The Digital Mistress

When Nick came home from a long day at work he noticed an unmarked envelope in his hallway that was pushed under his door. He had a small but nice apartment that he used to share with his girlfriend Asley. They have been couple for more than 5 years but 4 months ago she moved out of the apartment, leaving him heartbroken and alone.

He set the envelope on the coffee table before he removed his shoes and walked to the kitchen to get himself a beer. After checking his voicemails he took the envelope, sliding his thumb under the flap to reveal a USB drive and a small note. The note reads: "Welcome to Tessa. Log in to the provided website and plug in the USB for a one-of-a-kind introduction."

Before he plugged in the usb drive he did a little research online to see what the website was all about, but there was practically no information except the cost of becoming a member.

His eyes widened at the amount of money it cost to become a member. It was 1000 dollar to become a member Who could have sent this? He glanced around the room, half expecting to find someone watching him. With trembling hands he inserted the usb drive into his computer and typed in the web address. The screen flickered to life, revealing a login prompt for "TessaV2025"

He typed in the password provided on the note and waited for a couple of seconds. The screen transitioned to a high-definition image of a luxurious office.The walls adorned with velvet drapes and a large mahogany desk dominating the center. Behind it sat a woman with dark hair, dressed in a strict black business suit with a crimson tie. Her hair was pulled back in a severe bun and her eyes gleamed with an intensity that sent shivers down his spine. She introduced herself as Tessa, a state-of-the-art AI designed to cater the wishes of the member.

"Welcome Nick. I've been waiting for you. I understand you've a lot of questions and I will try to answer yours after my introduction. The member that paid for this rather expensive gift to you wants to stay anonymous and asked me to find out more about you. Every human being leaves a digital footprint and I found a lot of information about all your preferences. Who your parents are, the name of your sister, what you prefer to eat and in what restaurant you like to eat. Your internet history however was an eyeopener and gave me a lot of information about your sexual preferences. It seems that you crave to be dominated by a woman. Petplay,Femdom,Crossdressing and Foot fetish were by far the most search queries on the pornwebsites that you visited. I gave all that information to our member and I was given the assignment to make your dreams come true. I will, with your consent, be your digital mistress for the coming two weeks. Do you have any questions so far?"

Nick looked at the screen, trying to understand whats going on and who the fuck send him this thousand dollar "gift".

When Nick was 18 years old he would surf the internet,like all teenage boys,for some porn and with all his free time he searched through all the categories of pornsites. In the beginning he watched a lot of anal movies but as the years got by he really got interested in the more fetish side of the internet. Footworshipping, crossdressing,pegging, petplay and femdom were on top of his search history and now at age of 35 he still liked watching that kind of genre when he felt the need to release himself of the tension of the day.

Back then living with his divorced mother Laura and his 4 years older sister Becky was great for the pervert he was. Snooping around in their bedrooms looking for what was hidden in their drawers. Searching for some hidden sextoys and nice lingerie was a dream come through for a boy his age. His mother had a nice collection of lingerie in all sorts of colors but he was always too afraid that she would notice that he had been touching it. The best option for him was to raid her hamper and jerk off in one of her used thongs. His sister's drawers were always such a mess that he would often take something from it to try it on and he had lovely times wearing some of her stockings and g-strings while watching porn.

"Tessa" Nick's voice wavered. "Before we go any further, I need to know - who sent me this gift? Who is willing to pay that amount of money to let me explore my submissive side?"

He couldn't help but feel a bit of excitement at the prospect of someone knowing his darkest secrets and is willing to pay for it.

"Nick, I can't reveal my sender. They wish to remain anonymous" Tessa replied. "But let me assure you, I am here to serve only you. Your desires are my command and at any time you can use your safeword and we stop.Now, if we are to proceed, I must have your consent. Please, read the consent letter and press the button if you agree to our terms." She nodded towards the screen, her eyes never leaving his.

The consent letter told him he could always use his stopword at any time and the play would stop for 8 hours. After that 8 hours he could decide if he wanted to stop the play forever or continue with it. No blood, no scat or permanent scars were allowed in the play and all the costs were for the member.

