Let's Play a Game

I was a haunted man. I tried to distract myself with video games, a book I’d been working through, and planning for the next DnD session. Nothing worked. I was practically a mute at dinner, and no matter how much my parents prodded, the most they got out of me were a few words. My phone became my warden. No matter what I did, it was there, taunting me with its silence.

As the evening dragged on, the more antsy I became. It got to the point where I was pacing in my room. This wasn’t like me. There was no reason why a stupid photo of Emma should cause me so much grief. A quick Google search and I’d have more provocative pictures than I could ever hope to look at. I shouldn’t even be accepting them in the first place. We were… friends? Study-buddies? Whatever we were, it was not something where this was anywhere near appropriate.

My phone chimed and all thoughts fell away as I rushed to it. Unlocking it, I found a message waiting for me. My hands were shaking as I realized it was from Emma.

>Hey

I stared at the single word, forcing myself to take deep, calming breaths.

They didn’t help.

My fingers were about to start typing when I **** myself to stop. I was too eager. She would know that if I immediately sent back a response. I purposefully waited a minute, even though I only lasted half of it before sending my reply.

>Hey

Ugh. I’d even given myself some time to think and that was all I could come up with?

>I promised you a picture

My heart raced as I waited. My mind had gone wild wondering what she’d send me this time. Her last picture was daring and exciting. Even if it was the same setup with another pose, I was sure it would be epic. The picture popped up a few moments later. I was shocked because it was… her. Of course it was. What surprised me was how normal it was. She was dressed in the same jeans and long-sleeved top she’d worn to school today. Sitting cross-legged on the bed, she smiled brightly at whoever took the picture as her hands rested in her lap. It proved that Emma was crazy photogenic. No matter what she was doing in the photo, or what she was wearing, she was gorgeous.

Realizing I’d been staring at the photo for a solid minute, I quickly typed out a response. Even if I was mildly disappointed with the result, it was still a great photo.

>Wow

>Wish I could see your reaction. Disappointed?

>Not at all. It’s a great photo

>Suuuuure

>Really. Thank you

>Want some more?

As if she needed to ask. I was still a bit high off this whole situation. One of the hottest girls in school was texting me and sending me pics of herself. The reason why didn’t matter, only that this was a golden opportunity that I wasn’t going to let go to waste.

>Of course

A smile emoji was at the front of her sentence.

>I figured you would. Can’t give them for free though

That deflated the sails a bit. It was no secret my family was well off. By extension, that meant I had access to money. Was this her goal all along? Get close, then work to get money out of me? Dad always warned that there were people out there that would try to take advantage of personal relationships. Gold diggers and fake friends who only cared as far as the money lasted. Emma never seemed like someone who was in it for the money, but I suppose that was the point. Were people ever that obvious when they were after your money?

Now I was faced with a bit of a moral dilemma. I wanted those pictures, and I had money. It seemed wrong to buy them though—not that wanting them in the first place was any better. Maybe I could blame it on teenage hormones.

Biting my lower lip, I typed out my reply.

>How much?

>lol Not like that. I mean a game. Bored right now and could use a distraction

Relief flooded me. Even though I didn’t know why she was contacting me, it made me feel better knowing she wasn’t trying to pump me for money. It already made me feel guilty that I’d offered money in the first place.

>What game?

>It’s simple. I ask you a question and you try to answer it

Rubbing my chin, I stared at the phone. As simple as it sounded, it was anything but. We may have met a fair amount of times these past few weeks, but I didn’t know much about her. Conversations outside of study material were rather limited. At least there wasn’t a downside that I could see. I might get lucky and answer a few right.

>Okay, I’m in

>Great! First question: What is my worst subject?

I grinned, speedily running my fingers over the screen. This was an easy one.

>Math

A few moments later, I was rewarded with an image popping up in the messenger. It was more or less the same one as I had before, only she was leaning back on the bed. A few seconds of staring was all it took for me to notice the other big change. Her top was halfway unbuttoned, showing an ample amount of skin as she smiled at the camera. Excitement rushed through me as I hoped the trend would continue.

>Congrats on your first win. Wonder how far you can get…

>Second question: What does my dad do?

