A Walk of Shame

[The following is a true story of an event that happened five years ago. The video of the event was mercifully never published and has since been lost to the mists of time. It may be tame by some standards, extreme by others. However, it was still one of the most embarrassing moments of my life to date. I have made no attempts to embellish the story, and this captures exactly what happened as best as I could manage, for better or for worse.]

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There was, I reflected, something about standing in the middle of a forest path, the trail meandering away in both directions and disappearing around bends obscured by trees, that made you feel like you are the only living creature in the world.

Beyond the gentle rustling of the leaves and the dancing rays of light that penetrated through the overhead canopy, there wasn't even the chirping of birds or the scurrying of an ground-dwelling animal to disturb the peace.

However despite all that, I was standing to one side of the path, trembling. For while the forest was doing its best to make me feel all alone, I'd come armed with a device that brought the whole world back to haunt me, the full impact of what I was about to do bearing down on my shoulders, causing me to hunch slightly even though the device in question was on the other side of the path.

It was something as innocent as my phone, a device I'd carried with me every hour of every day for countless years. Yet not previously for the reason I was using it today. For today the phone was resting in a low-hanging branch of a young tree, and the camera on it was pointing directly at me.

I was dressed in a normal blue t-shirt that clung to my body protectively, black shorts with red piping, and plain white socks complemented by the most nondescript of white running shoes. Nothing that to an outsider that would look at all out of the ordinary. Yet this wasn't to be the outfit that I'd be walking back to my car in, parked not too far away admittedly, but far enough that the chance of coming across a stranger wasn't out of the question. No, the outfit I'd be doing that walk in was already scattered in front of me, taken out of my backpack by nervous hands that had shaken uncontrollably as I'd pulled out first a pair of frilly pink princess panties, followed by pink lacy socks, and then a white crop top that was several sizes too small and that had "Daddy's Girl" printed in lettering that would be impossible to miss or misinterpret even at a distance.

Now, I was standing on a path in a forest on the edge of my home town, not that far from a car park where day walkers would commonly come to for a few hours of carefree walking in a serene, peaceful environment, away from the hustle and bustle of everyday life, and yet there was nothing serene or everyday about the task I was about to embark on.

How I came to stand here was a slightly complicated matter. As I dropped to my knees and retrieved my final item from my backpack - a plain black mask that would cover the top half of my face and my hair - I glanced back up at the phone, barely six feet away. The phone itself was already safely secured in a selfie-stick that I could use to hold the camera out in front of me as I walked back to the car. That my entire ordeal would be recorded was a critical part of the complicated arrangement that had led me to be here, trapped and with no options other than to risk complete embarrassment.

The easiest way to explain the complicated matter is to simply confess that I'm an uncomplicated idiot. I had made a bet - five words that had been the downfall of many a man, although perhaps not in the quite the same way as my own story! - with a woman I knew online. A certain Jenna Burlinski. Jenna was pretty big in the niche Embarrassed Naked Female genre of erotica, and seemed to have an equal interest in the even smaller genre of Embarrassed Naked Male. We both also enjoyed watching NFL, and yet supported different teams. This was, in my view, a perfectly reasonable justification for a series of increasingly risky bets. As I said, I'm an idiot. If you were to perhaps suggest that idiot didn't quite do full justice to it, and that maybe the phrase "self-destructive moron with a tendency to set myself up for failure" you'll appreciate that I'd protest my innocence to the fullest degree, and put it all down to over-confidence. Yet we'd both know really where the truth lay.

I genuinely had hoped to win the bet. I think. Or at least, if I'd secretly hoped to lose the bet when the bet was made, I can with absolute confidence assure you that now I was fervently wishing I hadn't lost the bet.

It was a simple enough bet. I supported the Bengals, Jenna supported the Cowboys. Both teams were due to play each other that year. Now, for those of you reading this in a year that the Bengals suck in - of which there is a better than even chance - in my (partial) defence the Bengals weren't so terrible the year of this bet.

