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Hurricane Jessica

By: ShadowyWriter - Published:


Hurricane Jessica


Hurricane Jessica - Sex Story at Shadowy Tales

Chapter 1 - Fake it till you break it 

Adam loved that sound. That loud, sharp smacking sound that his hand makes when it comes in contact with Jessica's soft, flawless skin, as his hand collides with her ass cheeks.


He loved the sight of her tight, slim body, on her belly. Her face on one side, usually the left, with her shoulder length wavy hair, that sometimes she would straighten, when she wanted to give herself a slightly more exotic look.


Adam loved especially the sight of her glistening pussy, constantly wet and ready, as he'd inch his cock past the tight opening, sometimes offering a slight resistance, but ultimately revealing a soft, and remarkably deep and accommodating cradle for Adam's fully erect cock.


Jess wasn't a moaner. She was never awfully loud, but whenever she'd be close to a climax, she would make it known somehow, either by her breathing, or through body language, most often by digging her fingernails into Adam's flesh until it almost bled.

During those moment in which Jess would feel particularly excited, she'd let out barely audible utterances, such as “Fuck! Fuck! Fuck!”, or occasional “oh shit…”, yet nothing too extreme, and never loud.


Strangely enough, Jess never had much sex prior to meeting Adam. The only two men Jess had sex with prior to Adam was a younger guy she had a brief one-time encounter, and her ex husband, and according to her own admission, the latter man was rarely up for the task, to a point where Jessica almost completely gave up on sex for the best, or worst part of 8 years that led to the separation.


As a matter of fact she almost gave up on sex entirely until her first fateful encounter with Adam, in which she climaxed for the first time in years.

At the time Jess’ experience didn't yet delve into masturbation, which made her newfound feeling rather special, but in a different way than most other girls. She loved the feeling, not the man. At least not yet, and especially not in the midst of a complicated separation.


In spite of this attitude of using men for sheer pleasure, Jessica was rather uptight and never cared much for sex talk, in public nor In private. She wasn't much for public displays of affection like kissing or even playful groping, on which she was vehemently against, at least in the beginning.


With that said, once she was comfortably within closed quarters and stripped of her clothing, she'd turn into a monster of passion and lust, the thirst of which seemed unquenchable.


Adam was perfectly aware of Jessica's multiple occasional lovers, and didn't really mind, unlike a number of other men she dated who had a hard time letting her go.


It was never Adam's disinterest in her, in fact it was quite the opposite. He never trusted himself around her, and he had his reasons, rooted in a innate tendency to fall for women who would, sooner or later, take advantage of him and make him miserable.


This was precisely why his relationship with Jess was perfect. Purely sexual, no strings attached, and absolutely no need for pleasantries. As a matter of fact, she'd made it a habit to casually remind him of how much of an asshole he was to her, sometimes during sex.


This extraordinary fluke of a relationship,  was completely foreign to any other man Jessica had on speed dial. Most were quick to wear their “feelings” on a sleeve, while others were simply clingy or jealous due to a combination of factors that made Jessica irresistible. Only a handful were enough put together to be even worth her time.


Standing at a mere five foot and four inches, Jessica’s body was petite but proportioned, weighing in barely 100lb, making her “easy to handle", the latter words taken verbatim from Adam's own, although he always had the feeling he had no exclusive right to the phrase.


Jessica was also the Asian sexual stereotype some men would often fantasize about, with doll-like facial features, deriving from her Filipino heritage, and the most delicate and perfectly manicured hands and feet.


While Jessica's body wasn't the curviest, it was tight, and well proportioned, and looked like the body of a miniature fashion model. Her breasts barely filled a B cup, which completed the picture rather nicely.


The aspect of Jessica that enticed Adam the most, however, was the seeming double life she lead. To friends, family, and her, which she attended regularly, Jessica was morally irreprehensible. To a fault.


Jessica was very vocal about her values and religious beliefs. And the North of her moral compass always converged with God… at least during the day, and when she would be among her more respectable crowd.


This pious image was in stark contrast with the person that Adam, and few others, knew. This was especially true whenever Jessica would happen to demonstrate her prowess in giving oral. In fact, her blowjobs were secretly celebrated as legendary, but not before a long learning period in which Jessica learned to liberate herself sexually, in the wake of her failed marriage.


With that said, Adam didn't get to enjoy the ripe fruit of Jessica's “training”, until Aaron came along, for a brief period while Adam was involved in a romantic relationship and dropped off the grid for several months.


Aaron did not exactly teach Jessica how to properly give head, but rather left her with little choice, as her mouth was the only orifice capable of accommodate Aaron's massive girth, and about half of his 9 inch and half cock, which would often stop short of the very back of her throat, much to her considerable efforts.


The first and last time Aaron and Jessica attempted vaginal intercourse, it was a train wreck. Aaron took as much as 20 minutes to get past Jessica's tight opening, with barely the head of his cock.


With that said, Jessica deemed Aaron worthy of her efforts, as he managed to make her cum in plenty more ways, including his own special blend of oral and fingering skills.


Watching her cum, so hard, and so fast, was a sight to behold. It was almost poetic.


Her entire body would stiffen, while her pelvis would rock, rhythmically, as if there were music playing in her head, until her mouth would open slightly, then wider, until her lips would form a big “O", to which her body would follow as it shuddered violently in orgasmic bliss, while Aaron's skilled tongue and fingers kept her riding her orgasm for minutes at a time.


Ultimately, however, Aaron followed along with the others, buried deep in Jessica's hefty speed dial list, which grew of a few more individuals as a result of one particular night, when Adam, once again freshly single of yet another unsatisfying relationship, lead Jessica to a different kind of climax… one that made Jessica so mad and outraged, she was left with no choice but to retaliate by going on a “fucking spree", that lasted several weeks.


Jessica had a temper, and Adam had a special way of triggering her, which he had used on purpose, as a method of keeping her at a distance. It was never about a mistrust in her, but rather self preservation, from a long streak of bad luck with women in general.


Adam's last relationship drove him to shut himself down deeply, which projected precisely the kind of aloof sex appeal Jessica was fond of, even if he drove her mad, every single time, until one fateful night in which things got… complicated.


It all happened in the midst of summer, when, once again, Jessica showed up unannounced at Adam's doorstep, as she often did during her brief yearly vacation, however this time was overdue, as the last time she saw him, he had sent her right back out the door, after an ugly argument.


His phone flashed several times, as a string of six messages appeared, almost instantaneously, which was one thing that drove Adam crazy. He hated people who send rapid-fire text messages, especially if they are conveying bits and pieces of the same context.


As he walked to the door and opened, however, his attitude subsided. Jessica greeted him, in a blue, tight minidress, and five-inch heels. Her hair was done, and so was her makeup. She looked ready to paint the town red, but something told Adam that neither of them would see the outside of his house for sometime, that night.


“Hey… haven't seen you in awhile.” was all he managed to say.


“Are you gonna let me in, or are you gonna kick me right out again?” she prodded him with a subtle smirk.


Adam nodded, as he opened the door completely and moved out of the way.


Jessica had a carry on bag in tow, but Adam didn't quite feel like being a gentleman, considering the harsh words flung during their last exchange.


“I still have your wine… I can't drink that stuff”, Adam offered, subtly as usual.


“I'll have a glass. I had a pretty stressful day.” Jessica shared, even if she knew Adam wasn't the kind of guy who cares for small talk.


“How have you been?” Jess asked, while Adam poured her wine in a short, round glass he picked from his cupboard.


“I'm fine… same shit.” was his predictable answer. Jess knew him better than most, and she also knew how bad he fared when it would come to relationships.


“What about you?”, he asked, not really expecting a straight answer.


“Same shit.” she parroted, as she took a swig of wine and chuckled briefly.


“That's new…”, Adam noted, referring to Jessica's dress.


“Thanks for noticing. You rarely do. I'm almost impressed.”, Jess replied, almost making an effort not to sound bitchy.


“Yeah, well, something's different about you.”, Adam remarked, as his eyes were unapologetically checking her out.


Jessica sat on one of the bar stools lined up by the kitchen counter, legs crossed, much of her flawless thighs on display, as her right heel tilted left and right, slowly, and her left middle finger drew circles around the rim of her glass already half empty.


“You're noticing a lot of things tonight.”, she whispered as she placed the glass on the counter.


“Yeah… I am. “ Adam approached her, as he did many times before. He walked right up to her.

He was almost surprised as Jessica didn't uncross her legs, with him inches from her, as she used to do, up until two weeks before.


Something had definitely changed, and yet not enough.


Adam's hand was on her right thigh. It took a gentle squeeze to give her a hint, and not long after, her thighs moved, and opened slightly, as both of Adam's hands rested on her knees.


