Entering The Rabbit Hole

Chapter Two

When I first arrived in Cape Town just over a decade ago, I managed to secure an apartment a brief distance from my offices. I took a train to work every morning but took a 45-minute stroll back home every evening.

It could have been a 30-minute walk if I wanted it to be, but there was nothing and nobody to rush home to. I also enjoyed the regular walks home because I always imagined they kept me healthy and helped lend some perspective.

It seems extraordinary that Aunty Mavis never cropped up in my thoughts in all that time of deep introspection. Nor did Misses Hulley, De Waal, or Davidson, for that matter.

That part of my life was well and truly behind me, but unbeknownst to me, a more terrifying beast was lurking, waiting patiently for the right moment to surface.

Some days, I worked well into the night, and every night, without fail, I bumped into the same set of young women on the way home. Some stood at intersections, others strolled around the block, and there were those who seemed permanently perched at the local bus stops.

I never picked up on the pattern for several weeks, and even then, it had to be spelled out for me. I was so naive that I used to greet the girls every evening before the great revelation.

Oh, to be innocent again!

One night in particular, I burnt the midnight oil with a colleague, who offered to drive me home afterward. On the journey home, I noticed a woman I had never seen before, who wore excessive make-up, an exceedingly short skirt, and a wide open top.

“Wow, that girl is dressed like a prostitute,” I remarked, having only seen this sort of thing on the tube.

“That’s because she is; they all are,” Gareth replied.

“What do you mean?”

“All the girls on this stretch of road are on the clock.”

“All of them? Holy shit, and everybody living in these apartments knows this?”

“Dude, how could you not know?”

“I’m a small-town boy.”

“Clearly. I feel sorry for these girls, you know. I can’t even begin to imagine how **** they must be to pursue this line of work. It’s an enormous sacrifice to make.”

I stayed silent, primarily because I had nothing meaningful to add but also because I was now doing my own calculations. I had never slept with a woman before.

In a world where all my peers had featured in some or other rumor about a girl crushing on them, I always felt like the exception that made the rule. Nobody loves me, I always thought, but I could now pay for somebody to act like they did, even if it were just for 60 minutes.

The women of Claremont Main Road had just opened me up to a world of fresh opportunities, a journey of discovery. Yes, it would come at a fee, but most women did anyway. A glass of wine here, a romantic dinner there...and no guarantees.

Access and the removal of rejection from the equation made the women of Claremont Main Road unique. I had never known what that would look or feel like, so this was uncharted territory.

Naturally, I felt guilty about it, which is why I remained hesitant for several weeks, but there was definitely some planning going on. I had played the scenarios over in my head time and time again.

How did all of this work?

Did one just walk up to the girl?

Was there some kind of code?

Did I send over some kind of signal?

Was any of this even legal?

I needed to do some extensive research beyond a few episodes of Miami Vice but had no idea how to go about it. This was more daunting than anything I had ever done.

This fresh assignment was my Everest.

It got to a point where I was even volunteering to work all the late shifts at the office just so I could walk past the Claremont prostitutes every night, and with every trip home, I made mental notes.

Previously, I had never really paid any attention to how they all looked; all that mattered to me was that they were available, but now I needed a few more questions answered.

Did any of them look too young?

Did any of them look malnourished?

Did any of them look trafficked?

How do you spot somebody with an STD?

Which ones were the most attractive?

Which ones were the most approachable?

After weeks of internal deliberation, I decided the time had finally come to take the plunge. I had picked my target; astonishingly, she wasn’t a middle-aged coloured woman. Aunty Mavis was a distant memory; this felt like progress.

The chosen one this time was slim, black, and pretty young. I estimated she was a year or two younger than me, so she was of age.

She had neat, relaxed hair - I think the local stylists called it a straight back - and she didn’t overdo the make-up, which I appreciated more than anything else. I would have preferred it if she wore no make-up at all.

I thought she was a genuinely pretty girl who could quite easily have passed for a Pastor’s daughter. She had a pleasant smile, too, and that is probably what did it for me in the end.

All of this made her seem the most approachable of the group.

It didn’t hurt that she was also regularly stationed at the intersection closest to my apartment block, making her literally the last girl I saw before entering my home. The intersection was also in a slightly more secluded area, which allowed for a little more discretion. That helped eliminate any fears I might have had about encountering some form of law enforcement.

