The Quest

It had been days since I had agreed to level up. The picture she sent me confirmed I was still where I was previously as she was fully clothed, though the way she hiked up her skirt…

Friday turned out to be the day when I would get my chance. It was nearly midnight when my phone chimed. I found a message from her waiting for me. I expected it to be the picture she owed me for today's study session. I was surprised to find an actual message.

>You busy?

>Nope

>Still want to level up?

>Yes

>Failing this means it all stops. Still up for it?

Taking a deep breath, I pumped myself up. Whatever it was, I’d do it.

>I’m ready

There was a long pause. Agonizing minutes passed as I waited, phone in hand. Emma was a master at this. It was like she knew how the wait tormented me. I was about to text her asking what I needed to do when I got her text.

>In order to ascend to the next level, one must prove themselves worthy of their dedication to the cause. To complete this quest, you must turn in: one dick pic. Failure to do so will mean expulsion and forfeit of all previous rewards

>And it has to be yours. No cheating

Stunned, I sunk back onto my bed as I read and reread the message. The phone chimed again.

>You have five minutes

Fuck. A time limit too?

Taking a deep breath, I stood and paced back and forth. It was fine. It was just a picture. She’d been sending me stuff for weeks. It was only fair, right? Fair wasn’t the issue though. It was that Emma would have a picture of my god damn dick. What if she didn’t like it? I mean, I suppose it was okay as far as a penis went, but did I really know that? Did she want it to make fun of me? That wasn’t outside the realm of possibility. Emma was a nice person most of the time, but her teasing could draw blood if you didn’t have thick skin. I’d been able to withstand most of what I had directed at me, but I knew even I had limits. The thought of her making fun of me if she found my penis weird or small terrified me beyond reason, even if I had a feeling she wasn’t that sort of person.

>Four minutes

Fuck. Fuck, fuck, fuck.

Hand trembling, I opened the camera app and pointed the phone down at my crotch. With my other hand, I pulled back my shorts and boxers to give a somewhat clear view. Was I really doing this? Fuck.

I wasted precious seconds trying to figure out the best way to go about it. In the end, I had no idea. Cursing, I took the photo. Not giving it another thought, I sent it to her. My heart thundered as I plopped back on my bed.

It was done.

I’d done it. I actually went through with it. My first dick pic.

Hearing the chime made me jump as I quickly looked at what she sent. There was a mix of dread and curiosity as I opened her message.

>Hmmm

>What?

>Taking a picture in a dim room of something in shadow and you didn’t even use flash

>It is still a dick pic

>True. Leveling up on a technicality though… is that how you want to ascend?

My body was still shaking as I let out a breath. “Shit.”

>Tell me what you want

>Oh? I get to choose? Interesting…

I may have regretted that after seeing that message. Giving Emma more control over the situation was asking for trouble.

>I want a picture of you sitting, cock out, full mast

Yeah. Hindsight was a bitch.

>You want a picture of me with an erection?

>No, just your erect cock

>Three minutes BTW

>Wait, how am I supposed to get you that in three minutes?

>By not wasting time complaining about it

Fuck.

Normally this wouldn’t be an issue. The curse and blessing of my teenage body was it seemed ready to go at the slightest stimulation. The problem? The amount of pressure was messing with my head.

Pants pushed down, I desperately tried to coax my downstairs buddy awake. Of all the times to be shy, now was not the time. I got a text warning me of the two minutes and I cursed. Damn it. Why didn’t I just retake the fucking picture with flash?

Forcing myself to calm down, I closed my eyes and mentally drew a picture of… something. Calm, deliberate strokes. The mental picture sharpened and became more defined as I felt myself responding.

Emma.

Thinking of her always did the trick, and my mind seemed to know. I brought up the latest picture she had sent me in my mind. Everything seemed more vivid here, morphed by my flawed recollection and twisted imagination. The look of those clear blue eyes staring at me. The coy smile she gave me as her hands worked at the buttons of her shirt.

Opening my eyes, I found myself in business. Moving quickly, I snapped a picture, making sure to use the flash. I’d already got the one minute remaining warning and I prayed I was fast enough.

