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An Eye For These Things

"A girl thinks her boyfriend should be more into their friend"

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9.7k words 9.7k words

Author's Notes

"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. It also involves some very twisted (but ideally kinky) character behavior and motivation. <p> [ADVERT] </p>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."

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 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 of 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.

-------------------------------------------

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 in to 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 that 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 short stack smoke show."

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. With 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 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 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 at this moment?

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

He assured himself that this was a one-time 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.

Eleanor even stumbled upon him masturbating in the shower one day and she just knew he was doing it to their friend. Her boyfriend blowing his load to Sofi in secret led to her own masturbation session in the shower shortly afterward.

Meanwhile, on the emotional front, Eleanor continued her assault, going out of her way to get Sofi and Jay to spend more one-on-one time together and to remind them of their shared interests. She'd excuse herself from the room to give them more chances to chat and talk about the things they both liked. She'd bring up something in conversation she knew Sofi or Jay enjoyed that she didn't. She even went so far as to skip out on a movie so he and Sofi could text about it without her. This let them have their own private messages outside of their shared group texts.

Eleanor never pushed it or brought it up with Jay directly. She just shifted some pieces around, paying attention to the board, and let everything take its course naturally, patiently waiting for the right time to make her next move. Which finally came about a month and a half after the birthday incident, in the middle of her and Jay having a somewhat lackluster sexual encounter. Eleanor noticed her boyfriend's distracted gaze and knew precisely what occupied his mind. Because earlier that day, a group of them had gone to the beach – a group that included Sofi.

"It's okay," Eleanor said. "You can think about her."

"What?" Jay's voice feigned surprise and confusion but his cock hardened and throbbed inside of her. "I don't…"

"Come on. Just close your eyes," she brushed her fingers across his eyelids, "and picture her in that bathing suit."

Jay let out a shuddering breath... and pushed himself back into her.

"Yes, that's it," Eleanor gasped. "Think about her on the beach in that two-piece. Ooohhhh. How it, mmf, showed off those jugs of hers. How it, ungh, stretched and clung to that, big ahh-ass. Fuck. And those thick, sexy thighs. UNNGH!"

Jay's pumps picked up in speed and intensity the more his girlfriend described Sofi from earlier. Eleanor herself grew wetter with his every enthusiastic thrust, her small breasts bouncing with every slam home. It was so sinfully twisted having her boyfriend fuck her while thinking about another woman, but in Eleanor's mind, it was the woman that he should be fucking instead of her. The one better for him.

Spurred on by Eleanor's words, Jay recalled every minute detail about Sofi from earlier that day. Ever since he first jerked off to her almost two months ago, he couldn't stop thinking about the other girl. Every time they hung out, he checked out her body and thought about her sexually. He found her dorkiness so endearing, her dark hair and caramel skin so enticing. Seeing her in that bikini, his mind couldn't stop wandering back to her lying on the sand, her coming out of the water, wet swimsuit molded to her skin. Eleanor should have been enough to get him off but instead, he just kept thinking about Sofi.

Unsurprisingly, Eleanor had noticed. Also unsurprisingly, she was once again encouraging it. But this time, he didn't fight it. He embraced it.

He slammed into his girlfriend, his mind filling with images of Sofi's bikini-clad body.

"Imagine her out of that bikini," Eleanor said, shifting memory to fantasy. "Imagine her, oh fuck, on this bed instead of me. Imagine her legs spread for you, her pussy around your cock. Oh! Oh! Oh! Yes!" Jay hammered into her hole, pounding into her with unbridled, unleashed desire. "Imagine that cute face, unnh, squealing in need. Those tits flopping as you, ah ah ah, fuck her raw!"

The fantasy in Jay's mind flickered back and forth. Hearing Eleanor's voice brought up her body, but the words conjured Sofi's. Again and again, they flipped and switched. Eleanor's mane of brown frizz. Sofi's thick waves of black. Eleanor's small perky butt. Sofi's big sexy ass. Eleanor's long and lithe form. Sofi's short and curvy frame.

