Jessica and Tom 03: A Sub-maid's Tale

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The couple attend their first event.
15k words
4.82
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Part 3 of the 4 part series

Updated 06/12/2023
Created 06/03/2022
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The party - part 1

Jessica had purposely told Tom very little about the party. She knew that it may intimidate him if he knew quite how 'alternative' the festivities were. All he knew in fact was what he'd be wearing and that they were going to a party. Without a doubt his mind would have joined up the dots and assumed there would be a significant amount of domination and submission but to what degree she left to his imagination. All he knew for sure was he needed to be game ready for 6pm when the driver would pick them up.

Jessica had left the latex oriental dress they had bought on their previous shopping trip hanging in his room along with a note.

'Be ready by 6pm, the colour is red, be slutty but demure and be ready to serve'

He noticed the blond wig was also out sitting on a mannequin head. The wig had been carefully tied up into a tight ornate bun at the back, a departure from Jessica's usual preference for carefully coiffed flowing curls. He slipped the wig over his head and set to work preparing the eyeshadow palettes he thought would go with the cryptic message.

After some considerable time fiddling with red eyeshadow shades and comparing them he decided to go back to basics. Red eyes and red lips would be too much he thought so why not try for something simple, elegant but with a hint of slut.

He worked with neutral shades over his upper lids and kept them light before adding a glittery final shade to jazz up the look. He then took his liquid eyeliner and made an ambitious large wing to give his eyes a catlike quality. Then used a deep burgundy liner along the top of the eyeliner to show he had listed to Miss Jessicas choice of colour. Next he applied a thick layer of foundation and concealer to give himself a flawless finish before contouring and highlighting heavily to give him back some colour. A liberal application of bronzer gave a slutty shimmer to his cheeks. Finally he took the red lipstick they had bought together at the mall. The lipstick was soft and creamy as it went on drying to a deep velvety matte finish and it matched his dress perfectly

His lingerie was then next choice he needed to make. He knew he'd likely be in very elegant company so needed to find the balance between classy and sex kitten. He chose a tight black lace and red silk corset with subtle flush boning and clasps so it didn't show too much or damage his dress. He fussed with the thick garter straps as he fastened them to expensive lace topped fashioned stockings and tightened them to keep the tops in just the right spot. A pair of matching black lace and red silk g-string panties completed the look.

He slipped carefully into the latex dress already having undone the 5 black poppers along the shoulder. He pulled it over his hips and slipped his arms into the short sleeves then used the mirror to straighten all the lines before doing up the poppers relishing the tight feeling of the rubber on his smooth skin as it warmed and clung to his body like a second skin. He grinned at the fetish doll he saw looking back at him in the full length mirror. The corset showed through the thin latex giving more than a hint of what lay beneath. Had he been able, his cock would have been bulging at the thought of those cock sucking lips slipping over his shaft.

Finally he found a pair of simple black stiletto heels with a cute ankle strap. His feet slipped into the smooth leather and he felt the muscles in his calves tighten as he adjusted his posture to the angle of the shoes, the stockings emphasising his good muscle tone. He slipped his lipstick and a few other essentials into a small red clutch bag, relatively sure he'd need to do more than a light touch up throughout the evening.

At 5:50 he clip clopped down the stairs and into the kitchen to await Miss Jessica. He heard the click of her heels on the stairs just as he sat on one of the stools. As she appeared in the kitchen door way he sat in awe of her radiance.

"How do I look?" she asked enjoying his adoring gaze as she gave him a twirl. Her black satin gown hugged her curves and shifted allowing light to shimmer off the material as she moved. The plunging neckline showed off her amply supported cleavage and Tom could see the telltale shape of a corset beneath. The dress hugged her tightly over her hips until the top of her thighs where a long slit allowed her long legs to show in their glossy black stockings. Her boots were shiny patent leather, knee length and laced from the instep to the top of the boot, the ample heel gave her an imposing height advantage despite his own heels. Her shoulders were covered with a luxurious thick black fur scarf and her arms clad in black satin opera gloves.

