Walk of Shame Ch. 01

Once again Jacki was left without a quick reply, partly due to her inebriated state, but also the boy's composure and forwardness.

"I'm Chris, by the way," the 19 year old filled the growing gap of silence.

"Hi Chris...I'm Jacqueline...most people call me Jacki," she replied, instantly regretting giving out her real name.

"Just calm down," she chided herself. "He doesn't know its your real name and besides, he lives nearly 2,000 miles away. I don't think your circles of friends are going to overlap."

"What are you studying at Penn?" she asked, immediately feeling old asking someone that young such a trite question.

"Just getting some credits built up right now." he told her amiably. "Thinking about maybe doing Pre-Med down the road."

The conversation jump started, the two proceeded to chat back and forth for another five minutes or so until Chris made a suggestion.

"I've got a cam."

They were only four little words, but each one pricked Jacki's spine like tiny ice-picks. Feeling like she'd committed too much to the dialogue to simply log off and run away with her tail between her legs, Jacki replied back that she had one as well.

"I've got a mic too," Chris added.

Within a minute, through the magic of the internet, 41 year old Jacqueline Montero was face to face with 19 year old Christopher Stockman.

Considering how many men she'd encountered that looked nothing like their profile picture, Jacki was at least encouraged the blonde haired, blue eyed guy on her screen had been honest about his appearance. That reassurance didn't do anything to quell the unease growing in her chest however.

___________________________________

What Chris saw when he stared into the monitor brought a Cheshire grin to his sweet and innocent face. Jacki was exactly what he'd been looking for that night.

Studying the way her long black hair looked somewhat strewn and messy as she rubbed her fingers through it, Chris could tell Jacki was up past her usual bedtime. From the pronounced blush of her pale, olive skinned cheeks, it didn't take a genius to guess she'd been drinking as well. The fact he could see what looked to be a mostly drained bottle of wine to the woman's right just confirmed it.

Noticing no distinctive ring on Jacki's left hand, he felt safe in his assumption she wasn't married. Considering the late hour back East and the woman's failing state of sobriety, he had a fair insight into Jacki Montero's mindset, even if she didn't.

Continuing to project an aire of subdued calm, Chris' ears perked up when he heard Jacki mumble, "I can't believe I'm doing this," several times.

"Doing what..we're just talking?" he looked directly into the camera and smiled.

All Jacki could do as bow her head bashfully and take another sip of vino.

"Yeah..you're right," she managed, even though the ground beneath her was steadily giving way.

Another pocket of silence played out between the two as they visually sized each other up on the screen.

Chris thought about commenting on the nearly empty bottle of wine beside Jacki but decided to leave it be. Instead, he did what any self respecting horny 19 year old would, he focused on the swells of the woman's cleavage in her loose fitting tank-top.

"So...how many women have you met on here..do you talk to a lot of girls?" Jacki asked.

"Not many..I've been so busy with exams at school and just flying home the other day..I haven't even been on here for a few weeks..just sitting home bored tonight and decided to log-on...that's when I saw you were on-line too," he matter of factly replied.

Jacki put her chin in her right hand and swirled the wine in her glass with her left as she tried to glean the honesty in the young man's answer.

"What does it matter?' the playful voice of want bubbled up from the depths.

"...He's 19...,' the fading wisps of her rationale replied, but it struggled to add anything else.

"What were those extenuating circumstances you mentioned earlier..you don't have something terminal do you...just on the screen here..you look pretty healthy?" Jacki quizzed without trying to come across as nosey.

"No..its nothing terminal exactly...just a condition that complicates certain relationships at times," Chris nodded his head passively towards the camera.

"Hmmm," Jacki visibly sighed, unsure if she should continue with this line of questioning.

"You're not like..bi-polar...or...?" Jacki started to ask, trying not to tread too deeply into the young man's personal issues.

"No...I think we're all messed up in our own special way..but I'm not on meds for anything," Chris responded with a friendly, open ended smile.

"God..then what?" Jacki's eyes seemed to beg as she took another sip from her glass.

It wasn't lost on Chris how the woman on the screen had to, ever so slightly, start and stop a few times before she got the wine safely to her lips.