The bet required the loser to wear an embarrassing outfit and complete a task in it. The margin of the loss was to determine the riskiness of the task.

I'd genuinely assumed the game would be close, so even if I was secretly hoping to lose (and I refuse to acknowledge that this was the case) then at least it would be a simple enough task. The Bengals were good enough that I assumed maybe a 6-point loss was the worst I was likely to be looking at. So you can imagine how dry my mouth was at three quarter time and the Bengals were down by 28 points. It was the smallest of mercies that the Bengals fought back against a now more relaxed Cowboys team to "only" lose 14-28 at the end, but a 14 point drubbing still left me with a pretty significant struggle ahead.

As the loser, I would need to stand here in the forest clearing, strip completely naked on camera - with only a mask to protect my dignity - and then change into the humiliating and extraordinarily feminine outfit Jenna had chosen for me. Then, I would need to film my walk back to my car. I couldn't run, and so the walk would take at least five minutes. Five minutes normally would pass like a flash, but I already knew with a lump in my throat that those five minutes would feel like an eternity.

Upon reaching my car, only then would I be able to stop recording, and to ensure full compliance, the recording was to be immediately sent to Jenna. I had never done anything so extreme. It was impossible to know ahead of time whether I'd stumble into someone I know. Even coming across a stranger would be easily the most humiliating thing I'd ever done in my entire life.

I kept telling myself that wearing the mask would protect my dignity. On some level I suppose that was true, as my real identity wouldn't be revealed on camera if Jenna decided that - as would be her right - that she could simply upload the video on to PornHub. But I knew the mask wouldn't save me from feeling entirely embarrassed if I passed someone and they reacted in slack-jawed shock - or worse, mocking laughter - at my ridiculous attire. And it was my car I was walking back to. What if someone recognised my car, or was sufficiently interested to look me up on a database?!

I'd sat in my car for probably twenty minutes, alone in the car park except for one other car, frozen and unable to move, hoping against hope that the person from the other car would return and drive off. Eventually I'd had to nervously open by car door and step out into the morning sun, feeling incredibly exposed in the open car park even though I was equipped in my perfectly respectful man-clothes at that time.

Somewhere out there, the person from the other car was still walking. Maybe they were still walking into the forest, in which case I'd be unlikely to run into them, maybe they were already returning. It was the not knowing that made it worse, of course.

Finally summoning my courage, I hurried away from the car park and hit the path that snaked up a hillside. I'd need to walk at least five minutes into the forest, and barely one minute in, I hit a fork in the path. My heart skipped a beat. I knew there was at least one person out there. I had a fifty percent chance of picking the path they were on, and an equal chance of walking on to a path that I could cling to the wild hope was empty. Of course, there was the small matter that someone else could arrive behind me, and I was now silently cursing the fact that I had waited for so long in the car park. No one had arrived, either in a car or from the path, and in those preceding twenty minutes I could have gone out, done the task, and be safely back in my car without having been seen! Yet, here I was, precious moments of undisturbed quiet having been wasted.

As my eyes refocused on the camera in front of me, my mind catching up from that time in the car park to the here and now, one hand still clutching my mask, I realised I was repeating the same mistake as before. Just standing mutely here while priceless moments of alone time slipped away, and the seconds slipping away were counting down to when someone else must inevitably appear.

I swore, the quiet yet passionately uttered words breaking the silence in the forest. Twitching slightly, I hurriedly put the mask over my face, looked nervously up and down the path, and struggled to get my rapid breathing under control. Still shaking, I took several steps forward and clumsily turned my phone's video recording on, pausing only for a moment to ensure that the camera was oriented properly to record my strip. There was no way I wanted to do this twice if there was a problem with the setup!

Finally satisfied that it was recording and ready, I stumbled back a few steps, took one final long breath in, cursed my past self who had thought it would be oh-so-funny or arousing to make such a stupid bet, and gritted my teeth. Grabbing the edges of my t-shirt with my hands, I roughly pulled it up and over my head. The t-shirt caught for a moment on my head, and I frantically tried to stop it from pulling my mask off. The t-shirt was over my head for several seconds before it finally came loose, and while it covered my eyes, I half expected to hear the sound of footsteps coming from either direction. That said, no way would I be so lucky that if someone did come across me, it would be while the worst that was happening was that my chest was exposed...

