The Convent Pt. 03

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Ryan is taught painful lessons by Sister Felicity.
5.8k words
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Part 3 of the 6 part series

Updated 06/11/2023
Created 08/07/2022
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THE CONVENT, PART 3

by Zenna Swallows

As Ryan hobbled towards his modest chamber in the novice wing of the convent, he tried to remind himself for the umpteenth time that his chance would come. Sooner or later there would be an opportunity to escape - and not just to be free of the building and the nuns who had imprisoned him, but to reclaim the manhood they had steadily stripped from him over the months he'd been in this hellish place. It was just a question of waiting...

Of course, that assumed there would be anything left of the man he'd once been, if and when that ever happened. The reflection he could dimly see in the windows he was passing certainly gave no hint of it. There was just an attractive nun in white robes with daringly bright and glamorous makeup that could just as easily have graced a stripper on her way to entertain a stag party. The sort of stripper he'd once have taken great delight in turning into a whore, simply by offering a large enough sum of money to overcome whatever scruples she might have had.

He didn't have to pay for sex, back then: there was always plenty of available pussy for a man with his wealth and privileges. But he'd always enjoyed doing so anyway, just because he could.

Now, he was the one being fucked as a routine part of his job. Only he was doing it for free...

"Are you okay sister?" asked an anxious voice. He looked up to see Agnes, the youngest and possibly the prettiest of his fellow novices, her angelic face alight with concern.

Looking that way wasn't very smart, he thought - she wouldn't want any of the senior nuns to see that. He wondered briefly if he'd let any of his own deep-rooted distress show. But he'd become very good at keeping the blank expression that the senior nuns expected of everyone else working for their Order. So he suspected she was simply noticing his awkward gait, an expression confirmed by her next question.

"Another class with Sister Felicity, I'm guessing?"

He nodded. She glanced around quickly to check there was nobody else nearby. "You might though, er, want to get a mop?"

She gestured behind him and he turned to see a series of wet blotches on the stone floor trailing all the way back to the door through which he'd just exited.

He wanted to roll his eyes. But he simply inclined his head to thank Agnes, then headed for the nearest broom cupboard, trying even harder to clamp his legs together and stop the flow from his abused ass and sodden panties.

Behind him, Agnes cleared her throat. He glanced back at the young novice, his eyebrows arched. "We, um... It's you and me. You know, tonight. I just saw the roster." Her voice sounded uncertain, yet with an undercurrent of anticipation.

Ryan would dearly have liked to leave it there. But he really couldn't. Keeping onside with the other novices was important. Not just because if the time came to escape - or when, he told himself firmly - he might need help from one of them. But also because of what they could do to put him in the bad books of the women who ran the convent.

He already had enough experience of being punished for marginal or imaginary failings. He didn't want them thinking he was anything other than a compliant sissy who was fully cooperating in his feminisation.

"Thanks sister," he forced himself to say, a brief smile flitting across his otherwise serene features. "I'll see you then." Without giving her any chance to respond, he resumed his awkward progress down the corridor.

He genuinely wasn't sure what was worse - having to sleep with Agnes, or to listen to the sound of his own voice.

When he'd been summoned to see Sister Mercy two months before, for the test that would determine whether he embarked on training as a novice or was consigned to menial servitude for the Blessed Order, he would have leapt at the chance to get his voice back and once again share his bed with beautiful young women.

It would have been a lesson to be careful what you wish for...

He could still recall his reaction after the end of his test - or ordeal, to be more accurate - as he was being half guided, half carried to his new living quarters. The shock when Teresa, one of the novices who was helping him, asked if he was "bleeding from, well, you know" and needed medical attention.

He understood the question well enough and was not surprised that they might expect him to have suffered some damage. The chances were pretty good that they'd been through something similar themselves, when they completed their initiate's training.

No, what astounded him was that Teresa could talk. He had thought that the novices, like him and all the other initiates, not to mention the servants, couldn't speak. That their voices had been ripped away by the mad women who ran the convent, as a means both of reinforcing their servility and making it harder to plot any escape.

