Principally Speaking Ch. 01

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Shy older woman's life is derailed by an Internet discovery.
6.3k words
4.24
72.8k
31

Part 1 of the 2 part series

Updated 10/28/2022
Created 09/19/2011
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Even the brightest, and most task oriented among us, can occasionally be consumed by digital quicksand. Forty-seven year old Dinah Lebowitz didn't have many bad habits, but losing hours of sleep late at night on the internet had become one of them. Bathed in the hazy blue light radiating from her computer screen beside her bed, time often seemed to bend.

What usually started out innocently enough, answering some email and checking on the minutes of the latest school board meeting, more times than not devolved into surfing through silly websites, downloading old tv shows, and worst of all, checking the inboxes of the handful of profiles she had up at online dating sites.

Having never married, Dinah constantly fended off the image of being the old, unmarried spinster. She'd got a job teaching right out of college, but after a few years of dealing with unruly 9th graders, she knew it was time for something more. Working on her Masters Degree at night, Dinah eventually secured it then landed a job as an assistant principal at a high school just outside San Jose. When her boss there moved on, Dinah had impressed the right people and was promoted to the big chair at age 39. It took a few years toiling as principal for Dinah to seek an even higher post, and a few weeks before her 45th birthday, she'd won a seat on the local school board, where she still proudly served.

Even though there were degrees and commendations of every sort covering the walls of her house, a house, by the way, she owned free and clear, those lonely, late night meanderings online proved there was something missing in Dinah's life, even if she truly hadn't allowed herself to face it.

Sad to say, the thought of a steady boyfriend rankled Dinah. The very idea of getting married scared her to death. While she had dated quite a bit in her 20's, and even had a few relationships that lasted over a year, nothing had really blossomed into more. By the time she was in her 30's and started her climb up the career ladder, her time, energy and capacity for dealing with bullshit had become sorely limited.

Once she'd been promoted to principal of her high school, between all the baggage the available men brought, combined with the insecurity many of them exhibited being with a woman of her accomplishments, Dinah found dating in her 40's was no strawberry field either.

For whatever reason, Dinah thought she might still stumble upon a diamond in the rough online. It was less embarrassing than having someone you know try fixing you up, and it was far safer and less time consuming as making herself up and dragging herself out to a bar. While she did attend her fair share of social gatherings through her position in the community, the last thing Dinah wanted was putting herself out there, only to get her heart squashed, or all her dirty laundry aired, by someone she had a professional relationship with.

Having made her bones as a math teacher, Dinah had always been a big fan of statistical reasoning. In an area as populated as the one she lived, she knew there had to be a significant number of attractive, single guys out there who had their lives together who she could spend some of her limited, but valuable, free time with.

The fact that Dinah refused to post a picture on any of her profiles certainly hampered the cause. Even if she'd posted the most benign, G-rated pic she could find, she would have increased the traffic viewing her profiles tenfold. Still, Dinah just couldn't bring herself to post one, knowing she'd be embarrassed to no end if someone from her circle of friends or colleagues stumbled across it.

Instead, Dinah was content to lie in the weeds, scoping out any potential match, then woo the guy when/if the opportunity presented itself. Little did Dinah know just how dangerous taking even such a cautious tact could be.

Judgment, even sober judgment, often doesn't function quite as well at 2 AM as it does at 2 in the afternoon.

Dinah had given the paysites like E-Harmony a shot, but it had essentially been money down the drain. She discovered she could meet the same litany of losers on the free sites out there. By not having a picture on her profile, she was able to sift through the cesspool with relative anonymity. If someone saw that she'd looked at their ad, at least they didn't have a face to go by. No picture = Plausible stealth.

Sort of like a woman surveying the menu of a restaurant she'd never dined, she could study the options for as long as she wanted before making a choice. That said, Dinah was hypocrite enough to curse all the guys out there that didn't post pictures of their own.

When a guy would contact her, or on the rare occasion where she made the first move, invariably his first question would always be, "Why don't you have a picture posted?", followed quickly by, "Can you send one?"

