Jessica and Tom 04: New Relations

Hello again readers, sorry there has been such a gap in the series, life gets in the way as usual. More to come but may be a while as I dream up new directions for our protagonists. In the mean time I hope you enjoy this latest installment.

Mindandbody

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Asking for an extension

A few days had passed since their return from the 'Sub-maids tale' party and Tom and Jessica had become more and more intertwined. Jessicas kinks for dominance and control dovetailed so neatly into Tom's own kinks and his desire to submit and be controlled. The more time they spent together the more Tom knew this was likely to become a longer term relationship. He had emailed work and asked for another week of leave which had been granted due to the low workload currently passing through the office. He was thrilled he would be able to spend more time with Jessica.

"Miss Jessica may I discuss something with you?" He said as he came into the lounge where she was as always tapping away on her laptop.

"Of course my sweet, how can I help?" She placed he laptop on the 'multi-purpose' coffee table and invited him to sit on the sofa beside her.

"I have asked for another week of leave from work and they have granted it, is it OK if we extend our time together?" She frowned and stared at him, Tom felt his stomach lurch, he had overstepped.

"Tom, you didn't ask me about this and now its all arranged, it seems you aren't asking but telling." She said sternly then a board smile spread across her face and she reached to hug him. "What a wonderful surprise, I'm really pleased you want to continue our journey. I wondered if maybe the party had gone a little too far for our new relationship." She felt Tom relax in her arms and she kissed him gently.

"That's a relief Miss Jessica, I'm really enjoying the experiences we are having and I think I want to move forward in the next week if that's OK? I don't know what the next steps are or how they would impact my life at home."

"We don't have to do everything all at once silly, its like any other relationship just with far better and dirtier sex." She chuckled at his discomfort. "The next stage would be for me to collar you as my submissive, a little like marriage but not so formal and certainly not so legal. We would then look at where we go from there once we have made pledges of trust to each other. I'd love to have you more local, perhaps even move in but that might not be the first move"

"I'd love both of those things Miss Jessica, as long as we can continue as we are, I'm enjoying being submissive and the sissy thing is becoming a pleasure too."

"Of course Tom we would continue together but you need to appreciate you may not be exclusive to me and I may not be exclusive to you in the relationship, its like marriage but different. I like to fuck a variety of men, and women, as you've seen with Dylan. I also love watching you be used by my friends and their subs too. Would this be OK? Are you OK with sharing?"

"Of course Miss Jessica, I've been pleasantly surprised how much multiple partners can be fun, as long as we don't lose the 'us' time completely." She hugged him tighter and kissed him, deeper this time.

"I'll don't think I'll ever tire of our personal time together." He returned the kiss and their lipsticks smeared together and passions were ignited once more. Breaking the kiss she said "I have an appointment later to go and visit Miss Michelle and Miss Lucy, would you like to come and play?"

"Yes Miss Jessica, very much, Miss Michelle was wonderful"

"Excellent sweetie, I'll text and ask if its OK for you to come along, perhaps I'll let them play with your triggers while I deal with their errant submissive. Would you be OK with that? Letting someone else have access to your trigger words?"

"I think so Miss Jessica, Miss Michelle was a lovely person and lots of fun in the bedroom, maybe I'll learn something new I like."

"I'm sure they would enjoy test driving a perfect hypnotised submissive while I enslave their current boy slave. I'll text them now, in the mean time why don't you give me my first orgasm of the day." Tom grinned as she guided him off the sofa and onto his knees.

He didn't need any further hint as she slipped her skirt up revealing her naked pussy and stocking clad legs. He slipped his head between her parted legs and his tongue into her warm waiting slit. Her musky scent washing over him and overwhelming him with desire.

Quickly he found her clit, her gasp of pleasure confirming his accuracy. Her hands clasped behind his head as she gently held him in place ensuring he stayed on target. Flicking her bean with his warm tongue she found a grinding rhythm and her legs were soon quivering and her snatch pulsing in anticipation of her climax. Her moans grew louder and more guttural as her orgasm approached, her grip on his head became more firm to ensure not one lick was misplaced. It wasn't long before he whole body was shaking and her moans had become screams of pleasure as her climax washed over her, her back arching in spasms of delight.

