The Convent Pt. 05

Which perhaps explained now why he felt such a sense of consternation. His first thought was: I'm not beautiful anymore! Quickly followed by: I can't go out looking like this!

He pushed those reactions down and got on with painting his mouth. But something must have shown in his expression, even through the disfiguration.

Peering over his shoulder, Sister Patience smirked and said tartly: "Don't worry, you vain little tramp. You'll get back to being the prettiest princess in the kingdom by the time you return from spreading your legs."

She cast a scornful glance sideways at Agnes, whose thoughts about what had been done to her favourite sleeping partner were, as ever, written all over her face. "Or second prettiest anyway."

But Ryan had no time to dwell on Agnes' feelings, or indeed the vanity he had apparently developed over his long period of learning to look and act like a woman.

He was whisked away by Sister Patience and soon enough found himself being driven out to a part of the city that was not far away in distance, but worlds removed in terms of affluence and security from those he had inhabited during his time as a spoiled young man.

The driver who took him to what could only be described as a disreputable junction in a derelict and run-down part of town was the same man who'd ferried him from the Convent earlier in the day. But the limo was gone. In its place was a battered hatchback more appropriate to the surroundings. Ryan wondered if it was the driver's own vehicle.

Pulling up outside a row of what looked like derelict houses, the driver pointed out a large figure, half-hidden in a doorway. "That's the man in charge," he said. "Name's Steve. You do what he tells you - exactly what he says, understand? Do the wrong thing round here, and you might lose something. Like, you know, a finger. Or an eye. Or the right to breathe."

Ryan nodded and got out of the car. He glanced at Sister Chastity, who was sitting in the backseat and, he noticed, staying out of sight. But she simply inclined her head in the direction the driver had pointed.

Tottering nervously across the uneven ground in his platform heels, and conscious of his thumping heart, Ryan approached what he assumed to be Kandi's pimp. His tattooed face was not a comforting sight. Nor was the large knife he was tossing idly from hand to hand.

"Fuck you want, bitch?" he growled. It was impossible to say how old he was. He could have been anywhere from his teens to late 30s. All that could safely be assumed was that he had seen (and probably done) a lot of bad things.

Ryan swallowed. "I'm ... I'm Mandy, s-sir" he squeaked, shivering despite the warm evening air. "The n-n-nuns sent me?"

"Uh-huh," grunted Steve, then peered down at Ryan. "You one of their ladyboys, right?"

"Y-yes sir."

The man's face twisted into what might either have been a grimace or a smile. In the dim light it was hard to be sure. "Well you look like a fucking girl anyway. What was the name again?"

"Mandy, sir. It's Mandy. Or Amanda. You know, whatever -"

"Mandy will do. Now shut the fuck up and listen. See that corner there, where Suri and Loretta are?"

He pointed to a nearby pool of streetlight, where two listless looking women were standing. Ryan nodded.

"Get your skinny fucking ass over there, and see if you can get any takers. Anyone asks, you only do anal, a hundred for twenty minutes, two for an hour. Pay in advance, cash only. You can use the front room of the house behind me. Or you can get in their car. But if you do that, you get them to park in the driveway here and give me the keys. And don't get in until they've done that. Got all that?"

"Yes sir."

"Any questions?"

There were many that Ryan wanted to ask, but none of them seemed any more pressing than the others. So he shook his head.

"Right, well fuck off then."

Ryan hesitated and then trudged off. The car in which he had been brought had disappeared, he noticed. So he was on his own. He thought about saying hello to the other two streetwalkers, who like him wore the shortest of skirts and the skimpiest of tops. But the frosty glares he received when he joined them put an end to any such thought.

Moving a few metres away, but staying within the patch of light cast by the lamp against which one of the women was leaning, he picked a spot to stand and looked around.

He had honestly not known that street hookers still plied their trade. He himself had hired prostitutes before, but they were high-end escorts - that, or strippers who he had successfully turned into whores simply by offering them enough money. The idea that there were still women who stood on street corners, rather than work in licensed and presumably much safer brothels, was quite a shock. Though nowhere near as shocking as actually being one himself.

