Walk of Shame Ch. 02

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It wasn’t exactly how Jacqueline Montero envisioned that glorious, and long looked forward to day. Sitting among the throngs of assembled family members and well wishers beneath the early Spring sun in our Nation’s Capital, Jacki joined countless other parents as they watched their children walk across the stage with their diplomas from Georgetown.

Years earlier when Jacki began prepping her only Daughter, Randi, for the college experience, she had little doubt the day would come. The periphery circumstances when that day came however were another story.

Divorced for going on five years, Jacki didn’t begrudge her Ex, Earl, one bit for being there to see their only child graduate. Sitting in the folding chair beside him, two seats down from her however was Earl’s new fiancé, his very young and very pretty fiancé. Further muddying the idyllic fantasy Jacki had of that special day was the absence of any significant other there accompanying her as her Ex basked in the glow of his new conquest.

Through it all, Jacki kept a captivating smile and a stiff upper lip, safe in the knowledge that her own selfish reward may be waiting sometime later that night.

But first, she had to make it through the excruciatingly long and drawn out graduation ceremony.


Jacki remembered thinking how glad she was Randi’s last name ended in ‘M’, knowing the wait would have been interminable if she had to go much deeper into the alphabet to see her Daughter walk across the stage.

Standing proudly and positively beaming when Randi Montero’s name was called, Jacki instinctively looked over and gave her Ex-Husband a quick glance of shared accomplishment as soon as their only child shook the School President’s hand.

Even that serendipitous moment of peace was somewhat tainted when Earl’s fiancé looked over as if to say “That’s enough, you two”.

Returning her gaze back to the stage, Jacki could still feel her heart pounding as she watched her Daughter descend the steps and re-join her fellow graduates in the audience.

With Randi’s special moment out of the way, the act of having to sit there listening to all the other names get called became quite monotonous. It wasn’t long before Jacki began craning her neck to scan the crowd, wondering if any of the men she’d made plans with that night might be in attendance as well, perhaps even walking across the stage that afternoon to get their degrees.

The endorphins of euphoric pride coursing through Jacki’s system were gradually replaced by an excitement and anticipation of a completely different sort, one that caused her to stir nervously in her seat as the rest of the graduating class proceeded, one by one, across the stage.

Eventually the exercises played themselves out and after taking enough pictures of Randi, among assorted others, to fill a scrapbook, the crowd began to dissipate and Jacki found herself in the car with her Daughter, her Ex and his Fiance headed back to Randi’s apartment to put a bow on the afternoon.

Every so often, Jacki found herself checking the messages on her cell phone, seeing if the stranger she was supposed to meet later that night had sent any new information. By chance he had. Fighting off a terrible blush, Jacki sent him a text back without anyone else in the car noticing.


Back at Randi’s place, the foursome made small talk, nibbled at the meat and cheese platter they’d brought home, took a few more pictures then said their good-byes. Earl and his Fiance took off around six that afternoon, leaving Jacki there with her Daughter. It wasn’t long before Randi was upstairs however, showering and getting herself squared away for the party she was headed to.

The time alone allowed Jacki to cement her plans for the night.

When Randi finally came bounding down the steps, all made-up and ready to head out, she couldn’t help but notice her Mom still had the same fancy dress and blouse set she’d worn to the graduation ceremony.

“I forgot to pack anything casual,” she told her Daughter. “Was just checking some movie times online when you came down..think I’ll head into town and catch an 8 o’ clock showing of something.”

If she hadn’t been in such a hurry, Randi would have certainly interrogated her Mother a little more than she did, knowing full well Jacqueline Montero would never ‘under pack’ for any trip, big or small. Given the rush to meet up with her friends, Randi kissed her Mom on the cheek and headed out the door, the two women going their distinctively different directions for the next 12 hours.


Jacki would have probably been much more comfortable in casual attire as well. Having to undress out of her formal wear she’d worn to the graduation, just to shower and pretty herself up before putting that same tight black skirt and form fitting blouse right back on wasn’t something she’d normally do. It was, however, Escort Bayan what had been asked of her by the men she was preparing to meet.

