The Convent Pt. 06

THE CONVENT, PART 6

by Zenna Swallows

The whore wiggled her bottom invitingly. "You can spank me if you like," she purred.

The businessman laughed. "What, like this?" he asked, lifting his right hand from the buttocks he had been fondling and spreading to deliver a ringing slap.

He trailed his hands down the back of her thighs until he reached the stocking tops. She really did have the most gorgeous legs, accentuated as they were by the elegant hose and diamante-heeled slingbacks that were the only remnants of the outfit she'd worn to dinner.

"Or should I use this instead?' he continued, pulling his erect cock up to his belly and then letting it snap back down, first onto one cheek then the other.

She gave a throaty laugh. "Oh, I think your big boy wants to be somewhere else, don't you? Somewhere you've been thinking about all evening..."

And it was true, he had. Even by the high standards he'd come to expect from the Heavenly Bodies escort agency, this one was special. And after months stuck at home with nothing but his wife and an occasional hurried blowjob from the maid to keep him occupied, it was time to blow off some steam.

He'd intended to draw out their first encounter and go through a little foreplay. Maybe check out her oral skills. But there was the rest of the night to do that. So, when she reached through her legs to moisten her puckered hole and coquettishly asked "Why don't you see how deep you can go?" he only had one answer to give.

As the quivering phallus slipped inside her, Amanda let out a well-practised but utterly feigned groan of delight...

She drew no particular pleasure from the act - or at least none that would last. But in truth, she didn't mind being penetrated. Or she no longer minded, to put it more accurately.

The first twenty or thirty times it had happened at the Convent to Ryan, the man she had been, it had hurt - a great deal. That physical pain had subsided and then for the most part vanished, as Ryan's butthole stretched to accommodate even the largest of dildos, not to say an assortment of objects never intended for such use. But the mental torment had persisted, for a long time - as it was meant to.

Being fucked by the nuns' giant strapons and violated by everything from cucumbers to baseball bats was not just a punishment for the appalling way Ryan had treated the women in his life.

It was also intended to break him down, to cause him to lose any sense of masculinity or control, to align his mental image with the body he was being given. The body of a beautiful young woman, with budding breasts, widening hips, a pumped-up rear and a sweet voice. Not to say a shrivelled cock that could no longer be seen, let alone stiffen when aroused.

It was a transformation Ryan had fought as fiercely as he knew how. Faced with captors with vastly superior resources and a capacity to inflict debilitating pain through a device implanted inside him, he had quickly learnt that the fight could not be won either physically or quickly.

If he continued his overt resistance, he would likely be condemned to a life of servitude with the Order of St Pilarupta. Or, worse, turned into little more than a snarling beast and kept in a pen.

So instead, he dedicated himself to his training, not just rising from the rank of initiate to novice, but learning how to perfect the illusion of femininity, in everything from movement to makeup. Scheming all the while for the chance to escape, hoping that he could lull his jailers into the belief that he had surrendered his previous identity.

And for a few glorious minutes, he thought he had succeeded, on his first trip away from the Convent.

But his time in the city where he used to live and work proved to be a disaster. Not only was he unable to elude the nuns sent to watch over him, but he also discovered that there was no former life to which he could return. The Order had well and truly seen to that. They had not just ruined the reputation of the man he had used to be, but turned him into a fugitive from justice and a pariah to his wealthy family.

Far from being able to plot a return to normality, he was put to work, first as a stripper and then as a prostitute.

He spent several weeks dancing at a club, including in private for customers who wanted more than he could show or do on stage - which in practice often meant handjobs or blowjobs. And at night, he became a streetwalker, his beautiful features deliberately disfigured to give his role as a cheap transsexual whore more credence.

Worst of all, the one close connection he had forged during his time at the Convent was exposed as the basest of lies.

Agnes was a beautiful and apparently fragile young novice who had become his regular bed mate - and the one person besides himself that he cared about. His feelings for her had become so strong that he volunteered to take her place as a street hooker, rather than see her go through what he had experienced.

Only she turned out to be a plant, a skilled actor whose assignment was to deceive and seduce him. And to teach him a lesson, Sister Chastity said. A lesson about the danger of trusting anyone but himself.

Humiliated, Ryan spent the rest of his time in the city honing his abilities as a sex worker and doing what he could to recover his old determination.

In the process, he discovered just how well he could please clients, finding a grim satisfaction in his ability to make them come in his ass, or his mouth, or all over his boobs, which now comfortably filled his B-cups.

Thanks to one enterprising request at the strip club, he even learnt that he could use his feet to tease a throbbing cock to orgasm. Although the sticky mess left on his stockings taught him to be more careful in future about where he directed the resulting ejaculation.

What those experiences also produced, however, was an intense dislike for the men he was servicing. That was most obviously true of the ones who mistreated him. But it extended beyond them.

He was never seriously hurt. But he had to endure customers slapping his face with their cocks, mauling his sensitive tits, or reaching between his legs to try and find his missing genitals, despite his entreaties to leave them alone.

He was called a slut, a whore, a sissy or a bitch. Some customers deliberately removed their condoms, so as to be able to deposit cum inside him or all over his face. And there were those who wanted to fuck him in the most demeaning way possible, such as standing up against an alley wall in full view of anyone walking by.

