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Chapter 37
by Vox121
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Emma's Quest (Alternate)
Note: This branch is the direction I was originally going to take and does not match the later chapters. I am releasing these chapters for those who liked the harsher elements of Emma's game. Be warned, they are unedited and are first draft, so there will be errors. The other branch is the canon path, so while both branches arrive at more or less the same place, if this is your first time reading the story, go back to the previous chapter and go through the other path first.
Emma didn’t show up to the session. Wasn’t expecting her to either. My texts went unanswered and when I tried to call, she sent it to voicemail.
The session turned out to be a bust. Not much got done. Owen and Ben especially seemed lost. Her absence made me realize how much she had integrated into the group. I could see it in the others too.
I called it early. Our focus was on other things and no one seemed to have any energy.
It hurt seeing how important she had become. If she decided that was it and was going her separate way, our group would never be the same. The depressing thing was that I felt okay with that. We’d been together for around four years now and besides Mike, I was **** to face the truth that our relationship was never all that deep. Sure, we had some similar interests and stuff, but Owen was an asshole. Ben was fine, but we never really connected beyond the group setting. Trent… was Trent. Even after four years I barely knew anything about him.
Misfits who banded together by necessity rather than deep bonds. We’d been fine before because there was nothing to measure it against. Emma had brought an energy that none of us could replicate. Her presence changed the group as much as she had changed me.
And seeing the impact she made pissed me off. Not because of the changes, but because of how embedded she was in my life. Not even my friend group, outcasts by pretty much every measure, was spared. Without me even realizing it, she touched nearly everything in my life in some way.
Yet what impact did I have on her life? Removing her from my life was like pulling a plant up by the roots and tossing it aside. Would she even notice my absence?
Scrolling through some manga I was following, I ignored the doorbell. It was Sunday and the last thing I wanted was to deal with some salesperson or missionary pushing their church on me. I’d let mom or dad deal with that.
So the soft knock at my door made me jump as I spun around. The door wasn’t closed, so it was a bit odd for there to be a knock. Usually, my parents would just call down if they needed me. Seeing Emma standing there was the last thing I expected. Friday hadn’t ended well and she’d blown me off completely yesterday.
She had a soft smile as she stood in the doorway. “Kinda disappointed I didn’t catch you at a bad time.”
“What are you doing here?” I didn’t mean to sound so harsh, but I think I was still angry after yesterday. Friday had been bad, but to completely ignore me? What truly pissed me off was my first reaction to seeing her was to release the anger I was holding against her for that.
The cute smile faded. “To apologize. My behavior on Friday and yesterday was… not good.” For someone who seemed to be a master wordsmith at times, she was struggling now. “You were right. I am not in a position to dictate who you spend your time with or what you do with them. I… got lost in it.”
“In what?”
“Our game. At the end of the day, that’s all it is: a game.”
A game. Right. That's all my feelings would ever amount to. Another piece to manipulate.
Running a hand over my face, I sighed. “It’s… fine. Apology accepted.” And like that, I once more set the piece upright. The piece she would knock over. Again and again.
She didn’t say anything more, awkwardly standing there. I let the silence fester. I wasn’t in the mood to **** things.
“Do you regret it?”
“Huh?”
Her gaze went to my bed and memories flooded me. The feeling of her legs on either side of me. The look on her face as she waited for me to take what I wanted. The wetness on my finger as I touched her in a way I never thought I would.
“Oh.” Did I regret not sleeping with her? I had been crushing on Emma practically since we met and I was right there. Right there. But my uncomfortable conversation with Ryan put some perspective on things as well as the event that sparked this whole thing. I wasn’t the sort of guy who could walk that path. Emma’s friends were all attractive in their unique ways and I would be the first to admit I got sucked into the moment. The confidence boost of having seven hot girls offer themselves to you was a hell of a thing. Thinking back though, I never wanted to actually sleep with any of them. The only reason I said what I did was to tease Emma.
Emma.
It always circled around to Emma.
“No,” I answered with a sigh. “Did I want to? More than anything. Stopping was one of the hardest things I’ve ever done. Regret it? No.” My eyes met hers as she looked down at me in my chair. “You were right. I’m not the casual sex kinda guy. Do I want to have sex? Yeah. Pretty damn bad too. Like… really bad. You haven’t exactly made it easy for me.”
“You know any of the girls would be more than happy to help you with that.” I felt my eyebrows rise at that. She shrugged. “You’re a friend of a friend. Even without that, a few of them enjoy taking guys’ first time. I prefer a more experienced hand myself but to each their own.”
I let the last part of her sentence roll past. “Would you be okay with that?”
“I’m in no position to stop you.”
“Didn’t answer my question.”
She didn’t look at me. “I would be lying if I said yes.”