“I'm gonna make you work for it, tonight.”, she said, grinning at his advances.


“Oh yeah?” He responded, as his hands moved upwards and under her dress. “We'll see about that”, he continued, as his fingers tugged the thin, sheer waistband on her lacy underwear.


“Something tells me you're still just as hard to get as the last time we fucked"... he commented as his fingers moved to the front of Jessica's panties, probing her slit with his thumb, as he rubbed her directly over her clitoris with his index finger.


As expected, her body began to respond, and Adam's fingers were soaking badly, dripping with lubrication copiously seeping through her panties, in creamy white globs.


Her hips rocked slightly at Adam's touch, and silence was replaced by the sound of their lips coming into contact, in the passionate kiss that followed.


As expected, Jessica’s hands interlaced behind Adam's back, as her legs did around his waist. Adam lifted her easily, as if she were weightless, carrying her to the bedroom.


Unlike other times, however, Adam broke his routine of turning her face down on his bed and taking her doggystyle right away. This time he kept her on her back as he slipped a condom on his already raging cock, and sank it all, in one go, all the way to her hilt, until his balls collided with the skin directly between the rim of her asshole and the entrance to her pussy.


Two weeks of next to no sex, and rather lousy too, had Jessica on the ropes, as she didn't expect such stamina, which translated into half hour of uninterrupted sex, during which Adam showed no sign of even wanting to cum. He was simply, and unapologetically hard, and the more he'd remember his last argument with Jessica, the rougher he'd get, slamming into her hard, deep and fast on the way in, and slow on the way out.


When he finally got close to coming, he wasn't going to let Jessica have it easy. He knew she liked it best when he'd come inside her. She loved the feeling of his cock swelling further, almost getting locked inside her as he'd shoot his cum inside the condom, filling it up.


Instead, he pulled out… and slipped the condom off of his cock, and climbed on top of her, jacking off right above her face.


She knew what was coming, and shut her eyes tight, as he lined up his cock for the perfect shot.


Adam looked down, grinning, as each single cumshot landed in perfectly straight, white, thick, creamy lines, across her face, and on her dress, while his other hand was busy fingering her pussy still, into her third climax, which cane in perfect timing, offering Adam a sublime view of Jessica's cum covered face contorted into an expression of pure ecstasy, with her mouth gaping open, as droplets of cum moved past the corners of her mouth and inside, while her body concluded in sweet agony.


Jessica spent almost twenty minutes in the bathroom, cleaning herself up. She didn't want to take a shower just yet, but some of Adam's sperm landed in her hair, making it very sticky. When she finally returned, Adam was still laying in bed, naked, with a smirk of satisfaction on his face.


“Did you miss me?”, he almost mocked her.

“You're an asshole… still.”, she began, as she lied in bed next to him, checking her phone.

“So you did?”, he asked her again, this time not realizing it was once too many. Rather unusual by his standards.

“Sounds like you missed me more.”, Jessica responded with a smirk of her own.

“I sure as hell know you missed my cock, judging from your moaning and thrashing earlier.”, Adam prodded her.

“Yeah, sure.”, Jessica replied, rolling her eyes sarcastically.

“I remember when you used to praise my cock, not long ago babe, like it was the biggest you've had.” Adam muttered, as he grew annoyed at Jessica’s compulsive way to check her phone every minute, especially during pillow talk.


“I'd never say you were the biggest, babe.”, she pointed out, grinning slightly, before her smile disappeared. “Babe, I was really mad at you after that fight. You called me names, and I really felt disrespected. You have no idea how mad I was. I literally went on a fucking spree after that. Believe me… you're not the biggest!” Jessica elaborated, matter of factly.


“Wow… talk about being tactful, babe. Not that I ever gave a shit. You can fuck whoever you want.” Adam remarked, somehow more to himself.


“Seriously? You're getting emotional on me babe?” Jessica commented, as she gave Adam a weird glance.


“I'm fine, really. I wasn't being sarcastic.” Adam responded.


“Really?” Jessica prodded him, “So you don't mind?”


“Why would i?” Adam replied, “we aren't in a relationship. Get over yourself!”.

“Ok…” Jessica sounded almost surprised, “Because honestly babe, this one guy in particular almost broke me… he was humongous!”, Jessica shared, unsolicited, and very much on purpose.


“Really? Tell me about it then, I really don't mind, I promise.” Adam replied, lying through his teeth.


“God… you have no idea,” Jessica responded, apparently buying into Adam's seeming nonchalance. “His cock was as wide as my wrist, and took almost twenty minutes to get inside me halfway! If he got in all the way I wouldn't be alive to tell!, seriously babe, I think he stretched me beyond repair!”. Jessica punctuated with no lack of emphases.


*Sounds like a freak of nature. Did you even manage to cum? Was that even possible?” Adam inquired, this time sounding almost genuinely intrigued. “How did it feel?”.


“Gosh I can't even describe it, I literally ended up sucking him off, and that was no walk in the park either. I almost drowned when he finished. After that we agreed there was no way he could fuck my pussy, so we did it in other ways, and he was surprisingly good. He really made up for it.”, Jessica went on, elaborating with perhaps more detail Adam was prepared for.


“Other ways?” Was all Adam could say without making it obvious that he didn't need to hear about it anymore.


“Yeah… he went down on me a few times and made me cum with his fingers. One night I lost count of how many times I came. Must have been a dozen!” Jessica replied, while chuckling briefly.


“So you never came with him inside you?” Adam began prying in a way that was slightly more obvious than he intended.


“Oh babe I never said i hadn't. The first time he fingered me for an hour before trying to enter me with that baseball bat. He prodded me a little bit at a time before getting half way in… barely. But before he did, he felt so good, I came really quick… until he was too much for me to handle… that's when I had to stop him and sucked him. He came quick too, I had to hold my breath, because he had so much in him!”, Jessica elaborated at lengths, once again.


“So, was this guy the biggest?” Adam followed up with his questioning, as he felt his formerly glorious hard on shrink to microscopic size.


“Babe… he was the biggest, but not the best. But I have seen the absolute worst. Right after dating Aaron… this other guy was very nice too, and very good at oral… but my God, he was so tiny! I couldn't even feel him!”, she answered, as Adam started to feel he could relate to the guy Jessica was describing.


“So…. Who is the best so far?” Adam felt he had to ask.


“Babe… you sure are asking a lot of questions! Are you feeling insecure?” Jessica had him open like a book.


“No, I'm just curious hun. Nothing to it, just asking.” Was Adam's feeble attempt as reassuring her that whatever he was feeling wasn't jealousy or insecurity.


“Honestly, there is this guy I'm seeing… he's very nice, and no… his cock is just average size, in case you wanna know.” Jessica replied sarcastically, “I'd have to say you and him are about the same… but he's not as rough as you. You're usually more rough on me than he is.”.


“is that a good thing or a bad thing?”, was Adam inevitable follow up question.


“Honestly babe, if you were a bit more gentle, like him, I wouldn't mind.” was her unexpected reply. Adam wasn't quite sure why he felt her answer was unexpected, but in his mind, suddenly filled with contrasting emotions and ego-fueled imagery, he'd imagined Jessica to prefer a rougher interaction to a gentle one, considering her account of how she enjoyed giving oral attention to Aaron’s oversized manhood.


There was also the matter of Adam suddenly understanding more about himself and the unrealistic narrative he wrote in his head about Jessica. A narrative that was yet to be complete, and already profoundly faulty.


Jessica's appearance of naivete, had obviously triggered a view of her that Adam interpreted as innocence. She barely had any significant sexual experience when he first met her, but Jessica, a woman in her late 30s, was not above experimenting, and she did it extensively, and with gusto, and most importantly, free of any apparent commitment to Adam, or to anyone else.


Right then, in that rare moment of lucidity, uncluttered by everyday worries, Adam was hit by another unexpected epiphany.


“So… I'm too rough? I thought after Aaron, you'd be used to it!” Adam responded half-sarcastically.


“Oh my God, babe! What's wrong with you??” Jessica almost yelled at him, “I told you he was way too big for me to enjoy, I couldn't fuck him like that again, he'd destroy me!”.


“You said you came, babe, I'm just reporting what you said.” Adam insisted, unapologetically, and very well aware of what his tone sounded like.


“Are you serious? Oh my God, Babe! Stop that! What's gotten into you?”, she complained, as Adam was far beyond cornering himself.


“Why are we even having this conversation? We are not even in a serious relationship! What do you care about the size of other guys fucking me?”.


Adam's face needed no words. He painted the whole picture. Suddenly Jessica knew what was going on… or at least part of it.


