The week leading up to the Halloween party was a torturous mix of anticipation and frustration for Alex. Every glance at Lisa, whether in person or in passing, reignited the burning desire that simmered beneath his constrained desires. The steel chastity belt seemed to amplify every thought and sensation, leaving him constantly on edge.

His balls ached, he couldn’t sleep, he couldn’t distract himself. This was the longest he had ever gone in life without an orgasm, and it was too much to handle. He was constantly leaking precum from his chastity belt, forcing him to change his underwear several times a day.

As the weekend approached, Alex found himself unable to concentrate on anything but the impending party. He wondered what Lisa had in store for him, especially after their teasing interactions.

Four days before the Halloween party, Alex received an unexpected package in the mail. It was large and heavy, and he couldn't recall ordering anything recently. Curious, he brought it up to his room and carefully tore it open, revealing its contents.

Inside, nestled among layers of tissue paper, was a sleek black box. Alex's heart raced with anticipation as he lifted the lid, revealing a note resting on top. His eyes quickly scanned the message:

"If you want to be unlocked on Halloween, make sure you're wearing your costume... ;)"

A rush of excitement and nervousness washed over Alex as he read the note. His mind raced with possibilities. Lisa's playful tease was unmistakable — she had sent him something that hinted at what she expected from him on Halloween night.

Alex held up the costume, a provocative and skimpy prison outfit designed for a woman. The fabric was sleek and form-fitting, hugging every curve, with a tantalizingly short skirt that barely covered what it was intended to conceal. Alongside it, there were matching handcuffs and ankle cuffs, adding a touch of bondage allure to the ensemble.

“Ok… I will just tell everyone the wrong costume arrived, and I had nothing else to wear...”

Alex’s parents would be going to the party dressed as a witch and wizard. They were not pleased with his outfit, clearly stating he was wearing a woman’s Halloween outfit.

Alex responded by nonchalantly saying, “The wrong costume arrived. Who cares? It is just a bit of fun for one night.”

The Halloween party would take up the entire street as people came and went from different houses around the neighbourhood to see each other.

Alex promptly arrived at Jake's house with a mix of nerves and anticipation. The living room had been transformed with spooky decorations, and the air buzzed with laughter and chatter from the guests. Costumed figures mingled, each vying for attention with their creative outfits.

Alex’s parents came to this house first as well. They noted to Alex that there were a few comments about his outfit.

Alex told his parent he didn’t care and then lost them as they got talking to some other parents.

A moment later, Alex's breath caught in his throat as he spotted Lisa across the room, She had chosen to dress as the dominatrix from the movie Jake and him had seen, and she wore the outfit with confidence and allure.

Her costume was a sleek black leather corset that accentuated her curves, paired with thigh-high boots and a riding crop in hand. Her blonde hair was long and wavy, and her makeup was smoky and seductive. His cock strained against the relentless steel, unable to do anything.

Alex couldn't tear his eyes away from her. The sight of Lisa in such provocative attire stirred a mixture of excitement and nervousness within him. He knew tonight would be filled with surprises, especially considering their recent interactions.

Lisa caught his gaze and smiled knowingly. She sauntered over, the click of her heels drawing attention as she approached him.

"Well, well, well," she purred, her voice low and sultry. "Look who showed up."

Alex swallowed hard, suddenly aware of the eyes on them. "Uh, hi Mrs. Johnson. You look... amazing," he managed to stammer out, his cheeks flushing.

Lisa's smile widened, and she leaned in closer, her lips brushing against his ear. "Thank you, Alex. I hope you're ready for a night you won't forget," she whispered, her breath warm against his skin.

Before he could respond, Lisa asked him to show her the decorations in his home, her demeanour shifting from playful to commanding.

"Tonight, you belong to me," Lisa stated firmly as they walked across the street, her blue eyes gleaming with dominance. "You've been a naughty boy, and it's time you were properly disciplined."