Tom continued to lap and lick her now dripping pussy until he felt her calm and her grip on his head relaxed, indicating she had got what she had desired form him. He lay his head on her thigh occasionally licking her clit gently enjoying her twitches and jolts as he did so. She ran her fingers through his hair as she came down to earth.

"What a good little cunt licker you are Tom but I think you might need to look at your makeup before we go out" She said huskily as she enjoyed his totally ruined makeup that had been so perfectly done when he had come to see her. "But first my sleepy submissive...." She paused as his trigger took hold and he relaxed against her leg and his eyes closed on cue, "For today only, my sweet sissy, all of your triggers can be used not only by me but by the lovely Miss Michelle and Miss Lucy. You will be your perfect obedient self as always but they will be able to trigger your sleepy submissive state, trigger your erections and orgasms just as I can. Do you understand my sweet?"

"Yes Miss Jessica" he mumbled, a smile slowly crossing his face she knew was due to him pondering the possible lit use of someone else having his reigns for a while.

"Any triggers or commands they insert will only work for today and you will instantly forget them when you go to sleep tonight, there will be no lasting control or suggestions after we go to bed." She continued to stroke his hair and felt him nod in agreement.

"What a good sissy you are Tom. Now, you'll wake as I click my fingers and go and get cleaned up. Put on something good and sexy for meeting my two friends and make sure your makeup is extra specially slutty, I think Miss Michelle really enjoyed you being a wanton slut!" And with that she snapped her fingers. Tom awoke and enjoyed a few moments more against her smooth silky thigh before getting up giving her a respectful kiss and going upstairs to choose his outfit and decide how to make himself into a very slutty sissy.

Giving the joy of obedience

"Shake a leg Tom." she said lightly as the limo pulled up to the large modern detached house and the gate buzzed open for the them to drive in. Tom slipped back from his glassy day dream and felt his excitement build at the new challenge ahead of him. He'd never been handed over completely to someone other than his Miss Jessica and it both excited and frightened him as to what might happen.

Jessica loved his slutty look, he'd really gone to town, just as she had told him to. He had traded the favourite red and blonde wigs for a glossy black bob style. His eyes were adorned with long obsidian black eyeliner along the top of his lid and a deep red liner along the bottom lid giving him perfect long cat eyes. Above the obsidian black of the liner was a shimmer of dark charcoal into a dark glittery grey in the upper part of his lids. His cheeks were contoured and highlighted heavily like an instagram model and his lips were a deep burgundy to match his lower eye-line. A collar around his neck adorned in diamanté with the word SISSY.

His dress was a tight burgundy leather corset dress, the skirt of which hung just too short so that his black lace stocking tops showed along with the telltale pull of his many garters. At the top of the corset dress she could see the telltale lace of his bra holding in his ample C cup breastforms. He screamed 'fuck me right now" and would get what he was screaming for in short order she was sure.

Jessica slipped out of the open limo door, her flowing skirt slipped easily over the leather seat and hung perfectly from her hips showing just a hint of stocking above her long knee length laced boots in the slit that ran up her leg. Her bodice was black lace and red satin holding her cleavage in check without any visible signs of how. Between her breasts hung a gold locket on a long chain allowing it to sit perfectly on her chest. Her face was all business, subtle brown shimmering eyeshadow and modest wing to her eyeliner, a dash of blush on her cheeks and her lips covered in the perfect matte red of the Armani lipstick Tom had bought her. She was striking without being overpowering.

Michelle and Lucy Stood at the bottom of the entry steps to the house, both dressed in figure hugging dresses that highlighted the glorious curves of their figures. Hints could be seen through the tight material of the expensive and explicit lingerie that lay beneath. Michelle wore a striking red lipstick that inevitably grabbed Tom's attention, her full lips just played to his fetishes. Lucy was less bold, sporting a creamy nude colour on her lips but more than making up for it with the ornate emerald eyeshadow that highlighted her bright green eyes.

"Thank you so much for coming to see us Lady Jessica." Lucy said first "I'm so sorry I couldn't attend the event a few days ago, Michelle has told me so much about you and your techniques."

"It's a pleasure, and please, just call me Jessica, titles are for subbies and formal events only" Jessica replied. "May I introduce my... I guess, betrothed submissive sissy, Tom." She gestured to Tom as he stood behind her with his head bowed holding a small gift wrapped box Jessica had handed him as they got out of the car. "Tom you remember Miss Michelle and this is the divine Miss Lucy." Tom politely curtsied. "Tom will you please give Miss Michelle and Miss Lucy their gift for having us to their lovely home."

