Disable your Ad Blocker! Thanks :)
Chapter 30
by Vox121
What's next?
Level Four
In that twisted way that usually came from dealing with Emma, I found a sort of clarity that put the shit she put me through into context. There was no denying things anymore. I enjoyed the sight of Emma with other men. Whether it was getting fucked or blowing them didn’t matter. It was a twisted sort of pleasure because I technically didn’t like it. I guess it was a form of masochism but instead of enjoying physical pain, it was the emotional and mental anguish that got me going. Emma was absolutely a sadist. Nothing got her going more than fucking with my mind.
God, were we a match made in Hell.
Before school kicked back off, I spent my last day of freedom doing some research. I suppose the stuff I was into was cuckolding, but it was weird since Emma and I weren’t in any meaningful relationship and I thought cuckolding was more for committed partners. In the grand scheme of things, Emma wasn’t even doing anything wrong. She wasn’t in any serious relationships and was free to sleep with whomever she wanted guilt-free. It was my feelings that were fucking me up. Even though I had tried so hard to maintain that distance, even though she had warned me not to do it, I fell for her. I fell for her hard. I was so deep, I still liked her despite all the shit she put me through.
Or maybe I liked her because she put me through it.
It was a valid hypothesis. Before she came along like a category five hurricane chilling over a beach-side resort, my life was thoroughly boring. It wasn’t just that it was boring, but I had no motivation to spice it up. I was stuck in my ways, content to simply exist one day to the next. Emma was forcing me to do something other than that. There was never a dull moment with her in my life. I was constantly wondering what the hell she was going to bring up or make me do. I did them despite hating what they did to me. How they made me feel. She was pushing me, and I was adapting.
Over break, a storm had blanketed the town in snow. Too cold to walk to the library, I drove. Feeling a bit chilled from the drive and walk from the parking lot, I splurged and stopped by the ridiculously overpriced cafe inside the library. I suppose it was for a good cause since the money went back to the library, but it still felt bad paying nearly nine bucks for a hot chocolate. I took a few sips of my scalding drink before peeling everything off and setting up in the usual place. Without anything to study, I found a book from the new release section and hopped between reading that and messaging the others in Discord.
I honestly wasn’t expecting Emma to show up and was shocked when she began unbundling herself from the numerous layers she had on. With a sigh, she sagged into the chair across from me. A grin on her face, she reached over and stole my drink before taking a testing sip. I said nothing, watching as she swiped my hot chocolate entirely.
“Afternoon,” she said as she set the drink in front of her. Yep. No way was I getting that back.
“That was eight seventy-nine,” I said as I nodded towards the drink.
“I know, which is why I’m drinking yours instead of getting my own.” She had a proud grin on her face. “Don’t give me that look. You can afford it.”
“Why didn’t you just ask me to buy you one?”
“Easier to just take yours.”
There was an awkward silence that followed. She filled it by sipping at the hot drink. I simply stared at her wondering what the hell I was supposed to say in this situation. The funny part was the awkwardness I felt had nothing to do with her watching me jack off to a video of her getting fucked by some guy. No, what had my tongue in knots was her admitting she liked me too. It messed with me because I had no idea if she was serious or if this was just another one of her cons. It wouldn’t be the first time she used my feelings for her against me. But I saw the way she looked at me when she said it. She had dropped the devil Emma and was speaking to me as friend Emma. It was important not to jump to conclusions either, no matter how much that damn hope inside me wanted to.
‘Like’ encompassed a hell of a lot of territory in that context. Did she like me as in the same sort of feelings I ‘liked’ her? The type of like between people who are romantically interested in each other. That was the hope, but nothing was ever simple with her. No, it was most likely she ‘liked’ our dynamic. As she had said, failing the quest meant it all came to an end and that meant no more torturing the pathetic fool named Isaac. The stupid Isaac who had feelings for his torturer. The more I thought of it, the more the second seemed more likely. After all, feelings were against the rules and Emma didn’t seem like one to break them.
Then again, I was only here because she offered me a second chance and that was basically the cardinal rule right there.
“You’re not very talkative today.”
I shrugged. “Been thinking a lot since our last session.” She sipped at the hot cocoa, blue eyes never leaving me. “Been wrestling with some truths that were exposed during that… quest.”
“You made it though. A bit too close for comfort, but you made it.”
“If he had beat me, would you have still failed me?”
“You know the rules.”
“And the feelings part? Isn’t there something about that in the rules too?”
To my surprise, she didn’t say anything right away. She was always quick on her feet so the silence meant she was weighing something big.