Once she began blow-drying her hair and applying her lipstick, the anticipation really began to take root inside Jacki’s chest, as if making what was about to happen start to seem real. Stepping into the brand new pair of thong panties she’d brought for the trip, Jacki snugly rolled the lace top of her black stockings into place as well before she slid her feet into her equally new high heels.

Checking herself in the mirror several times before heading downstairs, the last time she felt this nervous about making a grand entrance was the day she got married way back at the age of 18. By the time she’d stepped outside into the early evening dusk, she didn’t feel a bit like a freshly primped bride however, more like a virgin being offered up for sacrifice into the flames of a spewing volcano. And given the 41 year old divorcee’s current state of mind, she wouldn’t have had it any other way.

Punching the address she’d been given into her GPS, Jacki pulled out of her Daughter’s driveway, feeling as if a much higher power had taken the wheel. Thinking back to the genesis of how all this came to be as she followed the digital navigator’s instructions, Jacki could still feel her pussy throb on cue each time she re-lived her online masturbation session with that kid from Iowa. The lust that had been building inside her had mixed perfectly that night with the complex recipe of emotional gunpowder and wine in her system until every nerve ending in her body seemingly exploded when that handsome young stranger so crudely lit the fuse.


For the initial few days after her drunken encounter online, Jacki feared even attempting to log on to any of the personals sites she frequented. Like anyone with a growing thirst however, once a few days passed without the required sustenance, Jacki once again found herself hunkered down at her computer well after Midnight.

Her first inclination was to try and catch back up with the young man from Iowa, but quickly decided against it. The first encounter with him had been such a glorious hit and run, Jacki feared if she shared another quality chat with him, she may start feeling some emotional attachment. And given the circumstances, that was the last thing she wanted.

The digital landscape being littered with guys ripe for adult conversation, Jacqueline Montero knew a woman of her looks and curiosity would quickly attract an overwhelming host of suitors.

Finding another guy to help satiate those unsheathed libidinal urges wouldn’t be a problem. Whatever it was Chris had pulled from the depths of Jacki’s psyche had all but made her forget about trying to find a date to accompany her to her Daughter’s graduation. It had tapped into such a concentrated euphoria, a lot of the stuff that use to matter to Jacki suddenly didn’t seem to matter all that much. Like any freshly birthed monster however, the feeling needed to be fed.

She could have chosen from an infinitely diverse array of online ads, knowing most any guy she struck up a dialogue with would eventually bring the conversation around to sex if she let him. Her base, primal need sliced open in the darkened privacy of her home office, Jacki found herself searching out ways to raise the bar even higher from what she did a few nights earlier with Chris.

The first bit of dabbling took Jacki down a road she’d never fathomed. At some point that evening she received an invitation to chat from a rather imposing and ruthless looking gentleman from New York. Broad shouldered with chiseled good looks, Jacki felt smitten as soon as they started to chat.

There was one problem, however. A few minutes into their increasingly risqué conversation, the man mentioned he was married. While that certainly wasn’t a startling revelation given the nature of the internet, when the guy mentioned his Wife was sitting just off camera, Jacki was at a complete loss.

Far from naive, Jacki understood full well there were couples out there into that sort of thing, but had never once dealt with anything to do with that particular lifestyle. Her blood cells already feeling like chips of ice as they staggered through her veins, her internal plumbing just about ceased totally up when the man waved his Wife over to the cam, as if to show Jacqueline he wasn’t kidding.

Jacki’s first reaction was to hit exit and move on to something else, but she was so stunned and taken aback by the silent rapport of the couple on the screen that she couldn’t bring herself to turn away. There was a clear look of submissiveness in the woman’s expression and posture. In the light of day she may have been a respected bank teller or saleswoman, but there at a little after one that morning, she was clearly her Husband’s willing sexual pawn as he showed her off like a pet for Jacki.

The longer she sat there absorbing the psychic hold the man had over his Wife, the more Jacki found herself falling under his spell as well. Having no idea she’d even done it, Jacki allowed her left hand to drift beneath the desk, and between her thighs, as she used her right to type back and forth with the man on the screen.

It wasn’t long before she allowed him to turn his mic on so they could chat directly.

