Jessica and Tom 02: Meeting Up

"Oh she looks good enough to eat." Janice gushed as she began to survey Tom and his current attire. "Did he choose this himself?"

"He did, he didn't know we were going out but it was his choice." Jess chuckled

"Oh Jessica you are such a tease," Janice chastised "The poor boy must be awfully embarrassed."

"You have no idea" Tom chimed in. The sharp slap across his buttocks was instant

"The adults are talking sweetie, don't be rude and embarrass me." Jessica snapped

"Sorry Miss Jessica."

Turning back to Janice "Do you have the outfits we discussed for the party."

"Of course, yours is all finished and I have the selection of outfits you wanted for this pretty little thing, come lets try some of them on." Janice turned on her heels and minced towards the back of the shop her stride restricted by the tightness of her dress. Tom followed in trail of the two women wondering what was next.

The dressing room was simple, a large rack along one wall held a selection of rubber outfits hung neatly, ready for their customers. A large chaise was at the centre of the room a gleaming champagne bucket with a fresh bottle sitting chilling in anticipation. The wall opposite the rack had a large mirror sitting in a delicately carved oak frame. A curved rail held a heavy silvery privacy curtain that was tied back to the wall with a silky thick golden rope.

Janice beckoned to the chaise and Jessica relaxed into the thick cushions taking a load off her feet with a sigh. Tom went to sit next to her but was met with a scowl "Over there darling, its your fitting." She pointed to the area in front of the mirror.

As Tom found his mark Janice uncorked the bottle with a pop and poured a glass of golden wine into a delicate flute handing it to Jessica before pouring one for herself. "Now shall we see what we have to work with? Why don't you undress dear?" She smiled brightly at Tom and nodding encouragingly as he looked between her and Jessica.

"Come on Tom, its not like your outfit is hiding many secrets." Jessica cajoled

Tom reluctantly began to unbutton his blouse revealing the delicate lace bra, then after hanging the blouse on a hanger unzipped the side of his skirt and slipped it to the ground before folding it neatly and placing it on the chair. The chill in the air made him goosebump as he stood in just a bra and pair of hold ups as the two ladies enjoyed his discomfort.

"We have to keep it a bit cool in here or you tend to have trouble getting into the outfits." Janice said as she minced to the rack and picked the first little number she had for him to try. "Do you keep him locked up in that all the time?" She asked casually

"No not all the time but my aim eventually is to have him be so submissive he wont need to wear it, I caught him playing with himself a few days ago so thought he should stay locked up till we deal with his etiquette."

"Very wise my dear, orgasm control does give the best result for submissive sissies like this one."

The red latex dress was a knee length pencil dress a little like the one Janice wore, fitted with cute short sleeves and an integral boned corset to ensure a feminine shape. Janice loosened the lacing down the back and handed it to him. "just step into it and pull it up and we'll get you fitted up in a jiffy."

Tom placed the dress carefully on the floor and stepped into it, careful not to snag his heel on the rubber. He pulled gently and the dress slid up his stockinged legs and up to his hips. A little more effort was needed from there on it as the dress slipped over his pelvis and up to his waist, the constrictive latex hugging his body sensually. He got the bodice positioned over his bra and wriggled to get it comfortable then tried to straighten the dress of its wrinkles.

Janice approached and helped him straighten things out then swept behind him and began to tighten the laces of the corset. With each pull he felt the familiar breathlessness return as his waist was tucked into an hourglass shape. The laces tied off Janice retreated back to the chaise to enjoy the show.

"This isn't my favourite but its the best all rounder that maybe could be used again for a less formal gathering. I think we can do better but we have to start somewhere." Janice said as she sipped her wine.

"Tom sweetie give us a twirl. I like the pencil skirt and corset but its not as classy as I hoped and comes across as a bit cheap on him." Tom turned on the spot, the tight rubber squeezing and stretching as he moved trying to give the ladies the best view he could. "No not this one, I agree." said Jessica discounting the first outfit quickly. "Although it was fun watching him wriggle into it."

The pair giggled and Janice got up to help Tom out of the corset and slip the dress off leaving him once again exposed. Having hung the dress on the rack Janice picked the next choice, a deeper red and far longer than the last with the bottom trailing slightly on the floor as she handed it to him. She unfastened some of the rear straps and opened the back out showing him where to step into.