"I hope she doesn't conk out like that woman did a few months ago when I was IM'ing with her at school..we were rolling along so good and she just passed right out," Chris thought as he watched Jacki swaying in the winds of intoxication in front of him.

"Do you have some sort of birth defect?" She sniped in a tone she certainly wouldn't have used in the sober light of day.

"I guess you could say that..didn't really realize just how bad it was until a few years ago," Chris crypticly replied, and left it at that.

Jacki looked as if she had a lump in her throat as she tried digesting what the guy on the screen was alluding to. Having worked for years as an office manager for a group of doctors, there weren't too many physical maladies she hadn't at one point or another heard of.

Any hope of steering the conversation towards the weather, the failings of the Obama administration, or any number of other trivial directions was long since passed. Feeling as if her judgment had been lifted up off its foundation and carried away by the flood waters of her inebriated state, Jacki simply couldn't stop herself from coming right out and asking about the condition Chris kept alluding to.

"You're gonna log off as soon as I tell you," he warned. "Just like a couple of other women have."

"I'm a big girl..I've seen pretty much everything a person can throw at another," Jacki assuredly shot back, her curiosity now stoked more than ever.

"Are you sure?" he asked once again, leaning back in his seat as if waiting for the older woman's final go ahead. "You promise not to exit out as soon as I tell you?"

"Yes..I promise," Jacki took a deep breath and replied, praying she wouldn't regret those words.

"I have an issue ...when I'm intimate with women...sort of an issue with my penis," Chris' monotone voice came through the mic like a confessional, filling Jacki's head along with the small office surrounding her.

"Oh..you guys are so insecure about that sort of stuff...I wouldn't worry about it one bit..there are so many other ways to make a girl happy..." Jacki blathered on for a few seconds as Chris just sat there trying to keep a straight face.

"Actually...," Chris chimed back in when he allowed the temporary patch of silence to run it's course. "I sort of have the opposite problem."

"...Bull...shit," was Jacki's incredulously blunt and certain response, even though it came out a little disjointed due to her drunken condition.

Chris rolled his eyes and smiled, having dealt with that reaction before.

"You asked," he offered, giving Jacki the chance to collect herself and change the subject.

"You expect me to believe that," she instead insisted, as if determined to press the issue. "If I had a dime for every wanna-be John Holmes I've met online..I'd be..."

"It's not like I mentioned it anywhere on my profile," Chris politely interrupted, causing Jacki to clam up and freeze for a few moments as she contemplated what he said.

"Let me guess...most guys want to pull it right out and show you, don't they?" Chris prodded.

"Yeah..either that..or they send a picture of it but conveniently send one that doesn't have a face with it," Jacki nodded.

"I still don't believe you by the way..no way anyone can have something that would totally complicate having relations with a grown woman..its just ridiculous!" she continued, her voice slightly more sober and thoughtful than it had been before.

"Have had to take two separate girls to the hospital over the past year and a half," Chris offered with an utterly straight face.

"WHAT?" Jacki grimaced with comic effect. "To the hospital..for what?"

"A combination of liquid courage and biting off a little more than they could chew," he told her. "Couple of girls from college..one Freshman and one Junior...Both were fine after the fact but they thought they may have damaged themselves after the initial adrenaline wore off."

Jacki simply sat there staring off in the distance, her mouth a tad more agape than before Chris mentioned the last part.

"I've kind of found out the hard way being intimate with girls my age may be a little tedious. Not saying there aren't a few that may be able to handle it, but generally I've had better luck with older women..especially ones that have had a few kids," he continued with the same nonchalance of a guy describing a trip to the mall.

There may have well been a 'vacancy' sign posted across Jacki's forehead as she processed what Chris was saying.

"I still don't believe you," she offered weakly, clearing sounding as if she was starting to.

"Knew there was something different about me once I got to high school and some of the guys in the locker room would look a little different at me in the shower..creepy I know..first time I had sex with a girl from school..she'd been around the block a few times..her reaction sort of cemented it," he added on, as if oblivious to Jacki's continued disbelief. "I never had sex with a girl again until I got to college last Fall and started branching out my horizons ..last thing I wanted was word getting around my hometown. Now I'm stuck here all Summer."