"That's it. Fuck her. Fuck her and cum. Blow your load into that sexy short-stack slut. Fucking cum while imagining yourself pumping Sofi's cunt full of your jizz!"

The image locked and Jay buried himself all the way inside of her and exploded.

"OOoohhhHHHhhh fffuuuuccckkKKKKkk!"

Eleanor screamed and came from the sensation of her boyfriend's gooey spunk flooding her insides while another woman filled his thoughts. Her walls spasmed around his erupting cannon, her orgasm soaking him to the metaphorical bone. They tumbled, twisted, and fell, both of them spinning around a unifying, singular center of gravity. "Oh god. Oh fuck."

In the afterglow of their shared experience, one thought kept Eleanor floating in ecstasy: there was no going back now for either of them.

Following that revelatory night of passion, everything about their shared, twisted desire regarding Sofi was laid out on the table between them. No longer did they need to avoid the subject or hide their feelings, and their entire relationship shifted and changed to accommodate their mutual depravity. Jay fucking Eleanor while she described Sofi in her stead became a permanent part of their animalistic couplings. But it was so much more than just what went on inside the bedroom.

Jay openly flirted with Sofi without fear of Eleanor getting upset. Eleanor talked about Sofi without Jay trying to deny his lust. Jay and Sofi chatted more and more, and Eleanor rubbed herself to mind-bending orgasms remembering how they looked at each other, knowing that she ever so slowly was getting them closer and closer to hooking up. Eleanor and Jay could give in to their arousal and perverted emotions without fear of judgment or restraint.

They refused to talk about the why of it, both content with the idea that they stepped over the messy puddle in the path to get closer to the ultimate destination they both wanted. It was better for them not to confront how Eleanor's pride and stubbornness mixed with perversion to get them there or how Jay's unconscious biases that influenced his views on dating and attraction prevented him from accepting the truth in the first place. They'd much rather sink further and further toward the bottom. Drown in debauchery and lust.

And sink and drown they did.

Like when Eleanor leisurely stroked his dick while he texted with Sofi, turning even mundane acts with the other girl sexual. Or when Jay fucked her from behind with the iPad balanced on her back, a picture of Sofi pulled up onto it. Or when they celebrated their nine-month anniversary with Jay fucking Eleanor's mouth while calling out Sofi's name.

-------------------------------------------

"How'd it go?" Eleanor leaped off the couch when Jay walked through the front door, anticipation and excitement propelling her upward. She hadn't seen him for a total of fourteen hours. Fourteen hours that he got to spend just with Sofi.

They'd been working toward this day for weeks. All three of them had taken a day off to go to a theme park together but two days before the trip, Eleanor "had something come up" and couldn't go. Sofi suggested rescheduling but Eleanor said it was okay and that she and Jay should just go without her. As Eleanor expected, Sofi "reluctantly" agreed to the plan.

The diminutive dork loved theme parks. It was the perfect place, the perfect first date, for her and Jay. Eleanor even made sure not to text either of them all day, not wanting to interrupt anything or remind them of her. She wanted them lost in their own magical world, with eyes and thoughts only for each other.

"Ugh." Jay dragged himself into the living room and fell into the couch. "It was going great. We had an amazing time at the park. Rode a bunch of rides. Shared food. Had a few drinks. I've never had so much fun."

In any normal relationship, a statement like that would break someone's heart. In their relationship, it made Eleanor's panties wet.

"Okay, well, what happened?"

"We made out. When I dropped her off."

Eleanor's eyes went wide, and her heart almost hammered through her chest. She wanted to shove her hand down her pants and finger herself to orgasm, but she held herself back. Clearly, there was more to the story.

"Why are you upset? Isn't that what we wanted?"

"Yes, but... We went at it for a while but when I went for more she stopped."

"What? Why?" A sense of déjà vu washed over Eleanor, taking her way back to that tense conversation with Jay so long ago in this very living room. She hadn't misread Sofi. There was no way. "No chance she doesn't want to fuck you."

