Reroll

I wasn’t sure what to think about my current circumstances. On one hand, I was spending more time with Emma. More than I hoped to. It came at a price.

I felt like a contestant on a makeover show. Our first stop was my house. Dragging me down to my room, I was subjected to a snap wardrobe inspection. It didn’t go well. Her words were something along the lines of, “Do you have anything other than graphic tees?” That was insulting. Of course I had things other than an assortment of superhero and pulp culture t-shirts. The issue came from learning I had a growth spurt somewhere between the last time I wore them and now.

That was when Emma dragged me to a nearby clothing store. Reduced to nothing more than an oversized Ken doll, I paraded myself before her in various outfits she picked out for me. It was surprising how seriously she was taking things. The harsh words were never directed towards me as she went over me with a judging eye.

“Mm. That color doesn’t go well with you.”

“It’s a bit too loose.”

“Ah… If only they had that in grey…”

“There we go! Perfect!”

And of course, the ever descriptive and confidence-boosting: “Uh. No.”

But the situation was what you made it. Sneaking in some picks of my own while she was off collecting things made the experience worth it. Apparently, I was crap at style and the resulting laughter I got from her was worth it when I came out in something ridiculous or clearly not my size acting like I was a fashion model.

I paid for it all with the credit card my parents gave me. It wasn’t a huge amount considering the financial situation my family was in, but my parents stressed the importance of respecting money—especially when it came from others. Knowing my mom, when she found I’d spent it expanding my wardrobe, she would chastise me for only spending what I did. If she had her way, every t-shirt I had would be incinerated and I’d dress like a mannequin doll.

The next destination surprised me. I gave her a wary look as she **** me inside.

I suppose my hair had gotten a little long, but it wasn’t that bad. Emma didn’t let me say anything, instead, she told the woman exactly what to do. The next thirty minutes were a blur of blades, scissors, and brushes. The reveal at the end had me anxious. It wasn’t the sort of cut I’d get. I basically just had them shorten it when it got long. This was style, not function. It wasn’t bad and I kinda liked it. Emma certainly did. It was a change from what I was used to though, so there was some need to grow into it.

Back at my house, the assembly was complete. Emma picked out what I should wear and left me to change. Again, not the sort of clothing I was used to. Most of the stuff I wore was loose and, after she had pointed out earlier, ill-fitted. The completed look was utterly shocking. I didn’t recognize myself in the mirror. It wasn’t the styled hair or the new clothes. There was no doubt they helped, but it was what they brought out. Maybe it had been a long time since I last took a moment to look at myself. Gone was the slouched shoulders and almost timid look of the boy I’d once seen standing there. Instead, I saw a man. Sure, I wasn’t going to enter into any bodybuilding or beauty contests, but god damn. It wasn’t about how good it all made me look, it was about how it made me feel.

Gazing at the man in the mirror, I felt good.

Damn good.

Opening my door, I found Emma lounging on the couch typing away at her phone. She glanced over and all at once, I had her full attention. Rising from the couch, she gracefully strolled over as her eyes ran over me.

“Damn, Isaac. You clean up well.”

My face heated. “Really?”

She smirked. “You know exactly what I’m talking about. It’s written all over you.”

I rubbed the back of my neck. “Yeah… It’s a bit weird since it doesn't feel like me, but I like it.”

“Of course you do. I picked it out,” she said, lifting her chin slightly. She was proud of herself and deserved every bit of that feeling.

“Thanks.” The word seemed insignificant for the weight this moment demanded. I’d admit that my beginning relationship with Emma hadn’t been the best. Toxic and abusive came to mind. A lot of that was my fault. Letting her walk all over me was in large part because I wasn’t sure who I was and was content to drift down the waters of life. Today though? It wasn’t just the look. I was different.

Yeah, we still had our weird and twisted relationship to work out, but I had an idea what I wanted now. I was glad my somewhat—okay, massive—obsession with her had kept me under her thumb. What was the saying? Hardship is the mother of invention? Something like that. Without her, I would have never found myself. Her antics now weren’t so one-sided. All the crazy shit she did now? I wanted that.