Her raven hair rolled in large curls over one shoulder lustrous in the bright lights of the kitchen. She had gone with a very dark palette for her makeup. Her eyes were dark and smokey with heavy eyeliner, thick false lashes and mascara. Her lips were a deep matte burgundy and her cheeks sported a similar dark burgundy blush giving her a bold and powerful presence.

Tom sat openmouthed unsure how to articulate what he thought.

"Speechless I see, excellent!" She chuckled. "Sweetie you've definitely hit the spot with your outfit, let me see." Tom immediately stood and gave her a twirl.

"I hope its what you wanted, I had such a hard time with the eyes, just couldn't figure out a colour then decided to go for a sort of pinup look."

"Its perfect sweetie, you'll definitely turn some heads tonight, I've got a few final accessories for you in the car though. Shall we go?" Tom quickly fell in behind her as she headed for the door.

At the door she pulled a heavy deep red cloak from the closet and passed it to Tom "it's cold out." she said as she slipped it over his shoulder and fastened the clasp at the neck and adjusted the large hood so it hung just right behind him.

As always the Mercedes purred at the curb the driver stood at the open door and the couple slipped into the sumptuous leather seats. As soon as he was belted in Tom slipped into his usual daydream but she needed him to listen so she could explain the rules of the evening

"Shake a leg." she said bluntly and Tom fluttered his long eyelashes as he returned to the moment.

"Good boy, I need to explain how this evening is going to work, there are only a few things you need to know but they are important. As I'm sure you've guessed this is a fetish party, but its run by a well established group of female dominants so its a bit more than just a big orgy." she explained. "You'll find its quite classy, at least to start with but there is very much a hierarchy. I assume you've seen, read or at least heard of 'a Handmaids tale?"

"Yes Miss Jessica, it was excellent."

"Good, this should be fairly straightforward to explain then. We've flipped things about, men are obviously not the stronger sex in my world. Women in black or black and white are the ones in charge. You will obey their instructions as if they were my own do you understand?"

"Yes Miss Jessica of course."

"How do you feel about being played with by others without me being there?"

"I'm not sure Miss Jessica, I guess it depends on who they are and what they expect of me."

"You have my word no one will harm you but they will test your limits I'm sure, you remember your safe words don't you sweetie?"

"Yes Miss Jessica, Tomato for Stop and Banana for slow down"

"Excellent. but as you are not sure lets play it safe to start with and stick with play only while under my supervision." She slipped a yellow leather bracelet around his wrist and fastened the delicate clasp with a click. He looked at the bracelet and saw 'OfJessica' inscribed on the shiny metal clasp which showed no obvious means to remove it.

"This shows others that you are only to be played with when I am present or if you give consent, 'OfJessica' is your name for tonight as you are mine and so 'Of Jessica' just like the Handmaids tale."

"Yes Miss Jessica." he nodded admiring the expensive looking leather and shiny metal of the bracelet.

"Now, moving on, the people in turquoise are visiting dominants, both men and women, they are to be treated with the utmost respect but you are only to obey their instructions with my supervision. They are our guests but are there to watch only unless invited to participate."

"Ladies in bronze are to be referred to as Aunt. They are dominants in training and will be obeyed implicitly when a Domme is not present but will never engage in play without your Domme inviting them to. You might recognise a few from our outings, Miss Sarah for example."

Tom nodded as each class was described and tried to take in the information without being distracted by Jessica's enchanting beauty.

"Anyone in red is a submissive like you my love, you are all our 'sub-maids'. If they wear a collar they are owned, if not, like you, they are yet to undertake to be owned but are still betrothed to their Mistress otherwise they wouldn't be there. You can expect to be quite intimate with some of them through the course of the evening. They will all have similar bracelets to you, coloured either green, yellow or red"

"Finally anyone in blue are serving staff, they are well aware of the kind of function this is and have seen it all before. They are trusted individuals but are only there to serve drinks and food not partake in the events."

"This is my chance to show you off and I cannot wait to do so my sweet. Its your chance to impress my sisters and ultimately see if this is a lifestyle you want to continue with. The night will be highly sexual as always but know I will never allow any harm to come to you." with that she reached in and kissed him tenderly, he relished taste of her lips as he allowed her tongue to delve deep into his mouth and coil with his own.

