Jessica and Tom 02: Meeting Up

Part 2 of my story, hope you enjoy it. this part is far more visceral and covers many more kinks.

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In the real

Tom had finished his client meeting very quickly, it was a courtesy that wasn't even needed but it had provided a convenient excuse to go to see Jessica and a way to claim the expenses for his leave. He arrived at the hotel a little after two pm and having tucked his car into the hotel parking lot had managed to swing an early checkin for his room. The room was the usual hotel fair, clean and tidy, trying to be trendy without spending too much money. He lay on the bed wondering how he was going to while away four hours before he finally met the lovely Jessica.

'Just arrived, meeting took far less time than I thought, looking forward to tonight like you wouldn't believe, Tom'

'Me too Tom, just seeing Sarah, getting my hair and makeup done especially for you, its going to knock your socks off!'

That didn't help his anticipation of the evening, now he was nervous and horny and as a result of the latter becoming more and more uncomfortable. He opened his bag and dug out the neatly wrapped gift box containing the lingerie and lipstick he had bought Jessica some weeks ago. He didn't notice the smooth large wooden box that he'd carted in the other side of his luggage despite its size and weight.

He opened his laptop and waded through the myriad of soul sucking e-mails that had come in while he had driven to the city and also during his meeting. At least these would give some distraction. His work took a good two hours, most of it spent telling his team how to do their jobs while he was away. Finally at half past four he thought he may as well get ready and maybe get a coffee before they met.

He wore a pair of cream linen trousers and a blue button down shirt as he exited the hotel lobby, his jacket over his shoulder as he walked purposely into the city. First order of business was to find the restaurant. He pulled up google maps and entered the restaurant name, it seemed to be around five hundred metres across the park so he headed off in that direction, his new leather soled shoes scraping on the pavement as he walked.

Once he'd found the restaurant and verified there was a six o'clock booking for Jessica he asked if there was a coffee shop they could recommend. The maitre'd directed him to an independent shop a few hundred metres further on which, he said, did fabulous coffee. 'Good enough for me' he thought.

By five thirty he'd nursed his latte about as much as he could and decided to take a walk around the park before heading to the restaurant. The evening was warm but not oppressive and his watch kept bitching at him for not doing enough exercise, so here was a good opportunity. He arrived at the restaurant at ten to six and was shown to the table by the same maitre'd he'd spoken to earlier. He ordered a glass of white wine and settled into the slightly uncomfortable but very trendy chair.

Six o'clock came and went and by six fifteen he was checking his messages to make sure he hadn't made an error on the time, or worse the date. No messages from Jessica either which put him on edge. Finally his phone pinged, 'sorry I'm late, traffic is heavy, be there in 10, I'm worth the wait though I promise, Jessica xx'. He exhaled deeply, he'd started to wonder if she was going to stand him up which, with his recent luck wasn't outside the realms of possibility.

He heard the slam of a car door and saw through the smoked windows a Mercedes limo pull up outside, he couldn't get a good view as the passenger had got out right in front of the maitre'd's lectern. A subtle clicking of heels on the expensive marble floor announced her arrival. Taking her arm in his, the Maitre'd guided the woman towards Tom, his jaw dropped.

Jessica's glossy raven hair hung in loose ringlets over one shoulder, her green eyes were surrounded by dark, smokey eye shadow with a hint of glittering royal blue, her lips were a deep velvety matte crimson. Her black dress stuck to her like liquid, its plunging neckline accentuating her cleavage. The tight figure hugging material traced her hourglass figure over her hips and cascaded straight down to the floor, a generous slit came all the way up to her upper thigh allowing her full stride, was that a hint of lace a the top of her leg? Her red soled black Christian Louboutin heels tilted her arches to accentuate her shapely toned legs as she glided elegantly across the floor.

She smiled at Tom and reached in to hug him, they air kissed, only polite on a first meeting he thought. 'I'm so pleased to finally meet you Tom, I hope I'm worth the wait?"

Tom didn't know where to look to be polite or what to say, he fidgeted nervously "I er.... You look stunning, I literally don't know what to say." as she retreated from the polite hug she gently pecked a kiss on his quivering lips

"You're too kind Tom." she said as she placed her glittering clutch bag on the table and sat.

