First Quest

“Sit,” she commanded, patting the top of my computer chair. I had no idea why we were in my room, but I was extra nervous now that she had closed the door. And locked it.

It wasn’t the fact that I was dangerously close to a bed with a super hot girl. Normally, that would be cause for excitement. Right now, I felt like a creature locked in with a predator looking at its next meal.

I sat in the chair, looking up at her wondering what she had planned. Standing in front of me, she wore that coy little smile of hers. Before I could react, she straddled me. My body instantly went ridged as I felt the weight of her press against my legs. A quick wiggle to adjust her position to a more comfortable one. The heat flooded over my legs as I stared at her.

“Now,” she said with a perfectly calm voice despite our intimate position. “This is part one of a two-part quest. Victory here determines if part two is a solo or group quest.” No idea what that meant, but I listened as she continued. “The game is simple. I call it ‘Will-She-Won’t-She.’” She held up a coin. “I am going to position the coin in secret. Heads means yes. Tails means no. I’m going to ask you things and you are going to answer each question with a yes or no. I’ll reveal the coin after each one. Get it right and complete the quest, you can do each and every one I say yes to. Get it wrong, it counts as a strike. Three strikes and you fail the quest and get nothing—even the ones you previously got right. This is an all-or-nothing game.”

Oh, this was going to be trouble. I fought to keep myself calm, failing miserably in the process. “And how do I win?”

“Get seven of them right.”

“Seven!”

She nodded. “I told you this was going to be hard. So? Shall we start?”

I let out a long breath. It was hard to think with her so… close. Her breasts were almost right there in my natural line of sight, which was not helping. Worse was her sitting on my legs. She wasn’t heavy, but her being in such a compromising position… A little more and she would be right on my crotch. Every breath I took was filled with her perfume. It was either stare at her chest, or stare at her smiling face. Not sure which was the better option.

I nodded, doing my best to steel myself.

And to stop my erection from growing any more than it had. I swear she was moving on purpose, inching teasingly closer yet remaining agonizingly far away.

With a smile, she hid her palm while she messed with the coin. When she was done, she rested her hand atop it and looked at me. “First question. Will I let you remove my shirt tonight?” My eyes immediately went to the blouse she was wearing. She leaned forward slightly, a teasing glint in her eye. “That includes the bra,” she whispered.

My eyes lifted to meet hers as she returned to her normal position.

Calm down and think. She was trying to rattle me and stop me from thinking things over.

I hated how damn good she was at it.

“Yes.”

Off her hand went, revealing heads. I let out a long breath, not realizing I’d been holding it there in that brief moment of reveal.

“Huh,” she said as if surprised. “Off to a good start.” She went back to hiding the coin as she switched it. Or had she? “Keep it up and you might get to see them for real.” Her eyes flicked down. “I see someone is excited at the idea.” A teasing laugh followed as I felt my cheeks burn.

“Now,” she said with a deep breath. “Will I let you fondle my breasts tonight?”

Fuck. Me.

My gut reaction was to answer yes, but I stopped myself. This wasn’t about what she was willing to do. Not really. Her goal here was to fail me, not get me to admit what I wished I could do to her. She was going to try to trip me up and this was a perfect time to do it while I was too flustered from the first one to think over things.

“No.”

“You sure?”

“I’m sure.”

Shrugging, she revealed the coin.

Heads.

“Shame. That’s strike one.” I barely heard her, staring at the coin. Had she predicted what I would most likely answer? Her expression shifted to a pout as she hid the coin again. “What makes you think I wouldn’t let you play with my tits after making the effort to show them off? Or do you not want to play with them?”

“I—”

“You a big boobs man? Are my boobs too small to interest you?”

“That’s not—”

“Next question,” she said, resting her hand atop the coin. She was fucking with me again, throwing me off. These were fifty-fifty questions. Thinking them over was pointless. I had no idea how her mind fucking worked and trying to understand it was pointless. From now on, I had to go with my gut.

“Will I let you undress me completely tonight?”

“Yes.”

Heads. I breathed out in relief.

“Interesting. Interesting,” she said with a smile as she reset the coin. “Next question. Will I be giving a striptease tonight?”

The last question was having me undress her completely. If she was stripping herself, then I wouldn’t be able to do that.

“No.”

Sure enough, the coin was tails.

She didn’t seem as playful as I thought. “I thought I would get you with that.”

“Maybe if you asked it later…”

“Damn,” she muttered as she hid the coin again. “Okay then.” Her grin was back. “Will I be showing off my bald pussy tonight?”

Emma had a small strip of hair above her pussy. I knew that because I’d seen the pictures. It was consistent through all of them. But had that changed? It had been some time since I last got a photo to confirm it. It would be like her to shave knowing this was coming up.