Looking around, which he tried to do as unobtrusively as he could, he could see other hookers working either side of the street he was on. The area was far from busy, but cars drove along the street regularly enough, often quickly, but sometimes at a slow pace that hinted at the area's main attraction - if that's what it could be called.

There was also a steady stream of pedestrians heading up or down a side street that Ryan thought might lead to a nearby strip of restaurants and nightclubs.

Some of the arrivals, especially those who clustered in boisterous groups, were plainly just interested in sneaking a peek at the trade going on - or indeed the scantily clad women on display. If they got too close, burly figures - Steve's equivalents, no doubt - would quickly emerge from the nearby shadows to move them on. But there were also single men who trudged past, most keeping their heads down until directing what they clearly hoped were covert glances at the human merchandise.

Several went past Ryan, before one hesitated, then asked him in a low voice: "How much?" Trying his best to keep his voice steady. Ryan answered as he had been instructed. It prompted an almost imperceptible shake of the head, before the man moved on. The same thing happened with the next few men to ask, along with the drivers of two cars who stopped at his corner.

After nearly an hour, Ryan was beginning to wonder what he was doing wrong. Both the other hookers near him had found customers, though he could hear they were quoting much cheaper prices. He wondered if he should somehow change his pitch. Perhaps smile, or even be cheerful?

But unlike the club, where he had found it relatively easy to play up to the customers, the depressing surroundings made it hard to be anything more than grimly serious. Certainly the other women had been strictly businesslike in their interactions. Maybe it would be easier to smile if the potential clients did first, he thought. Not, so far at any rate, that there seemed much chance of that.

As it happened though, and before he could bring himself to do anything different, he found a taker. A grey-haired man, perhaps in his fifties and wearing a coat despite the warmth of the evening, nodded his assent and asked: "Where?"

With a mixture of both relief and dread coursing through him, Ryan led the customer towards the dilapidated house that Steve had indicated earlier. Glancing at the pimp as he walked past, Ryan saw a flickering sneer that, once again, could have meant anything.

He was just starting to push open the door to what he assumed was the bedroom when he became aware of a grunting noise within. Peering around the doorframe, he had a quick glimpse of one of the women (Suri?) straddling a man who was flat on his back on a mattress that seemed to be the room's only item of furniture. She had her back to him and neither she nor her client gave any sign they had noticed the brief intrusion.

Ryan crossed to another open door across the hallway. There was nothing inside except a table. Ryan hesitated. A set of rickety stairs ran up to another level, but he didn't want to risk them - and all the other doors off the hall were not only shut, but had rubbish piled in front of them.

For a moment he thought about going outside to ask Steve what to do. But that really didn't seem like a good idea.

To his surprise, however, the grey-haired man walked past him into the room with the table, then looked expectantly at Ryan. The novice streetwalker blinked, then followed him in and closed the door. He had been in here before, it seemed.

"What's your name sweetie?" asked the man. He had a cultured voice that belied his rumpled appearance.

"Uh, Mandy ... sir."

The client gave a thin smile. "Your first time at this Mandy?" he asked, undoing his belt and simultaneously pointing to the floor in front of him.

Ryan knelt down obediently, pondering as he did so what to say in response. "Um, yes, kind of?"

He watched as the man dropped his pants and drew out a smallish cock that was already semi-hard, but stiffened appreciably as Ryan reached up to hold it. "Lucky me," said the client, his grin broadening as the city's newest street hooker started fondling and kissing his equipment.

Ryan was just about to open his mouth to engulf the now fully erect shaft when a thought that had been nagging away at him managed to garner his attention. Hesitating, he reached down to his purse and pulled out a condom.

He had not asked any of the clients at the club to protect themselves (or him), before giving them blowjobs. The first man had indeed insisted that Ryan not wear one, as part of the return for the outrageously high price he was being charged. After that, Ryan had forgotten even to look to see whether there were any condoms he could ask his clients to put on.

