Jessica and Tom 02: Meeting Up

Next to the simple bench was a much more purposeful bench. The tall box was extravagantly covered in soft leather and tilted slightly forwards towards what he thought was the front. Thick leather straps with strong steel buckles hung down from their anchor points. The bench then had a drop to two smaller benches that were on a similar angle to the main part of the bench but at a lower level, these also had a myriad of straps hanging idly from them. Tom realised this was designed to have the submissive lie face down, the smaller benches were for the legs and could be spread or closed using heavy locking pins.

Between the leg supports was a device about the size of a shoe box from which, a long steel rod protruded. At the end of the rod was a threaded end to add some kind of attachment. The device had a control box with a dial that could be turned and it was clearly electrically powered

Between the two benches Tom saw the large dark oak display cabinet holding a wide range of dildos and toys, his eyes watered with the possibilities. He opened the cabinet and took one of the dildo's out. It was heavy and firm in his hands, shaped like a realistic penis but much bigger than his own. He saw at the bottom a plate containing a threaded nut and soon realised what the small electric device was for, a fucking machine. He quickly replaced the dildo in the cabinet and continued to explore.

The final piece on this side of the room was a heavy oak chair, if it didn't have large metal manacles for the wrists arms, ankles, legs and neck he'd have assumed it was another throne but this was obviously for restraint. In the bottom of the seat he noticed two flat pieces of metal where the submissive buttocks would go. Each had a wire embedded in the wood that lead off to the side of the chair where a simple controller hung on a hook. It had one dial and one big red button but nothing else, no markings indicating heavy use over the years.

The other wall was different. While the one he had just investigated was very medieval this was verging on modern. An old style medical screen with 4 panels on wheels was pulled across one section. The old blue plastic screens had been replaced with shiny black rubber but he could see the vintage from old movies. Behind lay what looked like a full medical suite. All in black leather and black painted steel.

The first piece was a kind of short seat come bed which had poles coming up form the foot end. On the poles were padded half tubes that ended in a foot plate. Leather straps hung from the chair and the half tubes. This was a gynaecologist chair. The leg holders could be moved left to right to almost any position allowing easy access to the 'patient'. Wheeled medical trolleys sat at either side of the chair and a brief glance revealed all sorts of packaged medical supplies from bandages to hypodermic needles and beyond.

Next to the gynae chair was a more recognisable device. An old style dental chair. The 1950's design fitted the menacing room to a tee. It bore an amazing resemblance to a barbers chair but the headrest was more clinical with its two circular leather pads designed to hold the head immobile especially when strapped in. The large black enamel pedestal held the reclining controls as well as articulated arms that provided the user light and trays upon which to store their implements of torment. As was the theme for the room leather straps dangled in the cool air waiting to restrain their victims.

After the medical area was a large dresser with bright Hollywood style makeup lights around the mirror. An embarrassing amount of makeup was neatly stored in trays on the smooth oak counter. A few wigs sat on black lacquered model heads. He vaguely recalled sitting here as Jessica touched up his makeup before things greyed out again.

A door led to a large modern bathroom with oversized walk-in shower, toilet and basin. Next to the door was a large closet containing yet more outfits in PVC and leather and another cabinet filled with toys, leather cuffs, chains ropes and several things Tom was yet to identify.

An empty area confused him a little, it was obviously a space where something happened. A large leather cocoon hung on the wall as did several frames and straps. A large yellow industrial control box hung from the ceiling and he traced the wire into the roof where he saw two large metal hooks from which hung a steel frame with eyelets welded to them in a symmetrical pattern. Pressing one of the buttons on the control box saw the hooks and frame descend pressing the other caused them to go back up into the roof.

Almost back to the wheel he found a leather covered saw horse with steel eyelets on the legs another selection of whips and canes hung from their hooks to one side of it.