“Yes.” Immediately after saying it, I wished I had said no. “Wai—”

Tails.

Fuck.

“Strike two,” she said with a frown. “Really now. That was an easy one, Isaac. Are you trying to fail?”

Groaning, I ran my hands over my face. What was wrong with me? I needed to focus.

“Question six. Will I be kissing you tonight?”

Don’t think. Just answer.

“Yes.”

Heads.

She was grinning. “Tonight is going to be pretty exciting, don’t you think?” I didn’t answer, my heart slamming against my chest as I stared at her lips. “Question seven.” Her voice lowered as she lost her smile. Her blue eyes locked with mine, not giving them permission to look away. I almost forgot to breathe under their intensity. “Will I need a condom tonight?” The whisper of her voice sent a chill down my back.

My body was quivering. There was no stopping the erection I was sporting as it painfully pressed against my pants. All I could focus on was her eyes. Their need for an answer.

“No,” I whispered back.

She didn’t say anything. Didn’t move. We stared at each other in silence.

When I looked down, I found tails.

I felt sick. Of course not. Why? Why did I even hope—

“Eight.” Her voice was still in that low whisper. She wasn't giving any time to process things. “Will I be taking your virginity tonight?”

“Yes.” My answer was a breath of air with no thought behind it. My mind was barely functioning as I stared into her eyes. Was her face closer than before? It was. The world was thunder as my heart beat the drums in my ears. By the time I realized what I had said, it was too late. I knew immediately I’d lost. Such as a stupid fucking way to lose. The question before had been the answer. She had said she didn’t need a condom tonight—

Heads.

My eyes shot up. Her expression never shifted. It had the stoic professionalism I was used to whenever she was getting serious about something. A perfectly controlled mask with zero emotional leakage.

“Will I allow you to cum inside me tonight?”

I was two questions away. Two questions to get my seven and Emma and I would…

Focus. I needed to think. She wasn’t going to let me cum inside her, right? Jesus. I was going to have sex with Emma. She had come out and said it. Tonight. My first time. Emma was going to take my virginity. She would too. This wasn’t her messing with me. Not like that. I could see it in her eyes. She was absolutely committed.

But without a condom? She’d want me to pull out, right? Or was she on birth control? She had to be on birth control with how… active…she was. Or maybe other guys used condoms? So her not using condoms with me…

God damn it. What the fuck was I supposed to answer here? Fifty-fifty. An utter crapshoot. The idea of messing up now—

Fuck. If only I hadn’t completely botched the answer about her shaving her pussy.

“Yes.” All I could do was roll the dice. Based on the fact that she was willing to mess around without a condom, I had to assume she was on birth control. With everything else she was agreeing to do, this seemed in line.

Tails.

I barely had time to see it before she was pulling away. Instantly, I missed the heat of her body near mine, the weight of her against my legs.

“What, you think that just because I’m nice enough to let your first time be without a condom you can just blow your load inside me?” Her expression wasn’t anger, but disappointment. “Strike three. Quest failed.”

“Emma—”

“Tonight could have been special, but no. You had to get greedy.” Her hands pressed against her hips. “You’re lucky I’m nice enough to let you take the second quest.” She let out a huff, shaking her head. “And you’ll have to do it solo too. That’s going to make it harder.”

I was still in shock. A coin flip. A fucking coin flip. I didn’t know if I wanted to scream in anger or break down and cry. Instead, I leaned forward and focused my breathing. I was on the verge of hyperventilating with my rapid fluttering heart.

“Would you have done it?” I asked after collecting myself enough to speak. My voice sounded hollow. So close. So fucking close and I had no one to blame but myself.

“Hmm?”

“Any of it? Is any of this real, or is this all Lucy and the fucking football? You set the football there, tempting me, then pull it away at the last second.”

Emma said nothing, towering over me as I bent forward in my chair. Moving in front of me, she stuck her hands out in front of me.

“Hands,” she ordered. I looked up. “Give me your hands.”

I placed them in her palms and she stepped back and pulled me up out of the chair. Facing her, no words were exchanged as she rotated my hand to be palms out. Holding each tightly, she guided them to her breasts. My automatic reaction was to grab at them.

Holy shit. I was touching Emma’s breasts.

They were—

Before I could really register, she pushed them away. My eyes lifted to meet hers. “But I didn’t even win that,” I said softly. It was lame, but my mind was trying to record every second of sensation my hands had reported and wasn't doing much else.

“Yeah, and I let you do it anyways. If I let you do something you didn’t deserve, why would I stop you from claiming what is owed?”

I fell back into my chair.

“Fuck.” I buried my face in my hands. I had been so close. So close.

“Wow.” There was a coldness in her voice that made me look up. The mask was back, but her eyes showed all I needed to see. There was a cold disappointment that matched the blue of her eyes. “You were that **** for me to have sex with you? Here I thought you liked me, but you just want what every other guy wants.”