The grin fell off my face as I stared at the question. Scratching at my head, I combed my mind for an answer. I knew she said something about it in passing once. Something to do with the law. Lawyer? No, that wasn’t right. I was on the right track though. Something in law enforcement. A cop? That seemed a little closer to the answer, but I wasn’t too confident on what specifically he was. Second question in and I was already struggling. Time to test how specific I had to be.

>Law enforcement

>No credit for partial answers.

There was a smile emoji with it.

>What specific job does he do?

Well, it was a valiant attempt. Now it was time to take a shot in the dark.

>Detective?

>Final answer?

>Yeah.

The wait was agonizing. Was she sending me another picture or letting me sweat before telling me I was wrong? Another picture flashed on my phone. Sitting on the edge of the bed, she was leaning forward slightly, hands on her knees. There was an impish grin on her face as her top hung completely open to reveal the white bra and skin underneath. My eyes ate up the image, my heart beating faster. I had a picture of her with nothing but her underwear on yet this seemed a hundred times more exciting. I was watching a live strip show at one frame a minute. Well, ‘live’ was debatable since I was pretty sure she had taken these photos in advance. There were only two questions I had now. How many did she take, and how far did they go?

>Impressed you got that one. I only mentioned it once

>Going to be honest, that was more of a guess

>Hopefully your luck continues.
>Third question: Who is my best friend?

Well, fuck. I had no idea. Not even a guess. I couldn’t name all the people she sat with at lunch let alone specific people she hung out with. I couldn’t even ballpark a name. The topic of friends, even if in passing, never came up.

>Sorry. I don’t know

That got a sad face emoji after a brief wait.

>Fourth question: Who am I dating right now?

Emma was dating someone? Shit. Once more, I had no idea. This was only highlighting how little I knew about her. Actually, considering the context of us hanging out, me knowing all this would be creepy as hell. We only studied together. Suddenly being able to name drop people close to her would elevate me to stalker-level.

I was finishing up my text saying I didn’t know when I stopped, deleting what I had typed out. This was a test where leaving the answer blank counted as much as giving the wrong answer. Even though I didn’t know specific names, I realized one answer didn’t need one.

>No one.

I doubted that was the case considering how popular she was. Still, it was better to fill in a random answer than leave it blank. You never knew what might get you partial credit.

To my surprise, I was rewarded with another picture and I was so glad I followed my gut on that one. She was no longer looking at the camera, but towards the side. Her smile was gone, replaced by a more serious expression. Lips parted slightly, she looked down towards her now bare shoulder. Her top had slipped down her back, arms still covered with her sleeves.

God damn, she was stunning.

I was still in the middle of ogling her picture when her next text came in.

>Fifth question: Am I a virgin?

Rubbing my jaw, I stared down at the phone. This was the equivalent of a true/false question and I should have been thankful for that fifty-fifty shot. At the same time, concern gnawed at me. This was a rather… personal… question. I also had a good idea what the answer was, but I was hesitant. She’d had some nasty rumors follow her around since sophomore year that she was a slut. Not sure I believed them based on what I knew of her, but I doubted a girl as popular as her…

Well, I wasn’t going to make rash judgments based on that.

The seconds stretched as I focused on the question. I knew waiting was only going to make it more awkward. It was a yes or no question and I was treating it like a thesis statement. I already knew which answer was statistically more probable. The question now was how badly did I want another picture?

>No

Rubbing the back of my neck, I waited. As I expected, another picture arrived, though my excitement was a bittersweet one as it confirmed my suspicion. Of course a popular girl like her had sex before. I knew I had no right to be jealous but I couldn’t help it. Not with seeing pictures like this. God, whoever that bastard was, he was the luckiest bastard in all of human history.

Fuck him.

With a sigh, I focused on the picture to clear the foul thoughts from my mind. Her top was nowhere to be found as she smiled sweetly at the camera with only her bra in view. I had no idea how much luck I was burning right now. I had to set the phone aside and take deep breaths to calm myself down. This seemed like a dream, but this was happening. No way in hell was I going to question that too deeply.

>Took you long enough

A winking face accompanied it.

>Sixth question: Since you now have a few pictures of me for reference, how big are my boobs?

Ugh. Another impossible question. How the hell was I supposed to know?

I was still trying to figure out my best way forward when I got another text.

