Second Quest

She had me open ‘The Folder.’ As I woke my computer and started to navigate to it, I glanced over at her. She was back to being the unreadable woman I was used to seeing. Arms crossed, she stood patiently beside my chair.

Opening the folder with the rest of the ‘rewards’ she’d sent me, I was surprised to find a new folder there. Instead of it being marked by tier, it was simply labeled, ‘Quest Items.’

“Don’t open it yet,” she said as I moved to open it. “This is going to be a timed quest.” She took a deep breath. “In order to ascend to the next level, one must prove themselves worthy of their dedication to the cause. Failure to do so will mean expulsion and forfeit of all previous rewards. Do you wish to take up this quest?”

“I do.”

“Then open the folder, but nothing else.” The twisting anxiety was there as I moved the mouse to the folder. I knew I wasn’t going to like this, yet I couldn’t stop myself. Opening the folder, I found three video files inside. My stomach dropped as I read the labels. Cowgirl. Missionary. Doggie.

I looked over at her to find her with a smirk. “Nothing is free, Isaac,” she said, quoting what she told me before leaving vacation.

Three files.

Three positions.

Three. The number I’d picked out of six.

She had disappeared behind me. My back went rigid as I felt her hand run along my shoulder. “These are exactly what you think they are.” She let that sink in. I numbly stared forward, barely registering her hand as it moved back and forth along my shoulders. “Three videos. Three different guys. You can pick any of the three, but once you start, you must watch it to completion.” My eyes turned up as my head moved to face her. Her smile was kindly as if the subject material was something humorous. “In order to complete this quest and ascend to the next level, you have to cum before the guy in the video does.”

My eyes went wide, spinning around to face her. “What?”

“Oh? Was that unclear?” She leaned in. Her voice was gentle as she spoke. “I want you to jack off to me getting fucked and finish before the guy in the video does.” She smiled sweetly. “Can you do that for me?”

“Emma that’s—”

“No?” she asked with a pout.

Closing my eyes, I focused on my breathing. In. Out. In. Out.

“Fine,” I **** out as I opened my eyes again.

“Great!” she said, pulling away with a happy hop. “So, which one are you going to pick?”

“I… I don’t know yet,” I said, avoiding looking at the screen. “So… Do I text you when I’m done or…?”

She blinked at me, a confused look on her face. “Huh? I’m not going anywhere.”

A jolt ran through me. “What?”

“How am I going to make sure you beat his time or not?”

“I…I would tell you—”

“Nope! You are about to enter the Big Leagues. They don’t have tryouts based on the honor system. If you say you can throw a fastball, you better be able to throw it in front of an audience.” I said nothing, my jaw hanging as far as it could. She was serious. She was going to watch me masturbate to one of her sex videos. “What?” she said, frowning at me. “I told you this was going to be hard solo.”

“Wait, what if I had passed the first quest?”

“I’d be doing the work,” she said, making a jerking motion with her hand. A slow smile crept over her face. “Yeah. Easy win I’d bet. Then we’d celebrate you hitting level four by you showing me what you learned from the video.” The smile faded. “But sadly, that’s not going to happen now that you failed the quest.” Her hand rested on my shoulder, giving me a comforting squeeze as her expression shifted to one of pity. “Hey, look at the bright side. At least you’ll still get to cum tonight.”

Clapping her hands together, she took a deep breath and adopted a cheery disposition. “Now then, shall we start? Off with the pants!”

“Emma I—”

“Ten seconds.” I didn’t move. “Nine…Eight…Seven…” I jerked into action. Fumbling with the belt, I managed to get my jeans down as she hit two. “Underwear too.” I hesitated and she rolled her eyes. “Nothing I haven’t seen before, remember?”

And just like that, I was standing there with my pants and underwear around my ankles. My hands automatically moved to cover myself only to get a tsking noise from her. “Hands to the side. I want to see.”

“You’ve already seen it, remember?”

“Not in person.” She made eye contact, making sure I knew just when she started looking. Her eyes lingered for several long seconds. I’d lost my erection during her plea for me to stop this and it hadn’t come back yet. Her eyes were back. “It’s cute.”

Stunned, I stood with my mouth open. Did she really call my dick ‘cute?’ Was that… Was that bad or good? It seemed like an insult, but I cute meant you liked it, right?

Leaning forward, I felt her breath against my ear as she whispered. “Doesn’t look five inches.” She had a teasing grin on her face as she pulled away. “Sorry, sorry. I don’t normally say anything. I know guys are sensitive about their dick size.” I’d covered myself and her grin faded. “You have a lovely penis, Isaac. I can’t wait to watch you jack it off.”

How? How the hell could she smile so happily like that? Or say that so easily?

She gestured to the computer. “Shall we start?” She leaned in slightly, giving me a nudge with her elbow. “Starting to get late. Parents might suspect we are up to no good if we spend a lot of alone time down here.”

Near nonexistent chance of that. My parents probably went to bed hours ago.

“Emma,” I pleaded. “I can’t—”

Her expression hardened. “I did this for you, Isaac. I fucked three guys because you told me to. I recorded them doing it, just for you. So that you could have this opportunity to reach Level Four.” She looked hurt. “After I did all this for you, you tell me you can’t?” I said nothing, my head lowering. “Unbelievable. You say nothing when I was pleading with you to end this, yet you don’t even try the quest you accepted. We could have ended this on a happy note. Now we'll end it in failure.”

Sitting down, I felt the warm leather of my seat against my bare ass. Slowly, I rolled myself into position, eyes on the screen.

I could only imagine Emma’s smile as I numbly grabbed my mouse.

“So,” she said with a light and bubbly voice. “Which one are you going to pick?”