The wait was agonizing, and I knew she was doing it on purpose. She never let a good opportunity to tease pass her by.

>lol Was that so bad?

Putting my shorts back in order, my nerves had all but killed my erection.

>How big?

>Don’t know

>Bullshit

I sighed. It had been worth a shot.

>It's average

>Not what I asked

She was actually going to **** me to say.

>Average is about 5

>About? Not asking for the average dick size Isaac. Asking what yours is

>Fine. It is like 9/10 of the way to 5 inches

>So not 5. You are 4 9/10

>Close enough to 5

>Close enough to 1st place is still 2nd

>I said about

I was getting angry and frustrated. This was exactly what I was afraid of. I’d looked it up. 5.6 inches was the ‘official’ average for the US. I didn’t hit that, so I was permanently in that wonderful ‘below average’ place. I fucking hated it, and there was nothing I could do. Even if statistically I was in good company, that didn’t make me feel any better.

>Relax. It’s cute

Cute wasn’t what I wanted my dick described as.

>So comforting

>Lighten up, Isaac. You leveled up! You should be happy

>More nervous than anything

>Do you want your reward?

That last message wiped away any lingering self-pity about my dick size.

>I get a reward?

>Not usually. Most guys just send me a shit top-down with no thought in it. Since you took such a great picture, I need to reward you. So, I’m going to upgrade that picture I owe you for today

My eyes hovered on the ‘most guys.’ As I suspected, there were others. How many? I suppose it didn’t matter, but I hated how it made me feel. I knew I shouldn’t be jealous, but how could I not be? Another not-so-gentle reminder that I wasn't special to Emma.

I understood how guys fucked this up. It was hard to keep an emotional distance from Emma, especially as time went on. It wasn’t just about looks. Yes, she was goddess-level attractiveness, but her personality was fun too—when she wasn’t letting her tormenting demon side out. So far, that was really the only flaw to her that I knew of. Her teasing was relentless, and she reveled in it.

>Are you ready, Isaac? This is your leveled up nude photo

I waited with bated breath, my mind racing through all the possibilities. Finally, I was going to discover what the hell I had gotten myself into.

Ugh. She was doing it again. I was going crazy with anticipation. My heart was thumping in my head as I struggled to find some outlet to take my mind off things.

After nearly five minutes, my phone finally chimed. I raced to see what she sent me, surprised and disappointed to find it wasn’t a picture, but more text.

>Do you want to know why I wanted you to take a picture of your dick?

Frowning, I sent her a question mark in response.

Still staring at the screen the image I’d been waiting for appeared. Trauma wouldn’t even begin to describe the shock I was feeling as my mind struggled to comprehend what I was seeing. Almost immediately, she sent me another text.

>Comparison

There in the picture was a smiling Emma. She was clearly the one holding the phone, slightly elevated to give a top-down view. Unlike the others, this was taken with her cell phone and wasn’t as staged as the others. Of course it wasn’t. There against her mouth was another man’s cock. Her lips pressed against the tip in what seemed like a kiss. Horrified, I found I couldn’t look away, my eyes frozen on the sight. It wasn’t just the sight of her obviously about to give a blowjob. The more I stared, the more I noticed. Like how her clothes were awfully familiar. Heart racing, I realized that she was wearing the same clothes earlier today. A coincidence? Hard to believe that. Everything with Emma seemed to be planned in some way.

Things slowly began to click into place. She had been late meeting up. I still had her text telling me she was running to a friend’s house for a moment. Oh, fuck me. Did she do this before meeting me? I let my phone fall away as I ran my hand over my forehead. I felt sick. Did she seriously give a guy a blowjob before coming to study with me? I didn’t know. I had no clue at all. Now everything was suspect. All the times she had been late, hadn’t texted before suddenly showing up looking like she had sprinted over to the library. Maybe she was disheveled for another reason.

Fuck me.

What if it wasn’t just a blowjob? What if she—

I shook the thoughts out of my head, refusing to go further. It was all my imagination getting the best of me. None of this was new. I knew she wasn’t a virgin. I knew she’d lost that a long time ago. What, did I really expect her to have sex once and decide it wasn’t for her? Clearly, that wasn’t the case. The rumors around her were sounding a lot more credible. What if she was a slut? Did that change things?