Not everyone was like that. Many of the clients at the club in particular were gentle, even kind. But after initially enjoying some of the attention and compliments they lavished on him, Ryan gradually found his attitude changing.

Devastated by the lingering effects of Agnes' betrayal and ground down by the physical and mental toll of being a street hooker, his feelings for even the most considerate of customers soured.

Eventually, all he could see was the way these men treated him as an object of lust. And their failure to recognise his distress. Their failure to rescue him.

The fact that his self-control prevented him from showing just badly he was hurting, and indeed allowed him to put on an entirely convincing display of enjoyment, didn't excuse them. Nor did it matter that he could have asked to be rescued - thrown himself on their mercy and risked punishment for the chance to get the aid he desperately needed.

As he saw it, he was the victim. And these uncaring men were piling on his punishment, doing the very things which had got him into this predicament in the first place. All while admiring and celebrating a beauty he did not want. How could he think better of them for doing that?

By the end then, quite perversely, it was the anal sex that he came to find least offensive, especially when he was being taken from behind and didn't have to show any semblance of pleasure or appreciation, beyond some well practised moaning.

Each time he was fucked, the stimulation of his prostate brought him to the edge of orgasm, only for it to slip frustratingly away as the Order's cunning chemical blocks did their work. But those ruined climaxes were themselves a reminder of how little he could trust his sexual partners, regardless of how well or badly they behaved.

He was dimly aware that there were holes in his logic. But he had been manipulated and conditioned to a point where even as he fought to maintain his rebellion against what was happening to him, he was beginning to think in exactly the ways the Order wanted.

The nuns overseeing his transformation weren't aiming for mindless compliance. They valued his resilience and self-reliance, tolerated his attempts at resistance, futile as they might be. Even if the destination to which he was heading was one they had chosen, they wanted him to find his own way to that place.

The real turning point came when Ryan returned to the Convent and settled back into the rhythms of life there. In comparison to what he had endured while he had been away, performing his daily chores and rituals seemed far less challenging, soothing even. But even as he welcomed that familiarity, he could not help but notice that some things had changed.

One, of course, was the departure of Agnes, now no doubt gone to work her wiles on some other poor fool, at one of the Order's other facilities.

Her place in his bed was taken by a succession of other novices. All of them were good-looking, some as demanding as she had been that he satisfy their urge for anal stimulation. But none were quite as pretty or came anywhere close to eliciting any genuine affection from him.

The more significant absence, however, turned out to be that of Sister Felicity. He had no idea where the avenging demon who had once been his girlfriend might have gone, and he knew well enough not to ask any of the other sisters. But her disappearance, and with it the cessation of her relentless, creative and ferocious assaults on his body and spirit, brought about a remarkable improvement in the quality of his daily life.

There were still trials to endure, of course. While Sister Mercy rarely called on his services, her collection of strapons was deployed as ferociously as ever when he did visit her chamber. Sister Chastity was much gentler, but her insatiable appetite for cunnilingus never failed to leave his tongue leathery and his jaw aching.

In his first week back, he also had a familiar encounter with vindictive old Sister Beatrice, who had always loved using Ryan as a human toilet. When she pulled him aside and forced him to swallow what seemed like a never-ending stream of golden pee, he wondered how many litres she had drunk in preparation and how long she had crossed her legs, just waiting for him to walk by.

Yet after that one episode, she seemed to content to leave him alone, or pick on some of the other novices. In that and other ways, life at the Convent seemed notably less painful and humiliating than it had previously been. He could now go whole days with nothing more challenging than the requirement to engage in girlish chatter with the other novices, in between bouts of housework and silent prayer.

After six or seven weeks of this, however, a new challenge presented itself: a weekly assignation as an escort.

In his previous life, he had occasionally used the services of Heavenly Bodies, though only ever to purchase some very expensive time with a woman, never a transsexual - or at least not that he could definitely recall. Although there had been at least one beautiful creature who he remembered offering oral and anal sex only... so maybe he was wrong about that.

It would have blown his mind back then to discover that the escort agency was run by a group of nuns. Now, however, he could only describe it as mildly surprising. From what he had seen and learnt during his ill-fated trip to the city, the Order was a much bigger organisation than he had previously thought.

He now suspected that the Convent might be only one of many facilities they owned. If they could supply girls to a strip club and run a hooker welfare program, who knew what other irons they might have in the fire?

His task each week was a simple one. He was not on call or required to travel between jobs. He was hired out to a single client, for what might be anywhere from a few hours to the best part of a day.

How and where that time was spent was entirely a matter for the client. Most commonly, he was taken out for dinner, then back to a hotel for a night that might involve a lot of sleep, or very little. The amount of rest was generally proportionate to the client's age and inversely related to their stamina.

But there were many variations. Over the ensuing months he visited country mansions, spent time on a yacht, and even went up to high altitude to experience, if only very briefly, what it felt like to be fucked while in weightless freefall.

There was even a night in a dungeon, which was far from comfortable or enjoyable, although Ryan's intimate acquaintance with bondage and discipline, nurtured over many sessions at the Convent, helped him endure the client's enthusiastic attention.

