A Sissy in the 22nd Century Pt. 03

She reached out a hand for John to squeeze, the pair of them sharing a meaningful look. It was clear there was a lot more pain and turmoil in that admission than either would state out loud. Things that had pushed them together into such an overtly-close relationship.

"John and I grew up together in a big, empty house... With people who were paid to look after us but kept disappearing; and one grumpy, old parent or another we barely saw... Until we were old enough to go out and start exploring the world on our own. Our only purpose, really, is to exist. So we started collecting pretty things and spoiling them rotten. Seems as good a use of our wealth as any..."

The older women took the opportunity here to tickle Jesse viciously, breaking any of the tension that might otherwise have weighed down upon the table. In the few brief moments the sissy managed to get a thought through that barrage of giggling... She was startled to think that these two who had so much more than her: were still just as trapped by who they had been born to be. There were just layers upon layers of canaries and cages.

It was at that moment, that her collar began rhythmically buzzing. The time in her company they had paid for... had ran out.

Chapter 5: A Question of Usage

Jesse panicked for a moment as the thing began vibrating against her throat, convinced she was about to get a shock... Only to see John calmly looking at his watch.

"Time's up." He said, flatly. Smiling before he started his half-joke: "Here's your chance to run away... if you want to, Jesse."

The sissy looked at him confusedly. Why would she want to run away? These had been some of the nicest hours of her life... She had seen and smelled and tasted things she never could have imagined. Been doted on and complimented at every turn... and barely been molested at all, comparatively... The division between this couple and most rich people she met, had her actually scrabbling for excuses to stay with them.

"B-but I haven't actually... done anything, for you?! You paid for all that time... a-and we've just spent it walking around and eating and things... Wasn't I supposed to-? I'm meant to have asked if you'd like to-?! Oh, I'm mucking it all up!"

The slutwife-in-training was getting herself quite wound up over her imagined failings. A fact that John and Miranda seemed to find cutely amusing until her distress began to draw pity.

"Oh shush-shush, little one!" Said Miranda, taking the femboy's head to her breast. "We get our kicks from watching the faces of precious flowers like you light up, as much as from other things... It is a joy just to watch you walk around with your jaw on the floor and eyes all a-sparkle." She smiled an open and honest smile, to show she really meant this.

"Buuuut... if you did want to spend a little more time with us..."

Jesse was hooked, line and sinker. She almost fell to putty in the older woman's arms and half wanted to crane straight up and kiss those lips.

"I'd love to! I've never met anyone like you two. You're both so beautiful and kind and- I can do anything you want me too! I'm still very new, but they tell me never to say no..."

The words came spilling out from her lips. If one was the cynical type, who knew Jesse had an assignment to fill... You might think that this was a perfect piece of acting. But, all and sundry present knew there was nothing but innocent honesty to the sissy's words.

John and Miranda smiled at each other. There really was something special about this one. Something beyond her natural prettiness and carefully-crafted anxiousness to please. The decision to keep her all evening had been made hours ago, but watching the little creature beg was just another level of delight. They kept so many young pets on their long, long leashes... but this one was special.

"Well then..." The only man here made a few more selections on his holo-watch before clicking 'confirm purchase'. Almost instantly, Jesse's collar ceased its irritating complaint. "Let's go and find somewhere more comfortable, shall we?"

Their young toy gulped down the last of her wine, before jumping up and wrapping her elbows around each of their own. She didn't know where they might be taking her next... but she trusted the pair of them with all of her heart.

Chapter 6: Sun, Sex and Sea-Breezes

The hotel room was small, but bright and cosy. It overlooked a small harbour where various gleaming white leisure boats bobbed up and down. Again, it was hard for Jesse to fathom someone owning a vehicle that could only really drift lazily out around its own fake puddle of artificially-salted water. The ocean horizon looked like it stretched on forever... but it most certainly didn't.