She set the drink down in front of her but didn’t remove her hands from it. “That’s right! We haven’t talked about your Level Four upgrades.” I felt myself blink a few times as I stared at her. So that was how she was going to do it? Just ignore it entirely.
I sighed as I decided not to push the subject. I gestured for her to continue and watched as she squirmed excitedly in her seat.
“There isn’t much choice this tier because gathering material for it is a process. As you probably guessed, you’ll start getting pictures of me in various positions with guys. There are three categories. First is right before penetration, most are going to be during, and finally the money shot.” She was grinning like a fool as she leaned forward. “So, which one do you want first?”
Like the idiot I was, I found myself seriously contemplating the pros and cons of each before answering. “During.” She quirked an eyebrow and I found myself explaining myself despite her not asking for it. “Well uh… Seeing the faces you made in the video...” The longer I spoke, the softer my voice got as my cheeks radiated heat.
Leaning against the table, she rested her chin on her fists. “So what you’re saying is you want to see me with a big, hard cock in me.”
I opened my mouth but no words came out as I floundered to respond. I mean, yes I did… but also no. Damn it.
Emma was loving every second of my mini-meltdown. “I have a feeling I’m going to have to put a lot of work in to sate your appetite.” Her head tilted slightly as she beamed a smile at me. “Does that make you feel warm and fuzzy inside? The girl you like is going to fuck so. Many. Guys. All to make sure you get the pictures and videos you want so badly.”
My throat tightened as I stared at her. I hated how she put it like that. “Videos?” I managed to croak out.
“Ah. Forgot about that bit. Those are your new quest rewards. Sometimes you’ll get clips. For big things, you’ll get the entire video. Not too many of those, so they are going to be more of a special occasion thing.”
“Huh?”
“What?” she looked as confused as I was.
“Not many?”
She burst out in laughter, struggling to control the volume. It lasted a good ten or twenty seconds before she was able to speak. “Good god, Isaac. How much sex do you think I have?” she asked as she wiped a tear from her eye.
“Um…”
“I do have other things to do.”
“Yeah but—”
“But?”
I didn’t respond immediately as I found myself in the hole I dug. “Haven’t you been… uh… doing… um… this… for a while?”
“This?” she asked with raised eyebrows. “What is ‘this’ you speak of?” I gestured between us and she shook her head. I frowned, knowing she was fucking with me.
“Sharing videos and pictures with other guys,” I whispered.
She was grinning proudly. “I have.”
“Well… Wouldn’t you have a bunch then?”
“Can I let you in on a secret?” she whispered in a conspiratorial way, leaning forward in the process. I matched her, getting closer. “I don’t fuck guys so you can get off to it.” I yelped as her finger flicked against my forehead and sent me jerking back into my seat. She giggled as I rubbed my sore forehead. “Oh, don’t pout. I promise I have some good stuff for you.” Finishing the last of my drink, she set it down and began putting on her layers again. “Come on. Walk me out.”
We put on our coats, gloves, and hats before gathering up our things. I walked beside her in silence, tossing the empty cup in the trash on the way out. Outside the library, I glanced over at her. My eyes trailed down to her lips as I watched her breath plume out in frosty clouds.
“Thanks for not failing,” she said softly. My eyes moved from her lips but she wasn’t looking at me, focused on some distant point.
I felt my chest tighten and I had the overwhelming desire to ask her about what she meant by ‘like.’ Shoving that thought down, I went another direction. “Can I ask you something?” She finally looked over at me, waiting for me to speak. “H-how many?”
“Hmm?”
“How many have made it to Level Four?”
The corner of her mouth twitched upwards. “That’s classified information.”
My shoulders slumped. Figured.
She said nothing else, blue eyes boring into me intently. “I’ll tell you if you do something for me.”
My heart was racing as I met her intense gaze. “This a quest?”
“More like a side-quest,” she said with a grin. “Interested?” My head moved without me telling it to, giving her the barest of nods. She didn’t say anything for a long time. My heart felt like it was physically moving my body each time it hammered my chest. The anticipation was killing me. Emma was a fucking master at timing things like this. She knew how to drag something out for maximum effect yet not let it linger too long so it became a slog.
When she finally spoke, her voice was soft; almost kind. Even though there was no one else around to hear her, she was making it abundantly clear that this was meant for me and only me. “I’m going to Zach’s house after this. When I get there, he’s going to fuck me.” She paused, letting her words sink in for maximum effect. And it certainly hit me. My fists and teeth were clenched tightly as I struggled to maintain a neutral expression. I felt woozy as my heart shoved blood through my body.
Once she was satisfied she had extracted all she could from my reaction, she continued. “Tell me how he’s going to do it.”