Tom stopped forward and knelt before the two women and offered the small box to them, ensuring to keep his gaze obediently to the floor.

Lucy accepted the gift, "What a delightfully well behaved sissy you are, shall we go and open this inside." They all filed in through the ornate wooden doors, Tom following at the back teetering on the ridiculously high pornstar heels he had chosen. They entered into a modern sunken lounge with plush leather sofas in an L shape on both sides. A strong fire was burning in the large fire place in the centre of the room.

To one side of the sunken area a man sat on a heavy uncomfortable wooden chair his hands and feet were cuffed to the arms and legs of the chair securing him in place. He was naked but for a pair of tight latex trunks and a laether collar around his neck. He was quite handsome, with well kept short blonde hair and a square jaw, his body toned and muscular.

"This is our submissive 'Jacob', you recall him from the event I'm sure" said Michelle "he's yet again been a naughty boy but we caught him trying to jack off despite being in chastity. He just can't seem to help himself. A good reflection on us and our allure but still very irritating."

The three women sat on the plush sofas and Tom Knelt on the plush rug in front of Jessica. "So what do we have here?" Said Lucy holding up the gift wrapped box with a broad smile. "May we open it?"

"Of course." Said Jessica.

Michelle leaned in and pulled the delicate ribbon and bow loosened and fell to Lucy's lap, Lucy then opened the box, pulled out the small leather bound notebook inside and opened the cover. "The Keys to Sissy Tom." She read out quizzically.

"Well," Jessica began "As you wish me to work with your submissive I thought perhaps while we have out first session you might like to test drive the final product. Inside you will find a list of all of Tom's trigger phrases and what they will trigger in him. Tom has consented to allow these triggers to be used by you both for this evening so you can get an idea of how powerful hypnosis can be and which triggers you might enjoy using with young Jacob here."

"Wow, so we can sort of control him?" Said Lucy trying to comprehend.

"Perhaps you would like to try the one on page 4 for starters? Michelle has seen this one so maybe you can try it Lucy? Tom why don't you stand and face Miss Michelle and Miss Lucy."

Tom stood and walked to where Jessica had gestured, "now raise your skirt sweetie." Tom raised his leather skirt revealing his limp cock, no panties as sluts don't wear panties. "Go ahead Lucy."

"Tom, erm, could you 'rise to the occasion'" she giggled slightly and then looked in awe as within a moment of her saying it his cock blossomed to a full blown erection. "Oh my, Tom, are you pleased to see me?" She quipped chuckling further.

"Now try the one on page 5." Said Jessica.

"Tom sweetie why don't you put it away" sure enough the erection quickly softened back to its normal flacid state. "Wow, I've never seen that happen before."

"Its quite special isn't it?" Said Michelle. "He can't cum at all unless given permission by a trigger, so you could ride him all night and he'd just get more and more frustrated and horny. Can you imagine the fun we would have with that. Well the fun I have had to be fair, but you know what I mean."

"I think I can." Lucy leaned and kissed Michelle passionately, "This is awesome! And you're going to let us play with him while you do something similar to Jacob?"

"I am yes, he's yours to play with all night while I deal with our problem boy over here. I'm looking forward to the challenge to be honest so please feel free to enjoy Tom all night and I'll give you a call when we have made some 'progress' with young Jacob here. I know Michelle enjoyed Tom at the party and he was a very slutty sissy then so I made sure he was extra slutty tonight just for you."

Lucy stood and took Michelle by the one hand and then Tom by the other "I don't need to asked twice to play with new toys, come on lover, lets see how well this hypnosis thing works and see if we can teach this slutty little sissy something new." Jessica smiled as Tom was lead away from the lounge by the ebullient Lucy and down the stairs into what she suspected was a rather splendid modern play space.

"Ladies, do save the last trigger till later in the evening, I think you know which one!" She called after them.

***

Tom was lead into a modern, subtlety lit play room, more 21st century than the more often seen Dracula stylings of many play rooms. The paint was clean and crisp, the lighting soft and muted, the equipment modern and shiny.

