his cheek.
“That wasn’t so bad, was it?” she murmured. “Admit that it felt good.”
“Fuck you,” Alex spat.
“Language, young man,” she tutted. “Well, you’ll like it eventually. Now, there’s a bathroom over there, I want you to go take a shower, get yourself ready for some new clothing.” She pointed at the door next to the bed. Then, she helped him get up, lifting him under his arms as her flaccid shaft fell out of his asshole, landing on her thigh with a wet thud.
She gave him a light push on his back, prodding him to be on his way. “When you get back, you have more work to do.”
With hesitant steps he made his way to the large mahogany door, forming a trail of cum as it leaked out of his ass, swung the door open and quickly closed it behind him. He left the lights turned off, leaned his back against the door and slid down onto the floor. Tears welled up in his eyes, but he did his best to not make audible sobs.
He knew that Evelyn was right. There was nothing he could do about his situation. He couldn’t even quit the job, he had already agreed to stay over the summer. Was there no way out? Did he have to be her slave for ten whole weeks?