Harem Master - RPG story

--- Asher Montgomery ---

"Thanks, Maddy," Asher said.

After she had cried and calmed down a bit, he wanted to distract her by studying together.

She smiled sadly. "I should be the one to thank you. You missed the lecture because of me," she added, glancing down at her hands folded on her knees.

"I'm glad I could help," Asher replied. "And thanks to you, I learned it all anyway."

"You've probably already forgotten half of it."

"Oh? Is that how little you believe in me?" Asher asked, feigning shock.

Maddy just shook her head, smiling softly.

Asher snorted. "Well, I'll surprise you. You'll see. But now I really need to go. I have to prepare for our exploration. And I've got a meeting with Rachel."

"To talk about your class?" Madelyn asked quietly, averting her gaze.

Asher grunted, his cheeks flushing. "Yeah," he replied. If only she knew what that meeting was really about... she'd be shocked.

"Be careful in a dungeon," Madelyn said, changing the subject.

"Of course," he replied, stepping toward the door.

"Ash..." Maddy stopped him.

"Yeah?" he asked, turning back with one hand on the door handle.

"Thank you," Madelyn said, looking him in the eyes.

"No problem. That's what friends are for," he replied, before leaving her room.

During their studying Madelyn had been distracted, sad and closed even more than usual. He hoped his presence helped at least a tiny bit, but he had no idea how to truly help her. Asher wondered what options he had, but nothing could turn back time and erase what had happened to her.

He could only stay with her in those dark moments and encourage her to move forward. But would he have time for her? With his harem he had five women he would need to spend time with daily, both to gather experience, and because of relationships growing between them.

How would he manage all of that? How would he find time for everyone? How was he going to make every one of them feel special and appreciated? How would he make sure that they don't feel neglected?

Asher had no answers to any of his doubts, but his reflections were stopped when he reached Rachel's room.

"Sit," the teacher said, pointing at the chair by the table.

As she moved to sit on the other side, he looked over her body. Her outfit was surprisingly conservative for her. A long skirt reached past her knees, and her shirt was buttoned all the way up to her neck, leaving not even a hint of cleavage. Her brown hair was tied back in a ponytail, and she wore glasses that completed the look of the teacher. Not the erotic fantasy of teenage boys, but the one who actually dressed professionally for the job.

"So, what brings you to me today?" Rachel asked.

"Umm..." Asher hesitated. It was obvious, and they both knew why he was there. "We were supposed to talk and... you know."

"Mhm. So, what is it you want to talk about?"

Asher sighed, confused by her behavior, but focused again on the worries he had had just moments before. "I don't think I'll have enough time for everyone in the harem. I'm already going from one woman to another all the time. I have zero time for myself... Well, that's not a tragedy. But what if, for example, Naomi will want to spend more time together?" he asked.

"I might not have it for her," he continued. "Ava's behavior confused me. Lucy wants something more. And there are always other things that just happen in life and you can't predict them. How am I going to manage all of that?"

Rachel smiled softly, watching him. "Ah, problems of Harem Master. Too much women's attention and sex in his life."

"That's not what I mean," Asher said. "I'm not complaining. It's all amazing... For me. What if I don't have time for them? What if I won't be able to make them as happy as I am?"

Rachel drummed her fingers on the table, thinking it over.

"You're the Harem Master, a central part of this team in a way, but you need to remember that these women have their own lives. You're not responsible for their happiness. Not everything is about you and they don't need you around all the time," Rachel said.

"Elara trains a lot," she continued. "Naomi studies. When Ava would get obsessed with something new, she'd barely have time for anything else. Lucy'll always have something to keep herself busy, whether you're there or not. And they've got each other, too."

"What if something happens, and they need me? And I couldn't be there because I am with someone else?"

"Fortunately, they know about each other," Rachel replied.

Asher sighed. He knew they wouldn't need him around all the time. But two hours every day? That added up to ten for him. With eight hours of sleep, that would leave him with just four.

On a day without exploration? Possible.

But on a day when they explore? After spending six, seven, even eight hours in a dungeon? There was no way he could give each of them that much time.

"And," Rachel added. "You're going to live with them. That'll give you plenty of time to spend together."

This didn't kill the doubts about his limited time and women in his harem.