Alex's heart raced at her words, a mixture of fear and excitement coursing through him. He nodded silently, unable to find his voice as he gazed up at her with a mixture of awe and desire. His balls and cock were aching in his pants. He couldn’t take much more of this teasing.

They reached Alex’s house, and there was nobody else there. Lisa took her time admiring the decorations before telling Alex to show her his room.

He walked up the stairs and opened his bedroom door, showing Lisa his bed, gaming corner and wardrobe.

"Very nice…now strip!" Her voice commanded, sending a shiver down Alex's spine.

Without hesitation, Alex peeled off his clothes, revealing his naked form to Lida. She wasted no time in securing his wrists and ankles with cuffs, positioning him over the bed with his exposed rear at her mercy.

Lisa traced the tip of her whip teasingly along his back, each stroke sending a wave of anticipation through Alex. Then, with a swift crack, she landed a strike on his bare skin.

"You've been a very naughty boy, Alex. And you know what happens to naughty boys... they get punished," she purred seductively, raining down lashes upon his buttocks.

As the sting mingled with pleasure, Alex felt an intense arousal building within him. Lisa spun him around, forcing him onto his knees.

"Now, make Mistress proud and show her how desperate you are to be released from that cock cage. Worship my ass as if your life depends on it, slave."

Alex buried his face in the warmth of Lisa's latex-clad derriere, intoxicated by her scent and the heat radiating from her body. His tongue explored every curve, diving deep into her most intimate places, a desperate plea for release and approval. He soon drove his tongue as far as it would go up her firm asshole, exploring every inch of her hole, ensuring she knew how sexually frustrated and tuned on he was.

Lisa's moans filled the room, spurring Alex on as he savoured her reactions. Her hand gripped his hair possessively, ensuring his devotion didn't waver. Alex's own arousal was palpable, his desire evident in every eager movement.

The pleasure built until Lisa's climax ripped through her, a cry of ecstasy echoing around them. She turned to him, her touch gentle now as she praised his efforts.

"Good girl," she cooed softly. "You've made Mistress very proud. But the night has only just begun…"

With a playful giggle, Lisa retrieved her stolen lingerie from Alex’s wardrobe, tossing it before him. Her eyes sparkled mischievously as she laid out her command.

"Put these on underneath your clothes. Meet me in forty-five minutes at the garage behind my house. That should give us enough privacy to unlock you. Don't be late," she teased, leaving him to ponder the thrilling commands echoing in his mind.

Alex complied, slipping into the delicate lingerie beneath his outfit, every move tingling with anticipation for what awaited him in the hours ahead.

As Alex cuffed his hands and ankles as instructed, the cool metal of the restraints sent a thrill through him, a tangible reminder of Lisa's control over his evening. With each click of the cuffs, he felt a surge of anticipation, knowing that Lisa held the keys to both his attire and his arousal.

Halfway to Lisa’s house, Alex encountered Jake, who was dressed as a skateboarder, his casual demeanour contrasting sharply with Alex's provocative attire.

“Hey, man! Odd outfit… Did you see my mom anywhere?" Jake asked, eyeing Alex with a mixture of curiosity and discomfort at his unconventional costume choice.

"Uh, no, maybe she's at the Johnstones. There seemed to be quite a crowd there," Alex replied smoothly, masking the rush of guilt and excitement swirling within him. Just moments ago, he had his face buried in Jake's mother's ass, their encounter still fresh in his mind.

"Cool... I'll check there," Jake said briskly, already moving away, clearly eager to distance himself from Alex in his revealing outfit.

As Jake disappeared down the street, Alex hurried on toward Lisa's house, the sway of his hips accentuated by the skimpy prison outfit. The cool evening air brushed against his bare legs, heightening his awareness of every step and the sensation of the handcuffs and ankle cuffs secured firmly in place. His pulse quickened with each passing moment, anticipation building as he approached the next chapter of their daring game.

In the dimly lit garage behind her house, Lisa awaited Alex's arrival with a knowing smile. He appeared, wearing the lingerie beneath his clothes as instructed, his anticipation palpable. Without a word, she motioned him towards a sturdy table in the centre of the room.