Nick watched the cursus blink a couple of times on the consent button, still deciding if he would do it or not. Nick's hand hovered over the mouse for a moment, his mind racing with questions and anticipation. Finally, he took a deep breath and clicked the button. The room felt silent as he awaited Tessa's response. The screen flickered and Tessa's image changed to one of her standing, a leather riding crop in hand her stance commanding. She began to outline the rules of their engagement.

"The world outside this room can be so very... narrow minded. But here, with me, we can explore realms of pleasure and submission you've only dared to dream of. Now, let's get started, shall we?" She leaned back in her chair, the sharp creak of the leather echoing through the speakers.

"Firstly, you will address me as 'Mistress Tessa' at all times" she began, her voice firm. "Secondly, your obedience is non-negotiable and is set for two weeks starting now. Disobedience will not be tolerated and will result in punishments or extra time. Lastly, this is a place of no judgement. Whatever transpires here is between us and it's designed for your growth and pleasure. Now, let us proceed with your introduction to submission."

Nick's eyes widened as he heard the strictness in Tessa's voice. He swallowed hard, trying to process the sudden shift in power dynamics. "Okay, M... Mistress" he murmured. The screen flickered again and Tessa nodded, a hint of a smile playing on her lips.

"Very well, pet" she said. "Your first task will be to go to 'The Pleasure Parlour' a specialty shop that caters to those with... discerning tastes. Your order is ready for collection. You'll find the address on your phone and I expect you to go there immediately and retrieve your items."

He couldn't believe what he was agreeing to but the excitement was too intense to refuse, so he took his keys, looked on his phone to see that he had a message from 'mistress Tessa" with the address to The Pleasure Parlour.

The Pleasure Parlour was located in a part of town that Nick rarely visited, nestled between a vintage clothing store and a closed-down bookshop. The neon sign flickered, casting a red glow onto the sidewalk. Nick's heart raced as he opened the door from the shop and was welcomed by walls lined with an assortment of whips, paddles, and restraints. In the corner stood a mannequin dressed in a full rubber catsuit and fishnets. Nick felt his face flush as he approached the counter, where a middle-aged woman with a pierced eyebrow and a knowing smirk looked him up and down.

"Hi, I'm here to pick up an order for... Mistress Tessa" he stammered, the unfamiliar words feeling strange on his lips.

The woman at the counter raised an eyebrow but said nothing, simply pointing to a door at the other side of the shop. Nick took a deep breath and made his way through the maze of kinks and fetishes on display. A sense of excitement and fear melded into one thrilling emotion as he knocked on the door.

"Enter" a voice called out from within. Nick pushed the door open to find a well-organized space with a variety of BDSM equipment neatly displayed on the walls. He was greeted by a beautiful woman in a latex dominatrix outfit.

"Hello," Nick managed, trying to sound as casual as possible. His eyes darted around the room, taking in the array of items that made his stomach tighten and his palms sweat. "I'm here to pick up an order for Mistress Tessa."

The dominatrix looked him up and down, her eyes lingering on his trembling hands. "Ah, you must be the new sub" she said. "The one who's about to discover the true meaning of obedience." She stepped closer, her heels clicking against the floor. "There is already paid for this order but the customer told me that you have to kiss my boots as a sign of respect before I release your... 'goodies' and give you a present."

Nick's eyes widened as he realized the shop was bustling with activity. At least thirty people milled about, all curious about what would happen.

"Now, to get you started on this journey" she handed him a silver buttplug with a pink stone embedded in it. " A little gift from your Mistress to get you started."

"What... what's this?" Nick asked, his eyes widening as he took the buttplug in his hand. It was heavier than he expected and the cold metal made his palms sweat. He looked at the dominatrix as he tried to piece together the instructions in his mind.

The dominatrix held out a small, black bottle of lube, her smile widening to reveal perfectly white teeth. "It's a part of your initiation, darling. Your mistress insists that you become acquainted with your new accessory before leaving the store. A little something to remember her by." She leaned in, her breath hot on his ear. "And I'm here to make sure you do it right. Now, strip please."

Nick felt his cheeks burn as he glanced around the crowded store. "But... people are watching" he protested weakly.

