A - Degradation

 

They dragged me across to the window to confirm what they were saying. The sliding window opened on to a large balcony and, as they had said a grey building which seemed to be a school was clearly visible on the other side of the road, not more than thirty feet away. ‘Now, do you want the wig or would you rather face them as you are? Or would you like to tell us everything we want to know and save yourself all this?’ He was fitting the wig on my head, taking advantage of my indecision as I struggled to overcome the panic. I had seen from the reflection that I did look rather like a tarty sort of woman, the sort who would perhaps show herself off to the boys. If they put me out there dressed as I was, I would be a centre of attention almost immediately. But without the wig, I could also see that I looked like a man who would dress like this to show himself off, an exhibitionist transvestite. I wondered how long it would be before the morning break. Could I keep them talking at least until after then? I was still unwilling to give any more information than they had got from me already but what sort of choice were they offering me? Perhaps just a show of co-operation would be enough until I could screw up the courage to face the ordeal which they had prepared for me. I had to give them something to distract them, reveal and conceal, as I had before. And if it had to be the balcony, wouldn’t it be better to look as complete as possible rather than a freak?

So they got just a bit more from me. I kept them interested with another little tit-bit or two until the boys, hundreds of them, all between 12 and 18, had gone back into the building. I could see some of them sitting at desks at the windows at the same level. But B’s thugs were getting tired of my prevarications and without giving away a lot more than I could afford, I would have to suffer the degradation of going out on that balcony.

It was horrible - the worst thing they had done to me until then. They did release my wrists before they took me out there and they let me see how effective the disguise was. At least I might deceive the boys from that distance, provided that my private parts did not show under those skimpy knickers. They did let me try to hide myself away inside the knickers but it was obvious immediately that too much movement would return me to my original condition. And when they had got me outside, one of them told me that the woman who usually lived in the flat quite often showed herself off to the boys so that many of the older ones were in the habit of taking binoculars and telescopes to school with them. Then they left me there and locked the windows on me.

The balcony was about six feet deep and twenty feet long. They had locked both sets of windows but there was a small chair and a little coffee table with a jug of orange flavoured drink. As the morning passed, it got brighter and brighter on the balcony and, with the room behind me curtained and dark, the patio style sliding windows became mirrors. The first thing that I tried was to remove those boots so that I could walk more freely but the zips seemed to have been welded together. I did reach behind me to feel the fastenings of the skirt but even if I could have moved them, there was absolutely no sense in undoing it there. I could imagine the response from the boys just thirty feet away if I had removed any of these awful clothes while they were watching.

The balcony had a rail about waist high but only very light metal supports and no window boxes or anything else between the school windows and me. It was very difficult to walk at all in those extremely high heeled boots but sitting on the little chair was almost as bad. As I sat, that tiny skirt rode up my thighs. The chair was fixed to the wall behind it so that I had to sit facing the school windows. The table was even lower and fixed right in front of one of the sliding windows. Dressed as I was, with my private parts poised ready to fall out of the tiny knickers they had given me I was in danger of revealing the pretence with almost every movement. Sitting facing the school windows, I was aware of the need to keep my knees very firmly together to keep my secret. I did try sitting on the edge of the table but it was so low that the skirt went even higher up my thighs, revealing even more. And with the reflecting window, I couldn’t even risk sitting facing inwards.