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Jay sighed. "It's because she didn't want me to cheat on you. She said it didn't feel right doing something like that to you."

If Sofi only knew how very right it felt.

Eleanor paced back and forth in front of the couch, the gears in her head turning and spinning. The image of Jay and Sofi kissing passionately kept interrupting her thoughts, but she shoved it to the side, demanding it wait until she solved this problem, until she removed this annoying and bothersome snag. She came to an abrupt stop and checked the time on her phone. "How long ago did you drop her off?"

"About fifteen minutes?"

Eleanor grinned.

"Okay. I have an idea, but we have some time to kill first." Stepping toward him, she pushed his knees apart and lowered herself down between them. Eleanor unbuttoned her boyfriend's shorts and lowered his zipper, then reached inside to take out his meaty dick. Holding the shaft in her hand, she leaned forward to press her lips around its tip.

"Until then, I want you to tell me about kissing her," she tossed her hair over her shoulder, "while I suck you off," and took him into her mouth, sinking all the way down until she gagged and slipped him into her throat.

Jay moaned and tangled his fingers into her hair, the wet warmth of his girlfriend's mouth enveloping his shaft. He held her to his base for a breath before allowing her to draw back and then plunge down again. She took her time, going slow, intent on prolonging his climax and getting both the story and his cum out of him.

Jay never did much dirty talk before all this. Even as they got more into it, Eleanor usually did the work, describing Sofi and encouraging his fantasies when they had sex. Her going down on him put the reins in his hands, since her mouth was preoccupied, and having him reminisce worked much better, equally well for him and for her own needs.

"We pulled up to her complex and I, ah, parked so I could walk her to her door," he started. Eleanor swirled her tongue around his head. The romantic gesture made her pussy drip, and she dropped a hand to her lower lips to play with herself.

"Once we got there, I told her how much I enjoyed the day, just the two of us. She smiled and said, unf, she really enjoyed it, too. Then I... I said I was glad you couldn't make it. That I had a better time with her than I would have if it was all three of us." Eleanor bobbed her face faster onto him, her fingers flying across her slick slit, gliding across her clit. "Ungh! I don't remember who started it, but then we were kissing."

Eleanor groaned, and the vibrations of her throat made his dick quake. She came up for air, pumping his cock with her hand while she caught her breath. "Keep going. Tell me more."

He laid his head back and closed his eyes. "It felt so good kissing her. It wasn't a quick peck or a slow build-up. We had... our tongues in each other's mouths immediately." Jay gasped, Eleanor's sucking growing wetter and sloppier, more intense. He recalled the plumpness of Sofi's lips, the sounds of their desire in the hall. "We made out for I don't know how long. Her body against mine, my hardening cock pressing into her. I know she could feel it. Mmm. And I just had to finally feel her ass. She gave the cutest little whimper when I grabbed it."

Slime ran from both of Eleanor's lips, coating her chin and thighs. Mouth stuffed with cock, pussy crammed with her digits, her mind filled with the image of Jay and Sofi making out like lust-drunk teenagers. She pictured Sofi tilting her face up to meet Jay's lips, their tongues wrestling and wrapping around each other, Jay's hand groping and squeezing Sofi's fat ass.

Eleanor frigged her clit, and her breaths came in short, fast bursts through her nose. Months of teasing and talking and building sexual tension between Jay and Sofi had finally broken, and it made her so aroused, so intoxicated with perversion. She whimpered around her boyfriend's cock, begging him to continue.

"I loved how amazing her ass felt in my hand. So soft and big. I had wanted to grab it all day at the park. But then, when I tried to go under her shorts... that was when she stopped me." Eleanor let out a whine of disappointment. "If she hadn't... I would have fucked her right there in the hallway."

