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David’s Dilemma: Part One

"Ethical Hacker loses his morals."

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Author's Notes

"Places are real. People are fictional. Hope you enjoy. There are two more parts."

My name is David. Originally, I am from Gardenstown, a small village in the north east of Scotland. I loved growing up there, having adventures in the countryside and jumping off the harbour into the water. At home, I enjoyed spending time on my computer, learning how to code.

As I grew up, my thirst for adventure was always there. I went dirt biking, sea kayaking, and horse riding. Anything that involved a bit of risk and danger was always at the top of my agenda. A few broken bones didn’t put me off anything. As school life was coming to an end, I decided that combining my passion for adventure and computing into a career would be best. So, I signed up for the Royal Air Force. In my head, I was going to be on missions, pretending to be James Bond. It turns out Computer Analysts spend a lot of time in darkened, windowless rooms.

After serving five years in the Royal Air Force, I managed to get a job within the Ministry of Defence. There I felt like I was living on the edge a bit more. Never on the front line but always nearby offering technical support, creating some gadgets like Q. Some of those creations remained in my possession after I left. Fortunately I got to visit many countries but sadly not as a tourist, I was often hidden away whilst the agent got all the fun.

I decided that I needed a change. I knew I had some time to kill before I could officially leave, so I furthered my skills with some in-house courses. The coding skills I had developed as a young man translated naturally with cybersecurity, especially with ethical hacking. Ethical hacking involves working with individuals or companies to make their websites and computer systems as secure as possible. In theory, I was mimicking cybercriminals.

My time serving the government through the RAF and MoD had come to an end, and the next step in my life lay ahead of me. I had managed to save a lot whilst living away from home. Not having a girlfriend helped. It didn’t stop me having one-night stands or friends with benefits, but I was single. Fuck, one of my friends with benefits was my superior’s wife. She loved the thrill of nearly getting caught. My boss had no idea she was under my desk sucking my cock as he was boasting of his extra-marital affairs. There was one woman in the office that I wanted to get with but she, Ella, always rejected my advances. Turns out she wasn’t impressed with my reputation. That was frustrating but Ella and I always remained friendly. I was never insubordinate but enjoyed pushing boundaries, after all boundaries are there to be pushed.

After living away from home, I decided it was best to return to Gardenstown. The village hadn’t changed much since I left. The bakery was no longer there, but that was the only noticeable change. My parents had moved along the coast to Portsoy, so they were still nearby. I managed to rent a nice cottage with a sea view. Now I was settled, it was time to offer my services to the local businesses.

I spent my mornings watching the waves crash against the rocks while emailing local businesses. Some were interested in my services; others had no idea what ethical hacking involved, so those email chains took a little longer to explain. Business wasn’t exactly booming, but it was a good start.

Slowly, I was building a positive reputation within the local business community. Soon I was receiving emails from companies looking for help. I got to travel around parts of Scotland because I always tried to meet my clients in person to build trust. After all, I was trying to hack into their company legally.

Whenever I was away from home, I tried to spend a night in a hotel to avoid too many long drives. That led to many nights of meaningless hotel sex. Snapchat seemed to work best, especially if you wanted younger companions. I was nearly forty but loved having sex with women in their early twenties. Women my age were always a bit more challenging. I found it difficult to read their intentions.

I don’t think I ever wanted to settle down, apart from my parents’ relationship, every serious relationship I watched eventually became toxic. Sadly, I had lost a couple of friends due to their relationship breaking down. Their wives and girlfriends made them feel worthless and pathetic and they decided that life wasn’t worth it any more.

Every year, on the anniversary of their passing, I visit the site of their final breath. Each year, I will talk to their spirit wishing they reached out to me. It’s nearly the anniversary of my friend Scott’s death. One night, he leapt from the viaduct in Cullen. His body wasn’t noticed until the morning. I often think of the poor woman that found Scott’s body. No one should have to start their day in such a manner. Scott had met someone online that he was besotted with. Turned out Sandie was just using him as a placeholder until her abusive ex became available again. Sandie was truly heartless afterwards. She told Scott’s mum that if she had raised a strong man, he wouldn’t do something so cowardly. Resentment grew towards Sandi from that day. No one was shocked when her ex had left her again. Even he was disgusted with her callousness.

On one of my trips to Aberdeen, I met up with a previous client, John, who had started a new project. Since John was a repeat customer, I took him out for lunch before discussing how I could help secure his business. Over lunch, we got chatting about life. John knew about my carefree lifestyle, especially after my last visit ended with me sleeping with his secretary and his accounts manager. It turned out they had been giving me positive reviews to the other women in the office. He always asked about my latest sexual escapades, enjoying me sharing the finer details of my exploits.

