Cowgirl

Cowgirl.

This one seemed more Emma. On top and in control. I had a feeling this would be the most intense of the three. The other two, the guys would be doing most of the work. This one was all Emma.

The thought of that resonated with something inside me. I figured it had to be the nerves and anxiety about this quest messing with me. I was about to watch Emma ride some guy's cock and jack off to it. All while the girl herself watched me do it.

It was the reason I picked this one. The more intense, the better, right? There was a time limit, so I needed something exciting to get me off. Watching Emma in her element might be the difference between failure and success.

Hands shaking, I went for my headphones. I stopped when Emma’s hand rested on mine.

“Speakers?”

“But…”

“It’s not any fun if only you can hear.”

I had to adjust the settings, but I begrudgingly turned my speakers up. Not a lot. Even if we were downstairs, Emma had a point about my parents. They usually left us alone when I had people over and they were asleep this time of night, but her presence threw that up into the air. Having the door locked together in my bedroom was already a bad look. Hearing moaning and grunting before that…

“Remember,” she said as I went to open the file. “You have to finish before the other guy.” She grabbed my shoulders, giving them a squeeze for encouragement. “Not going to lie, this is probably the hardest of the three. The video is only six or so minutes.”

“Wait. Maybe I should—” Not much time to react to that as she reached over and started the video. Audio kicked in through the speakers as the video snapped on. My breath caught at the sight of a fully naked Emma on screen. She was staring right at me and I realized immediately how this was going to go down. The guy she was with was the one holding the camera, giving the entire thing a PoV feel. My jaw clenched as I saw her cute little smirk stare down at the camera.

“You ready?” Past Emma whispered.

“Y-yeah,” the guy groaned. He sounded nervous.

“Shh,” she said, reaching forward. I assumed she was placing a finger on the guy’s lips. “I told you no talking while recording.”

“S-sorry.”

“The guy was a bit of an idiot. This was our first time together, so he was a bit nervous.” I jumped at the sound of her voice beside me. She wasn’t looking at me though, her eyes transfixed on the screen. “Oh! Watch.”

My head swiveled over to see the view had shifted. Emma’s upper body no longer dominated the shot. No, it was her lower half now. She was raised over a long but sorta thin cock. Her hand was wrapped around the base of the condom he wore as she guided it to her entrance.

“Are you watching?” I glanced over to find Emma’s gaze locked on my face. “Don’t look at me. Look at the video!”

Eyes snapping back to the screen, I watched as the tip of his cock pressed against her glistening lips. Holding my breath, the world seemed to spin as I watched. A moan came from my speakers as the cock slowly disappeared inside her.

“Oh god. That feels so fucking good.” Her voice was soft and throaty. She was making small movements with her hips, grinding forward and side to side. A few seconds later, she lifted herself up a tiny amount before sliding back down. My eyes were like a laser sight. All my attention was on the condom—as if that was the offending cause of this feeling inside me.

The camera didn’t move from that view as Emma’s movements increased. Heavy breathing came from the speakers along with the noise of her movements atop him.

“Um…” I jumped at the whispered voice against my ear. Emma was leaning over the back of the chair, her lips near my ear. “Not trying to tell you how to complete the quest or anything, but you probably should start…” At the same time, her hand appeared in my vision, the fist moving up and down. My eyes found her face, but she wasn’t concentrating on me or the video. Instead, she was pointedly staring at my crotch. More specifically, the erection I was sporting.

The shock was like a hit over the head. I was rock hard, straining in a way that was only achieved by peak arousal. Astounding to be like this without a single touch.

I’d been driven mad. Could you be crazy if you knew you were crazy? I think that was a book or something. My attention focused on the video. The man had tilted the camera up so that her face was staring down at me. There was a smile on her face, excitement in her eyes. Lips parted slightly, she was still breathing hard. She had a forward lean, her hands seemingly resting on the guy's chest. There was a shift in her expression like she was fighting back moans. The way her upper body was swaying, I think she had increased her pace.

As her pleasure-filled face filled the screen, my hand was rapidly sliding up and down my dick. It was the most surreal experience. This wasn’t like jacking off to porn. Porn had a fantasy element to it. Watching a hot girl with a guy while thinking, “I wish I was fucking that hot girl” sort of thoughts. This was something else entirely. This wasn’t some porn star. This was Emma. Emma’s breasts were right there on the screen. The camera dipped down to show me her riding that long cock. The way her wet pussy lips seemed to grip his cock as if not wanting it to leave.

Then there were her facial reactions. The intensity there was electrifying. Her soft moans danced through my head, the rhythmic beat to my pounding heart. This wasn’t her getting fucked by some guy. She was making it clear that she was doing the fucking here. Emma was in control. The pleasure she felt was her doing. Something she wanted. The man was a tool for her pleasure, and she was enjoying every moment of it.

Listening to the little sounds she made as another man gave her pleasure was making my head light. Not once did I wish to swap places with the guy in the video. That’s how I knew I’d fallen off the edge and there was no hope for me escaping this crazy train. The hope that had burned endlessly since we started this whole thing hadn't gone away. The unending hope I would get my turn with her.