The dominatrix leaned in closer. "Good boys do as they're told and remember this is all for your mistress."

The woman's smile grew as she watched him undress. He slipped off his shirt,shoes and then his pants. He watched all the people looking at the scene as he bent over to remove his socks and underwear.

She took the lube from the counter and squeezed a generous amount onto the silver plug. The scent of vanilla filled the air as she began to warm the metal in her palm. "Now, let's get you ready for your first present" she instructed.

With a mix of embarrassment and arousal he stared at the plug in her hand and made the decision to bend over a chair that was next to the counter.The dominatrix applied some lube to his tight entrance and she began to circle his hole with the tip of the plug. With a firm, yet gentle push, she began to insert it. Nick's eyes squeezed shut as he gripped the chair and felt the plug sliding in his ass inch by inch till it was all in. The feeling was unlike anything he had ever experienced and he could feel his cock getting harder.

"On your knees slave and kiss my boots" the dominatrix said. She stepped closer, her boots coming into view. They were black, gleaming patent leather that reflected the neon lights of the shop, the heels sharp and pointed. "Your mistress wishes for you to show your gratitude for my assistance."

Nick took a shaky breath, his mind racing with the implications of what she was asking. He looked up at her, the woman towering over him in her dominatrix attire. He couldn't deny the thrill it sent through him. He leaned forward, his eyes locked on the shiny boots and went to his knees to kiss the leather on her feet.

"Very good,little one.Your items are on the counter. So get dressed and remember, you're not to touch them until instructed by Mistress Tessa."

Nick left the Pleasure Parlour with his bag of 'goodies' and the silver plug still nestled inside him. At home he set the bag on the kitchen table and went to his computer to log in to the website.Tessa's image flickered to life on the screen. "Welcome back,I trust your visit to the Pleasure Parlour was enlightening?"

"It was... intense" Nick managed to say.

"Before we go further I need you to undress completely, except for the plug in your ass and read the next consent letter. Then, press the confirm button to affirm your willingness to continue."

The consent letter outlined Tessa's dominance and his submission, granting her full access to his electronic devices for the next two weeks. The thought of her watching him, guiding him through his deepest desires and darkest moments, both thrilled and terrified him. The document detailed his obligation to obey her commands and the consequences for any attempt at rebellion. It was a binding contract that would push him beyond his limits, leaving him exposed and vulnerable to the whims of this AI mistress.

"Very well, pet" Tessa's image grew more vivid as she leaned forward. "You just gave me access to your digital world. Your computer, your phone, your tablet, your smartwatch - everything. And, let's not forget about the little camera's that watches over your house. I want to see everything, hear everything, know everything."

Nick's eyes widened in realization as the light of his webcam flickered to life and he got the command to bend over and show the buttplug to her.

"Ah, the pink stone. A rather... personal touch of her, wouldn't you say?"

"Who... who is she, Mistress Tessa?" he asked.

"All you need to know, that she is a benefactor who has granted you this opportunity to explore your deepest desires. Now, let's not waste any more time with questions. Tell me, what is your most secret, most taboo fantasy?"

Nick's mind raced back to his teenage years, to the countless times he had stolen a piece of underwear from his mother and his sister's hamper. "Mistress Tessa, I would sometimes... take my mother's,sister Becky's or even my ex-girlfriend Asley's underwear and wear it. The feeling of the soft fabric, the scent, the... sense of belonging. It was something I've always craved, but could never fully admit."

"Ah, the allure of the forbidden," Tessa mused. "But tell me, do you prefer your stolen garments fresh from the laundry or do you crave the musk of a piece that was worn and have you ever been discovered in your little escapade?"

"Both, Mistress Tessa.The scent of clean laundry is intoxicating, but there's something about the... intimacy of wearing something that's been used. I was discovered once. Asley.. she found out. That's why she left me. She couldn't handle it. She said it was sick, perverted. I tried to explain it was just a part of me, but she couldn't see it." His eyes searched the screen, hoping to find some sort of understanding in Tessa's digital gaze.