From there, it also wasn’t long before the man’s stern, seductive voice was sending chillbumps down Jacki’s back. Wearing nothing but a sheer, peach colored floral nightgown as she sat in front of the computer, Jacki parted her knees and dithered at her pussy as she talked to the stranger. Even though he didn’t feel the need to tell her as much, she could tell from the approving look in his eyes he was happy to watch Jacki play with herself. And even in that short amount of time, strangely, his approval meant something to her.

Jacki told him she was divorced, but had never had any sort of experience dabbling with another couple. It was clear from her on-going interaction with the gentleman however that she wasn’t exactly turning to run the other way.

Her fingers now soaked in the oily sheen of her flowing vaginal stew, Jacki continued to lose herself in her interaction with the imposing stranger, even though it was clear the man’s wife was sitting right off to the side watching it all. Wrenching her left elbow at an awkward enough angle that made it clear what she was doing under the desk, Jacki found herself becoming increasingly aroused by the man’s seeming, stone-faced ambivalence, as if he was forcing her to raise the stakes just so he’d notice her efforts and give his approval.

It was clear where the conversation was headed, but the gentleman showed no outward inclination to play his hand just yet. No wanting to come right out and ask the man to pull his cock out so she could see it, instead Jacki ratcheted up her efforts, squeezing her tits through the top of her nightgown before finally pulling the strap over her shoulder and allowing the fleshy pendulum of her left breast to rest in full view of her computer’s camera.

The sight of her bare breast did send a ripple of emotion through the man’s face, but it didn’t do anything to speed up the calculating pace of his cyber foreplay.

“Pull the rest of your gown down, Monica..show me both of them,” he told Jacqueline between drags of a cigarette.

Smart enough that time not to give out her real name, it provided the anonymity needed to do things she never would in broad daylight. Pulling her greasy left hand free from her crotch and raising it up to her right shoulder, Jacki pulled down the second strap as well until the gown was bunched at her waist, allowing her ample bosom to swing completely free.

“Nice,” the stranger nodded as he leaned back with a subtle but victorious grin on his face.

Seeing him lower his hands to his crotch in the age old movement of a man preparing to pull down his pants, Jacki leaned forward expectantly in her chair and licked her lips.

Once again, the next few moments didn’t unfold exactly how she’d envisioned.

So enthralled with her primal want for the man on the screen, Jacki had momentarily lost track of the guy’s Wife. Her eyes focused on the pixilated image of him pulling his manhood free, Jacki eagerly squeezed at her already swollen nipples, tweaking them like fat grapes until a groan of appreciation rose like thick smoke from her throat.

“Nice,” she returned the man’s compliment when she saw his erection rise majestically from his groin.

While it didn’t have the comic proportions of the kid from Iowa’s, his cock certainly looked like it could do all the damage he needed, especially attached to a man with that sort of heartless and hungry gleam in his eyes.

Snapped somewhat from her hypnotic fog when the man reached to his right and once again guided his wife into the camera shot, Jacki recoiled in her seat and watched the attractive, middle aged blonde wrap her petite hand around the man’s jutting phallus.

Discreetly slipping her fingers back down to her own simmering crotch, Jacki’s heart thudded in her chest seeing how the woman’s thin fingers stretched as far as they could around her Husband’s bulging shaft. Through it all however, the man never took his eyes off Jacki as he stared into the monitor, causing her insides to boil as the guy’s wife gave him a slow and steady handjob.

Spinning her own fingertips rapidly across her clit, Jacki’s hips began to swivel in the seat when the woman on the screen kneeled down beside her seated Husband.

Her breasts swaying side to side as she gouged at her pussy with her left hand, Jacki’s eyes narrowed intently as the woman opened her mouth and devoured the upper half of her Husband’s cock.

“SSHH..AAAHHH,” a raspy gasp sizzled from Jacki’s throat, her heels digging into the carpet below as she parted her knees wide beneath the desk.

Her gaze focused squarely on the way the head of the man’s prick bulged the woman’s cheek out each time she stuffed more of it between her lips, Jacki dizzily spun her fingers across the buzzing nub of her clit as she maintained unblinking eye contact with the man in front of her.