"Uh..huh," Jacki replied, visibly shivering a few times as the tangible weight of Chris' story settled like snowflakes down her spine.

"They had to go to the hospital?" she asked again, as if her mind was on random disconnect.

"We were just fooling around a little..just like a million other college kids in their Freshman dorm. Basically just heavy petting..she put her hand down on my pants and kind of jumped back. Once she steadied herself she leaned forward and snuck her hands inside," Chris relayed the story, clearly noticing the way Jacki was now fidgeting in her seat.

"She was drunk and determined and somehow I got it inside her and we wound up going at it for about 10 minutes before she finally gave out. She got sober real quick and started to worry that some real damage might be done..there was a little blood so I took her across campus to the medical facility. They kept asking the girl if she'd been raped and she kept telling them 'no'. I waited in the lobby the whole time and you can imagine the looks I got from the nurse on duty."

"The second time was a few months later. Was at a party with a Junior in somebody's spare bedroom...we wound up back down at the medical facility at about 2am...as luck would have it the same nurse was also on duty that night. How fucked up is that!"

This time Jacki couldn't even manage a "Uh-Huh". Instead, she just sat there speechless in front of the screen as the young man's words resonated in her head. The one thing she did notice however, even in her dumbfounded state, was how Chris' right hand had dipped beneath the desk and it was clear from the way his arm was flexing what he was doing with it.

"God, don't," her conscience railed but she couldn't stop herself.

"Can I see it?" the 41 year old divorcee sheepishly mumbled into the mic.

Rather than springing to his feet to do exactly what the older woman had so hesitantly asked, instead, Chris didn't budge, as if forcing Jacki to wallow in what she'd just said.

"Is that what you really want?" Chris looked straight into the camera and asked, his eyes accusatory and unflinching until Jacki eventually rocked her head up and down.

Realizing all her defenses were shot, Jacki leaned back in her seat and raised the last of the wine to her lips. Even from a half a country away, she felt the anticipation burning like an ulcer in the pit of her stomach when Chris started to stand up. It didn't take long, even with the spotty quality of the connection, for Jacki to notice the protruding bulge in the 19 year old's gym shorts.

A few beads of wine dripping out of the corner of her mouth when she missed somewhat with her aim, Jacki's chest rose and fell several times as she watched Chris dip his hand inside his waistband. Her breathing ceased when he finally swung the full length of his manhood free.

Jacki had always heard that TV added 10 pounds but she had no clue if that translated to computer screens as well. It sure looked to be the case however when Chris unsheathed his erect cock for her perusal. Straining her watery eyes to accommodate her depth perception, it didn't really sink in what she was seeing until she noticed the girth of Chris' penis was wider than the width of his wrist. Shifting in her seat as her insides continued to twist, Jacki's brain struggled to make any rational sense of what her eyes were transmitting.

"Something like that just doesn't look right attached to someone so slender," she tried convincing herself.

Chris didn't bother to say anything for a few seconds. He didn't have to. The drunken look of awe on Jacqueline Montero's face was much better than any, 'I told you so'.

The only reference point Jacki had to what she was seeing was the final scene of that "Boogie Nights" movie she saw years earlier. Even then, she was sure there were elements of either trick photography, or a casting call that took weeks to find the right specimen.

As if Jacki needed any more context for what she was visually processing, Chris removed the watch from his right wrist and placed it around the shaft of his cock. It was clear, even across Jacki's internet feed, how much more the band of the watch flexed around his bulging shaft than it had around Chris' lower arm. Crudely enough, the face of the watch was facing the camera.

"11:47" she noticed, quite a symbolic reality check considering how her own watch seemed to be synchronized exactly an hour faster.

For all his obvious gifts, there seemed to be very little arrogance or bravado in Chris' nature, simply an air of "Here it is, just like I promised."

"Was it what you were expecting?" Chris' voice drifted from her speaker.

"...I really don't know what I was expecting," Jacki half laughed, her words sounding like weak gusts of wind sweeping from her lips as her two nipples perked up and poked noticeably through her tank-top.

