It was mid july, the sun had been non stop out and blazing for several weeks, and me and my family had just began our trip down the coast to finally get a break from the buzzing, hecting big city.

I was nearly 18 years old at the time, and just like most my age I considered myself somewhat odd, nerdy but in a good way I suppose. My friends who I normally spent my time playing video games or doing borderline illegal fire cracker stunts with were (all three of them) out of town at the same time for the first time since school ended, meaning that the roadtrip mom and dad had planned actually came as quite a nice change from my growing teenage restlessness.

We had just finished the second long drive of our trip and were settling into a cosy hotel in the centre of a small beach town right next to a renowned wildlife reserve. My dad always took us hiking whenever we had the time, and I was actually somewhat excited this time, especially after spending many uncomfortable hours in the back seat of our old toyota trying to fold my long lanky legs into any position which momentarily allowed for a nap. I used to be able to sleep so easily in that car, but my last growth spurt really put a stick in the wheel of my comfort.

Now, when I say the town was small, that's in comparison to the huge smoggy city I normally lived in, but the place was hardly rural. It had lots of businesses, some taller buildings and a popular water front which tourists came travelling many miles to visit. The hotel was not luxurious by any means, but it had a nice hostel or bnb type of vibe, and accounted for only around a fifth of the apartment complex-looking building it was situated in. The rest was either rentals or office spaces, I'm not quite sure. We carried our bags in via the lobby and through a small courtyard which had a little pool with a fountain. Along the inner walls of the complex ran many levels of balconies and walkways with white stone arches and black cast iron handrails. I saw people walking around carrying laundry many floors up, which is how I realized that hotel guests were not the only residents. I didn't get too good of a look though, as we hustled to get our bags across and through the door on the opposite side where the hotel corridors lay.

Unfortunately, my sleep was cut rather short. Our room was nice, but the air conditioning was lacking leading to a very warm and humid night - something I didn't particularly like. I woke up around 1am, and after squirming in my sheets for another half hour, I figured there was no use. I quietly got up and put on my shorts and t-shirt, not that I could've done anything short of yelling to wake my parents at this hour. I couldn't exactly turn the TV on though, so after a moment I got the idea to have another look at the courtyard, and started making my way downstairs.

I expected the place to be quiet, but someone was actually playing music out their window a few floors up. I also heard voices, which suggested there was a party going on. There were no people in the yard though, I only heard footsteps on the walkways higher up every now and then, probably from people returning home after a saturday night out. Now I had a chance to really get a proper look at the place, and more importantly - get up to some mischief.

I didn't initially have the intention of doing anything adventurous, but the walkways really reminded me of the videogames I used to play back home. It would be so easy, I thought, to climb up the iron bars and railings and get access to the upper floors without even having a key. Of course I was not goin to risk my life trying this idea, but I was definitely gonna try something. The yard was not rectangular, but rather L-shaped, and in the curve of the L lay the pool. It just so happened that there was a walkway running between the innermost corners of that part, right above the pool water. Now, the pool was not for swimming - it had water lillies and stuff in it, but it wasn't concrete floor either, and all of the walkways were at least a couple of meters above ground. In my head this was the perfect challenge - there were even staircases in the the corners which led up to the walkway, conveniently sealed off with security gates to which I had no key. Using the side of one such staircase it would be quite easy to stand up and reach the edge of the marble walkway floor, between the iron bars of the handrail. Would I then be able to shimmy across safely to the other staircase?

I debated for a brief moment whether I should give in to my dumb plan or not, but I was honestly such a feral monkey at that age - it took me less than a minute to make my way over to the pool side. I had to hold on to the stone arch next to the staircase and balance on top of its handrail in order to reach the walkway, but even then there was still a tiny distance left. It surprised me, because it all looked so trivial from the ground, but then I gauged the distance, figured I'd gotten this far - and leapt. It was easy! I caught the edge with both hands, missing the bases of the iron bars with my fingers. The bars were quite widely spaced, so it wasn't exactly a problem. Also, the ledge was slightly curved upwards, so I could get a really good grip with my entire fingers over it. After stopping the swinging of my legs, I began shimmying sideways over the pool water. I didn't have any sort of plan for how to get down onto the handrail on the other side however, but this turned out not to matter.