Tom again carefully stepped into the gown and the rubber slipped up his legs and over his waist the resistance growing as more of the dress clung to him. he put his arms through the long full length sleeves and pulled the high halter neck up. Janice first fastened the halter neck at the back then worked her way down the back refastening the straps she had released. Tom felt the reassuring tightness of the dress as the straps sealed him in. He could see the attraction of the rubber fetish. The pencil skirt restricted his ability to walk just like Janice's did but there was something else about this dress he couldn't put his finger on yet.

Janice fawned over the outfit, making sure everything was flat and all the straps straight. Its tight form gave Tom a pleasing feminine figure all the way down to the low hemline that hung just above his ankles.

"This is very classy." Jessica said "but I'm not sure its right for the party"

"Tom, why don't you give Miss Jessica a twirl?" said Janice allowing her hand to guide him. Tom obeyed and started to turn.

"Oh!" Jessica exclaimed as she caught her first glimpse of the surprise. The dress had thin straps all the way down the back as they had first seen when he stepped in but they were followed by a void now filled with Tom's naked ass. As her eyes descended she saw more evenly spaced straps all the way down the long skirt. 75% of the back of the dress was open to the elements allowing a very clear view of the wearers naked form within. "Its very good but what about access."

"Ah I see what you mean. All the straps are fitted with the same quick release buckles, you can keep them all fastened and keep the pencil dress look or open them up from the bottom to allow it to flair out. If you release all the lower ones the dress will easily peel open and you can have full unfettered access to everywhere below the waist."

"Oh this is a fun one, not sure about the walk through town though, might need some accessorising. What do you think Tom?" Tom looked over his shoulder at the exposed rear of the dress and gawped.

"I cant wear this in public Miss Jessica!" He pleaded

"Come sweetie, don't you think it would be fun to be able to unclip those straps and peel the skirt forward so some young stud can fuck you. It really is quite the outfit!" Turning to Janice "I'll take this one but not for this party, I love it. Whats next?"

Having unclipped all the straps Toms arms were slipped from the sleeves and the dress rehung ready for packaging. The final item Janice had on the rack was presented. As before Janice showed Tom how to step into the outfit and then allowed him to slip into it.

The rich ruby coloured rubber slid up his body and he slid his arms into the short sleeves. The short pleated skirt hung well above the knee and splayed out pleasingly like the schoolgirl one he had entered wearing. The high mandarin style collar wrapped his neck and Janice helped clip the poppers down the long black trimmed diagonal line that ran from neck to armpit. The Oriental influence was obvious, reminiscent of a very kinky geisha or Japanese bar girl but with a more modern twist.

"Now that is perfect, subtle, classy but tarty and the shade is perfect, I think we have a winner!" Jessica exalted grinning in triumph. Janice joined her on the Chaise and sipped the cool wine from her glass.

"I knew you'd go for this, its perfect I agree. Suits his figure, you can easily flip up the skirt to tease or punish and it looks so gratuitously feminine and classy"

"What do you think Tom?" Tom modeled in the mirror trying different poses. he couldn't find fault in it, if he didn't know the reflection in the mirror was his own he'd have been really very interested in seeing more of the lovely young thing"

"I love it Miss Jessica!" he blurted out, surprising even himself with his enthusiasm.

"Excellent, why don't you come over here and kneel in front of us and thank Miss Janice properly?" Jess winked at Janice as Tom knelt in front of the rubber goddess.

"Thank you so much for finding such a wonderful outfit for me Miss Janice."

Janice Leant forward very close to his face, he could smell her thick perfume and admired her thick red lips as she spoke "You are so welcome my sweet sissy." as she leant back Tom heard a zipper being run and saw Janice's tight skirt slip open revealing her soft nylon clad thighs.

"I said properly Tom!" He looked confused at first before he saw Janice suggestively part her legs to show her naked pussy lips glistening in anticipation. He grinned and leaned into her warm crotch allowing his tongue to slip into her sweet sex. Hearing her gasp as he searched out her clit Jessica shifted in her seat and took Janice in a passionate kiss as she firmly massaged the rubber clad lady's ample breast and caressed her soft thighs. The moans of passion swept through the empty shop as the grateful couple pleasured Janice to her quivering climax.