I was still there when I heard the school bells ringing for lunch. Immediately there was a clamour as the boys burst out of their lessons. And almost immediately after that I was aware of the groups collecting at the windows in the rooms level with and above my balcony prison. I saw the glint of light reflecting from the glass of binoculars as they watched me, more and more of them with each passing minute. And when I stood up and walked to try the sliding doors, there was a shout of apparent disappointment followed by an even louder indication of their appreciation as I turned back after finding the windows still firmly closed against me. Their windows were opened and their voices were clearly audible, and not only to me, although I was obviously the target. When I sat down, there were oohs and invitations to show a bit more leg; when I stood up they cheered every step. And soon the balconies above me and to one side were also occupied - not by women who might have provided some distraction, but by large men in tee shirts and jeans, similarly enjoying their chance to study me. There was nowhere I could hide and they were so close. Although I hated to think of them looking at me as a woman, I was constantly expecting some indication that they suspected something else. I tried to make myself small, to keep my head down so that the hair of the wig covered my face. Sitting with my knees pressed tightly together and my ankles crossed was the only way that I could believe that they were not able to see up under my skirt. I tried to force myself to keep still, to blot out the surroundings, just as I had when they had been beating me about. That had seemed so much easier. Then the pain itself had been a sort of distraction. I had been able to focus my mind on one part of my body, to concentrate on overcoming the pain I felt there and then withdraw from their blows and questions. But now, all the time, there was the clamour from the boys. And to make sure that I didn’t just sit there, the fiends inside kept fiddling with the locks of the windows, letting me think that they were open so that I would have to get up and try them again, desperately seeking a way out of the humiliation they had forced on me. And of course, every movement was cheered appreciatively. I did not know how to get up from the chair without letting my legs open and revealing my knickers, with their contents balanced so precariously. With those unfamiliar heels it was very difficult to get up without jolting myself with the added risk of everything spilling out. I could only get off the balcony through the sliding windows and I wanted to get off so badly that I felt obliged to respond every time I heard them fiddling with the locks. So, inevitably, the knickers gave up the unequal struggle!

After about half an hour, I heard a change in their shouts. I thought that one of them must have suspected something about me because the shouts seemed to become questions rather than just invitations - ‘What’s in your knickers then? Why won’t you show us your chest? Where does your boyfriend put it?’ And I couldn’t really hear whether they were calling me Jenny or Jimmy. But I feared the worst and stood by the windows, begging to be let back inside. The boys’ shouts included phrases like ‘shut that door’ and I felt sure that they had worked out my secret. I wanted to get off that balcony and in the end I promised to tell them more if only they would let me back inside.

 

B - More success

 

I told them to get as much as they could from him but to be sure to get him out on the balcony at lunch time. Gloria had given the boys a leg show the day before and I had arranged for several of the older ones to get gifts of binoculars when they arrived at school that morning. To make sure, I put several of my lads in the flats above and next door to reinforce the goldfish bowl effect. It worked wonderfully. He was begging to be let back inside before the end of lunch time, promising to give us a bit more. Because we let him in before the end of the boys’ break with the constant threat that we could put him back outside again,, he did tell us just a bit more. And we still had the afternoon break, not to mention the end of school.

Just before the afternoon break we put him out with a knock out drop and then put him back out on the balcony. But this time we unbuttoned his blouse so that his black leather bra’ was clearly visible and hitched his skirt up his legs, above his stocking tops. The boys put him out on the chair with his legs up on the table, one leg bent and the other out straight so that the red lacy slip was clearly visible, with just a hint of the white knickers showing, although they did give him the benefit of hiding the more secret part of him again. In the morning, the slip and knickers had been tucked under the waist band of the skirt but for the afternoon session, they made sure that the skirt did not hold either garment at all! So when the afternoon break started, just about every kid in the school was watching him and their comments were pretty ripe. And of course, they made enough noise to wake him.

 

A - Complete humiliation

 

I came too to find myself back on that balcony with the cheers and ribald shouts of those boys ringing around me. My blouse had been unbuttoned and my skirt pushed right up my legs. I couldn’t get it down without standing up so it took just a bit too long for comfort to make myself look less provocative. I rushed to the windows to see if I was locked out on the balcony and felt the first window being locked as I tried to open it. But the gorilla who locked it indicated that the other one was open. So I teetered along the balcony to the other door. And as I walked just that few yards I felt the slip and knickers sliding down my legs. The cheer from those boys as I staggered back into the room with my knickers round my ankles and the slip just about to join them was something I never want to hear again.