Topless, I felt vulnerable in front of the recording camera, the red light at the bottom visible even from where I was standing. Still, the act of removing my t-shirt now spurred me into action. I removed my shoes next, followed by my socks, and I stuffed the plain white socks into my backpack. I wouldn't be needing my socks again, but I would be needing my shoes.

Again I glanced up and down the path, and again I was mercifully greeted only by the sight of gently swaying branches of trees that towered up into the clear blue sky.

Pulling in another deep breath, I now hooked my hands on my shorts and pulled them down to my ankles. I could feel my cheeks going red as I staggered and almost fell over as I struggled to step out of the shorts, but having finally managed it, I too stuffed these shorts into my backpack. Down on the ground in front of me, my next outfit caught my eye and I froze again for a few seconds as the enormity of what was about to happen hit me in the chest.

Glancing back at the camera, I could see on the screen a picture of a man in his underwear, wearing a mask and otherwise naked, shoulders sunk slightly and one arm protectively wrapped around his bare chest. That was me, and in a second or two, that underwear would also be in my backpack, and the man on the camera would be naked, red-faced, vulnerable, and helpless should anyone else come along. Yet incredibly, even that would be an improvement on what would then have to follow.

I scrunched up my eyes and then - chanting silently to myself "no more bets with Jenna Burlinski" - I fumbled at my underwear and hurriedly pulled them down my legs. I tried to cover up my manhood in one hand, relying on the other to pull the underwear down past my knees and down to my ankles. To say that was awkward was an understatement, and it dragged out the process by a few extra seconds during which I swore my face transitioned through deeper and deeper shades of red.

Finally the underwear was off, and I flung it at the backpack. It didn't even land on it properly, but that was a problem for later. It had been a requirement that I be fully undressed on camera before putting on my new outfit, but it hadn't been a requirement that I actually show off my cock, so one hand was firmly planted over it while my other hand dove down and grasped at the pink princess panties that I would now need to put on.

All the time, the red light on the camera silently glared at me, stating with absolute clarity that every second, every moment of struggle, every agonising feeling of absolute humiliation was being recorded for posterity.

I tried to step into the panties with one hand holding on to them. My foot missed, and I almost fell forward. I steadied myself, ears straining to hear any footsteps that might be approaching, my heart in my mouth and my brain now consumed by a growing panic. My foot went for the panties again, and I managed to get it through a gap and half-pull it up my leg before I realised in horror that I'd put my leg through them the wrong way, and I'd have to take them off again. Cursing my own ineptitude, and knowing that every second was precious, I gave up any pretense of hiding my manhood from the camera, and now used both hands to hurriedly put the panties the right way around and step into them yet again. This time there was success, and I tried to pull them up as quickly as humanely possible, while the camera filled my phone's memory with searing images of my naked cock, dangling down between my legs. Worse yet, it had partly shriveled up in embarrassment, and it didn't take a genius to guess what Jenna would make of that.

Finally pulling the panties over my crotch, I awkwardly jammed my balls into the soft material of a lingerie item designed for an entirely different kind of anatomy. They barely fitted in. It was an open question as to whether it would have been better for them to easily fit it - so as to avoid them spilling out as I walked and potentially flashing any passer-by - as that would only have given Jenna more ammunition for mocking retorts when she saw the video.

Having finally secured my frilly pink princess panties, I grasped at the "Daddy's Girl" crop top, and mutely pulled it over my head. It was far too tight a fit, and my stomach spilled out underneath it. There was nothing even remotely sexy about the look, and it was entirely designed to be embarrassing and humiliating. Mission accomplished, I thought bitterly. The crop top dug into my sides under my shoulders, and I grunted slightly as I dipped down yet again to now retrieve the lacy pink socks that would - with my shoes - be the final touch for my complete emasculation. It almost seemed redundant given the panties and the crop top, but Jenna was nothing if not thorough. And putting the socks on slowed me down for at least half a minute, hopping around on one foot and then the next, all of my manic antics captured on film, and every second of exposure increasing the odds of being discovered.