"It's so good to finally meet you Tom, I can't believe its taken so long to get this arranged. Things are so hectic these days." She ran her fingers through her black mane, allowing it to hang seductively over one eye.

The waiter arrived with the menus and wine lists. The conversation began over which wine they should have. None was less than $100 a bottle but this was his chance to make a good impression and 4 months of saving meant he could push the boat out. A suitably pleasant Sauvignon was decided upon and the waiter retreated to leave the couple to their conversation and to decide on their meals.

Tom found himself drawn to Jessica's eyes as their deep green colour sparkled in the candlelight from the table. He slowly felt the trembles ease from his legs as they engaged in the usual dating small talk. How had his trip been to get here? What was his hotel like? And so on. All the while the candlelight drew his attention to her eyes and he slowly but surely became more and more enchanted.

The conversation was easy and light hearted and Tom felt as if they had been friends for years, she laughed at his jokes and anecdotes and he enquired into the so far mysterious details of her life, what she did? where she was from and the like.

After each course she had retrieved a shiny lipstick from her clutch bag and reapplied her crimson lipstick. Tom couldn't help but gawp as she painted the colour onto her lips each time. The conversation stalling as he stared. By the end of desert he thought he saw a hint of a smirk as she repeated the process once again.

The wine had done its job and they both felt nicely buzzed. With appetites sated Tom asked for the bill and asked what her plans for the rest of the night were, desperately hoping they included him. She smiled "I know a place just around the corner with a nice atmosphere, its quite close which is good considering these shoes." She rubber her leg against his as she lifted her foot up to show off the patent leather heels she wore.

The touch was electric and raced straight to his groin, he became acutely aware of his rapidly hardening cock as he grinned, looking at the smooth leg as it flashed in the slit of the dress revealing the hint of lace at the top of her leg. He gulped.

The bill paid, they joined arms and she led the way out of the restaurant and to the winebar a few hundred metres down the road. The dim lighting and modern decor oozed sophistication, the young and beautiful gathered all around the bar enjoying one of the coolest spots in town. The piano was delicately playing in the background adding to the mood of the place.

The barman caught their entry and smiled at Jessica, "Your usual table miss Jessica?" She nodded and made a beeline to the back of the bar. The barman followed soon after with a bottle of champagne and two fluted glasses.

"Don't worry Tom, like I said tonight is on me, its the least I can do since you travelled to meet up." The booth was cozy with gauze drapes making it private and intimate while still allowing you to people watch. They settled into the sumptuous leather couch, Tom adjusting himself awkwardly, his arousal causing him the now usual discomfort within his plastic prison.

She allowed the waiter to pour the wine and raised her glass as the froth evaporated in tiny bubbles. "To finally meeting." She said and clinked glasses, "I'm so looking forward to eating you up." A predatory glint in her eyes as she locked eyes with Tom and he felt the full force of her gaze.

She gently slid her hand down Tom's' thigh, sensing the quiver of his leg at her touch, knowing he was about to fall under her spell. Hormones raged within him, mixed with a little alcohol and a lot of subliminal conditioning, her time was at hand.

"Tom, how do you feel?" she said, looking deep into his eyes.

"A little tipsy but remarkably happy."

"I'm pleased you're happy Tom."

"How can I be anything else with you sat next to me in that dress."

"I'll give you that Tom, it is a fabulous dress, wait till you see what's underneath!" she knew that comment would have him straining in the cage she had enforced on him. She slipped her hand under the table and into his groin. She sensed the chastity cage over his cock as she allowed her hand to slide down his inner thigh, he gasped at first before allowing a soft moan to escape. She took his hand and placed it into her lap just inside the slit of her gown, his fingers instinctively found her delicate sheer lace panties which were hot and damp. She guided the hand further down her leg till he felt the soft lace of her stocking tops.

"I think its time we made an exit, what do you think Tom?" He nodded eagerly. She motioned for the bill and the well built barman arrived promptly with it on a small silver tray. She signed it and thanked him. "My driver is outside so no need for a taxi." They vacated the booth and she strode ahead guiding Tom by the hand through the growing crowd. He couldn't do anything but follow the statuesque beauty before him, her thick floral scent intoxicating every inch of him.

