An Eye for These Things

DISCLAIMER: Nothing in this story is real or should be considered as such. This story contains elements of cheating, obsession, cuckquean themes, and yes, also features sexual acts between consenting adults. I welcome any feedback and I'm always excited to discuss the story and characters, and chatting/bouncing around ideas for future stories. I hope you enjoy delving into my insane mind.

NOTE: This story focuses very heavily on themes of cheating, specifically in the area of cuckqueaning. It also involves some very twisted (but ideally kinky) character behavior and motivation. It will not be for everyone but I hope for those that it is enjoy it and find some delightfully perverted and smutty material within.

AN EYE FOR THESE THINGS

Jay drew closer to completion the louder the slurping sounds on his dick became. His girlfriend's mouth slobbered all along his shaft, moving like a piston up and down his stiff length. A warm wetness engulfed him -- made his dick swim in spit -- and sent tremors of pleasure racing through his body. He twisted his fingers into the frizzy mass of her hair and yanked her face all the way onto him. His hips thrust upward. His thighs spasmed. His balls contracted. And with one last tongue-swirling suck, he arrived at the door to oblivion.

As the first rush of cum splashed against his girlfriend's esophagus, he cried out her name.

"Unnnhhh, Sofi!"

He came like a firehose. Each pulse like a torrential rush. Cum flooded the throat wrapped around his cock, and the sporadic jerks of the body that tight passage belonged to milked every gooey drop of out of him. With a sigh, he finished, and collapsed back into his spot.

The last of Jay's dick emerged from Eleanor's stretched mouth. Drool coated her chin but instead twisting her lips into a furious scowl over her boyfriend moaning someone else's name, they curled into a dreamy smile. She had cum as well, one of her hands still between her legs idly playing at her wet pussy.

"God, that was hot," she said. Her voice dripped with perverted sweetness. The mattress creaked as she sat up and crawled next to him. Wiping her face and mouth clean, she flopped down onto her pillow. "Did you think about her the whole time?"

"Yeah."

"Fuck yes." Eleanor's satisfied smile grew wider. "I'm so glad you finally came around. You should text her back. Tell her you're looking forward to Thursday."

"Oh, good idea." Still catching his breath, Jay grabbed his phone and texted Sofi. That simple message turned into a back-and-forth exchange that lasted twenty-five minutes. And the entire time, Eleanor leisurely continued playing with herself until she fell asleep.

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Jay and Eleanor first met Sofi a few weeks into their relationship. They hit it off with the spunky yet sometimes awkward girl right away and the three of them exchanged numbers so they could hang out again in the future. That first hangout was proceeded by a second, and then a third, and then several more after that. Their casual acquaintance quickly morphed into a full-blown friendship, and through it all -- through movie nights, lunches and dinners, and various other outings -- one thing became very obvious to Eleanor: Sofi had a huge crush on Jay.

They both got along with Sofi and the three shared various interests with one other, but there was no question in Eleanor's mind that Sofi and Jay overlapped more, especially when it came to his nerdier pursuits. Sofi got technical about gaming, caught his obscure references, and read the same fantasy books as Jay. Her boyfriend seemed oblivious to it all, but Eleanor always noticed the sparkle in Sofi's eye when she laughed at his jokes or how she glanced his way with longing when he wasn't paying attention.

"It's kind of sweet," Eleanor said. The two were lounging in the living scrolling on their phones, with Eleanor laying across the arms of their chair and Jay relaxing on the couch. When Eleanor decided to tell him about Sofi's interest in him, he didn't seem to believe her at first, but he finally acknowledged it once she told him about all the little things. "She's really into you."

"Yeah, well, it'd never work," Jay laughed. "She's not really my type." A creeping chill ran over him when she didn't respond, and he flicked his eyes over to her. The perplexed image that greeted him turned his blood to ice. "Not that, uh, it would matter if she was. But she definitely isn't."

"How can you say that?" Eleanor said and flipped around to land on the cushion. Jay scrambled up in his seat, ready to backtrack, to apologize, to clarify, but his protests ended up dying in his throat when she continued. "What do you mean she isn't your type?"

Eleanor had no problem admitting that she found Sofi's crush cute but held back from confessing just how much the notion made her insides quiver... or how when she thought about it sometimes her hand instinctively drifted up her legs. Jay's response, however, almost made her feel insulted, not just on Sofi's behalf but about her own hidden desires.