The whole room was quite a departure from what he had ever imagined. He had seen pictures of dungeons but never been in one. It was a bit overwhelming as he thought of the possibilities that the room held. In the porn he had watched over the years he had seen people trussed up in similar devices and enjoyed imagining himself in such a predicament but now it was very real. He imagined the helpless immobility of the spinning wheel, the cocooned sensation of the leather bag as he was hoisted from the ground. Being strapped to the medical chairs and having things probed and tweaked. His cock was very hard now his imagination running away with himself.

he sat on the soft bed luxuriating on the satin sheets as they slipped over his smooth body. Instinctively he began to rub his rigid cock and he became more and more aroused as he soaked in the glorious smell of the leather and the musky scent that was left from last nights entertainment. He was on the brink of cumming but it just wouldn't happen. He took some lube from the nightstand and still the moment would not arrive no matter what he tried to bring himself to cum.

His blood ran cold when he heard the gentle clip of shoes on the concrete steps outside the room and Jessica appeared through the door. Her figure was amazing in that skin tight jersey dress. She frowned when she saw him high his hand wrapped round his cock, it glistened with wet lube in the dim light.

"Hmmm if we are going forward I'm going to have to work on that trigger, I very specifically told you not to play with things that didn't belong to you and that cock is mine!" She smiled trying to defuse his embarrassment. His face said it all, he was like a teenager caught jacking off by his mom.

"Don't panic sweetie I'm not upset with you, I said you had the run of the place and I hoped you would venture down here, its such a wonderful play space. You were down here a while and I thought I'd best check you hadn't got yourself snagged up in something." he visibly relaxed as she sat on the edge of the bed next to him and tenderly stroked his thigh.

"I am pleased that you're having trouble cumming though, that suggestion seems to be working very well." his face screwed up as he remembered what she had told him earlier.

"Really I can't cum just because you told me not to?"

"Yes pretty much, your desire to be submissive works in conjunction with my suggestion that you may only cum when given permission, it looks like you've been trying a while and all you have is a few drops of precum so I'd say its working quite well but you're welcome to continue trying. Perhaps if I give you some more stimulation that might help?"

She slipped the shoulder of her dress revealing her expensive lace bra then slipped the other off allowing the dress to fall to her waist. Tom began to stroke again as he watched her rub her hands over her ample breasts. The desire to cum was almost unbearable but still he couldn't reach that point of no return. "Still nothing?" She teased.

Jessica stood and slipped the dress over her waist and let it pool on the floor revealing the rest of her smooth body, her matching lace g-string barely covered her pussy and her nude stockings were held up by a matching garter belt which seemed simply too small for the job but yet managed to keep everything in place. She bent and rubbed her hands over her perfect ass, running her nails all the way up her torso just like in the more racy music videos of the recent years.

She sat back on the bed "perhaps if i help you stroke?" She slipped her smooth hand onto his member and gently rubbed him up and down with one hand while caressing his thighs with the other hand. "Isn't this exquisite, you are stuck right at the edge of cumming and yet still nothing, you are such a good subject my sweet."

Tom was in a daze now his mind was spinning with lust and his desire for release, he'd do anything to be allowed to climax, the teasing was overwhelming.

"I bet you'd just about do anything to be allowed to cum wouldn't you my dear."

"Yes Miss Jesica anything, I'm so close."

"I thought so, this one will be free.. kind of. It will also be a good demonstration of how powerful my hypnotic hold on you is and how erotic and arousing that hold can be."

She opened a drawer by the bed and took out a large shot glass and a black silicone chastity device with a lock and placed them on the bed. Using one hand she positioned the glass over his tip then using one finger began to run the sensitive area just below his cock head. He bucked and shook involuntarily as drips of precum slid into the glass.

"Candi gets to cum." she whispered in his ear. His moan was instant and his dick throbbed and twitched as his orgasm arrived instantly. His white cream spilled into the waiting glass and she carefully collected all of it as his trembling ecstasy subsided.

"You see Tom, one phrase and you had your release but this trigger is two fold. Firstly I allow your release but I also suggested you would do anything for me afterwards as tribute for being so generous and letting you cum. You're fully awake and no other triggers are in play and yet..." she handed him the glass of warm cum "you are going to drink all that lovely cum for me" he looked at her and wrinkled his nose in distaste and disbelief but his hand took the glass and put it to his lips and allowed the warm salty liquid to slip into his mouth and then he swallowed.