“That’s not—”

“Fine.” I stopped mid-sentence.

“What?”

“I’ll let you.” Her eyes shifted, looking to my bed before settling back on me. “Take me to bed. Use me as you want. I’ll even let you cum inside me.” I said nothing, stunned as I stared at her. My eyes slowly drifted down her body. Was she serious? “Once you are finished with me, we are finished. No more games. No more pictures. No more studying.” She said nothing, waiting for me to respond. I was still too flabbergasted to say anything. “What? That’s why you’re doing all this, right? You want in my pants, well, this is your chance.”

“I—” I had to **** the lump down my throat. A slight upward tilt of her right eyebrow. Looking down, I let out a long breath. “I don’t want that.”

“Now you’re being confusing, Isaac. So you don’t want to sleep with me?”

“That’s not—”

“It sure sounds like it to me.”

“Damn it, Emma! Stop! Just... stop!” I pressed my hands to my temple. “You are twisting everything I say. You damn well know what I mean! I want to sleep with you. I want to sleep with you because I like you.” Breathing hard, I looked up to meet her gaze. “I like you, Emma.”

She wore a neutral expression as she stared at me. “You know that’s against the rules.”

“I don’t care.”

“You should. The rules are there for a reason.”

“I don’t care. I like you, Emma. Even though you are fucking twisted—” Stopping, I ran my hands over my face. I took deep breaths to stop the tears. “I really like you. Even though I shouldn’t. I do. I really do.” My voice was muffled from my hands, but I didn’t want her to see my face. To see the complete mess I was. The mess she was making of me.

“Isaac.” That voice. So soft and warm. I felt her hands rest against my legs. Peeking through my hands, I found her squatting in front of me, a concerned look on her face. Emma was there. The Emma I talked to in the library. The one who laughed and joked around with the others. “Shall we stop this?”

“What?” My voice cracked over a single word.

“You have lasted far longer than I ever expected, and I have enjoyed our special time like this... far more than I ever expected, but don’t you think it’s time to end this? I care about you.” She gave a humorless chuckle. “I know it doesn’t seem like it, especially now, but I really do care about you. Even after all the shit I put you through, you somehow still continue to be my friend when I don't deserve it.” Her throat tightened and I felt her grip on my legs tighten. “I want that to continue. I want to play DnD with you and your weird friends. I want to study together in the library. To talk and joke around.”

Her eyes met mine. “This isn’t going to stop until you tell me. I—I can’t stop. Not until you tell me.” There was something in those blue eyes of hers. Something I couldn’t quite grasp. Her hands were gripping at my leg in desperation. “Please,” she whispered. “Tell me to stop. Really stop. One word, Isaac. One word and I’ll stop.”

All I could do was stare at her. This was no act. She was desperately pleading with me to **** her to stop. I didn’t doubt her words that she cared about me. Somewhere in this twisted affair, we had become actual friends. It was fucked up considering there was nothing healthy about this relationship of ours. Emma was pure chaos and I was a man of order. Oil and water got along better than we did, yet here we were.

Even now. Even after all this shit she had done to me, was planning to do, I still liked her. There was zero reason for it. Sure, I was infatuated with her. She was hot, and lust was certainly involved in some of my decisions, but this went beyond that. No one, not even one as hot as Emma was worth all the ****.

So why? Why the fuck was I doing this? Letting her do this to me?

And there sat my answer, right there in plain sight. Because I liked it. She was the storm that rampaged through my perfectly crafted garden that was my life. Everything was perfect and predictable. On the spectrum of happiness and sadness, I figured my life peaked at two happiness and likewise experienced two sadness. Until Emma came into my life, my days were a blur. A routine that never deviated. Never changed.

Emma was a rollercoaster of highs and lows. I never could see the twists coming and never knew where she was taking me. All I could do was hold on tight and see where the chaos took me.

So I said nothing. I said nothing because I didn’t want to stop. She would come in and destroy my garden, and I would set it right again. Over and over. No matter how many times she destroyed it, no matter how she managed to do it, I would always rebuild my garden. Not because I wanted to have the perfect garden. I’d had that most of my life. The perfect garden does nothing. It sits there, perfect and unchanging. But rebuilding it? I was doing something. While there were plenty of ways to bring excitement to my life, Emma was the one here in the moment.

Shit. Maybe I was the fucked up one, not her. She was as trapped as I was.

Somewhere in the long silence, Emma realized I wasn’t going to say it.

A single pained look.

A single moment where she closed her eyes to avoid looking in mine.

Then she was back, her hands withdrawing from my legs as she took a breath.

Her voice was serene, devoid of the emotion that had been there moments ago.

“Are you ready for your second quest?”