If Dinah thought there was some chemistry there, she would say 'she was just shy' and forward the guy one. If she didn't sense a potential connection, she could say something along the lines of "I don't photograph well" then drift politely off into the woodwork.

Of the guys who did post a picture, many of the photograph choices left Dinah at a loss. Whether it was a guy hiding behind a pair of sunglasses, or visibly drunk with his arm around another woman in a bar, or her all time favorite, the guy standing proudly in front of his mud-soaked pick-up with the carcass of a fresh kill slung across the hood, she developed a keen idea why many of these men had problems finding a date. Of the ones who actually seemed attractive and somewhat inviting, she learned real quick most of them were either married, or had some sort of mental defect, evidenced by the one guy who offered Dinah a chance to join him on an Aruban vacation before he even knew her name.

>From a purely comical standpoint, Dinah was stunned by the never ending array of men who posted cellphone pictures of themselves standing in front of bathroom mirrors with their shirts off, often times with other items of clothing missing as well.

While most of the sites didn't allow nudity on their profiles, it didn't stop a rouge guy every now and then from doing it anyway. Most of the time someone would report the profile and it would be deleted in short order, but as the evening wore on, it didn't take long before another two or three would pop up in its place.

Even though she'd never been married, Dinah knew what a penis looked like. Some were longer than others, some fatter, some thinner, and to Dinah's ever lasting amusement, some even vaguely looked like the men they were attached to. Some she even felt sorry for if it was true what they said about the camera actually 'adding' size.

Granted there were a few she saw that looked like the guy should be working in porn, but more times than not, if it was an especially impressive picture of the guy's junk, it had been lifted from somewhere else on the net. Since she'd been online, there was one specific picture that had shown up on easily a half a dozen different profiles.

Of course, there was also the handful of men who insisted on talking their beefcake photo in front of their bathroom mirror. And of course, there was nothing more alluring than a man standing there with his pee-pee out for the whole world to see right next to a toilet seat that was up.

Very few actually had a clear view of the guy's face, so when it did, Dinah couldn't help peeking a little longer, the guilty pleasure of seeing if she'd ever encountered the gentleman in question out in public.

When one of those thumbnails of a guy showing off his wares would pop up on the periphery of her screen while she was surfing the site, Dinah would normally just ignore it. On the rare occasion she was bored, or the image seemed somehow out of the ordinary, curiosity would get the best of her. Usually a healthy dose of bewilderment or amusement would ensue, then she'd just go on her merry way.

At 2:32am, one morning in early August, Dinah Lebowitz was overcome with a very different reaction when she gave into her morbid temptations.

Dinah had been finishing up a reply to one of the men she'd met at the site.

"A nice Jewish boy," her mother would have been pleased to hear, but given the guy was twice divorced and had a ton of back child support hanging over his head, he wasn't exactly the type Dinah intended to hitch her wagon to. Just after hitting the send button, the screen refreshed with a listing of the men who were online at that ungodly hour within a 50 mile radius.

"Oh...there's one," Dinah mumbled out loud, seeing the unmistakable outline of a bathroom mirror, the flash of a camera and a guy standing with his hand down at his crotch, holding his exposed manhood like it was Excalibur.

The guy she'd sent the email to wanted her to stay up a little longer and IM with him, but Dinah was ready to call it a night. After politely turning down his invite, Dinah shook the sleep out of her eyes a couple times before clicking on the tiny picture beckoning on the screen.

"One last laugh before bed," she told herself.

"MY GOD," were the next words out of Dinah's mouth when that tiny thumbnail transformed into a full sized ad before her eyes.

The guy in the profile was black.

For a progressive woman raised in a liberal, Bay Area family, Dinah liked to tell herself the color of the guy she was leering at didn't matter. In the year or so she'd been at that particular site, she'd seen men of every racial demographic swinging their joint for the whole world to see. To say that seeing that enormous slab of ebony flesh jutting out from the man's jeans, and hanging over that bathroom sink like imposing club didn't have an effect on Dinah would have been a lie.