The limo slid into the ornate gates of the country retreat and crunched down the gravel driveway, this was the first time Tom had been fully aware in the car, they had chatted like a normal couple during the 45 minute drive. She was delighted to see he seemed to be not just accepting of his role as her submissive sissy but seemed to be enjoying it. He was less tense and seemed happier than when they had first met now that he didn't need to worry about the stresses of life.

As they entered the driveway she asked the driver for the box that lay on the front seat. Opening it she took out what looked to be a white arc of stiff white material. She handed it to Tom, "These are your 'wings', a type of bonnet, all the submissive will be wearing them or a variation of them. It limits your field of view and signifies your submissive position. You will wear them at all the formal parts of the evening unless you are told otherwise."

"Yes Miss Jessica." he obediently slipped the bonnet over his head and as she had said he found the elongated rigid arch limited his sight to what was right ahead of him.

The car pulled up to the white steps that lead into the huge country house and the doorman in a perfectly tailored blue suit opened the door and extended his hand to help Jessica out then repeated the gesture for Tom then lead him to Jessica's side where she took his arm. The limo quietly crunched away on the gravel as they walked up the steps towards the gentle sounds of laughter and music that spilled from the large open doors.

The Party - Part 2

The delicate notes of a string quartet drifted through the room as the guests mingled and caught up with each other much like any formal event. Having left his red cloak at the door Jessica clipped a golden chain leash to Tom's amber bracelet as they entered the main hall. Around a hundred people dressed in everything from expensive designer ball gowns to very revealing lingerie and even one in an all in one pvc body suit with a horses head and saddle draped with crimson straps and saddle blanket showing they too were a sub-maid. Often the outfits for the sub-maids were subtle at first glance but overtly sexual when fully revealed.

A splendidly dressed older man stood in a deep red velvet suit stood obediently at the side of his elegant mistress with his head bowed as she chatted to another exquisitely dressed younger lady in a flowing turquoise ball gown. As they passed Tom glanced back to see the back of the jacket cutaway in the shape of the word 'Slut' showing the gentleman's bare back covered in welts from what looked to be a recent caning. His trousers were backless and revealed his naked and equally reddened ass and legs.

"Lady Jessica!" came an excited call as they moved through the crowd. Jessica turned and smiled warmly as a tall lady in her mid 50's approached with open arms. "My you look divine tonight my darling." she continued as she hugged Jessica. "And this pretty young thing you must be your new submissive we've heard so much about, Candi?"

"A pleasure as always Lady Abigail, yes this is Candi, sort of. At the moment it is Tom but I'm sure Candi will put an appearance in later. Tom this is Lady Abigail our host for this evening and one of the most senior ladies of our little group. Say hello."

Tom took the elegant gloved hand Lady Abigail offered and curtsied awkwardly as he kissed it reverently "A pleasure to meet you Lady Abigail."

"Oh such a well behaved little sissy isn't he." she said as she walked around him inspecting him carefully with her eyes as her hand traced his waist and onto his ass she circled him. "And such a fine pert little ass just like you said." she exclaimed as she firmly groped his rump. "I look forward to seeing how far you've come in such a short time." Her hand lingered on his ass a little while and she smiled coyly at him "I do love playing with a pretty sissy." she whispered in his ear before the statuesque matriarch slipped back into the throng of people taking a freshly poured glass of champagne from a waiter in blue as she went.

"It seems you've made a good first impression with Lady Abigail." Jessica said as she lead on through the throng. "She does enjoy sissy boys and she can be very demanding once she decides what she wants, perhaps we can play with her later?"

"I'd like that Miss Jessica, she really is very beautiful, everyone here seems very beautiful in fact."

"Yes, that's what happens when people are true to themselves, their beauty shows through. Even those that don't conform to the cultural norm of beautiful positively glow when freed from the shackles of denial and cultural stereotypes."

A gong sounded calling the party to order, the string quartet began their final number as people moved to the large hall beyond the reception area. Jessica handed the gold leash to Tom and took the white bonnet and placed it carefully on his head.

