A Sissy in the 22nd Century Pt. 03

The pair of them held a silent staring contest across this argument for a few seconds more. A tension in the air that even Jesse could feel, still buried beneath Miranda and having her anal virginity fought over like the last strawberry on a trifle. But eventually, something had to give.

"Fiiiine..." Huffed the despondent ass-cheek spreader. "We'll make do with sloppy seconds whenever whoever-it-is has deflowered the poor creature. But, you'd best give dear Jesse something now... Pretty, little whores need to know they're loved!"

The buried sissy sighed a little in relief that she wasn't going to be invaded right now... Though the news of this mysterious third party who had placed a booking upon her innocence, was a whole new source of worry and confusion. As was the growing realisation that Miranda had a considerably different idea of what counted as 'love' than most. Just what were these two's intentions for her, both tonight and beyond? Was she now trapped as being just another one of their sordid collection from here on out? Jesse began to feel a little dizzy at how fast her world was progressing into this new shape as a piece of pass-around meat for all these carnivores to squabble and growl over. How easily her own view of herself just slipped into whatever they wished it to be and how little say she had left over anything that happened to her. She was just school property now... there was no way to avoid realising it.

Chapter 10: A Sissy Used Right

Miranda ran her tongue up and down the smooth skin of Jesse's inner thighs. The femboy quailed at such a tickling lubrication across the very edges of her intimacies. Somehow, it felt worse. To have this woman of such unfathomably higher social standing debasing herself to play mother cat around the sissy's most sensitive places. Jesse felt so humiliated by the way her little cock twitched in excitement every time her current owner's hot breath or silky curls brushed across it. Which, of course, just caused the woman to ensure it happened more.

All of this was means to an end though. Miranda was also eyeing up the swollen pillar of her cousin as he stroked it up into its fullest size. Their rented schoolgirl's eyes grew wide as she was allowed a view of the pillar which had threatened to become her rectum's first fleshy invader. Her own half-flaccid little sausage was nothing in comparison. Just another unsubtle statement made by the Algorithm as it shaped the bodies of those on top and those below. She felt herself wilt even further as it approached, as if even her erection was bowing down in submission; a pack animal rolling on its back before its betters.

John picked up the short, slender legs of his evening's effeminate delight. Holding them up by the ankles to provide one long, sheer valley of smooth, silky skin. His partner had provided plenty of lubrication to slide himself between those soft, inviting thighs. The sissy's small, hairless ball-sack provided a neat, little pillow for his cock to rest upon, out the other side. While the feel of her diminutive answer twitching intimidated beneath, was all its own delight. Miranda chuckled evilly to see the direct comparison... He knew exactly how much these moments of anticipatory humiliation turned her on. She loved to watch their playthings squirm with inner turmoil... Pricking out every last burrow of pride they might try to hold onto, as she whispered wicked things to the voices in the back of their minds. Reminding them again and again that they were slutty little whores who wanted nothing in the world more than to be ravaged by her lover's fleshy weapon.

Which is where Jesse found herself. Feeling the teasing caress of that woman's lips against her cheek or the sharp nip of teeth upon her ear. Her slim arms were pinned upwards by Miranda's wiry strength. All while an endless barrage of twisted, debasing encouragements were burrowed into her mind. It became hard to tell which voices were the angel on her shoulder, or the devils in her loins... or this terrifying, naked goddess who played every part at once. John began pumping himself between the gap of her legs. Using that avenue of the femboy's shape he'd made for himself. Jesse could feel each thrust as it slid along her perineum. The flared helmet of that engorged limb catching against her thighs then bumping back over her testicles. The friction it caused as it rubbed up against her own cock reawakened every confused feeling she'd ever had about her own masculinity as compared to those around her. She soon grew back to what length and girth sufficed for her own erection, but the duel of swords where John's weapon collided with hers was no contest at all.

With Miranda's words still crawling in her ear, the sissy could only marvel in the wonder of being used for others' pleasure. She twisted her ankles together in John's strong grip, providing as tight a passage for him to squeeze through as possible. The still-growing width of him squeezing between her flesh sent such ripples of awe and excitement up through her intimacies. She was truly just a manoeuvrable doll for them to arrange and play with however they saw fit... Locked out of her rectum or not.

The joy she got from that thought was sickening and pure. She never wanted this moment to end as she felt her own climax and John's hovering balanced between the strength of his thrusts and the squeeze of her thighs. Auntie Miranda was right, in everything she said. There was nothing left in Jesse to disagree. She loved cock and cum and cunt and clambering over herself to be whatever her current masters wanted her to be. She was in training to be a 1st class sissy slutwife and couldn't even dream of wanting anything else...

Chapter 11: In Aftermath

Jesse woke up from his stupor in a room turned blood red by the setting sun. The tight collar around his neck was singing its buzzing song again, signifying the end of his extended contract with John and Miranda. The naked pair themselves were sprawled over him on either side, dozing gently. A glint of eyes and fingernail idly tracing itself around his nipple told him that at least one was still awake. The prophetic light and heightened senses of reawakening nerves unveiled to him just how many bruise-like hickeys and small indentations of teeth that woman had left all over him. He was an absolute collage of her stamps and brand.