"You can also try to think of activities where you would spend time together," Rachel suggested. "Besides dungeoning. Then you would spend time with all of them at once."

"That might help," he sighed.

"It's good that you're thinking about things like that, but maybe it'll never even be a problem. Don't stress too much about it. No one really knows how this whole thing is going to work. You just have to wait and in the meantime, you can make an effort to spend time with everyone. And talk with them, to make sure everything's going well."

"Maybe you're right," Asher murmured.

"Is that why you skipped a lecture today?" Rachel asked. "Sex was more important?"

Asher hesitated, wondering if this was the cause of her weird behavior and she was mad at him.

"No," he protested. "I was with Madelyn, studying. Besides, Elara had her training session with Maya at seven, so we took care of... things earlier," Asher explained.

"Is there something wrong with the teachers at the Academy?" Rachel asked.

"No... Madelyn wasn't feeling well, and she skipped the lecture. I wanted to check on her and ended up staying to study. I didn't want her to be alone."

"Oh," Rachel said, her expression quickly changing to concern. "Is she okay?"

"Yeah, she's fine."

"She told you about whatever is bothering her, didn't she?" Rachel asked.

"We talked," Asher replied. Even if Rachel could somehow help Madelyn, it wasn't his decision to tell the teacher about her situation.

"That's why you're worried you won't have time for everyone," she said.

"More or less."

"Let's say I consider that a good enough reason to skip the lecture, but you really should attend them," Rachel said.

"I do, unless something else comes up."

"As long as it's not sex that stops you," Rachel said.

Asher nodded without answering.

"Is there something else that brings you here today?" Rachel asked.

"Well... we need to prepare before a dungeon," Asher replied.

"Okay," Rachel said. "Do you want to go over monsters you can meet there?" she asked.

"You're teasing me," Asher commented, when he noticed her soft smile.

"I'm not sure what you're talking about, young man."

"Rachel, stop."

"Speaking to your teacher like that? Maybe I should teach you some respect for your elders."

"Didn't you say you're not that much older?" Asher asked.

"I don't recall saying anything like that," Rachel said.

"Well, at your age, that doesn't surprise me," he shot back.

Rachel gasped. "Oh, now you're pushing it," she said, but was smiling.

"So, Miss, would you help me with preparations?" Asher asked.

"That depends. What could you possibly need from an old teacher like me?"

Asher hesitated for a moment, getting flustered when he was supposed to tell her that they needed to fuck, but then an idea came to his mind.

"It's about my class, Miss. It's... really weird, but I hope you could help me with it."

"Of course," Rachel replied, smiling.

"Have you ever heard about a class that is connected to... sex?"

"That sounds... strange. How is it connected to sex?" Rachel leaned forward, supporting herself on the table between them.

"Some of my skills need... sexual activities to work."

Rachel got up and slowly walked toward him, brushing her fingers along the table. "Activities... Can you give me an example?" She sat next to him, shifting so close, their thighs brushed and he could see details of her eyes from up close.

"It starts with kissing," Asher replied.

"You need to kiss me? So I could help you with your class?" Rachel leaned toward him with a glint of excitement in her eyes and running her tongue over her red, plump lips.

A week earlier, when they had a similar conversation and she had been leaning toward Asher the same way, he had shifted back and, like an idiot, fell from his chair. This time he knew that things were going to be different.

"That would be a good start," he said, before leaning forward and connecting their lips. They moved slowly, caressing each other in a long and tender kiss.

"Oh my," Rachel gasped when Asher put his hand on her chest and squeezed her large tits through her shirt. "Someone's gotten a lot bolder after just one week."

"It's for... you know, my class," Asher whispered, lowering his gaze, as if embarrassed, but his hand still kneaded her tits.

"Well... It's my job to explore the possibilities of your class with you," Rachel replied, smirking.

"Thank you, Miss," he said, squeezing her tits, her hardening nipples poking through the material of her shirt and bra.

"Anything for my students," Rachel whispered.

"Anything?" Asher asked, placing a second hand on her tits, groping both of them.

"I want to help them become the best explorers," Rachel replied, pressing her chest further into his hands.

"There's something else that would really help me, Miss."

"What is it?"

"My class would work better if you... took off your clothes," Asher whispered.

