Jessica and Tom 01: The Hunt

After several minutes the beat had quickened and Tom's strokes were swift, his legs quivered as he fought the urge to cum until he heard the implanted trigger. As soon as it came his cock twitched and ribbons of cum escaped onto his chest and even onto his chin. He sighed as the voice guided him from his trance and told him to clean up. Her own orgasm was close as she fingered herself vigorously, watching him slowly wake and take a tissue to clean up his mess. As he noticed the small amount of cum on his chin, she held her breath, the orgasm broke as she watched him scoop the small Pearl of cum into his mouth and swallow it just as he'd been told.

Morning light spilled through her bedroom through a gap in the curtains, she stretched enjoying the memories of last night's entertainment, both in real life and online. Today would be a reconciliation day, where she trawled Tom's web habits. Hopefully he was sufficiently into hypnosis that she could exploit some existing triggers to quicken her control of him.

After dressing for a slouchy day around the house and having a light breakfast she sat at her desk in the study to review the data the worm had collected over night. Tom was, it seemed, quite the aficionado of female domination porn. As she dug deeper into his internet history his fascination over forced feminisation, sissification, hypnosis, forced cum eating, pegging and even forced bisexuality were all very evident. As she suspected from his reaction to her application of lipstick the previous night he also had a significant fetish for beautifully painted lips. After the hard masculinity of Dylan she relished the idea of training her very own soft sissy boy and making him her personal she-male slut.

Through the day she collated all the hypnosis videos he'd watched more than once. Once she had a list of his favourites she proceeded to listen herself in order to decide which trigger words she might be able to use. 'Sleepy submissive' seemed to percolate to the top of the list as the best all round option to allow her to slip into his subconscious and drop her own unique triggers that only she could use. Problem was if she wasn't completely sure the command was rooted in his subconscious then using such triggers would create questions she'd be hard pushed to answer without giving away her entire plan and in essence ruining the challenge. If she was there in person she could try to rescue such a situation using a rapid induction technique but even that had its risks. No this trigger had legs but they were stage two and she needed stage one in place to use them.

She searched further into his digital identity now looking at the less kinky stuff. Several searches suggested he had trouble sleeping, those queries all seemed to come after his breakup, without a woman at the helm of his life it seemed he didn't cope well with the day to day stresses of life. That presented a possible weakness she could exploit for stage one. She could feign a poor night's sleep encouraging him to admit his own poor sleep and then help him with a technique that helps her when things get too much. Cue a gentle on line meditation session where she can see if he will slip into a trance deep enough to start to manipulate him.

The rest of the day trawling Tom's PC provided few further useful bits of information beyond the type of looks he likes his women to wear; all of which leaned to the glamorous and severe, much like the look she had worn in his first meeting. That worked for her, she enjoyed the power a little powder and paint could bestow on her over a man, if he liked extravagant colours and precise lines then that's what he would get, in moderation of course.

Her phone pinged just after lunch. 'Really enjoyed meeting you last night, hope you had a great time with your friends. Like I said I'm available every night this week so just let me know when if and when you want to see me again. Best wishes Tom' read the message

She needed to make him wait a bit if only to build the desire but she also needed time to formulate her script for his induction so she had a clear plan. 'Busy tonight with work but how about tomorrow around 1900. Will send you the link like before, Jessica xx' she replied.

Slipping into her thrall

At 1855 she once again sent the meeting invite and he straight away accepted it and appeared in the meeting lobby. She could already see him through his webcam having taken control of his PC on the previous meeting. This evening she'd gone for a softer look, silver grey smokey eyes with soft charcoal liner, she added a little dark colour below her eyes to try to give a slightly tired look. A little blush highlighted her cheeks and she complemented it with a soft rose nude lipgloss that shone just right in her study's lighting. She wore a tight blouse emphasising her cleavage, her tight miniskirt remained out of sight from where she sat but maybe it would make an appearance later.

He was sat expectantly, this time a little better turned out even for an online meet up. His blue button down shirt was ironed well, open at the collar revealing a tight white undershirt. He'd shaved too, recently by the look of the slight razor burn under his chin, his dirty blonde hair was also recently clipped back to a short crop, a visit to the barbers this afternoon evidently.