Seeing his obvious confusion, Angela, the other novice, had quickly explained that novices were forbidden to speak except when in the presence only of another novice, or of a senior nun. And the prohibition was absolute when in certain parts of the convent - like the ones to which Ryan had been confined during his initial period of captivity. But where they were now, talking was fine.

And yes, Teresa had added, Ryan would soon be able to enjoy that privilege as well. As that revelation sank in, all the pain, exhaustion and humiliation he'd just suffered seemed to melt away. He still had enough self-control left to hide his elation. The iron discipline that had got him through his initial training and won him the opportunity to pass on to the next stage of his re-education still held. But inside, he was celebrating. He was going to get his voice back!

Only it wasn't his voice at all, as it turned out. It was Amanda's.

The name was one that Sister Mercy had bestowed on him as what she called a "reward" for finishing his initiate's training and showing himself worthy of becoming a novice. Along with the white tunic and wimple that would now become his daily uniform, she told him solemnly, it would be an important reminder of his new status.

He hated it, with a passion.

It was strange, but while he certainly resented the way he had been so callously deprived of his former and very privileged life, he had somehow managed to avoid getting consumed with ill-feeling towards any of his captors. It was simply too dangerous. Any animosity he showed would be returned tenfold, of that he was sure. So better to just avoid making it at all personal.

He had also tried to reconcile himself to the lingerie, makeup and high-heeled shoes he was forced to wear, to the way in which his genitals were concealed beneath a pussy-shaped prosthetic, even to the body changes that constant doses of hormones had caused. Not to like them, or in any way accept their permanence. But to avoid thinking about what they were doing to him, as far as he possibly could. It was just self-preservation.

But he loathed the name Amanda. And the senior nuns knew it, he was sure. Even though he was positive that he was suppressing any overt reactions, he could just see the delight they took at saying his new name at every possible turn. Although maybe too, he conceded, they simply wanted to condition him to the new gender he was being forced to assume.

In any event, Amanda's voice did not make an immediate appearance. The day after his test, he was taken to the convent's small surgery, given an injection... and then woke up in his new bedroom, swathed in bandages, and with no recollection of what had happened to him in the meantime.

He had the sense that quite a lot of time had passed, and he speculated that he might even have been taken somewhere offsite. But with nothing to mark the passage of days within the convent, and no link at all to the outside world, he couldn't be sure.

It was not until a further ten days or so had passed that the bandages were taken off his throat and he was allowed to talk again. At first he just sounded a little croaky, understandable given the months that had passed since he had last been able to speak. But as the croakiness eased, he realised to his horror that his voice had been altered.

The pitch was much higher, but what really mattered was the change in timbre. There were simply no lower tones left. His baritone had become a soprano. It sounded thin, breathy and indisputably feminine.

So he now had a girl's voice. Amanda's voice.

Paradoxically, the silence that was still expected of him in large parts of the convent had now become something of a boon, not the restriction he had until so recently lamented. But there was no escaping the sound of his transformed tones in the lessons he was now undergoing, classes in which he and the other novices were being taught to speak not just with the tones of a young woman, but with their rhythms and emphases.

And whenever he was in the novices' common room, there was no relief at all. Far from silent contemplation, the "girls" were expected to chat to one another more or less incessantly, not just about the fashion, lifestyle or celebrity gossip magazines they were also encouraged to read, but about each other's pre-convent lives.

Not their real ones, as men - as Ryan was now more or less certain they had all been - but an assumed life they were being carefully coached to construct.

To give them an incentive to develop and remember their fake histories, the novices were constantly being tested by the senior nuns. If they were caught out in some inconsistency or lack of knowledge - such as the name of the high school they had attended, or of their favourite teacher - they would be soundly spanked and a note taken.

Ryan was desperate not to forfeit any possible chance of freedom, so he worked extra hard to get his story straight. But doing so only served to blur his identity even further...

