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

"OfMichelle, do you wish to continue to be the collared sub-maid of Miss Michelle and Miss Lucy?" Abigail asked bluntly

"Yes Lady Abigail I do."

"And do you agree to endure any assistance meted out but the sisterhood here today in order to help you stop this aberrant behaviour?"

"Yes Lady Abigail, I do."

"Well that's progress isn't it, come and stand here." she pointed at a spot in front of the stage and the sub-maid obediently padded to where he was instructed and stood facing the room. Tom could see his cock was in a heavy metal chastity device and wondered how on earth he had managed to please himself in that monstrosity. he couldn't see the sub-maids face as he wore a full face rubber gimp mask with only eye and mouth holes giving a glimpse of his skin.

"The Ladies and I have considered the issue and decided on a suitable method that we hope will lead to more suitable behaviour in the future if you agree to allow us to proceed Miss Michelle."

"Yes Lady Abigail, please do." she said sounding dejected but determined.

"Aunt Sarah please bring in the chair."

The platinum blond of Sarah was instantly recognisable to Tom as she pushed a wheeled contraption out below the stage. Her remarkable figure was sprayed in a figure hugging bronze dress which clung to her every curve. He felt the stirring of arousal seeing her but his cock remained soft and in line with Jessicas programming.

'The chair' was a plush leather seat firmly fastened to a wheeled platform. Leather straps hung open on the arms, backrest, seat and lower front. To one side a large mechanical contraption lay to one side, just out of view enough to make its purpose a mystery. OfMichelle was guided to the chair and Sarah began to fasten each of the straps slowly but surely immobilising the sub-maid.

"This glorious contraption......" said Miss Abigail as she stepped from the stage and sashayed towards the now completely helpless sub-maid. "Is yet another of Miss Rosalind's creations" She gestured towards a red headed Mistress sat in the last throne on the right. "It should teach OfMichelle to be careful what he wishes for. Miss Michelle, please would you unlock OfMichelle?"

"Of course Miss Abigail" Miss Michelle quickly found the key that hung from a delicate chain in her ample bosom and slipped the lock from the chastity device before removing the heavy metal sheath from his engorging cock.

"Excellent now swing this contraption over and bolt it down on the other side." Lady Abigail said as she pointed to the lump of machinery. Miss Michelle swung the machine over and clipped it into place smiling as she did so, realising the purpose of the machine. "I think you can see where everything else needs to go."

"Indeed I can Miss Abigail" Miss Michelle squirted lube into a long supple sheath then slipped it over OfMichelle's now hard member. Miss Abigail handed her a small wireless box which Miss Michelle took with eagerness. Turning the dial the sheath began to smoothly slip up and down and OfMichelle tried to grind in time with the motion as it moved.

"One final touch." grinned Lady Abigail as she slipped a rubber tube onto the top of the sheath before placing the other end into the back of a cock gag. She slipped the cock gag into OfMichelle's mouth and tied the buckle tightly "perfect! If he will insist on ejaculating without proper permission the least he can do is clean his own mess up" That raised a giggle from the crowd.

It wasn't long before OfMichelle began to moan, the smooth stroking quickly working him towards his climax. Miss Michelle watched him writhe and struggle as his orgasm built and soon inevitably he came. The white liquid being sucked up the tube and into his gagged mouth. Miss Michell reached for the control box but her hand was stopped by Miss Abigail.

"I think we should leave him just like that for a while, don't you Miss Michelle, let him think about his aberrant behaviour?"

"How long should we leave him with it rubbing like that?"

"Well I tend to find that by the fourth or fifth orgasm things tend to get quite tender and by nine or ten they will literally do ANYTHING to let it stop so perhaps pop back in an hour?

OfMichelle's eyes widened as his second orgasm began to build and he realised he was to be milked relentlessly.

"Why don't you enjoy some of the other delights in our presence and pop back when you have been sated, perhaps speak with Miss Jessica about her particular methods of control. The chair will be yours to loan for as long as you need to enforce your will on this little cum addict."

"Thank you Lady Abigail and Miss Rosalind, I think this is perfect." Miss Michelle chuckled as OfMichelle shuddered towards his second orgasm and she reached forward to kiss him on the cheek before returning to her chair leaving an exquisite lip mark on him.

