Emma 2.0 (Alternate branch)

I awoke Saturday morning to a knock on my bedroom door.

Fuck! My head felt like someone had driven a railroad spike into it, right between my eyes.

My parents were out of town for the weekend, attending a friend’s son’s wedding. I had, more carefully this time, raided the **** cabinet again on Friday night. I’d taken small shots out of a variety of different bottles of hard liquor, trying to get as drunk as possible as quickly as possible. The thought of what was happening with Emma’s friend group (and Mike) that Friday night was a little too much for me to face while sober.

So I awoke with a rather stunning hangover. Each knock on the door seemed to drive the railroad spike even further into my head.

At first I thought it was my mom, having somehow forgotten that she wasn’t even at home.

I looked at the clock on the nightstand next to my bed. It was almost 11:00 am.

“Who is it?” I asked, finally remembering that it couldn’t be my mom.

I watched the door swing open and then the very last person I would have ever expected to see stepped into my room.

It was Emma!

She had clearly been out running, dressed in tight, spandex biker shorts, a sports bra that made her breasts look even more perfect than I knew they were, and running shoes, with her AirPods in her ears and her phone strapped onto her left arm with an armband.

She was covered with a visible layer of sweat. It was about 5 miles from our house to hers. Even if she had run directly from her house to mine, it was still a considerable run, which would explain her sheen of perspiration.

God! She looked so fucking incredible!

She slipped her AirPods out of her ears and tucked them into the front of her spandex shorts. Lucky damn headphones! I thought.

I wanted to be pissed at her, but I found there was no way I really could. I was thrilled to see her once again in my bedroom, and even more thrilled to see her displaying that unbelievably hot body of hers.

“Good morning, Isaac,” she said softly to me as she pulled my computer chair over by the side of the bed and sat down in it. Normally I’d be mad at someone who was all sweaty sitting down in my office chair, but since it was her nearly naked body, I didn’t really give a damn.

“Morning,” I said back to her, the pain of my hangover mostly forgotten at the joy of seeing her again.

“I’ve missed you,” she said, once again very softly, a look of melancholy on her face.

I almost spurted out that that was her own fault, but caught my tongue. I wasn’t going to be the one to put her on the defensive. I knew that her response to what I’d done was pretty well justified.

“I really missed you too,” I replied simply.

“I thought I’d never want to see you again,” she said to me. “But now the thought of not seeing you practically crushes me.”

There it was again. My old nemesis. Hope. God it could be such a cruel mistress!

“That thought has been crushing me every single day this week,” I said.

“You want to see me again?” She asked, looking genuinely surprised by that.

“Of course. I can’t think of anything I would want more than that.”

“But …” she started and stopped. “I thought you’d hate me by now.”

“I would never hate you, Emma,” I said. “Everything you said to me last Friday night was 100% justified. I was an asshole. I could only think of what I wanted, and didn’t even stop to consider the implications of what you were saying to me. I never should have done what I did to you. I cannot blame you for your response to it.”

“I want us to be together again,” she said to me. I could actually see her eyes welling up with tears.

Hope began running victory laps around inside my brain. The deep dark part inside of me kept screaming at me, telling me I was only setting myself up for even more pain, but I had no desire to listen to it.

“Me too,” I said. “More than anything.”

“Are you sure?” She asked. “It isn’t going to be easy.”

I wasn’t at all sure what she meant by that, but I also wasn’t sure I cared.

“Of course I’m sure,” I said.

“You have to know,” she said, “that I am really not sure if I can ever trust you again, Isaac. You carefully cultivated that trust in me, and when I finally accepted it and offered it back to you, you tore it out of me and stomped on it. It’s going to be really hard for me to recover from that.”

“So then why are you here?” I asked.

“Because I want to try,” she replied simply. “I can’t promise that I can ever get back to where we were last Friday, but I’d like to try, if you’re willing to put your trust in me.”

“Of course I am willing,” I said.

“You need to understand what it’s going to mean to be willing to do that before you agree to it.” She said to me.

Uh oh. That darker voice was making itself known again. I could feel Hope starting to slow his dance inside of me down a little bit, paying ever more attention to the voice of doubt within me

“What do you mean?”

“If we’re going to do this,” she said, “we’re going to do this on my terms.”

“We’ve always been doing this on your terms,” I said to her.

“Not really,” she said. “You’ve only sort of let me be in control. You still had a hand on the brake lever the whole time, tempering my own desires when they brought you too close to the flame. I won’t give you access to the brake lever this time, Isaac. I want you to come face to face with my darkest desires and prove to me that you can handle them, that they won’t send you running away screaming. If there is to be any hope for me to ever give you the trust I’ll need to once again offer to you what you are looking for, it will only be because you’ve shown me that you’re willing to trust me completely, even when I push you way beyond what you think your limits are.”