“Ok, so… “ Adam began, almost whispering, “... I guess you're right, and… I'm sorry for steering the conversation to a place I didn't want to take you to. But…”, a pause ensued, followed by  Adam exhaling, “... I haven't been able to stop thinking about our last fight, and I think that I started that fight, because I'm starting to feel vulnerable around you.”


“What are you saying?” Jessica responded, with a hint of concern in her voice.


“What I'm saying is that, I've recently realized that I'd like to explore the possibility of being exclusive.”, Adam finally dropped the E-bomb, as he could almost hear a drum roll in his head.


“Well…”, Jessica began, “... honestly I kinda like things the way we are, but I have a feeling it's no longer an option with you, is it?”


Adam nodded, as he felt he already got the answer he was looking for.


“It's an option… still.”, Adam forced out of himself, “...of course my feelings are different, but I'm not going to force you into a relationship you don't want. If rather keep things the way they are than losing you…”.


There was a long pause, but most of what needed to be said, had been already.


“Are you sure? Are you ok with us just being friends?”, Jessica checked, as Adam felt he was already halfway into the friend zone.


“Yeah… I'll be alright.”, Adam responded, amazed as his own composure. “I got… work tomorrow. I'm gonna need to go to sleep soon.”, he announced almost whispering.


“So you're gonna kick me out again?” Jessica reprimanded him, only to crack a smile and a brief chuckle, “Hey, I'm kidding babe… let me just gather my things, I'll let you go to bed.”


Just as Adam was ready to see Jessica out, she turned around, looking at him with an almost nostalgic look “Hey… listen, we got a good thing going on. I wanna keep that ok?”, she began, “I Don't want us to be weird, or anything. I want to be able to still talk to you about everything. I need to know we can still do that… like if I tell you about a guy a slept with, without you acting weird. I'm just hoping…”, Adam interrupted her right then.


“We are going to be fine. I'll be fine. Nothing has changed, ok?”, was Adam's last lie for the evening.


Chapter 2 - Welcome to the Friend Zone


In the weeks that followed, Adam noticed a shift in his relationship with Jessica. In spite of all that was said and done, an initial rift began to spread between them, however, while it would be a fair assumption that Jessica would be the one drawing a wedge, the reality was that Adam simply felt increasingly uneasy around his former fuck-buddy, a status that had evolved into that of a friend-confidant, with a lingering sexual innuendo. Not the kind that leads to sex, mind you, rather the kind of meaningless banter that serves the purpose of maintaining the appearance of continuity throughout a profound change. Sadly enough, Adam was now confined to a Friend Zone of his own making. An ice-prison designed to protect his ego, under the guise of unrequited love.


In layman's terms, a monumental, self-inflicted mind-fuck.


There were attempts to rekindle some sort of spark, however they were forceful, awkward, and no longer in character with the type of organic relationship that used to exist between the two of them.


Those attempts stopped completely, on a fateful Saturday night, when Jessica showed up at Adam's doorstep, unannounced as usual.


As welcomed as Jessica's visit felt, Adam was now in a completely unfamiliar territory, as if he felt Jessica were a different person, someone he had to get to know again, from scratch. He simply could not recognize her.


As usual, he poured her a glass of red, and they both sat by the bar's countertop. Only a few weeks prior, Adam would have been all over her, aggressively pursuing her, knowing she wanted it as much as he did.


That night, Jessica wasn't anywhere near as put together as she used to be. Her magnificent legs were clad in faded denims, and shallow heeled leather boots, and a hooded sweater concealed much of her upper body. Her hair was shorter, and quickly tied in a ponytail. A pair of simple gold-colored earrings dangled from her earlobes.


“Haven't seen you for a while, how have you been?”, Adam initiates the small talk routine, he himself always dreaded with a passion.


“I'm doing ok, I've been dating a bit, the same people so far... keeping busy… life is good so far.” was Jessica's response.


“That's cool… I'm glad you're doing good. I haven't dated as much, really… I'm way too busy with work right now.” Adam lied, in a way that made sense only to him.


Jessica was being a real trooper, making an effort to cut the tension, but she also knew to stand her ground, as she knew that Adam was going through something beyond what she could comprehend, and she wasn't going to let it affect her.


“So, let me ask you something… since I know you're kind of an expert…” Jessica prompted out of the blue, emerging from a silence that was quickly becoming deafening,


“... I've been seeing that guy I told you about… the average guy. He's very sweet, and he doesn't even touch me unless I give him permission. Am I being too bossy?”


It took almost ten full seconds for Adam to come up with an answer, but eventually his guts held up, “Well… the fact that you're bossy is not news…”, Adam said as he shrugged, internally complimenting himself for a perfectly generic answer to one of the many questions and topics he knew had to endure.


“Oh my God you're still such an asshole!” Jessica piped up, as she took another swig of her wine. “Anyway… before you give me your actual opinion… here's the full story: Aaron just got back from Florida, and he texted me. You remember him, right?”.


Adam remembered all about him. His mad oral skills, and especially his monster-sized cock. “Yeah… of course. So you're… seeing him again?”.


“I don't know… he's very nice, and I guess it might just take a bit of practice to get used to his… size… but I'm kind of conflicted because I know myself, I'm a little controlling, and Aaron is… kind of like me.”. By the time Jessica was done rambling, Adam felt he was two minutes from hurling everything he ate during the day.


“Ok, so… I don't understand what you're asking me. Are you asking me which one you should… fuck?... date? I don't get it.” Adam was visibly struggling, although his composure was remarkable.


“I guess… dating? I really like them both, and honestly… I even bought something to practice if I ever decide to go with Aaron… wanna see?” before Adam could say Hell no, Jessica already had her hands buried in her handbag, as she drew out a black pouch, the size of a large flashlight.

Little did Adam knew, Jessica unveiled the largest, longest rubber dildo he's ever seen up close. It was flesh coloured, and textured with nearly realistic veins and nerves to resemble the real thing. Adam could only assumed, that monstrosity was as closely resemblant to Aaron's manhood as it could possibly get.


“This is barely an inch bigger, can you believe that? Oh my God!! I can't believe he managed to get half of it in me the first time!” Jessica was almost cheering, as Adam's vision began to fade slightly.


Finally, as Adam managed to put in a titanic effort required to snap out of his trance, he was able to speak again, “That… is… impressive.”


“I know, that's crazy… I can't believe it took me less than a week to get used to this size! I must be a freak too I guess!”, Jessica bursted in a hysterical laughter, as Adam forced himself to smile.


“Anyway babe… I really hope you don't feel weird still about us, and you look great!”, Jessica cheered as she emptied her glass and jumped on her feet, ready to head out, “I gotta go, but I'll text you, ok? Don't be a stranger!”. Adam could see that she was in a hurry. In his mind, he had a hunch of where, or whom she was going to, and hated himself for not being able to simply tell her that none of that was going to work for him. He knew he had to cut ties. He just didn't know how.


Chapter 3 - The Ambush


The days that followed proved particularly tasking for Adam, as he struggled to come to term with what happened between him and Jessica. In his eyes, she was a completely different person, but in reality, she never changed. Adam did, profoundly. That sense of denial that pervaded his brain, was overwhelming, powerful, and impossible to shake off. Adam fed off of it, as he sank himself deeper into a depression that lead him to arbitrarily stop responding to Jessica’s attempts to reach out, including her impromptu visits, which he’d deal with by simply keeping all the lights off in the evening, and his car in the garage, to appear as if he weren’t home.

Three weeks of this madness caught up to him, eventually, as Jessica became aware of the pattern taking place.


At seven o’clock, on a Monday night, a thread of messages appeared on Adam’s phone. Jessica had it with Adam’s breakdown in communications. It was time to face the music.


“ - We need to talk.”

“ - Why don’t you answer your phone???”

“ - WTF”

“ - Adam, get back to me.”

“ - You’re an asshole… call me!!!”


The messages just kept on coming, until she finally stopped.


There was no doubt in Adam's mind that he was doing the right thing. Unrequited feelings were never his strong suit, with a lifetime of experiences to prove him right.


It wasn't until several weeks later that Adam realized how deafening silence could really be.


No more messages, no calls, no more unannounced visits. He finally got what he wanted, and he wouldn't have wanted it any other way. Like a bandaid, Adam ripped Jessica off his life, or so he thought.


On a drizzly Tuesday night, Adam exited the building where he worked, only to find Jessica, arms crossed, leaning on her car's driver door, donning a pair of dark sunglasses.

She didn't look pissed, but she looked like she meant business, whichever that was going to be.


“I know you!” she shouted at Adam's sight, as he walked towards her with a guilty look on his face.