As he processed what had just happened she slipped the silicone chastity device over his cock as it softened and clicked the lock closed. "I'll just put this on until you make your decision Tom, if you decide to leave I'll remove it but if you stay it'll stay on until we get you to leave that boy clit of yours alone."

Tom lay on the soft bed totally spent as Jessica put her dress back on an slipped back upstairs to her work. Tom had a lot to think about.

The decision

It wasn't long before Tom slipped into a post coital nap on the soft dungeon bed. His dreams were inevitably erotic and centered on Jessicas obvious control over him and surprisingly his willingness to be controlled.

He woke and enjoyed the drowsy post sleep fugue allowing his mind to wander through his possible choices. Did he want to be controlled? What impact would this have on his life? Would he ever find another quite like Jessica? It all wheeled around in his head. How could he make a long term decision based on only a few days of experience. He weighed the possibilities of continuing versus returning to his home and losing Jessica from his life. Slowly a solution began to form in his mind.

He made his way from the playroom and up the concrete stairs fastening the satin robe to try to maintain some dignity. The bags he had left outside the study remained where he had left them and he could hear Jessica typing on her laptop within. He knocked on the partially open door.

"Come in sweetie." Jessica called. He picked up the bags and came into the study. Jessica sat on a long cream sofa he laptop perched on the old coffee table in front of her. He approached her and knelt beside her placing the bags gently on the couch.

"I take it you've made a decision Tom?" She said looking down at him.

"I have Miss Jessica at least in the short term if that's ok?"

"And what have you decided?"

"I'd like to see where this goes for the rest of my leave and then make a longer term choice at the end of my time off if that is acceptable." Jessica grinned warmly

"Of course sweetie, I'm so pleased you want to stay. I had a feeling when you knelt in front of me that you had decided to stay. So what have you brought me?" She said looking at the two bags.

"The gifts I got you a few weeks back, I forgot to give them to you and I found them in my luggage this morning."

"May I?"

"Of course."

Jessica took the large bag first and dug down through the delicate tissue paper packing that had been used to protect the garments inside. She slipped the retro garter belt from the bag and held it up in front of her. "Tom this is lovely, I adore this type of lingerie" she went back into the bag and found the expensive nylon stockings he had bought as well. "And these are divine, I used to have a pair but I snagged them, my size too. Should I try this on later?"

Tom nodded eagerly. He's been fantasising about how she would look in the sexy outfit.

She opened the other smaller bag and found the lipstick he had bought her. She slipped it from the cardboard box and slipped the glossy plastic lid from it "Armani shade 400, very classy Tom, I love this what a marvellous choice." She opened her phone and found a picture she had captured "you suit it well too as I recall". She said showing him the picture, he blushed but couldn't recall the moment "I bet we could both wear it and make quite the mess."

"Thank you so much for my gifts and deciding to stay with me, now I guess we should decide on the ground rules for both of us." Tom nodded "Do you want me to continue compelling you to do things or would you prefer me to stop and use more 'traditional' methods of domination?"

"I think for now I'd like you to keep doing what you have been doing, those whips and chains are a bit much for me at the moment Miss Jessica."

"Very well, and would you prefer to stay as Tom or would you like Candi to put in an appearance?"

"I don't know Miss Jessica, I'm still coming to terms with the two personas."

"I think having Candi along for now will make it easier for you to accept your place and more willing to try new things. How about we do what we have been doing and let Candi take the strain and bring you back for the highlights?"

"That's sounds sensible I guess, I saw all the makeup but I guess Candi did all the practice as I'm not sure what to do with any of it."

"Very well but we'll have to see about getting you up to speed, i do enjoy challenging your male psyche" Tom blushed deeper still as he thought about the idea of feminising himself for her pleasure.