John suddenly became quiet, as though he was trying to find the right words. I simply told him to spit it out. Sheepishly, he admitted that he believed his wife had been having an affair for quite some time. Every word upset him more than the last. John was worried that if he divorced her, she would take half of everything. He needed evidence before he could act.

Then he looked me in the eyes and asked me to help. He wondered if I could become an “unethical hacker” for him.

I asked him what he wanted.

“I need hard evidence—nothing circumstantial. I’ll give you all her details: phone number, email address, car registration, credit card details. If you need anything else, just ask. I need photos, videos, messages… anything, really. Leave no stone unturned. If I don’t get this, she could cost me up to £5 million in the divorce, and my business will be hers. I’ve worked too hard to be in this financial position. Can you help? I’ll make it worth your while.”

Pensively, I asked, “How will you make it worth my while?”

John opened his briefcase, took out an envelope, and slid it across the table.

“There’s £10,000 in the envelope. Get me the evidence, and you’ll get another £100,000. And after you get this job finished, I’ll recommend you to all my other business associates. Imagine the lifestyle you could live afterwards.”

Shocked by the proposition, I asked him to give me time to think about it. He agreed but asked for an answer within forty-eight hours.

We finished lunch and headed back to the office so I could carry out some cybersecurity tests. He had protected his company well. He had clearly spent a small fortune installing the best security available. I ran all my programs and not one penetrated his systems. What was more impressive was the detailed quality of the CCTV.

The ladies in the office were all happy to see me. There was some not-so-subtle flirting and the age-old trick of dropping a pen in front of my workstation. The accounts manager, Lisa, had already told me she would be working late if it took me longer to finish. Gemma, the secretary, was away on holiday with her boyfriend Rob. Didn’t stop Lisa messaging Gemma to tell her of my presence in the office. Gemma messaged back immediately to tell Lisa that she was jealous and wanted to be at work.

Obviously, I was going to take my time. Lisa was a great fuck the last time we met. She was a similar age to me but looked a good decade younger. She reminded me of Lucy Lawless from Xena: Warrior Princess. Tall, slender, exquisite body, with piercing green eyes and long dark hair. She was drop dead gorgeous. Lisa kept on approaching me during the afternoon. I didn’t think much of it as I was focussed on my work. Actually, my mind kept returning to John’s offer.

Everyone slowly left the office for the night. John was the last to leave. He looked up to see Lisa and me as the only two left in the office. As he walked out of the door, he told us to have fun and make sure we cleaned up. We all laughed as Lisa got up to lock the office door.

As the latch clicked shut, Lisa turned around slowly, her fingers already undoing the buttons of her blouse, exposing an emerald green bra. Lisa had clearly had her tits enhanced since the last time I had seen her. Her right hand reached behind her back to unhook her bra. I watched lustfully as she revealed her new tits, complete with barbells through her excited nipples.

I got up from my workstation and headed straight for Lisa. Our lips met with wanton lust. There was no emotional connection between us; we simply wanted to fuck.

Lisa told me we only had an hour because she was meeting her husband for a date. Well, he was picking her up from the office. We ripped off our remaining clothes. Foreplay was disregarded as we used her desk as the place to fuck. I eased my hardened eight-inch cock deep inside Lisa’s shaved pussy. She was already soaking wet. It turned out she’d been wearing her Lovense Mini all day after hearing I was visiting the office.

Lisa had been edging herself all day, desperate to be filled with cock. Her groans grew louder as I increased my rhythm. Thrusting hard, Lisa began to squirt, followed by a powerful orgasm that filled the room with her cries of pleasure. She demanded that I didn’t stop.

Determined to make her climax again, I thrust my cock as deeply as I could. Lisa pulled on her pierced nipples, heightening her arousal. I continued pounding away, the sound of our thighs colliding echoing throughout the office. I felt my cock tighten, ready to explode. Lisa’s groans became even louder as another orgasm approached. The gush from her pussy seemed to invite my release. Repeated spurts of cum filled her.

I collapsed on top of Lisa as my cock could give no more. As it softened, it slipped out of her pussy, my cum dripping onto the floor.

Lisa didn’t bother cleaning herself up. She simply pulled on her underwear to absorb my cum. She smiled at the thought that her husband would unknowingly clean me off her later that evening after their date.

We tidied up as best we could, but the smell of sex still lingered in the office. One last kiss before we left, both of us hoping it wouldn’t be long before I was back in the office. I hope when John got home, he enjoyed the show Lisa and I put on. After all, I knew he had state of the art CCTV in his office.