As I pulled the socks up to my knees, I was then at least able to put my shoes on, and retaining just enough self-control to be able to do my shoes up on the first attempt, I eventually stood up and was fully "dressed", as yet undiscovered, still alone in the forest, and now with the longest five minutes of my life stretching out in front of me.

Sucking in air and uselessly trying to calm my scattered thoughts, I pushed all of my old clothes down into my backpack so I could zip it up, and then walked quickly over to my phone. Retrieving the device from the branches, I held it out in front of me via the selfie-stick, and shook my head as I soaked in the absurd sight being recorded. God, I looked like a fucking idiot!

I desperately wanted someone else to blame for this, the Bengals for playing poorly, Jenna for taking advantage of an idiot, but truth be told I'd overestimated my own team and I'd been the one to propose the bet, not Jenna. So the blame sat squarely with the sissy boy on camera, and what sounded like a fun and sexy challenge two weeks ago when innocent messages had been exchanged, had now taken on the form of a deeply humiliating experience.

I had to get back to my car undiscovered.

Looking behind me, I was at least thankful that no-one was coming down the path. Once I started moving, I only had one direction to really worry about. I couldn't run, but I wasn't intending on dawdling! Setting off at a reasonably quick walk, my senses fired on all cylinders as I started around the first bend and the next stretch of the path loomed in front of me. Still no-one in sight. Still no sound of anyone approaching. I took another breath. Could I be this lucky, after being this stupid?

The second bend was navigated quickly, and the path began to drop down the hill, taking the form of several steps and then stretches of path with slightly uneven earth. My eyes were straining to see around corners, and not focused on the ground directly in front of me, and more than one I almost fell forward. Now that would be a great look for the ever-present camera to record! Nevertheless I stumbled on, just managing to maintain my poise even if my dignity was firmly stuffed in my backpack, held in one hand while the other tried to keep the camera steady and on me at all times. I desperately needed to ensure Jenna had no excuses for demanding a re-do.

Around a third bend now, and while I was only half-way, I now had a clearer and longer view of the path ahead. It zigzagged down the open slope of the hill for while before finally disappearing into a clump of trees which was itself only a minute or so from the safety of my car. Or, I couldn't help but think, the danger of a populated car park.

I mentally tried to break down the task in front of me. Step one: make it down the hill. Step two: walk as quickly as could be said to be within the spirit of the rules through that cluster of trees, and that I now remembered connected with the second path I'd seen upon entry. Step three: get to my car, climb in, and find anything to hide my current outfit so I could slink away in relative safety. I'd made it this far, I chanted to myself, I can survive the last few steps.

Of course it was then, as I allowed myself to mentally look ahead to the car and dare to dream of safety, that I saw movement at the edge of the trees. A woman, possibly in her mid-twenties and wearing entirely normal walking clothes, emerged at the foot of the hill. I was up higher, but I knew if I could see her, then as certain as grass was green and water was blue, she would be able to see me too.

I froze. Standing them stupidly in girly underwear, a ridiculous crop top, and frilly pink socks that were entirely at odds with my hairy legs, I knew that if I continued I'd have to not only walk past her, but be the object of her attention for at least half a minute while I struggled down the hill.

Panicking, I sensed her look up the hill in my direction. Not waiting to see if she had noticed me yet, I reacted with the most primitive of fight or flight instincts, and turned heel to run back up the way I'd came.

In that moment, I didn't care about the car, or even the recording, although as I dashed up the path I'd just walked down, I could see the stricken face of the sissy on the screen, his jaw quivering and his stomach bouncing up and down, squeezed out by the crop top and that was now riding up his body and resembled more of a sports bra now. Part of me knew that I could be running towards someone else, come down the path from the other direction, but I was caught up in one overriding thought - I had to get away from that woman!