"Is there any more business that needs attending to before we all enjoy our evening?" The hall remained quiet but for the quiet pulsing of the milking machine and the awkward groans of OfMichelle as he fought against the unrelenting stimulation.

"Very well ladies, play safe and play well."

The Mistresses broke from their chairs and filed out, an Aunt then lead the sub-maids in single file to the main room where they would rejoin their Mistress'.

Tom watched the spectacle wide eyed as he waited his turn in the line to file out. Though his field of vision was limited by his 'wings' he marveled at all the different kinks represented by the sub-maids as they walked obediently back to the main lounge.

Jessica gently grabbed his arm as he filed out of the room and guided him with her across the lounge "Poor OfMichelle will be quite sore tomorrow I think." she quipped "I've experienced one of Lady Rosalinds creations once before and they are exquisitely tormenting for the little subbie but they do get the job done."

"Miss Michelle has requested a private meeting as suggested by Lady Abigail, are you ok with that my sweet?" she continued.

"Of course Miss Jessica, I'm happy to serve."

"I knew you would be, come, we're going to have so much fun."

The Party - part 3

A gentle knock announced Miss Michelle's arrival at Jessicas private suite

"Come in, we're descent..... at the moment." Jessica grinned in anticipation as the coffee skinned Domme entered the room.

Tom knelt quietly in the corner admiring the two women as they greeted each other with a tender kiss and hug. The first pangs of arousal beginning to slip through his body as he casually fantasied about them all together.

"Thank you for seeing me privately Lady Jessica, I'm really excited to see how you can potentially help my wife and I with our sub-maid."

"Come Michelle, we ladies have to stick together, I'm very happy to help. This is OfJessica my newest sub-maid." She said gesturing to Tom. "His real name is Tom, or Candi depending on the mood. He's such a wonderful example of what my techniques can accomplish." She smiled tenderly at the doting sissy.

"He's awfully convincing, I thought he was a real girl when I first saw him."

"Yes he's become quite good at all the things we women go through to look amazing but his basic physique helps with the illusion." Jessica circled Tom running her finger gently over his latex covered shoulders. "Now bearing in mind your current troubles, I think it might be best to demonstrate the level of control I have over not just his mind but also his physiology. This doesn't happen over night mind you and will require several repeat sessions but you'll see results each time even from day one if your sub is receptive."

"Tom sweetie why don't you stand so Miss Michelle can properly inspect you." Tom stood obediently and was guided forward by Jessica's hand on his back so he now stood in the middle of the expansive suite. "Are you feeling horny my sweet?"

"Yes Miss Jessica." he replied truthfully, he had no reason to lie

"Tom is a ostensibly a straight man but I have managed to corrupt him over the last few months and bent his will to my particular needs and desires. With my conditioning and triggers I can persuade him to do many things his vanilla persona secretly wanted to try but found difficult to accept. We built on this to take suggestion further to physiological control." She slipped a slender finger under the hem of his latex dress and pulled it up till his sheer panties were clearly visible, framed by his garters and stockings. "You'll notice that even though he says he is aroused, his little boy clit has stayed small and soft." she went on pointing to his crotch.

"And you control his ability to get hard? Really?"

Jessica grinned "Really! Why don't you try to arouse him, it will be nice to see how the conditioning reacts with another dominant before I publicly display him later."

Michelle approached and circled Tom, her steps slow and measured in her black stilettos. She dragged her long red finger nail up his exposed thigh towards his panty-line but his cock remained stubbornly flaccid. "Wow, even the slightest touch here has OfMichelle rock hard."

She continued her circle dragging her nail over his firm ass and stopping behind him to kiss him gently on his neck leaving a sticky Scarlett lipstick print. She held herself against him allowing him to feel the heat of her crotch against his ass and she slipped her hands to his front and over his cock, still nothing.

Jessica had taken a seat in the large wing back and watched the show as Michelle slipped her hand into his panties and began to stimulate him more directly while her other hand squeezed and massaged his ass as she licked his ear lobe slowly. "Really! Nothing?"

"Its really very nice Miss Michelle." whispered Tom which gained him a sharp whack to his behind.