The next sound Eleanor made, beyond the glk glk glk of her face getting used, was a squeal of delighted approval. An electric jolt of pleasure rocketed through her body as she came, a blaze starting from between her legs and burning through the rest of her. As her orgasm consumed her, the fingers in her hair tightened their grip and drove her face up and down like a piston, hips jerking up to meet her descending lips.

Jay's cock expanded in her throat, depositing his thick load straight into her gullet while he imagined emptying himself into Sofi in front of her apartment. Once done, he released his hold on Eleanor's head, and she withdrew from his cock with a gasp. They sat there for a handful of minutes, recovering from the explosive expenditure of their super-charged sexual deviancy.

"What was your idea?" Jay asked after his breathing returned to normal. He lifted his head off the back of the couch to gaze down at Eleanor's panting, spit-covered face. An excited and almost manic twinkle overtook her eyes.

"You're going to break up with me."

"What?" Jay sat up and tucked himself back into his pants. Eleanor leaned back onto her haunches and gave him a quizzical stare. Kneeling there, her frizzy hair a mess, and having just gotten her face fucked, Eleanor looked ravishing, seductive. The idea of breaking up with her, despite how much he wanted Sofi, conflicted with the thought that any rational guy would want to stay with the depraved beauty in front of him. "But... I don't want to break up with you."

Eleanor rolled her eyes and got up to grab some tissues and clean her face. "We don't have to actually do it until you two get together. But in order to get that to happen, we can tell her that we did." She sauntered back over to him, that twisted look back in her eyes. "She might not want to be 'the other girl' but I don't mind playing that part while you guys are just dating... at least until you become official."

Another puddle in the path.

Eleanor again seemed content to just walk over the murky water but unlike the first time, Jay stopped and hesitated. Two things tore at him, pulling him in different directions. Being in a relationship with Sofi or continuing to have fun with Eleanor. He thought he knew what he wanted, but faced with the reality, he suddenly wasn't sure. They should talk about it, confront their feelings and consider where everything might actually end up. But instead, he stepped right over and joined Eleanor on the other side.

"As long as we're not actually breaking up... and we can still have sex."

"You can use my mouth as much as you want," she said and reached down to give his rallying soldier a squeeze. "But the only pussy this cock gets is Sofi's."

They compromised on that one. Eleanor allowed him one last fuck right there in the living room while they waited to text their friend. Of course, the entire time they went at it, kneeling on the cushions with Eleanor bent over and off the armrest, Jay hammering her well-lubricated love tunnel with hard and frantic thrusts, she moaned about Sofi's pussy being the only one that'd get his cum from now on. True to her word, when Jay's jerks turned jackrabbit fast, she dropped to the floor, opened her mouth, and with wild eyes said, "Show me how much cum you're going to deposit inside of that hot cunt."

For the second time in less than an hour, Eleanor took a load into her stomach meant for another woman, and it made her explode in debaucherous delight.

When enough time had passed, enough for a fight to have occurred, they texted her.

Despite feeling rather confident in her assumptions about Sofi's feelings, Eleanor decided to throw one last test out there. Rather than have Jay send the news, she did, texting simply that she and Jay had broken up. Then they waited. It took a few minutes but eventually, the phone buzzed with a new message. Not Eleanor's but Jay's. She smiled.

"Did you break up with Eleanor?!"

"Should I respond and tell her yes?" Jay asked. "Tell her to come over."

"Oh my god," Eleanor sighed, shocked at his inability to understand tact. Despite having cum twice, he was somehow still thinking with his dick. "Give me the phone."

"Yeah," she wrote back. "I had to."

"Because of me?"

Jay perked up, again thinking now was his chance but Eleanor ignored him, telling the other girl, "Maybe? I don't know. Just give me a few days and we'll talk."

Satisfied, she handed the phone back to a confused Jay. "You can't just jump into bed with her right after breaking up with me." Eleanor's phone buzzed. "It'd make her feel awful afterward."

"omg! I'm so sorry," the text read. "Did he say why?"

