A Sissy in the 22nd Century Pt. 01

His mind trawled back through his very limited sexual experiences up to this point, desperate for something else to focus on... but unable to detach from the avenue down which his worries escalated. Sharing a room with Betsy had meant his opportunities for... exploration had been limited. Sure, he could wait for her to fall asleep and then load up the glitchy, old flexitab that they shared... But the fear of her waking up, and then the couple of embarrassing times it had actually happened, made such forays a fretful and hurried affair. When she had caught him the third time... and then just wordlessly clambered into bed next to him... It had been the most wonderful and horrifying night of his life.

From then on, there had been an unspoken agreement that, at least one night a week: They would sit side by side half-naked and watch whatever colliding naked figures they could find on that small and flickering screen. Of course, he had let her do most of the selecting... More content to simply feel the moving muscles in her arm against his shoulder than to care much what others got up to. From there things had just escalated... all the way up to the adventures of the night before. As in all things, Jesse had just gone with the flow... Hoping to keep a smile upon the faces of those he cared for.

An icy visitor was knocking upon his rear door. He could feel a drip of the viscous fluid it was drenched in, trickle off down his perineum. A steady, consistent pressure began to force itself inside of him. He felt things stretching. Widening. Sending panicked signals up toward his brain as to what exactly was happening here.

"Just relax..." Said that soft voice, floating in the air above and behind him. The same voice which was pushing this invader further into what had only ever been an exit till now.

Yet, it did help him relax a little... Jesse was not unaware that he had always just found it easier to do as he was told. Whether that made him a '1st Class Sissy Slutwife' or not... he wasn't certain. But it did mean he wasn't going to buckle or run away when someone was just, very gently, sliding something into his rectum. Once it was what felt like halfway in, the going became easier. The senior carefully rocked the thing forward and back, getting it just a little bit deeper every time. Jesse found he had a strangely intense ball of sensitivity, somewhere around there... Which sent deep shivers of dark emotion through every pit of his being every time it was pressed upon. He shuddered a little to feel his small cock rising again as these sensations shook through him, but hardly felt it was the most embarrassing thing happening right now.

At last he felt himself closing up around a new weight he was entirely encasing. He could feel the cold lump of it pressing against the depths of him, and his legs shook as he stood back up and felt the chain attached to it tickle against his ass-cheeks.

"Good girl!" Announced that soft voice, full of genuine pride. Jesse turned to look over his shoulder at the beautiful face above... and was rewarded with a quick press of lips to his forehead. The soothing sense of their presence seeming to linger there for a long while afterwards. Waking up to the rest of the universe a little more, he heard a few light snickers from those around him. The girl to his right offered a warm, little wink... chained as they now were to each other by the same unorthodox circumstances. Looking around further, Jesse realised he had taken considerably longer than anyone else to envelop the metal plug... and the other seniors were already moving steadily down the lines, eliciting gasps and groans and squelches wherever they went.

Chapter 17: A Taste of Cooperation

Once all was said and done... there were five groups of four students all bound together by the metal plugs shoved securely into their rears. Jesse shuffled awkwardly with the feel of the thing resting inside of him, constantly convinced it was about to fall out. This resulted in him standing upright with his thighs clenched together, ankles turned out as if he desperately needed the bathroom. A glance around revealed several others giving off similar signals, picking out those that were not used to such treatment.

The seniors had returned to stand beside Ms Julian at the bottom of the staircase, each returning to their individual aspect of loveliness without a hair out of place. The teacher herself stepped forward once more to offer one last instruction.

"Excellent! Well now that is out of the way... In a moment we will lead you upstairs to your classroom where one of my colleagues will begin the first of your actual lessons at this school. However, it is important that you always remember to thank those who help you with your education in any way. Be that by guiding you, teaching you or punishing you... Therefore the first group task for each team of four of you, will be to bring one of us to climax orally. You will get down on your knees, and begin immediately."

