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

She continued to reinforce his new mindset for a few more minutes before she felt he had fully comprehended what she needed of him. "Now Tom when the demonstration is over and you hear me say 'I'd like my sissy slut back now please' you'll revert back to your new life with me, do you understand?"

"Yes Miss Jessica."

"What a good little submissive you are. Now in the demonstration we'll be up on the stage and I don't want you to feel embarrassed or exposed, I just want you to feel comfortable and happy to be part of the show, is that OK?" He nodded slowly "no one will hurt you or make fun of you, I'm sure you will be the biggest hit with my friends. Now sweetie, when I click my fingers I want you to open your eyes and be fully awake not remembering any of this conversation, just being you, my wonderful Tom."

She slid from her own chair and sat delicately onto his lap before snapping her fingers. Taking his chin delicately with her hand she kissed him deeply and he responded eagerly wrapping his tongue with hers. She allowed his hand to explore her naked thigh and stocking tops and she could feel his arousal build in the tempo of the kiss but his cock never stirred just as she had hoped.  

The party - part 4 The demonstration

Breaking the kiss and standing she walked to the mirror above the fireplace and took out her lipstick making sure he got a good view of her reapplying the burgundy colour, knowing it would increase his desire. "Come on sweetie, its time to meet your adoring fans." Taking him by the hand and leading him to the main hall where the ladies and their sub-maids were already assembling and taking their seats and cushions respectively. As they took to the stage, a round soft applause rippled through the room welcoming them.

A hush came over the room as Jessica's heels clipped to centre stage "good evening ladies and dear sub-maids" she began "I've been asked by Lady Abigail to showcase my latest work with my new sleepy submissive, the lovely Tom here." she gestured to Tom who was sat on the stage in one of the lesser thrones. he slumped in the chair immediately

"Some of you may already know I have dabbled in all manner of domination but have found my particular talents lie in hypnosis and the delicate manipulation of a submissive through trance. Tom has come so far over the last few weeks but for the purposes of demonstration I've temporarily regressed him to the point before he knew I was hypnotically manipulating his mind. As you can see a simple word and he slips deeply into trance. I will hopefully show you how powerful my methods are and the results that can be achieved through only the power of words. I'll even try to demonstrate on a willing volunteer or two in the course of the session."

"Now to dispel a few common misconceptions about hypnosis. I cannot and would never try to compel someone to do something they don't want to do. Its not like the super hero movies where we can force someone to do a dirty deed or harm themselves at my whim. Tom was carefully selected and has always been given the chance to back out of anything i have asked of him including this demonstration. The key is that we simply remove the social inhibitions that stop us following our true desires. For want of a better term, I have unshackled his inner desires and allowed him to explore kinks and fetishes he already had but had kept suppressed."

"So on with the demonstration, you will notice we have some screens in front of the stage, these will periodically show some footage and pictures of what we've been up to over the last few months. I don't want Tom seeing the images just yet as I have regressed him to the point before he knew he was being hypnotised. I have left his triggers in place and I will demonstrate those in due course. Tom sweetie, shake a leg and introduce yourself."

Tom's eyes fluttered open and he looked a little confused before settling back into the chair "erm, hello everyone, I'm Tom, Jessica's... boyfriend?" He glanced at her looking for confirmation and found it with a nod.

"And how long have we known each other Tom?"

"Oh err I guess around 3 months or so, we met on a dating app but live a ways away so didn't get to physically meet till a few weeks ago."

"And you're happy with our relationship so far?"

"Of course, you're stunning, intelligent, demure....sexy as hell!" The room laughed with him and Jessica feigned embarrassment.

"You are so kind Tom. Now would it be OK if I asked you a few personal questions in front of the group?"

"I guess, as long as they aren't too personal."

"Great, so Tom have you ever worn makeup"

"Er, I think I did in a play when I was like 12 yers old maybe." Jessica pressed the button on her remote and the screens came alive with a picture of him glassy eyed wearing a deep red lipstick causing the crowd to giggle.

"You're sure about that?"

"Pretty sure." he said.

A bigger laugh percolated across the room as a video played of him happily and very competently applying makeup at a vanity in Jessicas house.

"Good now, Tom, are you gay or straight?"

"Straight."