Another place that he couldn't escape the other novices was in bed. Each night, a pair of novices was assigned to sleep with one another - stark naked, and in a tiny bed that was barely big enough for one.

During his time as an initiate, Ryan had largely managed to avoid thinking about the loss of his old sex life. Although the novices were all very attractive, and so too some of the servants and other initiates, he only ever got to see them in robes and headwear that concealed all bar their faces. And while he was required to eat out many of the senior nuns, some of whom at least might have excited the old Ryan's attention, the forceful and humiliating way in which they used him made it easy not to get aroused. And besides, he couldn't, not with his cock and balls frozen and tucked away.

But having what to all intents and purposes was a gorgeous young woman curled up against him - or, worse still, squirming around - was another matter altogether. And what had been done both to his budding breasts, and theirs, really didn't help.

As a result of something that he assumed had happened at the same time his voice was raised, his steadily growing boobs had become super sensitive, the nipples positively exploding with sensation whenever they were touched, regardless of how lightly. Even putting on the lacy bra that had become a routine part of his underwear set them off. The feeling was indescribable, a combination of a tingling inside and a deep ache for further stimulation.

What made it even more difficult was that some novices found it almost impossible to resist the desire for their boobs to be stroked, licked or kissed. The ones with self-control, like Ryan, gritted their teeth and tried to stay as still as possible. But others wanted to be touched and were all too happy to return the favour. Even if denied by their partner, they would take every opportunity to press tight up against the body next to them and sensuously move against it.

The worst of them, by far, was Agnes. Not just by reason of looking and feeling so gorgeous, but because she was so hard to refuse when she wanted to make out...

With unbidden thoughts of Agnes and her luscious young body swirling around his head, Ryan reached the door to his room, opened it and then paused on the threshold. What was it he'd forgotten? Oh god, the mess in the corridor outside Sister Felicity's room!

Silently cursing himself, he turned to check that he hadn't left a trail all the way back to his chamber. For a mercy, he hadn't. He stood there for a second, unsure what to prioritise, before deciding he needed to clean himself up first.

Quickly grabbing some clean underwear and stockings, he forced himself to walk slowly to the nearest bathroom. Running was never a good choice at the convent, given the strictness of the rules - and besides, the six inch heels he was currently being forced to wear made that almost impossible.

After changing as rapidly as he could, and dropping the items he'd removed into a laundry basket, he located a mop and bucket and went back to Sister Felicity's room. Hopefully she was either still inside, or had headed off somewhere without noticing the stains on the floor.

As he came round the corner, his heart sank. She was leaning against the wall, waiting for him, her broad smile doing nothing to hide the evident pleasure at catching him out - or the anticipation of the punishment she was undoubtedly about to mete out.

"What's up... Amanda?" There it was again, that slight hesitation, the emphasis on his new name. "Was there something you forgot? Or were you just desperate to give me another chance to even up the score between us?"

Her tone, as ever, was both mocking and dismissive - and so different to what it had once been.

Less than a year ago, but somehow also in a different lifetime, the nun he now respectfully addressed as Sister Felicity had been his girlfriend, Dana. She had been with him when he came to this accursed convent in search of emergency accommodation, and she had undoubtedly been one of the reasons, perhaps even the main reason, he was seized and imprisoned. Or rather, to be fair, his treatment of her had caused that.

He had not seen her after they were separated on that first night - not until he took his test with Sister Mercy, and discovered to his horror that it would not just be the older nun fucking him with a giant strapon, but the young woman he had once so casually used to entertain and arouse him.

Superficially, she was just as he remembered. She still had the beautiful face, the full, natural tits that he so adored putting his dick between, the killer legs shaped to perfection by high heels.

Her sensational body was even clad in the kind of lacy black lingerie that he had once insisted she wear, even to her day job as his (very) personal assistant. Only the black and white wimple that concealed her raven locks was out of kilter with the image in his memory.

But one look at her expression was enough to tell him that this was no longer his Dana.