“Hey, haven't seen you in awhile”, Adam commented with a grin.


“Yeah, bullshit. You owe me an explanation, buddy.”, Jessica cut him off, walking in front of him, as if she were about to beat him up and take his lunch money.


“I guess I do… “, Adam replied, almost whispering.

“Start talking then, and make it believable. I wanna know why my best friend has been avoiding me for the past three weeks, without a shred of explanation.”. Jessica commanded him, in no uncertain way, which pushed Adam into a corner from which there was only one way out.


“Jessica, I don't think I can be friends with you anymore.”, he dropped the bomb, matter-of-factly. He was surprised at himself for the organic way it came out. It felt as if he had rehearsed it for days.


“Ok… wow… “ Jessica’s expression changed to somewhere between intense pain and surprise. “... ok… so.... that night when I asked you if we were fine, you lied to me.”, Jessica prompted him.


“Yeah, I did.” Adam replied without flinching, “I really don't know what you want me to say. I told you that i fell in love with you, and you showed up at my house asking for advice about having a relationship with a walking dick.”, Adam looked at her as if he felt nothing, and for the first time, Jess looked like she could feel that too, then he shrugged, shaking his head, as if he were waiting for a smartass comeback, or some similar type of response.


“Hey…” Jessica replied, “... I'm sorry I hurt your feelings. I may not feel the same about you as you do for me… but i also feel like I'm not ready to lose you as a friend… and the second best lay I've ever had!” she punctuated, with a hint of misdirected humour.


At that, Adam began walking past her, as he took her last remark as his cue that that conversation needed to end.


As he approached his car, he could hear Jessica's heels clicking on the pavement, behind him, “Why can't we be like before?”, she pleaded, as Adam unlocked his car and opened the door.

Just before he got in, Adam paused for a second, then turned towards Jessica.


“I have never realized it up until a month ago, Jess… I actually never wanted to be like we were before.”, was the last thing he said before getting in his car and driving away.


Chapter 4 - Intervention


“Oh fuck…!!”


It seemed odd to Jessica, for Adam to come to mind, right then, as Aaron’s manhood stretched her within a quarter inch of her physical limitations, with his ball-shaped purple head pushing against her uterine wall, while her throat was being gently squeezed, and her hair grasped, and used as leverage.


“Oh shit….!!”


Well into her second week of seeing Aaron on a regular basis, the size of his cock remained the stuff of legends, but that wasn’t what kept her on her back… and sometimes on her face. It was that unique combination of an almost painful, extreme penetration, and Aaron’s expert manipulation of Jessica, as she endured her daily dose of horse-sized meat. As often unbearably painful as it was, in that first first few minutes it took Aaron's cock to squeeze past Jessica's very entrance into her love canal, the slow, careful attention with every inch gained, made it worth it, as long as he did as promised, and never push to the very hilt of her. A promise he broke only a few times, with mild repercussions.


“Fuck yes!!”


His way of smacking her ass, gently, but firmly, and repetitively, as he skillfully timed each stroke into her outstretched pussy, with each hard, well assessed smack on her cheeks, played no small role.


“Oh shit… give it to me, babe….”


The way he would almost choke her neck, gently cutting her airways, in that way that can only be done under an ironclad contract of mutual trust.


“Oh God…”


The way he’d kiss her and tease her. The way he’d rub her clitoris, light and fast, while inside her, in a way that would almost make her forget his size, in favor of intense preorgasmic bursts.




And of course, her personal favorite, was when he’d keep just the head of his cock, barely inside her, yet still stretching her entrance, as he’d push in and out slow, making Jessica feel as if she were being almost fisted.


She knew very well that in normal circumstances, if Aaron had no clue how to touch her, his enormous cock would be just about as useful as a paper condom.


She’d come hard, and she’d come loud. Her entire body shuddering, as Aaron would withdraw his cock, leaving Jessica’s pussy gaping for a few minutes before her labia would close again.


If only he’d get tired like the majority of the men she fucked, Aaron would be the perfect sexual partner. Sadly, his habit to wake up at odd hours of the night for yet another pussy-stretching session, drove Jessica insane, and turned her into a walking corpse in the morning.


“Ok, knock it off… stop it! I’m fucking exhausted! Get off of me…”, Jessica barked at Aaron, as her face was half-buried in her pillow, and her ass up in the air, while Aaron’s hands were grabbing onto her hips, and forced them to slam Jessica’s overworked pussy onto his fully erected cock.


As soon as Aaron let go of her, Jessica turned on her back, with a pensive look on her face.


“What's with you?” Aaron queried her, as he was now left fighting a full scale erection by himself.


“Just this friend I have, he's acting like an idiot.” was Jessica's response, as Aaron laid next to her, with his raging cock strategically positioned within Jessica's reach.


“What did he do?”, Aaron asked. A coy smile drew on his face as Jessica's hand moved on his lap and began instinctively running her fingertips along the back of his shaft.


“Fuck… why are you so hard all the times?”, Jessica dodged the question as she began stroking him more vigorously. Then her hand stopped momentarily, only to resume at a slower pace. “He told me he wanted a relationship. I told him about you, and now he won't talk to me.”.


“How long have you been friends?” Aaron asked, with a more serious tone.


“A few years, he was great in bed, and was funny. He was a bit of an asshole, kinda like you.” Jessica answered as she shifted position to drop her head down to Aaron's lap.


“But you don't have feelings for him?”, Aaron asked, as his eyes tracked Jessica's mouth closing in on the head of his cock.


“God, babe, would I be doing this if I wanted to be with him?”, Jessica replied as her mouth engulfed a few inches of Aaron's cock, as her hand began to stroke it.


Aaron's hand moved between Jessica's legs, and his middle and ring fingers quickly found the warm, wet, soft, and still very loose slit he had been giving a relentless workout.


The one thing she initially loathed upon learning it with Adam, oral sex, somewhat became a welcome routine with Aaron, as it was the one activity able to keep the attention off her pussy. She was never particularly good at it, but her skills matured quickly, as the need grew, into what Aaron often referred her as “star cocksucker”. A well deserved title, for skills that earned her praises from the selected few, lucky enough to enjoy Jessica’s special handling, and who rewarded her in ounces of abundant, and often projectile, jizz.


Jessica still hated hearing her own slurping sounds, as her tongue swirled around Aaron’s cock, and her lips opening progressively as she took the head in, giving it a tight squeeze with her lips, slowly downwards, followed by a quick up-down motion that lasted a few seconds, before she’d go down further, to give him a proper sucking.


That night it took her a little longer to finish him off, as she was somewhat distracted by her own thoughts, until her weekly fill of Aaron’s cum, shot down her throat, as she struggled to swallow it all. At least that night she was lucky he wasn’t in the mood to grab her hair and brutally fuck her face, as he used to do most often.


Like a good little trooper, Jessica swallowed it all, and as always, she stuck her tongue out and opened her mouth wide to show Aaron what a good job she did.


“You're amazing. Your friend taught you well!”, Aaron commented as he came down from his orgasm, between breaths.


“Actually I hated giving heads, it's the only way to keep that big fucker of yours from destroying me down there.”, Jessica replied, laughing.


“Well, he must have done something right, for you to obsess about him during sex.” Aaron commented, as Jessica dragged herself out of bed and into the bathroom.


“I'm not obsessing! I'm just pissed at him. We have been close friends for years and now he's decided to ruin it.” Jessica could be heard complaining as she opened the bottle of mouthwash.


She gargled the blue liquid briefly but thoroughly, and spat it into the sink, then walked back into the bedroom, in all her glory, with that catwalk-like slow strut she does when she looks good and she knows it.


“Maybe I should meet the guy.” Aaron said out of the blue.


“Are you serious? Why would you want to do that?”, Jessica uttered in surprise, “That's like… the worst idea ever.”.


“Think about it. Your friend is obviously being insecure, and if we all get together and he actually meets me and gets to know me, he might change his mind and you two might reconcile.” Aaron explained, and strangely enough, Jessica paused for a minute to think about the mere notion of that proposition.


“You may be right… as crazy as it sounds.”, Jessica muttered.


“So, call him up. See what happens.”, Aaron prompted her, as he handed her phone.


Jessica hesitated for a long instant before dialing, but eventually her thumb came down.


Six rings later, Adam picked up the call: “Hey Jess, what's up?”.


“Hey stranger, what are you up to?”, Jessica replied, still uncertain about how she'd approach him with Aaron's proposition.


“Nothing much, what's going on?” Adam responded, with a sleepy tone.


“I'm wondering if you'd like to hang sometime this week…” Jessica replied, as she began feeling a little anxious.