As one, the class descended... though there was some degree of anxious shuffling as those still unused to high-heels or butt-plugs worked out the practicalities of those extra complications. There seemed to be no particular assignment as to which group serviced who... so Jesse caught a smile from the tall, thin senior and hoped that she might reach them first. It was not to be, however... The one that he had now internally labelled as 'The Menace in Frills' made a beeline for his group. She paid little attention to him, but the teen realised the pupil on the far end of his chain was the other underwear-offendee... who the Menace had practically ripped free of her fancy lingerie. This was definitely some sort of power play.

She said nothing when she arrived though. Simply standing over them as they worked out the mechanics of shuffling forward on their knees while still tangled together by quite short chains. Inevitably, the tent-like nature of her thousand, hooped skirts meant they all had to crawl inside to find a hot and enclosed space surrounding her smooth and dainty legs. What was not so expected, was the absolutely humongous cock and balls that lay drooping inside there. Jesse had never dreamed one could grow so big... especially on a young lady who couldn't be much taller than him. The two who were in the centre of his chain-gang set to work on it at once... clearly more than a little practised at the art of spreading saliva over a shaft of waiting flesh.

Which left him face to face with the lingerie-less daddy's girl, who still looked a little red-eyed and teary from that whole exchange. She was big-eyed and pretty... wearing a lot more makeup than he was and with her shoulder-length, blonde hair tied up in cutesy, little pigtails.

"Come on then!" She half-barked, half whispered to him. "Let's get this over with quickly..."

But Jesse didn't quite know what to do to help... there wasn't enough room for him to squeeze in around the front and get access to that swelling penis. He supposed he could slip between her legs and do something with her testicles...?

"Oh, for heaven's sake-" Huffed his partner. "Like this!"

She then promptly stretched herself up and spread their hostess's ass-cheeks, burying her nose between them. Jesse watched in amazement as she jammed her tongue into the puckered star she found there and worked away with diligent seriousness. With a start, he jumped forward to help... the two of them taking it in turns and switching to sucking at the back of the senior's balls in between. It wasn't long before some muffled squawking from the other side of the equation told them their task had been completed... and someone had earned a large, salty mouthful for the trouble.

Chapter 18: A Question of Etiquette

"The correct greeting for a Slutwife to offer anyone they meet is 'Hello Sir or Ma'am, how may I service you?'. This should always be said in a bright and cheerful tone, not sullied with sarcasm or impatience... Even if you are in a rush to be somewhere."

The grey-bearded man who was speaking was NOT who Jesse had expected to be leading their first lesson in 'Slutwife etiquette'. Well dressed, but drily spoken. He seemed more like your average history teacher, or possibly the butler to a high class residence... than someone who would unveil the polite and correct order to suck several cocks at once in a gang-bang situation.

"If uncertain as to the person's preferred gender pronouns, you may offer both... However, should this cause offence, you should expect and accept any just punishment they might choose to dish out."

The teen shuffled uncomfortably in the seat of his old-fashioned, wooden desk. Sitting on top of the metal plug that was currently buried deep inside him added a whole extra level to its presence. The desks were also spaced out at almost exactly the furthest possible extension that the chain connecting him to the three other members of his group could reach. This meant that any slight movement by any of them could cause a rippling chain reaction of red faces and caught breaths. Jesse was worried that his wriggling inexperience in carrying such a burden, was causing more of these than anyone else.

"A Slutwife never refuses anyone who replies positively to that invitation... If she is in a rush to run an errand for her current master, then she must simply endeavour to service this secondary party as quickly as possible. Try to ensure any fluids produced are deposited internally, so as to keep yourself pristine... and make no mention of the event when you do manage to return. Should your master choose to punish you for tardiness caused in this fashion, that is his or her right; and obviously you should accept the lesson gratefully."