 

I was so ashamed and humiliated, even more by my feeble reaction. Although I did regain some composure later, I know that I gave them even more clues in my anxiety not to be put out on the balcony again. So I kept feeding them ‘nearly true’ answers until the school was completely empty. They kept telling me how much the boys were going to enjoy my next performance - they had already seen my knickers so they would expect something better. Perhaps just a bra’ and knickers and a transparent negligee? Or even a bondage pose? Yes, they agreed. Next time it would be very pretty underwear and a very full skirt - the weather forecast was for strong breezes - and I could be tied standing near the edge of the balcony. The wind always seemed to gust upwards round that balcony.

They seemed to have some sort of hot-line to B, checking every extra scrap I let slip, promising, threatening, greater humiliations from then on unless I co-operated. As time went by, and the memory of the day’s humiliation faded a little, I tried to obfuscate again, giving them false information which I knew would be very difficult to check, hoping to gain some respite by appearing to co-operate without giving too much away. There was something unconvincing about their threats - surely someone would investigate a woman being locked out on a balcony, or a transvestite exhibiting himself to a whole school full of boys. I had started to hope again, an emotion which B has taken great pains to obliterate. By about seven o’clock in the evening, one of them held me while the other gave me another jab and I passed out again.

 

B - Diversion

 

That day reinforced my certainty that we had found exactly the right way to deal with him. If it hadn’t been that it would have been something else - we would have found his weakest spot eventually. But I decided that the balcony was too risky - boys will talk and I didn’t want anyone taking too much notice. A lot of gossip about a bloke showing himself off to hundreds of boys would soon have come to the attention of the police, social workers, or worse still other newspaper reporters. This had to be handled discreetly, even if he had to think the opposite. So we moved him to another venue. And he had given us a lot of information, had given every impression of co-operating.

So I was not at all pleased when I found out what a wild goose chase he had created for us. He was going to pay for that and Harry suggested the perfect punishment - a short trip to Amsterdam.

 

A - The Cathouse

 

My fabrications earned me a few days respite from their attentions, although they still wouldn’t let me have proper clothes - they said it was skirts and dresses or nothing so naturally I chose to remain naked. But I was going to be made to regret deceiving him.

It was clear that he was furious when he found out how much time I had wasted. He was shouting and threatening, telling me that he would get even as well as getting the truth. And while he ranted, one of the guards seemed to have an idea, an idea which obviously appealed to all of them. The next morning, I found myself immobilised on a hospital type trolley being loaded aboard an air ambulance. We had been in the air for about half an hour when I got another jab and passed out again.

When I next became aware of my surroundings I was fully dressed again. But this time I was dressed as a whore. Black fishnet stockings, a black skirt with a slit which reached right up my thigh, a bright red short sleeved blouse and a short fluffy blonde wig. I was tied in a chair in front of a set of mirrors so I could see exactly what they had done to me. Extreme make-up and ultra-high heels. The blouse was almost transparent and I could see the black and red bra’ around my chest and the short skirt had been pushed up almost to the tops of the stockings, revealing the red slip with its black lace edging. As I struggled against the ropes holding me to the chair, the black and red knickers were clearly visible. I could feel that my private parts were securely held between my legs, my penis pulled back between my legs underneath me, so this time there seemed no danger that I would ‘fall out’. And Harry, one of my tormentors, explained what was going to happen next. It was my own fault for telling such lies, he said.

I had been transported to a brothel in Amsterdam, they told me. I had been dressed like this to encourage the customers. The thought that they might find ‘customers’ for me filled me with horror and it was as much as I could do to disguise those feelings so that they didn’t guess. They gave me a while to get used to what they had done and then came their ‘coup de grace’ - I was going to be put in the display window for all the filthy perverts in the street to see. I would have to sit on a stool in front of the window and attract customers for the girls. But if one of the clients wanted sex with a man instead, well, I would be the only man available. It was just up to me to look exactly like a woman so that none of the clients even suspected. And just to make sure that I really tried to attract their customers, I was given a target. Unless I attracted at least the average number of clients each hour, they would remove an item of clothing.

