The Convent Pt. 05

Stupid, stupid, stupid!

Ryan could hear the word echoing in his ears, both in Sister Chastity's cutting tone and his own internal voice. Except that where her condemnation was tinged with amusement, his reproofs carried nothing but despair and loss.

He punctuated his self-denunciations by periodically pounding on the hotel bed on which he was lying. But that didn't bring any relief. The mattress was so soft that his fist simply sank into it, absorbing what little energy he was able to muster with his atrophied muscles.

It was strange, he reflected, but throughout the two years he had been trapped at the Convent, he would have killed for the opportunity to sleep in a comfortable bed. Yet so used was he now to his chamber's hard pallet, sinking into the surface of this bed almost felt like slipping under water.

Even if he had felt able to sleep, and bone weary as he might be, he knew that the unfamiliarity of the mattress would have kept him awake.

He briefly considered rolling over and punching the wall instead. But deep as he was in depression, he had not lost his sense of self-preservation.

There might be some temporary relief to be had from the damage he would do, the physical pain somehow easier to endure than the profound mental distress he was experiencing. But there would be no hiding his self-harm.

The nuns of the Blessed Order of Saint Pilarupta, the ones who had taken him into captivity after he had checked into what he thought was just an eccentric old hotel? They saw everything, knew everything.

They could and did inflict pain on him. He had come to know that intimately, especially at the hands and devices of Sister Felicity, the avenging demon who had once been his oppressed girlfriend. But the pain was theirs to administer, and hers above all. If he physically damaged himself, he knew, the retribution would hurt a lot more than bruised and bloodied knuckles - and last much, much longer.

So all he could do was hurl empty imprecations at his weakness. And try very hard not to think about what a second day of release from the Convent might bring.

Only thirty hours or so earlier, he had embarked on what he was told was a "field trip" to the city in which he had previously lived and worked. He had travelled there with Agnes, the delectable young novice with whom he had become reluctantly but irretrievably infatuated.

Supervised only by the handsome Sister Chastity and sour old Sister Patience, he had envisaged being able to use the crowded streets to escape their clutches, and somehow make contact with his family.

And yet even when he slipped away from his escorts, the control they had over him could not be evaded. Through some means he still didn't understand, but presumably involved a form of hypnosis, he had been conditioned to go where they wanted. And when Sister Chastity allowed him to call his father, he learned a shocking truth.

As far as the world was concerned, Ryan Seldon was a paedophile who'd stolen from his family and disappeared. There was no help to be had from anyone who had previously known him, least of all the man who had been the source of all his wealth and social advantages. The rage Ryan had heard at the mere mention of his name had convinced him of that.

So instead of the Great Escape, the trip to the city became what it was always intended to be - a chance to heap more humiliation upon him. To teach him more lessons about what the Order believed the superior sex had to endure.

During his enslavement, Ryan had been made to look, talk and act like a woman. And not just any type of woman, but the epitome of beauty and sex appeal. He was no longer Ryan, but Amanda. And the makeup, lingerie and ludicrously high heels that he now habitually wore all had one aim - to make him an object of male desire.

At the Convent, paradoxically, the sexual abuse he endured in this guise had all come from women. The senior nuns, those who wore the black, had used him unmercifully, just as they had the other male novices, initiates and servants.

Much of the time, that simply meant being called upon to finger or lick the nuns in the way that another woman might - though the pleasure was never reciprocated.

But for Ryan especially, it could also involve having to suck or be penetrated by huge dildos - and frequently endure large quantities of fake sperm being pumped down his throat, all over his face, or deep inside his ass. Sister Felicity had delighted in making him experience the treatment he had doled out to her and so many other women during his former life.

In the city, the lessons he had been learning were taken to a whole new level.

It had begun at the strip club to which he and Agnes, dressed in a parody of their usual outfits, had been taken to dance. Before they went on stage, he had been sick with worry. Yet it had been surprisingly easy to perform. Partly because they had been practising at the Convent. But mostly because he had been able to lose himself in the delights of the little blonde's nubile body. Their sex act, far more real than the watching crowd may have suspected, had helped distract and insulate him from the baying men around them.