God that sounded scary. She had already pushed me into places I never wanted to go. She was telling me it was nothing compared to where she really wanted to take me. Could I survive that?

I was not at all sure I could.

But there were two quick follow on questions that immediately came to mind.

Could I survive never seeing her again? Would I forever regret it if I didn’t try?

Those were much easier answers for me.

“Okay,” I said, simply and quietly.

“I want you to be very aware what you are accepting here, Isaac. I want us to start dating again. We will be, as far as anyone else can see, a couple again. But for now, it will be purely platonic between us. I might cuddle with you, and hold your hand, and maybe even give you kisses in public. But in private, we will be friends and nothing more. At least for a while.”

“I can live with that,” I said. “It’s always been our friendship that I value the most anyway.”

“Of course, that won’t be the extent of our relationship. I’m going to push you, Isaac. Hard. Way beyond what you think your limits are. You will only have two options when I start pushing. You will either accept what I am doing, or you will walk away. When you walk away, you will be walking away forever. There will be no safe word this time. You can let me know that I am hurting you, but it will do you know good to ask me to stop. I won’t stop. I will push and you will take it or we will be finished. For good.”

I swallowed hard.

This was really frightening. I couldn’t even begin to imagine the places she might be willing to go if I agreed to accept anything she might throw at me. I’d gotten small glimpses of how devious her mind could be. What would she be like if I agreed to not put limits on her? It was an incredibly scary proposition. I could see the red hot stove, just outside my reach, and I found myself struggling to get close enough to press my hand down onto it. I just had to see how much it would burn me

“I accept your terms,” I said nervously.

“I knew you would say that,” she said. “But I’m not convinced you really mean it. So, of course, I have a new quest for you. We’ll be officially dating again the moment you accept my quest and successfully complete it.”

“I am ready,” I said, confidently.

“You think you are ready,” she said with a wicked little grin. “Let’s see if you really are.”

I swallowed hard again.

“Get out of bed,” she said to me.

I climbed out of bed and stood before her. My boxer briefs were tenting considerably with the erection that was straining within them.

"Happy to see me?" She asked with a smirk.

"God yes," I replied.

"I might be able to change that." She said ominously. "Take off the underwear," she ordered.

I quickly pulled them down to the floor and stepped out of them. All of my (nearly) 5" cock sprung into view, slapping up against my bare belly.

"If you just woke up, you probably need to pee?"

I nodded.

"Then go do that," she said.

I made a beeline towards the bathroom. When I got back to my room, Emma had the computer on, the office chair in front of the computer desk. She was standing beside the desk with her hand on the mouse.

"Sit," she said to me.

I took my place in the chair and noticed she had the folder open on the drive where she had been uploading all her content for me. There was only one video file in the otherwise empty directory.

"Do you have some lube you like to use?" She asked. I directed her to where I kept a tube of KY. She came back with it and handed it to me.

"You'll be wanting this," she said to me before moving the mouse and double clicking on the video file she had uploaded. "I made this for you last night. I'll consider your quest completed only when you make yourself cum while watching it. No time limit this time. You can go as quickly as you want, or watch it as many times as you need, but you have to make yourself cum while you watch it. Understood?"

I nodded. She hit the play button.

The video started with a POV shot looking down on a kneeling, and very naked Emma as she looked up, smiling at the camera. In front of her face was a massive cock which I immediately recognized as Grant's. She had her tongue out and was erotically licking all around the head of that monster.

"You like this cock, don't you slut?" Grant said to her.

"No," she said. Then after a pause she added, "I love this cock."

"You do know why your boyfriend didn't want to have sex with you, right?" He asked her.

"No," she answered him, "tell me."

"Because he knew he could never fuck you the way that I fuck you with this cock."

"Mmmm, hmmm," she hummed as she had taken his head inside her mouth.

"He's smaller than me, isn't he?" Grant asked.

"He's a LOT smaller than you, babe," she said.

Oh God!

There was literally no doubt in my mind that she had set this up, specifically for me. The only time I had ever used her safe word before our breakup was when she had been comparing me to someone she had fucked. I told her how much I disliked that, and asked her to never compare me to anyone again. There is no way it was a coincidence that the first place she pushed me was right into the place I had already told her I never wanted to go.

Once again, I felt exactly what I had felt the last time she had gone there, when I had decided to use the safe word. I could feel all my desire drain from me, to the point that I could feel my erection flagging.

