Leveling Game

Emma was true to her word. I shared my Google Drive folder with her and the following day there was a folder labeled with my name. I suppose that made sense considering I wasn’t the only one who she was sending pictures to, though I couldn’t help but be curious how many others there were and the kind of photos they had.

Inside was everything I deleted plus extra. I went through it and sorted it into three folders. I named them by tier, with her non-nudes being tier zero, her nudes being tier one, and the newest level being tier two. As I sorted the pictures into their respective folders, I hesitated at the newest tier twos. Double-clicking on the thumbnail, they blew up to full size. I knew immediately that she had sent me three pictures from three different guys. Knowing her, that was on purpose. A subtle reminder that rumors of her promiscuity had a solid foundation. Honestly, I wasn’t too impressed by the two of her giving blowjobs, but I couldn’t put my finger on why.

The third one had promise though. It was another top-down, taken by whoever she had been sucking off. The dick wasn’t that big, thank god, but I loved the way Emma was posed. Mouth open, she had both hands on the cock like she was jerking it off. It wasn’t big enough for both though, so there were only a few fingers from each one on it. Her tongue was flat against the underside of the head as it pointed towards her waiting mouth. Her blue eyes were staring up at the camera, silently begging for it. The timing was perfect, and I could see the white jet as the guy gave Emma exactly what she was begging for.

Damn it.

I had to pause my picture sorting to rub one out. I couldn’t believe I was already fucking doing this when it had only been a day. It was a toss-up between this new one and her facial one on which I came to. I was switching between the two toward the end. After cleaning up and heading back to my computer to finish the sorting, I couldn’t help but feel the familiar remains of guilt and regret. They weren’t paralyzing emotions anymore though. I still hated that I was doing this, but I accepted that there was some sick twisted part of me that liked it. The only thing that truly upset me was my feelings for Emma. Even after everything that had happened, everything that was going to happen, I still liked her for some inexplicable reason.

There was no lying to myself when it came to her. It was because I was weak that I was back here again. Was it because she was a hot girl giving me attention? Maybe. I didn’t know. All I knew is that even though I should hate her, I couldn’t stay angry at her and that made me angry at myself.

Another surprise awaited me. Three photos of Emma as a naughty schoolgirl. I chuckled as I filed them away for later. Her way of a peace offering. I had to admit though, she looked different with her hair back in a ponytail. A good different. I took that as a sign to push all this aside and focus on other things.

Days ticked past with Emma meeting me in the library a few times. We didn’t study anything but talked instead. Nothing intense or sexual, but regular friend stuff. School, grades, teachers, life, DnD… Whatever we were in the mood for. It was never long, maybe thirty minutes to an hour, but it went a long way to rebuilding the bridge damaged before break. Best part was she always sent me a new photo to drool over after we met. No matter how many nudes she sent me and how familiar her body became, there was always a pose or expression that set my body afire.

Saturday rolled around and DnD went like nothing had happened between us. I had to fudge a few rolls to make it a bit more challenging, but overall it went well. The entire time, I watched Emma intently as she joked around with the guys. Maybe I hadn’t been paying much attention before, but I recognized she was teasing them as well. Nothing hurtful or obvious of course, but just enough that I noticed it. The more I watched her, the more things fell into place. I never figured out why she always dressed so nice considering she was going to be spending hours in an underground cave filled with horny Neanderthals. That was the point. She knew the guys were horny shits and subtly encouraged it. Emma wanted them to ogle her. She wanted them to made cringe attempts to flirt with her, even to the point of giving teasing responses back. Nothing to confirm anything of course, but dangling the bait there to encourage them to continue.

None of it was for the guys’ benefit though. Maybe I was being biased or self-centered, but I swore she was doing it because of me. I always thought she was looking at me because I was the DM, but maybe there was another reason for it. Did she want me to be jealous that my friends were constantly eye fucking her, or did she want me to be angry that she was encouraging it? Things were never easy with Emma.

Why did I agree to this again?

It seemed no one questioned why Emma was always the last one to leave. Maybe because none of the ungrateful bastards wanted to stick around to clean up like she did. Even Mike consistently bailed. Et tu, Mike?