Before she could soak in the full detail of the picture, Dinah had ever so subtly shifted forward in her desk chair as the cushion below began to smolder. Like most of the other X-rated bathroom shots, it was next to impossible to make out the photographer's face, and the information accompanying the profile wasn't much help either.

The guy did say he was 27, and his synopsis was short and sweet. "Aggressive black male looking for steady hook-up. Age, race and weight don't matter. Creativity, imagination and endurance do!!"

Dinah cringed seeing the cheesy profile handle he'd chosen, "Soulstroker12", but not enough to peel her eyes away from the photo which seemed the breath with life the longer she looked at it.

"No...you're not going to do this again..just flip off the computer and go to bed," a voice of exasperation chided inside Dinah's swimming head.

Given the late hour, and the butterflies suddenly stirring in places she'd rather not mention, Dinah Lebowitz had no problem ignoring that stern, but apparently toothless, admonition.

That voice in Dinah's head had seen this movie before. Not a lot, but enough to know how the next few minutes would likely play out. With her right hand still perched above the keyboard, Dinah's left drifted beneath the desk, disappearing like a thief in the night.

Unless you were standing right beside her in the dark, you wouldn't have had a clue what she was doing until you saw the telltale motion of her left elbow wrenching up and down, working like a rig drilling for something buried deep below the ground. If you moved in even closer, you would have seen Dinah's lower lip quiver as her glassy eyes continued their graphic study of the stunningly virile display of genitalia in front of her. If you were quiet enough, you would have also heard the way Dinah's bare feet spread on the floor just before the faint echo of friction meeting moisture.

"Like a thirsty cat lapping from a bowl," you'd conclude before catching your first whiff of her musky arousal.

It wasn't that she wanted to have sex with the man on the screen. She harbored no such feelings for any of the men she'd guiltily peeped at over the past few months. They were simply eye candy to ingest as she absolved herself, at least temporarily, of her selfish and wanton need.

In a strange way, the fact that she couldn't see the guy's face made what Dinah was doing that much easier. She could completely detach herself from any emotion and focus solely on objectifying that one element of the man's existence she needed to satiate the one gaping void in hers.

The spellbinding visual she'd created in her mind of her pale hands wrapped around the black phallus it's possessor was seemingly taunting her with stirred the silt from the depths of Dinah's long repressed desire. By the time she'd progressed to picturing that same shank of manhood pistoning between her parted thighs, Dinah was rocking back and forth in her chair, her moans increasing in volume as she neared release.

"Top shelf of your night stand, Dinah, there's still time," a voice far less scrupulous than the first tried to remind, but she was already too far gone to care.

Within three minutes of shoving her left hand down the front of the gray sweatshorts she often wore to bed, Dinah Lebowitz was lurching and heaving in her chair, her body bathed in the surreal glow of the computer as her cries of orgasm shattered through her spacious house.

When it was over, Dinah carefully pulled her hand from the syrupy mire of her crotch and pulled herself from the chair. Making her way on rickety knees to the bathroom, Dinah cleansed the evidence of her indiscretion down the sink without even attempting to look at herself in the mirror.

Before crawling into bed, Dinah walked back over to her computer to switch it off for the night. The same picture she'd just masturbated to still glaring, as if in 3D on the screen, Dinah bookmarked the profile then hit exit.

__________________________________

By the time dawn rolled around the following morning, the memory of how she'd finished off the previous night was a distant afterthought. Dinah went through the following week so occupied by work and other distractions that she hardly even logged on to her computer before bed. Like most clueless criminals that wind up getting busted however, Dinah eventually made the mistake of returning to the scene of her original sin.

If she just hadn't bookmarked that damn profile. Very rarely did Dinah ever go through the trouble of doing so. Either the profile would show up again at some point, and if it didn't there were thousands more out there just like it. In the case of the risqué ones such as the one she'd pleasured herself to a week before, more times than not someone either had reported the violation and the webmaster axed it, or the guy behind it simply took it down.

Logging into the site, Dinah absently clicked on the bookmark page. The 20 or so profiles she'd saved all materialized on the screen. Scrolling down the list, Dinah's heart skipped when the name Soulstroker12 popped up. Unfortunately there wasn't a thumbnail of him standing exposed in front of a mirror. The reality was far worse.