They did give me a little time to get used to the idea. And they made it quite plain that it wasn’t information they wanted this time - B wanted me to suffer. I was introduced to the working girls who had been told that I was a transvestite who enjoyed being forced to dress as a whore. They giggled and teased and were particularly amused when they learned that I was going to relieve them of the need to sit in the window. It seemed that they all hated that more than providing the service they were employed for. So they made me parade for them in those awful heels, trying to encourage me to wiggle my bottom as I walked, grabbing at the hem of my skirt and lifting it so that they could see more of my knickers. Before I was put into the window, I was thoroughly inspected, my make-up adjusted until they were sure that I would generate the right image, encourage the right clients. And one of them, who seemed rather more sympathetic than the others, spent several minutes instructing me in the most successful poses.

 

It started in the late afternoon. I was made to sit on a stool in the alcove in front of the window when the drapes were drawn back and the girls were ready for work. It was like an old fashioned shop window, a sort of raised platform surrounded by a high partition draped with deep red curtains. Once I had been set up on the stool, the entrance to the alcove had been closed, and it sounded as if it has also been locked. I realised that as I sat on the stool, the skirt was gently sliding open, the slit revealing more and more of my leg. Every few minutes, I was obliged to hitch it back again in case my personal secret was revealed as well as the knickers. At first the street was quiet - just a few men passing, mostly taking little interest in me. But the Madame was not going to be satisfied unless I attracted at least her usual volume of custom - and let me know it through the partition. She instructed me to get off the stool and try walking about. ‘And let them see a bit of leg, you’re supposed to be an advertisement, not a deterrent.’ I got down off the stool as she instructed and took a few short steps, trying to maintain my balance on those extreme heels, trying to remember to swing my hips as I had been told. I had to maintain the illusion - the last thing I wanted was to be recognised as an imposter. I turned back to the stool and tried to sit elegantly, without revealing more than I wanted. I was aware of the quickening tempo of the street as the afternoon wore on. A man stopped in front of the window. I felt his eyes all over me. I knew that I had to encourage him to come inside, that the Madame would at least expect me to smile. It must have looked hideous, that nervous grimace which was all I could manage. But he stayed in front of the window and gestured at me to get up and stand closer to him. He was already so close, just the glass and a few feet between us. Somehow I made myself obey his instruction and stood in front of him. His face was level with my waist and he gestured again - he wanted me to hold my breasts. I forced myself to let my hands stroke up from my waist towards them, as the girls had instructed me, feeling the soft bouncy padding inside the brassiere. The action made me more than ever aware of the artificial nails which had been glued over my own, long and scarlet. And I was rewarded. I saw him turn and approach the door, heard the Madame welcome him as he entered and then direct one of the girls to attend to him. And soon there was another one. I had to pose and strut, feeling more exposed than if I were naked, knowing that I was just an exhibit but also aware that I had to keep up the illusion. I was so aware of the leers of the passing men. Groups of them would cluster round the window, pointing and sniggering. I managed to keep to the target they had set me for the first hour but the target for the next hour was higher. Again, I managed to reach the number but the third hour was a disaster; at least they told me that was and that the girls were almost idle. So, in the window, with men watching, the Madame and one of the bigger girls came into the window and dragged the slip from under the skirt. “Next time it will be the knickers. After that we start on the outer clothes!”

 

The evening was worse. They took me back inside and dressed me in a very short leather skirt and a leather bustier. Then they fixed leather cuffs round my wrists and ankles and chained me up very close to the glass, facing the window. My legs and arms were spread wide so that I could hardly move. I didn’t dare to move anyway fearing that the artificial boobs would slip out from the bustier and reveal me as the imposter I was. And right in front of me, men were staring, pointing, making ribald remarks about me to each other, considering what they would do to me if they came in. It was shaming and frightening. It was my punishment for having misled him and I wondered how far he would take it. Would he really let them rape me as well?

I had to stand there for hours. The men in the street hovered in front of me, enjoying the sight and taking advantage of my inability to avoid their stares. I had to move sometimes to relieve the cramps in my arms and legs and every struggle was watched appreciatively by the men outside. But the pose was obviously successful since a steady stream of clients came through the door, to be welcomed by the Madame and allocated to one or other of the girls.