But he should have known not to relax. Because the price of a successful performance was having to do a series of private shows, for which the men concerned had to bid just to get a booking.

And that's when the fun really started. Or at least what the nuns guiding and profiting from his efforts would have regarded as fun.

The first show was easy enough, for a smitten young man who was satisfied just with being able to watch and gently caress what he clearly thought of as some kind of goddess.

The second man was a different story. He wanted extras. And when Ryan quoted a ridiculously high price for a blowjob, he was willing to pay it. Which was how the captive and sissified young man came to experience, for the first time, a real cock in his mouth.

The huge size of the client's appendage had not disconcerted him. Large as it was, he'd had to wrap his lips round even bigger phalluses. So while getting it in his mouth was difficult, the physical act was manageable. He could even let the organ slide down his throat without gagging too much, to the delight of its owner.

"Fuck yeah Mandy," the man had exclaimed. "Swallow that big dick, all the way down baby!"

Even the inane commentary was somehow not too disturbing. But the feel and taste of what he was sucking was something else altogether.

No matter how realistically sculpted, the dildos to which he was used were completely inert. Even when they spurted cream, there was no sense of life, just motion.

The warm, pulsing flesh in his mouth was completely different. And so was the smell of the man's crotch. The overpowering, musky aroma was unmistakably masculine and far removed from the feminine scents to which he had become accustomed.

The first mouthful was nearly enough to make him throw up. Only his iron self-discipline, honed over what he had learnt only today was at least two years of captivity, prevented him from rearing back in disgust.

As it was, for a moment he thought of admitting to the client that he had made a mistake, of trying to get away with just a handjob. He would just have to accept whatever retribution would follow from the nuns, who were no doubt watching through hidden cameras.

But at this point, he was still committed to finding a way of getting his life back. And if that meant enduring this latest humiliation and continuing to build trust with his captors, while he kept looking for some chink in their defences, some loophole that might lead to freedom, so be it.

Characteristically, he let none of his turmoil show. Instead, he lifted his head to look up at the client and forced a lascivious-looking grin as he ran his tongue over the bulbous purple head. Ignoring the fluid that was already starting to ooze from the tip, he gave an appreciative "Yum!" and started bobbing his head up and down.

As he reflected later, his decision to endure the sensation of sucking another man's cock might well have been a turning point. If he'd rebelled then , he would undoubtedly have been punished, and severely. His life could well have turned out worse, in all kinds of ways.

But maybe he would have been spared at least part of the disturbing sequel to his shift at the club.

As it was, he proved to be surprisingly efficient at giving head. In only a matter of moments, and well before the panting and increasingly vocal client ran out of his allotted time with "Mandy," the throbbing shaft in Ryan's mouth erupted with a positive geyser of spunk.

The quantity of fluid was something the abused novice was well and truly accustomed to ingesting. But the taste was something else.

At the Convent, any fake semen that Ryan was fed was delicious. And so too, more surprisingly, was the real fluid that oozed in depressingly small quantities from the shrivelled remnant of his own cock, or that of the other "girls."

But this was different. It had a salty tang, with a rancid undertone that Ryan somehow knew would linger on his tongue and the back of his throat, even as he gulped it down. Was this what real men's cum was truly like? Or was there something wrong with this particular batch?

The one thing Ryan knew for certain was that he found it disgusting.

After he got rid of the client - though not before having to remind the man to use a credit card to pay for his extras and listen to an obscene but rhapsodic description of Ryan's cocksucking talents - he took a bathroom break not to pee, but simply to wash away the aftertaste.

Unfortunately, it was to return soon enough. And he learnt that there was nothing special or different about the first man to blow his load into Ryan's willing mouth. The rest tasted just as bad.

Over the course of the long hours he spent doing private shows during his first shift at the club, he did manage to keep the number of blowjobs to a minimum. Some clients didn't ask about extras at all. With others, he was able to get away with offering just a pricey handjob.

