Valentine's Day

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The story of a man sent naked and embarrassed into Sydney.
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[This is my first story as an embarrassed naked male. The story revolves around a cheating husband who is taught a lesson in naked embarrassment to correct his errant ways. All feedback and comments - both positive and constructively negative - are most welcome. I also enjoy PMing with people. Warning to prospective readers: this is a story of female domination, so the nudity described is purely male rather than female.]

The chill night air cut through me as I stood outside the hotel lobby, facing a bustling street in the middle of Sydney. The vibrant night life of one of Australia's major cities washed over me, as I simply stood there in a trance, dressed lightly in running clothes, and with a simple backpack slung over my shoulders. I held my mobile phone in left hand, the palm both cold and sweaty, shaking slightly to anyone who cared to pay me any attention. The only people who seemed to be aware of my existence at the moment though were the few hotel guests who had to irritably edge their way around me, to get either in or out of the lobby, while I stood rooted to the spot.

Finally, a few disgruntled murmurs from a party heading out on the town woke me up, and I glanced back down at the txt message.

"Go to Pyrmont Bridge now. You'll find the key to the padlock where I told you it'd be."

The message was from Jenna. The bag I wore on my back was from Jenna too, and the combination of those two facts was more than enough to break me out in cold sweats. Hanging innocently off the small loops in the bag's twin zips was a padlock, which left no doubt that the bag would only be opened when I retrieved the padlock key from it's resting place.

Other than the backpack, my phone, my plain black running shorts, a tight white running t-shirt, and a cheap pair of running shoes, the only item I had on my person was a small black box. The small black box had arrived with the backpack at the hotel reception early this afternoon, with a clear message for it to be delivered to me as a matter of priority. The box itself had a stylish silver chain wrapped around in in multiple directions, with a similar padlock to the bag's carefully ensuring the chain could not be removed.

I had no form of identification, no money, and especially no hotel room key. That much had been made very clear in Jenna's last txt. She'd made me video the act of closing my hotel room door, and slipping my one and only access card under the door frame so that it was now irretrievably back in the room. My only option would be to ask for a new card from reception, but I would only be allowed to do that at the end.

The end of what though? What did Jenna have planned for me?

I gulped audibly, and clenched my jaw as I took a couple of hesitant steps forward. Streams of nightclubbers and revellers surrounded me on all sides as I staggered into the busy central city street, lost in my own sea of emotions.

How she'd found out about the affair, I'd never know. But when Jenna had contacted me a week back, just prior to my business trip to Australia, my blood had run cold as the woman at the other end of the line clearly stated her intentions. The words she'd used has almost not been the worst thing about the conversation. It had been the calm way she'd said it, with an icy undertone and an unmistakable air of determination. Words I could have discounted, I could have perhaps laughed off, no matter how foolish that would have been in the long term. There was no arguing with that voice though.

Jenna had been very, very open. She had all the evidence she needed to end my marriage. She was willing to hang on to it though, to hold fire on ending that chapter of my life, if only I was to obey her every instruction without question and without hesitation. And I'd only need to do it once - on my upcoming business trip - and Jenna would supply everything that was needed. Any attempt though - and she meant _any_ attempt - to dodge or cheat at the mission she'd give me, and she'd mercilessly unleash every ounce of information she had on me to the Internet.

I closed my eyes as I remembered how I'd felt after she'd hung up on that conversation. My dry throat, the turmoil of not knowing what she'd have me do, and the inescapable certainty that I'd simply have to do it.

That had been a week ago, and now the time of reckoning was at hand.

I began to break into a jog. I knew Sydney fairly well, and I knew where Prymont Bridge was relative to my own hotel. It was a major pedestrian bridge that crossed Darling Harbour, and would undoubtedly be packed with people moving from one part of the city to another. Whatever Jenna had planned, it apparently wasn't meant for a small, private audience.

I was fit, and kept in shape with plenty of long runs, but the ten minute light jog to the bridge left my legs feeling like jelly. The night air was cold, but thankfully the rain had held off, and the jet-black sky was punctuated by the bright high-rise lights of the city, and a dim background of stars.