"Lie down," she commanded softly, her tone laced with authority and desire.

Alex obeyed, stretching out on the table as Lisa circled him, her eyes gleaming with mischief. She retrieved a set of iron cuffs, securing his wrists and ankles to the table's corners with deliberate care. The sensation of being immobilized sent a thrill through him, his body tensing in anticipation of what was to come.

"Now, my dear Alex," Lisa murmured, leaning over him, her breath warm against his ear, "it's time to release you from that cage."

With deliberate slowness, she produced the key, teasing him with its glinting metal. Alex's breath caught as she unlocked the chastity device that had kept him in agonizing arousal for so long. As the cool air hit his sensitive skin, he moaned softly, his body trembling with need.

But Lisa wasn't done teasing him yet. She traced her fingertips lightly along his inner thighs, inching closer to his throbbing member. Alex squirmed beneath her touch, desperate for her to bring him to release.

"Please," he begged, his voice thick with desire, "please, let me cum."

Lisa chuckled softly, her touch lingering just shy of where he craved it most. "Not yet, my pet," she purred, her lips brushing against his earlobe. "I want to see just how much you can take."

With that, she retrieved a tray of ice cubes from a nearby cooler. One by one, she dragged them teasingly across his heated skin, sending shockwaves of cold pleasure through his body. Alex gasped and writhed against his restraints, the contrast between heat and chill driving him to the edge of sanity.

She slowly unzipped her pants, revealing a glimpse of her arousal as she straddled Alex. His heart raced with anticipation, expecting her to take him, but instead, she positioned herself above his face.

"If you want to cum, you're going to have to earn it," she teased, her voice thick with desire.

With that tantalizing command, she lowered herself onto Alex's eager mouth. He couldn't believe his luck, his senses were overwhelmed by the intoxicating scent and taste of her dripping sex. Without hesitation, he immersed himself in worshipping her, cherishing every delicate fold, and channelling all his pent-up desire into pleasing Lisa.

She moaned deeply, her fingers gripping his hair firmly, guiding him deeper into her ecstasy. Occasionally, she would release his hair to stroke his throbbing cock teasingly, driving him to the brink but withholding the release he desperately craved.

Rocking back and forth, she closed her eyes in bliss, riding his face with an intensity that pressed his head between her thighs. Alex was consumed by the heat of her arousal, feeling her every movement reverberate through him. It was an inferno of sensation; the hottest experience he'd ever known, yet his own need remained unattended, his balls tight with longing.

Lisa's pleasure built relentlessly until she finally collapsed onto him, convulsing with orgasm after orgasm. Her entire body trembled with the force of her release, and Alex drank in every moment, intoxicated by her satisfaction and his own denied yearning.

Lisa climbed down from the table and steadied herself for a moment.

She then smiled devilishly and leaned in, her lips brushing against his ear once more. "You've been such a good boy, Alex," she whispered, her voice low and husky. "But good boys don't always get what they want."

Before he could protest, she watched his cock and balls incredibly hard. He let out a yelp, but she achieved her goal.

His erection had gone down and she expertly reattached the chastity cage, locking him back into sweet agony. Alex whimpered at the sensation of confinement once more, his arousal still painfully evident.

Lisa kissed his forehead tenderly, her fingers trailing lightly over his flushed cheeks. "Don't worry, my dear," she murmured reassuringly. "There will be more opportunities for you to please me. The Christmas party will be here before you know it, and I might give you the best Christmas present you have ever had..”, she said as she teased his balls as his locked cock squirmed.

With that promise hanging in the air, she began to release him from the table, her touch gentle and affectionate. As Alex stood, still trembling from the intensity of their encounter, Lisa reattached the key to her necklace.

She led Alex through the house and then said goodbye to him at her doorway.

Alex arrived back home in a daze. He had just spent Halloween worshipping his best friend's mom’s ass and pussy… His balls and cock ached. His ass was red and sore from the whipping.

The Christmas party can’t come soon enough. She has to let me cum at some point…right?