"Follow the other sub-maids, they know what to do. I'll catch up with you after the official opening ceremony is over and the festivities get into full swing." she winked and patted his ass firmly as he moved off to joint the line of other subs filing into the hall. He slipped into the line behind a well built man in tight red shorts and a red leather harness covering his chest. With the bonnet in place seeing either side was difficult so he followed the line hoping to end up at the back of whatever congregation awaited him inside so he could see what to do next.

A large red carpeted area lay ahead of several rows of ornate wooden chairs. On the carpet sat neat rows of red velvet pillows. The sub-maids quietly filed in under the watchful eye of an Aunt, filled each row and knelt on the cushions, bowing their heads. Mercifully Tom ended up in the third row and so could observe what everyone else was doing despite his restricted field of vision.

Ahead of the sub-maids a large stage was setup, the backdrop draped with red and black satin, large vases holding red roses flanked the large throne in the centre, 6 smaller thrones sat either side. As the room took their seats the procession of leading members filed onto the stage to a ripple of applause and took their seats, Abigail taking the central throne. Tom wasn't surprised to see Jessica step up and take her place to the right of Abigail.

The applause subsided and Abigail stood to address the room "Welcome my wonderful friends and our honoured guests to this wonderful evening of sin and surrender. We have only a few items to deal with before we can begin the festivities so I will try not to keep you long."

"As always the communal playrooms will be open all evening and the equipment is available for all to enjoy. A limited number of private rooms can be booked on an hourly basis should you wish to be more selective in who you play with. These rooms can be booked with Aunt Melissa at the concierge desk. Whatever play you indulge in, as always, we insist is ALWAYS consensual and where a sub-maid is wearing anything other than a green bracelet it must be with the participation or express permission of the owning Domme. Should the sub-maid be wearing a green bracelet then it is assumed that consent for play has been given by their owning or betrothed Domme and by the sub-maid themselves."

"A demonstration will be held in this room at 10pm hosted by Lady Jessica, all are welcome to come and enjoy and hopefully participate in the show." Abigail gestured at Jessica and smiled warmly at her before returning her attention to the room again. Tom felt his heart miss a beat as he knew he was likely to be part of the demonstration if it involved Jessica."

"Now to matters of discipline. As you all know where a Mistress has issues with her sub-maid, we as a group always endeavor to assist and nurture their relationship through passive advice and teaching. Sometimes however the problem requires intervention from other Dominants to help bring the sub-maid back in line, a task we often relish." she smirked and a ripple of laughter spread through the room. "Miss Michelle, would you please join me?"

Tom heard the sound of a brief screech of a chair followed by a swish of fabric as someone stood behind him, the sound of her heels on the tiled floor clipped as she approached the stage. A mixed race lady with shoulder length curly dark purple hair slid into his view. She was short but exuded confidence, her long black satin dress flowed into a tight black corset with white boning and stainless steel clasps her ample breast nearly held in by the cups. Tom couldn't help but focus on her full red lips as she smiled at the room from the stage.

"I have been a full Mistress for just over a year and collared my first submissive only a few months ago along with my wife Miss Lucy." She began, "OfMichelle consented to be collared and serve as our joint sub-maid however sadly we have had issues with discipline over the last few weeks. OfMichelle will not restrain his masturbation and despite following the advice of several of my sisters and fitting him in a chastity device he has continued to rub himself and ultimately ejaculate without permission several times to our knowledge."

Abigail stepped in "OfMichelle, please stand and show yourself to the room." in the row ahead a man stood up, clad in a red rubber catsuit it showed his toned slim body. From behind Tom couldn't see much more but suspected he would shortly.

"Continue Miss Michelle."

"OfMichelle has continued to disobey our 'no cumming' order despite our attempts to discipline him. We have tried most traditional methods of discipline but only complete immobilisation prevents him from playing with his little dick. Sadly he enjoys pain too much and this only aggravates the issue as he often reaches climax without permission if he is physically punished. It is not practical or pleasing to keep him trussed up permanently so we are now at an impasse as controlling his orgasms is a key part of our house rules and gives us great satisfaction. As we have made no progress in correcting his behaviour we appeal to the sisters of this group to assist us more directly to realign his behaviour to our needs and desires."