The driver opened the rear door and Jessica got in and Tom followed. The soft black leather seats had the desired effect. Tom slipped into a dreamy haze as soon as his seat belt was fastened, she replaced his hand in the split of her gown and his fingers lay on her warm wet mound rubbing her sex as the bumps in the road jostled them.

'Shake a leg Tom." his eyes blinked open as the car slid to a halt in front of the tall 4 story townhouse. He had no idea how he got here. He quickly retracted his hand from her groin, not the gentlemanly thing to do on a first date he thought to himself, must be the wine.

They climbed the steps and Jessica opened the large glossy black door inviting him into the house. Her heels clipped on the solid wood floor as she guided him into the kitchen and opened the fridge to get a cold bottle of wine. "Take a seat Tom." He sat awkwardly on a tall bar stool at the counter as she poured a glass of white wine for each of them into expensive fine crystal glasses before she joined him on another bar stool, her dress open provocatively and showing the ornate lace top of her stocking. Tom didn't know where to look, her glorious crimson lips, her heaving cleavage or her smooth inviting legs, his mind quickly becoming over loaded.

She reached forward and gently kissed him, slipping her tongue into his mouth and toying with his tongue. She felt her creamy matte lipstick smear slightly and as intended as she deepened the kiss. She retreated from his mouth and gently rubbed at his now lipstick covered lips. "Would you like to taste me Tom?"

"Yes very much."

"Good boy." She splayed her legs allowing the gown to slip to one side revealing her damp panties and vintage garter belt and thick garter straps. "On your knees sweetie." He didn't need any more encouragement, he slipped off the stool and straight to his knees. She slid the panties to one side revealing her smooth wet pussy. She guided his head into position and she felt his now slick lips slide onto her mound. His tongue slipped into her pussy lips and she moaned as it hit her clit. She held his head in place as he slipped his tongue deeper into her, alternating between plunging deep into her warm wet slit and flicking across her slippery clit. She leant back an elbow on the counter the other keeping his head in just the right place and allowed her hips to find his rhythm.

Feeling her climax build she needed to make a decision, gorge yourself in repeated orgasms the whole night or restrain yourself now and escalate the experience upstairs.... Decisions decisions, but she so wanted to see how far she could push him tonight. She eased her hand from the back of his head and allowed him to come up for air. "You seem to be a well practiced pussy licker Tom but I have more fun in mind." She sighed as her climax receded. "Be a good obedient submissive and go upstairs, the bedroom door is open. Go in and get undressed then go to the bathroom and follow the instructions on the hair removal cream I've left there for you then have a nice warm shower. Once you're done in the shower I want you to go and kneel on the rug in the middle of the room and wait for me."

Tom stood and went to turn but she grabbed the front of his shirt pulling him close to her then leant forward passionately kissing him. She could taste her own juices on his lips, she toyed with his tongue a little while longer before releasing him, "Off you go sweetie." slapping his ass as he walked away.

Tom climbed the stairs and saw the open door on the landing. The room was softly lit with old filament light bulbs, dark grey satin drapes hung from the ornate four poster bed gently reflecting the light. In one corner a large oak dresser with a padded bench seat and large studio style mirror sat. Opposite the old sash windows was a large set of oak closets. He took off his shirt and undershirt and folded it neatly placing it on the padded seat. It did feel odd to just go upstairs and get naked on a first date but he felt it was the right thing to do. He slid his trousers off and folded them neatly and placed them on the same pile before slipping off his boxers and socks.

Completely naked he went into the stylish modern bathroom. He saw a pump top bottle with a note telling him what to do and a small old fashioned hour glass. He rubbed the thick cream onto his entire body, turned the hourglass as instructed and waited for the sands to run through before jumping in the shower and washing it all off thoroughly. He took a fluffy white towel from the rail and toweled himself off, which felt odd to his now smooth hairless body, before going back into the bedroom and kneeling on the soft Persian rug at the bottom of the bed. His cock began to stir as he heard the clip of high heels coming up the stairs.