They did allow me a short respite around midnight. A chance to stretch my aching limbs and rub some life back into my hands, as well a very light salad with a glass of water. But then they prepareed me for my next ordeal. My clothes were changed again. I was not allowed to see exactly how they dressed me - I was blindfolded while they worked - but they told me, and gave me some idea by showing me my reflection when they were finished. This time I was to be almost fully dressed. A white bra’ and suspender belt and white knickers, although I was not allowed to see them until later. Pale tan stockings and white, high heeled sandals. They hd fixed a new set of artificial breasts to my chest which fitted over my shoulders and up to my neck. The join between them and my neck was covered with a black velvet choker which supported a large pearl at the front. The light cotton blouse had a scoop neckline which displayed the cleavage of the large false breasts and the darker coloured, prominent nipples were not disguised by the underwired bra’. The skirt was bright red but very light and I could see the lace edging of the light slip beneath it. They replaced the wig with another, with longer, darker, hair and retouched the make-up before letting me see the effect. I must confess that the effect was startling - I really did look like a rather well-endowed young woman, dressed for a summer day but willing to display some of her charms; her ample breasts in particular.

I would have to perform in the window again. But this time I had different and at first incomprehensible instructions. Apparently there were two photo-electric beams just above the level of my head and at least once every two minutes I would have to break the beams with my hands. Every time I failed to break the beams would mean another hour in the window. If I performed adequately, I could be out of the window by two o’clock, but they could leave me there all night - and the next day. They gave me these instructions actually in the window, showing me where the beams were and stressing the importance of breaking both beams at once. I realised that the whole procedure was designed to ensure that I raised my arms above my head while standing in a particular part of the window but I did not guess their purpose until I had been in the window for several minutes.

To begin with, it was easy. I had to stand, since they had removed the stool, but I was free from the straps and chains and I was dressed more decently than before. But as I walked about the window I became aware of the crowd of men gathering outside. They were crowded round the window with their noses pressed to the glass, clearly anticipating something which I had no knowledge of. I paraded for them, going through the performance as I had been instructed, unable to guess the cause of their excitement although it clearly involved me. I followed my instructions as closely as I was able, even standing in the middle of the window every few moments and raising my hands to break those beams. I suppose I had been there for about five minutes before I heard a switch being thrown and was aware of the low hum of an electric motor. But there was nothing else and I didn’t discover its purpose for another few minutes.

It was very sudden when it happened. I was standing near the middle of the window when there was a sudden updraught of air. The light skirt and slip were almost instantly swept up above my waist, to the delight and approval of the crowd of men outside the window. As soon as I realised what was happening, I struggled to hold it down, managing at least to keep the front down by pressing my hands against my thighs. Then I realised that the mirror at the back of the window would give a perfect view from behind and I tried to control the skirt with one hand at the front and one at the back. That was when I heard the Madame telling me that the only way to switch off the fan was by breaking both beams. Eventually I managed to force myself to abandon the struggle to control the skirt and reach up to break the beams. As soon as I raised my hands, the skirt and slip flew up around my face. I panicked and pushed it down again but knew that I would have to try again. The next attempt was a little more serious but although I broke the beams for an instant before renewing the struggle with the skirt, it did not switch off the fans. I needed to hold my hands in the beams for at least five seconds before the fans switched off. And in that time, the skirt sailed high above my waist, revealing all my secrets to the men crowded around the window. I could hear their delighted shouts of approval and their coarse comments and felt myself blushing scarlet with shame at having to give them sucha display. Not only was I shamed by having to give them this display but I guessed that there would soon be a demand for the services of the ‘man in the window’. Surely with all my underwear exposed and swept up by the draught, the men outside would see me for what I was. I have always despised homosexuals; they make me feel sick. The possibility of being molested by one of them appalled me. But I had become convinced that that was the purpose of this exercise - to make me reveal myself as a man dressed as a woman to attract a sexual partner. It seemed only a matter of time before I would be taken from the window and forced to submit to such an unspeakable experience.