The men and women of Sydney seemed to regard me a slight oddity as I jogged onwards, a few people a little surprised that someone would think a Saturday night was a good time for an evening run. There were obviously more pressing engagements on their agenda though, and much more drink to be had, so I generally passed by without too much interaction.

I even began to fall into a runner's rhythm, and slowly began to lose myself and my worries in the pounding of the streets. That was - at least - until the lights of the bridge came into view, as I rounded a corner of one main street and arrived at a busy intersection.

I knew where I had to go. I had to cross the bridge and reach a small rubbish bin that sat innocently by the far end, where a road swung around to touch, without ever crossing, the pedestrian bridge.

As I waited for the crossing lights to turn green, my nervousness began to build again, threatening to overwhelm me as I stood at a red light, surrounded by so many people loudly talking about everything and anything that entered their minds. Through the noise of the people and the cars and the music from the bars, a single sound suddenly sliced through the air. It was my phone, signalling that another txt message had arrived.

With one eye closed in fear, I glanced down at the phone's screen.

"Are you there yet?!" the txt demanded.

With several mistypes caused by my shaking fingers, I fired back the reply. "Almost."

"Don't disappoint me. And don't try to cheat... again." came another txt, barely seconds after I'd hit send on my own reply.

The crossing light turned green without me noticing, and I made it across the road more by virtue of being carried across by the crowd around me, rather than any deliberate movement on my part.

The bridge awaited though, and Jenna was waiting too. I could not delay any longer.

I half-stumbled on to the bridge, and surveyed the nearly 400 metre length of the structure. There were groups of people crossing in both directions, and the the bright lights of the street lamps meant that the bridge was bathed in a warm glow. Whatever Jenna had planned, there would be no hiding in shadows tonight.

I made it across the 400 metres in a daze, just focussing on putting one foot in front of another. I'd even had to double back at one point, when I realised I'd forgotten to place the chained box at the near end of the bridge. That had been one of Jenna's earlier instructions, and failure to comply would lead to the failure of marriage.

Eventually, I made it across the bridge, and stood in front of the innocuous looking rubbish bin. I could see the shiny metal key stuck to the bottom of the bin, where no-one else would have thought to have looked.

Another sound from my phone. Another txt.

"There yet?!"

"Yes." I replied, simply.

"Well, get on with it then. You won't want to waste time." came the next message.

I held my head in my hands, as ice seemed to run down my veins. This was it. The point of no return.

I half-laughed at that thought. I was way past the point of no return, I realised, bitterly.

Reaching down to take the key, I fumbled at the padlock on the bag, and was "rewarded" when the padlock finally gave way, and allowed the zips to part.

It took me several seconds to work up the courage to open the bag up, but when I did, I was greeted with the sight of a stylish card, and two plastic, opaque bags. At least one of the bags appeared to have larger, oddly shaped objects in it, while the other I quickly guess would have clothes.

It was obvious I should read the card, and left the rest of the contents by my feet as I delicately opened it up. There wasn't much writing inside, but what there was almost sent me into shock.

"Dear Stuart." the card started, mockingly. "You have five minutes from the time I send you a txt saying "get on with it" to take off all your clothes. Every last stitch. You are then to put on the costume I have kindly provided, and send me a selfie of you in that costume."

My mouth went dry again, and my eyes were wide open.

"If you don't do this, then I will send your wife everything she needs to know to make a very tidy sum out of your divorce settlement."

Oh God. I thought.

There was only a little bit left on the card, but the tone and the tasks didn't not improve my mood.

"Once you are dressed, you are then to send me a video of your old clothes and the backpack being thrown into the harbour. You will then receive further instructions."

I had to read the message three times to allow myself to believe it. Every time I read it, the horror grew that much worse. It was only on the third read through that my mind snapped into action as I realised the importance of that five minute warning.