Gasps ensued as the screens showed video of Tom, in full makeup sucking on a thick cock in the glory hole in Sarah's salon, followed by another of his ass being pounded by Dylan while he licked Jessica's pussy to orgasm.

"Excellent, so I need a male sub-maid volunteer if I may?"

A few hands raised and she picked a handsome leather clad man from the second row. "Come up darling and just stand here if you would" she said gesturing to a spot in the centre of the stage

"So Tom, you don't find this rather splendid specimen in the slightest attractive do you?"

"Well I mean, he's a good looking guy but no i don't find him sexually attractive."

"But would you kiss him if I asked you, I do find that so hot to watch."

"I'm not sure I'd want to to be honest." he glanced at the sub-maid "no offence."

"Tom be an obedient submissive and come and kiss this outstanding young stud, like you mean it, then go back and sit down."

Tom stood and walked straight to the waiting sub-maid and immediately kissed him, slipping his tongue deep into his surprised mouth and allowing their tongues to intertwine. After a good minute Tom broke the kiss and went back to his seat and sat back down a very confused look came across his face as he considered what he had actually just done.

"Sleepy submissive." he slumped once again into trance "now forget that lovely kiss just happened and come back to us when I click my fingers." 'CLICK' and his eyes flicked open to a round of applause. "Thank you OfMeghan, you can go back to your place now" and she guided the sub-maid from the stage. Looking down to the other sub maids she could see more than one looking rather nervous as they processed how much control she had over Tom and what could be coming next.

"As you've seen Tom can be very 'accommodating' when given the correct encouragement but this isn't the end of the story. Once again we'll need a few volunteers. Hands immediately flew up to be part of the next demonstration. "Miss Jane would you please be my lone Mistress, you're just what I need." The red headed Mistress elegantly strutted to the stage and was guided to a point just in front of Tom.

"Now I need to make this fair so which male sub-maids have been allowed to cum so far tonight?" About 6 hands went up, excellent. Miss Nicole if you approve can OfNicole please join me?" A blonde Mistress nodded enthusiastically and a muscular sub got up form the ranks and made his way to the stage and was guided into position

"Finally I need a female or a sissy sub-maid, who likes to please the menfolk, Miss Eve, if you approve?" The petite brunette in the second row nodded and her very convincing sissy Sub-maid was also guided to the stage next to OfNicole.

"OK so we'll play a couple of games shall we. Tom will you join Miss Jane please?" Tom got out of his seat and stood next to Miss Jane and Jessica arranged the two couples so they were stood side on the audience. "So the first game is who can last the longest without getting hard, Tom or OfNicole. Miss Jane, OfEve your task is simple, excite your partner by any means necessary in order to get him nice and hard. Last one to get hard wins but I know how excitable OfNicole can be so I think its only fair we give Miss Jane a head start or poor OfNicole will lose the game and we don't want him unfairly punished."

"Miss Jane, on your marks, get set, go." Jane knelt in front of Tom, slipping her open hands down his thighs as she descended then slowly unfastened his his jeans while looking up at him and let them fall to the floor. A ripple of laughter rose from the crowd as the jeans fell and revealed Tom wearing a vintage garter belt, stockings and a pair of frilly pink panties. "Tom, have you been in my lingerie closet again?" Tom self consciously looked down to see the frilly lingerie and became confused.

"What, how did these get here" but he was soon silenced as Jane continued to caress his thighs and worked her way to his panties letting those fall to the floor as well revealing his drooping cock.

"Now you may wonder why I chose Miss Jane, well Tom here does have a little fetish for red heads who wear heavy makeup so I'm really trying to give OfEve and OfNicole a fighting chance"

Jane gently kissed the tip of Tom's cock leaving a sticky wet lipstick print, looking up she whispered "do you like that Tom, do you like a perfectly made up woman kissing your cock and leaving her lipstick marks on you?"

Tom bit his lip and tried not to look at her as she continued to caress and tease him "mmm hmm." was all he could muster

"Should we set the other contestants away?"

"Yay!" shouted the remaining audience as they quickly warmed to the game

"OfEve, off you go, Tom, OfNicole, last one to get fully erect wins, first one to get erect gets punished!"

OfEve dropped to her knees and soon had OfNicole's dick in her hand and was expertly slipping it into her eager mouth. The concentration on OfNicole face was intense as he tried to fight his inevitable arousal but the result was inevitable and his cock was soon standing to attention. OfEve slipped him from her mouth and stood away.