“Which leads us right back to square one: My feelings keep pushing me to make something more of this than you want, and your selfishness keeping me at arm's length.”
Moving over to my bed, she ran her hands over her skirt before sitting. Her voice was soft as she spoke. “I spent most of yesterday talking with Sarah and Emily about this. All this, you, it’s not really in my skill set.” She brushed at her hair before realizing what she was doing. Looking toward her lap she rested her hands there. “I know there is something off with me. It’s never been a big deal though. I’m content with life. I love my sister and dad. I have great friends who, along with my family, give me plenty of support and social fulfillment. Basically, all my needs are filled. Socially, emotionally, mentally, physically, sexually, I have no complaints.” There was a pause and she took a deep breath. “I have never felt compelled to be in a romantic relationship. Guys have asked before. Guys I considered friends and had emotional investments into. Like you, I turned them down because it never interested me. They simply offered nothing more than what I already have. Then you came along.”
She looked up at me.
“A lot of this is thanks to Sarah and Emily spending hours helping me untangle this, so I hope it all makes sense. You are… special—but not in the way you are hoping for.” She pulled in air through her nose and made sure I was paying attention. Not that she needed to. I clung to every word she said. “I like you, Isaac. There is no denying that. I like you more than I thought I could like someone. There is a unique connection between us that I don’t feel with anyone else.
“My sister asked if I had romantic feelings for you, and I couldn’t answer that. Romance is… irrelevant, so I never really gave much thought to it. Yet the more they explained the sensations, the feelings, the way the body reacts, I couldn’t deny that I felt those things.” Her head fell as she broke eye contact, tempering the hope I felt at her words. “...When I’m collecting material for you,” she finished with a whisper.
I felt myself physically deflate. My mind had warned me that this wasn’t going to end how I hoped, but hope was a downright bastard. Those sweet lies it whispered in my ear were a seductive call I couldn’t help but follow.
“The me you see in those videos? That’s not me. Not really. I’m actually not that fun in bed. The guys have mentioned numerous times that it would be better if I ‘livened’ up during sex. I enjoy it, but I don't express it. Sometimes I pretend, but that takes away from the experience. Like, I don’t have sex so they can enjoy it. I’m happy they do, but it’s primarily about my own enjoyment. So long as they do a decent job pleasuring me, that is good enough. It's why I don't really care about who I have sex with so long as I feel good.
“That all changes when I think of you. I have butterflies in my stomach riding Ryan’s cock as he records me. A giddiness runs through me as I snap a selfie kissing Grant’s cock. A euphoric rush washes over me when Colin blows his load over my face before grabbing my phone to take a picture. Even when it’s something as simple as posing for Emily, knowing you are going to see it arouses me. When I think, ‘How is Isaac going to react to this?’ it excites me in ways I didn’t think were possible. Then I see it. The expressions you make when I tease you about it. Hearing how you masturbate to them… How they drive you wild… It satisfies me in a way sex doesn’t.”
There was pain in her expression as she **** herself to continue. “But you were right. This is a one-way street. I know that and I know you deserve better, but the idea of going back to how things were… I’m afraid of letting this slip from my life now that I’ve grown accustomed to it. Maybe I could find someone else that elicits something similar, but I think we both know that is unlikely. That this even exists is a miracle itself.” She brushed the hair that had fallen into her face as she looked up. She was avoiding looking at me, focusing forward. “You are a unique guy in my life. The other guys care about me, but it is different than you. They aren’t concerned with who I sleep with or what I do with other guys. You do. And I love that you do. It makes sex with other guys so much better because I know what it does to you. I see it in your eyes when I talk about it. I see that hunger that haunts you. It hurts, but you can’t stop desiring more. Craving more. I see it and it feeds my own desires.” There was a quiver in her voice and I could see wetness in her eyes. “But I know that isn’t what you need. Friday confirmed that. You asked if I was jealous, and I was. Seeing you react to my friends’ advances hurt. It hurt because they desired you. They made you feel wanted. The smile you had. The confidence you radiated. All it did was drive home how unhealthy things are between us.” Her eyes went to her hands that she rested on her lap. “I never gave much consideration to why I was ‘off’ compared to other people. It never affected me or my relationships in a negative way, so why bother? You changed that. **** me to face it. Like why I am perfectly content fucking a man I barely know, yet the idea of sleeping with you makes me feel… nothing. It’s wrong. I know it is wrong. I want it to be different. I want it so badly. Yet my desires have little say in how I feel apparently.”
“We got close on Friday.”
She looked away as I saw a flash of guilt. “Letting you have sex with me is not the same as wanting to have sex.”