“I really had fun tonight.”

“I’m glad,” I said as I stuffed an empty pizza box into the bag.

It was funny how we never seemed to run out of things to talk about in the library, but here it was like neither of us knew what to say.

“Things are awkward,” she finally said as she scrunched her nose while cleaning up Owen’s area. The guy was a pig in more ways than one. If there was one person I wasn’t going to miss once graduation hit, it was him.

“It’s going to take a bit.”

“Why don’t you take a seat?” she said, gesturing to my chair.

“I’m almost—”

“Take a seat, Isaac.” I froze at her voice. She wasn’t asking anymore.

Looking up from the mess on the table, I found her with that cool expression that once terrified me. There was still a spike of fear and a part of me wanted to immediately comply, but I found it much more manageable now. There was only one reason I could think of. I still held control over myself. Hardened with the knowledge that I walked away once, I knew I could do it again in a heartbeat. It quelled the animistic panic that her cool demeanor caused. If things got bad, I had an out, and that made all the difference. There was a balance of power to this weird-ass dynamic we had now. I wasn’t sure it was necessarily equal, but she was no longer a domineering presence able to take from me at will.

With a flutter in my stomach and a tick up in my pulse rate, I relinquished my share to her and took a seat. She gave me a predatory grin as she sauntered over.

“I’ve been thinking a lot this past week. About you, really.”

“I’m honored.”

“Mmm,” she said with a teasing smile. “I don’t know what happened over break, but I must say, I think I like this new Isaac. So confident.” Confidence wasn’t an adjective I’d use to describe myself. Too bad her definition of ‘like’ wasn’t the same as mine. There was a hungry look in her eye as she took a poised seat on the table in front of me. “Did you enjoy your new pictures?”

“Yes and no. I thought the two of you blowing those guys would be interesting, but I found them boring. The guy shooting his load on your face was good.”

I think my honest candor threw her off-balance. It didn’t sound like me. Even I was a bit shocked at how matter-of-fact I sounded. Only last week I would have been a stuttering mess if she asked that question. That didn’t mean I wasn’t embarrassed. I still felt a bit of heat in my cheeks, but it no longer overwhelmed me.

She frowned.

“What?” I asked.

“Boring.” I raised an eyebrow, but she didn’t say anything. Instead, she was lightly chewing on the tip of her thumb.

Sighing, she let her hand drop and looked at me. “Sorry. I’m not feeling it,” she said as she hopped off the table.

Shocked, I gaped at her. “What?”

“I said I’m not feeling it.”

Was this part of the game? It didn’t feel like it.

“Something wrong?” I asked as I stood up.

“Yes.” I waited for her to elaborate. It took her a moment of me staring at her before she finally gave in. “Fine. I’m afraid.”

“You?” I found that hard to believe.

She gave me a pouting look. “I’m not some heartless machine. I know it might seem that way, but I feel things too. There are so many things I want to do, to say, but I’m constantly holding myself back because I know what I do to people. What I can do to you,” she added softly.

“I thought you said you wanted this so you could let loose.”

Emma nodded. “I thought I did. Now I’m not so sure. If I break you too…”

“You won’t.”

Her blue eyes raised to look into mine. We stood silently for several seconds before she sighed. “Where the hell was this Isaac hiding a week ago?”

I scratched the back of my neck, glancing around. “I don’t think I changed much. I just got some advice I’m going to try following.” She quirked her eyebrow at me, but I waved it off. “It’s a long nonsensical rambling about touching stoves, but I have a lot of respect for the guy who gave it.”

She stared at me for a long while and I would have given anything for a peek inside her mind. “So I can push a little?”

I nodded.

“Okay.”

“Okay?”

“Yeah,” she said, gesturing to the chair. I sat back down, feeling nervous and confused. Did I really just help her get her mojo back?

I truly was a lost cause.

She took a seat back on the table as she schooled her expressions again. “Isaac. Why are you doing this?”

I was momentarily confused. Were we still…?

“Uh… I’m not—”

“Is it because you like me?” I blinked. She waited patiently for me to answer.