Acutely aware of a couple of highly attractive women who'd chosen that point to walk by, I ripped my shirt off and dropped it reluctantly to the ground. I caught their attention, and out of the corner of my eye I knew they were turning to check me out. Oh God no, I thought. Why couldn't they just walk on? Why did they have to stop? "Could I afford to stop?" I asked myself desperately. Not now, I realised with an impending sense of doom. I couldn't stop now.

With their eyes firmly fixed on me, and with more men and women approaching too, I grasped the edges of my running shorts, and forced them down my legs, inch by inch.

With every inch they lowered, my face went a brighter shade of red. I could barely believe I was standing on a busy bridge in the middle of a busy city, exposing my underwear to random women, my ears burning with every shocked and whispered comment that floated over the night air. One of the women was now pointing and laughing as I stumbled out of my shorts, and left them scattered on the ground by the t-shirt.

"Take off the underwear!" her companion shouted, with glee in her voice.

The request cut through me, and I felt like I'd been shot as my mind comprehended the fact that I had no choice but to do it. My predicament came even worse when I realised that there were groups now approaching from all directions. No matter what way I turned, I'd be exposing myself to at least someone.

I tried to guess at how long had passed, and I began to panic even more as I realised I properly had only a minute or two left.

Surrendering myself to my total humiliation, I grabbed my underwear, and roughly shoved it down to my ankles, bending down and exposing my ass to the two women who had first noticed me. They whooped in joy at this unexpected entertainment, and were loudly calling out for other women to come and check this show out.

As I stood up, my penis was rock hard at the overwhelming embarrassment, and I stood petrified for a few seconds, hands handing loosely by my sides, as I realised there was a group of teenage girls directly in front of me. Part of my mind madly guessed there were probably only eighteen years old, and they all were openly laughing at me as I stood naked, nude, helpless in front of them. Shaking, barely able to process what I was doing, I desperately reached for the bags, and emptied them on to the ground.

"No!" I cried out, as I realised what Jenna had given me. Staring back up at me from the floor, was a red crotchless lace teddy, that split in half early on and clearly would expose most of my stomach and chest. The back was barely more than a few threads, and I hurriedly looked in the other bag for what I hoped would cover up this humiliating outfit. I was terrified to find only a pair of matching red high heel shoes, and a small chain with another padlock key hanging off it.

Crude catcalls echoed around the bridge as I picked up the clothes, and a few moments of manic necessity powered me on to put on these ridiculous clothes. The red lace teddy looked nothing like men's clothing, and I'd never worn anything even remotely like this in my life. I wouldn't be looking to repeat the experience in the future. My cock was barely contained in the thin fabric at the bottom of the teddy, and I had to futilely try and cover my large erection with one hand, as I frantically tapped away on my phone's keyboard.

Trying to ignore the ridicule and mocking insults that the women on the bridge were subjecting me to know, I took a selfie of me in the red lace teddy, and stared in disbelief at the resulting photo. I couldn't recognise the man in the picture. Red-faced, feminised beyond belief, and a look of total defeat in his eyes. The humiliation of the man in the picture stung me as I took it all in for a few more seconds, before I remembered what I had to do next. A few quick keystrokes, and with a sinking feeling of what this meant for the future, the photo was sent, and I stood helplessly there, stranded as the sexual object of everyone's dirty-minded innuendo.

As I waited for a reply, I realised there was a second step to my instructions, and with a robotic, jerking motion that betrayed my shock, I gathered up my old clothes and the backpack, and unceremoniously tossed them over the bridge, videoing the whole process for the benefit of Jenna. Seconds later, I heard the faint sound of something hitting water, as I tried to tune out the requests for more photos from my baying audience.

Trying to lose myself in my own world, I held my cock in one hand, and my phone in another, suddenly finding myself praying for another txt from my tormentor.

She did not disappoint me.

"Not bad." came the simple reply. Moments later, a more substantial txt arrived.

"For the time being, your marriage is safe. Happy Valentine's Day. :) "

The smily emoticon was clearly mocking, and my grip tightened like a vice around the phone, as I read on in helpless frustration.

"I hope you like your Valentine's Day outfit. Of course, Valentine's Day is a day for love."

That cut at me, as another txt arrived.