 

In the end, I was left in the window for only about half an hour. But I was so nauseated by the prospect of what would be in store for me when I was taken out that I was actually reluctant to leave. In the event, my fears were unfounded. None of the men outside had demanded sex with the transvestite prostitute exposing himself in the window; and when I was able to inspect their handiwork more closely, I could understand why. I stood in front of a mirror and lifted the skirt up to my waist. If I had been willing to risk turning my back on the spectators while I had been in the window, I might have understood before, by seeing what I now saw in the mirror there. But I knew that I wouldn’t be able to position myself to break the beams in that position. So I was astounded by what I saw. The constraints that held my private parts so firmly were shaped on the outside to resemble those of a woman. The knickers were almost non-existent; just a slight hint of white lace covering, but not concealing, a little bush of imitation pubic hair and the outer shape of a woman’s pussy. From even a short distance, the effect was absolutely realistic. Had I known how perfect the disguise was in advance, I would have felt more secure in my imitation. But that was not part of their plan.

 

B - Another blow

 

That Amsterdam trip only lasted a couple of days but he realised that we were serious. He was very contrite when he got back although I was sure that he was still keeping something back. Even so, we were nearly there. The boys who had taken him, and been with him while Margret had used him, told me about his experience there and gave me another clue about him. They hadn’t been able to understand why he would be reluctant to leave the window - they even suggested that he was enjoying himself, but I guessed differently. I had almost decided what I would do with him when I had finally got everything out of him and that news added extra spice to the idea which had been forming in my mind. It would take quite a lot of time and I wanted to be sure that we had got all that he knew before then. He had already let slip that he could do nothing to hurt us for at least three months, and had confirmed this in so many ways that it seemed fairly safe to rely on it. So I had to work fast but also be patient. The next stage would just be temporary but it would be as convincing as we could make it. Getting hold of the drugs and pills was fairly easy but it would take a little while to wear down and rearrange that muscle - we didn’t want him too strong for the next stage. Keeping him half sedated most of the time and controlling his diet while preventing him from getting exercise was enough to weaken him for the next stage. And we could do a bit more than just shave his eyebrows! Margret’s devices could be refined a little. This bit was going to be expensive but I had too much at stake to worry about that. I was going to win.

 

A - More humiliation

 

I was moved back to the mansion and then seemed to spend many days drifting in and out of consciousness. I was always in a bed when I did become conscious although I am sure that the bed and the room itself changed several times. I was never sufficiently in charge of my faculties to move, to get out of the bed or even to eat independently, although I do remember being given slops and drinks. Several times I was aware of being connected to tubes and machines. I had strange dreams although I cannot remember being questioned again. I am sure that I was still sufficiently in charge of myself at least to have remembered; and I remember reminding myself every time I came round to tell them only what I had already given them. Even in my dreamy state, I was able to think up some ideas that might distract them when they started again. That at least seemed certain - they would start again. I had to be strong, stronger than I had been until now. I couldn’t afford to give them anything more.

I seemed to come out of that state very slowly, only half aware of my surroundings as the world I could see became steadier. I was aware of changes although it took me longer to work out what had happened that it takes to record. I was no longer naked but my skin was smooth and hairless. Fixed to my chest were two plastic breasts while my manhood was cramped up between my legs somehow. I was wearing a tiny pair of pink knickers and a ‘baby doll’ night-dress top. And somehow, those tiny knickers were able to conceal all the male parts of me, parts which had never been so constrained before, even during that trip to Amsterdam. My face had also been expertly shaved because I did not have my usual morning stubble. Trying to pull the boobs off my chest was useless and painful, they were glued somehow which felt very permanent. And I could not work out how to release my parts from the strapping which seemed to hold me so securely inside those knickers . Not only could I not work out how I was fixed but I found that my fingers were considerably less useful than usual - each one ended in a long scarlet nail, either my own painted or something artificial glued on. I wanted to get out of the bed and strip the whole collection off but before I could properly control my movements, a woman came into the room. I shrank under the bedclothes to hide myself from her but she was determined and persistent. Not only that but I saw that she was accompanied by another woman and a large man.