“I, uh…” I struggled with the answer. I knew the rules and this was a direct conflict with them. I wasn’t supposed to have these feelings for her. I also wasn’t supposed to lie to her either. Silence wasn’t an acceptable answer, so if I was going to break a rule… “Yeah. I do.”

“Not as a friend, Isaac. Do you like me as a woman?”

My heart began to pick up its pace and I shifted uncomfortably. “Yes,” I answered softly.

She tsked. “I told you that was a no-no. I was gracious enough to give you a second chance, against my better judgment, and you immediately start by breaking a rule.”

Frowning, I stared up at her. “I haven’t acted on it.”

“But you admitted to it.”

“I thought one of the rules was honesty.”

“True.” She hesitated before leaning slightly towards me. Her eyes were locked with mine. “Tell me, Isaac. While we are on the topic of honesty, do you like watching me suck other guys’ dicks?” My stomach did a little flip as I realized which button she was going for. Already, I could feel the lump in my throat form as I remained silent. I knew the instant she found what she was looking for because I could see the excitement burning in her eyes. “That’s pretty fucked up, Isaac. I thought you said you liked me.”

“I do.”

“Then why are you so happy getting pictures of your crush blowing other guys?”

“I’m not,” I huffed.

“Bullshit. You were just talking about how great the picture of the guy blowing his load over my face was. I bet you jacked off to it too.” Her hands tightened against the edge of the table as she leaned in. “Did you pump that cock of yours wishing it was my mouth instead of your hand?” I didn’t answer. It felt like a rock was shoved down my throat as I stared at her. I didn’t like how she was taking my feelings for her, twisting them, and throwing them back into my face. I told myself that this was all a show. She was only saying this to get a rise out of me, but there was something about that glint in her eye that made this all real. That she was genuinely berating me for having feelings for her. It made it hard to know which was real and which was the act.

“Or maybe you just like the idea of your crush getting passed around. Is that what excites you, Isaac? I had to suck three different cocks to give you those pictures. Three guys, Isaac. You wanting more means I have to suck more cocks. Do you still want me to do that? Answer me.”

My jaw quivered. This was all just a game. I needed to remind myself of that. “No,” I said softly.

She frowned. “So you don’t want any more pictures.”

“I… I do.”

She sighed angrily. “Now I’m confused, Isaac. Which one do you want? If you want more pictures, I need to suck more cocks. If you don’t want me to suck another guy’s cock, I can’t give you pictures.”

My heart was racing as I stared at her. She seemed to be saying my name a lot, using it as a tool against my psyche. Each time she mentioned my name it was like a hammer against my mental defenses. It hadn’t even been that long, but I forgot how shit this all felt. I could tell she was enjoying herself at my expense. In a twisted sort of way, that left me feeling okay. Judging by how hard I was, a part of me was enjoying this too.

I cleared my throat before speaking, doing my best to calm myself. “I want more pictures.”

Emma smiled, pulling away so she could sit straight. “So you want other guys to share this,” she said, running a hand over her mouth. “Even though you like me.”

I nodded, letting her have her fun.

“I want to level you up.”

Surprised, my eyes shot up to her. Fear powered my racing heart as a cold sweat washed over me. “Uh, Emma. I don’t think—”

“No. It definitely has to happen,” she said, hopping off the table. She grinned happily. “You’ll love it. Trust me.”

I was pretty sure she was going to love it. Me? Not so much. Morbid curiosity got the best of me and I nodded, standing up.

“I’m guessing this involves another demented quest?”

“Oh, don’t be like that,” she said with a smile. “This will be fun!” She was practically skipping as she headed towards my room. Curious, I followed her. When I got closer, she turned to face me. “Did you notice all your friends fucking me with their eyes tonight?”

A coldness settled into my gut. “It’s like that every week.”

Her smile grew wider. “Yeah. Poor guys probably go home and rub one out thinking of me.” Her eyes were practically sparkling as she moved closer to me. It was like she didn’t want to miss a single thing about my reaction to whatever was coming. “How about we help them out?”

So far, everything that had happened tonight had been… tame. It stung, but it wasn’t anything I hadn’t already wrestled with myself. This was new though. A direct escalation to anything that had happened before. It was the first real blow she landed.

“What?” I asked, mind reeling.