But much as he would have liked to keep it at that, he was sure this would not go down well with either the manager of the club or the nuns who had brought him here to work.

So for those who specifically wanted it, or who insisted he lay out everything he was prepared to do and then chose the most expensive option, there was no escaping the need to open his painted mouth once more and wrap his ruby-red lips round their eager cocks. None of them were as big as that first man's. But they all tasted equally gross.

Ryan did learn one valuable lesson early on, however, which was to maintain a degree of control while he was delivering his oral ministrations.

The second client he serviced in this way, a burly young man in an ill-fitting suit, insisted on standing up and having Ryan kneel before him. Ryan realised his mistake when the client grabbed his head and vigorously fucked his face, before pulling out at the last moment and spraying jizz all over the novice's face and hair.

That led to a frantic clean up that was only partially successful in teasing the gobs of spunk out of Ryan's long raven tresses - and a determination thereafter to keep the clients firmly seated in their chair.

It was late afternoon by the time Ryan was finally relieved from his work in a room which, despite the air-conditioning, had come to reek of stale sweat and cum. Jaw and neck aching from all the cocksucking he had done, and with a belly uncomfortably full of semen, the last thing he felt like doing was going back on stage to dance.

But after the shortest of respites and a quick chat with an equally shattered Agnes - or Angel as she was being billed - it was time for the two of them to perform again. Once again, their act wowed the watching crowd, which had grown considerably from earlier in the day. While the kissing was still real enough, their sex act was entirely faked this time. Not that it seemed to matter to the audience.

Mercifully, they were not sent straight off to do more private shows. They had evidently reached the end of their contracted time, because despite the manager's obvious disappointment, Sister Chastity and Sister Prudence insisted on leading them back to the hotel.

When they returned, however, there was a surprise waiting for them in the room that Ryan and Agnes had been told they would share. A hard-faced young woman rose from one of the chairs as they entered and stared at them suspiciously.

"You the nuns?' She directed the question at Agnes and Ryan, frowning as she took in their shorter than usual habits and high heels. Her own attire was equally striking: a black crop top that left much of her torso exposed, a tight red leather mini-skirt, fishnet tights and ankle boots with platform heels.

"Yes, that's right dear," answered Sister Chastity in a level tone, pushing past Ryan. You must be Kandi, yes?"

"Yeah, that's me," said the woman. She seemed nonplussed by the business suit the older woman was wearing, and kept flicking glances at Ryan. "You got a job for me? Some guy in a limo gave me a coupla hundred, said I should come here, there was something special in it for me?"

"There is indeed," answered Sister Chastity with a thin smile. "But it's not the kind of job you might be expecting. You're getting a night off. You can spend it here in a nice comfortable bed, order whatever you like on room service. Relax, put your feet up, watch some movies."

A worried look crossed Kandi's face. "But I can't, it's Steve, right, he'll be expecting -"

"Don't you worry about Steve," interjected the nun smoothly. "We've squared it away with him. Sister Patience here can give you some information about our program, if you like. But for now I suggest you go and have yourself a nice bath. You can take your clothes off here - just leave them on the chair. You'll find a robe you can wear hanging up in there." She gestured towards the bathroom.

Kandi hesitated, but the look of serene control on the nun's face, combined with the habitual glower her older colleague was sporting, seemed to persuade her that arguing would be futile. With a complete absence of self-consciousness, she stripped off her clothing then stalked away to the bathroom. Ryan noticed that her thin frame was covered in blemishes and scars.

As the door closed behind her, Sister Chastity answered the question that Ryan was far too disciplined to ask aloud.

"The program's called Hooker Care," she said. "We take working girls off the street for a while, give them the chance at a bit of luxury. An opportunity to get off their feet, you might say ... though in a different way to what they're used to. If it seems like they might be up to it, we'll give them the opportunity to get right out of the game, buy out their pimp and start giving them some training in a different career."

Her smile vanished. "Not all of them get there though. Some are just too far gone. Whether it's the drugs, or they're just completely dependent on the men controlling them ... We can only do so much."