On reflection, however, it had occurred to him that he was being unnecessarily cavalier with both his own health and that of the men he was so intimately servicing. He wasn't sure whether the sick feeling in his stomach stemmed from anxiety, the weight of so much ingested sperm, or the onset of some illness. Whatever the explanation, it didn't seem like a good idea to keep taking a chance, especially when he'd been supplied with the necessary prophylactics.

Fortunately, the grey-haired man didn't seem at all put out by the idea of having to use a condom. Ryan briefly thought of trying to roll it on with his mouth, the way he'd seen some escorts do, but realised that was something he'd need to practise first to get right. So he put it on as swiftly and efficiently as he could and then got on with the more familiar job of fellating his customer.

The lubricant on the condom turned out to have some kind of fruit flavour, which almost but not quite masked the chemical taste of the rubber. Ryan had now had enough different types of phallus in his mouth not to be disconcerted by yet another new texture - a dispiriting discovery, if ever there was one. But he pressed on and was rewarded by a series of appreciative groans from above him.

It was only after he had been sucking away for several minutes that he remembered he was supposed to be on a clock. Shit, the timer! He had totally forgotten to use it. But Steve, he was pretty sure, would be keeping track of the time that had passed since he entered the house.

Relinquishing the swollen organ in his mouth he clambered to his feet and looked at the client. "Where do you want me?" he forced himself to ask. "Up against the wall or ...?"

"Over the table," panted the man, as he kicked off the pants that had been around his ankles. All trace of a smile was gone now. He was sweaty and lust-ridden.

With a covert sigh, which he took care to conceal, Ryan pulled down his g-string, lifted up his short skirt and folded forward over the laminated table top. Reaching round behind him, he made sure the convenient hole in the back of his fishnets was positioned correctly, then smeared some lube onto and inside his exposed asshole.

He tried to bring himself to urge the man to fuck him, but simply couldn't do it. The words were stuck in his throat. So instead he just wiggled his butt as invitingly as he could . The man needed no further invitation. Squeezing up against Ryan, he pushed his cock inside the sissy's puckered entrance.

The feeling of being penetrated was nothing new. Ryan had been fucked so often, not least by his former girlfriend, that he had almost come to regard it as normal to have his back passage filled and plundered.

And it wasn't as if the phallus that was now inside him was anything like as big as the monster dildos he'd had to endure. If it wasn't for the treatment he was regularly given at the Convent to strengthen and tighten his sphincter muscles, and to help his abused rectum to close up again after being violated for hours on end, his anus would have gaped so wide that the old man's cock wouldn't even have touched the sides.

And yet this was different. Because it was live flesh that was being injected into his ass, not plastic or rubber or whatever else the nuns chose to put in their strapons. And it wasn't a woman who was fucking him now, but a man.

Did it feel the same? Physically, yes, more or less. But psychologically, it was far removed from anything he'd previously experienced. For the second time that day, he was forced to confront the reality that he was having sex with someone who he still thought of as being the same gender.

In theory, oral sex should have been worse, because it was so much more intimate to take a cock in his mouth. And yet at least he had the sense that he was somehow in control when giving a blowjob. In his current position, by contrast, he was bent over a table with his rump in the air, the client's weight pressing down on him as the man began to thrust his eager cock into the greased hole that seemed so eager to accept it. All Ryan could do was lie there and let himself be fucked.

Except that wasn't quite true, was it? Because he could still play his part. He could be the whore that both the nuns and the pimp outside wanted him to be. That the man filling his rear with engorged flesh expected him to be.

And so rather than just passively accepting what was being done to him, Ryan started to push his butt back a little, endeavouring to meet each thrust so that the client's groin slapped a little harder against his plump buttocks, forcing the plunging dick a little deeper into him. He was doing it to speed up the sex act , he told himself. Anything to make it end sooner. Yet he also knew that he was programmed to behave this way.

His efforts were rewarded with a groan of appreciation from the man on top of him. And suddenly too, Ryan found his voice. Shakily at first, but then with growing confidence, even as he quailed inside at what he was saying, he began to urge the client to fuck him, to fill up his ass, to get deep inside him, to take him hard. Because he wanted the man's cum, needed it, was begging for it.