"Uh, I dunno," he said, unsure of how to respond. The question threw him, and he believed he saw a trap lying in wait. A single wrong step could set it off and cost him a limb. "I feel like there's no good answer here?"

Eleanor's eyes nearly hit the back of her skull. "I'm not looking for a good answer. I'm looking for an honest one. How are you not super into her? You both have so much in common and she's so cute."

"I guess? I just don't really see her that way." He rubbed at his temple, confusion and aggravation building underneath the surface. "You make it sound like I should be dating her." Eleanor shivered. She opened her mouth, ready to object again, but he stopped her before she could say anything. "Can we just drop it please? This is a ridiculous thing to fight about."

"Fine," Eleanor said, stone-faced. "I'll drop it."

She didn't.

Eleanor prided herself in her matchmaking skills. She predicted with high accuracy which couples both celebrity and familiar would last. She hooked up more than a few of her single friends over the years to great success. And years of romance novels and reality shows honed her ability to pick up on who was attracted to who. The idea of her incorrectly assessing the situation between Jay and Sofi seemed absurd.

So, whenever they all hung out together following that tense conversation, she spent a lot of time noting Jay's reactions and trying to catch him staring at Sofi. Whenever they made plans, she kept hoping to see a spark of excitement in his eyes. Whenever she scrolled Instagram, she checked Sofi's likes to see which pictures he may have double tapped.

None of it paid off. Jay seemed wholly uninterested in the other girl, much to Eleanor's chagrin.

She simply could not understand. The more she considered it, the more it made sense to her that her boyfriend should find Sofi appealing. The more she thought about their conversations and interests, the more she believed that they'd work really well as a couple. And the more she pictured Jay giving into the desires he claimed not to have and making out with their friend in a passionate frenzy, the hotter and more turned on it got her. The idea of Jay and Sofi together infected Eleanor's mind and spread to her every thought like a perverted disease.

Getting them together became more than a mission. It became an obsession. One that seemed impossible the more time went on... until one particular night. The night of Eleanor's birthday.

Eleanor usually kept her birthdays pretty low key. She preferred a chill night at home over anything elaborate. This year, however, her boyfriend of six months decided to splurge and booked them a reservation at a fancy restaurant. She was reluctant at first but came around to the idea of dressing up for a night and bought herself a new sleeveless top that she paired with black leggings. The cowl neckline complemented her modest bust and the tights highlighted her long legs. With her wild brown hair tied into a messy bun, she looked positively spectacular, and Jay kept darting his eyes over to her and checking her out. It seemed he only had eyes for her.

At least until Sofi walked through the door.

Their dorky friend had understood the assignment and shown up in a tight black dress that conformed to every inch of her body. Her thick, dark hair was out of its signature braid, and although she still wore her oversized glasses, the eyewear ended up giving an innocent contrast to her overall seductive look.

For the first time ever, Eleanor caught her boyfriend gawking at their friend. It was fleeting. It was all too brief. But the reality of her months-long quest proving fruitful got Eleanor's heart racing and her panties moistening.

"Hey Sof," Jay had said as Sofi hugged her and wished her happy birthday. "Love the dress."

That simple compliment had driven Eleanor wild with lust for the rest of the evening.

Later that night, they stood making out in the middle of Jay's bedroom, his tie already off and her hair out of its bun. His hand cupped her ass and Eleanor grinned, imagining him picturing Sofi's much rounder butt in his palm. She knew Jay enjoyed groping her slim but firm derrière, but there was no question the fun that would come from squeezing and molesting an ass like Sofi's.

"Mmm, you looked... so good... in this outfit," he panted.

"You know who else looked good tonight?" she whispered. Jay's lips trailed down her neck. "Sofi."

She gasped, her eyes widening with delight when he gave her ass a sharp squeeze at the mention of their friend's name. Quick and impulsive -- and brushed past like it never happened.

"I... guess," he said. Uncertainty peppered his voice. He tugged at her top and slipped it over her head. Jay loved the sight of Eleanor's breasts, lemon-sized and teardrop shaped, and he bent over to latch his mouth onto her rose-colored nipple. "She looked pretty good."