A feeling separate from that desire had taken hold. It was something that had been growing ever since her pictures became more explicit. I wanted to see Emma with a man—even if that man wasn’t me. Now that I was actually seeing it, I was **** to come to terms with what I had been dancing around this entire time. Emma was screwing some dude—enjoying it even—and it was god damn hotter than hell. It had to be considering the part of me horrified at what I was watching was being boiled into silence.

I was struggling at the halfway point. Emma’s small gasps of pleasure had turned into passionate cries. The small movements she had been making before were long past. The guy was having issues holding the camera still as the bed rocked below him. I caught brief flashes of her face. Camera forgotten, it was about the pleasure now. Firm breasts shuddered and swayed from the **** of her wild ride.

Words floated through my speakers. Words that explained how great she felt. Words that expressed how much she was enjoying this. Words that described how big he was and how deep he was inside her. And I knew that none of what she was saying was for the guy’s benefit. No, she had made this video specifically for me. All this talk about the guy’s big cock or how it filled her up was meant for me.

It was those words that cut the deepest because they reminded me who was in the video. Emma. The Emma I had grown to care for. The Emma I befriended.

The Emma I liked.

With that thought, I began to lose my erection as clarity chipped away at the mental fog that encompassed me. In a heroic effort by logic, it had pushed aside the lust and arousal long enough to worm thoughts into my mind. What was I doing? This was wrong.

“What’s wrong?” she asked as I let my hand fall away from my softening erection. “You don’t have much time left.”

“I can’t.”

Her hand touched my wrist, bringing my hand back to my dick.

“You have to.”

I looked up at her, shaking my head. “I can’t. I’m sorry.”

She stepped around the chair, lowering herself so her head was level with mine. “Please, Isaac. I need you to do this.”

“This is wrong.”

“How?”

“I… I don’t know. It just feels—” I lost my words as her hand brushed against my cock. The unexpected touch combined with the sounds of her wild ride temporarily reversed my softening erection. Her hand found mine and set it against my erection, forcing my hand to wrap around it.

“I can’t help you more than this,” she said sadly. The way she was looking at me tugged at my heart. There was almost a pleading. “You have to do this yourself.”

“Why?” I whispered, unable to escape the sound of her moans coming from the computer.

She gave me a hurt expression, but I was confused as to why she was hurting. I was the one who was an emotional pincushion, yet it was her expressing pain. Her next words could barely be heard above her other self’s impassioned cries. “Because I like you too.” Before I could react, she was pulling away. “If you fail this, it all ends.”

Her last words barely registered. All I could hear was her saying, ‘I like you too,’ over and over again. A never-ending echo of her confirming that there was something behind all this madness.

She liked me.

Emma liked me.

My eyes focused back on the screen to find the girl who liked me losing her mind as she rode this unknown man’s cock. My thoughts drifted somewhere else. That brief kiss before break had meant something. I hadn’t been crazy—well, not completely. My heart was a torn mess. She liked me yet there she was fucking another guy. Not just him, but two others from the other videos. She did that… because she liked me.

Sorry logic. I'm going to need you to take a seat for a bit.

I embraced the insanity. I beat off furiously like this was any other thing she’d sent me. I took pleasure in the sounds of her pleasure-filled coos of how wonderful she felt. The noises she made as she repeatedly brought herself down on that long cock. I did it because I enjoyed it. All of it. The hurt was nothing compared to the pleasure moments like this brought. If anything, the little bit of pain made the pleasure that much better.

So I beat off to her fucking another guy. I let the sight of it all consume me as I felt my orgasm grow steadily closer. I wanted to cum. I wanted it more than anything not because I wanted to get off, but because I didn’t want this to end. Fuck my broken-ass brain. I was committed in my journey with Emma to see just how deep Hell went.

My chest heaved for air as I slunk in the chair, completely spent. Not necessarily physically spent, but rather mentally and emotionally exhausted. There on the screen, Emma was encouraging the guy to cum as she cried out about being close too. I closed my eyes as I tried to ignore the swirling maelstrom of emotions inside me all while listening to the man grunt loudly. He was cumming. I knew he was cumming because Past Emma was telling me it was happening. The man Emma was fucking was cumming and all I felt was relief. Relief because I beat him.

I completed my quest.

I felt her hand on my shoulder and I didn’t move. My emotions were all over the place and I couldn’t see her right now. I knew I was a mess. I hadn’t had a tissue or anything, so my cum had made an absolute mess of me.

“Welcome to Level Four.”

Her hand left me and I soon heard the door open and close. Opening my eyes, I scanned the mess I’d made. Fuck. I needed to clean up. Reaching up, I was about to close out of the video when I saw it was still going. The guy was no longer holding the camera. Emma’s face filled the screen, a big smile on her face as she pulled the hair from her face. Winded and a sheen of sweat on her skin, she looked every bit—no, even more—mesmerizing than she was wearing full makeup.

Her eyes locked right on the camera. Right on me.

“I hope that was as good for you as it was me.”

“T-that was incredible,” the guy said, mistaking her comment as something directed at him. “C-can we do it again?”

She didn’t say anything, smiling that damn smile of hers as she held my gaze. Her mouth opened to answer when the video ended.

My head hit the back of my chair as I closed my eyes again. “Yeah… Yeah it was.”