Up the road I travelled, stopping in at the supermarket in Ellon to pick up something for dinner. My phone kept beeping with some females trying to grab my attention. Watching them playing with themselves was fun but my mind was on other things. Despite the offer of mindless fun, my mind was drifting back to John’s proposal. £100,000 for this job would set me up. I could almost buy a house for that. But what if he was wrong? All that work for nothing. Worst case scenario is that I have £10,000, that’s better than nothing.

That night, when I got home, I walked down to the harbour and sat on the bench, watching the waves crash against the harbour wall. The sound of the sea and wind always helped clear my mind. It was one of the reasons why I moved back home.

I took out my phone.

First, to see that Lisa’s date night was going well.

Then I messaged John.

“I’m in.”

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My phone buzzed.

“Excellent,” was John’s response. “We’ll speak more in the morning.”

I stayed at the harbour for a while longer, staring into the dark water as the endless Scottish summer reluctantly gave way to night. The weight of what I had just agreed to settled heavily on my shoulders. Doubt crept into my mind as I tried to work out exactly what I had signed up for. I already knew sleep wasn’t going to come easily.

I think I saw every hour of the night. My bedside clock seemed to mock me each time I glanced at it. Sleeping had never come naturally, but tonight was different. My mind refused to switch off. Even replaying my hour of passion with Lisa did nothing to distract me from the questions racing through my head.

As the first light slowly crept through the window, illuminating the edges of my curtains, I heard the local cockerel announcing the start of another day. Normally his morning call never bothered me, but this morning I could happily have strangled him.

Eventually, I dragged myself out of bed. The clock read 05:14.

While the laptop powered up, I made myself a coffee. Whatever happened with John, I still had a business to run. I couldn’t let his proposition consume every waking moment.

A couple of nearby secondary schools had emailed to ask whether I would visit and speak to their students about my work. Since one of them—Banff Academy—had been my old school, I gladly accepted the invitation. I held off replying to the other school for the moment, but I already knew my answer would be yes.

The coffee wasn’t having the desired effect, so I pulled on my running shoes. Hopefully a few miles would clear my head.

Deep down, though, I knew there wasn’t enough coffee or exercise in the world to quiet the question that had been keeping me awake all night.

What had I just agreed to?

Eventually, my phone buzzed. John had messaged me. “Meet me at Tarlair. Midday. Come alone!” The last instruction unsettled me. Why come alone? I was going to do that anyway. What exactly did John have planned?

I jumped into the shower, singing badly to whatever song was next on my playlist. It amazed me that my neighbours hadn’t reported me to the police—or at least the council—for noise pollution. Chappell Roan’s Pink Pony Club became the latest victim of my shower concert. For a few minutes, concerns about my meeting were out of my mind as I continued to miss all the high notes.

Despite being up for hours, it was still only 09:49. So, I completed a couple of smaller jobs and chased up an invoice that had still to be paid. Anna Cockburn, from Banff Academy, replied to my email, she was delighted that I replied so quickly. A couple of emails later, we had arranged a day for me to visit the school.

As I was concluding my emails with Anna, another message appeared in my inbox. It was from Lisa.

She was asking me to phone her as soon as possible.

Lisa rarely messaged me, so I was intrigued as to why she was contacting me. I called her immediately.

She answered quietly.

“Can you give me two minutes?”

Through the phone, I could hear her walking quickly before a door closed. Then her voice returned to its normal volume.

“Did you notice anything yesterday while you were running your programs?”

“No,” I replied. “The security system did exactly what it was supposed to do. Why?”

“John was in here first thing this morning, even before me. He looked like he hadn’t slept all night. John was always so smartly dressed, but today he was dishevelled. I’m sure he was still wearing the same clothes as yesterday. It was completely out of character for him. Then he left in a hurry about twenty minutes ago.”

I stayed silent on the phone.

If John had left twenty minutes ago, then he wasn’t heading straight to Tarlair. The timings didn’t make sense.

He was going somewhere else first.

I wondered if Lisa was fishing for information, so I remained tight-lipped about John’s proposal and our planned meeting. I enjoyed my time with Lisa, but I knew she could sometimes be too open with information. She wasn’t the person I wanted carrying a secret this important. After all, she had already proven she was capable of keeping secrets—her husband still had no idea about us.

Part of me wanted to believe she was simply concerned. Another part of me wondered whether there was more to her call.

For the first time that morning, I realised something.

I wasn’t just trying to work out what John wanted.

I was trying to work out who I could trust.

Time was now racing towards midday. I checked my watch and realised I now had 30 minutes to get along to Tarlair. Tarlair had been a special place for my parents’ generation. By the time I was old enough to remember it, the magic had faded. Recently, the art deco building had been converted into a cafe but the best days are behind them.

