A Witch's Grasp Ch. 02

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Alex begins his humiliating training at the hands of Evelyn.
11.3k words
4.67
34.5k
95

Part 2 of the 2 part series

Updated 06/09/2023
Created 05/10/2019
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Author's note: This chapter was meant to reveal more about Evelyn's character, but I decided to save that for the next one since I had already reached 11k words. But hey, that means that I'm already 2k words into chapter 3!

Anyway, enjoy!

*****

"Why do I have to wear this?!" Alex complained, his face red from embarrassment and his teeth clenched in anger.

Across the desk, Evelyn sat on her chair, smiling from ear to ear with her hands on her cheeks. "Why are you complaining? You look so adorable!"

"I look like a... a girl!" he said, pulling on the skirt of his black and wait maid outfit in an attempt to conceal his smooth, exposed thighs.

"No, no, no..." the old woman countered. "You look evenmore like a girl." Evelyn, who had similarly taken a shower after their initial sex-session, was dressed only in a white bathrobe, tied tightly around her waist and somehow preserving her gorgeous hourglass figure despite the thick, loose fabric. The two braids that had hung over her chest before had been undone, her wavy, silver hair now cascading freely down her back instead.

Alex looked at her with resentment as she just continued to grin at him lustfully, disgusted at how she felt no shame over having raped him moments ago. Even now, however, she managed to look stunning. It didn't help that she was showing off her tits in a massive cleavage, making him unable to keep her eyes off her, despite the intense anger he felt towards her.

"Now then, Alex," she continued, standing up straight and stretching a bit. "It's getting late. Did you brush your teeth, like I told you to?"

Alex sighed. "Yes..."

"Good. Then let's go to bed, shall we?"

"... So you can rape me again?" Alex spat, staring daggers at Evelyn. His words only seemed to make the dull ache that remained in his asshole even worse.

She tilted her head at him, trying to put on a comforting smile. "No, sweetie," she said. "You need rest. There's a big day ahead of you, lots of work to do."

"What kind of work?" He watched as Evelyn's smile grew wider, while she simultaneously rose from her chair and made her way over to him. Trying his best not to flinch, he merely stood there as she reached out with an extended index finger, with which she proceeded to lift up his chin.

"I'll just put it like this..." she purred, running her wet tongue over her lips as she stared him down. "I'm just as horny these days as I was fifty years ago..."

Alex frowned and looked away. "You're sick..."

"Maybe a little," Evelyn giggled. "But I have a sweet side too. Here, let me carry you to bed, cutie."

"Hey!" Alex protested, as Evelyn's old, yet sturdy arms pulled him in towards her, after which he was lifted up into the air. Without any chance of resisting, his chest was promptly pressed against her massive tits, and as he grabbed her around the shoulders for support, the tall, old woman took the opportunity to gently wrap her hand around the back of his head and use it to align her cheek with his, much like a mother would lovingly hug her young child.

"Shh-shh-shh," she hushed, making her way to the huge, mahogany bed in the corner of the room. "Just calm down... Grandma's gonna tuck you in real good..."

As much as he wanted to keep protesting, Alex was immediately stunned by the sudden intimacy, not to mention Evelyn's scent. She smelledso good... Sweet, clean and fresh, and with just enough of her own natural, mature aroma mixed in with it to produce a scent that just screamedwoman. Somehow it actually did calm him down, almost as if Evelyn had foreseen that it would.

She put him down on the floor right next to the bed, before quickly moving on to sliding the maid outfit down his shoulders, while he merely remained completely still, embarrassed and angry. Soon enough she had worked herself down to his skirt, which she likewise slid down his legs along with the rest of the dress, until she was presented with his sexy, almost naked body. The only thing left were his white, knee-high socks and black shoes.

"Sit down, sweetheart," she said, gently pushing her palm against his chest. The boy fell on his butt onto the bed, seemingly too tired to resist. Once sitting, Evelyn extended his legs one by one, removing the remainder of his clothing. She eyed him for a moment, taking in his girly curves and his tiny dick with a grin on her face, before coming to her senses. "There we go. Now get comfy while I undress."