"Pretty good?" Eleanor dug her fingers into his hair, holding his head to her chest. "She looked fucking hot." Jay said nothing but continued to lick and suck at her tits. "That dress on her... mmmm..." She reached between their bodies to rub her hand up and down his crotch, excited to find an erection pushing into her palm. "A regular shortstack smokeshow."

Jay released her breast and pulled back to his usual height. His brown eyes swam with a mixture of confusion, lust, and drunkenness. "I... I don't know what you want from me right now."

Eleanor's own alcohol-infused state of arousal had lain waste to her inhibitions, torn down her filters. For months she dreamt of an opportunity like this, a crack in Jay's armor. In a moment of reckless desire, she stated exactly what she wanted right then. "I want you to jerk off to her."

Jay gaped at her, mouth open and face in total disbelief... but his cock twitched under her hand.

"What? I... there's no way. Is this like a weird test?"

"No!" Eleanor said. One hand still groped and stroked at him; the other rubbed at his chest from under his half-unbuttoned shirt. Eleanor's head spun with flashes of Jay beating off to Sofi, pumping his cock and calling out her name. She lowered his zipper, snaked his stiff prick through his fly, and slowly jacked her hand up and down his length. She kissed him hungrily, physically and mentally grasping at whatever she could to convince him of her seriousness. "It's what I want. My special birthday treat. I'll even masturbate to you doing it."

"I... I thought you were going to drop this." Despite his protests, Jay kissed her back, his hand slipping under her tights to find her wetness.

"I will," she groaned, both of them fondling each other. "If you want. After this." She shivered and quaked, gripping the back of his neck for support as he played with her lower lips. He didn't respond, didn't say anything, but the precum coating his cockhead told her his doubt was wavering. "I saw how you looked at her when she walked in. You can't tell me your dick isn't hard for her."

"Okay," he choked out. "I'll do it."

If everything she'd said hadn't persuaded him, the mini-orgasm that soaked his fingers did.

Eleanor broke their kiss and stumbled backward. Her amber eyes burned like wildfire. She panted heavily, nipples stiff, soft skin flush. "Let me get my iPad. I bet she posted a picture of her outfit from tonight."

Sure enough, she found an image that Sofi had posted, taken by Eleanor herself earlier that evening. The picture had captured the shorter girl from head to toe, turned mostly to the side but twisted toward the camera, the curves of her body on total display. A smile on her face, Eleanor handed Jay the iPad and kissed him on the lips before sliding her tights off her legs and crawling onto the bed.

Jay watched her slink away from him. Her sheer panties left her ass almost entirely visible, and he followed the swaying cheeks with his eyes as she made her way to the headboard and then turned around to face him. Bracing her back against the wall, she spread her long legs and drifted her hand down to her panty covered crotch. His girlfriend really was going to finger her extremely wet pussy to him jerking off to Sofi. His horny dick throbbed with arousal even while his brain swirled with confusion.

Even beyond the alcohol clouding his mind, Jay couldn't understand Eleanor's fixation on their friend. Or more specifically, the idea of him being attracted to their friend. When she had first brought it up, he had thought she was trying to snare him in some sort of trap or that she was testing his loyalty. He had also thought he had gotten her to let it go. Yet here they were: her rubbing up and down her slit from over her panties and him holding an iPad with a picture of Sofi on it, his rock-hard cock sticking out of his fly and leaking precum.

He had meant what he had said before. Sofi wasn't his type. He preferred girls like Eleanor. Tall with pale skin and a lithe body. She didn't have huge breasts or a big ass, but she possessed a statuesque sexiness that was further enhanced by a vivacious sexual appetite. She was the type of girl guys fantasized about.

However, ever since she brought up Sofi in that way, the idea had needled at him, pricking holes in his original resolve. He had even found himself flipping through her Instagram a few nights ago, looking at, but making sure not to like, her photos. He had purposefully avoided comparing her to Eleanor, took in her qualities that popped in the various images, and had ended up getting a small stir down below. She was more of a nerdy and dorky type, a petite geek, but he had to admit, she was attractive. But nothing beyond that. Nothing noteworthy.

Until tonight. When Sofi walked into the restaurant, something cracked inside of him, some sort of self-imposed barrier, and for a moment, he saw her in a different light. He saw her as sexy.