>I’ll cut you some slack. Just cup size is fine

That brought it down in the realm of possibility but I could stare at them all day and still be no closer to having an answer. In this case, I had to eliminate the ones I knew weren’t the answer. D cup wasn’t happening. Her breasts weren’t that big. She wasn’t flat either, so A cup was out. That left B or C cup. Since she leaned towards the smaller side, B cup was probably my best bet. My confidence wasn’t there though. Logically, it was the most likely answer, but I was nervous about answering the question in general. If she was actually a C cup, I’d be saying I thought her boobs were small.

I was really hating these deeply personal questions. As the questions got more personal, the more I found myself wondering why she was asking them. There were nearly an infinite number of other questions she could ask. Why did they have to be so intimate?

>B cup

A breath escaped me as I saw another picture appear. This was a lot closer than the others. I was treated to a close-up shot of her toned stomach as her hands worked to undo her jeans.

Between the increasingly provocative pictures and the questions, my erection was getting increasingly persistent in its need for attention.

A laughing face accompanied her next text.

>Good guess! As a bonus, I’ll send you another one if you answer a question about yourself
>Are you a boobs or ass man?

Nervously, I typed out my answer but hesitated when I went to send it. Was she flirting with me? This whole situation was so confusing. We’d gone from studying together to her sending me borderline nudes in less than a month. None of this was normal. That little voice of hope was constantly whispering things I wanted to hear. Did this mean she liked me? It didn’t seem possible that someone like her would have an interest in me, but there were plenty of guys in the world who lucked out and dated women out of their league.

Or maybe she was just a flirty girl. She was clearly more comfortable with more intimate things than I was. This whole damn thing was one frustrating enigma. As I glanced back up at the latest picture, I had to admit that it had its perks.

>Boobs I guess. But really, I think a girls smiling face beats both

>Haha bullshit.

Frowning, I sent my reply.

>Truth

>Oh, then I suppose you want to stop here?

>The next few pictures don’t have my face in them
>The ones after don’t have clothes...

There was a moment where I think my heart stopped for a moment as I read that last text. It took me a second, but I think I managed to come up with a decently witty response.

>Maybe you better send them anyway so I can confirm

>lol Not happening. You want them, you earn them.
>Which brings us to the seventh question: Do I spit or swallow?

>What the heck?

>You have a 50/50 chance. More than fair

>I mean what is with these questions?

>?

>Aren’t these a bit personal?

Her response took a bit longer than normal.

>If you have a problem with the questions, you can stop at any time. Considering the nature of the pictures you are getting, I think the questions are theme appropriate, don’t you think?

>Yeah but aren’t you embarrassed by me knowing these things?

>Why would I be?

>We study together

>You’re pretty weird, Isaac, you know that? You’re more than happy to get pictures of me undressing, but knowing something like if I’m a virgin or not crosses a line?

Taking a deep breath, I typed out my response and tried to double-check that she wouldn’t be able to mistake the tone. Gathering my courage, I sent it.

>I’m just confused about what is happening right now.

It took a long time for her to respond. For a moment, I was worried I ruined it. When she finally got back to me, that fear didn’t go away.

>You really know how to suck the fun out of this. Fine. Answer that question and I’ll send you all the pictures I took

Fifty-fifty. The same chance as a true or false. This one really was a toss-up though. Unlike the question about her virginity, I had no idea how to weigh this. Cum tasted bad, right? I didn’t know. It seemed like something that would. If that was the case, the safer option would be spit.

More importantly, I wondered if I should apologize first but quickly nixed that idea. Maybe it was because everything was in text form and that I was just making it sound worse than it was.

No, I should just answer the question and see what happened.

>Spit

There was a long wait. A really long wait. Several minutes passed and I began to pace around the room. Did I get it right? Was it taking so long because there were multiple pictures incoming? The thought that I was actually going to see a picture of Emma naked… God, it was so wrong, but that didn’t stop my desire to see it.

My phone chimed loudly, causing me to jump. Racing over to the phone, I quickly read the text with a slowly expanding sense of dread.

>Mmm. Too bad.
>See you Wednesday, Isaac.

Staring down at the phone, I read the messages several more times before letting the phone drop to the bed.

Fuck.