Lucy peaked her hands as she tried to decide what to use first, new to BDSM as she was, having been introduced to it by her wife, Michelle, she was learning the ropes quickly. "I think we should make sure he's all clean before we get too excited." She said walking over to what Tom recognised as a gynaecologist exam chair similar to the one he had been used upon with Jessica. Lucy patted the soft leather of the chair inviting Tom to sit.

He slipped onto the soft white leather and was guided back onto he soft white back of the chair. Lucy began to unclip the fasteners on his corset and he breathed easier as the cinching of the dress was released. "I love unwrapping gifts" Lucy said as she slipped the corset dress away from him leaving him in a lace basque with thick garters holding up his ultra glossy nude stockings.

Michelle slipped plush leather cuffs onto his wrists and ankles and placed his legs in the stirrups leaving him completely exposed. Then she clipped his cuffs in place and fastened thick leather straps over his waist, chest and neck. Completely immobilised Lucy rubbed her hands with glee as she wheeled her stool across along with a covered tray.

"Sleepy submissive" said Lucy and Tom went limp and his eyes closed instantly. "Oh this is going to be fun! Tom, can you hear me?"

"Yes Miss Lucy" he said quietly

"Good boy, now I'd like you to be very positive this evening and be our little yes man. You no longer know the word 'no', only yes will do when you are asked if you want to do something or if you are invited to experience anything. Do you understand Tom?"

"Yes Miss Lucy"

"Good boy, now wake up when I snap my fingers" SNAP. Lucy clapped her hands with glee as tom's eyes flickered open. "Tom, have you ever had an enema?"

"No miss Lucy." he said with a quizzical look on his face

"Would you like one?"

"Yes Miss Lucy." he said straight away his face even more puzzled as the answer came from nowhere.

"I thought you might say that so we have everything ready to go, Michelle, he said yes!"

"I know, I heard." Said Michelle as she wheeled a drip stand from behind a white medical screen. Michelle had also lost her dress and was now decked in a tight fitting nurses outfit which was just a little too short to hide her stocking tops. In one hand she held a 6 inch long smooth, brushed aluminium probe with a small aluminium tap at one end. From the tap snaked a long tube up to the drip bag hung on the stand. She grinned as she positioned herself between his legs and lubed the probe with a couple of pumps of a bottle on the tray.

"You might feel a little pressure Tom but then it will all be over." before she lowered her gaze and Tom felt the cold metal probe push against his sissy hole. He felt the probe pass smoothly through his sphincter and breathed out as it went deeper. "What a good sissy, you see no drama there. Now we just turn on the flow and we'll have you all cleaned out in no time"

Michelle turned the spigot and Tom felt a cool sensation in his ass as the fluid began to flow into him. Lucy got close to his ear and whispered "You see, all that fluid is going into you. Its quite a lot isn't it, 2 whole litres flowing into your butt hole. Then we have to wait and hold onto it while it gets things moving inside. You need to fight the urge to go to the toilet at first but we'll try to help with that." Tom lay his head on the soft padding behind him, trying to relax and process the new sensations. "Rise to the occasion Tom." Lucy whispered and his cock hardened immediately, his arousal growing by the second. He soon felt the warm soft sensation of Michelles full lips slipping onto his cock and her beginning to tease him with her tongue. Again he breathed deeply.

It took 10 minutes or so before the entire bag of fluid had drained. Tom felt full but not uncomfortable. Michelle had slipped her lips from his sissy clit a few moments before the bag went dry. "Good little sissy, I thought you would have been fidgeting and making a noise well before the whole thing ran through. Especially with me sucking you off." She checked her lipstick in the mirror and giggled at the smudges on her chin, she did enjoy giving a good blow job every so often. "As Lucy said the fluid needs time to work and you'll tend to have a few cramps but you need to work through them. The toilet is just over there and you'll be free to use it once I am happy a reasonable time has elapsed."

Michelle unclipped his cuffs and unfastened the large straps over his midriff to allow him to move but held him in place with her hand. Lucy sat on the stool where Michelle had been, between his legs and slipped her creamy lips over his rock hard cock. Tom took a sharp intake of breath at the warm soft sensation of her engulfing him. Michelle took her lipstick and reapplied the deep red to her lips as Tom became lost in the stimulation. "You're getting better and better at cock sucking lover." Michelle said as Lucy slipped his cock in and out of her warm mouth "See him starting to squirm and breath faster? He must be fit to burst, and yet he can't. What a wonderful level of control. Imagine if he were to 'tip over the edge'"