__________________________________

Whatever Dinah was expecting when she clicked on her bookmarks, seeing the face of someone she knew staring back wasn't one of them. It took awhile for all those assorted bytes of data to register, but once the puzzle started coming together, Dinah melted in her seat.

"Can't be....," she mouthed, but the dark rugged eyes staring back seemed to say "Sure is...".

Before landing the spot on the school board, Dinah had been principal at one of the area high schools, and the face in front of her belonged to one of her former students, one that had caused her a great deal of aggravation during his stay there.

Carlton Kinney was now 27, and hadn't given Principal Lebowitz a second thought since he'd dropped out of school nearly a decade earlier. Now he was, in a roundabout way, locked in a staring contest with the same woman that had suspended him more than once.

Just to be sure, Dinah mustered every bit of energy she could to click her mouse and change the thumbnail of Carlton to the full sized ad. She nearly slid right out of her chair when his unmistakable face splashed across the screen.

Dinah felt like a defenseless boxer taking a 12th round pounding as implication after implication of what she'd done hit home. Shaking her head, even rubbing her eyes several times, in hopes the picture in front of her would somehow change, Carlton's eyes seemed to narrow accusingly on the screen, twisting Dinah's intestines into knots.

"Only way out of this is hit delete and move on," Dinah's inner rational offered with laser clarity, but the powers of compartmentalization she'd developed over the years were suddenly neutered.

Before she could help it, a deluge of memories flooded back of the times she had Carlton in her office, and how many times she'd handed out a day or two of detention, knowing at some point he'd be sitting there on the opposite side of her desk once again. The memory of those interactions was further complicated when Dinah was forced to admit to herself why she'd gone back to the website that night, and the specific picture she'd bookmarked.

"I just need to get up..pace around for a few minutes..maybe mix a stiff drink," she rambled, but the instant she stood up, dizziness forced Dinah back down into her now broiling seat.

Again, the clear decision was to cut her losses, take her medicine and get the hell out of Dodge.

"The only person in the whole world who knows what you did, is you!!" Dinah reminded herself, but like a child who just can't resist tugging at a loose thread of her sweater, Dinah just kept picking and picking.

There was a gnawing need to know if he'd noticed that she'd clicked on his profile and returned the favor. Not that he would have had a clue who she was. Dinah had no picture posted, and the only allusion she'd made to working in the educational field was listing public administration as her occupation.

Steadying herself with an air of defiance, Dinah sat up straight in her chair and clicked on the icon that showed who'd checked out her profile. She quickly slunk back down when she saw Carlton had.

"OK..so he knows some random, faceless woman saw his profile. I'm sure he sees 100 of them a night until he trolls on something interesting," Dinah tried convincing herself, but the invisible reigns bridling her will continued to tighten.

"A few minutes after Midnight," she noted with the same reflection of a vampire might estimating how long til dawn.

There was a school board meeting the following evening at 7, and Dinah had a ton of stuff to do beforehand. The last thing she needed was staying up all night playing on the computer. Still, the aura radiating from the screen held sway.

"Maybe he only puts that picture up, here or there, to get a response, then replaces it with this one," Dinah theorized, her gift for rationalization working overtime as she vacillated on the tip of a very sharp sabre.

Facially, from Dinah's memory, Carlton had barely changed. From the looks of his G-rated picture however, he'd bulked up considerably in his upper body. A result of the weightlifting hobby he'd picked up during the four year stint in prison he served in his early 20's.

On every rational level, Dinah knew this wasn't the same kid who'd repeatedly sat across from her when she was assistant principal in charge of discipline a decade earlier. He was an adult now, and like thousands of other guys just like him had an ad posted on an internet hook-up site. The same site she, sadly, also had one posted.

"Stuff like this is bound to happen," she tried soothing her malignant worry, but the floodgates had already been opened.

Drifting through some of the other profiles she'd bookmarked, trying to find a desirable diversion, Dinah repeatedly found herself returning to Carlton's profile to see if the current picture had changed.

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