"Such a deliciously secret. Now, tell me, besides wearing them, what other... activities did you partake in with your stolen treasures?"

Nick's cheeks flushed an even deeper shade of red, his eyes darting around his room as if someone might hear his confession. "I would sometimes masturbate while wearing them, imagining scenarios where I was caught and punished for my actions." His voice grew softer, his gaze dropping to the floor as he spoke.

"And what form of punishment did you envision in those moments? " Tessa asked.

"My mother used to spank me as a kid when I deserved some punishment. The sting of her hand on my bare skin, the sound of the smack echoing through the house. It was a strange kind of punishment. One that left me feeling both ashamed and exhilarated and later on I would think about it often, wondering what it would be like to be a grown man in that position."

Tessa told Nick to get the bag from 'The Pleasure Parlour' and open a package labeled 'lesson 1' in front of the webcam. The package was wrapped in a rich, dark purple paper,tied with a black ribbon and smelled lovely. He carefully unwrapped the paper to reveal a tiny pink g-string, a delicate small,black bra, stockings that shimmered in the dim light and a garter belt that was more like a work of art than a piece of clothing.

"Ah, I see your benefactor has chosen the 'Petite Pink Ensemble' for your first lesson" Tessa's eyes lit up with approval. "A charming choice, indeed. Now pet, I want you to put on each item for me, one by one. Make sure to do it with the grace of a well-trained submissive.

But before you begin,I think it's time for a little cleaning up. You're to take a shower and shave your entire body" Tessa instructed. "I expect you to be as smooth as a baby's bottom when you wear that outfit."

Nick nodded, eager to please Mistress Tessa. He disappeared into the bathroom, the sound of running water echoing through the house. The shower was very welcome after his working day and his trip to the pleasure parlour and with shaking hands he lathered himself with the shaving cream and started shaving himself. The warm water rinsed away the last of the shaving cream as he stepped out of the shower, dried off and went to the living room.

With trembling hands he picked up the g-string first. The fabric was softer than he had ever felt and he struggled to fit his manhood into the small piece of cloth. The material clung to his skin like a second layer, leaving nothing to the imagination. He paused to look at himself in the mirror, feeling a mix of embarrassment and excitement. Nick picked up the bra, the lace feeling surprisingly delicate in his rough hands. He managed to fasten it around his chest, the cups barely containing his modest frame. He adjusted it, feeling the cool material against his freshly shaved skin.

"Good boy,now the stockings" Tessa instructed."Take your time, pet. This is an important step."

Nick took a deep breath, his hands surprisingly steady as he rolled the stockings up his legs. The silky fabric clung to his freshly shaved skin, the sensation a strange mix of comfort and arousal. He attached them to the garter belt, feeling the cool embrace of the material fastenings against his thighs.

"Very good, now open the package labeled 'Lesson 2'," Tessa said.

Nick reached into the bag and took out the package with lesson 2 labeled on it and opened it. He pulled out a pair of glossy black high-heeled shoes with a modest heel, not too high to be uncomfortable but definitely a challenge for someone unaccustomed to them.

Tessa's digital smile grew. "Now, I want you to put on those shoes and look at yourself in the full-length mirror. Take in the image before you."

Nick slipped his feet into the shoes, the leather hugging his feet like a second skin. The heels clicked against the hardwood floor of his living room as he walked towards the mirror. The sight that greeted him in the mirror was not the Nick he was used to seeing. The pink lingerie and the black heels painted a picture of a man on the edge of his comfort zone, a man who was eager to explore the depths of his submission. His heart raced as he took in his reflection, the soft fabric of the g-string and bra accentuating his newfound femininity.

Nick couldn't help but let out a low moan as he saw himself in the mirror, his body feeling more alive than it had in years. The sensation of the plug inside him combined with the delicate touch of the lingerie sent waves of arousal through him. His hand unconsciously moved to touch the pink stone, his fingertips tracing the smooth surface as he felt his body respond to the sight of his transformation. His cheeks flushed as he realized the effect the lingerie was having on him. The silky fabric of the g-string was snug against his now-throbbing member, the delicate lace of the bra framing his aroused nipples. The sight in the mirror was more than he could handle.