His gaze turned to the iPad, to Sofi in that dress, her hazelnut skin complementing the black perfectly. He didn't want to stare earlier and had pushed his initial reaction aside. But now he could really take her in, study all those details about her that he often ignored and suddenly now noticed. Her short stature that gave her a level of spunkiness that often delighted him. Her large glasses that, while undoubtedly dorky, he found rather cute. Sure, she was a little softer in the midsection, especially when compared to...

He stopped himself. He hadn't intended to compare them, but it was really hard not to. However, if that door was open... Sofi's breasts seemed bigger than Eleanor's miniature mounds. Her dress tonight really emphasized that fact, highlighting the shape of her chest. And down below, her small feet led up to nice calves, shapely thighs, and that huge ass that curved out enticingly. He'd never tell Eleanor, but he always was more of an ass man, and Sofi's put every other girl to shame, especially his girlfriend.

Without even thinking about it, he wrapped his hand around his shaft and started stroking his cock. His eyes concentrated on the image of Sofi and a low whine -- not of anguish or sadness but of aroused delight -- erupted from the bed.

"Oh god, you're doing it."

Pumping his fist across his length, he glanced toward Eleanor. His girlfriend still reclined in the same spot, but her panties had been pushed aside and two fingers were buried in her wet snatch. Eyes lidded with lust and mouth hanging open, she caressed one of her tits and watched him intently. She looked sinfully hot. The picture of eroticism. But as much as he wanted to keep staring at her, she wanted him to get off to Sofi -- and part of him wanted it, too.

Did he really want to choose Sofi over Eleanor in this moment?

He returned to the photo and another long whimper echoed from above.

He assured himself that this was a onetime thing. That he was doing it for Eleanor and that this would be the end of it. That it wasn't because his cock throbbed in his grip over thoughts of their friend. He dropped the iPad onto the mattress and the enticing image on screen inspired his mind to wander.

He fantasized about Sofi out of her dress but still in those glasses, her lips curled into a teasing smile, dimples in her cheeks. He pictured her naked body, the curve of her breasts, the thickness of her thighs, the question of what lay between. Did she shave? Eleanor did but he imagined Sofi did not. Judging by the dark hair on her forearms she probably had a nice bush of equally dark hair over her pussy.

"Oh, fuck," he gasped, more and more precum lubricating his strokes. His fist flew across his shaft as he pumped his cock in rapid jerks. The image in his head shifted and Sofi's fat ass filled his mind. It was so big. So much better than his girlfriend's. With fast, short breaths he envisioned that wide rear bent over in front of him, what it would look like rippling from the impact of his hips slamming into her, from him hammering her cunt with his dick. "Aggghhh! Fuck fuck fuck!"

Jay's balls tensed. A rush of pleasure originating from deep within his loins exploded outward and he came, firing ribbons of cum onto the iPad, dousing the picture of Sofi.

On the bed, almost folded in half from having slid down the wall and not wanting to stop pleasuring herself, Eleanor cried out in joy, crushing her breast in her hand as she erupted in climax. Her cunt had been swimming in her juices, her fingers plunging into her slick wetness, while Jay masturbated to their friend. When he started, she had almost cum right then but her delight at it happening nearly ruined the moment, drawing his attention away from Sofi and back to her... but only for a second. Seeing him return to the image on the iPad, witnessing him frantically beat off to her, and then spewing his load onto her picture, it all was too much.

He had gotten off to her. Jay had jacked off to Sofi. And from the amount of jizz deposited onto the iPad and mattress, had cum harder than he ever had with her.

Eleanor had promised she would drop it after this if he wanted, but after witnessing that, there was no way she was going to rest until all that cum was inside of their friend. Thankfully, second steps are easier than the first.

Once a guy jerks off to a girl, he can never see her the same way again. It changes him. Changes how he thinks about her. Prior to that night, Eleanor had trouble ever noticing Jay paying attention to Sofi. Now the small girl seemed to dominate his interest. She'd spot them laughing together, his gaze slyly darting to her chest. Whenever Sofi left the room, she'd notice him taking in the other girl's hips and curvy rear. And whenever Sofi's arm playfully bumped against his, she'd catch the light blush of his cheeks and giddy smile on his face.