Meanwhile, Aaron shifted his body to lean on his side, closing in on Jessica who was also leaning in the same direction.

Aaron's semi-hard member suddenly wedged between Jessica's thighs, almost made her jump.


“Yeah… ok. I'm kinda free Thursday night if that works.” Adam suggested, as Jessica struggled to keep calm with Aaron dry-humping her from behind.


“Wanna come over at around eight?”, Jessica asked, fully aware that Aaron's thick, fully erected cock head was now poking through her very wet slit.


“Sure.”, was Adam's dry response.


“Great! See you then.”, Jessica replied, trying to wiggle away from Aaron.


“Alright, bye.” Adam ended the call, after a short pause.


“Done, happy?”, Jessica scuffed Aaron, as he seemed undeterred in his pursuit of Jessica's still glistening pussy.


“I'm very happy right now…”, Aaron replied with a grin on his face.


“Alright now wipe that smirk off your face and fuck me already.” Jessica commanded him, as she laid flat on her stomach, her legs spread, and ass propped upwards, while her hands were grasping one of the black metal frames of the bedpost,  as she braced herself for another epic pussy stretching session. “And be fucking gentle this time!”.


For two days solid, Adam questioned his agreement to show up at Jessica’s. He knew he wasn’t ready, and the last thing he wanted to do was to be confronted with something he didn’t need, nor had the resources to handle.


Thursday night nearly snuck up on him as he hurried to get home from work, and get ready. Adam’s head was overwhelmed with thoughts and questions, on whether she just wanted to reconcile as friends, or she was going to give him the closure he needed, one way or the other.


As he pulled into Jessica’s driveway, Adam noticed a different car parked in Jessica’s spot. He sent her a quick text to let her know he arrived.


“Come on up!”, Jessica replied within a minute. At that, Adam climbed the short flight of stairs leading to the second floor apartments. The door was already open, and bright light from the living room overhead of Jessica’s small apartment, illuminated the external handrail.


Jessica’s voice could be heard from inside, chuckling. At that point Adam had a clue that somebody else was in the apartment with her. His suspicion was right on the money, and his heart sank, as he saw a rather tall man, with short blond hair, standing in the living room, holding a beer.


“Babe! Come in!” Jessica squealed, as she saw Adam standing by the front door.

Adam counted each step as he walked in, feeling as if he were being ambushed. “Hey… what’s up?”, he said, as Jessica wrapped her arms around his neck and hugged him, pushing her firm, round, and perfect tits against his chest, for the first time in almost a month.


As soon as she broke the embrace, Jessica turned to the hunk standing behind her, “This is Aaron, he was in town and when i told him you were coming, he asked if it was ok to meet your acquaintance!”. She made a serious effort to make her story sound believable, but as far as Adam was concerned, the cat was out of the bag.


“Ok…”, Adam muttered, trying his best to be civil, while hoping for a short ordeal, as he planned his hasty retreat.


“Nice meeting you, Adam, i heard a lot about you!”, Aaron extended his hand towards him. Adam decided not to hesitate more than necessary and shook it firmly but briefly, in a similar fashion as two rival businessmen when they are about to sign a contract.


“Thanks… same here”, Adam said, as he tried not to sound sarcastic.


“How about a beer?” Aaron offered.


“Thanks…” Adam accepted, dryily.


“I hope you are hungry, i ordered pizza!” Jessica chimed, as she moved to the kitchen, “Come on, everyone grab a slice and let’s hang out in the back!” she prompted, as Aaron and Adam both glanced at her glorious ass on its way to the small outdoor terrace.


Adam knew that terrace very well, as it was the place where they fucked the very first time. The small space was completely walled off to the sides, and with a four-foot balcony concrete rail, with six slots, too narrow to draw the attention of onlookers. It was also the place where Jessica first attempted to give him oral, and ended up hating it for the remainder of their first few months of relationship as friends with benefits.


Adam and Aaron sat on opposite sides of the outdoor structure. Jessica sat right next to Aaron, on a bar stool, while Aaron and Adam sat on white plastic lawn chairs.


“Jessica says you are a manager at an insurance company?”, Aaron asked, trying to break the ice.

“I’m an auditor, “ Adam answered promptly, “I review case files, and determine if claims should be approved…”.


“I guess i should be real nice to you, next time i rear-end someone!”, was Aaron’s awkward attempt at a joke. Luckily Adam decided to pick up on the perceived jest, and chuckle briefly.


“I don’t know much about you, what do you do?”, Adam decided to finally hold his end of the conversation.


“I’m a tennis coach, in Kissimmee, Florida, but i have a property out here, that i use during the winter.”, Aaron explained, before taking a sip of his beer.


“Cool…” Adam replied, as he gulped down the remaining half of his beer, “I should probably get going, i still have work tomorrow.” he then announced out of the blue.


“Seriously?”, was Jessica’s response, “Come on, babe! I never see you anymore! What the fuck!”.


“I know… i wish i could stay longer, Jess…” was Adam’s reply, as he got up from his seat, trying to keep himself from lashing out externally as he was already, inside.


Adam finally had a visual of what Aaron looked like. In his mind he could very well imagine him, in all his terrifying, emasculating glory, pounding on Jessica in all sorts of positions, for hours. He even wondered whether she could even feel him inside her, after being stretched by that monster.


“I guess i’ll keep in touch…” Adam said as he nodded towards Aaron, while Jessica looked at him with a disappointed expression in her eyes.


“Alright babe, let me walk you out…” Jessica offered, as Adam was already halfway to the front door.


Jessica followed Adam downstairs where his car was parked, while Aaron was out on the walkway, leaning over the exterior railing atop the stairs.


Adam had his car keys in his hand, but it took him a minute to push the button and unlock the car, with Jessica right behind him. He turned around, as he felt her hand on his shoulder.


“What the Hell was that?”, Adam finally asked her, almost whispering.


Jessica had no immediate response to that. She just stood there, frowning.


“You know what… i don’t care. Just do me a favor and leave me alone.” was Adam’s last words before he finally unlocked his car.


“Wait… “ Jessica tried to stop him, but he was already inside the car, with the key in the ignition.


“What is it now?”, Adam asked, trying not to look at her.


“I’ve missed you… “, Jessica brought herself to say, as she began tearing up, “Why can’t we be like before?”.


At that. Adam shut the door and turned the engine over.


As he pulled out and into the street, he kept saying to himself “Crazy bitch…”, trying to rationalize Jessica’s plea, as some kind of ruse to humiliate him. He wanted to believe, so badly, that Jessica was simply an evil, malevolent succubus, bent on using him as a tool for her sick games.


The problem was that, deep down, he knew it was just a fantasy. The reality was far more terrifying.


Chapter 3 - The Bigger Man


In the two weeks that followed that awkward evening at Jessica’s, Adam began to gradually accept the reality of his situation. Jessica didn’t want a relationship. She never wanted one, and if Adam wanted to have any kind of relationship with Jessica, he had to learn to share her with other men. It was the only possible solution to preserve a friendship on the brink of permanent damage.


One of his coping methods was often to spend hours at a time, carefully searching for pornography featuring women resemblant of Jessica, engaged in rough sex, with men as endowed as he imagined Aaron was.

Initially it was a painful task, but after a while, it turned into the only way Adam could become aroused, and even bring himself to climaxing.


Well into the second week, Adam was so entrenched into his nightly, and sometimes morning, routine, that he had almost forgotten what it actually felt like to have sex with Jessica… the real Jessica. In his mind, she was forever ruined, and that’s when he realized the horrifying truth of his condition.


Saturday came, and Jessica’s phone rang. To her disbelief, Adam called her.

It took her a minute to press the green button. “Adam…? How are you?”, she finally answered.


“I’m fine… “ Adam’s voice had a different tone than before. He sounded apologetic, almost meek. “... listen, i wanted to say sorry for the way i dashed out last time. It was lame, i know… and you have every right to be angry at me.”.


Jessica cut him off quickly, and took him by storm with four words: “I want you now.”.


Adam had no response to that, except am awkward “Ok…”.


“I had enough of this bullshit game, Adam. If you care about our friendship, you’ll come by tonight and fuck me. Tonight.”, Jessica demanded, in no uncertain terms, before hanging up.


One hour later, Adam sat in his car, outside of Jessica’s apartment building. Unable to move, as he simply stared at his steering wheel, until his phone lit up with a text message.


“Come.” was Jessica’s brief text.


When Adam reached her front door, he knocked three times, until he realized the door was already open.

He walked in, only to find Jessica, sitting on her couch, wearing a lacy black dress, and matching heels.