"Just that it wasn't working out," Eleanor texted back. Sofi didn't respond right away, probably unsure of how to, so Eleanor forged ahead, guiding Sofi along the path she needed her to take. "Honestly, it's probably for the best. Great sex but we weren't that good of a match. You're probably more his type lol. I'll be okay. Gonna stay with a friend for a while."

Three dots appeared, disappeared, and then appeared again.

"Lol, I'm glad you're taking it well. I'm here if you need me."

"There," she said after telling Sofi thanks. "Now when you see her again, you'll both be over me and focused on each other. You'll get her on her knees in no time."

Eleanor's prediction came true when Sofi took Jay's dick into her mouth three days later.

While the two of them met for dinner to talk about everything, and for Jay to finally confess his feelings, Eleanor pleasured herself alone in the apartment, fingering herself to dual orgasms thinking about what might happen later that night.

While Jay and Sofi playfully flirted and enjoyed a shared meal, she pumped her fingers into herself in twisted excitement. While Jay told Sofi that he broke up with Eleanor because he wanted to be with her, she trembled and shook and groaned imagining Sofi getting wet at the news. And while they got into Jay's car to head back to the apartment together, she wailed in climax thinking about them fooling around in the exact same spot where she rolled in orgasm.

As much as Eleanor wanted to stay and watch what happened, she knew she couldn't be there when they got back. She ended up going for a long drive, giving them a few hours, before returning with a pounding heart and quivering pussy. She walked in to find Jay beaming in the living room with an orgasmic glow about him.

"How'd it go?" she asked, her eyes blazing with lustful fire. She slinked onto the couch and curled her legs under her. At that moment, she and Jay acted less like a couple and more like roommates and it sent an excited shiver down her spine. "Tell me everything."

"Dinner was great. We didn't talk about you too much. She asked if we broke up because of her. I said it was a lot of things but a big part of it was that, yeah, I did have feelings for her. I guess that was enough because she didn't ask much beyond that. The rest of the time, we just talked and hung out. But, there was definitely sexual tension in the air. After a few drinks, she asked how long I'd been into her, and I told her, since your birthday, when she wore that dress. She blushed at that... and said she wore it to get my attention."

"Mmmm, fuck yes." A pleased grin stretched across Eleanor's face. She leaned closer to him, the fire in her gaze almost an inferno. "Did you fuck her?"

"No," Jay said with a sigh. "She didn't want to rush it." Eleanor almost screamed. "But... she did suck me off."

A whine started deep in Eleanor's throat and evolved into a desire-soaked groan. She fell backward onto the arm of the couch and spread her legs to expose her bare cunt. She hadn't worn any underwear, which allowed her fingers quick and easy access to her slippery lips.

"Was it good?" she gasped, her clit buzzing with energy. "Did you enjoy getting your dick sucked by that cute little dork?"

"God, yes."

Eleanor sank two fingers into her gushing hole and whimpered in need. "Tell me."

"We made out for a while, right here in this same spot," he said, summoning into Eleanor's mind the image of him and Sofi passionately kissing a few feet away from her. She heard their lips smacking, pictured their tongues swapping spit, and thought about Jay grabbing the other girl's breast. "Her tits are great. Bigger than yours but soft and squeezable."

Just the knowledge of what happened was enough to get Eleanor's pussy soaking wet. "Then her hand drifted down my chest. She was a little shy about it and went slow but after a pause, she went straight for my crotch. She moaned into my mouth when she felt how hard I was."

Eleanor panted and struggled for breath. She could cum just from what she heard so far but she wanted to hear more. She needed to get to the best part.

"Once she did that, she slid to the floor and scrambled to get my dick out. She looked so hot down on her knees." Eleanor pictured Sofi between his legs, working to get his cock out of his pants, gasping once she felt his thickness in her hand. "She smiled when she pulled it out and just kind of stared at it like she was admiring it. Then she whispered, 'god, I've wanted this,' and wrapped her lips around it."

