Tails You Lose

After going home with James, Isaac had dinner with his parents before deciding to call an early night so he could study more in the morning, and so he could lay in bed and process the kiss that Emma gave him. His heart had never felt so large in chest, an expanding ball of molten iron trying to free itself and skipping beats every time he thought of the way she had pressed herself against him. It was that kiss, that sweet embrace, that rid him of all his anxieties. This wasn't some ploy to tear at his heart strings, to break him into a thousand pieces for her pleasure. It was none of that, it was a girlfriend giving affection to her boyfriend.

Lying in bed, he did not think he had ever felt so content in his entire life. Soon, he would finish his exams, be on summer break, and have a gorgeous girlfriend to boot. The Isaac from a year ago would never believe this new version of him existed.

Still, one thing bothered him, what had she meant when she said she would see him tonight? The question was quickly answered when his phone dinged with an ominous text from Emma.

Check the google docs.

Tentatively, he moved over to his desk, put on his headphones, and loaded up the latest video in his folder.

Emma was holding her phone in her left hand, she was wearing the same clothes she had worn in the library, and behind her was a white tiled wall with mirrors and sinks spaced two feet apart. She was in a restroom -- the library's restroom.

"Hey baby, I'm sorry that I'm going to take so long to get out of here, and that you're going to be waiting for me at the table for a little while, but don't worry I'll make it worth your time. I know you put in a lot of effort to make sure that I pass math, so just this once, I'm going to teach you something instead of the other way around." Her voice was like syrup seeping into his eardrums, so deliciously sweet.

Slowly, she unbuttoned her top, and allowed it to fall to the floor, revealing her pert breasts for his eyes to relish.

"First things first, I need you to take your cock out and stroke it for me. But make sure to do it slowly, I want you to last a little while."

Isaac desperately pulled at his pants, refusing to move his eyes from the screen and coordinate himself. After a moment, he clumsily released himself and began to gently stroke his cock as he stared intently at the screen.

Smiling, as if she could see his frantic attempt to follow her instructions, Emma dropped to her knees, her free breasts heaving slightly with the downward motion.

"Today baby, I'm going to give you a lesson about making a commitment. Earlier today I asked you to choose between two numbers. A simple task." Her voice had turned cold now, gone was the sugary syrup, now her tone had a frozen edge slick with bitterness.

Slowly, her hand reached out of frame, and pulled into sight an all-too familiar cock. Fucking Favorite.

Isaac's brain began to go haywire with the realisation that this was not going to go how he expected, that there was a reason she had taken so long in the bathroom and it was not one the logical side of him would like. Emma began stroking Favorite, her slim hand not even reaching halfway around the monstrous cock's circumference. With an excited smile, she spat a fat glob onto the hardening rod, using her fluids as lube so she could easily traverse up and down the monster.

To even greater shock to Isaac, Emma slowly took the beast into her mouth, initially playing with it sitting on her tongue, gently kissing the engorged head and swallowing its oozing precum, before wrapping the entire head around her lips with some difficulty. Then, with a look of determination, she slid half of Favorite's length into her velvety mouth, and began to rock her entire body backwards and forwards so that she could pleasure her new boyfriend's unspeaking tormentor. Still, Isaac stroked his own cock, his brain too excited by the sight to process the ramifications.

Daintily releasing Favorite's cock from her throat, Emma spoke to the camera once again, with a frosty tone that contrasted the adoring face she had given to Favorite.

"There are no breaks Isaac, you don't get to sub out from being my boyfriend. You didn't choose a number, so I let the magic coin decide for you."

Her head bobbed downwards onto the cock again, however this time she didn't stop halfway, instead she **** the behemoth through her throat until her soft lips kissed Favorite’s groin, the entire mass of the cock filling her mouth. Instead of immediately going back up, Emma's wide eyes seemed to look up, no doubt staring into her lover's eyes. Involuntarily, she was making **** noises, the end of the giant cock bruising the back of her silky throat, and its girth leaving an impression in her neck. Nevertheless, her pupils remained focused on the face above.