Her hair was down, and straightened. Eyeliner accentuated her eyes, and red lipstick gave her a vaguely vampiric look. There was no doubt in his mind, that she wanted to be fucked, especially on account of her staring at him the way she did many times before, each time she wanted him.


“Shut the door.”, Jessica ordered him. He complied instantly, like a good little soldier. “Come here.”, she then followed in the same commanding tone.


Adam walked up to her. He looked at her, but for the life of him, he just couldn’t feel aroused. He was almost in shock at the fact that nothing moved, not even a little.

Jessica looked hotter than he’s ever seen her, and yet, he was frozen, stumped, utterly impotent.


She looked at him, and she knew something was broken, damaged… perhaps beyond repair.

When he finally uttered his first words, he sounded weak, almost depressed. “Where is he?”.

Jessica shook her head, with a disappointed look on her face.


“I don’t know. I saw him last week. I don’t really care.”, Jessica replied. Somehow Adam didn’t believe her.


“I know you don’t. That’s why i don’t even know why i am here.”, Adam responded, as his tone acquired a roughness to it that Jessica couldn’t place. He wasn’t the asshole she knew. He was something entirely different. Something she wasn’t sure she wanted to find out.


“You are here because i still care about our friendship, and because you need to snap out of this little bitch act of yours.”, Jessica reprimanded him, “I turned you down, and that was my prerogative. I never meant for you to turn into this...thing you are now.”.


“What thing?”, Adam asked, immediately rebuked by Jessica’s commanding tone.


“You were an asshole, and you treated me like the bitch i am. No compromises. You wanted me, and you took me. I miss that. It turned me on. What the fuck happened to that, Adam?”, Jessica thundered, leaving Adam almost breathless.


“I don’t know… i don’t know why i feel this way.” Adam tried to explain, “I don’t know why… but the thought of you having sex with Aaron has bothered me… more than i ever thought it would.”


“Why?” Jessica barked back, “Is it because he’s hung like a horse? Is that it?”


“Yes… i guess that’s it. I know i’ll never do it for you anymore… after him.”, Adam almost whispered.


“You’re a fucking idiot, Adam. Like all men, you don’t know shit, and you buy into your macho bullshit like a frat boy! Grow the fuck up, will you??” Jessica shouted at him, uncaring of whoever listened that late at night. “Do you even know how a vagina works?”.


“You showed me the size of that dildo, Jess. How doesn’t something like that stretch you permanently after getting it on a regular basis?”, Adam whined, shaking his head.


“How? Are you fucking serious?”, Jessica looked at him as if he were from another planet, “You know my sister, right? The one in Georgia, who had triplets last year, right?”, Jessica suddenly brought up.


Adam nodded, and shrugged, while Jessica glared at him in silence, with her mouth semi-opened, almost waiting for him to have some kind of epiphany.


“Holy fucking Christ, Adam! Three babies passed through her vagina! Three! What do you think she looks like now, you fucking moron?? By your logic, she must have a uterus the size of a bowling ball!”, Jessica punctuated, as she stared at Adam, wide-eyed.


Adam’s lips pursed for a moment, as he looked towards the window. He let out a nervous chuckle that turned into a painful frown.


“I get it… you felt insecure, and maybe you let your imagination run wild for a while. I also know you were hurt by the fact that i don’t want a relationship… and God knows what else you misread about me. This doesn’t change the fact that you got it all wrong, and that you need to get over your shit, and come back to reality…” Jessica continued, “... i want you back, Adam. I want you to fuck me like before.”.


“What about…”, Adam was about to say that name again.


“Aaron? What about Aaron?” Jessica cut him off again, “That depends on you, Adam. You can continue being an insecure little bitch, and lose me forever, or you can start being a man again, and fuck me like you mean it. It’s all on you.”, Jessica deliberated, as Adam nodded, looking at the floor.


When Adam finally raised his face to look at Jessica, her stare was ice-cold. She sat with her legs crossed and her arms outstretched atop the backrest of the sofa, in a power stance. She looked menacing and defiant, but most importantly, she knew what she wanted.


Then, her right knee raised from being atop her left one, and her foot quickly dropped to the floor, as her thighs spread, revealing her bare pussy underneath the short hem of her dress.


“Undress, and make it quick. I need your face between my legs, now.”, Jessica’s authoritarian tone prompted Adam to instinctively unbutton his shirt, and remove each piece of clothing he had on, until he was completely naked, standing before her.


“I said now, Adam.” Jessica reiterated.


Adam motioned towards her. His cock was still completely flaccid, as he knelt between her legs, and began darting his tongue across her slit, while fingering her. If there was anything Adam mastered, was how to go down on a woman, especially Jessica.

He knew her pussy so well, he could sculpt a perfect replica out of clay, by heart.


He knew where to hit her, where to stroke her, and where to lick her. He made her pussy his undisputed oral domain, ever since she let him know she would no longer indulge him.


Still, for the life of her, Jessica couldn’t understand how was he not hard as a rock, like he used to be. It couldn’t have been her. “What’s wrong babe?”, Jessica whispered, as Adam worked her clitoris to arousal, “You’re usually hard by now… like… way hard, babe.”.


At that, Adam stopped, much to Jessica’s disappointment, as she was already soaking wet.


“I’m sorry… i can’t do this. I have to go.”, Adam announced out of the blue, as he hurriedly got dressed.


As she adjusted her dress back down, Jessica strode right behind Adam as he almost ran back to his car. She gripped his arm, shouting “Stop!”.


She wasn't going to have it like this anymore.


“I get it... “, she began, as she watched Adam come to a halt, “... you love me, and you're jealous of Aaron.”.


“So what?”, Adam replied, “... you don't feel anything for me but sexual lust, and now you have another toy to play with. Go play and leave me alone.”.


“Adam… “, Jessica responded, still holding his arm, “it's not that I don't love you. I just don't love you the way you wish I did. I can't have a family… my life is too complicated!”.


Right then, Adam's eyes turned colder, almost dead as Jessica couldn't have been any more ill-prepared for what came next.


“Then let me go. I did and it worked out fine.”, Adam simply asserted, without a single hint of emotion in his voice.


Chapter 4: Deal or No Deal


“He’s clearly manipulating you.” Aaron pointed out as he couldn’t take anymore of Jessica’s dramatic monologue. She had been going on for an hour about her conflicting emotions in regard to Adam, and the what-ifs of their last interactions. All of it, only a few short minutes after guzzling Aaron’s load, with barely enough time to wipe the excess jizz running from one corner of her mouth.


“Do you think so? Or is it your way to keep me for yourself?” Jessica fired back, and with conviction. She may have discovered herself as a new, perhaps overly-sexual being, compared to her near-sexless older self, but she wasn’t a horndog. She was confident in experimenting and liberating herself, but Aaron’s tone struck a note in her. She knew what he meant, and she knew Aaron liked to have that kind of hold on people, not just sexually. It was a power trip.


“You need to get out of my apartment. I need to think.” Jessica ordered him, as she grabbed a robe from her dresser, and hurriedly threw it on herself.


“Alright, your house, your rules.” Aaron agreed, and began collecting his clothes, and get dressed.


“Let me know when you’re feeling better.” Aaron muttered on his way out.


Judging by the strength of Jessica’s door slam, Aaron had a hint it was going to be a while.


Jessica didn’t mind the cold, only the humidity. The winter holidays were the worst, just before the frigid cold of January. It was constantly foggy and damp.

She took a long, hot shower before deciding what to wear. She wanted to look ravishing, but she wasn’t about to freeze her ass off.


Thigh-high, black thick wool-top stockings seemed appropriate, under a knee-length long-sleeve winter dress. Leather boots were the obvious choice, on a five-inch biker heel.

A black trench coat completed the picture, along with a hint of tasteful makeup.


There was not a doubt in the world that Jessica was on a mission.


She raced through traffic, always heavy around the holidays. It took her thirty minutes to reach her exit, five more minutes to see Adam’s driveway, empty.


She pulled over and at a glance, Adam’s place was dark and deserted. Most of the neighborhood was quiet.


Right then, Adam’s car pulled into the driveway. Adam recognized Jessica right away, nodding briefly as he got out of the car.


“Hey.” Jessica greeted him.


“You look nice.” Adam responded, as he fished for the front door key.


“Thanks… can i come in for a minute?”, Jessica pleaded, as the cool air was making its way up her skirt.


“Yeah… sure.” Adam swung open the door, following her into the house. “Can i get you anything?” he offered. Jessica shook her head, and pulled up a bar stool.


“Wanna tell me what’s this all about?”, Adam asked, while taking off his coat, and throwing it on the couch.


“I have a proposition…”, Jessica began, “... and this is really the best compromise i can come down to.”