Miranda scooped her up in a passionate kiss almost as soon as the door had closed behind them. The woman was a good few inches taller than the ever-overshadowed sissy, but pulled her rented property up to her by a tight grip upon those tighter shorts. John, meanwhile, was making himself comfortable... discarding various items of technology and ditching his thin, silk jacket. His cousin waited until he had sat himself down on the edge of the bed to take his shoes off... then ambushed him by pushing Jesse's little body over to fall into his lap.

"Love you, darling." She said, switching over to push her tongue into his mouth instead. This caused their teenage companion to be rather trapped between them while they made out for a minute or two. Jesse found herself a face full of Miranda's cleavage to try and breathe through, while behind her little butt was met by a swelling hardness from within John's pants. If nothing else had told her where this evening was now headed... the hot crush of their two, toned bodies confirmed everything she might have asked. The wine was still buzzing through her veins though; and the strange feeling of just being an accessory or conduit to which their passion for each other was flowing through and over... swept her up in the excitement.

It wasn't long before the pair of them were stripping her naked, pulling that ridiculous ensemble of skimpy clothing off one end or the other. Suddenly it felt strange again, for Jesse to be thinking of herself as a young lady, detached from all the world outside this facade of seaside paradise. For there was flopping her same-old, hairless embarrassment of a penis and testicles. Dangling between two milky thighs that might otherwise have been entirely plausibly owned by a natural-born eighteen year-old girl. Miranda cooed and giggled with excitement at the sight of it though. Planting a trail of kisses down from Jesse's cheek, to her flat chest, to her small belly-button...

John was unbuttoning his shirt now, the flaps opening out above Jesse's unravelling hair. He had laid back further in the bed now though, dragging all the action with him. So that the femboy's head was now nestled in his still-covered crotch. As Jesse felt a warm, wet cavity engulf her manhood... she in turn was entranced by a straining tent pressed up against her cheek. Her own, straying fingers couldn't help but wander towards its foothills, as from this angle it seemed to tower upwards like a mountain. Her soft lips parted to let out some of the growing heat and breath inside of her, as strange and wonderful feelings began rising from below. The sun, and a scent of sea-breeze, slid in through swishing net-curtains. Outside the murmur and cries of many joyful voices still drifted ghostily. Jesse reached up... and tugged upon a zipper she found there. She'd never really imagined herself taking the first step in such things. Never imagined she would find herself in quite this place and time. But she yearned to show these two how happy they had made her. Needed to prove she could be a good, little whore... just like everyone told her she had to be. John's flesh spilled out in a tower that reached up to the heavens, and Jesse couldn't help but feel her mouth beginning to water at the sight.

Chapter 7: Swallowed and Shared

Once she had helped the pair of them undress, Jesse simply couldn't pull her eyes away from the bodies of John and Miranda. Evenly tanned and athletic, both of them clearly had a lot more muscle than the small, slim sissy had ever managed to build up. For a brief moment, she held a timid flash of thought at what would happen if she ever tried to resist their bought-and-paid-for advances... Either one could probably quite easily hold her down, while the other took just whatever they wanted. Their very physical forms were a testament to where the power lay. Ageless and unblemished. It occurred to Jesse that, although they looked in their early thirties, these two could have been playing their games for 40 years. Watching as their newest little toys became ever more fragile and delicate.

Yet still, Jesse wanted nothing more than to touch their sun-kissed skin. Earn those charming smiles. More than the wine. More than the assignments she'd been set. She just wanted to make them happy. That was the deep, inner craving that made her heart beat faster and her head displace any remnants of pride or shame there might be, in bowing to their every emasculating whim. There was a warmth like the sun that came along with such subservience... and she wasn't even sure if it sprouted from herself... or the changes the Algorithm had made in her.

Miranda sat on the femboy's face, squeezing in on her ears with those finely-toned thighs. Jesse set to work immediately. She did not know what services the pair had actually paid for. Did not know what else might be expected of her. But a pussy was being pressed down against her young lips... and so she had little choice except to offer a willing tongue up to greet it.