"So here's what I expect in return. I expect you to be dressed as a woman at all times when you are with me unless you are specifically told otherwise. I expect you to be open to new challenges and to frequent deepening of your hypnotic programming so we can get a full idea of what would happen after the two weeks are over. I expect you to make an effort to be as well turned out as possible every day, full makeup, lingerie and pretty dresses always. When I introduce someone as Miss or Mistress they will be considered my equal and obeyed and worshipped as such. Is this acceptable Tom?"

"Yes Miss Jessica."

"Excellent Tom" She leaned forward and slipped the lipstick he had brought her from its tube. Taking her compact she slipped the tip across her lips painting the rich red colour onto her lips right in front of him, so close he could smell the delicate perfume. His cock began to harden but stained against the silicone sheath she had placed him in. She clipped the compact mirror closed and took his chin in her hand. Their lips met and the slippery red colour transferred to his own lips as she kissed him deeply.

She broke the kiss and admired his lipstick smeared face, "Well its a start for the day," she chuckled "now since you have already enjoyed an orgasm today how about you return the favour?" She lifted the bags to the floor and scooted across the couch so Tom was between her legs. She slipped the hem of her dress up to her waist and revealed her soft thighs and delicate lace g string. She pulled the g-string to one side and guided his head into her warm wet pussy. Tom didn't resist, he slipped his tongue eagerly into her sweet snatch and her moans began to echo though the house as he rewarded her kindness once again.

Training begins

Tom woke late the next morning to a gentle knock on his door. Having enjoyed a restful nights sleep now he knew where he stood, or knelt in his case. Jessica slipped quietly into the room and peeled back the soft duvet off the bed letting the cool morning air play across his body as she slipped into bed beside him. She spooned up to him allowing her warm supple body to make as much contact as possible.

Laying on her side and using her arm to support her head she whispered "good morning sleepy head, are you going to come downstairs soon I have such a fun day planned?" She let her other hand play down his naked body underlining that the fun she had planned very much involved him. His skin broke out in goose bumps at the gentle scratching of her red nails as they explored him.

"I would say 10 more minutes but I get the feeling this isn't optional." he quipped

"Go and get yourself showered and shaved, I'll keep the bed warm."

Tom rolled out of the bed and tried to shake the sleep from his head then got up and went to do as she had requested. He returned to the bed where she lay snuggled in the soft bedding and sat at the edge until she invited him back in. His smooth body slipped easily over the cotton sheets and against her warm satin neglige, his arousal was inevitable but restrained by the silicone sheath she had locked there the previous day.

Jessica recommenced her teasing as she whispered in his ear "We've got lots of experimenting to do today my sweet. You saw all the fun things I have in my basement and I cant wait to show you how they work" to make her point she grabbed his smooth ass, digging her nails in. The whispering combined with the teasing of her nails was doing nothing to reduce his arousal and he strained in his prison even more. "Is there anything you need before I go and get ready?"

"No Miss Jessica I don't think so, I know what is expected of me and I'll do my best to be good."

"What a good boy you are Tom, I think today I'd like you to try to look a little tarty, be creative!" with that she winked, withdrew her hand and slipped out of the bed.

Tom followed her with hungry eyes as she left the room. He stood in the middle of the room, one side a myriad of choices hung from hangers in the closet, on the other a dresser full of lotions and cosmetics he knew nothing about, where was he supposed to start. The door creaked behind him as Jessica poked he head back in. "I almost forgot one vital thing!"

"What Miss Jessica?"

"Pretty sissy Candi" Tom's male persona was banished immediately and Candi sprang forth, he smiled broadly and opened the large closet and clapped delightedly with the range of choices laid out before him "That's my little sissy." she whispered as she slipped back out and down to begin her own preparations to break in her new submissive for real.

Candi heard Miss Jessicas hint in the back of his mind, tarty was just how he liked to be. A deep purple corset dress sprang into view as he rifled through the closet for inspiration. its black lace and purple taffeta skirts pushing most other items out of the way. The rich purple silk of the bodice accented by the ornate black lace gave a Wild West saloon girl vibe. He pulled out the dress and held it up to his naked body in front of the full length mirror, the stiff taffeta rubbing against his thighs as he admired the possibilities.