What hurt the most for Isaac is that he could see in the way she stared up at Favorite's face that he was not just another guy, no, her expression was the same one she reserved him when he was conflicted, minus the blowjob. It was a countenance that signified that Favorite was more than a dick stuck in her glossy mouth; he was someone that Emma cared for.

One might think this too much to read from a passing look in a blowjob, but Isaac had seen Emma with other men before, and it was never like this. It had been the same look she gave to the camera when she asked Isaac to be her girlfriend, but what if she hadn't been looking at the camera, what if she was looking at Favorite? What if it really was all another ploy, to humiliate him, to destroy him?

Emma had released her mouth from Favorite's cock, now she stroked it in her free hand whilst grinning upwards at Isaac's replacement. Her arm's motion made soft smacking sounds as she enthusiastically rubbed the ginormous tool. Finally, turning her face to the camera, her eyeliner beneath her left eye was now running down the side of her face, as precum and globs of her own spit sat on her cheeks like puddles on a cobbled street after rain. Sweat had built up on her breasts, little beads of the clear fluid lazily flowed between the crevasse separating her hard breasts. Her smile had turned from one of adoration at Favorite, to smugness as she spoke to Isaac.

"When you said that you would be my boyfriend Isaac, you accepted that this is who I am, not the sweet girl in the library. And yet, the second I ask you for something, you make demands to the contrary. You clearly did not grasp my meaning."

Again, her head motioned downwards, effortlessly pulling the wet cock all the way into herself. She hummed happily as her face sat there, no doubt moving her tongue over the monstrosity like a snake through grass, forcing a deep moan to rise from the pleasured mans lungs and out of his throat.

Coming up again, Emma turned to the phone lens once more.

"So here I am, in the library, sucking my Favorite's cock, not just because I want to, but because I need to remind you who the real me is. You don't get to pick how you are my boyfriend. You are or you aren't. Jerk yourself off faster now Isaac." Her voice was shrill, full of anger.

Isaac began to stroke his cock faster, thoughts of betrayal blown to shreds by his masochist tendencies. Ideas of immense desperation, humiliation and sadness swirled into a storm of pleasure, remorselessly urging him to keep watching the abominable frames flashing before his eyes and for his ears to greedily absorb the sweet and painful noise of his girlfriend worshipping a stranger's massive cock.

Emma began to fully bond herself with the python made flesh, her tight lips sliding from its beginning to its tip, moaning with pleasure as if her mouth was a sexual organ. His headphones were filled with the sound of Favorite's deep grunts, overlayed by Isaac's girlfriend's enthusiastic slurping, a vile symphony that grew ever more intense as her motions edged Favorite closer and closer to blissful release.

Isaac, too, was nearing release, his fractured mind losing control to his primal urges. Inside it felt as if a tsunami was building itself, quickly approaching the rocks that surrounded his mind, his last layer of defence from rejecting logic for the constant, tantalising pleasure that Emma offered.

Suddenly, Emma popped her mouth of the behemoth, stroking it with a determined grin on her face. Still grinning, she stuck her tongue out from her mouth, and with a final grunt Favorite released torrent after torrent of thick, white liquid onto that sweet organ wiggling invitingly from Emma's face, as if it was giving thanks for its efforts.

Rotating herself to the camera, Emma showed off the puddle of cum languishing on her tongue as if it was a trophy recognising her work, and then, with a self-satisfied smile, swallowed it all.

"I can't wait to give you a nice, big kiss baby," blowing a kiss to the lens.

For the second time in a week, Isaac passed out to the sight of his girlfriend lauding Favorite's massive cock. He exploded with greater magnitude than ever before, droplets of his semen falling onto his face as his thinking collapsed in on itself, his body shaking with undecipherable emotion. The same thought swirled around his mind like a broken vinyl player belting out the same segment of a song over and over.

In the library – afterwards – she had – she had – she had kissed him.

She had kissed him, with those lips, she had kissed him, with those lips, she had kissed him, with those lips, she had -- she had -- ...

And, he wanted her to do it again.

His brain was an unconnected circuit, the tsunami of all his desires had smashed through the rocks; Emma had rid him of his inhibitions. He was hers.

Things could never be the same.