In all this, and even for the dungeon master, he was expected to provide not just sex, but companionship. The conditions of hire, which were generally respected by the men using his services, relieved him of any obligation to talk about himself. But otherwise, he was encouraged to be charming, friendly and open.

The clients were assured that they could talk to and in front of him with complete discretion, and some of them were more than willing to share secrets about their personal lives, business affairs or political machinations, especially after he had drained them once or twice.

And he was completely faithful to the Order's promise, never breathing a word of what he had heard.

The tiny but very efficient microphones hidden in his earrings, however, were another matter entirely. It was only after a few weeks of wondering why he was always required to wear the same jewellery and then return it to the Convent's safe that it occurred to him to take a closer look at the items in question. But it was a discovery he kept to himself.

He found it surprisingly easy to set aside his distaste for the men he was servicing and be a good companion. After being taught to play the role of the submissive and obedient servant at the Convent, the only challenge now was to perform with more sparkle and a smile. And even that was something that he had learnt to do in chatting and joking with the novices.

There were certain upsides to his newfound role. The food and drink, for one thing. What he ate at the Convent tended to be nutritious rather than tasty. So, the chance to sample fine foods and wine again was very much a plus - though he found that both a diminished appetite and his strong desire to remain in control kept his consumption in check.

His biggest challenge was a two-year gap in his knowledge of current affairs, not to say music, television and other forms of popular culture. But even that he found a way to play in his favour, by making a big joke of it - and volunteering the information that he had been 'out of circulation' when transitioning to being a woman. Which of course was perfectly true.

The scary aspect was that he really had started to make that transition, mentally now as well as physically.

After the first few outings, he found himself beginning to think of himself as Amanda. It was Amanda who was working for Heavenly Bodies, Amanda who was playing the vibrant and flirtatious companion, Amanda who was sharing her body as often and for as long as she was asked.

Each time that Amanda returned to the Convent, it was Ryan who donned the familiar robes and went back to his chores and prayers. Even if it was a woman's face who stared back at him from the mirror, a woman's voice he heard, a woman's lingerie he wore every day, Ryan could still connect himself with the man who had been imprisoned and forced into a habit.

But when it was time to go out into the world, dressed in whatever fashionable and elegant outfit that had been chosen from the Convent's extensive and hitherto hidden array of clothing stocks, it was no longer Ryan who went to work. Unmoored from the Convent and any personal history, it was Amanda who spread her wings.

The disconnection was not complete. Amanda still had Ryan's determination to look for escape, for instance. But even though there was never a nun anywhere in sight, nor any visible sign of the Order tracking her, Amanda knew that she could not assume she was free to leave.

On a couple of occasions, she tried to head somewhere other than where she'd been told to go to meet the client - but she ended up there anyway, just as Ryan had when he made his break for freedom in the city.

She also tried to tell a couple of the clients that she was a nun, and that she was being held against her will and forced into sexual servitude. But the words literally would not come out of her mouth.

There were mental blocks at work then, conditioning she'd been given that cemented the Order's hold on her. So, for now at least, all she could do was to perform her job as well as she could. And watch, listen, learn and pray for a break.

And now, several months into her time as an escort, something had happened. This latest job was different. For one thing, she'd been given specific instructions that had nothing to do with her usual duties. And for another, the client was someone she already knew.

Someone she used to work with.

On a normal job, she was given a special phone that gave her directions and allowed her to call for a pickup when she was done. It could also be used to pay for anything she needed along the way.

Usually, the device gave her the client's name and photo, plus background information she could study while being driven to the meeting point. But today there had been nothing. She'd asked the driver, but all he knew was where to take her.

She understood as soon as she entered the lobby of the hotel and saw who was waiting for her. It was Dean Brandeis, Ryan's former boss.

Not his immediate boss. Dean was the chief executive of the business at which Ryan had been employed and there had been several rungs on the managerial hierarchy between them.

But as the man who ran one of the companies in the empire built by Ryan's father, Dean was a frequent visitor to the family's various houses and indeed often stayed over as a guest during his holidays, along with his elegant but frosty wife.

Dean and Ryan had got on well, which was surprising not so much because of the age difference as their very different attitudes to hard work. Ryan was never sure whether the older man had any idea how little Ryan actually did at the company. Perhaps he knew full well, but chose to ignore it because he had no expectation that his superior's son was there to do anything useful in the first place.

Whatever the story, Dean had always seemed to enjoy the younger man's company, especially as a drinking partner. On one memorably dissolute occasion, while away at a business conference, they had even enjoyed a foursome with a pair of identical twins, whose favourite trick was to swap places without warning and then dare their partners to figure out who had been fucking whom.

There were two things that Dean didn't know about Ryan. One was that before disappearing in disgrace, his gregarious young friend had occasionally shared his wife's bed, not out of any desperate desire for her company but simply because of the entertainment it afforded.

The other was that Ryan had no compunction about sharing with Mrs Brandeis what he knew about Dean's various infidelities - a breach of confidence that would eventually lead to a very expensive divorce, although Ryan only found this out much later.