“GAAWWDD..YEESSSS,” Jacki hissed a few seconds later, her head rocking backwards as her pussy juices splashed all over her scouring hand.

“Wish it was you here on your knees, Monica?” he looked into the camera and smiled, rubbing his right hand lazily through his Wife’s blonde hair as he watched Jacqueline masturbate from a couple hundred miles away.

There was no need for Jacki to vocalize a response. The way she nodded her head like a punch-drunk fighter and slouched even deeper in her seat as she jabbed her hand between her thighs communicated everything that needed to be said.

Knowing, beyond a shadow of a doubt, that man was imagining fucking her as his own Wife eagerly gobbled his cock somehow filled Jacki with an evil sense of accomplishment. To think he would be so crude and open about his lust for her that he would freely sit there staring at her on the screen, while his own Wife knelt at his feet pleasuring him, stirred something so complex and empowering inside Jacki that there would be no way to truly describe it.

Prodding herself ever closer to release, Jacki clenched her free hand around both breasts and fiercely squeezed them, the entire time fantasizing the nameless man she was staring at was the one actually there doing it.

Within a matter of moments, Jacki’s feet began pumping on the floor.

The married woman’s head bobbing up and down in the corner of the monitor’s frame, Jacki dared not divert her gaze from the stranger’s eyes, determined to peer deep into his soul (if he had one) the instant she came.

Fingering her pussy with the same velocity of an exuberant child playing a new game of Hungry Hungry Hippos, Jacqueline gritted her teeth and seized every muscle in her body up as the friction inside her marrow expanded to crippling proportions. Seeing the twinkle of appreciation in the man’s otherwise dark eyes was all it took to send Jacki hurdling over the edge.

“AAAAAAAAHHHHHHHHHHHH……AAAAHHHHHHHHHH,” she screamed, her embarrassingly loud wails filtering through every room of her modest home before carrying all the way to another residence in New York through the magic of the internet.

As expected, the sight of Jacqueline cumming set off a violent chain reaction. In very short order, the man’s face tightened on the screen just as his hips began churning upwards in his chair. Her own orgasm still washing like a riptide through her synapses, within a few brutal seconds Jacki watched through her slitted eyes as the man’s rich, milky semen streamed out of the corners of his Wife’s overwhelmed lips.

Sliding ever lower in her cushiony office chair until her eyes were nearly parallel with the image on the screen, Jacki clamped her left hand tight around her cunt and kneaded out another debilitating release watching the way the stranger greedily fucked his kneeling Wife’s face until he’d expended his frothy seed.

Through it all, Jacki was transfixed, bathing in the aura of their shared orgasmic bliss.


It nearly killed her to break that unspoken bond, but the instant the cold wind of reality began to seep into Jacki’s head, she reached for the keyboard and exited out of the chat with the couple from New York.

Her ears immediately popping as if she was returning to Earth after some sort of cosmic voyage, Jacki sat there in the silence of her own home, covered in the dim light of her computer screen, trying to determine if she had the strength left to drag herself up to bed. The same way the guy from Iowa’s cock had somehow seared it’s phallic image into her brain, the guy who she’d just been chatting with’s heartless and knowing gaze was now engraved forever in her memory bank as well.

Clearly feeling as if she’d set sail in a direction she couldn’t turn back from, Jacki’s next interlude would take on a much more patriotic tone.


Just like her first indecent encounter online, Jacki was a tad hesitant about logging on after such a debaucherous encounter with the couple from New York. Eventually her crazed need for attention won out and she found herself trolling several sites that a few weeks earlier she would have cringed at the very thought of. Not surprisingly, once online the pings quickly began building up in Jacqueline Montero’s inbox.

If Jacki thought getting propositioned by a kid all the way out in Iowa was a stretch, receiving a message from a young man stationed in Afghanistan truly drove home just how small the world had become.

Twenty year old, Private First Class Alex Salazar, from Denton, Texas had stumbled across Jaqueline’s ad at a meet & greet site, and like a few dozen other men that night, decided to drop her a line. What made Jacki answer that particular one, she’d never know.

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