“I’m listening.”, Adam replied, nodding briefly.


“I’m willing to be exclusive… but i have one condition, and it’s not negotiable.”, Jessica continued.


“Which is…?” Adam asked, almost afraid of what would come next.


“Once a week, we will go out on an open date.” was Jessica’s cryptic reply.


“What is an open date, exactly?”, Adam grew worried.


“We will go out together, as a couple. We will engage in social interaction with other people, men and women. We will flirt, and there will be sexual innuendo. In the event that one of us finds a particular sexual chemistry and compatibility with someone, we agree to let you or i have sex with that person, under reciprocal supervision.” Jessica elaborated, in no uncertain terms.


“So… in essence you want me to watch you have sex with other guys.” Adam’s response was just as matter-of-factly.


“Babe… the odds are 50-50 here. I have no doubt you have the ability to be just as flirtatious as i can be, and let’s face it: you are a good looking guy!” Jessica prompted Adam’s ego,


“This is ridiculous… how’s that different from being a cuckold?”, Adam complained, as Jessica could feel he wasn’t going to buy into her proposal.


“For starters, “Jessica responded, “... you would not be a cuckold at all, as you’d be free to join me if you want.”


“Would i be free to leave too?”, Adam inquired, half-sarcastically.


“No, babe, i want you to be part of this. That’s the deal.” Jessica responded, without a hint of hesitation.


“I can’t believe i’m even considering this…” Adam caught himself saying aloud.


“You haven’t heard about the best part, babe…” Jessica added, with a grin, “At the beginning of each date, you get to pick one thing that i am not allowed to do with the person i get to go with, and vice-versa. It can be anything we want. Anything at all. That one thing will be our deal-breaker.”


“Like what?” Adam asked, obviously intrigued.


“Anything…” Jessica elaborated, “... Anal, for example, or kissing, or blow jobs. Anything we want. That one thing will be off the table for the night, with that one person.”


“I see… “ Adam reacted, as his face still gave away suspicion on how such proposition would be acceptable by his standards. “... how’s that supposed to make me feel better about fucking another guy in front of me?”


“Babe… that’s because only you get to do that with me, on that night, and vice-versa.”, Jessica explained.


Adam still didn’t seem quite convinced, but his fingers were tapping lightly on the bar counter top on which he leaned. His eyes were shifting slightly. He was obviously thinking.


“Ok… but i have conditions of my own.” Adam finally said.


“And those are…?” Jessica almost parroted Adam’s tone.


“There will be no contact with those people, ever again after the fact. No exchange of phone numbers, emails or anything like that. Each person is going to be a one-time deal.” Adam finalized his conditions, spelling them out firmly.


“Sounds fair enough babe… so, do we have a deal?”, Jessica asked.


It took Adam a few instants to finally nod his head in agreement, “Yeah… i believe so.”


Chapter 5: Trial Run


Adam’s phone buzzed several times before he had the guts to accept Jessica’s call. He knew it was time.


“Hey babe, whatcha doin’?” Jessica cooed him in her baby voice. She was obviously in a great mood.


“I’m doing good… just finishing some work at the office. I’m about to get off.” Adam responded, with a hint of hesitation.


“Yeah… you’re good at getting off hun. It’s been three days straight that you got off all over me like a firehose!” Jessica half-joked, as she bursted into laughter. “God… why do you have to come in my hair every goddamn time, babe? Seriously it takes forever to wash off…”.


“Force of habit, babe… are you coming over tonight?” Adam asked, trying to sound casual, hoping she would have forgotten about their ‘Open Date’ deal. Sadly it wasn’t the case.


“Nope… you are coming to pick me up babe, we are going out, so wear something sexy, i’m gonna pimp you out tonight.” was Jessica’s response.


“Right… ok, i’ll be by your place at around 8.” Adam replied.


“Great, see you soon hun.” Jessica cheered, before hanging up.


Half hour later, Adam felt he was driving to his own funeral. On the other hand, he did agree to it, and he had to give it a try.


Much to his dismay, Jessica looked every bit as ravishing as he feared.


Her choice of footwear was black leather boots, six-inch heels, pointed, cladding her perfect legs a few inches short of her knee.


Dark stockings wrapped her thighs, but there was no telling how high they went up her black, flared mini skirt.


Her top was a two-tones gray and black paisley pattern, where the black shapes were knit in sheer lace, vaguely hinting at the black bra underneath.


A short leather jacket draped over her shoulders completed the ensemble.


In a rare spur of the moment, Jessica elected to straighten her wavy hair, which was suddenly longer than usual, framing her doll-like face, and falling just barely above her breasts.


Adam had an instant hard-on as soon as she climbed in the passenger seat… as well as a knot in his stomach so painful he thought he felt ill.


“Where are we going?”, Adam asked, as he struggled to make eye contact.


“Let's go to the Tropicana. There's always a great crowd there on a Saturday.” Jessica replied as she checked her phone.


The Tropicana was a popular hookup spot. The bar was inside a large resort casino, strategically designed to be away from the billowing cigarette smoke covering the slot machines area only thirty feet away.


Most patrons were in their mid-30s, with the occasional older gentleman scouting for spinner girls, for a chance at feeling young again… or to once again discovering his own physical limitations.


The younger crowd was typically upper-class, professional, educated, and often overconfident. Many would be exceptionally fit and groomed, as most were well acquainted to a workaholic lifestyle, and ready to play hard when off the clock.


Jessica couldn't have thought of a better place where to find her Mr. Right Now.


“Would you be a dear and get me a pina colada, babe?” Jessica asked Adam nonchalantly, as they walked up to the bar.


A group of men in their thirties, all wearing black business suits, were gathered at the bar, cheering at the large flat panel TV. They were obviously Steelers fans, but Adam was never much of a football fanatic.


Apparently, Jessica turned into one for the night, as Adam watched her approach the three men, with her signature smile.


“Hey guys, how's Pittsburgh doing?”, she walked in, instantly drawing all three men's attention onto herself.


At least two of them looked like they could have played semi-pro football, while the third was shorter, but still rather strapping.


“They are killing it, 21-9, and another touchdown on the way. Green Bay doesn't stand a chance. What's your name?” the tallest one asked her, projecting a sense of confidence that only comes with a fat bank account, or wealthy parents.


“I'm Jessica, and you guys?” Jessica replied, as she leaned her slinky little self on the counter.


Adam stood at few feet from the group, waiting for Jessica's pina colada, and a dirty martini for himself. When the drinks finally came, he walked towards the crowd, only to find Jessica, chatting up and laughing hysterically, while leaning back against John, the tallest of the group.


As Adam approached Jessica with her drink, he couldn't help but notice John's hand on Jessica's right hip, stroking it slowly.


“Hey babe, thank you for the drink!” Jessica chimed, “Hey guys meet my best friend Adam!”, she announced, as Adam began feeling nauseated with every awkward handshake.


His mind was in a daze for much of the evening, as almost two hours went by, Jessica was having the time of her life, flirting with three men at once, and gulping down pina coladas like soda pop, until her face was flushed and her stance more unsteady, which worked out perfectly for John, whose chances at being the pick of the litter were rising considerably.


Adam and the two other men were having small talk, which Adam tried his best to keep up, as he just couldn't help noticing how Jessica's posterior was intentionally brushing against John’s crotch, until Adam's eyes went wide at the sound of Jessica yelling “Stop! Don't make me spill my drink, you'll get me all wet!”, followed by uncontrollable laughter.


Adam knew what was going to happen next, the moment he noticed her whispering something to his ear. It was time.


“Babe, do you mind if i leave you here with the boys for a minute? John has something in his room he wants to show me, we’ll be right back!”, Jessica suddenly announced, much to Adam’s dismay.


Adam was torn between storming out to let her know that her behavior was unacceptable according to their agreement, or stick it out and weathering the storm like a good little soldier, until she’d be done with the charade. At such point Adam envisioned there would be a conversation about the events occurred. One that could only have two outcomes.


Adam opted for having another drink, in an attempt to get his mind off of Jessica, while hoping she’d be back soon.


Four martinis later, Adam was struggling to keep up with his end of the conversation with the two other strangers before him. Right then, the corner of his eye caught Jessica, walking out of an elevator, with John right behind him.


“Hey babe, are you ok?” Jessica asked, noticing Adam’s face flushed, as his legs struggled to support his weight.


“I’m great… just having a few drinks with these fine gentlemen, hun.” Adam replied. He was drunk, but not drunk enough not to notice Jessica was wearing her top inside out, and a dark stain was visible under her jacket, right along the ridge between her breasts.