She wasn’t the most breath-taking of the girls, but she was the most practical, and that was good enough for me.

As I finally approached her on my way home, I slowed down a little and glanced in her direction. Not a word was exchanged as I simply tilted my head slightly to the left, indicating that she should follow me.

She didn’t respond immediately, which sparked a little anxiety. But after about 30 seconds, I heard the distinct crackling sound of high heels against the tarmac, which was a tremendous relief, as I didn’t want to have to look back and signal again.

I had always wanted her to follow at a safe distance to help curb any suspicions but had no idea how to indicate that. In the end it didn’t matter because she understood exactly what I needed; a seasoned pro at just 19 or 20, which should be a little depressing when you think about it.

But any guilt I might have felt was quickly eroded. She was of age, and it's not like I was one of those dodgy university professors who thought it appropriate to shag their students.

Thankfully, my apartment was on the ground floor and closest to the gate. I opened the gate with my remote and let it run all the way open, which would give my new female acquaintance enough time to make it through before the gate closed.

The distance between us remained the same throughout.

When I entered my apartment, I left the door slightly ajar with the main light on, and she knew exactly what to do. I didn’t even need to stand at the door to offer some level of assurance. This entire adventure had already been so enthralling, and I looked forward to what would come.

While still fixing a drink in the kitchen, I heard my main door shut. So seamless, I thought to myself.

“I never thought this day would come,” she said.

“Whatever do you mean?”

“I thought you were disgusted by me, by the work that I do.”

“What made you think that?” I inquired as I gingerly handed her a drink.

“All the girls talk about you, you know. And all I ever heard from them was how you smiled at them politely and greeted them every night you walked past. I don’t remember being afforded that courtesy. If anything, you looked at me with disgust. I was pretty ashamed, you know.”

“Please accept my apologies. That was never my intention.”

I couldn’t remember if I treated her any differently from the other girls, and didn’t want to make a meal of things by arguing the point.

Upon reflection, I do think hers was a fascinating observation, though, as it exposed, even back then, my apparent bias against black women. It is an issue I certainly need to confront, possibly with the help of a professional, at some point.

“Do you work somewhere around here?”

“Yeah, near Claremont Station.”

“And what kind of work keeps you at the office late at night.”

“Content syndication. We have a lot of Asian and North American clients. I am not actually required to work late every night, though. I volunteered. Don’t have much of a social life anyway. Are you a student?”

“Depends…”

“On what?”

“Would you be fine sleeping with a student?”

“I suppose it wouldn’t matter. I was just a little curious. I recently read a book called Disgrace by JM Coetzee, where similar circumstances confront the main character. I am a little worried that I might be wandering down the same dark alley.”

“Well, for starters, you aren’t a university professor, and I am not your student.””

“But you are a student?”

“How do you draw that conclusion?”

“You read JM Coetzee. That stuff is not for everybody. It is the kind of thing a student would read.”

“Maybe I just watched the movie."

"I pity you. It was a genuinely dreadful piece of cinema. I wouldn't watch it again if you paid me."

"Please don’t feel guilty. This is my job, and you are my client. Nobody is exploiting anyone here.”

The moment she said it, she flicked the light switch and seemed to glide across the floor before grabbing my arm. She walked towards my bedroom, and I followed like the obedient puppy that I was.

“Relax,” she whispered in my ear, almost as if she could sense this was my first time.

She gently removed my sweater and undid the buttons of my shirt before going down on her knees and unzipping my trousers, pulling them down with my trunks at once. She seemed to be in a hurry.

And in that moment, nervous as I was, I recalled Chris Rock’s joke about fellatio. This would be the ultimate test, I thought, before letting out a slight chuckle.

“Tickled already,” she whispered as she quickly went to work on me. I let out one huge breath and closed my eyes. This was it. There are simply no words to describe the ecstasy I felt in that moment.

I would have absolutely no control over how this would play out, but she was prepared, as she released me in what seemed to be just the nick of time.

Suffice it to say, I ejaculated violently, and she emerged completely unscathed by it all.

“Did you enjoy that,” she asked, but I couldn’t muster a response of any kind. The entire experience had sapped me completely.

“Good,” she added. She thought she had me just where she needed me now.

“That will be R800.”

“What?”

That certainly sobered me up.

“My services are R800.”