Reaching down to remove the watch and put it back on his wrist with the casual aplomb of a magician who'd performed the same trick hundreds of times, Chris kept the head of his bobbing manhood aimed straight at the camera, its pee-hole staring all the way to Delaware like the spying single eye of a Cyclopes.

Flailing her hand, trying to secure a grip on the nearly empty bottle of wine sitting on her desk, Jacki couldn't escape the symbolic connotations of trying to wrap her fingers around the rounded vessel considering what she was staring at on the screen. Alas, the bottle was all but empty, leaving her brain scattered trying to remember if there was another one in the house to open.

"Are you turned on, Jacqueline?" he seemed to taunt her through the mic, the distinctively leading question taking on a whole different tinge with the way he used her full name.

"Uh...Well...I...Ah...," Jacki stammered, unsure how to answer such an obviously loaded question, but still keep what was left of her decency and self respect.

As if exposing his erect cock to her wasn't brazen enough, it was nothing compared to what he asked her to do next.

Sensing the internal struggle taking place inside the older woman, Chris knew getting her to verbalize how turned on she was would be tough. If he was going to put in that sort of effort, he decided he'd rather for her to show him.

"Are you getting wet Jacqueline?" he mouthed in a tone that would make a hypnotist proud.

Continuing to stroke his cock for the camera as he studied each and every one of Jacki's facial ticks, Chris watched her shake her head side to side with very little conviction.

"Dip your hand down into your pants," he told her with the same casual ease of a guy asking someone to pass the salt.

"Swirl your hand down there a few times then pull it out and show me how wet your fingers are," the 19 year old continued to prod, making sure he traced his fingertips along the ridged head of his jutting penis for Jacki to clearly see.

With one click of the finger, Jacki could have easily closed the window and never had to worry about seeing that kid from Iowa ever again. As drunk as she was, by the next morning she'd probably have very little memory of the encounter either if she'd stopped right there.

Instead, with all the frustration, angst and primal want boiling just beneath the surface of her wounded psyche, whatever it was that the young man was providing was the salve she needed at that moment. If Chris was telling her to tuck her hand between her legs, she was helpless to comply. And the instant she did, her dazed eyes lit up like Roman Candles.

Chris' cock seemed to flare even more in his hand when he saw Jacki's reaction. It hadn't been the first time he'd played this little game with a woman online, but Jacqueline Montero was by far the prettiest, and that sent an extra jolt of adrenaline through his raging loins. The sheer thought of a woman that attractive and polished by day, wantonly digging her hand at her crotch as she stared at his manhood caused him to swell with virile pride.

"Now pull it out," he told her, easing his eyes forward so he could see the glistening sheen on her fingers.

Stroking his mammoth cock as he waited for Jacki to open her hand for the camera, he could tell by the way she rubbed her fingertips together just how slick they were. When she finally did expose her palm for the cam, Chris nodded his head approvingly.

Satisfied, he then told Jacki she could bury her hand back down between her thighs.

"Your nipples look like two bullets poking through," he unabashedly told the older woman a few breaths later, causing her to squirm that much more in her seat as she fell under his spell.

"Gawwwwddd...fucckkkk," Jacki gasped once she started fondling herself again, clearly showing all her defenses, moral and otherwise, had been breached.

"You've never fucked anything like this, have you?" Chris taunted in a hauntingly calm and cavalier tone, loving the way Jacki closed her eyes and nodded her head in agreement as she slide lower in the seat.

It wasn't just Chris' beastly penis that was turning Jacki inside out in front of the computer. While it certainly did play a part, seeing the youthful ripple of his abs as he held his shirt up sent bee stings down Jacki's spine as she juxtaposed all that with the image of the young man's handsome face. Even something as subtle as the soft blonde wisps of pubic hair lining the base of his ample shaft visually stirred feelings inside Jacki she didn't even know she had.

She also couldn't deny the way he talked to her had also somehow set her on fire. How he could be so crude, yet so polite in the way he stood there with his cock swinging free, as if openly savoring the weakness, need and yes, desperation she'd shown. Combine that with the lack of physical and emotional gratification in her life, not to mention her current lack of sobriety, and all the ingredients were there for a Biblical meltdown.