Using my new found knowledge

I resisted the urge to confront Emma and ask for the chance to level up more. I couldn't afford to raise her suspicions in any way.

It was a couple of weeks later when Emma approached me after our D&D session. Owen couldn't make it, and Mike was being more irritable than usual and stormed off after rolling snake eyes, so we called it an early night.

"Hey Isaac," Emma said. "Are you still enjoying the pictures?"

"Of course," I replied. The last couple were ones that I had already taken from her phone, so that was a bit frustrating, but I turned away so Emma couldn't see the disappointment in my face. She must have heard something in my voice though.

"Sounds like they aren't quite satisfying you anymore," Emma smirked. She leaned in closer and whispered. "You ready for more?"

That got me attention. I turned back to her. "W-what do you mean?"

"You want to level up again?" Emma asked. "Rewards will be upgraded to occasional physical contact. Nothing major, but maybe a kiss, or I might let you touch my ass. Oh, I forgot, you're more of a boobs guy."

"What do I have to do?" I asked a little hesitantly.

"I have to admit, I was impressed with your dick last time. I'm tempted to have you pull it out and masturbate in front of me." Emma replied while looking down at my crotch, making me blush. "But don't worry, I think I'll save that for the punishment if you don't pass the initiation."

"And what's the initiation?"

"Oh, just a little quiz. You're good at tests right?" Emma asked. I caught the mischievous glint in her eye, and knew she was tempting me, only to trick and embarrass me. Then have me masturbate in front of her for losing. Little did she know, I had some secret knowledge, but would it be enough? She sensed my hesitation. "If you pass, I'll give you a taste of what Level 2 will hold. I'll let you either touch my boobs or get a kiss."

"Okay, I'll do it. I want to level up," I replied.

"I thought you might say that." Emma smiled. "Okay, five questions. You have to get every one right. Ready?"

I nodded. The first four questions were relatively easy, meant to give me a false sense of hope before she asked the last question.

"What tattoo do I have on my back?" Emma asked with a smirk.

None of the pictures she sent me revealed a tattoo. But then I recalled a photo I saw of her at a beach that showed a small butterfly tattoo on her lower back.

"A butterfly?" I asked.

She quickly hid her surprise, then took a step closer studying my face intently. "How did you know? Was that a lucky guess?"

Emma would know if I lied. "I've looked at lots of pictures of you," I replied truthfully. "I've also seen lots of your pictures on social media."

Emma considered this for a moment. She knew she never sent me a photo revealing the answer, but couldn't be sure about her social media pics. At last she stepped back and smiled. "I don't know whether to be impressed or creeped out," she joked.

"Hey, all your social media pics are public," I defended myself.

"Yeah, yeah," Emma said. "Okay, you are now on Level 2. Choose your reward: you can either touch my boobs for 10 seconds, or get a kiss on the lips for 5 seconds."