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The Girl With The Enigmatic Smile - Trouble Brews

"I need Emma to release me from my chastity cage so I can spend a night with my old flame, Nicole. Will Emma agree, and, if so, at what price?"

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Author's Notes

"This is the third part of "The Girl With The Enigmatic Smile" a fictitious story about a man's infatuation with his nineteen-year-old neighbor, Emma, the girl with the inscrutable smile. He has foolishly locked himself into a chastity device, over which Emma has full control. As if that wasn't enough of a problem, he's received an invitation from his old flame, Nicole, to spend a night of passion in her apartment. He's now racing against time to resolve his predicament."

Despite my plight, the thought of Emma controlling my ability to have erections or to ejaculate was arousing me. Consequently, I had very little sleep that night due to the throbbing of my penis within the tight constraints of the chastity device. Three times, I had to go into the kitchen to press a bag of frozen vegetables against the cage to cool my ardor!

But I knew that if I was to visit Nicole, and we were to engage in lovemaking, somehow, I had to persuade Emma to free me. Moreover, I had only a few hours to get myself released.

Understandably, despite being dog tired, I was awake early, and I looked for an email from Emma—there was nothing. I toyed with the idea of going around to confront her. But then, as I was weighing up the pros and cons of doing that, I heard her front door slam shut with an almighty bang.

I felt a sense of relief. This was the signal that meant Emma was consenting to speak to me.

Rushing out of the front door, I saw she was sauntering down her driveway. She was dressed as she always is—shapeless jeans, baggy T-shirt—in need of an iron—and a baseball cap, through the back of which protruded her blonde ponytail.

“Hello, Emma!” I yelled, trying to sound as chirpy as I could. “How are you today?”

She turned to face me, with that familiar, inscrutable smile. “Okay!” she cheerfully replied. “You okay?”

“I'm... I'm okay, but I've a problem, Emma.”

“What?”

“It's embarrassing,” I answered, “I think you can help me.”

“Doubt it! Computer tech is the only thing I know.” I could see she was intending to play dumb, as was usually her way.

“I... I need you to unlock me, Emma... please!”

What? You're locked out of your house, Mark?” Her trademark enigmatic expression had morphed into a wide smile. “Dad can help you. Shall I give him a call?”

No!!” I exclaimed. “But I think you can help. You have an app on your phone called 'Keyholder', don't you?”

“Do I? Never seen it. Never heard of it.” With that, she opened her phone and scrolled through all the apps, showing me as she did so. Just as she said, there was no app with that name. Either it was hidden in a secret folder, or else she had a second phone.

“Why would I have it? What's it do?” she asked, with what I took to be a fake expression of curiosity.

I hesitated for a moment and then blurted out, “It unlocks the chastity device I'm wearing, Emma. I need to take it off.”

She screwed up her eyes and shook her head in apparent bewilderment. “What the fucking hell is a chastity device?”

By now, I was scarlet-faced. “It locks onto my... er... penis, and stops... you know what...”

No! What does it stop?”

“It... it stops erections and orgasms.”

Nooooh!!” she exclaimed, smothering a grin. “That sounds so cruel. Who put it on you?”

“Well... I did.”

You did!” she spluttered, incredulously. “Then can't you take it off? Or do you need my dad's help?”

“No! Please stop trying to be funny, Emma, because this is serious. It has to be unlocked and only you can unlock it! You know you can.”

Me? Have you gone batshit crazy? This conversation is scaring me. You're weird.” She spat out those final two words, making me cringe.

“I've got a date tonight, Emma. I need to be freed.”

“Well, that'll teach you not to be so stupid as to lock your whatsit up, won't it? Not my problem, Mark.”

“Please, Emma, please,” I pleaded, but she turned around and walked off, carrying her skateboard.

oooOOooo

I went back into my house and sat brooding for a couple of hours, trying to figure out how I could get free of the chastity device. I'd already tried brute force and had quickly given up for fear of causing bodily injury. Uninstalling the app was something I considered, but that still wouldn't stop Emma having control. And I was certain that changing the password wasn't possible without her permission.

Perhaps draining the battery might work, except I could see no way of doing that. And I remembered that the instruction manual said a single charge would last at least six months, after which time it would automatically open. How could I survive, locked up, for that long?

However, I thought, what if I were to disconnect Bluetooth and Wi-Fi? Might that work? I turned both off and waited to see what would happen—nothing! The cage remained locked and then, a few seconds later, a notification popped up on my phone: “Connections lost, Keyholder 1 informed”.

My God! Emma knew I had attempted to break out of the cage.

