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Rated: 18+ · Interactive · Other · #1870046
Joe has agreed to some online dares from a sexy middle aged woman online. What happens?
This choice: He is late and his punishment is having to streak the neighborhood  •  Go Back...
Chapter #3

He is late and his punishment is having to stre...

    by: Stacey Shackleton Author IconMail Icon
Miss Christy stood in front of Joe and indulged him with a smile.

Joe's nervousness was etched on his face, and as he looked at the clock, Miss Christy could tell he was desperately trying to remember when he'd started.

She took a couple of steps forward, until she was right in Joe's face, and held his chin in one hand. Gazing deeply into his eyes, she studied the way that fear seemed to mix with excitement and embarrassment. The man was trembling slightly at her touch. Miss Christy ran a single finger down his neck and started to playfully dance around his naked chest, lightly touching each nipple, before letting the finger continue it's downward journey.

As it passed over his stomach, she stopped momentarily to toy with his belly button, but never let her finger rest on one spot for too long. As she held his gaze, she could see the embarrassment well up even further, as he began to anticipate where the finger would end up next. Still, hiding behind that embarrassment Miss Christy could tell there was the raw animal desire for her continue.

“Do… Do you want me to continue… further down?” Miss Christy whispered, almost breathing the last few words into his ears. She senses the trembling intensify, and Joe was now rock hard. When he opened his mouth to speak, several seconds passed before he was able to get the words out.

“Ye….. yes…” he stammered, his flushed red cheeks at odds with the desperate yearning now evident in his eyes.

“Well then…” Miss Christy replied, beginning to trace a line from his stomach to his crotch with agonising slowness, “perhaps you should…”

She suddenly flashed him a look of total domination, and instantly ran her nail up his front, placing it firmly back on his chin.

“Perhaps you should have remembered to address me properly!”

The slap wasn’t hard, but it was a shock, and Joe gasped.

Miss Christy, turn on her heels, and walked around Joe until she was directly behind him.

“Next time you will remember to address me as Miss Christy!”

This time the slap to the ass was harder, and propelled Joe forward half a step as he reacted too slowly to regain his balance.

The stern disciplinarian in her voice reverberated harshly in this ear. However, when she spoke next, her voice was suddenly light and friendly again.

“Still,” she said, “I must say that you did very well with the chores! I completely expected you to take three hours!” she almost purred the last part. “And you know what, it only took you two hours and fifteen minutes!”. She could feel Joe lose some of the tension in his shoulders as he breathed a sigh of relief. Didn’t that mean he’d finished in time?

Miss Christy leant in again until her lips were practically resting on his ear. He could almost feel her red lipstick brush against the skin of his neck.

“Such a pity then…” she breathed, almost too quietly for him to hear, so that he had to strain to listen for every syllable. “Such a pity that I only gave you two hours to complete them all!”

She didn’t spank Joe’s ass this time. Instead, she held it firmly in one hand and gave it a squeeze until he stood up on his toes in a futile attempt to escape her grasp.

“Now, now. You were warned. Nobody can say I’m not being fair, can they Joe?” she asked, almost innocently.

“No….” Joe said, trying to control his voice, and remembering at the last second to address her properly. “No Miss Christy. I was warned!”

“So what must I do now Joe?” Miss Christy asked, almost sounding puzzled as to what could possibly be expected of her next.

“You must give me a penalty!” Joe replied, his voice barely holding together and his eyes shut tight.

“What?!” Miss Christy said loudly, now taking a firm hold of his bottom with her other hand and pinching him hard.

Joe tried to think of what was expected of him, and through the strangely erotic sensation of this woman groping his bottom, a flash of inspiration struck.

“You must give me a penalty, Miss Christy!”

“Ahh…” Miss Christy replied, letting her grip loosen and allowing Joe to return to resting back on his heels. “Well,” she continued, almost with a sigh, “you’re quite right of course.” Letting go, she aimed a light, playful slap at his helpless bottom, and came around to face him again.