She sighed. "We'll see how Kandi fares. It may or may not work out. But because she has ... obligations tonight, we'll need to send someone to do her shift."

She glanced at Ryan and the grin was back. "That's where you come in, Amanda. Put these on please." She gestured at the clothing Kandi had discarded.

Ryan stared at them in shock, his mind whirling. He desperately wanted to protest that he had already done his work for the day, that he had given - and taken - all that he possibly could. But he knew that it would do no good, that punishment would surely follow if he resisted.

So instead, as he moved slowly to strip off his outfit, he voiced the other concern that was pressing on him. "What about Angel - I mean, Agnes? Does she have to do this as well?"

He heard a hiss of disapproval from Sister Patience. He couldn't see Sister Chastity's face as he pulled the habit over his head, but her tone didn't seem to suggest any affront at his question.

"Not tonight. She'll be spelling someone else tomorrow evening. For now, she'll be acting as Kandi's personal maid, to make sure the young woman has whatever she wants. Including in bed, if that's what she's into. You can sleep on our floor tonight instead - after you get done. Understand?"

"Yes sister," responded Ryan submissively, as he began to pull on Kandi's clothes. They were grubby and stained, and he had to work hard not to wrinkle his nose at the smell. The boots proved to be half a size too small for him, but he crammed his toes into them without complaint.

"Good," pronounced Sister Chastity, as she inspected him. "Only one problem we need to fix. Sister?"

Ryan glanced around to see Sister Patience advancing on him with a large hypodermic needle. He steeled himself not to show the alarm he felt, but from across the room he heard Agnes give a frightened little mew.

"We can't have you going to work Kandi's patch looking like that," explained Sister Chastity conversationally. "You're far too pretty. There'd be a riot. Not the customers, the other girls. Not at all the sort of competition they'd appreciate. They'd be levelling the playing field with a broken bottle, I shouldn't wonder. Or their pimps would."

"Over here," commanded the older nun, grabbing Ryan's unresisting arm and dragging him underneath one of the spotlights set into the ceiling of the hotel room. "Now hold still," she added, positioning the needle just below his right eye. "This won't hurt a bit."

She was good to her word: the injection hurt a lot. The second one, which went in just above the same eye, was even more painful. So was a third, into his left cheekbone.

Characteristically, however, Ryan refrained from even whimpering. He had endured far worse, especially when Sister Felicity was recreating some of the nastier bondage scenes she had found saved on Ryan's phone. Nothing brought home more effectively that he was the author of his own misfortune than being compelled to endure the degrading and painful treatment he had previously enjoyed seeing visited on young women.

He still shuddered at the time when she left him chained up with vibrators running full speed in both his ass and strapped to the only part of his cock that could still be reached under the prosthesis that both restrained and hid what was left of his organ. He had been required to count every failed orgasm that the incessant stimulation produced, over what seemed like hours of torture.

As the sting from the injections faded, his eye began to swell up, and then in turn his cheekbone. Sister Patience peered at him, gave a satisfied smirk and swung him round to face her younger colleague. Sister Chastity nodded and held out a small handbag.

"This has everything you need," she said, "including some fresh lipstick. You can put it on over there." She inclined her head towards a mirror on the wall.

Ryan rummaged in the bag. It held a tube of lubricant, a collection of condoms, some wipes, what looked like a small timer, and a lipstick in perhaps the brightest shade of pink he'd ever seen. As he went to apply the latter, he froze at the sight of his face.

The injections had not just created bumps that marred the symmetry of his features. They had caused his previously flawless skin to develop blotches that could be seen even through the layers of makeup. What stunned him, however, was his instinctive reaction to the changes.

His transformation at the Convent had been hard to accept. And yet the emphasis on creating an appearance that was not just feminine, but one that fitted the masculine ideals of female beauty, had forced him to invest a lot of time and effort each day in making himself pretty. Plus, as it turned out, he had quite a talent for makeup, and he had come to take pride in not just meeting the nuns' exacting standards, but exceeding them.