Hastily, I reconnected and waited to see if she would message me, to admonish me for disconnecting. But no, what she did was far worse. It was something I had read about in the manual but naively assumed she would be unaware of.

As I sat contemplating what she might say, out of the blue I felt what had to be a lightning strike blasting my genitals. I let out an ear-piercing shriek and was left gasping for breath.

I waited nervously to see if there would be a further shock—there wasn't. This had been a warning and one that I best heed. I couldn't bear to think of the consequences of her shocking me in a public place.

oooOOooo

I was stymied, stuck in this damn cage, and I was about to message Nicole to say that I would have to cancel our date that night when there was a ping on my phone. It was from "Anon": “You would look nice in these...”

As usual, the short message was in the title line, but in the body was a link to the website of a well-known department store. I clicked on it and was faced with pictures of a simple bra and panty set. Both were plain white but embellished with multiple “Hello Kitty” images.

“Anon”: “They're in stock downtown... Buy them for yourself today...”

My God, she wanted me to drive into town, visit this store and buy myself this underwear. That was a big ask!

If I did, would she unlock me? Or was it a trick? And if I didn't, would she zap me, or just continue to refuse to release me?

As usual, I was procrastinating and, in the back of my mind, I knew it was only a matter of minutes before she turned the screw, forcing me into a decision.

Sure enough: “What you waiting for? The clock is running down... Tick-tock... Tick-tock...”

The warning was clear. If I was to stand a remote chance of being freed today, I had to visit that store.

Knowing what I had to do, I picked up my car keys and left the house, making sure to slam the front door so as to let Emma know I was following her instructions.

oooOOooo

Ten minutes later, I was at the mall. By now I was sweating, and my hands were shaking. Buying stuff online was one thing, but purchasing in person was another. Yet complying with Emma's directions was my only chance of gaining release for my date that evening.

Nervously, I entered the store and headed for the clothing department. To get to the men's section it was necessary to pass through the women's, and like many men, I had acquired the knack of walking through the lingerie division with an expression of complete indifference while surreptitiously ogling the displays through the corners of my eyes. Today, though, I had to do more than that. I had to locate the panty and bra set described in the link, then find items in my size, and finally pay for them.

The women's section wasn't especially busy, yet I felt all the eyes there were focused on me. And every one of those eyes was female! There was not another man in sight. Don't let your imagination run wild, I told myself. No one is interested in what you're doing. But perhaps they were—after all, this was not normal male behaviour.

I bit the bullet. As nonchalantly as possible, I browsed the appropriate aisle and spotted what I needed. Then it struck me that I didn't know what size bra to buy because I'd never worn one before. This was not an occasion to be measured, so I had to come up with something. I knew what size Emma wore, and I knew what size my late wife had worn, so I took a guess and selected a 38C.

Just handling the two items, both made of ultrasoft, thin cotton, was enough to get me excited, in spite of my inner nervousness. But I couldn't afford to stand there—I needed to pay and get out.

Wasting not a second, I hurried to the exit and chose to use one of the automated checkouts so that I didn't have to confront a female assistant. I was praying that the purchase would go smoothly, and I wouldn't hear the dreaded warning of “Unexpected item in bagging area”!

The purchase went through, so I shoved the two items into a bag and rapidly left the store.

oooOOooo

Not long after, I was back home, making sure that Emma knew that was the case by pulling my front door closed with a bang.

I waited nervously, feeling certain I knew what was to come next. Sure enough, after a couple of minutes, my phone pinged, and I was not surprised by the contents of the message.

“Anon”: “Back bedroom window... NOW... wear bra and panties...”

Being unsurprised and being calm are not the same thing. I was trembling as I stripped off what I was wearing and put on the Hello Kitty bra and panties. I soon realized the bra was too small. Obviously, the cup size was far more than adequate, but the band size was too tight and was cutting into my flesh like a cheese wire. But I had no option other than to wear it. I most definitely didn't wish to return to the store to exchange it.

It was a relief of sorts to get the bra fastened, but that was tempered by the knowledge that Emma was expecting me to stand staring out of my window with it on. Nonetheless, if I had any hope of a date that evening with Nicky, I had to comply.

Dressed just in bra and panties, and clutching my phone, I went upstairs and stood still, looking out of my window. Down below I could see Emma, dressed in a skimpy scarlet bikini, sunbathing on her front beside her pool, looking at her phone. Subconsciously, I folded my arms, attempting to hide what I was wearing on my chest.

Nothing happened for a couple of minutes, then my phone pinged: “Hands on head...”