The sticky summer heat of the classroom was really starting to get to Jesse, combined with the multiple alien layers of discomfort and humiliation here. He was painfully aware that the front flap of his tartan skirt had been tented out by at least a half-mast erection for the entire time he'd been sat here. The rough grain of the seat against his bare backside. The ever shifting lump pressing up toward his stomach. The ridiculously skimpy outfit worn by him and all the other beautiful strangers around him, and this endlessly rolled out list of rules. All of which just seemed to lead to you being punished for things beyond your control... It all added up to make his head swim and heart thump up around his ears.

"However, should you be accosted by a whole group of lower class parties... I would advise you gather as much evidence upon yourself as possible, to prove to your master that a greater delay was unavoidable. Torn clothing and bodily stains are not necessarily badges of shame for a young Slutwife, after all... but also signs of her worth as seen by society at large. In fact, some masters may see fit to punish you if you don't look something of a state by the end of the day. Avoiding your duties being a very serious malefaction that should never even be put forward as a possibility."

It was all getting too much for Jesse. He had to get out for some fresh air. The butt-plug was pushing up against his bladder and making him desperate for a piss, but the constant sense of arousal jarred heavily against that need. Eventually, there was little choice but to jam his hand up in the air...

"Sir, I'm sorry- but may I go to the bathroom!"

The old teacher was clearly sympathetic when he saw the desperation on the teens face... but seemed incapable of doing anything quickly.

"Hmmm... well I should warn you that, under normal circumstances, you would just be instructed to relieve yourself in your chair... and clean up thoroughly afterwards. But, since this is your first day... Very well. Your group is dismissed for a moment. Be quick!"

Jesse hadn't even considered the fact that his companions would have to come too. He flashed them a guilty look, but all were already standing... and none seemed particularly upset with the idea.

Chapter 19: Danger Walks the Halls

They wandered along the corridor in silence. None yet confident enough in each other or their surroundings to break that boundary. Four pairs of smart, black heels clicked out a staggered rhythm on polished oak floorboards. Ridiculously lavish in a world rapidly running low on natural-grown trees. Along the walls were staggered frames emblazoned with the names of past students of note. These flickered through a seemingly endless catalogue of candid photos from those students' lives as professional fucktoys. It was possible they were still even updating in real time... Streaming in images every time one of their masters decided a particular act of debauchery was worth commemorating and proudly sending back to the place which had forged their favoured little pets. It was quite humbling to just pause for a moment beside one and observe simply how many fucked up and degrading situations might still be waiting in store for them after they left this prestigious institution.

Jesse walked with quick, but wobbling steps. He'd thought he mostly just needed to get out of the classroom and onto his feet... but now the idea had entered his head he did desperately need the toilet. Mr Durren had given them basic directions... but this one corridor seemed to go on forever. The metal plug between his cheeks had warmed up to his body temperature at least, but shifted inside him with every step. Combined with his clunky inexperience with heels, this all made him just stare intently at the next step ahead of him, using that driving focus to get him where he needed to be.

Of course, that also meant he was not sufficiently on the lookout for trouble further ahead... Such as the incredibly intimidating woman swiftly appearing around a corner and stepping into a collision course with the four, chained newcomers. No-one managed to get to him in time to pull him aside. Leading to the incredibly awkward situation of Jesse looking up to realise he had trapped the Headmistress of the whole school in a human net across her own corridor. The teen looked up at the raised eyebrow of Madame Stanfield herself, and very nearly wet himself just then and there. She didn't ask them what they were doing out of their classroom, or why he had decided to walk right up to her and block all passage... She just stood over him with that one curled eyebrow hanging like a scythe.

Jesse's mind went blank. A thousand ways to prostrate himself and apologise rushed in, but he couldn't find a way to say any of them... In the end the only words that came to mind were:

"Um, H-Hello Ma'am... How m-may I service you?"

The eyebrow shot up another few notches, in surprise but approval. A small smirk crossed the Madame's ruby lips at this clumsy, but quick-learning new pupil. If any of the older students had tried such a tactic they would have probably been subject to double the amount of lashes they would already be receiving for interrupting her train of thought. But, there was something sincere in this one that she couldn't quite put a finger on...