"Looks like we have a winner, well done OfEve, you really are a talented cock sucker." the pretty sissy boy took a polite curtsey and grinned broadly.

"Miss Jane, any life overly there?" Tom remained resolutely soft in Jane's expert hands despite his face showing his torment and obvious arousal.

"Nothing Lady Jessica, I've never had a problem before, are you sure he isn't gay?"

"Tom, any reason you aren't hard yet, would you prefer me to find a male to suck you off?"

"No Miss Jessica, I'm very confused, Miss Jane is very good at what she is doing but its just not happening." Jane took a final long lick down the underside of his flacid dick before giving up.

"Oh Tom, I think it's time you rise to the occasion." his cock quickly grew and became fully erect on command to the surprise of all that were watching "There, much better." Tom's relief was obvious.

"Everyone ready for the next round?" Again the audience replied enthusiastically and Jessica began to describe the rules once again. "Poor Tom hasn't had an orgasm in oh, 3 or 4 days so he's ready to pop, OfNicole on the other hand has already been treated to an orgasm tonight so should be quite resilient to OfEve's ministrations especially being that he is straight. Same rules apply but this time first one to shoot their load loses. Jane maybe freshen up your lipstick and really switch on your A game?"

Jane slipped her crimson lipstick from her stocking top and got close to Tom's face as she applied it heavily to her full lips before kneeling back in front of him.

"We'll give OfNicole a bit of respite as I know what an expert cocksucker OfEve can be so Jane, in your own time, off you go"

Without any more encouragement Jane slipped Tom's hard cock into her warm mouth and expertly worked her tongue up and down his shaft in perfect harmony with her long slow rhythm while alternating her sharp nails and smooth hands across his bare thighs and gently caressing his balls and perineum. She kept eye contact with him the whole time and could see the desire building in him as she sucked him towards his climax.

"OfEve, off you go" the sissy had already fixed his lipstick and was immediately on his knees in front of OfNicole hungrily gobbling up the bulls massive cock into his wanton eager mouth. In no time both receiving men were gasping and panting with effort to prevent them cumming in their tormentors mouth.

OfEve was taking every inch of the 10inches of meat OfNicole had to offer and the telltale signs of impending climax were becoming apparent in both men, their legs were shaking and they had both begun to sweat with effort as they strained to keep a lid on their climax but the result was inevitable as Jessica well knew.

OfNicole's hips bucked uncontrollably as he succumbed to OfEve and he thrust his cock into the sissy's hot mouth and spewed his jism into his throat in this long hot ribbons. OfEve gobbled the cum into his mouth and squeezed out ever last drop as OfNicole bucked and twitched. Tom was moaning and quivering but he remained stubbornly on the edge of climax with no way to tip over the edge despite Jane's expert attention.

"Looks like we have a winner, looks like OfNicole is heading for some punishment for letting down his Mistress." goaded Miss Jessica "OfEve would you like to give Tom his prize?" She winked at the slutty sissy and he smiled back knowingly. Miss Jane slipped his raging cock from her mouth and moved to one side allowing OfEve to approach unhindered. The slutty sissy boy kissed Tom firmly on the lips smearing lipstick and cum on his lips before surprising the startled Tom and forcing the whole load of spunk into his mouth before retreating.

"Oh Tom, I thought you said you were straight and yet you seem to have another mans load of spunk in your mouth." Tom looked horrified having come from overwhelming pleasure to being degraded by a cross dressing whore snowballing another mans cum into his mouth. "Now be an obedient submissive and swallow your prize." she commanded and in one motion he swallowed the load without question.

A raucous round of applause spread across the room as they watched Tom's deprivation unfold much to Jessica's delight. "Tom," She said as she approached her confused and obviously dazed submissive "Why don't you be an obedient submissive and put this lipstick on and then suck off the wonderful OfEve to reward her for her fine performance."

Tom took the hot pink lipstick from her and expertly applied it then dropped to his knees in front of OfEve, slipped the sissy's tight panties to one side and slid his hardening cock into his mouth. He expertly bobbed his pink lips up and down on the sissy's cock smearing his lipstick on the firm shaft. Tears beading in his eyes as the depravity hit him and OfEve climaxed in his mouth with another load of warm salty cum.