The deepening

Over the next few days Jessica repeatedly triggered Tom's sleepy submissive state and deepened his trance level. She slipped him down elevators and staircases in his mind until his only desire in life was to please and serve her. It wouldn't be long before her control over his conscious mind was almost total. The time had come to try to inch her way into his more physiological functions and begin to have direct control over his ability to be aroused in much the same way she had with Dylan but this would be more cerebral.

She slipped into his bedroom her satin neglige billowing behind her as she moved across the room. Tom lay in the luxurious soft bedsheets on the edge of sleep and wakefulness, the perfect time for her to intervene.

She slid carefully under the soft duvet and spooned with him allowing her body to make the maximum contact to his she felt him adjust his position to enjoy her warm touch. She whispered softly into his ear "Sleepy Submissive." and his movement stilled and she enjoyed his full entranced attention.

"Tom, you are such a deeply entranced submissive now and we now need to work on your behaviour for our upcoming function in a few days. We are going to try a few new things to build on the journey we've already made and you will make such a good job of it I'm sure." She saw him smile softly at the praise.

"First we need to reinforce our no touching rule, as you already know a good submissive doesn't play with his Mistress' things without permission does h?e"

"No Miss Jessica." he mumbled

"Good boy Tom, now who owns your cock Tom?"

"You do Miss Jessica."

"Excellent Tom, I'm so pleased you agree, now since I own your cock do you think you should play with that cock unless you have my permission?"

"No Miss Jessica, it's yours."

"Good boy, so we agree that you won't try to play with yourself unless I expressly give you permission, no secret rubs in the shower, no gentle caresses when you adjust your pretty panties no matter how horny you become."

"No Miss Jessica, No touching at all." he said softly

"What a good submissive you are Tom.Today we'll see if we cant take that chastity device off and see how well this command has settled into your mind"

"Now Tom, next we need to work on your arousal, what makes you sexually aroused Tom?"

"Mmm you, Miss Jessica, silky things, being controlled, being made to do naughty things."

"Oh I know all of these things are such wonderful experiences Tom, but I Think we should make it very simple, even simpler than you've just described, does that sound nice Tom?"

"Mmm yes Miss Jessica."

"Good boy Tom, how about we make it so that only I can arouse you sexually and that will only happen if I say a certain phrase. Without it your little sissy cock will stay small and soft and you won't become aroused at all, does that sound nice Tom?" He nodded slowly "So Tom if you hear me say or whisper 'Rise to the occasion' you'll know that I want you to be aroused and you will be free to enjoy any erotic sensations you feel and allow your little sissy cock to get hard. You'll still be excited by erotic happenings without the trigger but your little dick will not respond to this excitement without my trigger." Again a nod confirmed he'd understood.

"If you hear me say 'put it away' you'll know its time not to be aroused and your mind will ignore any erotic things happening to you and you'll soon become small and soft again."

"Yes miss Jessica." he managed to mumble

"We'll test this out in a little while." she took the key hung on her necklace and released his chastity device and slipped it off. "Tom, we have one more thing to play with and for that I'm going to need you to be very aroused my sweet but you wont cum like a man, there will be no gooey cum to gobble up this morning. I'm going to bring you to height of orgasm and then when you are there i'll ask you to remember both how you got there and the fabulous sensations of a dry orgasm and we'll associate that wonderful feeling with a trigger allowing me to bring you there again and again on command."

"So my sweet think of a very erotic arousing moment in your life, let your juices start to flow as you slip into the moment and tell me where you are."

"In the play room Miss Jessica, with you and Dylan."

"Very good Tom, are you on the bed with us watching me kiss my stud?"

"Mmmhmmm."

"Watch as my dark red lips kiss his lips and I work down his hard glistening body, I know you love my lips Tom. Can you feel your arousal building?" She gently began to caress his thigh alternating between her sharp red nails and her soft finger tips. She could hear his breathing speed up as he visualised her kissing Dylans fabulous body.

"Keep watching Tom as I turn and slide his hard cock into my warm wet slit taking his whole length into my hungry pussy." She used her other hand to play with her own sex as she day dreamed the moment she was describing to him, "can you see me gasp as I take him all the way into me and his throbbing cock rubs against my clit." She gasped for effect and she could see he was beginning to grind slightly with the rhythm of her voice, on the upstroke of her hand caressing his thigh she could feel his cock was rock hard as his arousal steadily built.