He discovered soon enough about the contempt in which she now held him. That was not a surprise, for it turned out the nuns had been all too willing to reveal how he had cheated on her, not once but often, with her friends, her co-workers, even both her (real) sisters, not to mention the occasional prostitute.

And of course they hadn't just told her, but showed her some of the recordings he'd kept, the texts he'd sent, the humiliating descriptions he used when talking to others about her. It readily explained some of the venomous and vengeful treatment he was to experience at her hands.

But what really chilled him at that first reunion was her manner. Because the look on her face, the tone of her voice, even the way she held herself, all suggested a woman who had undergone her own transformation. This was not the subservient airhead he had known, This was a woman in full control of herself - and of him.

The nuns of the Blessed Order of St Pilarupta had made her one of her own. And Sister Felicity, as she now called herself, was ready to drive home that point, both literally and figuratively.

He could still recall the shock, worse even than the physical pain, when she first penetrated his virgin ass with her enormous black dildo, the bulbous head tearing its way through the feeble barrier of his tight rectum.

Mercifully, she had used some form of lubricant, otherwise he'd have been bleeding like a stuck pig. But what he couldn't get over - and still hadn't really, regardless of how often she or any of her sisters repeated the treatment - was the wrongness of being taken in that way.

He was a man. That meant he entered women's bodies, asserted his dominion over them, planted his flagpole in their pussies or asses to claim them as his own - not the other way round. Intellectually, he had known that men could be fucked. But he didn't really believe in it, not in any practical sense. Because he would never fuck a man. And being fucked himself? Simply inconceivable.

Only now he had no choice but to believe it. And the worst thing of all was that he was being fucked by a woman who for the past year had been entirely at his disposal.

As his butt was being reamed, he wept tears of loss and rage, all his carefully constructed composure shattered. And yet some of his discipline held - he did not try to wiggle away or at all escape his violation.

It would have done no good, he knew. Sister Mercy had the power with one press of the button on her signet ring to trigger the device implanted deep in his ass. He had only once experienced the pain it could administer for any sustained period. And once was enough.

He wasn't sure then, back at that first reunion, whether his ex-girlfriend had her own button, but he guessed she would - correctly, as it turned out.

Fortunately for him, on this occasion, his loss of control must not have been visible to Sister Mercy, who was still slamming her dildo into his mouth while her new colleague took him from behind. Or perhaps she just thought he was unable to cope with the pain of having so large a phallus thrust deep into his innards.

Soon enough, however, he had something else to worry about. Because even as his back passage started to stretch to accommodate the intruder, and the pain began to lessen just a little, another sensation began to take over. Pleasure.

At first, he couldn't be sure what it was he was feeling. It was all so new and unfamiliar. But as the assault on his ass progressed, and his former girlfriend began to drive her fake cock inside him with the same ferocity and reckless disregard that he had so often shown when fucking her, he started to realise that something inside him was feeling... good?

It was like - a special sort of glow. A pulsing glow, that grew gradually stronger, firing little bursts of arousal through his groin. Not going anywhere, exactly, and certainly not to his trapped, shrunken and all but forgotten penis. But still, somewhere he could feel it.

He didn't know to this day exactly why and how he was able to be stimulated through anal penetration. The magazine articles he would later read on "The Joys of Anal Sex" were talking about a female physiology that he didn't have - not yet, anyway.

Some of the novices talked about men having a prostate gland, and maybe that was it. Perhaps it was something to do with the control device implanted in him, firmly and deeply enough, it seemed, that it was not dislodged by even the biggest of dildos.

All Ryan knew on that first occasion, and every subsequent time he was fucked, was that he liked it.

Or rather, he liked it, right up to the point at which he didn't. Because as the sensations grew, they gradually seemed to mount in intensity, spiralling upwards towards a point of release for which he began to ache.

Although he had never felt exactly this way before, he was sure that he was going to come, to have the orgasm chemically or surgically denied to him for so many months. The pressure was going to build until the dam burst and the sweet release of climax surged through his body.

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