"Why not?" She offered, in sharply-humoured tones. Already popping open the single button on the front of her trousers and slipping them down to reveal a neatly-trimmed patch of pubic hair. Jesse was smart enough to drop instantly to his knees, shuffling forward till his head was between her thighs. None of the others dared move to help him... they all understood well enough: This was his test to pass.

Suddenly the desperate need to pee was only a background ringing in Jesse's ears. He had used his tongue before... When Betsy had decided she'd quite like to wrestle him until he was pinned into place with her sat on his face. But, somehow he thought this devoted trainer of 'perfection' might require a lot more than reluctant, haphazard probing. So he set to work actually working out what he was doing... Finding places and techniques which seemed to draw out some small reaction, and moving between those in as smooth a rotation as he could. By the end, he still couldn't really tell if he'd done well or poorly. Madame Stanfield only made a few polite coughing sounds in her throat. Yet, she promoted him back up to his feet, pulled her trousers up... and gently moved him to one side so she could pass. No further words were spoken.

Chapter 20: Four Porcelain Introductions

"Umm... that way round won't work for us, dude..."

Jesse looked confusedly at his neighbour-in-chains for a second... before he blushingly understood. There was a shy giggle from the third place along:

"I'm willing to give it a go!...I've always been a bit jealous that boys can."

It was instead decided that they would all rotate around and settle down on the four porcelain thrones provided. No walls or partitions divided these from each other, and for some reason a floor-to-ceiling length mirror on the far wall meant there was nowhere safe you could look. Jesse was pretty sure he wouldn't have been able to go at all, if he wasn't so desperate at this point. But somehow, the gentle sounds of four streams starting did bring a sense of relief and camaraderie.

"That lady is scary." Started up his nearest companion again. She seemed to have no qualms about chatting away in this moment. "I can't believe you got away with that... I bet she tasted like champagne and grown men's tears."

Jesse blushed, the flavour of Madame Stanfield indeed still on his lips... and not something he was going to try and describe.

"I'm Franceska, by the way... and this is Lizzy."

She offered her hand out towards him, which Jesse confusedly took... he had never shook someone's hand while peeing before. The black-bobbed and olive-skinned 'Lizzy' gave a little wave from further along.

"I'm Jesse..." He offered, then before he could stop himself said: "You're both... girls? I mean, you don't have...?"

Franceska just laughed. "Nope! Might've done once, who knows? Got a big-ol' blank where half my memories should be... but I've come out this end with a pussy and tits." She bounced her chest a little as if to prove this point, distracting Jesse away from the whole 'missing memories' thread she had so casually handed out.

But the face at the far end was also looking distinctly like she wanted to join in on these introductions, yet couldn't work out how to go about it. Seeing as he had already shared a meal with her, Jesse felt like he should at least ask her name.

"Suzy." Was the reply, through slightly-pouting lips, and the young man noted she had to keep one hand aiming something, below the rim... just like him. "Shouldn't we hurry up and make sure we get back to class?" He squeaked, clearly nervous about rocking any more boats after the lingerie incident.

Franceska again gave off an air of genial detachment. "Nah... We're definitely already gonna be punished after this one earned himself 10 minutes of licking out the headmistress... May as well get to know each other, while we've got the chance."

Suzy did not look entirely convinced... and a surge of guilt came over Jesse. They'd all only had to leave the lesson in the first place because of him... but then, the logic was quite sound... and none of them really wanted to rush back into that hot, stuffy lecture.

Fran could clearly see the internal beating that the boy was giving himself over their predicament. So threw a friendly spanner in the gears of the revving guilt-machine: "Oh, cheer up dude... Just look at this place! I don't think this is gonna be the last time we get punished for something that isn't entirely our fault. Better to get the ball rolling early really... Take the smacked ass while they're still holding back a bit, y'know?"