Dangerous questions. Change what? We weren’t in a relationship where that mattered and she made it clear that she had no interest in actually dating anyone. Or was that only me?

I ran my hands over my face “Fuck me,” I groaned loudly. I was a mess.

My phone buzzed before a new ring sounded. Looking at the phone, I found she was calling me. Not just any call. A video one.

As if the night couldn’t get any worse.

I tapped the accept and her smiling face appeared. “Hey, Isaac!”

“Emma,” I said softly as I glanced away. It was hard to look at her without that visual of the cock against her sweet lips.

“Did you not like it?” I must have looked miserable because she sounded sad.

Jaw quivering, I worked up the willpower to look at her. She looked sad like she had been expecting me to like seeing a picture of her like that. “I don’t know,” I managed.

“Was it the angle? I have some better ones.” She paused for a second to look at me. I think we both knew that wasn’t the problem. She was doing it again. I was playing the role of the mouse once more. “I have others that are me actually sucking them off, but you’ll have to wait until you can request one.”

“Are they all like that?” I asked, knowing full well I sounded miserable.

“Of me giving a blowjob? Most of them. Some are just handy’s,” she said, miming jacking someone off. “Since you unlocked this new tier, I’ll let you know what you can request.” She was practically bubbling as she spoke and I had a hard time reconciling her joy with my confused… disgust? Was that really what I was feeling, or was it something I believed I should feel? “I have four categories. The first is the pre-blowjob, so like the one you just got. The other three are a handjob, me giving a blowjob, and the last being… well… the end result. I’ll admit that they aren’t as high quality as the ones you were getting before, but I’m sure you can understand why. Don’t worry though. The other pictures won’t change.

“So,” she said with a smile. “What do you think? Worth a simple dick pic, don’t you agree?”

I let out a long breath. This was… not what I expected and I was too overwhelmed to confidently answer where my thoughts landed on this.

“This is a lot to take in.”

“You going to jack off to it tonight?” she asked with a sweet smile that suggested an innocence that didn't exist.

“What?”

“I’m curious.”

“I…” No way. I was debating whether I wanted to delete it or not. Even picturing it in my mind was bad. Seeing the actual image was too much and it would be best to delete and forget it. Not that I ever could. It was burned into my mind now. Shit, how was I going to maintain a normal relationship with her when she was sending me this shit?

Was my relationship with her ever normal?

“N-no,” I managed.

“So you don’t like it.” There was an edge to her voice. Looking at her through the screen, I saw her face had gone placid. Any trace of the playful side of herself was gone. She was difficult to read at the best of times. Now that was impossible. There were tendrils of fear wrapping themselves around me. She seemed angry at me. Shit. I didn’t want that. I needed time to think. To figure things out.

I floundered, sputtering out nonsense as I tried to buy time for myself to think.

“Do you want another one?” she asked.

“Huh?”

She still had that cool demeanor, but there was a crack in her mask. She couldn’t hide the glimmer of excitement in her eyes as she stared at me.

“Normally, I don’t do this so quickly, but I find myself wanting to help you. So I’m offering you a quest.”

“If I refuse?”

A cool smile. “Perfectly in your right.” I sighed in relief. I needed a moment to collect myself. It was like she was constantly knocking me off-balance and I needed a moment to get my head on straight. “You’ll have a penalty of course.”

“P-penalty? But I didn’t fail the quest!”

“Not taking it is a failure.”

“That’s not fair!” Her eyebrow twitched and there was a dangerous glimmer in her eyes. “Er… Sorry. You did warn me there would be penalties now.”

“So? What will it be? Yes or no?”

“What’s the punishment?”

She wiggled her finger back and forth in front of the camera. “Ah-ah. No can do. Just like the quest, you don’t know what it is beforehand.”

Biting my lip, I nodded. “Fine,” I grumbled. “What is the quest?”

Her smile was back, and I hated how after all this, it still made my stomach flutter. Why did she have to be so fucking hot? And crazy. No, toss all that. Why was I fucking doing all this? I hated it, right?