"What a strange class," Rachel mused. "But I knew that teaching requires sacrifices." Leaning back, away from his hands, she slowly unbuttoned her shirt, her fingers gradually exposing her amazing body to his hungry eyes.

First her upper chest and collarbones, the start of her cleavage, her plain white bra that supported her large tits, and her soft stomach, as she took off her shirt. "I guess the bra is going to interrupt your class too?" Rachel asked, but even before he could answer, she unclasped it and pulled it off her arms.

Freed from the bra, her tits barely sagged, standing firm despite their impressive size. Her hard nipples pointed straight at Asher, and he couldn't stop his hands - he grabbed both mounds, squeezing the warm flesh as his thumbs brushed over her stiff buds.

When he pinched them, Rachel gasped, parting her red lips, letting him enjoy her body for a moment while she savored his hands on her tits and the way his hungry gaze was fixed entirely on her, like nothing else in the world mattered anymore.

"Tell me about your skill," Rachel whispered. "I need to understand how this strange class works and make sure you're not taking advantage of your naive teacher."

Asher hummed, fondling her naked tits, playing with their weight, soft flesh, and hard nipples. "It's a really strange class, Miss."

"Don't be shy," Rachel said.

Asher snorted, dropping the act. With his hands squeezing her tits, he was anything but shy. Rachel smirked too but let out a soft moan when he pinched her nipples.

"I get experience points from... this," he said.

"Really?" Rachel asked. "From playing with your teacher's tits? That's quite specific."

"Oh, there are other options too," he said, looking from her tits to her face, focusing on her lips.

"Oh? I can help even more?" she asked with a playful grin.

"In so many ways."

"Tell me about them."

"We could... kiss. But that's not my only skill."

"Tell me about all of them."

"I can borrow a skill from you for my exploration today."

"That's amazing," Rachel gasped. "Go on," she added with a smirk, pushing her chest forward. "Use it. You can take anything you need from me."

"That's not so simple, Miss. It has... a sexual requirement."

"I don't know," Rachel murmured. "Haven't we already pushed things too far?"

"Miss, this class is so strange. Only you can help me," Asher said, pretending to be worried. As much as their little game was fun, his hard cock was straining in his pants, getting uncomfortable.

"Okay. Okay, I'll help you," Rachel replied. "But you must tell me what you need from me."

"I think it would be easier to show," Asher said.

"I'm showing you a lot already," she said, smirking and shaking her tits. "Maybe you should show me something too," she added, glancing down at the bulge in his pants.

"Interesting idea," Asher said, getting up. "But we should move somewhere more comfortable," he added, looking around the room, pretending to consider their options. "Oh, I think the bed would be the best."

"The bed?" Rachel asked. "Your class is really strange." She got up and followed him to her own bed.

"I know, Miss. It's amazing that I have your help."

"That's my job here," she said.

Asher gently pushed her onto the bed, and she shifted further to lie comfortably. He followed after, straddling her and hovering over her body.

"Oh my," Rachel gasped. "What are you doing?"

"It's all for my class, Miss."

"Well... if it's for your class, we don't have a choice then."

"We really don't," Asher murmured. Leaning forward he kissed Rachel - their lips meeting in a passionate embrace. He pushed his tongue into her mouth gently, and put his hands on her tits, squeezing them again.

Grinding his body against hers, he slid his hands lower to the hem of her skirt. Still kissing her, he began to tug it down.

Rachel wiggled her hips, helping him remove it completely.

Tossing it aside, Asher shifted to her side, and looked at her completely naked body, as she didn't wear any underwear.

"Was getting me naked a requirement of your class?" Rachel asked.

"It's almost like you could read my status."

"What about you? Shouldn't you take off your clothes too? I think that would help."

"Oh, stupid me. You're right, Miss," Asher said with a smirk. After his clothes hit the floor, he grabbed her legs and spread them apart.

Arousal glistened on her pussy lips and thighs - proof that all the foreplay had left her more than ready for his cock.

Leaning forward, he connected their lips in another long kiss. As his dick brushed against her folds, both of them moaned into their connected mouths. Reaching between their bodies, he grabbed his shaft and aligned himself with her pussy, pushing his length into her.

With how slick she was, he easily slipped in with one thrust. His hips met her body as her drenched pussy wrapped around his manhood.