"Hey Tom, you look great, I love the shirt, blue really works for you." she gushed as she joined the meeting. He was grinning from ear to ear before she finished her sentence.

"You too, love the English rose look and who doesn't love a tight top." he replied smirking mischievously, underneath she knew he was squirming wondering if his comment was a bit too far. She squeezed her arms to her sides playfully pushing up her ample bosom towards the camera as she giggled "you are a massive tease young lady!"

They happily chatted for another thirty minutes or so before she began her opening gambit, yawning and stretching her arms above her head.

"Long day?" Tom asked earnestly

"Yeah you could say that, my business never sleeps and that seems to be rubbing off on me! Probably my fault for burning the candle at both ends but I haven't had a solid night's sleep in a while." she yawned again before laying her forehead on the desk in front of the camera.

"I know how that feels." He said exhaling slowly, "since Meghan and I split I'm getting like three or four hours a night then spending another four gazing at the ceiling."

"Seems we have more than just nerdy hobbies in common." Jessica could feel the noose slowly tightening, hoping it would snare her prey. Raising her head from the desk she looked up thoughtfully. "You know back in college I did a psychology minor and we learned a few techniques to deal with insomnia, would you like to see if they help?"

"Well it can't hurt can it?" He quickly replied "I think I'd do almost anything for a descent night's sleep at this point, well almost anything." he chuckled

"Great give me two minutes to find something and I'll be back, maybe you should a have a pee break as if this works you might want to go to bed soon after?" she smiled sweetly then blanked her camera.

'Gotcha' she thought. Quickly finding the audio track she had pre-selected she cued it up in the meeting software then waited for Tom to return.

She opened her camera back up as he sat back down "ok, you all good?" She asked.

"Yes all good, ready for you to work some voodoo magic." he said leaning back in his chair.

"Great, this is just a simple relaxation technique nothing sinister. First we need a bit of mood music..." she began the audio track, a rhythmic sound of waves washing onto a beach followed by the gentle burble of the receding waters across the bed of pebbles.

"Close your eyes Tom and just listen to the waves as they wash up the shore. Imagine yourself lying on the beach, well clear of the tide, dozing on a comfortable lounger in the warm sun." he closed his eyes and she did the same, both of them leaning back in their chairs. "As the wave comes in then take a deep relaxing breath in and as it starts to wash back out then let the breath slowly exhale." The audio track had been modified to allow various tempos and this was set to a normal breathing rate for sleep. "Just stay with the rhythm of the waves breathing innnnnn, annnd ouuuuuut, good, innnnnn annnnd ouuuuut." she repeated the mantra several times over ten minutes hoping to make sure he took to his relaxed state solidly.

She quickly peaked to ensure he was participating, seeing his chest rise and fall with the crashing waves was a very good sign. His head had bobbed back against the headrest of his chair and a serene look had washed across his face "with every inhale imagine all the stresses and trials of your life foaming up at the water's edge then as you exhale they wash away, out to sea leaving you calm and fulfilled. Innnn annnnnd ouuuuut." she continued.

She opened her eyes fully now watching Tom as he succumbed to her spell. His breathing in time to the sound of the waves, his head tilted to one side, his mouth slightly open. Now seemed as good a time as any to try one of the triggers from his collection of hypnosis videos "sleepy submissive." she whispered into her microphone "good sleepy submissive." she saw his eyes twitch slightly as the trigger wafted across his dreamy state, his breathing remained calm and no hint of suspicion was evident.

"Tom my dear, only nod or shake your head, you're far too sleepy to speak, can you hear me Tom?" He slowly nodded. "Good Tom, it feels nice to be my sleepy submissive doesn't it my sweet?" Again he nodded slowly. "Tom I want to take you deeper now, is that ok?" His head indicated another nod.