No! I thought dejectedly. Surely I wouldn't fail this soon! How could she immediately push me right into something that she knew really bothered me?

Of course, I already knew the answer to that question. She did it on purpose. She wanted to make me as uncomfortable as she could, as quickly as she could. She wanted to test me right away. I agreed to let her push me. She wanted to immediately see just how serious I was.

I closed my eyes and took a deep breath.

"Admit it slut," I heard his voice say to her. "You could never really enjoy his little pecker after having a real man's cock like this, now could you?"

I felt yet another twist of the knife at her reply.

"Of course not," she agreed.

In my heart of hearts, I guessed that she was playing along with him to stroke his ego, or that perhaps she had even setup the entire line of conversation as a means of pushing the biggest button inside of me that she knew how to push. But I certainly couldn't ever be 100% sure of that, now could I? It made me feel so weak and ineffective to hear them talking about me like that. It pressed deeply into my own insecurities. I knew that my own cock was on the small side of average. I always wondered if that would mean that I would never really be able to please a woman during intercourse. More specifically, it made me always wonder if Emma's experience with more handsome, powerful, and well endowed men would make her find my own performance less than satisfying.

I knew that fear was at least a little part of my desire to see and hear about her receiving pleasure from others. It was also likely part of the reason I pushed her into Kyle's arms the previous Friday. If I could put off the moment when she discovered my own inadequacies, perhaps I could keep our relationship going for even longer. That wasn't the whole of what motivated my desires, but it was a least a part of it. That was why I hated hearing the comparisons between me and her other lovers.

For the moment, I did my best to set those inadequacies aside. I opened my eyes and watched that massive cock slide in and out of her mouth. I could see the sheer pleasure in her eyes as she bobbed up and down on it. I realized that was what I really wanted to see in the first place. If having someone better looking, or stronger, or better endowed than me was a source of pleasure for her, then it was only giving me more of what I longed to see in the first place. I chose to focus on the signs of her own pleasure. I saw the look of pleasure on her face. I listened to the moans in her throat as she sucked on his cock. I looked past that union to her breasts and saw how incredibly turgid her nipples were. I could see her hand moving between her legs as she touched herself to increase her own pleasure. I chose to focus on her pleasure. It didn't make it so that I couldn't hear the way they were putting me down. It just made it more tolerable. My focus on her desire fed my own arousal faster than the comparisons could tear it down.

"You need me to fuck you, don't you, Emma?"

"Oh god yes. Fuck me with your big dick, Grant."

"Even though it will forever spoil you? Make you wish your little Isaac could have a cock like this?"

"Yes. I don't want any other cock, Grant. Give me your big fat cock."

"Tell me you're a slut for my big cock, Emma. Tell me how bad you want it."

"I don't just want your cock, Grant. I need it. Give it to me. Fuck me with your massive cock. Make me forget about my boyfriend forever."

The scene shifted to another POV. In this one it was clear that Grant was laying down on his back on the bed. Emma was straddling his waist, facing away from him, her absolutely gorgeous ass fully on display. I squirted some KY into my hand and began stroking myself to that sight, my erection having returned to it's fullness in spite of the things being said in the video. I could see Grant's massive organ poised below Emma's gorgeous ass. It was an incredible sight! I moaned as she reached down and grasped his condom-sheathed shaft and placed it at her opening. With one swift downward thrust, a few inches of his shaft disappeared inside of her.

"Oh fuck yes," she said. "God that feels so good. Your cock is so fucking perfect Grant."

"I know," he said with a chuckle. "You keep coming back for more of it, don't you slut?"

"Yes," she said. "I love it so much."

I noticed that on that initial thrust, Emma had added a timer in the lower right corner of the video. It was then that I noticed she had taken her phone out and had also started a timer, which was a little ahead of the timer in the video. I realized it was a timer she had started when I began stroking my cock. I watched as Grant's hand reached out and began stroking Emma's ass.

"God you are so fucking beautiful, Emma," he said. "This ass is absolute perfection. It's way better than a nerd like Isaac should ever deserve."

He grabbed one of her cheeks and moved it up and out to show a perfect view of her pussy stretched widely around his thick shaft. It looked so absolutely glorious. It was the best view of her being fucked that I had ever seen in any of her videos. It was that sight that really got me going. I loved watching her stretch around such an imposing organ. The video kept that POV for a little while as she slowly fed more and more of him inside of her, until she finally bottomed out.

"So fucking deep inside me," she said loudly, groaning in pleasure.

"I'm reaching places Isaac can only dream of," Grant replied.

"Yesssss," she hissed, "soooo ... gooood."