Memories of what had transpired not an hour before came flooding back: The press of John's erection against his own. The feel of it sliding between his thighs, lubricated by Miranda's tongue. The experience of her leaning in to suckle on each of them as their climaxes came closer and closer. His second orgasm of the evening, set off by the very fact that the man who had purchased him was gaining such measurable pleasure from his own unworthy form. The smell on Miranda's breath as she greedily collected those two streams of ejaculate which burst forth one after another, and then the taste of that salty combination as she drooled the mixture into his own gasping mouth.

Jesse had tangled tongues with his glorying mistress for what seemed like an eternity. Awash with a slimy, shared mouthful which was half his own. She had been playing with herself the entire time and finally seemed to reach her own climax in watching her submissive pet gulp down that sordid, slimy mess. It came to light in the sissy's mind that he had struggled to bring the woman to such on his own because her gratification came not simply from her own physicality, but from the overflowing emotional state of those around. The unkempt desires she drew from her own cousin upon their human toys and the embarrassed corruption of those young things themselves.

Jesse could see the parallels with how he himself seemed to find more dark excitement in others gaining pleasure at his expense... than from any direct arousal upon his being. The throb of John's cock between his soft thighs, as he felt the larger man peaking his ascension... Was still stuck in the very depths of the femboy's soul. Already feeling more like some treasured memory, than any small moments of joy in his previous life. It scared him as much as it already made his heart beat at the thought it might happen again. Just who was he becoming, as he already slipped in and out of thinking of himself as one gender or another? Had that wine-guzzling girl with 'slut' scrawled across her forehead. Who had almost begged to be taken up to this cramped, little hotel room... Really been him?

"I-I need to go home..." Jesse mumbled, scrambling himself out from between the two naked bodies and looking around desperately for his clothes.

"Oh... no, honey... Just stay here with us tonight..." Came Miranda's sleepy purr. "We'll pay for anything extra if they need us too... and treat you to breakfast in the morning!"

The sissy was almost drawn in by those glinting eyes in the twilight... but shook himself loose. No! He needed to get out. He needed to escape that teasingly-innocent little whore who still danced around the edges of who he could be, if they wanted. He needed to be him, in his own bed. With Betsy and the Home and everything solid and concrete and grey.

"My roommate will be worried! I've got to go!" He lied, almost certain that Betsy would in fact have tracked exactly where he was, by accessing his collar.

Miranda smiled a feline smile, clearly content to accept excuses... this time. "Well, okay Sweetpea... But we'll message you again next week. There are so many more wonderful places we've got to show you! You get home safe now, alright?"

Jesse nodded absentmindedly, just about managing to squeeze himself back into those ridiculous shorts. Then he was out of the door and away... Already trying to forget the alluring smell of the woman's perfume, and the taste of her incestuous lover's semen...

Chapter 12: Home

The cobbled streets were dark and mostly empty by the time Jesse escaped the hotel. Falsely flickering street lamps mixed in with actual open flames outside many of the still-serving bars and restaurants. Huddled groups and couples lingered in the shadows between these, their entwining forms making it difficult to tell how many limbs were involved in the groping, sighing tangles. It was still easy to tell who was in control though... The sissy saw many wide-eyed reflections of himself peeking out in wonder at the casual opulence of this painted facade. Young, lithe things each being ritually wowed by this place that seemed so far from their own world, yet was probably only two blocks over from the nearest Home. Their older, richer companions all too happy to splash out and spoil and compliment, without making a single dent in their pride or pockets. Only to do it all again with another pretty find the very next day. Jesse wondered how many of his own kind had, in fact, just got very good at faking wide-eyed amazement; in order to keep being brought to such undeniably-lovely places.

He hurried on, well aware that if he stayed too long he would almost certainly be eyed up by some other prospective buyer. Plucked from the street by those who didn't mind claiming a prize secondhand, once those who had first lured it here had got tired. The tightness of that collar around his neck only seemed to increase day by day... As more invisible presences accumulated upon a list of those who could always know where he was. What he was doing. He might have been saved from one unwanted invasion earlier... but the fact that someone, somewhere in this dark city had placed a deposit upon his anal virginity played heavy in his thoughts. Who was it?! Which stranger he had passed in the street had decided to claim him as their own?! There were a few obvious options... but it could be literally anyone who'd seen the sissy in his tight shorts or short skirts. Anyone with enough wealth to throw it around on a whim. Scurrying through this man-made miracle of a resort had seemed so safe to Jesse, in daylight and with John and Miranda on each arm. Admiring all the finely dressed people full of beaming smiles and raucous laughter. But now, alone, he realised he had never been so deeply buried among those who could buy him at a second's thought. These streets were paved with predators... and though he'd smeared off the word upon his forehead, it was really still branded there forever.