Without a word, Alex turned away from her and reluctantly crawled underneath the cover. He could hear Evelyn softly sauntering around the bed, along with the sound of her belt being undone, followed by the bathrobe as a whole. He knew in that moment that if he turned around, he would be greeted with a view that would be forever imprinted into the back of his mind, one that could shatter his long-established idea of the perfect woman. He hated himself for thinking along those lines, but he couldn't help it. Evelynwas beautiful. 68 years old, gray-haired, breasts with more sagging than any girl closer to Alex's age, a modest, yet noticeable amount of wrinkles and moles here and there... Indeed, it didn't sound all that great on paper, and yet she had somehow made it work. If only it weren't for that massive cock and balls between her legs...

Alex could feel her lifting up the other end of the cover, after which the weight of her body on top of the mattress became apparent as she climbed onto the bed. He braced himself as she crawled closer, tucking both of them in under the cover, leaving his naked body defenseless against hers. Soon enough he could feel her fat tits pressed against his back, followed by the rest of her body lining up with his, her flaccid, yet still huge cock pressed against his butt.

Evelyn placed her hand on Alex's arm, feeling the boy start to shiver from her touch. "There, there..." she soothed, softly kissing his cheek and ear, her hand now making circular, massaging motions as it traveled all over his upper body. Little by little, she could feel him calming down, his body coming to be still as she continued to kiss and touch him. "Just close your eyes, Alex... I know you're getting sleepy..."

"I probably won't get much sleep next to you," he grumbled in response.

Evelyn chuckled. "You can't fool me," she said, pulling him in even tighter against her soft body. "I can tell just from touching you... You feel relaxed, don't you? As if all the tension in your body is gone?"

Truth be told, hedid feel it... literally all over his body. His skin was all tingly and warm, his muscles were limp, and his legs felt like they had been reduced to spaghetti. And even in that moment, next to the woman who had defiled him moments ago, he felt as if he could fall asleep at any second, out of comfort rather than exhaustion.

"That's the effect my big, fat cock has on you..." Evelyn whispered in his ear. "And you're going to experience it over and over again... until you can no longer sleep without a dose of my warm seed..."

"Th-that will never happen...!" Alex protested with his last bit of energy, blushing and sweating nervously.

Evelyn giggled, her right hand gently massaging the boy's chest. "We'll see. Now, give grandma a goodnight kiss..."

Alex could see the old woman's ever so slightly wrinkled lips in the corner of his eye, pouting as they awaited reciprocation, making ammm-sound in the process. There was no way she was ever going to give up, he knew that much. Being forced into sexual acts was one thing, but meeting her halfway was a big mental obstacle to overcome. Perhaps it was best to just get it over with...

Swallowing his pride and hatred, he turned towards her and as quickly as he could pushed his lips against hers, hoping to be able to satisfy her with an innocent little peck... but Evelyn was prepared for that. The moment they connected, she grabbed on to both of his cheeks, holding him in place as she practically sucked his smaller lips into her mouth, her tongue emerging like a snake from a cave, filling up his oral cavity within an instant. They both moaned as the kissed dragged on, Alex with panic and Evelyn with lust, as her tongue swirled around his, dominating it like it was nothing.

Alex cursed himself internally, telling himself that he should have seen this coming. But with that said, it should be noted that the fact that Evelyn was an amazing kisser made it all a lot more bearable. Furthermore, not only did she smell great, she tasted even better. She was forcing him to swallow her saliva over and over, simply because the amount that flowed into his mouth had nowhere else to go than down his gullet.

Finally, she pulled back, leaving several strings of drool between them. "Aah..." she moaned, wiping off her smiling mouth with the back of her hand. "I think we both needed that... Wouldn't you agree?"

Alex turned away, going back to lying on his side. "Mhm, sure..." he muttered, a strong blush on his face.

"Thought so," Evelyn teased. "Goodnight, sweetheart." She lay down next to him, her face right behind the back of his head, and her arm draped around his chest.

"Goodnight..." No longer even having the energy to add a sarcastic tone to his words, Alex felt his eyelids getting heavier and heavier. At long last, he closed his eyes and began to drift away, praying that his hatred would remain as strong the next morning.

----------

As if no longer than a second had passed, Alex's eyes shot open, his surroundings lit up by the morning sun and his ears filled with the songs of the various species of birds that inhabited the massive, flower-clad garden outside. He looked around, slowly remembering the day before, but just before he had the chance to get pissed off, he realized that he was alone. His tormentor was no longer in the bed with him, not by the desk in the center of the room, not by the lounging area, and judging from the fact that the bathroom door was open and the ceiling light within being turned off, she wasn't there either.