Emma had changed too. It was times like this that I could see it. I don’t think the Emma I’d met months ago would care to do this. She was pushy as always, but there was a shift to it. I couldn’t put it quite to words, but when it came to me it was almost like she was more mindful of my state of being. She still teased me and I knew that would never change, but some of the meanness there was gone. The desire to torment me was absolutely there, but… I don’t know. It felt like it was something we did together rather than something she did to me.

Of course, it was probably because she was holding back. Last time she had dug in deep enough to draw blood and we never attempted anything since. I still hadn’t had to use our safeword, but something told me I probably wouldn’t need it. Emma always had a sense of me, knowing exactly where to push but never how hard to push. Maybe it was all in my head, but I believed she was now being considerate of that too.

Her expression shifted, giving me a suspicious look. “What?”

“Huh?”

She stepped back. “You’re looking at me funny.”

“Funny?”

“Yeah.” A teasing smirk formed. “You sneak a peek at your stash? Rub one out before changing?”

I scoffed. “I was only in there a few minutes.”

“And? That seems a minute and a half more than you need.”

“Hardly.” She had a convincing look of disbelief. I jerked my thumb back over my shoulder to my room. “Want to go find out? Five-minute guarantee or your money back.”

Her eyes held mine. “Okay.”

All at once, the wind left my sails. “W-what?”

Her smile widened. “I said, ‘Okay.’” To prove her point, she strode past me. My head turned as my eyes followed her. She paused at the doorway, looking back at me. “Coming?”

Was… was this happening? Holy shit. I didn’t know what awaited me, but I sure as hell wanted to find out.

Shit. I should have had a makeover months ago.

I rushed after her. She stood in the middle of my room. It was cluttered from the clothes she had strewn about when searching for something to wear, but she couldn’t blame me for that.

Slowly, she turned to face me. I was still several steps away. Standing here, I felt fear creep up inside me. A lot about me had changed, but not this. In the face of… whatever was about to happen… I was still the insecure boy. That was a lot easier to accept. It was my first time. I was allowed to be anxious about it, especially since Emma was far more experienced than I was.

Emma simply stood there, not saying anything. She was watching me, but it wasn’t the teasing minx that would normally accompany a moment like this. There was genuine curiosity there like she wanted to see what I was going to do. My legs felt like jelly and I had a hard time moving. I **** myself to. No way was I going to back down from this. If she was serious about this…

I stopped in front of her. She had tilted her head back slightly to look up at me. The silence only seemed to make my heart race faster. She was so close. Every breath took in more of her sweet fragrance. All I needed to do was reach out and touch her.

A quivering hand stopped just short of that. Pulling my attention from her eyes, I stared at the hand. So close, yet not quite there. “This is real… right?” I could barely hear my own voice.

“Real?”

“You aren’t messing with me, are you?”

“Why don’t you find out?” she breathed.

My hand pressed against her arm. She said nothing. The hand slowly moved up her arm. My gaze rose from where my hand touched to look in her eyes. Professional curiosity. That’s what she reminded me of. A step and I felt her body press against mine. I leaned forward. My arm wrapped around her waist as my lips pressed against hers.

This was nothing like the kiss we shared before. That had been something of raw passion. This was a timid curiosity.

Breaking the kiss, I looked into her eyes. She was still staring at me. Damn her and her poker face.

I kissed her again, this time with more intensity. She returned it in equal measure.

Holy shit.

This was happening. This was actually happening!

It was then that I realized I had no condoms. I mean, why the fuck would I?

Fuck.

I’d cross that bridge when I came to it.

Emma, long out of reach, was an open book in my lap. I had full access to… everything. One hand ran over her ass. An old memory, one of Ryan giving it a squeeze, flashed before me. I did the same, enjoying the sensation. The other pulled her closer, the feeling of her breasts against my chest driving me forward. Yet it was her hot breath against my lips that had my full attention. I hungrily attacked them. Months of denial were spilling over. She weathered it all, accepting everything.

My heart was thunder. My veins magma. Everything came at a rush, yet seemed impossibly slow all at once. I was vaguely aware of unbuttoning her shirt. Hands ran over her hot skin. The cotton fabric of her bra teased my fingers as they traced her breasts.

