After Session Fun

As things usually went, the conversation devolved into random bullshit. Emma was clearly a focus, with Ben and Owen competing for her attention. It was cringe-inducing watching them make fools of themselves. Poor bastards. They didn’t have a chance in hell. I didn’t either, but I still had a step up on them. The picture she had sent me on Wednesday was still fresh in my mind. Even with her fully clothed, I still masturbated to it. It was her smile and the way she was looking right at the camera. It was like that smile was meant only for me.

Jesus. What the hell was I doing with myself? None of this was me, but Emma seemed to drag something out of me.

It was almost three in the morning when everyone decided it was time to go. Ben and Owen lingered a bit longer than the others to talk with Emma some more, but eventually headed out too. Trash bag in hand, I began the slow process of cleaning up. To my surprise, Emma hung around to help out.

“You can go home. I got this.”

“No way. I helped make it, I’ll help clean up.” That instantly elevated her in my mind. Not once had any of the others offered to help over the years.

We worked in silence as we shoved pop cans and paper plates into a trash bag. It was a lot faster with two people. While she finished with the trash, I started putting the dice away.

“Thanks for letting me come tonight,” she said, breaking the silence. “I had a lot of fun.”

“I’m glad. Not going to lie, I was stressing out a lot over how things would turn out tonight. It wasn’t as bad as I feared it would be.”

“Oh?”

I hid behind my DM screen so she couldn’t see me blush. “Sorry about Owen and Ben.”

“Why? It wasn’t your fault. It was kinda cute how bad Ben is at flirting. Owen though is a… character.”

“He’s an asshole.”

“Your words, not mine.” Tying off the garbage bag, she sat against the edge of the table and looked over her shoulder at me. “Still, don’t worry about them. They were fairly benign compared to some guys I’ve had to deal with.” That was hard to believe. An uncomfortable silence settled between us as she stared at me expectantly. I floundered for something to say.

“Thanks again for helping clean up.” God, even I knew that sounded lame.

That mischievous smile was back as she looked down at me. Shifting her weight on the table, she leaned towards me. “I have a question for you.”

“Uh, okay?”

“No, not a question. A question,” she said with more emphasis than necessary. Blinking, my eyes widened as I realized what she was eluding at. This would involve a picture. Mouth dry, I could only nod. She seemed to be enjoying this as her hands settled in her lap. “Did you masturbate to it?”

I knew she was referring to the latest picture she sent me.

Heart pounding, I slowly nodded. This was a hell of a lot harder when she was physically there in front of me.

“Silence isn’t an answer, Isaac.”

“Yes,” I whispered.

Her smile was calm, her tone like she was discussing the weather. “Really, Isaac? That thing?” She clicked her tongue against the roof of her mouth. “It wasn’t even suggestive.” Shaking her head, her blue eyes bored into me. “Please tell me it wasn’t more than once.” Opening my mouth to speak, she interrupted me. “Remember, honesty is important.”

Hesitating, I closed my mouth. I knew my face was red because I could feel my cheeks burning. Why the hell was I subjecting myself to this humiliation again? Oh right, because Emma was offering sexy pictures of herself as bait and dumbass me already had already swallowed the fucking hook.

“Twice,” I managed to **** out.

Sliding off the table, she slowly moved over to where I was sitting. Walking behind me, I felt her fingers trail along from one shoulder to the next. It was like my entire body quivered as tingles ran down my spine. Sitting back down on the table beside me, she let out a long sigh. Her scent was overwhelming this close. She was a few inches from giving me a clear sight up her skirt. My eyes sat there, waiting for her to shift. I didn’t even know if I could see anything. Just the idea of it caused my stomach to twist.

“Not going to lie, Isaac, I don’t know whether to be flattered or creeped out that you can jack off to plain vanilla pictures of me. That seems a bit perverted, don’t you agree?” Shame burned through me as I stared at the DM screen in front of me. “Isaac, I asked you a question.”

“I… I suppose so.”

She leaned closer, looming over me. What the fuck was going on right now? I’d never seen Emma act like this before. Maybe some glimpses here and there, but whatever this was, she was in full ‘on’ mode. I felt like a mouse being toyed with by a bored cat. The cat knew it could end the mouse at any time, but didn’t. Not out of mercy or pity, but because killing it would be boring.

“Do you like masturbating to pictures of me?”

I glanced up at her and regretted it instantly. She was definitely toying with me and enjoying every second of it.

“Y-yeah.” I had no idea why I answered her, but I felt compelled to. Like the pressure weighing down on me was squeezing everything out. She continued hovering for a few seconds longer before sitting back. It was like I could breathe again, a rush of cool air filling my lungs.

Holy shit. That had been intense.