"That's it, little sweetpea." Sighed the older woman, clearly having been waiting for this moment for quite some time. "Give Auntie Miranda what she needs..."

Meanwhile, John had taken over ownership of Jesse's meagre erection. The sissy gasped when she felt a second mouth wrap itself around her small cock. She had never had a true-to-form man encompass her so. She could feel the scratch of smartly unshaven stubble where his chin bumped up against her hairless testicles. It sent shivers of excitement running all the way through her, to the point where Miranda could clearly feel them.

"Ooooh, I think she likes that Darling... Isn't her tiny thing just the tastiest little morsel!"

Jesse couldn't see anything but the olive rosiness of her current mistress's flesh. Could barely hear through the muffling tightness of those clenching thighs. Her entire world was the overwhelming sensations coming up from below, and the sour sweetness of Miranda's juices. She could already feel herself teetering on the edge of an explosion, having been built up over the entire afternoon by the constricting exposure of her slutty clothing and this beautiful woman's ever-wandering hands. She wanted to give back as much of that swelling pleasure as she could, driving her tongue upwards into the gushing entry above. Miranda gasped with the increasing intensity of her plaything's efforts, but it was that human toy which broke first.

Jesse nearly choked as she bucked her slim hips against the mouth bearing down on them. Shooting string after string of viscous whiteness into John's waiting mouth. She moaned her climactic amazement up directly into the passages of his cousin and lover, unable to breathe for the entire time her body was convulsing with ejaculation.

As she collapsed back down onto the hotel bed, and finally managed to find an air hole past that suffocating genitalia... The sissy heard her temporary owners sharing a passionate kiss. Her mind was filled with the image of her own slimy expulsions, being passed back and forth between those greedily entwining tongues. A blush might have blossomed upon her cheeks, had she not already been bright red with exertion.

But, there was still a vulva to be lapped at. So while her most intimate flavours were discussed far above... Jesse set back to her duties with the diligence that one might expect; from a student of Madame Stanfield's prestigious academy.

Chapter 8: An Ass that Asks its Worth

Jesse was still struggling to get Miranda to cum, a fact that was beginning to upset the diligent cunnilinguist. Her tongue was getting tired, and the hot confines of the woman's thighs were beginning to make her lightheaded. Yet, every inch of her soul told her that she couldn't stop until the job was done. That was what she was for, wasn't it? That was what the Algorithm had picked out to be the sole purpose to her existence: To be a face that others sat upon... If she couldn't even bring them to climax, then what else did she have left? Surely the tight collar around her neck would register such failure... Surely even this kind pair, who had paid so much for her time, would demand a refund?

The panicking sissy could already imagine the glowering stare of Mrs Durren when her homework assignment came back empty. The humiliation and punishments that would await. Perhaps she would be thrown out of the school altogether? Left to roam the streets at the mercy of any and all the Dropouts who found her... without the fear of Corpo retaliation to keep them back.

Miranda herself was seemingly not aware of any of these spiralling thoughts tearing through her human seat. Though, she was enjoying the sudden second flurry of that energetic, young tongue. The heiress delighted in keeping their various toys locked between her legs for as long as possible. It made her feel motherly, like a nesting hen. Keeping her precious little eggs warm while they spoke volumes about how much they loved her, up into those lower lips. It took more than that to truly excite her these days though, and the taste of this delightful thing's spunk upon her lips was dragging up her lust to see such innocence ravished. She leaned forwards across Jesse's stomach and pulled the teen's knees up and out. Presenting the little star that lay there in a way she knew would drive her dear cousin mad.

"Come now, Darling... let's not keep our new friend waiting any longer." She lowered her head down further, until she could rest her chin upon Jesse's little ballsack and gently spread the femboy's cheeks apart with needle-nailed fingertips. "Just look how the little cutie is winking at you... She can hardly wait!"