“For a blowjob?” I cried. The miser in me came to the surface faster than she could have imagined.

“You ejaculated.”

A brief silence followed, and perhaps sensing that this might not end well, she said she would throw in the sex "for free". I took the deal but swore to myself this would never happen again. I felt swindled, the kind of feeling you get when you walk out of a casino for the first time.

Whatever my sexual curiosities were, this hardly felt worth it. I was genuinely incensed by it all.

Now I know, I thought to myself, but unbeknownst to me, I would write several new chapters on this journey in the coming weeks and months.

The “Lady in The Red Shoes” - I never bothered to remember her name - was just the beginning.

***

In the immediate aftermath of my disastrous encounter with the "Lady in The Red Shoes", I requested fewer evening shifts at work, and when I did find myself burning the midnight oil, I opted for a new route back home.

Upon reflection, it was obviously ridiculous that I felt compelled to alter my movement patterns just to avoid a street whore, but them's the breaks. In subsequent years I have openly regaled others with tales of my sordid past, but I have never uttered a word about the "Lady in the Red Shoes" to another soul.

I was certainly embarrassed by the manner in which events played out that night, but I couldn't possibly tell you why I was so determined to wipe the entire episode from my memory.

Nevertheless, it was not long before opportunities to pursue more conventional and sanitary courting methods presented themselves when a dish called Candice joined the editorial team at work.

Everything about Candice made considerably more sense to me than the "Lady in the Red Shoes'', apart from her being distinctly out of my league of course. There was never a hope in hell there, but I always liked to think there was.

Candice was older than me and was coloured, but getting her to fall for my non-existent Zulu charms would be nothing short of a miracle. Minor details like these have never been enough to stop me from abandoning all judgment in the past, though.

The lunacy started and, thankfully, ended with an email. Throughout my engagement with Candice, I never mustered the courage to walk up to her desk, which was just two meters away from mine.

Now that I think about it, I didn't even need to get up and approach her, as I could quite easily have initiated a verbal exchange from my workstation without unduly interrupting other colleagues or, indeed, embarrassing Candice.

Candice and I corresponded regularly for about a year when I learned a lot about her. She was astonishingly open and trusting about every aspect of her life, but that was perhaps as sure a sign as any that I had unwittingly stumbled into the dreaded friend zone.

That's what I try to tell myself anyway. But in truth, I simply never mustered the courage to make any significant advances, and for all I know, Candice was patiently waiting for me to show some pluck.

Suffice it to say, the Candice opportunity was wasted, and we were nothing more than pen pals.

When I wasn't at work, I could be found making love to my whiskey and gin at a local watering hole called Hobnobs, just around the block from my apartment. Hobnobs were convenient, but there was nothing particularly compelling about the joint.

The place was an old house that had been converted into a pub, one might even say a typically English pub. Beyond booze, the specialty in this neck of the woods was bangers and mash; as it turns out, bangers and mash would become my dinner at least five times a week for about a year.

While Hobnobs had clearly become a second home to me, I never took the time to mind my surroundings. It might have been a public facility, but it had also become a place of solitude, where I could just stare blankly at the sport on the big screen or listen to AC/DC blaring in the background.

One evening, in particular, I was awakened from my trance though, when two young coloured women walked into the venue. This might have been Cape Town, but two coloured women walking into Hobnobs was unusual; in fact, I would go so far as to say I had never seen a coloured woman in the place before.

They both found seats in my direct line of sight, distracting me from what was a compelling game of Super rugby. While I was incapable of taking the plunge and making any meaningful advances, I did eventually ask one of the waiters to give the women another of whatever it was they were drinking.

But I didn't so much as glance in their direction when the drinks were delivered, having decided that the Sharks driving maul against the Bulls was too great a thing of beauty to be ignored.

Granted, I never actually knew what the protocol was when buying women's drinks, but I was also too terrified to find out, and far more comfortable watching 30 grown men chase after an oval ball for a living.

When it became increasingly apparent that the girls were about to leave, I decided to disappear into the pub bathroom and stay there for as long as I thought would be necessary to avoid any contact with them. When I returned, both girls were thankfully gone, and it did occur to me that perhaps they were also grateful they never had to bump into me on their way out either.

What a mess!

I wanted something conventional and pure but wasn't adequately equipped to pursue it, not in Cape Town, anyway.