“W-what?”
“I want you to tell me what position he is going to fuck me in.”
“H-how the hell am I supposed to know that?”
She was shaking her head before I finished. “No, Isaac. I want you to pick the position. Missionary? Me on top? Something else? Whatever you tell me, that’s how we’re going to do it.” She took a step closer, eyes locked with mine. “I want you to leave here knowing that another man is fucking me the way you want him to fuck me.”
“That—” Words failed me. I could barely take a full breath as the world seemed to swirl around me. It was hard enough to stand upright, let alone answer her. I sucked in a lung full of air, hoisting my back straight as I pushed through. “What’s your favorite?”
She shook her head. “This isn’t about me, Isaac. This is about you. How would you like him to fuck me?”
Even with the freezing air around us, I was burning up. Sweat beaded on my forehead. The rough material of my glove scratched it as I wiped it away. My answer was a mumble I didn’t even understand.
“What?”
I tried again without any more success. Squeezing my eyes shut, I focused on my breathing. It was so fast. Probably why I was so damn dizzy. It was a struggle, but I finally managed to calm down a little. When I opened my eyes, Emma’s were right there waiting. I knew she was enjoying this, but her devil personality wasn’t out at the moment. Her gaze was serious and intense, but she wasn’t making a show of enjoying herself.
“On top,” I croaked. “I want you on top. You were so goddamn sexy in that video...”
I cleared my throat as my face heated, the mental images already forming in my head.
“Okay.” Was that a blush I saw on her cheeks, or was that from the cold?
And just like that, it was done. All that **** for that? Yet even though I was mentally and emotionally drained, there was something else there. Exhilaration? Maybe that was why I was so wired despite feeling like shit. Emma was going to ride some guy's cock because I told her to do it. Me. The thought of that…
So lucky my coat was covering my erection right now. Yeah. No denying I was an emotional masochist with that little traitor running free.
“Sixteen.” I looked up with a confused look. “You wanted to know how many got to Level Four, right? Sixteen.” That was a much higher count than I expected. My shock must have been clearly written on my face because she chuckled lightly. “That’s total. Most wash out in a week or two. I think a lot of guys think leveling gets them closer to becoming content producers rather than consumers. Not how this works.”
“Have you slept with anyone you do this with?”
A coy grin graced her features. “That’s classified.”
Considering some of the quests she gave, I figured there was a high chance of that. The funny thing was I wasn’t even sure that was what I wanted. That’s how fucked up this whole thing was. I wasn’t that far gone where I would turn it down if she offered, but I couldn’t be sure that was what was driving me anymore. I absolutely wanted to sleep with her, but would I be okay if that didn’t happen?
After all, we weren’t in that type of relationship and she had made it clear that it wasn’t in the cards.
“Can you tell me how many are in Level Four now?”
She thought for a moment before shrugging. “Four including you. They are a bit scattered in terms of length, but the newest guy before you has been Level Four for about three months now. One has been there for a long time.”
God. How many poor bastards did she have in this web of hers? I wasn’t only curious about the number, but also the type of guy. Were there really that many guys out there who enjoyed this type of thing?
“Can I ask you something else?”
“Later. It’s fucking freezing out here,” she said, wrapping her arms around her chest and doing a little dance.
“This is important.”
She sighed, a huge plume of white flowing from her. “Be quick.”
“How many guys do you tease like this?” She didn’t say anything as she stopped her dance. “I don’t mean sending pictures. I mean the quest stuff. The stuff where you make me ask and answer embarrassing things.” I thought for a moment before continuing. “Stuff like the conversations we have after DnD.”
She was messing with me again as she let the silence drag out. All I could do was look into her eyes and wait.
And wait.
At first I thought she was teasing me, but as the silence dragged on it dawned on me that she wasn’t dragging this out. She wasn’t going to answer me.
“See you later, Isaac,” she said before walking away. I didn’t move right away, my head tracking her as she left. I continued my silent observation until I saw her get into her car and drive out of sight. She hadn’t answered me at all. Not even a teasing, ‘classified’ sort of way. Her silence was answer enough.
I was the only one who suffered the full brunt of her sadistic nature. She wasn’t going to come out and say it, but this all but confirmed it in my mind.
And knowing this set me back at square one in trying to figure out just what the hell my relationship with Emma actually was.
What's next?
Disable your Ad Blocker! Thanks :)
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)
- Tags
- 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
- 9,956 Likes
- 1,215,393 Views
- 1,250 Favorites
- 1,169 Bookmarks
- 326 Chapters
- 101 Chapters Deep
- All Comments
- Chapter Comments