"I didn't ask you to speak little one!" Michelle chastised "but thank you for giving me an opportunity to spank you, I do like a good spanking." She slapped his ass twice more before kneeling behind him and slipping his panties to the floor and tenderly kissing his reddening cheeks, leaving her scarlet prints dead centre on each one and allowing her sharp fingernail to trace down his ass crack and below to his perineum before cupping his balls while rubbing his cock with her other hand.

Jessica smiled and opened her legs, slipping her finger into her rapidly moistening pussy as she enjoyed both his torment and obedience. She even began to pick up the first signs of his quivering muscles as they fought the sensations assaulting his sensitive places. "Why don't you try something I know gets him very hot, freshen up your lipstick in front of him, he's got a weakness for that, its how I got him hooked to be honest."

Michelle stood and slinked her way back in front of Tom, opening her small clutch bag and taking out an expensive looking shiny lipstick tube and twisting the soft scarlet stick into view. "You're a lipstick slut are you pet? How lovely."

Tom nodded, careful not to answer for fear of another swat. She leant in close and slid the velvety lipstick over her voluptuous lips freshening the strong colour, allowing Tom to see every moment of the action as well as smell the soft feminine scent and hear the moist pop as she slid her lips together and then opened them again. She slipped the lipstick back into her clutch and noted that he still wasn't even getting a semi "Wow I really am impressed by his self control."

"That's the thing, its not self control, I've gained such a deep control of him I can tinker with some physiological functions. Why don't you try the ultimate arousal tool and slip him into your lovely mouth and I'll demonstrate" a soft moan came as she finished speaking and Tom could see the first signs of Jessicas orgasm approaching.

Michelle slid to her knees and faced his soft cock "I bet you can't wait to have this boy clit slip into my slutty red lips can you?" Tom bit his lip and chanced a look down as she took is cock in her hand once again and placed the tip on her lips. Her lipstick smeared on his cock as she balanced it just on the edge of entry before opening her lips wider and allowing his tip to slip slowly into her warm mouth. He couldn't help but whimper at the sensation as he slipped into her warm mouth. Still his dick remained frustratingly at rest despite her eager tongue and soft lips lavishing him with attention.

"Now for the moment of truth." Jessica slipped her finger deeper into herself as she spoke his trigger "Tom my sweet, why don't you rise to the occasion?"

Immediately Michelle's eyes widened as his cock now quickly hardened in her warm soft mouth, right on queue and another moan escaped Toms lips at the limited release.

Michelle slowly slipped her mouth from his member with a soft pop grinning at the red lipstick smear she had left behind on his shaft and the large lip print at the base. She laughed openly "That is awesome, I've never seen anything like it." She slipped back onto his dick and ran up and down his shaft a few times more, noting the increasing shivers through Toms legs as she teased him. Allowing herself one final long lick up his now long shaft. "I haven't sucked a real cock in quite a while, what a treat to have it blossom in me like that." She held his member eagerly in her hand "but what about orgasm control?"

"Oh we've got that covered too don't we Tom"

"Yes Miss Jessica" he managed over his quivers.

"Tom, put it away"

Almost instantly Michelle felt his member soften in her hand and droop, Jessica moaned in delight at the success and delighted in the small grunt of frustration she heard from her submissive toy.

"That is uncanny, I've never seen that happen in any man once he's that far on without a good deal of physical 'persuasion' with a crop or paddle." Michelle delighted.

"It is a treat isn't it?" said Jessica, slipping her finger from her slit and moving to the large luxurious bed. "Would you like to fuck him, he does enjoy a good prostate milking, there's a strapon on the shelf that should make it fun for both of you."

"I'd love to" Michelle delighted and rose to retrieve the leather harness with its double ended cock held firmly in place. Unzipping her gown she let it fall to the floor leaving her in her black satin corset and stockings, her panties already missing. She slid the harness up her legs and delighted in slipping the inner phallus into her now very wet snatch and then fastened the straps tightly.

"Tom come over here and bend over the end of the bed so Miss Michelle can get a good angle at your sweet little ass." She lay back as Tom positioned himself over the end of the bed with his ass high in the air. Once he was in the right spot Jessica shuffled forwards and moved her gown and panties to one side and placed her ripe pussy on his nose allowing him to smell her musky aroma as he awaited Michelle to enter him.

Michelle was soon behind him and he felt the cool sensation of lube being dribbled onto his rosebud and soon the familiar pressure of a rubber cock pressing against his hole.