He threw the cover away and sat up on the edge of the bed, casting his glance towards the nightstand next to the bed, over which his maid outfit was draped. On top of it stood a piece of folded paper with words written on it. He reached out to it, picking the paper up and read it, confused as to what could be going on.

It read:

*****

Sweet Alex,

I completely forgot that I had a meeting planned for today. I will not be able to spend any time with you until later this afternoon. Until then, please follow the instructions listed below.

Have some breakfast! I left a little basket for you by the lounging area. There's sure to be something in there that you find tasty, but keep your figure in mind! Place the basket in the little fridge by my desk afterwards.

Take a shower and brush your teeth like the good boy you are.

Put on your cute little outfit! I can't wait to see you in it again...

Down the hall to the right, past the door at the far end of the corridor, you will find Clara's office. Go to her for further duties. Don't worry, it's not going to be anything difficult.

That's it for today. I'll see you later. Also, make sure to mentally prepare yourself for when I get home... I'll be teaching you how to work your pretty lips around grandma's big...

... fat...

... cock...

*****

Those final lines had Alex visibly cringing. He still couldn't get over how a woman of her age and status could so easily act like such a sleazebag. But hey, at least he didn't have to drink her cum for breakfast. And while he didn't know much about Clara, she couldn't possibly have something worse planned for him than Evelyn.

Still in the nude, he made his way over to the lounging area, finding the little basket next to one of the sofas. He placed it on top of the table in the middle and immediately began looking through it for something to sate his rumbling tummy. And just like Evelyn had presumed, there was no shortage of foods that he enjoyed in there. Cereal, bread, marmelade, milk, chocolate milk, coffee, donuts, cheese... hell, there was even a plate of what appeared to be shredded rotisserie chicken. Back at home, he would have been lucky to afford even two of the food items that stood before him at the same time, and now he was free to indulge in whatever he wanted. The meeting with Clara might have to wait a bit...

----------

Walking in heels proved to be quite difficult for poor Alex. With a belly full of food and freshly out of the shower, each wobbly step he took down the hallway required total concentration, and he prayed that he wouldn't fall over completely in front of Clara. Being forced to dress like a maid was humiliating enough, but to be seen by her made the whole thing a million times worse. Especially considering that the only interaction they had previously had was a quick introduction.

Nevertheless, he stumbled onward to the door that Evelyn had referred to, stopping in front of it and taking a deep breath. With a shaky hand, he opened the door, slowly pushing it open to reveal the office where Clara managed Evelyn's business. Whatever that business was. Like the rest of the house, it was fancy and expensive-looking, its walls adorned with elegant paintings, and the furniture all made of mahogany. It was a bit cramped perhaps, but for just one person it wasn't that bad. Clara sat behind a desk at the opposite side of the room, her outline almost entirely covered by a large computer screen. She must have been completely engrossed in her work, her red-painted lips wrapped around a pen as she mindlessly chewed on it, not even noticing Alex's presence. That is, until he let out a light cough to get her attention.

She looked up, meeting the embarrassed, blushing boy's gaze with a smile on her face. "There you are!" she said. "Took you long enough."

Alex closed the door behind him, but remained in place. "Sorry..."

"No problem, there's no such thing as stressing in this household." The business suit-clad, black-haired beauty stared at him, noting how perfectly he fit into the cute dress Evelyn had given him. "I see you've already been properly outfitted."

Alex looked down at the floor, the blush on his face showing no sign of diminishing. "Laugh all you want... I don't care."

"I'm not gonna laugh at you," Clara assured him, the tone of her voice indicating that she was being genuine. "I was just thinking that you look good like that. Ms. King probably loves it."

"... You knew about all this, didn't you?" Alex fired back. "About what she would do to me?"

Clara's smile died out. "... I did."

"Why...?" Alex pressed, voice quivering and hands clenched at his sides. "Why would you let this happen?"