Jessica had heard the shower turn off and quickly touched up her makeup and freshened her crimson lips with her lipstick, she kicked off her panties and made her way upstairs. As she entered the room she was delighted to see Tom obediently kneeling on the silk rug, she smiled broadly her white teeth shining between her deep crimson lips. "What a good boy you are Tom, as you were".

He blinked a moment and looked around unsure how he got here, why was he kneeling in her bedroom. She looked down at him reveling in his confusion. Slipping a hand behind her she unzipped the slinky gown and shrugged the shoulders away allowing it to crumple to the floor. She stepped out of the halo of material in a black and blood red satin corset, her lace topped stocking held in perfect position with 8 thick garter straps.

"You remember the picture you sent me Tom?" She turned and opened one of the closet doors and bent down provocatively allowing her garters to accentuate her perfect buttocks as she found what she wanted

"Yes of course."

The metal parts of her chosen accessories clinked as she withdrew from the closet standing upright. In one had she held a leather collar and stainless steel chain leash, in the other a leather strap-on harness with a small but realistic dildo hanging from it. She walked across and stood in front of him, bending down she kissed him tenderly as she slipped the collar around his neck. Standing upright again holding the leash in one hand while the harness dangled from one finger of her other hand. She grinned as his cock strained in its plastic prison, his eyes full of desire as he saw where he now stood in the equation.

"Come and sit at the dresser Tom, it's time to get you ready for the rest of the evening". He stood and walked to the dresser, sitting his naked body in front of the mirror. She flicked a switch and the dazzling bulbs around the mirror shed an even light over them both. She stood behind him, the steel clasp of her corset brushing the back of his head then leant down and placed her head on his shoulder and whispered into his ear.

"Do you know what a sissy is Tom?"

"No I don't think so."

"I think you're lying to me Tom, I think you know exactly what a sissy is, I think it's something that gets you all hot and bothered inside. You see Tom I already know most of your dirty little secrets, you told me most of them yourself but you wouldn't remember that"

"I don't understand." he said nervously.

"Let me demonstrate Tom, sleepy submissive." his shoulders slumped and his eyes slammed shut so powerful was the trigger now.

"Tom I think from now on you should always address me as either Mistress or Miss Jessica do you agree?" He nodded his agreement

"Now we need to add another few triggers to best manage your submission and subjugation. When I say 'pretty sissy Candi' you will slip into being an obedient adoring sissy, in love with all things girly and willing to try anything if it pleases your mistress. On the other hand if I say 'manly man' you will revert to your original reserved and masculine Tom persona and react accordingly to your situation. You will still remain submissive and obedient but you will be very aware of your subjugation and my control over you. Do you understand Tom?" He nodded slowly

"Good boy, finally if I say 'back to the real world' you'll come completely back to being normal Tom. You'll forget all the wonderful things we've done together. You'll be very happy and be aware we have a healthy loving relationship."

"In a moment I'm going to wake you up and you'll use the makeup on this dresser and put on your 'going out' look just like Sarah taught you and that you've been practicing so hard these last few weeks. Once you are done you'll slip back into this lovely sleepy state." snap went her fingers.

Tom's eyes flickered open and straight away he began moisturising his face and finding the various bits of makeup and brushes he needed. Jessica picked up her phone a began videoing his transformation. He applied a near perfect foundation before concentrating on his eyes making sure he got the smokey effect he had practiced just right. He contoured his face and finished off with the cherry red lipstick she handed him, lighter than he had practiced with but appropriate for what was coming next. He slipped the lipstick back into its lid and after placing it on the dresser fell back into his slumber.

"Manly man" she whispered. His eyes once again flickered open. In his mind only moments had passed, the blink of an eye and yet gazing back at him was a perfectly made-up face with red full lips.

"How, what, I.... What's happening"

"Oh Tom, I'm being a bit mean, I've been toying with you for quite a while now. To be blunt you've been hypnotised. I can't make you do anything you don't want to do but I can suggest it's ok for you to explore your deeper desires in a more public manner. We've had many open chats about your fetishes and being made into a sissy was one of my favourites so here we are"