“Your quest, Sir Padawan, is an easy one. I mean, I really can’t believe how easy I’m going on you, so be thankful.” She paused for a moment, looking at me. “I want you to use that picture to jack off tonight. You can only use that picture. Nothing else, not even other pictures of me. Do that and I’ll give you another one tomorrow night after DnD.”

It didn’t surprise me, almost like I knew what she was going to tell me the moment she mentioned the quest.

Heart thundering, I decided to push a little bit, suppressing the fear long enough to speak. “You know, I could just say that I did it and you wouldn’t know.”

Her reaction surprised me. I expected her to get angry, or to threaten me. Instead, she shrugged. “I know.”

“That’s it?”

“You can lie,” she acknowledged. There was a small grin as she continued. “But you won’t.”

“You don’t know that.” She didn’t answer me as her grin morphed into a smirk. I didn’t like how confident she was acting. I was almost tempted to lie to spite her overconfidence.

“Remember, if you don’t do it then you get hit with a punishment.” I said nothing, smoldering. She leaned towards the camera, voice a whisper. “Want to know a secret about that picture? It’s from today. As for when today…” She trailed off with a shrug. “Remember the quest, Isaac. I expect to hear great things tomorrow.”

With a wink, she disconnected.

Exhausted, I put my phone aside and leaned back. I finally had time to think and was too mentally drained to actually do it.

Damn it. She had warned me about leveling up and like a fool I charged in, letting my dick do the thinking. It was hard to believe that me sending Emma a dick pic was the least of my concerns tonight.

Of course I wasn’t going to do that stupid quest. I was going to tell her that I did and be done with it. In fact, I would go a step farther and delete the damn photo in question. Yeah. That was the best thing to do. I’d fudge the stupid quests she would give me, then delete the ‘upgraded’ photos she sent me. I’d be getting nudes on the regular now. I was a bit sorry for the loss of the regular ones. They were hot in their own way.

The most important thing now was not letting her know I wasn’t actually doing her stupid quests. I figured that would be easy enough. She might have been able to mess with my mind, but she wasn’t a mind reader.

Grabbing my phone, I was resolute as I flicked it open. There was the offending picture. An easy fix. A few presses and the picture would be forever gone. I couldn’t believe she went and gave some random guy a blowjob before meeting up with me. I couldn’t believe she took a picture of her giving a blowjob, or at least the start of one. She sent this to me without a care in the world. What if I uploaded this on the internet or shared it with my friends? Hell, maybe there was stuff already out there of her. I know she said it would be an immediate termination of our little agreement, but the damage would already be done. It was difficult to believe someone like Emma was so open with this or trusting people to follow the rules. All she had on me was a dick pic with no way to identify who it belonged to.

I’d been staring at the picture for minutes now and still hadn’t deleted it. I don’t know why I was still staring at the fucking thing. I hated how it made me feel. Even though I knew it was impossible, I still had a crush on Emma. That hope couldn’t be burned away entirely, like a god damn immortal weed. What I hated most wasn’t the jealousy it created, it was the hope that lingered there in the shadows. The hope that, maybe, in some freak circumstance, maybe that could be me. I mean, she gave this guy a blowjob. Maybe that was in a higher level. Were there higher levels? There had to be. I couldn’t imagine what I would have to do to reach them, but if what I was seeing had links to those levels…

For all my determination, I didn’t delete the photo. Less than five minutes after she had hung up, it was transferred to my Google Drive and full-screened on my monitor. My hand worked my erect shaft as I stared at the picture. I was always a silent masturbater, but today I was a swirl of excess emotions. Confusion, anger, guilt, disgust, all a maelstrom inside me. Gasping for breath, I grew closer. I was going to cum staring at a picture of my crush kissing another man’s cock. I stared into those blue eyes as I reached my limit. One word left my mouth in a whisper as I blew my load into the waiting tissue. A name whose owner would never hear.

Spent, I sagged in my chair, blankly staring ahead at the photo. My anger was gone, replaced by disappointment. This was all my determination amounted to; doing exactly what she wanted me to.

Damn it.