Emma could see me, so somewhere there was a camera that was feeding her phone. Obediently, I unfolded my arms and placed my hands on the flat of my head.

She reached behind her back and nimbly used her free hand to unsnap the clip of her bikini top. Then, slowly, she turned over onto her back, the same free hand holding the cups of the top against her pert breasts while she continued staring at the phone in her other hand. Her face bore the unfathomable smile that so infatuated me.

This was not the only time she had turned over like this, holding her undone top against her breasts. But what happened next was a first.

It was done so innocently, while she concentrated on her phone with her characteristically benign facial expression. Suddenly, the bikini top slipped by a couple of inches, revealing her nipples. Despite me being some distance away, I could clearly tell that her nipples were erect, and I could see the contrast between her dark brown areola and the surrounding lightly suntanned skin. Needless to say, I soon became conscious of my penis pounding inside its cage. What I wouldn't have given for binoculars to get a better view!

She gave every impression of being oblivious to the slippage, but I knew differently. It was a deliberate act on her part, intended to excite and arouse me—she had succeeded one hundred percent.

For a few minutes, I was able to forget about how I was attired, and I focused solely on the sight beneath me, doing my best to ignore the throbbing inside my cage. I was mesmerized by her beauty and her seductive activities.

Then, still with no sign of self-awareness, she pulled up her bikini top to obscure her nipples. The show was over.

I saw her typing and seconds later the message came through.

“Anon”: “I reward obedience... You will be unlocked at 6 PM tonight... Be back in cage by 9 AM tomorrow... otherwise, you will be sorry...”

A sense of relief washed over me, knowing she was going to unlock me. I then backed away from the window and tore off the bra, keeping the panties on.

oooOOooo

I spent a restless day, waiting for 6 PM to arrive. And the thought of being unlocked at that time, free to have proper erections and to have orgasms, was causing me to become painfully aroused within the limitations of the cage.

As the hour approached, I removed my pants and panties, opened “Keyholder” and pressed “Unlock”. I then waited, counting first the minutes and then the seconds to the deadline.

My pulse was racing, and I'm sure my blood pressure must have been sky high as the final seconds ticked by. Then, precisely at 6 PM, there was a click, and the device sprang apart.

As it opened, I saw a timer appear on the app, counting down from fifteen hours, every second marked off.

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I yanked the cage off, and in relief I fondled my penis, which instantly sported a hard erection. For a few seconds, I considered masturbating in celebration but decided that it was better I went to Nicky's apartment in a state of frustration.

Quickly, I got dressed for my date night, donning boxers instead of panties. Then I set off to Nicky's place, relieved at being free.

oooOOooo

I arrived at Nicky's apartment at 7 PM, and she greeted me enthusiastically, hugging and kissing me.

“I'll fix you a bourbon on the rocks, honey,” she cooed. “Make yourself comfortable.”

Holding our drinks, we sat side-by-side on the sofa. “Expecting any chase-ups from your boss?” she asked, with a grin.

“God, I hope not,” I replied, rolling my eyes. “It'll just be you and me tonight.”

We spent a little time talking and then sat down for dinner. “You don't mind if we eat early? Then we can have an early night,” she explained, with a wink.

It was halfway through dinner when my phone pinged. Nicky heard and, with a look of exasperation, told me to check.

“Anon”: “Tick-tock... Tick-tock... Be a good Kitty and you'll be rewarded...” I felt the color drain from my face.

“Your boss again?” Nicky enquired, visibly agitated.

“Er... yes, but nothing important.”

“She's a damn nuisance, the bitch. Show me what she said!”

“No!”

Yes!” She snatched the open phone from my hand and stared at the cryptic message. “What's she talking about?”

“Er... just a reminder that a deadline is approaching.”

Nah! This isn't work related, is it?”

“Yes, it—”

“Why does she call you Kitty? No boss would call a man that.”

“I... I don't know!” I replied, knowing full well that it was a reference to the Hello Kitty undies that I owned.

“And what's she talking about, rewarding you?”

“Er... consultancy fees, I guess,” I replied, diffidently.

“Why the hell does her name show as 'Anon'?”

“I've... I've no idea.” I was floundering, unsure how to answer this barrage of questions.

“What's her real name?”

“Hmm... Emma,” I blurted out, only seconds later wondering if it was wise of me to disclose her name given the lengths she goes to maintain anonymity.

“Is that the truth?”

“Yes! Yes, it is,” I replied, indignantly.

“How old is she?”

“Er... I'm not sure... about your age, maybe,” I lied. “I've never asked.” I could sense that my face had gone pink and my armpits were becoming sweaty.

“Is she pretty?”