"Alex..." Clara began, getting up from her seat and walking over to him. She knelt down in front of him, trying to look into his eyes that were still aimed at the floor, but as expected, he immediately avoided her. "Look... I know you're feeling miserable right now, but I-"

"Miserable...?" he interrupted, close to tears from the sound of it. "Miserable doesn't even begin to describe it... She fucking raped me, Clara... And now I'm stuck here..."

"I know. I'm sorry it has to be this way, but when it comes to her, there is little choice."

"... Why?"

Clara cleared her throat. "It's... complicated," she said. "But as for my reasoning, I did it partly for her sake, and partly because I'm convinced that, in time, you will come to terms with it. Probably even enjoy it."

"'Enjoy it'?" Alex replied, clearly offended. "What makes you think that?"

"Well, I mean..." Clara began, searching for the right words. "... I'm not gonna try to justify what happened to you, but let me just ask you this: Physically speaking, did you not feel at leastsome pleasure?"

Alex finally looked back at her, but with pure vitriol in his eyes. "... What the fuck is wrong with you?" he seethed, the high-pitched, androgynous tone of his voice making itself even clearer. "Why does that matter at all?" In his rage, he couldn't help but find it kind of strange how Clara seemed to know so much about the ugly side of Evelyn. Had she been a victim as well?

"Hey, calm down..." she soothed, her hand reaching out to grab Alex's hand, which he immediately pulled away. "I was just thinking that... even if you're forced to be in Ms. King's company against your will throughout the day, then maybe you can at least find it somewhat enjoyable to sleep with her? You know, something to look forward to?"

"No!" Alex protested. "I would never look forward to being humiliated like that! And I'm straight, for fuck's sake! I don't like dicks!"

Clara shrugged. "Maybe not yet..."

Alex did his very best to hold back the urge to punch her in the face. "Go fuck yourself," he growled.

"Listen..." Clara began and took a deep breath. "I know how wrong this sounds, but whenever Ms. King makes you sleep with her in the future, try to find enjoyment in it. Regardless of how much you hate her, regardless of how humiliating it might be to be taken by force, try to put aside your feelings just for the moment and go into it with an open mind. Focus on how it feels, physically. I can almost guarantee that she can give you more pleasure than you could ever imagine."

Alex shook his head in protest. "None of that shit matters," he grumbled. "Pleasure doesn't mean anything when it's accompanied by a horrible person like her."

"She's not a bad person," Clara dismissed without hesitation. "Trust me, if you knew her story, you would understand. At least a little bit."

"What's her story, then?"

"You should ask her instead of me," she said, standing back up. "I'm sure she'll tell you everything you need to know. Until then, you have some work to do."

With a sigh, Alex wiped away the tears that had gathered in the corners of his eyes. "... Whatever. What do you want me to do?"

"Here," she replied, handing him a note with instructions written on it. She had made sure not to include anything difficult for the boy's first day. After all, his main duty was taking care of Evelyn's sexual needs. "I used to take care of most of this stuff before I got promoted, so if you have any questions, feel free to ask me. Do them in the order they are listed in, then come back to my office. Okay?"

"Mhm..." Alex mumbled unenthusiastically in response. "Can I go now?"

"Yeah, you're free to get started. You should have a lot of time before Ms. King comes back, so there's no need to stress, by the way."

The sullen boy nodded. Without a word, he turned around and stepped out into the hallway, slamming the door shut behind him without any regard for its structural integrity. Heading back to whence he came, he hung his head low as his legs once again started wobbling as a result of the high-heels that he was forced to walk in.

Clara sighed with relief as she went back to her computer. While it might have seemed to others that there was reason to worry about how emotionally stable the new recruit was, she wasn't bothered by it. Because to her, one thing stood out in the conversation that had just taken place: Alex never denied the suggestion that he had felt pleasure during his sex session with Evelyn. That was all it took for Clara to know that he was the one... and that thought brought a smile to her face...

In contrast, Alex frowned as he read the instructions he had been given. "'Make the bed'..." he mumbled to himself. "'Water the office flowers, tidy up the desk, turn on bathwater'..." The tasks, while easy enough, made him feel conflicted. Sure, they didn't evolve a massive, old lady-cock entering any of his orifices, but they were so... lame. His hopes for what his new job would pertain had not been high to begin with, but the fact that the only thing that was different from what he initially had in mind was that he would be getting raped in addition to his boring tasks was depressing to say the least.