"Yes! Me, too, Sofi. MMmmmMM, fuck. Me, too." Eleanor's butt arched off the cushions, a quake of ecstasy rushing through her. She held her hips in the air, small pulses of pleasure rippling through her pussy, before dropping back down. "Faster. Keep going. How much of you was she able to take?"

"Almost all." Jay wasn't huge but was larger than average. Over half was an impressive feat for any girl. "She gagged a little bit but that just made it hotter. I couldn't believe Sofi was sucking me off, and watching her face bounce up and down my cock, it was so good." Eleanor imagined their friend's stretched lips sliding up and down Jay's pole, her spit and saliva coating its length.

She listened to the soft gags and chokes in her head, the light slurps and quiet moans of Sofi blowing him. Her fantasies drowned out the sounds of her own wet slit, fingers frantically moving across her lips and clit. "She went faster and faster, her glasses slipping down her nose. I warned her when I was about to cum but she just sped up. She only stopped when I came."

"Did she... did she... ungh..."

"Yea. She swallowed."

Eleanor's face twisted into a silent scream and her thighs parted wide. Stomach muscles clenching, she exploded in orgasm as she imagined Sofi's throat bobbing as she guzzled down Jay's copious load. It had taken Eleanor months to decide to swallow Jay's cum and Sofi did it on the first go, filling her stomach with his jizz.

By the time Eleanor's climax ended, and she crashed back down, she nearly passed out from bliss, a fantasy of Sofi sitting back and licking her lips playing in her mind.

As much as she enjoyed hearing about Sofi sucking Jay off, as much as her technical ex's description of events brought her to one of the best orgasms of her life, she knew that when it came to them finally consummating their relationship, Sofi spreading those thick thighs and letting him pump his dick into her, hearing about it wasn't going to be enough. She needed to see it. And laying there on the couch recovering, her mind floating in a post-orgasmic dream, she decided that one way or another, she was going to find a way to make that happen.

For once, Sofi's insistence on taking things a little slower worked out in Eleanor's favor. While Sofi and Jay went out twice more in the following week and a half, they never went much further than they did that first time. Instead, the second date culminated in Jay fingering her, him bringing the cute girl to climax while making out with her on the bed and the third ended with her letting him wrap his hands into her thick braided hair and fuck her mouth until he came down her throat again.

Both instances and their subsequent detailing by Jay gave Eleanor enough masturbation fodder to tide her over for a while, but it also allowed her enough time to order and set up the high-quality cameras in the bedroom. So, when it finally did happen between Sofi and Jay, she was able to spy on every sordid detail like she was right there in the room witnessing it. The momentous occasion, at last, came a few days after Sofi's face fuck, and Eleanor booked a hotel room to privately watch the perverted coupling play out. Screen-casting them onto the television, she brought herself to body-quaking orgasm after orgasm, committing every second of debauchery to memory.

By the time they made it to the bedroom Jay and Sofi were already half undressed. Crashing through the door and into the frame, they kissed with wanton desire, their hands roaming all over each other's shirtless bodies. It was her first instance of seeing them together like this and the raw passion they expressed toward one another's bodies made Eleanor tingle in delight.

Her breath caught in her throat and her fingers teased circles on her slick lips as Jay's hand snaked up Sofi's back to the clasp of her bra. With a flick of his wrist, the garment came undone, and Sofi slipped it from her shoulders and tossed it away.

Although Eleanor felt no attraction toward Sofi herself, seeing the other girl expose her breasts gave her a thrill. They were at least a cup size bigger than Eleanor's and hung heavy on her chest, bouncing and swaying in ways Eleanor's never could. Jay grabbed and squeezed and caressed the caramel mounds before lowering his mouth to her dark nipples, and both Sofi and Eleanor tossed their heads back and moaned in pleasure.

Pushing his head away, Sofi spun Jay around, backed him up against the footboard of the bed, and lowered herself down to her knees. Because of her height, she couldn't sit back on her haunches and had to remain elevated while unbuckling and dropping his pants and underwear to the floor.