“Well if you are going to do it, we should get you something worthy of the task, don’t you agree?” I was too busy enjoying the rush of being able to breathe normally to answer. It didn’t matter, because she seemed to not want me to answer anyway. The intense version of Emma was gone, leaving only the teasing one I was more familiar with. Her legs swung back and forth as she glanced down at me. Unlike before, this wasn’t the looming presence it had been. “Since today was a bit of a special occasion, I’m going to bend the rules a little bit and let you choose.”

Meeting her gaze, I blinked a few times. “What?”

Her hand trailed over her chest. “Boobs.” It moved down to brush the top of her skirt. “Pussy.” She tapped the side of her butt. “Ass.”

Gaping up at her, my mind seemed to freeze for a second. She was completely serious. My eyes roamed over her body, heart racing as I struggled to keep my breathing steady. She weathered my lewd gaze passively, expression calm as she waited for my answer.

Why was this so torturous? I had seen countless naked women thanks to the internet. Some were women that were every bit as attractive as Emma was. Yet the thought of seeing Emma naked caused my mind to seize, overloaded by tense excitement.

Watching her sitting there beside me, I knew the answer to her question. It was the only one I wasn’t allowed to give. ‘All’ would break the rules. I had thought it was strange when she mentioned the whole choice thing. Now, it was starting to make sense as more of her personality came to light. This was all a game to her, a game designed for her amusement. Even though I was getting what I wanted, it wasn’t all of what I wanted.

“I know it’s a difficult choice, but you are going to have to choose,” she whispered.

My heart hammered as I met her eyes. It took me a few times to find my voice. “Boobs.”

A sweet smile graced her lips. “Excellent choice.”

Hopping off the table, she walked around the table. “This was fun, Isaac. I look forward to next week’s session.” She hesitated at the corner, turning to face me. “I don’t know if I’ll need any help this week. You going to be at the library?”

I nodded numbly, still suffering from the dizzying effect she had on me. “All week,” I managed.

“Sounds good. I’ll find my way out then. See you later, Isaac.” It seemed like she put a bit more emphasis on my name when she said it. With a smile, she turned and left.

Taking a deep breath, I sank back into my chair. There was a slight tremor in my hands as I struggled to calm down. No idea what was wrong with me or why I reacted that way. It wasn’t about what she asked, but how she asked it. The tone of her voice, the way she used her body, the confidence she had in herself. It was clear I’d failed every Will save tonight. It was a bit unnerving to see how easily Emma morphed between the lighthearted teasing version to this sexualized vixen. That wasn’t what worried me though.

My reaction was frightening. I’d never been so stressed in my life, yet I found I didn’t hate the feeling. At the time I did, but now that things were cooling down, I found the whole thing a little exciting. Twisted and wrong, but exciting at how unpredictable it all was. Instinct was warning me that this was dangerous, but I didn’t seem to care that much. No one was getting hurt. Sure, I had to endure some embarrassment, but that was a small price to pay. The reward made it worthwhile.

Calming down enough to clear my thoughts, I glanced down when I realized I wasn’t the only thing excited by all the sexual tension. Taking a deep breath, I leaned back in my chair and rubbed my hands over my face. Ugh. What happened to the simple days where this could be taken care of with a few minutes of browsing? Find a video of some hot girl, watch her getting railed for a few minutes, done.

In fact, that’s exactly what I would do. With steeled determination, I headed to my room where my PC was. I went through the motions, going to my favorite site and getting prepared. Progress stalled as I examined the categories. There were so many possibilities. Endless girls to watch. Chewing my lower lip, my eyes hovered over my popular categories. Lesbian, college, threesome, teen, PoV… They all sounded good, yet they seemed… blah. Some of the teaser clips looked interesting, but I made no effort to click on them. I just scrolled and scrolled.

My determination began to fade as I found myself navigating to another site. Opening the drive account I’d created recently, there was a single folder inside. Clicking it, I found the pictures waiting for me. Something was definitely wrong with me. I had unlimited objectively better porn at my fingertips, and yet I was jerking off to pictures of my friend.

God damn it. Maybe she was right. Maybe I was a pervert or something.

None of that mattered at the moment though. All I could do was stare at those pretty blue eyes and smiling face as I pumped my cock. I couldn’t believe it. Emma was so fucking hot, and she was right there. It was almost like I could remember the faint remnants of her perfume. The soft feel of her hand in mine. The way she sent shivers down my back when she ran her fingers across my shoulders. The soft echoes of her laughter.

Above all, I remembered her many smiles. The teasing ones she gave me when she caught me staring. The mischievous ones she had when she asked me something embarrassing. The amused ones she had when she was enjoying herself.

Letting out a soft grunt, I exploded into the waiting tissue paper. In front of me was the first picture she ever sent me. The way she looked at me through the picture, like she knew what I was doing and was calling me out on it. As the euphoric rush faded, I was left with shame and guilt. Even though Emma seemed to want me to do this, it still felt wrong.

“Fuck,” I whispered with a sigh.

Closing everything down, I got up and headed for the bathroom. Even though I had jacked off, I was still feeling antsy. I needed a cold shower before bed.