"Eat me while Miss Michelle fucks you my sweet." Tom eagerly slipped his tongue into Jessica's hot sex and gloried in her sweet taste as the head of Michelle's cock slipped into his eager ass. He moaned as she began to thrust gently and the dildo caressed his prostate relentlessly. As Michelle thrusted he pressed backward, eager for release as he worshipped his own Mistress but deep down knowing release was unlikely for Jessica thrived on tease and denial and cumming was no longer his decision.

It wasn't long before all 3 lingerie clad figures were moaning and grunting their way to climax. Jessica reveled in watching Tom ruin his makeup in her dripping pussy while above him the delightful curving beauty of Michelle rode his ass. Michelle broke first and moaned deeply as she was overcome by her climax and Tom felt her warm juices flow down the shaft of her cock and down his ass. As her thrusting slowed Jessica reached her own peak and squirted her own hot cum into his waiting mouth and ground his face into her snatch to eek out every shiver of pleasure before lifting his head from her.

Michelle tenderly pulled out from his ass and caressed his ass cheeks smudging her lipstick prints as she did so "oh wow, that's a bit of a mess you've left OfJessica." she exclaimed as she stood back and enjoyed the spectacle before her.

"Has his precum dribbled?" Jess asked

"He certainly has, its all mixed up with my own juices too."

"Tom be a good obedient submissive and clean up your mess."

Without question Tom slipped from the end of the bed and immediately began to lick up the salty warm collection of fluids on the tiled floor at the end of the bed.

Michelle watched intently as Tom cleaned up the mess "and you say he was straight only a few months ago and now you have him being fucked in the ass, control his orgasm and having him lapping up his own cum on command?"

"Yes, its really quite splendid isn't it?" Jessica quipped as she came down from her high.

"The question is when can you start with my errant subbie?"

"I thought you might like me to take a look at him once you'd seen the results with Tom here." Jessica slid off the bed and tidied her gown back to its correct shape before approaching Michelle. "I'm happy to start next week I'm sure we can find a good day for both of us. I Can't promise results as it definitely depends on the willingness and susceptibility of the subject but I'm sure we can get some results. Have your people call my people I guess?" Michelle nodded and collected her gown from where it lay before slipping out of the room grinning wildly with the possibilities that her meeting with Jessica presented her.

"Tom sweetie, when you are done cleaning up your mess I'd like you to get cleaned up. I need you to dress as a normal man for our demonstration, you'll find some of your boy clothes in the closet along with some nice lingerie for underneath."

"Yes Miss Jessica." he replied licking the last of the puddle of cum from the wood floor.

Tom reappeared in the main room of the suite in the skinny jeans and red button down shirt Jessica had packed for him, his face clean of any feminine touches and looking like the handsome young man she had met on that first on line date.

"Miss Jessica, I don't really understand why you all of a sudden want me to dress like this when you've spent so long pushing me towards being more feminine."

"I know my sweet but its for the demonstration I've been asked to make for the ladies. I'm sure you'll be fabulous. Now why don't you sit here and we'll have a chat about it so I can explain." She gestured to the two large leather chairs next to a coffee table in the lounge area. As soon as he sat she saw the glassy look come over him as his conditioning took effect. "What a good sleepy submissive you are." his eyes snapped shut on command.

"Tom, for this demonstration I need to show how far you've come and demonstrate what a wonderful hypnotic subject you have been over the months we've been together. For that to happen I'm going to ask you to forget a few things and have you revert back to when you didn't know I was hypnotically manipulating you. When I wake you you will forget all about being my good little sissy and your Candi persona. You will retain all of your triggers but you won't remember anything about being hypnotised or any of the wickedly delicious things we've done since we met in person. In essence you will be just like the Tom I first met in person for our first dinner. Do you understand Tom?"

"Yes Miss Jessica." he mumbled quietly in return.

"Good boy, you'll only recall having had a lovely few weeks together with some amazing sex and that you are very much enjoying our relationship. No trace of dressing like a pretty sissy or your introduction to all the devilish and gender bending acts will remain, you wont even notice the lovely lingerie you are wearing under your boy clothes. You are a straight guy who is very very happy with his new relationship with his new lady friend."