Once his shaft came out into the open, she leaned forward, and Jay tightened his grip on the bedframe. Eleanor's first orgasm rushed through her watching Jay get his cock sucked. The wet sounds of Sofi's mouth bobbing and gagging on his pole made her hips jerk but seeing his thick cock spear the other girl's face drove her toward climax. Sofi sucked him for a good while, picking up in speed, slowing back down, holding herself onto him, and gagging, coating his cock in her saliva.

Jay seemed almost ready to burst and he finally let go of the footboard to back her off his dick. She giggled up at him and gave his tip a quick lick. He shivered in delight.

"I want you to fuck me."

Those words sent Eleanor into a second screaming orgasm.

Sofi stood up and pushed her tights and panties down and off her wide hips. For the first time, she was fully naked before them, and Jay and Eleanor both dropped their gazes between her thighs to take in the sight of her pussy. As Jay suspected, Sofi possessed a bush of dark hair that topped her plump outer lips. Like so much between her and Eleanor, the size of them also contrasted the other girl's and hid Sofi's inner lips from view. However, the biggest difference between the two women came into the picture when she turned and moved toward the bed.

"Wait." Jay grabbed her arm and stopped her in her tracks. His cockhead drooled at the sight in front of him. Even Eleanor paused in her masturbation to gawk slack-jawed at the absolutely stunning vision of Sofi's ass. They knew it was big but the curve of it, the firm thickness of those globes, was nothing short of breath-taking, cock-straining, and pussy gushing. "Jesus Christ."

Eleanor's eyes grew wide as Jay dropped to his knees. Her fingers resumed slow circles on her slit as he reached up and grabbed and squeezed and kneaded Sofi's perfect cheeks. Then when he leaned forward and ran his tongue along her crack, she plunged her fingers into herself and rolled her eyes into the back of her head. She fingered herself wildly, panting and moaning and gasping, while Jay ravenously worshipped Sofi's ass.

He had never shown as much interest in any part of Eleanor, much less her own butt, as he did with Sofi's delectable derriere.

"Oh fuck. Oh god, Jay. Uhhnnnn." Sofi groaned and whimpered, Jay's lips and tongue kissing, licking, and hungrily nipping at every inch of her fat ass. "I haven't ever... Mmmm... I'm so jealous Eleanor got to experience this for so long."

"I've never done this with her," he said, and Eleanor's back arched into the air, her fingers frigging at her clit. "Your ass is the only one that's ever made me want to do it. It makes my dick ache."

Spinning around, Sofi grabbed Jay's hand and pulled him toward the bed. Getting on all fours, she gazed over her shoulder at him with lust-hazed eyes. "Fuck me. Please, I need it. I've needed it for so long. Fuck me, Jay!"

Grabbing her by her wide hips, Jay shoved his cock into Sofi's wet and waiting cunt. She cried out in delight, only a few inches of his thick cock sinking into her. She was so tight, tighter than Eleanor, and he took his time pumping back and forth, guiding more and more of his dick deeper into her.

She bit her lip and rocked her ass back toward him, taking him inch by inch until his fat prick bottomed out inside of her. His hips met hers and they groaned in ecstasy, savoring the feeling of his cock filling her up. Then he pulled out and slammed forward again, the smack of her ass sending ripples of pleasure rushing through them. Again and again, he rutted into Sofi's wet tunnel, their grunts flooding the room as they fucked each other like sex-starved animals.

"Yes! Yes! I fucking knew it!" Eleanor shrieked, twisting and thrashing on the hotel bed having finally witnessed Jay's cock stuffing Sofi's pussy. It had actually happened. They were actually fucking. Not only that. They were fucking far more passionately and savagely than she and Jay ever had. It was depraved and perverted, made even more decadent by the knowledge that she was right about them all along. That they would make a better coupling, a better pairing.