"Good boy Tom, now imagine yourself at the top of a long stairwell zig zagging its way down into the dark below, each flight of stairs has ten steps and a small landing with a soft leather wingback chair next to a small table. On the table is a card with a number on it. When you get to the bottom of each flight you will sit in the chair and read the number remembering it for the future. As I count from ten to one you'll slowly walk down the stairs towards that lovely inviting chair, with each step you will fall deeper and deeper into trance." he nodded once again

"10, 9, 8, 7, 6, 5, 4, 3, 2,1." She counted slowly. "Good Tom now take a seat in that lovely leather chair and read the number on the card, it should say one, does it?" He nodded with a weak 'mmmhhhmmm.'

"Good boy Tom, this number represents your level of trance and your level of submission to me, as the numbers go up so you become deeper entranced and deeper under my spell. Each time you get to a landing you will remember the number for our next session and start right from that level, no need to go all the way back to the top when you've already come so far." She grinned as a look of satisfaction spread across his face.

"Tom every time you hear me and only me say 'sleepy submissive' you will slip easily into this dreamy state and come straight back to the last sumptuous leather chair you were sat in during our last session and be ready to descend further down."

"As you've been such as good sleepy submissive so far I think it's time we let you back up to the real now. You will only remember a lovely relaxing guided meditation nothing will remain of the stairwell and the chairs in your memory, but your subconscious will remember all those lovely triggers." Tom nodded slowly.

"Good, now when we part company tonight, you'll forget to log off your meeting and just minimise the window leaving the meeting active. Then you'll open one of your porn videos and start to masturbate to it. After you've cum and cleaned yourself up you'll go off to bed free of all your worries, have a wonderful night's sleep and wake up refreshed and ready for the world. Does that sound ok Tom?"

One final nod confirmed he understood his tasks. "You've been such a good sleepy submissive Tom but now it's time to wake up so as I count up from one to five you'll wake up just like you would from a little nap totally refreshed. One, two starting to come up, three just breaking that surface of sleep, four eyes starting to flicker open and five, wide awake."

Tom blinked a few times "wow, I think I must have dozed off, I'm sooo sorry."

"No Tom you just were just very relaxed, surprisingly so. I hope that helps you sleep tonight though." She smiled and looked at her watch. "It's getting late and we both have stuff to do tomorrow so I think we'd best say good night."

"I guess so." he said also checking his watch "nice to talk and thanks for the meditation thing I really think it helped."

"You're very welcome Tom, goodnight sweetie." she blew him a kiss and waited for him to close his connection which she hoped he wouldn't. He didn't he just minimised the window absent mindedly and went straight to the web.

A quick search found him some lipstick lesbian porn. He pulled down his trousers and pants and took off his shirt then sat back and began to pleasure himself. Within a few minutes of watching the two glamorous beauties lick each other to climax he was quivering on the edge of climax himself, evidently waiting for something, then it came one of the girls started to liberally apply scarlet lipstick to her full lips and that was it, his load blew, he grunted as his cum sprayed onto his belly once again.

Jessica sat and watched the show relishing both the superb choice in viewing material and more importantly that he had done exactly as instructed, stage 1 seemed to be a roaring success.

She left the meeting connected just so he would realise he'd done something foolish and she 'may' have seen him rubbing himself off but she made sure her own webcam was coverd and the mic muted.

A day at the office

In the morning she heard the familiar ping of a message. 'Slept great last night whatever that technique was it worked really well, thanks so much, Tom.'

'I bet you did you dirty little boy.' she thought recalling his vigorous efforts watching the two glamorous girls in the video.

'That's great Tom, really pleased for you, nothing beats a good night's sleep, well almost nothing *wink*.'

She pondered how to follow up that little tease then decided to play to his weakness. She took a picture of two lipstick colours and sent it to him, 'which colour do you think for my management meeting 'innocent peony' or 'sinful scarlet'' read the caption.

'Don't know which is most appropriate but for my tastes it's sinful every time, send pictures when you decide! Tom.'