We separated and the suddenness brought me out of the mental fog that surrounded me only to find out it was because Emma had sat back on my bed. She said nothing, still fixing me with that unchanging look. But it was so much more now as I stood over her. For the first time since this whole thing started, I was finally the one dictating the shots. It was clear by the look on her face. She would accept anything and everything.

I took a shaky breath as I struggled to control myself. God, the look of her. That sweet expression she was making as she looked up at me expectantly. It was combined with her open blouse and the white bra underneath. She looked so… ****.

It was the hottest thing I’d ever seen.

As if picking up on my thoughts, she spread her legs. Everything was covered by her skirt, but the meaning was clear.

An open invitation.

I joined her on the bed. She went back as I pressed my lips against hers. She always matched my intensity. Never demanding more or offering less. As I kissed her, my hand slid up her skirt. Fingers brushed against the fabric there. I slid it aside—

“Isaac.”

The single word hit me like a colliding train.

“No,” I choked. Tears burned in my eyes as I gasped for breath. “Please, don’t.” I was begging. Pleading. “You can’t stop me now. Not like this. Not now. Please.”

Her voice was barely a breath. “I’m not.”

I worked up the courage to look her in the eye. Her expression hadn’t changed, but I noticed a coldness there. Or had it always been there?

“Do you want me?”

“Yes.” The emotion in my voice nearly choked out any understanding of the word. “More than anything.”

“I won’t stop you.” She shifted beneath me and the tips of my fingers brushed something wet and warm.

Something wasn’t right.

“Really?” She nodded, eyes staring into mine. Things still weren’t right. Was I just being paranoid? It was Emma, so no. No such thing as paranoia when it came to her. Yet she was making no effort to stop anything and was saying it was okay to continue.

To test things, I worked a finger into her warmth. She didn’t react, eyes still watching me.

I carefully withdrew my finger, getting zero satisfaction from what I had just done. The milestone I passed all but hollow. That all but confirmed it to me.

“What are you playing at?”

“Nothing.”

“It’s never ‘nothing’ with you. What’s the game? The angle?” The back of my neck was heating up and I felt like the person in the horror movie when the music cut out. “There a quest or something?”

She shook her head.

“Emma…”

“I know I haven’t been the best person and have done some pretty terrible things for my own amusement at your expense. You deserve this, Isaac.”

It was right here. Everything I wanted was right here. I was literally between her legs and she was half-dressed. I had my finger in her pussy for Christ’s sake. She was telling me to go for it. To finally experience what I had been denied and teased with for so long. Agonized over.

I wanted to sob. She was right there. I just needed some fucking confidence to take what I wanted. She said it herself. I deserved this.

So why?

Why was I fucking hesitating at the last step to the summit? Had I not suffered enough crawling up this high?

This is what I wanted.

Wasn’t it?

She sensed the shift as my thoughts and emotions warred within. Of course she did. Emma always read me like a book no matter how much I tried to hide from her.

“I won’t offer this again.” My eyes found her. I felt sick. What was wrong with me?

I looked away. “I don’t have a condom.” What a pathetic excuse, even to me. Was I seriously running away? Now?

“I have one.”

Of course she did. I still didn’t look at her.

“This isn’t a one-time thing. You can have me as often as you want—provided I’m in the mood too.”

I was looking into her eyes again. She was being sincere. My eyes went down to her exposed bra. How many times had I seen those glorious things? How many times had I masturbated wishing I could run my hands over them? How many times did I cum imagining those cute lips were around my cock? This was my chance to make all those fantasies a reality. If I stopped being a fucking pathetic coward for one second—

But I wasn’t a coward. Not like I was before. If there was one thing I had learned since meeting Emma, it was that I needed to start having a little faith in myself. If something felt off like this, maybe something was wrong. I did my best to detach myself from the emotions and observe the situation with an objective eye. It didn’t take long for me to start drifting to an answer.

Maybe I didn’t want this.

And if I didn’t want this… What did I want?

I let out a long, calming breath. It helped. “What about us?” I asked, voice not completely steady but enough that I wasn’t embarrassed by it.

“What about us?”

“You know what I’m asking.”

She didn’t say anything as she stared at me. “There is no us.”

“And if I want there to be?”

“I don’t have an answer to that.”

