Increasing Stakes

I knew what to expect after we went our separate ways. Sure enough, a half-hour before midnight I got a text telling me my photo was waiting for me. Her proof that she was holding up her end of the deal. Zach—whoever that was—took the photo. That wasn’t the important part. The picture he took was magnificent. It was at a slight angle looking up at Emma. She was leaning backward, a big smile on her face as she stared down at the camera. My eyes ate up the little details. The way her smile was all-natural and touched her eyes. How her pink nipples stuck out from her pert breasts. The sexy curves of her body.

My breath picked up as my eyes crept lower and lower. It was almost as if my brain was keeping the eyes away from what I really wanted to see. With a pounding heart, I **** myself to look down. The neatly trimmed black hair guiding my eyes down to what a part of me was demanding to see. I could see the base of the pink condom Zach was wearing. Everything else was missing, buried deep within Emma’s pussy.

The degenerate in me lost it. It took me nearly five minutes to calm down enough to look again. Emma had kept her word. She told me she was going to fuck him, and that’s exactly what she did. This hit so much harder though. She’d slept with tons of guys already one more should have meant nothing. This was different. I was involved in this, even if it was indirect. She had asked how it was going to happen, and here she was doing exactly what I told her.

What really made me lose it? She had titled the file, “Thinking of You.”

I stayed up way too late abusing my cock as I wrung every drop of cum I had.

If this was what awaited me in Level Four, I don’t think I was going to make it. Emma knew how to push my buttons and she wasn’t afraid to **** them. As much as that excited me, it was exhausting. We met twice more that week and twice the following. Four more pictures with three being from her night with Zach. The last one had been a curveball to remind me there were other guys she was sleeping with. By the time the weekend rolled around, my poor dick was sore from all the attention it was getting.

At least the session went well. In a rare feat of competence, Owen managed to get a good lead that would take the party towards an important location where they would get more information on the wizards they were hunting. I was grateful for it because now I didn’t have to make up some bullshit side-quest stuff to ****-feed them the information. I already had most of the encounter set up so it was all a matter of fine-tuning what I had.

It was only twelve-thirty when the group broke up. Like usual, Emma remained to clean up the mess the others left behind. Once things were cleaned up, I found myself in the familiar position of looking up to the beauty who haunted my life. She was no longer the distant Emma either. Gone were the days of her sitting atop the table in front of me. Now she used me as her seat. Straddling my legs, she rested her arms against my shoulders as she stared down at me.

“Are you enjoying your photos as much as I had taking them?”

I nodded numbly as I struggled to maintain some sense of composure. Her closeness was making it damn near impossible. She smelled heavenly and her boobs were right there in front of me taunting me with a look-don’t-touch attitude. In a rare surge of bravery, I managed to put my hands on her waist. She said nothing so I didn’t dare move them in the hopes she would forget they were there.

“Say it,” she whispered.

“I am.”

She smiled, but there was no warmth in it. I braced myself as I anticipated her need for blood. “You masturbate to them?”

“Yes.”

“Tell me how many times you used them.”

I had no idea, so I didn’t give her a number. “Enough to make my dick hurt.”

She blinked a few times, her normal expression returning. “Seriously?” Her voice had dropped the teasing vixen edge.

“Uh… yeah.” I winced as she shifted her position on my legs. She wasn’t sitting near it, but it moved my pants enough to rub against my sore erection.

“You really are a pervert,” she whispered. It was soft enough that I don’t think I was meant to hear it.

“What?”

“You like seeing other guys fuck me that much?”

Her casual tone had me on edge. Were we still in that weird play or…?

“It’s no different than jacking it to a porn star.”

“This is totally different.”

I frowned. “How so?”

“One, I’m not a fucking porn star.”

Debatable, but I was smart enough to keep my fucking mouth shut for that one.

“Two…” She said nothing at first as her clear blue eyes stared down at me. I thought she was dragging it out on purpose, but I think she was having second thoughts. That wasn’t necessarily like her, especially when it came to me.

“Two…?”

That seemed to be the nudge she needed, but she didn’t continue as I thought she would. “Do you still like me, Isaac?”

“Yeah.” I didn’t even need to think of it. Having her sitting here like this clarified a lot of things. My love-hate relationship with this play of ours aside, I still enjoyed our moments together outside of this. It helped she was absolutely gorgeous and well outside my league. Honestly, there was a relatively high chance that I could score someone on her level. Money had a way of lowering standards if you could throw it around. That was one of the reasons why I liked Emma. She didn’t seem to give a single fuck about how much money my family had. All she cared about was the little moments like this where she could run wild on my emotions.

She tilted her head slightly. “Even after all the shit I put you through?”

“Even then.” I managed a grin. “Probably aren’t far off with the pervert thing…”

“Hypothetically speaking,” she started, keeping an even tempo as she spoke. “Would you date me?”