Jay and Sofi together was a transcendent experience for Eleanor. She knew Sofi was cute but seeing her get fucked put her on a whole new level. A few strands of dark hair hung free from her braid, hazelnut skin glistening with a sheen of sweat, breasts, and nipples swinging wildly, and those ass and thighs quivering seductively with every collision of flesh against flesh.

She could see Jay fucking her harder, him falling further and further into her with every thrust and plunge and it drowned her in a tidal wave of arousal waiting to crash down.

Groans and wails of pleasure filled the two rooms as all three raced toward climactic bliss. Jay's dick pounded into the small girl. Faster and faster he hammered into her, Sofi's moans coming in a staccato rhythm. Her body pitched forward, and she immediately thrust backward, her ass the perfect cushion for their intense fucking. Then he yanked her all the way onto him, her sizeable ass pressing up against him, and unloaded blast after blast of sticky cum into her pussy.

Seconds later, Sofi and Eleanor both came.

-------------------------------------------

Eleanor double-tapped the engagement photo Sofi and Jay shared online.

It'd been eight months since Jay and Sofi first fucked, seven months since Eleanor and Jay broke up for real, and six months since she last saw them. She was admittedly a little surprised that it took Jay a few weeks after having sex with Sofi to actually end things with her but considering how long it took for him to actually embrace his attraction to the sexy dork it wasn't that surprising. But just like with Eleanor's other assertion, he came around in time... with the right nudge.

She remembered when it happened. Sofi had been spending the night at his apartment more and more, and even cheap hotels rack up in price eventually. So, hoping to move things along into that final step with them, she proposed they have sex while watching one of the videos of him and Sofi together. He got as far as getting her naked, letting her take his cock into her mouth, and positioning his dick right against her hole before jerking away and telling her that they needed to talk. Which roughly translated to, "We have to break up."

She had tried not to orgasm from hearing him say it and simply nodded in understanding and got dressed. "I'll pick up the last of my stuff on the weekend."

Eleanor ended up finding a place a couple of miles away, closer to her job, and when she moved out, she disabled all of the hidden cameras inside Jay's bedroom. She had no use for them anymore, having gotten to experience everything she wanted, including spying on them and getting into anal, something that unsurprisingly did not take them very long to do.

Jay never had any interest in trying it with her but by the third time he and Sofi had sex, he couldn't wait to push his dick into her tight passage. Watching his shaft sink into Sofi's perfect posterior, witnessing them both get off to him railing her fat ass, blessed Eleanor with a climax that fully knocked her out.

They were having anal sex more than they were traditional by the time Eleanor disconnected everything.

She smiled at their photo one more time and then closed the app. She wasn't sure if they'd invite her to the wedding, but their engagement didn't bother her at all. Eleanor herself had started dating someone else a few months ago. If anything, it brought her one final piece of closure, confirmation their relationship was going fantastically well.

She sat back in her chair and took a sip of her coffee, her eyes wandering around the breakroom. Suddenly, she noticed something intriguing. Following the stare of her coworker Steve, she caught him eyeing the new twenty-year-old intern, Cindy, who was currently riffling around in the refrigerator. Eleanor grinned.

"Hey, want to hear something interesting," she said to Cindy a little while later at the intern's desk. She lowered her voice to a conspiratorial whisper. "I think Steve might have a crush on you."

"Really?" Cindy peeked her head over to where Steve sat. The svelte redhead was used to attention from guys, especially ones like Steve, those with a little gray in the hair, and a slight paunch in the belly. However, she tended to date men more around her age. "That's nice, but he's not really my type. He's a little older."

Eleanor rolled her eyes. "He has way more energy and enthusiasm than you think. If you got to know him, you'd like him." She cocked her eyebrow suggestively. "...and what he's got to offer."

Cindy glanced Steve's way again. Eleanor was one of the more attractive women in the office. If she found something worthwhile in Steve, maybe there really was more to him than she thought. "You really think so?"

"Oh, yes," Eleanor said, a mischievous smile stretching across her lips. "Trust me. I've got an eye for these things."

Published 
Written by writer4hire69
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