"To prove your love for your wife," Jenna continued, "you're going to walk your cheating ass back to the other end of the bridge, surrounded by all those people. Don't worry - I have another outfit in that box you placed there, for you to get back to the hotel in..."

Did I dare dream that the walk over the bridge would be the worst that Jenna had planned for me?

"Go now." Jenna finally said. "When you've reached the box, let me know."

I closed my eyes, and tried to chant to myself to steady my now-shot nerves.

The teasing and taunting of the women was now merely background noise, and I shut it out with some success. However, as I stood there preparing myself to walk, one of the teenage girls boldly walked up to me and spanked me hard on the ass. I gasped loudly, more in surprise than pain, and looked at her in shock. With a wink, she brushed my hand away that I'd been using to try and cover my penis. Looking back triumphantly at her girlfriends, she pulled the material down so that my cock completely popped out, and hung there on display.

"What do we think ladies?" the teenager asked. Her friends gave me the thumbs down, with a disapproving look on their cruel faces. My embarrassment was now a tidal wave of humiliation that threatened to drown me, and I staggered back away from her grasp, and shoved my cock back inside the tiny confines of the thin, lace material.

Between the shock of the woman's forwardness, and my lack of familiarity with high heeled shoes, my backwards stagger soon turned into a stumble, which eventuated in a shambolic fall that left me splayed on the ground. As my hands subconsciously were thrown backwards to mitigate the worst of the fall, my penis fell out of the clothing again. I found myself spreadeagled on my back, legs apart, penis prominently standing to attention, and my arms flailing around helplessly.

Unable to stop them. I realised too late that I was now the central focus on many a mobile phone camera, and I fell over several more times as I frantically tried to regain my footing.

Eventually I succeeded in standing up, and started a desperate shuffle down the bridge. The red lacy teddy moved over my chest, as a light breeze almost threatened to tear it from my body. As I hurried away as fast as my high heels would permit, I was painfully aware that I was exposing my entire backside to the leering ladies who'd made me the object of their mockery. The thin strands of clothing that held the front together hid nothing, and as I heard footsteps behind me, I feared that the women had the intention of doing what the breeze had so far failed to do. It felt like it would only take a few tugs at the strings in my ass and around my bag for what little clothing I had to become the sole property of one my "admiring" audience members.

"Would that be an improvement?!" I thought, wildly. The humiliation of wearing women's lingerie in public was almost too much to handle. The sexy Valentine's Day outfit, resplendent in red, almost looked a dull shade in comparison to my bright red face. Even my ass shone from where the teenager had roughly spanked me.

The walk over the bridge at the start had been only around 400 metres. The return felt more like 4,000 metres. As I pushed ever onwards, one of my followers would occasionally dart forward and whisper something disgusting in my ear. More than a few women had run ahead, and were now filming me as I walked towards them. As much as I tried to cover up my front, I knew in my heart of hearts that there were more women filming me from behind as well. The only faint saving grace was that I was from out of town, and nobody knew my name. Nobody except Jenna, of course.

I gulped again, as the cold night air set my nipples rock hard. The key had to be placed at the bin, I suddenly realised with a flash of terror. Did that mean Jenna was watching me as I did this? Or did it mean she had an agent around, to ensure I didn't cheat? Cheat any more than I already had, at least.

The innuendo and comments on how I looked were supplemented by the occasional bystander giving me another spank on my entirely exposed, naked rear end. One daring woman even reached forward and grabbed my balls, giving them a hard squeeze and causing me to stop momentarily and groan in pain. I pushed on regardless though, my mind focussed entirely on that box at the end of the bridge, where hopefully another more modest outfit awaited me.

Eventually, after what seemed like hours (even though it logically could only have been minutes) I made it across the wide pedestrian bridge. My show was now famous throughout the immediate area, and quite a crowd now surrounded me. The air of excitement at what was to happen next seemed to drag even more people into checking the commotion out.

There it was. The box. I stopped in front of it, my feet already sore from the brief hike in the high heels, my ass ringing from repeated assaults, and my ears flaming with all manner of erotic suggestions.

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