"Fuck," he murmured, lying on top of her, tits pressing into his chest, hands wandering over his back and shoulders, as he savored her insides squeezing him.

Rachel slowly stroked the nape of his neck, sending pleasant tingling along his spine that was met and mixed with the pleasure that her pussy caused, massaging his shaft.

"Does it help you with your class?" Rachel whispered.

"Yeah," Asher gasped. Reminded of what he was actually supposed to do, he activated his skill and borrowed the Crippling Curse from Rachel. It would allow him to slow down monsters in a dungeon.

"But I need more," he said, pulling his cock slowly out of her body, to then push it quickly back inside her. He kissed her passionately while working his hips faster, her wetness sloshing as he fucked her quickly.

Despite their lips connected in a deep kiss, quiet moans were flowing between their mouths. Rachel was clenching her pussy around his shaft every time their bodies met, and his cock was fully inside, and the amazing sensations of her insides rubbing all his sensitive spots were pushing him quickly toward his orgasm.

"I'm close," he gasped.

"No," Rachel whimpered. "More, please," she moaned.

Asher bit his lip hard, trying to stop himself for just a little bit longer while still working his hips. All this talking and teasing had aroused him too much.

"Don't stop, please," Rachel gasped. "I'm close," she added, pushing her hips into him, making their bodies meet in even harder thrusts. Her pussy clenched around his length as he pushed in and out from between her folds. The pressure in his balls was boiling, getting to the point that he wouldn't be able to hold himself back anymore.

"Fuck!" he gasped when it finally tipped over. Squeezing Rachel's tits, he still made short, quick thrusts as cum erupted from his cock into her clenching pussy.

Rachel cried out loudly, her body stiffened and her lips remained parted wide. She froze in a display of pleasure, and Asher's cock throbbed victoriously in her pussy that clenched tightly in orgasmic spasms.

Glad that he was able to make her come along with him, Asher rested on top of her soft, squishy tits, brushing his lips against a soft skin of her neck as they both remained lost in the pleasure.

Even after the bliss faded and Rachel relaxed beneath him, he stayed lying on top of her, with his cock still buried deep between her folds.

After his breath calmed down, he finally shifted to the side. His soft cock slipped out of her drenched pussy filled with his load. Lying on his back, he quickly checked Rachel's status. She had gone from 31% at level five to 84%.

Rachel rested her head on his chest, snuggling close.

Asher wrapped his arm around her and squeezed her ass softly. He checked her status again, confirming they had reached the experience limit.

Lying in his teacher's bed, her naked body pressed into him after they'd just had sex, Asher couldn't help but reflect on how strange his life had become. Rachel was over ten years older. He had just come inside her raw. And on top of that, his girlfriend was completely okay with it.

Well... "completely" might've been overstating it, he admitted to himself. Elara knew, and she was still trying to come to terms with it.

"I thought you were angry at me for skipping class, and that was why you behaved weird," Asher said to Rachel, still squeezing her ass.

"I wasn't mad," Rachel replied. "And I wasn't exactly happy either. But I was curious how you'd seduce me."

He leaned forward and connected their lips in a brief kiss. "It was amazing, but..." he trailed off.

"You need to show your strange class to other women?" Rachel asked.

"Yeah, something like that."

"Be careful in a dungeon," Rachel said, pecking his lips.

"I will," he said, holding back the comment that she was repeating herself. He just accepted that she was worried about her students.

Rachel stayed in bed, watching as he got dressed.

Before leaving, he looked one last time at her amazing body flushed after sex.

But as he stepped out, he was already thinking about the next woman.

--- Elara River ---

Elara was pacing around her room, waiting for Lucy to come over for a talk. She was thinking over everything she wanted to bring up, and not cause an argument at the same time. She hoped to explain everything between women, without getting Asher involved.

It seemed like they were finally settling into this fucked-up harem situation, and Elara didn't want to ruin it. She didn't want to be the negative one again, the one always causing problems.

When Lucy knocked and Elara invited her in, the pink-haired girl threw herself at Elara, who shifted her head away so they didn't kiss, and only hugged.

"Oh, I hoped for a welcome kiss," Lucy said, pouting. "Oh," she said when she noticed Elara's expression and backed off.