"Remember Tom, you mustn't ejaculate without my permission and I'm going to continue to arouse you till you have a full orgasm. Watch me thrust up and down his glistening shaft Tom see how my supple skin moves as I ride him, the way my garters stretch over my pert ass as they keep my black stockings neatly in place." A moan escaped him as he surrendered to the moment imagining her tight ass framed by her perfect lingerie.

"Now see him bend me onto all fours and begin to drive his dick into me doggy style, pounding my pussy as I begin to moan." which she did as she slipped her finger deep into her pussy and found her g spot. "Watch a real man fuck me, his big dick impaling me as he thrusts into my snatch. My dark red lips open as I moan more and more and I being to tremble, my orgasm creeping up to its peak."

"Tom, on a scale of one to ten how close to cumming are you now my sweet, watching Dylan fuck me?"

"Seven, almost eight Miss Jessica." he said between short breaths, she could see the tell tale shake through his torso of an impending orgasm and relished pushing him over the edge.

"I want you to get your head right under my pussy, to catch all the sweet cum when it finally sprays out Tom, I know how much or a cum whore you are my sweet and I don't want you to miss out." He was moaning often now as his mind was overstimulated by both the mental images she was describing to him combined with his deep seated desire to obey and please her. "Tell me when you are on the edge of climax my sweet so we can all cum together."

"Can you see my juices coating Dylans hard cock as he pounds in and out of me."

"Mmmm." he moaned weakly "I'm on the edge Miss Jessica."

"Good boy Tom, now remember this sensation, with your whole body quivering and bucking, you moaning in ecstasy and when I say 'tip over the edge' you'll feel your mind explode in a dazzling orgasm. You wont ejaculate, you'll just have an amazing climax do you understand Tom?"

"Yes." he moaned

"Dylan gets to cum." she whispered as she herself moaned into her orgasm "Tip over the edge, see Dylan explode in my wet pussy as I cum on his hard shaft and our mixed juices drip from my pussy into your mouth."

Tom bucked and moaned loudly, arching his back and shaking uncontrollably pre cum oozed from his hard cock but no cum erupted. His breathing was fast and hard as he began to come down from his dry orgasm. She saw him lick his lips as he imagined licking up the dripping mixture of Dylans white salty cum and her own sweet gushing nectar.

"Calm now Tom, slow your breathing my sweet coming back down from your wonderful climax." when I count to five you'll slowly wake from your trance feeling refreshed and very aroused having had an amazing dream about us all fucking in the basement. One, two, three feeling more and more away, four, eyes opening, and five."

Tom's eyes flickered a few times and he stretched as he woke his cock was very hard and weeping precum as he turned to enjoy the view of a rosy faced Jessica in bed either him.

"When did you get here Miss Jessica."

"Oh a little while ago, I didn't want to wake you, it looked like you were having a lovely dream."

"Oh I was, it was very hot."

"Put it away." she whispered

Almost instantly the rigidity of his body relaxed and she could see his cock start to soften, she tested the trigger by starting to caress his thigh again and kissing his neck playfully but his cock was softening back to his non aroused state. "You are such a wonderful subject Tom."

"What do you mean?"

"Tip over the edge." she responded to make the point, he bucked and shook instantly as he was transported to that moment of mental climax. He arched his back in ecstasy as he came in his mind and she chuckled at his soft flaccid dick swinging between his legs 'mission accomplished' she thought to herself.

She slipped out of bed to let him come down from his second orgasm of the morning in his own time, 'that could be fun down at the mall' she thought to herself.

Tom appeared downstairs about an hour later, his dressing was getting better and better by the day. His choice of outfits was moving from the overtly tarty to the sophisticated and sexy, likely taking his cues from her own choices. His makeup was also seeing significant improvement after she had allowed Tom to recall some of the events when he was in his Candi persona. She was genuinely enjoying Tom more than Candi now but Candi was fun from time to time as he was a complete bimbo interested in nothing but his looks and getting fucked in any degrading way he could. Tom on the other hand was much more reserved and had to be 'encouraged' into her desired levels of depravity.