The silence was heavy as we both were left to our thoughts. She had dropped a lot on me. I could only imagine the sorts of things she talked about with Emily and Sarah if this was the result. As for the content, I didn’t even know where to start unpacking. The situation was fucked up. We both knew that. Her opening up confirmed a lot of what Ryan had told me. Never before did I have such an open and honest conversation with Emma yet feel so lost as to what to do with it all. It made me sick to think that maybe there was no solution to this. That my initial thoughts and feelings were correct and this whole thing was doomed to failure.
Jesus, Emma literally admitted that she got off with other guys thinking about me while simultaneously having no sexual desire for me. She loved tearing me down, getting a twisted satisfaction from it. Building me back up, however… I don’t know if she didn’t know how, or was simply not equipped to even try. She knew that too and it upset her. Out of everything, that much was clear. Inflicting hurt was easy, and she hated that it was the only thing she seemed to know how to do.
Standing from my chair, her head swiftly turned to me. Her eyes tracked me as I walked over to her. I offered my hands to her. Her gaze went to my hands, then back to me before gently reaching for them. I helped her to her feet. She was as short as always, yet she always seemed to be so much more. Her presence was always this overwhelming thing before me. Today? It was different. I wasn’t cowed by her smug grin or overbearing confidence, nor did I feel that I was towering over her. For the first time, we were just… there. Maybe not quite equals, but close.
Her eyes studied mine, unsure of what was happening as I leaned in. My lips brushed hers for an instant before she pulled away. Still holding her hands, I stepped forward and leaned in again. The kiss lasted a few seconds before she pulled away once more.
“Isaac—”
“Are you willing to try?” I whispered.
“What?”
I spoke in a soft and gentle voice as if she would flee at any moment. “I’m not asking you to be the perfect girlfriend or get everything right. You know my feelings about you and other guys, so you know I won’t tell you to stop. Know that I don’t want you to stop. Tear me down all you want. I can take it.” Her eyes were wide as she looked at me. I knew she could feel the tremble in my hands as I pushed myself forward. “But you need to learn how to put me back together again or all you will be left with is rubble. You think you have to be perfect right from the get-go, but you don’t. You can fuck up. You will fuck up. I need to know that you are trying though. That you want to do something more with me than grind me down until nothing is left. If you are willing to try, then I will work with you to find something that works for both of us for as long as we need to.”
“What if I can’t?”
I didn’t answer right away. “I would feel better trying and failing rather than living with the regret of what might have been.”
“You say that now…”
“This is it, Emma. We can’t keep circling the drain like this. Either we take the plunge, or we put an end to this. Prolonging the suffering doesn’t help either of us.”
She closed her eyes and took a breath. Oh man. Even now, I felt pulled by the promise of those wonderful lips. Lips I’d kissed! If past me could see me now…
Emma’s eyes opened and I braced myself. I don’t even think I was breathing as I waited for her answer. This was the all-in moment. I’d either win big or lose everything.
“A quest, then.”
I groaned. “Emma—”
“This is important. For both of us.”
Sighing, I nodded. “Fine. What’s the reward?”
“Level Five.”
I frowned. “I thought you said Level Four was the last level?”
“It was. Think of this as an expansion. You—we—get to explore a whole new experience. Together.”
It was easy to understand what she was implying. Level Five would be a relationship. A real relationship.
“Failure means this all ends, I presume?” She nodded. Stepping back, I ran a hand through my hair. It was weird not having more of it. Another sign of how much I had changed since meeting her. “Okay. What do I have to do?”
“You? Nothing.”
My eyes narrowed. “Nothing.”
She nodded.
“Okay… Then what is the quest?”
The way she looked at me made my heart hammer. She wasn’t trying to provoke me, but the sheer weight of her expression triggered something in me. Without her even saying anything, I understood that this was going to hit hard. Harder than anything before.
She didn’t flinch at the weight, standing tall and proud as she looked me in the eye. There was a silent understanding between us and the main reason behind the quest. If we got through this, we could get through anything.
“I’m going to sleep with your friends,” she declared.
I think I lost consciousness there for a split second. Maybe not literally, but it damn well felt like it. I was suffering from a mental equivalent of a gut punch. Sweat began to form on my forehead as I felt a sickness grab my stomach and twist it around. I had told her I could take whatever she threw at me, but this?
Her cool gaze watched, knowing what her words were doing to me and offering me nothing.
The last time. This would be the last time she was allowed to take without offering anything in return.
Complete this quest, and she would give me what I needed.
But was this really a quest I could complete?
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Beauty and the Nerd
A rose with a thorn, or a cactus with a flower?
The school slut gets involved with the top-scoring nerd. (Main story completed)
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- Slow Burn, Teasing, Femdom, Voyeurism, Slut, Cuckold, Cuckolding, promiscuous woman, Swinging, Humiliation
Updated on May 2, 2025
by white_horse
Created on Dec 31, 2021
by Vox121
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