I'd gotten about one third of the way when I suddenly heard a door open above me, and a voice talking, probably on the phone. I turned my head to the side and saw a woman coming out of the door next to the staircase I was headed for, in the direction of the walkway I was dangling from. I instantly stopped my sideways shuffle, hoping to avoid the awkward encounter by simply remaining unnoticed. I was out of luck however, as the woman only took a few before she looked in my direction, froze temporarily, and stopped talking on the phone. It was a girl in her mid twenties I'd say, and she was very attractive. Quite tall and curvy, tan skin and black hair. She was clearly dressed up - either coming home from a party or going to one - a strapless top together with a short ruffle skirt, and I could hear the distinct 'clop clop' of her heels right up until when she stopped.

"Fuck!" I thought. What if she mistook me for a burglar and caused a scene, or called the cops? I was not keen to explain yet another stunt to my parents, especially at 2 am in the morning. Thus, it was to my great relief that I then heard her voice continue:

"-Sorry there's just someone, ugh nevermind ANYWAY..."

She disappeared out of sight behind the handrail as she started walking across above me. At first I thought she might be going into some door in the wall, but when turning my head upwards I noticed her hand was lazily trailing along the handrail right above where I was hanging. Craning my neck, I didn't realize how stupid it must have looked from above - my dumb teenage brain was of course occupied by the thought that I might catch a glimpse up her skirt from this angle. I heard the phone conversation and the clop clop continue, saw her index finger drag thoughtlessly across the iron railing, and right when it was about to pass me - it stopped.

Keep in mind, this all happened in the span of about ten seconds. I was quite confused as to why the girl had made a halt right above my spot, but I didn't need to wonder all that long. I saw her hand turn and grab the railing right before her face appeared above it, still talking to her friend. I quickly faced down to avoid the awkward eye contact.

"-Wait, are you serious? Why would anyone care? Oh my god Ari this is..."

I felt a light prod against the fingertips of my left hand. It wasn't anything violent - she'd simply poked them with the pointy tip of her shoe to get my attention. I looked up again, to find her somewhat leaning on the railing, looking down at me with a neutral but slightly passive aggressive face. While listening to her friend's reply, she lifted her hand and gestured to get off while mouthing "shoo". I looked up at her confused and whispered:

"-What? I can't! I was just..."

She clearly didn't care, and kept on talking on the phone. I figured I should probably get going back to where I came from, since I'd been stopping for too long. I still had plenty of grip strength left though, and couldn't help but to catch another glance upwards. Now that the girl was standing up against the railing, I could see up her tanned, shaven legs. There was a tattoo on one of her thighs - couldn't quite make out what. It was probably because I was too busy staring at the crotch of her bright red lacy underwear. She didn't turn her head down again, but I'm pretty sure she glanced down the corner of her eye to catch me peeking. Not immediately shimmying back turned out to be my biggest mistake.

Mid-sentence, i noticed a shift in her posture, as she moved one of her feet forward. She was wearing black, strappy pumps with a pointy toe, a toe which briefly hovered above my left hand before settling down on my knuckles. Unlike the previous prod, this was quite uncomfortable. I felt my fingertips compress under the thin, hard sole of the shoe - even more so when she gracefully shifted more of her weight onto my hand. I grimaced in pain, holding back a desperate yelp to avoid unwanted attention. I barely had any time to react before the second foot moved forward as well, trapping both of my hands against the marble. Only then did I realize how screwed I was. The conversation continued, and my tormentor giggled at something said over the phone.

I tried pulling my right hand out from under her shoe, but she noticed and rocked just a bit forward on both feet. The increased pressure sent a shock of pain down both of my wrists, and made escaping completely unfeasible. Towering over me, she tilted her head a bit down again. She made eye contact, and her expression changed from stern annoyance into sarcastic amusement. She lifted her eyebrows, wrinkled her forehead and lifted her hand to her mouth - fake gasping like she was going "oops". I must have looked rather pathetic from her point of view, and that's how I felt as well. It was becoming increasingly difficult to hold on despite the angled ledge. At this point the pressure of her shoes were almost keeping me hanging rather than sending me falling. I looked down at the pool - it was quite shallow and the bottom looked slippery with something like algae. It wasn't an inviting landing area whatsoever. It was then I felt one of her feet lift from my fingers.

"Hold on I've just gotta... Let's see..."