I saw where this was going. Oh man. This was going to hurt. A lot. I took a deep breath as I prepared myself for whatever horror she was going to bring down on my poor heart. I offered it anyway. “In a heartbeat.”

“Even if I continued fucking other guys?”

I clenched my teeth and nodded. I don’t think I had enough in me to answer her anymore.

“Even if I demanded you be faithful to me?”

My nod was smaller this time.

“Interesting,” she breathed. I could see the wheels turning in her mind. What the hell was she up to? I didn’t dare speculate. I knew what hope would do to those thoughts. The last thing I needed was to make whatever she was cooking up worse.

Her eyes focused on mine. My eyes went wide as she shifted again. This time, she moved forward to settle painfully on my erection. There were numerous layers of clothing separating us, but she was definitely resting her pussy right atop my hard cock. “I’m taking things to the next level.”

The little movements she was making were driving me wild. I didn’t know which was more intense, the pain or the pleasure. Really regret all those late-night sessions with those photos now. If it weren’t for them, I would be in pure bliss right now.

“There’s a Level Five?”

“Huh? No. Not what I’m talking about. After how close you came to failing your level-up quest, I was concerned about how you would react to Level Four but you’ve acclimated better than I thought you would.”

“Thanks?”

That smile of hers was back. “You fell for me pretty hard, didn’t you?” I didn’t say anything. I didn’t know what to say. Confirming it would achieve nothing more than giving her more ammo. Not that she needed more considering all the other stuff she did to me.

She leaned closer. Close enough that I could feel the warmth of her breath against my lips. Close enough to kiss. It would have been easy to do. An inch. A half-inch even and our lips would be touching. I wondered how she would react to that.

I didn’t. As much as I wanted to, I was more curious about what she was planning.

“I’m changing a rule,” she whispered.

“What?” Faces this close, it was impossible to see what kind of expression she had.

“Feelings are no longer against the rules.” I winced as she ground herself against my erection. Pleasure and pain in equal measure, just like Emma. “I want you to like me, Isaac. I want to see how deep these feelings you have for me are.” She hadn’t been kidding about kicking this up to the next level. Not once in all this time together had I experienced such an intense atmosphere. It was oppressive. The way she stared at me. The gravity in her words. It sucked me in deeper. She was breathing faster. Despite the intensity of it all, I’d never seen her so excited. “I want to fuck men while thinking of you. I want to scream their name as I cum on their cock knowing you care for me more than they ever will.” Emma was practically panting as she continued to rub herself against my erection. A moan escaped her. An honest to god moan. It didn’t deter her from her current action. If anything, it emboldened her.

“I want you to care for me with everything you have. I want you to care while men who don’t use me in ways you’ll never experience. I need you to know that. To know that your wonderful, beautiful feelings will never be more important than the cock of a stranger.”

Horrified by what I was hearing and in pain from her vigorous grinding, I pulled my head away from hers. I could stop this. A simple word would tell her she was going too far.

But it was too late. We were far too deep in the Hell of our own creation for me to ever escape.

She kissed me. This wasn’t the playful peck on the cheek but a full lip-on-lip kiss. Her tongue **** its way inside my mouth, destroying any misunderstanding that could arise from this situation. This wasn’t a pity kiss. It wasn’t a playful peck between friends. There was a weight there. Dangerous emotions neither of us should have. This wasn’t acceptance of my feelings for her, it was a demand.

It wasn’t a one-off either. I don’t know how long this sudden make-out session was, but I knew exactly when it ended. Between the intensity of her words, the kissing, and her grinding herself against my cock, I jerked back as my sore cock had the most awkward orgasm in my life.

She knew I came too because that was when she finally gave me the space I desperately needed. She made a show of wiping her lips, a half-cocked grin on her face. Her eyes lingered as if enjoying her handiwork. I was an absolute mess of a man. Between the painful throbbing of my cock, the sickening wetness of the cum in my pants, and the whirlwind of emotions running through me, this was the worst off she’d left me by far.

And then it was over.

She lingered there on my lap. The overwhelming confidence had faded as she looked me over. “You okay? I think I lost it a little there.” There was a breathlessness to her voice. Even though she was returning to normal, I could still see the untamed excitement that glimmered in her eyes.

“Sore,” I managed. I wanted nothing more than to change. If I didn’t move, the sticky heat in my pants wouldn’t bother me.

Okay, that was a lie. I desperately wanted a change of pants.

“Was I too rough?”

I shook my head. “More like… suffering from overuse.”

An amused smile touched her lips. “You weren’t kidding.”

“That’s what I said.”

She lifted herself off my legs and moved away. “Well,” she said with a deep breath. “Tonight was… yeah. I should get going.” There was something in her voice that was off.

“Emma, wait,” I said as I stood. I winced at the wet feeling in my pants. So gross. She hesitated and I dug up all the courage I could muster. “You can’t just take off. Not after that.”

She was unusually fidgety. “We can talk on Monday.”