“Well... erm... I've not paid that much atten—”

Liar! Are you dating her?”

No!!” I replied. I was being honest on that point yet economical with the truth.

Nicky eyed me suspiciously. “I think you are, Mark. She's not your damn boss, I'm certain of that. If she were, I reckon she'd respect your free time. If she were my boss, and I received this crap, I'd tell her to stuff her emails where the sun doesn't shine.”

“It's... it's not that easy, Nicky. Trust me, I would if I could.”

She shook her head, while glaring at me. “You're playing two women at the same time, aren't you?”

No! No, I'm not!” I exclaimed, panic building up.

“Your scarlet face says otherwise. You'd better go, Mark. I'm not in the mood for sex any longer.”

“Please, Nicky. There's nothing going on between me and her.”

“Sorry, Mark, but I've told you to go. I don't mind competition, but it has to be open competition. I don't like you acting secretively and lying to me. Maybe we can talk when I've calmed down, but not now.”

oooOOooo

With my tail between my legs, I made my way home. Emma, deliberately or otherwise, had ruined my night.

I made sure to enter the house quietly as I didn't want Emma to know that I'd been kicked out of Nicky's apartment. To have her gloating that she had wrecked my night of passion would be the final straw.

I was so angry with Emma. Had she deliberately set out to interfere?

My only consolation was that I was free to masturbate, and I did so a couple of times. But it was done mechanically, to relieve the build-up I was suffering—I felt no zeal, not even when thinking of Emma or Nicky. Deep down, I was miserable and confused. I was obsessed with Emma but, somehow, I also wanted to win back Nicky's affection.

oooOOooo

After a restless night's sleep, I was up and about by 6 AM.

I knew I had a decision to take before 9 AM. Should I lock myself back into my chastity device, or call the whole thing off, even if that meant finishing with Emma?

I thought it through over breakfast, as I pushed a piece of toast around on a plate, my appetite non-existent. Had I jumped to the wrong conclusion about Emma's motives sending that message? Reading it again, I saw it in a different light. She was probably teasing me, and she had no reason to believe that Nicky would read her email, so it was possibly just an unfortunate accident.

I had come to a conclusion. For better or worse, I decided to lock myself in the cage again. Emma had been kind enough to grant me some free time, and I had no wish to throw her kind-heartedness back in her face. And I knew she was happy to put on evocative displays for me, which would stop if I chose to disobey her.

Therefore, locking myself back into the cage was a no brainer, much as I'd like to have stayed free. I retrieved the bag of frozen veg, shriveled up my penis, and inserted it into the device. With a sigh, I snapped it shut before donning a pair of the cartoon panties that Emma required me to wear.

I took a look at “Keyholder”, and it confirmed I was secured. It was now five to nine. I suspected that Emma would be looking at the app and would see it stated “locked”. I hoped she was proud of my blind obedience and submission to her.

A shiver went down my spine as I reflected that I had locked my penis up with no inkling of when it would next be free. I couldn't believe how much control Emma had over me, both physically and mentally.

A few minutes later, an email arrived.

“Anon”: “You were right to be obedient... I hope you enjoyed your date with Nicole Wilson...”

What the fuck? How did she know where I'd been? How did she know Nicky's name? This was getting scary! Had she followed me? Did “Keyholder” track my movements? Or had she installed another app on my phone in the hour when she'd had it? I had no idea, but I was going to have to be careful.

oooOOooo

Later that day, I phoned Nicole, hoping she might have calmed down from the previous evening.

“Yeah?” she answered, suspiciously.

“Hi, Nicky!” I replied, trying to sound jolly. “I'm phoning to apologize. It's complicated.” That was an understatement if ever there was one.

“What do you mean?”

“I'm sorry I wasn't honest with you.”

“Oh! So, you and this Emma are dating?”

“Not dating as such—”

“I want the truth, Mark! No disingenuous explanations.”

“Right! Okay! Er... she's my neighbor. We've never had sex, nor any intimate contact—you have my solemn word on that—and we never will, but she flirts with me.”

“Hmm... sounds strange. And you flirt back, I guess.”

“Not in the same way, no.”

“But you've not thought to tell her to stop flirting, you moron?”

“Er... no. It's just harmless banter and teasing. She's my neighbor, so I don't want us to fall out.”

“Is she married?”

“Oh, no, she's single.”

“How old is she? I want the truth.”

“Hmm... like I said, she's about your age—”

“Why don't I believe you?”

“Look, it's... it's just a bit of fun. I promise you, we'll never have sex! It's not that sort of relationship.”

“Hmmm?”