This was my chance to move my hand and try to escape, but at this point I would most likely plummet if I tried hanging one handed, or so I thought. I looked up in horror to see the sole of her foot moving out further through the iron bars, hovering in mid air. The girl bit her lip concentrating while aiming her slender stiletto heel right between the knuckles at the base of my middle and ring finger. Her mouth opened wide in sadistic excitement while she began slowly pressing down. I braced for the pain, but nothing could have prepared me for the sheer piercing agony shooting through my right hand. And this was just the start. I gasped for air and gave her a pleading look. I half whispered:

"-Please!"

She did the "oops" face again, this time even more exaggerated than the first. Then I saw her teeth gleam in what can only be described as a malevolent grin, as she shook her head no. She was now starting to slowly rotate her foot left and right, grinding the heel down into my hand while still increasing the pressure. If she kept this up, I would have a fracture or even a hole punched straight through. She then told her friend:

"-Ari this is so fucked up, you have to see this!"

She turned her phone around and tapped the screen. I saw the light of her phone camera face right down towards me. I couldn't believe it - she was video calling her friend and filming me, all while continuing to step on my fingers. Her friend "Ari", now on speaker phone, exploded into laughter. I felt completely humiliated now, on top of the burning pain in both hands.

"-Oh my god I can't you're gonna make him fall!"

The girl then addressed me for the first time:

"-Kiss my fucking foot!"

"-W-what?", I said

"Kiss it biiiitch", Ari chanted over the phone, sending them both into laughter. The girl pointed down at the toe of her shoe sticking out between the bars. She underlined the command by briefly pressing down even harder with the heel, which hurt like hell. I had no choice. Mustering strength I didn't think I had, I bent my arms to hoist myself up to the level of the walkway. My upturned face was right against the sole of the shoe whose heel kept pressing down on my knuckles, and I saw her puckering her lips and make a kissing face while moving her fingers to zoom in the camera. Left with no other option, I closed my eyes and planted a kiss against the rubber, trying not to think of what she could have stepped in. Ari wasn't satisfied though.

"-Suck it! Deepthroat it like a slut!"

\-"Oh my god", the girl said in shock at her friend's suggestion. But nonetheless, she looked down at me again and gave the order before grinding the heel down again:

"-Come on now, just the tip! Get it!"

My forearms were burning from holding on so long, but it didn't matter. If I released my grip, the heel would probably rip open my hand on the way down. I pulled myself up again, and felt the heel ease off a tiny bit. I had to pull myself up higher this time, to hook my mouth over the pointed toe. The cruel lady had angled her foot slightly upward, meaning gravity forced the shoe deep into my mouth until its sides cut its corners and I gagged from the pointy tip hitting my throat. I felt the dirt of her sole against my tongue.

"-Yeeeah good boy!" I heard over the phone.

Struggling to look up, arms burning, I once again saw the bright red underwear and the visibly amused towering figure above me. I felt like a lab subject being inspected, completely exposed. It was then she did perhaps the cruelest thing. Without saying anything to her remote spectator, she moved a hand down between the folds of her skirt. She traced the red cloth down to her pussy, and then slid it aside. First I thought she was simply teasing me with the view, but then she started stroking herself with small circular movements. She'd now gone completely silent, and her gaze was a little distant.

Unbeknownst to her friend cheering "Deeper!", she was masturbating to the sight of me gagging on her foot, dangling precariously with both hands completely crushed and trapped under her expensive designer shoes. I let out a muffled "mmmmfff!" to no avail as I felt the heel mercilessly dig even harder into my hand. I tried biting into the shoe, but it was hard and unrelenting under my teeth. As a finale, she opened her mouth while maintaining the mesmerizing eye contact, and spit right down onto my forehead. I then felt the heel lift, followed by a light kick into my mouth. Nothing more was needed, my hands instantly slipped from the ledge and I fell straight down with an uncontrolled splash. I fell backwards, and before I could scramble to my feet, I instinctively grabbed hold of my aching injured hand. Looking up, I saw the girl still at the railing, filming me while furiously rubbing herself. She then turned around and I heard the hasty clicking of her heels as she disappeared out of sight.

I had a difficult time explaining my wet clothes and the big red mark on my hand to my parents the next day, but this night changed me forever. You'd think in a bad way, but quite the opposite. I wanted nothing more than to experience it again.