As the man increased his assault, Ryan felt a familiar feeling begin to grow. The stimulation of his prostate was causing him to get aroused. But he knew he could not reach an orgasm. Indeed he had not enjoyed true sexual release since his very first night at the Convent, when two gorgeous novices had twice made him explode with delight. All he could do now, after the diabolical treatment that had shrunken his male parts, was get to the brink of climax and then have it taken away.

For just a moment he thought of rebelling. Because this was insult piled on injury. To have to give pleasure to a man and not even have some of his own as compensation.

Yet he had come too far, committed too much, to give in to that impulse. So he accepted the feeling, rode with it, used it to fuel his demands for the old man to fuck him harder.

And as the moment came for his orgasm to stall and fade away, as he felt the familiar and pathetically small leakage of semen from his trapped and shrivelled organ, his groan of disappointment was drowned out by the client's ecstatic release. Although Ryan couldn't feel it, he knew that with each emphatic thrust the man was spurting inside him.

And just for a moment, there was a bizarre sense of satisfaction. That he had not just been able to cope with the experience, but had succeeded in giving the man the pleasure for which he was paying. Ryan had held up his end of the bargain, with the client, with Steve, with the Order. And having done it once, he could do it again ...

And he did, seven more times to be exact. Or eight if he counted the pair of guys who paid him more than double for a spit roast, then went to great care to time their orgasms so that one came in his ass mere seconds after the other had exploded in his mouth.

After very nearly allowing his first client to leave without paying - he broke out in a cold sweat every time he thought of what Steve might have done to him if he hadn't remembered just in time - he was more careful for the rest of his long night's shift.

But even so, not everything went right. The enthusiastic spit roaster who had finished off behind him, after taking a turn at fucking his mouth, had at some point lost his condom - or more likely slipped it off while Ryan was preoccupied with sucking his friend's cock.

The first Ryan knew about it was when he clambered wearily to his feet and felt the warm sperm running down his thighs. He had run out of wipes, so he used his discarded panties to stem the flow and then dry the wet spots on his fishnets and the mattress he had been using. Though in truth they were both already so stained that it was hard to see any improvement.

After ushering out the two raucous but apparently satisfied customers, he went back to his allotted spot on the street. It was only when a warm gust of breeze briefly lifted his skirt that he realised he had left his g-string in the derelict house. And he couldn't go look for it because Loretta had already headed there with another client.

By the time he was next able to check, with what turned out to be his last taker for the night, the panties had vanished. But in truth, he had already been feeling exposed and vulnerable with them on. Walking around without them didn't add appreciably to his anxiety.

What he most feared, he came to realise, was not the sex, nor even the potential violence that exuded from Steve like a wave, and which he also sensed in a couple of the clients.

Nor was it the ruined orgasms that accompanied every invasion of his accommodating ass, tough as they were to take. He wasn't sure if he'd been given something to make him more sensitive that day. It was impossible to know anyway, given all the hormones, vitamins and other pills that had become part of his daily routine. But he had certainly felt more turned on, something that made his hooker act simultaneously easier and more ignominious.

What really worried him was the prospect of being recognised by someone who knew him from his former life. He could tell himself that his former colleagues and acquaintances were no more likely to frequent this part of town than he himself had been. That the longer hair, the hormones and the collagen injections had changed him beyond all recognition - even before what had been done to him today to mar his feminine beauty.

But standing on a street corner, dressed and made up as he was, panties or no panties, he couldn't stop thinking about what even the most unlikely of encounters might mean. With every new passer-by, with each car that drove past, he felt a chill. Would this be the moment of discovery?

Strangely, it was not a feeling he'd experienced at the strip club, even though it seemed far more likely he could be recognised there. He could only put that down to the distraction of performing with Agnes, of doing what he could (after a serious wobble of his own beforehand) to stay as calm as possible and help her through the terrifying transition from nun in training to exotic dancer.