The femboy made it to the edge of the black-sanded beach. Tiptoeing along in bare feet past the various, naked serving-staff exhaustedly tidying away the chairs and tables around various food stands. Most of the bars would stay open all night long... but there was little call for ice cream beyond a certain point. The occasional bout of rhythmic moaning rang out as one of these was bent forward by a customer who had been eyeing them up all shift. It was the surest way to earn your tips for the day, after all. Meanwhile the various groups around the mud-fighting pits had now moved on to other pursuits. Bonfires flickered here or there, and the glow of hot coals. Various entertainers danced lightly across these, sending showers of sparks flitting from their heels while spewing out torrents of flame. The magnificent oiled and muscled bodies from before were now being tied up in ropes or wooden frames for various sadistic games of whipping or knotting... Or forced to carry their drunken, stumbling masters around like child-emperors; following their every slurred direction. It was a testament to just how perfect the Algorithm's control was, that even when their owners were nigh-comatose and unlikely to remember anything... Those giants and giantesses fulfilled their duties diligently. If they were content with their lot... What complaint could Jesse have?

He made it to the Maglev station without incident... though his evasive route probably added a good half an hour of anxious walking. As the doors slid shut behind him and the machine slid off toward Home 23, he finally let out a sigh of absolute relief.

End Of Part 3

Thank you for reading! Jesse's story will be continued in part 4. However, if you cannot wait, this tale is being ported over from another site where it is updated serially chapter by chapter. Please see my bio for a link, or wait patiently for longer, more edited chunks.

Methods of supporting my writing can also be found there, should you wish, and I am always delighted to hear constructive criticism from fans... or random vitriol from morons.

Ever so much love, JerkGently

Addendum:

Twinkorp and Lusty Lucy's Fabulous Floozies™ present: Derrick Carter's Rehabilitation Gala, in association with Madame Stanfield's Academy!

A fantastic evening of fun, frolics and fucking... all in aid of supporting a cause that is close to all our hearts.

About the Charity:

Mr Carter's Dropout Rehabilitation program started several years ago, with just one, small facility in the darker fringes of our fair city. Now, however, there are over 30 specialist Homes catering to the specific needs of those most vulnerable in our society. The charity helps those who have lost all hope and purpose in life. Those who have been failed by the systems in place and strayed from the Grand Algorithm's guidance. Any and all gracious support and donations at this event, along with the entire ticket price, will go straight towards this important cause, perhaps even allowing the expansion into further centres to predict and prevent such individuals 'dropping out' in the first place.

Our Generous Hosts:

Entertainment for the evening will be provided by both our corporate sponsors, but also by the freshest class of Madame Stanfield's illustrious Academy. It need not be stated how salivatiously the world awaits any chance to peruse her newest pupils. Though it must be stated that the waiting list for graduates of her fine school has broken its own record once again... so try not to fall in love too quickly! Should you spy a future bride among their number, you may well have to remortgage more than a few other properties for even the down-payment! The madame herself will, of course, be in attendance... if your heart and loins truly cannot be dissuaded.

Programme of the Evening:

5pm:

Doors open. Oral greetings will be provided by all available human property, including the performers who may not be available later.

6pm:

Dinner. To be provided and served on and by Lusty Lucy's Floozies themselves. Where else can you eat a meal right off the body of the chef that cooked it?

7pm:

Dessert. With accompanying seat warming duties performed by Madame Stanfield's students. Please be courteous in sharing the sluts available, and passing them around as and when you've finished with each one.

7:30pm:

A display of acrobatics by Twinkorp's Magnificent Flying Twink Corps™. Watch out for mid-air ejaculations and sprightly, little bottoms landing gracefully into your laps. This is the first return of the award-winning show since their tour of the Russian Federations.

8:30pm:

The Fabulous Floozies return, hopefully having been washed and rinsed from their time as serving platters... to give a display of knives-manship and flaming courage. Expect sharp objects thrown toward naked bodies and the occasional smell of singed pubic hair.

9:30pm:

Dinner will be adjourned and the tables removed as we move on to the charity auction. Item's to be sold include private nights with any or all of the human property on display over the evening, or even, on more permanent terms... The chance to take home one or two of the Floozies or Flying Twinks whose contracts have come to an end. A percentage of proceeds from each sale will, of course, go towards the charity.

11pm till Late:

After the auction has concluded, the dining room will open up once more. Wine will continue to flow and lover's couches and various other soft furnishings will be provided. A live band will play on into the early morning and all human property will be freely available for use, unless specified by any new owners they may now have.

11am the following morning:

This will be the final closure of the venue for cleaning purposes, should any of our guests have elected to stay the night. Black coffee shall of course be available, along with taxi services for those struggling to organise their own transport.

Any human property still being utilised will definitely need to be returned at this point. Madame Stanfield also personally requests that a gentle reminder be given that her pupils remain in education... and as such will still be punished for any lessons they miss due to being held up at such events.

We do hope you have a wonderful evening and cannot stress enough how much your support means to the charity in question and those they work to help. Many thanks to all those involved and all our generous sponsors!

Signed: Derrick Carter and all those at the Dropout Rehabilitation Program