“You used to flirt with me when we shared an office, Nicky. It's not dissimilar.”

“It's nothing like. You need to finish with her!” she snorted. “Is that understood?”

“Er... yes, I will tell her to stop flirting. Please give me another chance, Nicky—please. You're the only person I'm in a sexual relationship with.”

She gave an audible sigh, and I could tell she was weighing things up. “I'll think about it and let you know. Bye, Mark!”

With that, the call was closed. There was a glimmer of hope of me renewing my relationship with Nicky but, at the same time, I did realize that I had not given her the true information about Emma. Furthermore, I had no intention of finishing with Emma. I was playing with fire, and I knew it.

oooOOooo

I heard nothing from Emma for the rest of the day. In spite of masturbating the previous night, I was already suffering frustration, and being locked up did nothing to placate my desires.

That night I once again tossed and turned in bed and, when I did eventually fall into a troubled sleep it was not long before I was awoken by a nocturnal erection—or rather, an agonizing attempt at such a feat.

Come morning, I felt knackered, unsure how I was going to cope with being locked up for what was an undefined period.

Again, I had no appetite for food but forced myself to have breakfast. As I did so, my phone pinged. A message had arrived from Emma. Even without looking at it, relief flooded through me knowing that she was communicating with me.

“Anon”: “Your reward for being a good Kitty... 9 PM tonight... outside my window.... strip down to panties... bring phone...”

As I read that curt message, my penis throbbed violently inside its jail. The game Emma was playing was back on. Was she going to unlock me?

oooOOooo

I found it difficult to concentrate on anything as the hours passed away towards 9 PM. Nothing I did could take my mind off what was to happen.

A few minutes before the appointed time, I made my way to her house. It was dark, and the drapes of her ground floor bedroom were closed, as I'd expected them to be. Silently, I removed my jeans and T-shirt so that I was wearing only a pair of lemon cotton panties adorned with a cartoon image of Tigger. My penis was straining desperately inside its cage, and I was praying that she would unlock me. I clutched my phone, my ears alert for the familiar ping of a message arriving.

I glanced at my watch. It was exactly 9 PM and, as I stood facing the window, so the drapes slowly opened like theatre curtains.

Emma was sat in her computer chair, dressed only in a sexy black bra and a matching pair of panties, both embellished with silver threads. I recognized them as something I'd purchased for her a week earlier. Vividly, I was able to recall opening the package and feeling their softness, imagining what Emma would look like, wearing them—now I was seeing for myself, first hand.

Her chair was swiveled around so she was facing the window. She made no eye contact with me and, indeed, was probably unable to see me standing in the darkness. Her eyes were focused on nothing in particular, and she appeared to be in a world of her own. Across her face, was that subtle Mona Lisa smile that I adored.

In her right hand, she held a vibrator. I guessed it was turned on, but I could hear nothing through the double-glazing. Sensually, she used her left hand to pull back on the leg of her panties, allowing access for the vibrator to her pussy.

The instant that contact was made, her body gave a jerk confirming to me that the vibrator was working and was doing its job. I was now in considerable discomfort but there was no sign of me being unlocked. In fact, as both her hands were occupied, there was no way she could manipulate her phone.

All I could do was watch her and, despite my discomfort, wild horses could not drag me away. Expertly, she maneuvered the vibrator around her vulva, manipulating her labia and clit and exploring her vagina. It didn't take long for her to start squirming as the tool activated her sensitive nerve endings. I could see she was mouthing something and occasionally she would take sharp intakes of breath.

As she approached the cliff edge, so her enigmatic smile disappeared, and her face became contorted in a pre-climatic grimace. Then, suddenly, she let out a series of screams so loud that I could hear them. Her back arched and she took on the appearance of someone possessed, almost levitating above her chair.

After a series of powerful jerks, she let out a final gasp and slumped down, the vibrator still carefully positioned.

I watched in wonderment. Then, she withdrew the vibrator and brought the glistening end up to her mouth. She enveloped it with her lips, savoring her secretions.

Seconds later, her free hand reached for a remote and the drapes began to close. Her performance was over, and I was left feeling extremely frustrated, precum now drenching the thin cotton of my panties.

It was with mixed emotions that I got dressed and made my way back home. I was excited that she had rewarded my obedience but dejected that there had been no release for me. There had not even been a message, so why had she told me to bring my phone? Probably to build up my hopes so she could demolish them, I thought.

But, as I was entering my front door, my phone pinged: “Cute panties... Tigger...”

She knew what I was wearing! Somewhere there had been a camera recording me.

Published 
Written by undiecontrol
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