“And luckily, I know something you can do.” she studied him closely with a serious expression on his face. “I have a couple of things that need delivering to a couple of my neighbours. Simple invites.” She saw a flash of panic pass over his eyes. “Oh, don’t worry, you can simply leave them in the letterboxes” she continued, with a merry glint in her own eyes.

For a second that seemed to calm Joe, and that - Miss Christy reflected - simply wouldn’t do. As Joe’s mind swam with possibilities though, Miss Christy saw a question form in his mind even before he opened his mouth. “Well?” she asked, eyebrow raised, pre-empting him slightly?

“Miss Christy. Will I be delivering this without anything to wear?” Joe gulped.

Miss Christy walked back and forth before Joe slowly, always maintaining eye contact. She knew the internal conflict that Joe was fighting in his mind. The desire to be given something to wear, to protect his modesty, to save him from having to be outside completely naked. And yet, at the same time, the desire to be denied clothing, to have his modesty ripped from him, to be thrown outside naked and not allowed back until he’d completed his task.

Well, Miss Christy though, she was nothing if not accommodating. She laughed lightly.

“Oh Joe, seriously? You’d think I’d send you out there with nothing to wear? Really? What must you think of me!”

Miss Christy laughed again, and Joe seemed to join her with his own nervous laugh. Miss Christy looked at Joe and secretly wondered whether he was more relieved than disappointed, or whether the need for embarrassment had truly taken him yet.

“No Joe, I have something for you to wear. I’ll go get it right now. You just be a good man and wait here.” Miss Christy turned to leave the room, and then appeared to stop and think better of it. Turning back to face Joe, she raised a finger up in thought, and then seemed to go “aha!” as if to indicate she knew what was wrong.

Joe was standing up straight, feet together, arms by his side, penis at full mast out in front of him.

Taking Joe gently by the hand, Miss Christy guided him over to a window overlooking the street, and then forced his legs apart. Stepping back to admire her handiwork, Miss Christy seemed to nevertheless find something critically wrong with her art display, and quickly stepped back to Joe again. Taking his hands, she placed them both on his head, so that he looked as if he was deliberately exposing himself to anyone who walked past.

“Great!” she said, seemingly now content with the arrangement. “Now, you just wait there, I’ll be right back. You’ll be going to numbers 45 & 37, so maybe you should have a look outside and figure where they are!” she added helpfully.

Joe groaned slightly, and seconds seemed to stretch into minutes while Miss Christy disappeared from sight.

Nonetheless, eventually he did hear her return, and of the two people who had walked past while she’d been gone, he couldn’t be absolutely certain that either of them had witnessed his lewd display.

“Right.” Miss Christy said, her voice all business. “Now, open your mouth and I’ll put the first invite in for you to hold in your teeth.”

Joe was shocked. “But Miss Christy, why shouldn’t I just hold it in my hands?” he asked.

“Well, you’ll hardly be able to do that, _and_ wear what I have for you, now will you?” Miss Christy replied, seeming shocked and put out herself.

“Wh… What, I don’t understand.” Joe said, before hastily adding a “Miss Christy” at the end.

“Well young man,” Miss Christy continued smoothly, seemingly choosing to humour Joe’s bizarre question about his hands, “I’m hardly going to let you go out there without anything to wear. You… do want something to wear, don’t you?” Miss Christy asked, with a doubting undercurrent in her voice.

“Ye… yes. Miss Christy.” Joe said, although not entirely convincingly.

“Well, good.” said Miss Christy. “And since I’m asking you to deliver, it’s only fair that I deliver for you.”

Joe was confused again. Miss Christy didn’t seem to be carrying anything that looked like clothes. Was she going to make him dress up in what she was wearing? He couldn’t make any sense of what she was saying.

And then, slowly, Miss Christy reached behind her and seemed to extract something that was hooked to the back of her skirt. Something she’d found in the other room, and had been waiting to reveal to Joe.

Joe’s eyes bulged slightly at the sight of the object, and his breathe quickened at the implications.

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