"Now swallow it like a good boy Tom." there was no point resisting, he knew at this point that he didn't have a choice in the matter so he simply swallowed the sissy cum without protest. "What a fabulous job you did my sweet." she said as she hugged him tenderly and kissed his cum smeared lips deeply then whispering in his ear, reassuring him that she loved him deeply for being such a good submissive. Tom felt the shame evaporate as he realised she was proud of his actions, not disgusted.

"As you can see ladies, the power of hypnosis has a unique place in our world of domination. Tom would never have thought of dressing in such frilly underwear or swallowing another mans cum let alone 2 in the space of 5 minutes had I not facilitated him in exploring his fetishes. Tom had an underlying fetish for being dominated and secretly wished to be made into a sissy and be used for his mistress' pleasure. This desire was already there so when asked,he would comply because it is not against his internal moral compass. If I had asked him to say suck off a horse or harm himself he would never have complied as this isn't something he is into and his moral compass would stop him engaging in such actions. As with everything in our kinky world, consent is essential."

Stood on the stage she welcomed the applause from the room as Tom knelt beside her, she tenderly hugged his head to her side as she enjoyed the moment. She leant down and whispered to him "I'd like my sissy slut back now." and all his memories came flooding back and he smiled warmly as he gazed up adoringly at his Mistress and licked the last remnants of slaty cum from his lips.

The party -- part 5

Tom had been led back to their room by Jessica where she hugged him tightly as a reward for his outstanding performance. There was no doubt the demonstration of her hypnotic control over him had caused quite the stir in her covern of Dominas. She considered her position carefully before suggesting "Why don't you pop to the lounge for a little respite my sweet, perhaps you can find our next adventure there?"

Tom looked up into her eyes from his low position in the hug, "Are you sure Miss Jessica?"

"Of course my sweet, it can't all be just what I want can it?"

"But I am here to serve you Miss Jessica not the other way around" he sounded confused.

"Don't worry my sweet, I'm sure I'll fit into whatever mischief you get yourself into. Just tap your bracelet clasp three times and it will tell me where you are in the building and that you would like me to join you, isn't technology wonderful!"

"Ok Miss Jessica, I guess a bit of down time after the show would benefit me a little and its not as if I can do much beyond making out without your help anyway" Jessica chuckled at his reflective comment about her control over his cock as he walked out of the room and made his way to the subbies lounge.

The lounge was dimly lit and had the feel of a seedy bar, a pretty blond lady was idly polishing a glass behind the bar where he took a seat on the high stool and ordered a beer. It was only then he realised he was still in his 'boy clothes' but he could feel the reassuring slinky lingerie beneath his smart jeans as he slipped his butt onto the stool.

The pretty bar tender served him a cold beer and an even colder glass from the freezer with a cherry smile. Tom took a deep gulp as he felt himself relax from the sexual melange that he had been involved in in the last few hours. He would never have been a part of anything like it without Jessica he thought as he reflected on how free he felt around her and the people at the retreat.

A gentle squeak announced the neighboring stool being pulled back and a young lady slipping onto it. She was stunning, as most were here, rocking a simple long sleeved, v-necked top which accentuated her ample cleavage and an ankle length black and white checked skirt bolstered out by a thick black taffeta petty coat which splayed out the skirt. Her blond hair was tied up with a cute red bandanna and her face delightfully made up with soft smokey eyes and red luscious lipstick.

"Hey aren't you the hypnosis guy" she said as she glanced at him.

"Yes that would be me" he smiled as he turned to look directly at the stunning face that accompanied the smooth voice and beautiful body. "Can I get you a drink Miss?"

"Why sure, can I get a Scotch and soda on the rocks?" The bar tender was already on her way and pouring the expensive liquor into a low ball tumbler before Tom managed to order.

"Are you having fun tonight?" Tom asked trying to strike up a conversation in an otherwise quiet bar.

"Of course," she purred, "How can you not have fun at one of Lady Abigail's retreats" her grin was infectious and Tom found himself quickly warming to the young lady. She took her freshly made drink from the bar and slipped from the tall bar stool with a swish from the taffeta petticoats. "Shall we go to a booth? I'd love to hear more about your situation with Lady Jessica."