She dressed in her form fitting grey pinstripe suit, its skirt hem respectfully just above the knee, the jacket cut to force the eye towards her cleavage which nestled in a tight white blouse. She placed the camera on its mount next to her dresser and started the video recording. She slowly swept the lustrous red lipstick over each lip then touched up where she had missed. Then she slipped her lips together and blotted them. She stood and pulled the hem or her skirt up making a show of straightening her nude lace topped stockings before blowing a kiss to the camera. She sent the video along with the caption 'sinful just for you'. That should have him rock hard all morning she mused.

A few minutes later his response came through 'forgive me father for I wish to sin.... a lot! Same time tonight? Tom.'

She pondered replying immediately but decided to wait till after lunch to avoid seeming too needy plus it would give him a chance to rewatch her video a few more times and work himself up a bit which all worked in her favour.

Jessica's meeting was, as always a blast, her particular brand of 'specialist clothing' was predominantly fetish wear and lingerie. Her talented and staggeringly deviant designers came up with some very, very naughty designs, all of which needed to be signed off by her before going into production. The bonus to this was there was always a fabulous array of good looking young people parading around her office in the most marvelous creations which either left just enough to the imagination or very little. Rarely did she spend a day in the office without enjoying at least one models carnal delights and today was shaping up to be no different.

The trend back towards more vintage lingerie for women was gathering pace. More women wanted corsets, girdles and garter belts with a modern twist. It fitted Jessica's personal taste as well as she had the body to carry off the 50's pinup look easily and she loved the glamour of it.

The sensational redhead caught her attention immediately as she took to the small catwalk. The striking jade green silk corset with black lace accentuated her voluptuous figure, stainless steel hook and eyes holding the front together while ornate laces hung from the back in a large bow. Garters hung from the corset holding up black lace topped fishnet stockings. Her panties were the crowning glory, the same jade silk, black lace and stainless steel hook and eyes held the front closed, or opened for easy access. Her jade green silk opera gloves completed the glamorous look. Her copper red hair fell in waves across her pale shoulder complemented by her striking green eyes. Her makeup took over from there, heavy jade eyeshadow accentuated her eyes and her full lips were a glossy pink nude.

Having seen all the other outfits and commented on the various changes needed she indicated the model to her office at the end of the large loft space. "I need to check the intricate details of the lace and boning on this one." She dismissed the designers and followed the model marveling at her tight ass framed by the drooping laces from the corset, the black lace g-string panties and the lace of her stocking tops. She guided the model through the door, her hand gently caressing her pert buttocks as she passed then closed the large sliding door behind them. She guided the model to the centre of the large office allowing her to take in all the pieces of bondage furniture spread around the space.

"We like to make sure our outfits stand up to more than everyday use." she said pointing at the various items of furniture including large leather clad Saint Andrew cross. "Are you ok with that?" The model allowed a wry smile to cross her lips. "What's your name my sweet?" asked Jessica.

"Lily, Ma'am." she replied sizing up Jessica wondering who was going to be enjoying whom

Jessica approached Lily circling her slowly, running her finger over the exquisite silk of the corset as she circled the beauty before returning to the front. Jessica allowed her finger to descend to her panties and down her pale thighs. Raising her other hand she slid it up Lily's curving side and then round her ribs to gently cup her ample breast rubbing her nipple through the soft fabric.

She slowly leaned in teasing her lips close to Lily's before allowing them to touch and slipping her tongue into Lily's warm mouth. Lily reciprocated playing her tongue over Jessica's as she slid her own hands down to Jessica's ass, massaging her ass firmly before finding the side zipper to her skirt and allowing it to fall to the ground.

Jessica withdrew from the deep kiss "mmm an eager beaver." she said stepping out of the rumpled skirt and shrugging off her jacket. Lily slowly started to unbutton the tight white blouse as Jessica began to play with her warm pussy through the fabric of her silk and lace panties. Lily gasped as Jessica's finger slipped between the hook and eyes and touched her clit softly.

Jessica sank to her knees in front of Lily, slowly she unfastened the three hook and eyes on her panties revealing a flash of copper hair above a rapidly moistening pussy. She slipped her finger inside slowly allowing Lily's warm fluid to lubricate her finger. She firmly caressed Lily's engorged clit before using her fingers to part her lips and leant in to lick her sweet snatch.