I wanted to be there early, as I didn’t want to keep John waiting. I grabbed my phone, laptop and car keys, as I headed out. The drive was uneventful. It usually took around 15 minutes. As I headed through the housing scheme, my phone began to lose its signal. Hopefully, that wasn’t a sign for what is going to happen.

The car park was fairly quiet, so I had my choice of parking spaces. I reversed into the parking space, an old habit from my time in the RAF. If I needed to leave quickly, I wouldn’t waste time manoeuvring out.

I said hello to a couple of old ladies leaving the cafe. They were telling me that the soup of the day was Roast Parsnip and was delicious. Despite Roast Parsnip being my favourite soup, I wasn’t in the mood for eating. Patiently, I waited for John’s arrival.

As the wind blew around the complex, I was getting nervous. It was now 12:14. John had never been late for any meeting with me. I heard a car coming down the road, it was John’s Porsche Cayenne. He loved that car and would wax lyrical about it. I would always smile and nod when he spoke about it as I wasn’t really a car guy.

I waited near the old swimming pool, just so I could observe everything around me. No one got out of the car for a couple of minutes. The driver’s door opened slowly. John stepped out, and instantly I knew Lisa had been right. He looked exhausted, his clothes creased and his appearance completely unlike the man I had met before. They were the same clothes he had been wearing yesterday.

Before leaving the Porsche, John grabbed an envelope. What caught my attention, though, wasn’t the envelope—it was his hands. They were black with grease and dirt but his clothing was clean of the grime. John walked up to me and apologised for his tardiness. “Fucking nightmare. Had a blow out just past the Cemetery”. John took a while to change the tyre. He said that he tried phoning but I wasn’t answering.

The cemetery was not that far away. You pass it as soon as you enter Macduff. The timing roughly matched. If he was lying, he’d thought the story through. It still didn’t explain why he left the office early though.

I asked John about his clothing choice. John and his wife, Sandra, had a massive argument last night. Sandra was moaning about John spending too much time at the office working. John couldn’t muster up a fight with Sandra, so decided to just go to the office to sleep. Lisa had woken him, as she was first in the office. I decided not to tell him Lisa had called. For now, I wanted to keep that piece of information to myself.

After what felt like an eternity, John handed me the A4 envelope. It was full of information for me to decipher. John had even given me a recent photo of Sandra as well. She was certainly an attractive woman, Sandra was a couple of years younger than John but she didn’t look like she was 53 years old. I thanked John for the information and told him that I would find out what I could as soon as I could.

John stressed that he needed information sooner rather than later. I pressed him on why he needed the information sooner rather than quickly. John refused to share why, I decided to take a stand that if he didn’t tell me, I would walk away. If I can be trusted to hack his wife, he should trust me with the reason why speed is of the essence.

“I can’t tell you.”

“Then I can’t help you.”

John stared out towards the sea.

“If this gets out…”

“John.”

He sighed.

He signalled with his head to go somewhere more private as the car park was filling up with cafe users. We walked towards the sea wall as no one was there.

“My company is about to launch something worth more money than I ever imagined.”

“We’ve developed something that changes everything,” he said quietly. “A stabilisation system for offshore platforms. It allows floating rigs to operate in water depths nobody thought commercially viable.”

“So?”

“So if it works, we’re not talking about millions.”

He looked at me.

He didn’t say it dramatically. There was no excitement in his voice. Only fear.

“We’re talking billions.”

“If Sandra divorces me now, she’ll walk away with a sizeable chunk of the company.”

“Didn’t you sign a prenup?”

“We did.”

“So what’s the problem?”

“If she’s unfaithful, the agreement protects me. If she’s not…” He shook his head. “Everything I’ve spent thirty years building could disappear.”

“Why don’t you get a Private Investigator to do this? Surely they are better suited than me?”

“Well, I have no reason not to trust you. I’ve paid you to hack my company and you have never done anything that would make me question your integrity. I know I’m asking you to do something illegal but I wouldn’t be doing this if I wasn’t desperate!”

“Right! Now I can help you.”

“I’ll start immediately. Don’t expect daily updates or question my methods. If you want results, trust my process.”

John looked relieved with my statements. He thanked me for agreeing to the proposition. John headed back towards his Porsche. I waited for him to leave before heading into the cafe. Obviously the Roast Parsnip soup was popular as they had sold out. Argh! I was looking forward to that.

I had spent years telling people the difference between ethical hacking and criminal behaviour was permission. That morning, sitting in my car with an envelope containing Sandra’s personal details, I realised how thin that line really was.

As I drive away from Tarlair, my phone lit up. There were two missed calls and a voicemail from John.

“David… if you’re already there, don’t leave. I really need this meeting.”

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Written by enkegee
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