“Babe, you don’t look like you can drive. Give me the key, we are taking you home.” Jessica ordered him. Adam’s ears irked at the sound of ‘we’, from Jessica’s mouth.

Nevertheless, he chose to play nice. “Ok babe, i guess i had enough anyway.” Adam responded, as he unsteadily lifted himself from the bar stool.


Adam sat in the backseat, and drifted in and out of consciousness several times before Jessica pulled into her building’s driveway.


Each time, he’d wake up to the sight of John’s hand, reaching for Jessica’s thighs, and at one point, well above that. He could hear Jessica chuckling, and giggling, on occasions swatting John’s hand away, but more often than not, giving in to his sexual innuendo and teasing, while she struggled to keep her eyes on the road.


Finally, the car stopped, and Jessica opened the door for Adam, who was by then a bit more conscious and aware. His mind had begun clearing a bit, with the cool air, and he was able to walk by himself, right behind Jessica and John, on their way to her apartment.


Once inside, Jessica threw her jacket on the floor, while Adam plopped on her living room couch, and leaned back, while watching Jessica pulling John’s arm, and towing him towards the sectional sofa next to where John was sitting.


Jessica pushed John on the couch, and proceeded to climb on his lap, kissing him and grinding herself against his crotch, which had been bulging since before they entered the apartment.


Adam watched as Jessica pulled her top over her head and dropped it next to Adam’s feet. There was no trace of her bra, as Jessica’s breasts and quarter-size brown nipples swung freely, for John’s amusement.


It didn’t take long for John’s hands to get to work, as his right hand was already playing with Jessica’s breasts, pinching her, and twisting her prominent buds, while his left hand was delving under her skirt, probind her crotch, and running his fingers across her slit, through the dark pantyhose.


Jessica’s hands were interlaced behind John’s neck, as she leaned her body forward, causing her breasts to close in on John’s face, until his mouth came into contact with her nipples.


Judging by the motion, and Jessica’s noises, John knew his way around a firm pair of tits. His mouth enveloped almost half of Jessica’s right breast, and Adam’s stomach began turning as he witnessed John’s teeth, tongue and lips expertly working Jessica’s breasts, until her hips begun gyrating and grinding faster against John’s crotch, finally rock hard.


Jessica’s hands let go of John’s neck, and moved behind her back, and under her ass, reaching for John’s bulge. It didn’t take long for Jessica to find his zipper, and free the massive erection underneath. John’s member wasn’t comparatively much longer than Adam, but its girth was impressive, and Jessica’s fingers were barely able to close around its fully erect cock.


His shape was unusual, not unlike an upside down eggplant, with the upper half noticeably thicker than its base. If the memory of Jessica’s ‘practice dildo’ she used while dating Aaron served, Adam had a feeling that John’s cock, while nowhere near as long as Aaron, was very similar in girth, perhaps even thicker.


Jessica was most definitely intent on finding out, as she suddenly climbed off of John’s lap, and practically teared off her pantyhose, and g-string, before climbing back on John’s lap.


“Fuck, i want this in me now…” Adam heard Jessica grunt, as she guided John’s head into her already dripping wet slit.


The massively thick rod disappeared inside Jessica’s pussy, while simultaneously knocking the wind out of her lungs. Her mouth was gaping, and her eyes glazed over, for almost a minute, as she felt John’s member stretching her wider than she had so far.


Once every inch if John’s cock was buried deep inside her, Jessica proceeded to buck into him, relentlessly, working his cock harder and deeper than she ever had, slamming herself harder and harder onto him, while her breasts bounced up and down before Adam’s eyes.


In the meantime, Adam’s brain cleared off the previous inebriation, as he came to his senses slowly, but steadily.


Soon enough, he was able to stand, and walk himself to the restroom, while Jessica was far gone into her own pre-orgasmic high.


Adam locked himself in the bathroom, and leaned against the sink, trying to make himself vomit, for some reason, even if he had no need to.


Ultimately, he gurgled some mouthwash for a minute, spit it out, and took what felt like the longest piss in his life, while rhythmic pounding and slapping noises filled Jessica’s apartment, and filtered through the thin bathroom door.


When Adam finally emerged, and walked back into the living room, Jessica was still giving John a vigorous fucking, while glancing at Adam, with lustful eyes. Only he knew very well that lust wasn’t for him.


Still, it didn’t explain why Adam’s cock begun to swell to a noticeable size, until it was rock hard.


“Come here babe… “ Jessica ordered him, in her usual commanding tone.


Adam had a good mind to simply leave the apartment, and drive back home, but somehow he didn’t. He complied, walking towards Jessica, until he was standing right next to her, close enough to hear the sloppy sound of her wet pussy being impaled by John’s cock.


“Show me that cock, babe…” Jessica prompted Adam, who was well aware of the bulge in his pants. He proceeded to unzip his fly, and undo his belt, then pulled down his boxers, to reveal his member, erect and ready.


Jessica’s hand reached for it, and begun to stroke it, slowly at first, than faster, as John’s pounding from below increased in intensity. “Fuck he’s so much thicker…!!” Jessica moaned, as she glanced at Adam’s cock, “I swear babe…” she continued, chuckling in between strokes, “Feels like a fist, i swear God…”.


At that, Jessica pulled Adam closer, and leaned towards him, until he was close enough for her mouth to envelop his cock and suck it.


The feeling was surreal. The faster and harder John fucked Jessica, the more intense Adam felt while Jessica blew his cock, especially as Jessica’s fingernails dug into Adam’s asscheek.


Not too long a time went by before an pre-climax rush washed over Adam’s body, building up towards his orgasm.


When Adam finally came, Jessica struggled to keep him inside, as John pounded her even harder. Within minutes, Jessica’s mouth and the back of her throat, was coated in Adam’s thick spunk, which Jessica swallowed whole.


Adam was spent, once again, and dropped on the same spot where he sat before, while John grabbed Jessica’s ass and pushed her off of him. “Now you are really gonna get it…” John grunted, as he stood up, and prompted Jessica to lean on all fours, on the couch.


Adam watched as John spat several times, on his hand, and rubbed copious amounts of saliva around Jessica’s asshole, in addition to juices dripping from her pussy.


“Here it comes… ready?” John announced as he lubricated his own cock in spit. To his amazement, Adam hear Jessica respond with a resounding “Fuck yeah… give it to me baby!”


That was all the motivation John needed to begin his cock’s descent into Jessica’s rear entrance. The one place she never allowed Adam to go.


It took John several minutes to sink his cock only two-three inches into Jessica’s hole, while constantly lubricating the entrance with his spit.


When he was finally past her rim, the motion changed. John started pistoning, in and out of Jessica’s rear passage, pushing more of himself in, to a depth Jessica has rarely experienced.


Jessica was silent the whole time, but her grunts and low moans spoke for her. Adam was mesmerized. He couldn’t move or speak, until ten minutes later, when John’s body stiffened, and he reached his own climax, and filled Jessica’s anal passage with his jizz.


At that, Adam’s eyes dropped to the floor. He shook his head, imperceptibly, pursing his lips, as John emptied his last spurt outside, on Jessica’s back.


“Fuck, you’re tight, babe… “ John remarked, with a grin on his face. Jessica’s face was buried into the couch’s cushion. Her breathing was fast and laboured. Her hands were grasping the hem of her own skirt.


“Oh my God… you are like a jackhammer!” Jessica commented, between heavy breaths, “I think i lost count of how many times i’ve come… fuck!” Jessica finalized her thought.


In the meantime, Adam lied on his back, and closed his eyes, until the world around him became a dark blur.


When Adam finally woke up, it was almost five in the morning. Noises from Jessica’s bedroom caught his attention, and he noticed John’s pants were still on the floor.


He walked by Jessica’s door, only to hear low moans and grunts from within. John was obviously going to stay a while.


As Adam gathered his clothes and looked for his car keys, his mind wandered in different directions. Much to his surprise, he wasn’t completely dismissing the possibility that such arrangement could work. He proved himself to be quite aroused the night before, after all, which had him think very hard before taking a stance against Jessica’s unorthodox approach to relationships.


Most importantly, Adam realized that such arrangement was what made Jessica happy. In his new twisted world, Adam knew that Jessica’s happiness was all that mattered.


Whether his ego or common sense could take as much pounding, as Jessica’s orifices were going to, was the ultimate question on which Adam’s commitment to Jessica, hinged.


The fact of the matter was that he had never come as hard as he did the night before, while Jessica’s pussy was being mercilessly stretched by her stud of choice.


Jessica was well aware of it too, which is why Adam had a feeling she knew what she was doing, when she took Adam’s car keys to the bedroom with her and John.


To be continued...

Category: consensual cuckolding

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