I heard a moan. It took me a little bit to realize it had come from my own mouth. Those words still hurt me, a lot, but I suddenly realized something. That pain, when coupled with the intense arousal I was experiencing at such a glorious sight while also stroking my cock, only served to increase my arousal. I'd experienced that phenomenon before, of course, because Emma had always managed to feed my arousal with a mixture of emotional pain. It was how I realized that I was like a masochist, deriving pleasure from the emotional pain she inflicted upon me. I had assumed that too much pain, such as what I had felt the time that I used the safe word, would always overwhelm the arousal and put out the fire. But the arousal I felt in that moment was way more intense than anything I could remember. Seeing something so intensely erotic, knowing that Emma had made it specifically for me, feeling the heat of her body behind me as I watched her getting railed in front of me was an incredible aphrodisiac. After the week I had, full of the worst lows of my entire life, the intensity of this particular high was nearly palpable.

She put her lips to my ear.

"Give yourself to me, Isaac," she whispered to me. "Let it all go. Focus on how much you love watching me get well and truly fucked."

There was another shift and another POV. It was similar to the one before, except that Emma was turned to face the still prostrate Grant. She was eagerly and aggressively bouncing up and down on his shaft. Her tits looked so incredible as they bounced up and down to her rhythm. Her eyes were screwed shut and she was biting her lower lip and moaning.

"Oh fuck," I groaned at the sight. I noticed the timer had jumped from around 3 minutes to over 8 minutes.

"Tell him," Grant said to her, leaving no doubt that this video had been deliberately staged for my benefit. "Tell Isaac how he will never be nearly as deep inside you as I am now. Tell him how he can never fuck you the way I fuck you."

"Oh god, it's true, Isaac," she said, looking into the camera. "He fills me so, so good. His cock is so deep inside me. Deeper than you will ever be."

Shit!

Once again it felt like a knife stabbing me in the chest, but I was way too far gone in the arousal of the moment for it to squelch my desire. Instead it fed it, like gas to a flame, an indescribable mixture of pleasure and pain. I lost all control as I heard her next words.

"You will never fuck me like this, Isaac," she said.

My hand began furiously pumping my own cock as I watched Emma grind herself down hard against Grant's pelvis. She threw her head back and wailed loudly as her body bucked hard against another man, a man I knew quite well, who was a part of my group of friends. She was clearly cumming on his cock while thinking of me, while telling me how I would never quite measure up to the pleasure she was feeling in that moment.

It was too much, way, way too much stimulation for my completely overwhelmed and addled mind. I felt myself pass the point of no return and felt myself pulsing in orgasm, perfectly timed to the very vocal orgasm coming from the lips of the onscreen Emma. I came more than I can ever remember cumming, likely because it had been many days since the last time I had come, but also because it was the most intense mixture of pleasure and pain I had ever experienced.

Emma reached over and stopped the timer on her phone, then handed me some tissues to allow me to clean myself up. I had reached over to stop the video, but she wouldn't let me. She made me sit there and continue to watch Grant railing her. They switched positions several times, each time advancing the timer in the lower right corner of the video. With my arousal sated, there was no pleasure to temper the pain of watching her get fucked, of listening as Grant made her confess to me how great his cock felt and how I would never measure up. In that moment I felt incredible guilt for having such twisted and perverted desires. I felt, mixed with that guilt, the full brunt of the pain of my own insecurities, brought to light by the godlike way that Grant was fucking her. I felt sick to my stomach, but I knew that I had to simply fight it down. I desperately wanted Emma back in my life. I wasn't going to allow her to scare me off on her first test of my resolve. So I fought back the nausea and fought back the tears and just watched her pleasure herself on one of my friends.

The video ended with Grant pulling out, ripping off the condom, and dumping his cum all over her belly and tits as she laid on her back on the bed. The video then faded to black, with the timer from the lower corner now filling the screen. It read 23:42. Almost 24 minutes of him fucking her, although I only got to see a heavily edited version of that that was about 8 minutes long in total. She picked up her phone and showed me that my timer said 4:18.

"He lasted 24 minutes inside of me, Isaac," she said to me. "You barely got over 4 with just your hand. Looks like you have a lot of work to do."

She let that sink in for a little while.

"Get dressed Isaac," she said to me eventually. "I need you to give me a ride home. I ran about 7 miles on my way over here. I don't want to add another 5 to it."

We rode to her house in silence.

"Are you doing anything tonight?" she asked me before getting out of the car.

"Mike is coming over to watch some anime on Netflix," I replied.

"Can I join you?" She asked.

"I would like that a lot," I said.

"Careful what you wish for," she said ominously before getting out of the car and trotting up the steps to her house.