She was beaming at me. “This will be a win-win. You’ll be helping your friends relieve some of their pent-up needs and you will become a legend.” Her smile faulted as she looked like she remembered something. “Or they might finally realize what a disgusting pervert you are.” She shrugged, smiling again. “Win-win-win!”

“Emma, I—”

“Go get your phone and one of the unopened Cokes.” I hesitated, unsure of what she had planned, but relented at her hard gaze. She wasn’t asking.

Leaving, I headed back to the table and grabbed what she wanted. When I returned, her smile was back. “Great! Now open the Coke.” I did and looked back at her. “Spill it on my shirt.”

“What?” I asked, gaping at her.

“Spill it on my shirt,” she repeated with an annoyed tone. I looked down at what she was wearing. It looked nice. Expensive too.

“Uh…”

“Fucking do it already.” Flinching at her tone, I jerked the can in her direction. She gasped, jumping away as the liquid coated the front of her. Angry eyes shot up at me. “I said spill it, not fucking dump it.”

“S-sorry.”

“Fucking hell, Isaac. What the fuck is wrong with you?” She gave me a wink that deflated the harshness of her words. Acting. She was acting right now. Scared the shit out of me. My mouth fell open as she pulled off her shirt. Right there in front of me was a sight I had seen so many times before. I had masturbated to her so many times, yet there was something visceral about her being there in front of me. She was close enough to touch…

Already, I felt the painful pressure in my crotch area as blood diverted itself to make itself available. This wasn't the tepid one from before, but an all-hands-on-deck reaction.

Shooting me another angry glare, she opened my door and stepped inside with her shirt. “Where are your shirts?” she asked, looking around at my room. There wasn’t much to look at. My bed, a closet door, and my PC were all that was in it. Glad I kept the place clean. It would have been embarrassing if there were dirty clothes lying around.

“W-why?”

“You think I’m going to wear this home?” she asked, holding up the shirt.

My mouth went dry as my eyes lowered to the white bra. Oh man, it was so painful downstairs.

Snapping, she got my attention. “Eyes up here,” she said, pointing to her face. “I catch you perving on me again, you’ll fail this quest.” My eyes zipped to her face. “Now, get me something to wear.”

“Uh, okay,” I said, quickly going to my closet. Inside one of the drawers were my t-shirts. I figured since I was already bigger than her, they would all fit. Grabbing one that was a bit small for me, I handed it to her, making sure to keep my eyes up.

She eyed my choice. “Star Wars?” She grinned. “Good enough.” Turning to me, she stared at me. I stared back, and she got annoyed. I got the hint when she made the shooing motion. I quickly made my way to the door and went to close it but was stopped by her voice.

“What are you doing?”

“Uh, closing the door?”

“How are you going to take the picture then?” I turned slowly to find her looking at me.

“What?”

“The picture you are going to send your friends of me changing.” My mouth was dry as I stared at her. “Clumsy me spilled stuff over my shirt while cleaning up and you kindly offered to loan me one of yours.” Her eyes sparkled with mischievous intention as she spoke. “While I was in your room changing, you decided to sneak a peek and take a picture for posterity.” Her smile grew. “And because you’re such a great friend, you decided to share your bounty with the others.”

My heart hammered as I processed what she was saying. What she was making me do. This would change everything. If I thought things were bad in the group now, giving them access to half-dressed Emma was going to make things intolerable. I didn’t think it would change Mike or Trent. Mike didn’t strike me as that kind of guy and Trent was too shy. Ben and Owen would be absolutely insufferable.

“Leave the door open a crack.” Backing out, I did what she told me. “Are you ready?”

No, I wasn’t. Fumbling, I opened the camera app and looked up. God, Emma was beautiful. My breath caught as she glanced over her shoulder at me. “You are in charge of the photo,” she told me as her blue eyes held my gaze. “Take however many you think you need, but you are only sending one and deleting the others. I’m starting now,” she said, looking away.

I watched through my tiny screen as she mimed looking over her shirt with concern. Her face had completely transformed. No longer was she the teasing vixen that tormented me, but the Emma I was familiar with. She made all sorts of different faces as she stared at her shirt. Anger, sadness, regret. The entire time, she turned this way and that to give me different angles of her body. Her acting was scary.