John was indeed entranced by the small, puckered sphincter being displayed for him by his ever-devious partner in crime. How many pretty little miracles had she laid open before him and invited him towards with that wicked little grin now? Too many to count... Yet every time his swelling erection twitched at the prospect. It had been her who had started them on this path of hunting down only the youngest, sweetest prey. Her who had perfected the art of luring them in and breaking down their barriers one by one, until the wonderful playthings were just putty in their palms. Her that had saved him from the terrible, undermining drudgery of life as a bottom-line signature... and her that he needed to see smiling back at him every time he filled another young pussy or ass with semen. He loved Miranda deeply and knew she felt the same. The ever-changing toys they used to surrogate those affections were simply a part of that love... for a time.

The man plucked his holowatch from the bedside counter where he had left it. They had only paid for Oral while at the restaurant with Jesse. Father's stern voice ever in the back of John's mind, growling about extra expenditures that they never actually got around to using. There was no way he could turn down the pretty, little whore now though. Miranda was right... that perfect, rosy ass just demanded to be invaded. How the poor thing could make it five yards down any street without being bent over by someone was a great mystery. John had spotted at least twenty interested parties looking up her collar details just as they'd walked around town. It was lucky they'd got to her first... John was certain this was going to be a slut with a month-long waiting list, come this time next year. The Stanfield family didn't make their fortunes from nothing. As one born into near unlimited wealth looked over the price list of his latest rented property once again... He wondered if she had any idea how much she and her classmates made that school, each and every day.

Chapter 9: Things Already Reserved

"Oh!" Said John, his voice clearly tinged with surprise and a little disappointment. He was still scrolling through Jesse's page on the school network, various images of the earlier dress-up session trying to leap out and grab his attention.

"What's the matter?" Asked Miranda, still perched between the sissy's open legs, leaning her elbows down upon them to spread them further. She was idly tracing a finger around the toy in their toy's rectum, sending all sorts of strange emotions hurtling through Jesse. Neither of them had even commented on the lurid pink buttplug still anchored there... Why would such a slut not be wearing one?

Her partner smiled sadly. "It seems our new find is even more precious than we thought... she's a virgin, at least down there. But someone else has just put a large bid down on claiming that... They must have been watching how far we were getting."

Miranda's face screwed up into a vision of disgruntled scorn. The harshest expression she'd yet worn in Jesse's presence... not that the femboy could see it.

"Well, just outbid them back! We can't leave this poor thing waiting! Look how much she needs your cock!"

The woman dug her nails into the sissy's soft rump. A sharp, clawing massage that served to express and divert her frustration. Even in the pinching pain of it... Jesse found herself aroused and encouraged. She wasn't anywhere near as sure she wanted John to shove his way inside. But every time her current masters spoke of it, her beating heart seemed to lean in that direction. It was as if the more they spoke over and about her body as their own, personal property... The more it became so. As anxious to meet their whims and wants as the teenage boy who'd previously thought he both owned and inhabited it.

"We can't..." Answered John, clearly aware he was going to have a fight on his hands with this denial. "We're already nearly over budget for the week... and we promised we'd take little Jane skiing on Thursday..."

Stormclouds crossed his cousin's brow, as they only can upon those not used to ever being told 'no'.

"Screw Uncle Benji's 'spending limits'! We've got more money than Jesus, Buddha and Santa Claus! What does he expect us to learn from holding back a few more drops from the ocean?!"

This was a battle that had been ongoing for several weeks now... With poor John trapped as the middleman between his stern father and ferocious, familial lover. Unfortunately for him, while his heart was decidedly sided one way... his head could see some sense in the other. He was always mildly worried about what would happen if he ever did have to take over the family business.

"He says it's to learn quality over quantity... by making us choose which of our little flowers are really worth the investment. It's asset management... just the same as knowing which employees or products can be cut from the company when needed..."