“I know you, Emma. This is another one of your schemes. What are you playing at?”

She shook her head. “Not a scheme. A choice.”

I actually chucked. Even with the oppressive atmosphere between us, I felt myself relax as I felt myself in a familiar situation. One that was strangely comforting. Emma was playing with me again. Should have known.

But her expression wasn’t in the playful form she had when she was toying with me. It made me pay attention. Whatever this was, she was being serious.

“Choice?”

She nodded. “Continue as we were. You can finally get a taste of the real thing.” Serious as the situation was, Emma was still Emma. There was a small tease to her voice and the corners of her mouth twitched upward. “I was serious earlier too. Take me now, you can have me whenever you want.”

“Sounds like an easy choice to make.” She nodded. I let some of the tension out with a breath. “So what’s behind door number two?” With what door one was offering, it was going to be a hard one to beat.

“Nothing.”

I frowned. “Nothing?” She nodded. “The hell. The choice is there is ****?”

She shrugged. “If that is what you think. Sounds like your decision is made.”

“I don’t think so. Nothing is ever that simple or clear with you. What? What’s the trick?”

“It’s exactly as I said. Option one, you can fuck me to your heart's desire. Every day? Twice a day? Three?” She paused. “Well, within limits of course. If I’m not available, I’m sure one of my friends will be happy to help out. Option two, we stop here, you get off me, and I put myself together.”

Pulling away from her, I thought things over. There had to be an angle to this. Emma might know me, but I was also getting a feel for her as well. The hint was how mind-boggling stupid the disparity between choices was. She wasn’t like that. Making me admit or choose something difficult was what she enjoyed. If she was playing softball with me because of our last conversation, she never would have put sex with her as a reward.

Another factor was her lack of enjoyment. She seemed… sad? Resigned maybe. Something in me suspected this was big. So big, she was tossing it to me to decide.

“If I pick option two—”

“If you pick option two, I promise that you will never fuck me.”

I blanched at her tone. “Ever?”

“Ever.”

I was so confused. What was the angle here? She was offering me two choices, but the words were meaningless. What were the real choices being offered?

My eyes widened.

“Looks like you figured it out.” I expected a playful smile, but it wasn’t there.

“The first option is fuck buddies. You said it yourself; I can fuck you anytime I want. The second, you promised me that I would never fuck you. You could have easily said I’d never have sex with you, but that wasn’t what you meant.” She didn’t say anything, only giving me her passive stare. “What I don’t get is what option two offers.”

“I already said what it was. Nothing.”

“It can’t be nothing.”

“It is nothing because that is what I promise. Nothing.” Emotion crept into her face. A softness. Maybe guilt. “I know what you want from me, Isaac. I… I don’t know that I can give you that. So I offer nothing.”

I shook my head. “You aren’t offering nothing. You are offering a chance for something.” I pulled away. Standing up from the bed, I straightened my shirt.

“Are you sure? I told you I won’t offer this again. Chances are high you’ll get nothing.”

I offered her my hand. “I know what I want. Even if I end up with nothing, I would rather give it my all chasing what I want rather than settling for something I don’t.”

“You really have changed,” she said as she took my hand. I easily pulled her up from the bed. That familiar smirk was waiting for me. “There is hope for you yet. You’re still an idiot. But there is hope.”

I grinned. “Does that mean you’re falling for me yet?”

“Not in the slightest,” she said, laughing as she began buttoning her blouse. Ah. I already missed the sight. She was right. I was an idiot. I could have been balls deep inside her right now. “Come on,” she said with a look that suggested she knew what I was thinking.

“Man, your friends aren’t going to recognize me with the new clothes and hair. You going to try to pass me off as someone new?” It sounded lame, but I needed something to get my mind off what I had turned down.

“Huh?”

“Wasn’t the point of all this to make me presentable to your friends?”

“What? Why? They already know you’re a helpless nerd. Putting makeup on a pig isn’t going to hide it’s a pig.” I frowned as an all-too-familiar smile formed. Did she just imply I was a pig? “Those,” she said with a finger gesturing up and down. “Are so you’re presentable to my family.”

It was like she kicked a chair out from under me and I was dangling over a sheer cliff.

“Wait. What?”