I knew I needed to take a picture, but my thumb refused to press the button. This went beyond a simple picture. Until now, this was always about the two of us. Everything she asked, everything she demanded, it was all focused on one of us. Not anymore. She was expanding this to include my friends. The moment I sent this, things were going to change. Not just between me and her, but between my friends as well. I had no idea how they would react if I sent it. This was all her idea, but they wouldn’t know that. To them, I was no better than a stalker taking advantage of an innocent girl.

Fuck.

“Did you take it yet?” she asked, not looking toward me.

“N-no,” I said.

She glanced over her shoulder. “If you don’t, it’s going to get worse.” She turned towards me, giving me a clear view of her chest as she looked down at her shirt. “You have ten seconds before we enter into phase two.”

Whatever phase two was, I knew it wasn’t anything good.

Heart pounding, I struggled to line up the shot. Between my shaking hands and the refusal to press the button, my ten seconds expired.

She glanced up, dropping her shirt. Holding my gaze, I lost myself as I watched her reach up behind her and unclasp her bra. I practically fell to my knees as I watched her hold it out, breasts exposed to the world, before dropping her bra onto the floor.

“You don’t have much time to take the picture,” she said, grabbing my shirt. “Once I put this on, it’s over.”

It could have been over in seconds, but she didn’t. Instead, she took her time, examining the shirt, turning this way and that, but I noticed that she was never giving her back to me. Every shot I would take now, I would get a picture of at least one of her bare breasts in it. The tamest I could hope for was side-boob.

“I’m losing my patience, Isaac. Take the picture or you will fail and it all ends.”

“Fuck,” I grunted as I jammed my finger against the button. The shutter flickered again and again as the pictures were saved onto the phone. She heard me take them. Since I rarely used the camera function, I’d never gotten around to shutting off the noise it made.

A grin on her face, she pulled my shirt over her head and put it on. Strolling over to me with a seductive gait, she opened the door. “Well, well, well. What do we have here? A fucking pervert has been peeking at me,” she said, grabbing my phone. She swiped through the pictures I had taken. “There are some good ones in here… Which one are you sending your friends?” she asked as she handed my phone back.

Flicking through them, I realized that my hesitation had cost me. These were all bad in the sense that they were good. Because Emma was actually posing for me, I had clear shots of her breasts and innocent face. No one in a million years would believe she was in on it.

“I know it is tough, but try to be quick.” I jumped when I heard her soft voice in my ear. Turning, her head was hovering over my shoulder, glancing down at my phone.

“T-this one,” I said. It was one of the few that only showed some side-boob. It didn’t make me look quite so bad, though that was going to be impossible.

“Delete the other ones,” she said. I could feel the heat of her body as she hovered uncomfortably close. I did what she asked, smelling the wonderful scent of her perfume as it surrounded me. “Good. Now send it. The message is up to you.”

Opening Discord, I felt numb as I typed out my message. It was basically, “You’ll never believe what I just saw!”

I jumped when I felt pressure against my back. Emma was leaning against me, snaking her hands around me in a hug as she looked around me to see what was on my phone. “Send it yet?” she asked sweetly.

“N-not yet,” I stammered.

Her voice was heavy in my ear, her breath hot against the skin. “You know that once you send that, they won’t just be fucking me with their eyes anymore. I am going to be doing all sorts of nasty things in Ben and Owen’s imagination.”

My skin tingled as I felt her hands run along my chest, going down to my stomach. It was like electricity running through me as her hands slid down the outside of my legs before running inward. She was so close to my **** erection, but her hands were never more than a tease, purposefully avoiding where I wanted them to go. She took a deep breath, relishing my inner conflict. This was a test. Whatever happened next would be on me. She wanted me to do it, but we both knew only one person could actually do this. Her desire to manipulate me for her own pleasure, or my resistance. Posting this picture to Discord was going to prove my willingness to submit to whatever hell she was preparing for me, and I would have no one to blame but myself.

With ragged breaths, I lowered my phone and head. Her arms tightened around me, breasts pressing against my back. Her breath tickled my ear as she spoke.

“Welcome to level three.”