Lisa's Contract

by 2Sheds

  

Michael woke up slowly as the effects of the drugs wore off. The mist in his head gradually cleared and he was able to start to assess his situation. So this was it. This was real. It was happening.

Michael was slumped on an old crate leaning against a wall in an empty, derelict building. Something industrial, damp and cold with gaping holes where the windows and doors once were and only the skeletal remains of a roof. The light was fading fast, so Michael guessed it was somewhere around 7 or 8 p.m.

It only took Michael a couple of seconds to take in his surroundings, but he spent considerably longer investigating his personal state. His legs were clad in shiny black boots right up to his thighs with super high spiked heels. They were stunningly sexy and the leather creaked appealingly as Michael stretched out his legs. On checking further Michael found that he was wearing sheer black hold-up stockings beneath his boots and a black pvc minidress which barely covered their tops. Alerted by the constriction in his breathing he found that beneath the dress he was encased in a horribly tight corset, the upper part of which formed an impressive fake bust. Michaels shallow breathing quickened with both excitement and forced restriction as he reached up with his pvc opera-gloved hands to find out what had happened to his hair. Without the benefit of a mirror he could only tell that it was thick, black and seemingly cut into a neat bob. With an experimental tug he found that it was quite firmly fixed to his head. The final adornment was a black leather and metal collar fitted snugly around his throat.

For a little while Michael simply enjoyed the excitement of wearing such an outrageous and daring outfit. He had tinkered with some cross dressing before but never so completely and so well. He imagined himself looking utterly stunning and found himself becoming aroused. This feeling was brief however as he became aware of the painful constriction of his cock which had been firmly and tightly strapped down and between his legs.

The only other thing in Michaels possession was a small shoulder bag which he now investigated. In it was an envelope marked 'Lisa'. Looking around him again and establishing that he was utterly alone, Michael opened the envelope.

Michael had led a relatively non-privileged life until the last year or so. A combination of good investments, a handsome inheritance and a lucky lottery win had then made him extremely rich and yet strangely unfulfilled. He had lived well with his money, buying cars, clothes and property and yet still not finding real satisfaction. Relationships had never worked before he was rich and they didn't work now. Ultimately Michael was driven by his darker perversions and desires. As time passed he became more and more consumed with the idea of living out his fantasies in real life. They were elaborate, degrading fantasies and now, finally with the help of his money, he had set them in motion. He had spent months arranging this with a shadowy group he discovered on the internet. The idea of all this coming to reality both terrified and thrilled him.

This morning Michael had taken a walk, for no particular reason other than that he was bored. He had pretty much given up hope of the promised 'event' ever happening and was already mentally writing off the money he had spent. As he walked out of the village and down towards the river he barely noticed the white van come past him, you saw those all of the time and several people in the village had them. This time however, the van came to a sudden halt right along side him as the side door slid open. Two pair of strong arms heaved roughly off his feet and into the van. The door slid shut and the van sped away. From that point Michael knew nothing at all, save some disturbed disjointed dreams. Only now was he awake and fully conscious of what had happened to him; feminised and about to take part in an ordeal that in part at least, was of his own making. He read the letter.

"Your name is Lisa. You will notice that we have given you a rather striking outfit for your little adventure. There are no escapes, no safewords, you do exactly what you are ordered to do or you will find your cosy spoilt little life is never returned to you. You may not have noticed some of the features of your clothing. The zippers on your rather lovely boots have been soldered closed. The only way out will be to cut them off. The corset that is giving you that lovely hourglass is also locked on - there are thin metal bands sewn into the fabric of it and again, soldered shut. Your wig is glued on quite strongly, and will not come off without treatment with the solvent in our posession. Your own hair has been removed. The long gloves you are wearing have also been glued on."

"You may or may not have noticed yet that your lips have been nicely plumped up with collagen shots and you have had botox injections...", Michaels hands flew to his face as he read this, though he couldn't feel too much through the pvc gloves, "...to calm your expression. The collar cannot be removed of course."

"So Lisa, to your insructions. On the wall near the door, a rough map has been scratched. This marks the spot you are to go to next. When you reach the place marked X on the map, enter through the yellow door and look for instructions. Don't take too long."

And that was it. No more instruction than that. Suddenly Michael felt extremely alone and vulnerable. He realised he had been struggling to read the end of the letter as the daylight had almost gone completely. He had no idea where he was or what was in store for him. He had deliberately been very non-specific in his suggestions and scenarios and was starting to wish he had built in a few more safeguards for himself. Michael hurried over to the main door to the wrecked building, discovering as he did just how impossibly high his boot heels were. They must have been 5 inches and easily the highest he had walked in before. Once he reached the sketch map scratched onto the wall his concern mounted. His destination looked to be a long way off, with many turns and crossroads to negotiate, and it would all be from memory! He had no means of writing down the directions so he had to concentrate hard on the map while there was still enough light.

Micheal was shaking with nerves and the chill of the approaching night. It was sinking in to him just how real this was. He had to go out into the world and walk the streets dressed like this! He had crossdressed for pleasure several times but always alone and in private, and certainly never as outrageously as this. He was as conspicuous as it was possible to be outside of a fetish club.

With teetering, nervy steps, 'Lisa' set out into the dark.

As he had already figured, Michael was in a heavily industrial area of what he imagined was a large city. From the sounds drifting across the night air and distant glow of lights he could tell it wasn't all as derelict and disused as the place he had just left. His concentration was split between remembering his route and managing to walk at all in his boots. As he went he tried to adapt his walk to a more feminine gait, shorter strides, one foot in front of the other, rolling his hips. He found this made the heels easier to manage, though still challenging enough.

Exiting the abandoned factory complex he found himself on an empty road, lined with small industrial units and warehouses. It was dimly lit and eerily quiet. Michael allowed himself the brief hope that maybe the route had been devised to take him only through areas deserted at night. That thought was shortlived however as he became aware of the distant sound of a heavy truck getting louder behind him. Oh God, thought Michael, this is it: the first public sighting of Lisa! The truck did indeed slow down as it passed, the driver leering out of the window with a certain amount of disbelief before continuing on. Michael could hardly breathe inside his tight corset as his heart pounded almost audibly.

From that point Michael started to find it easier. He concentrated on his route and kept walking. He figured that he was much safer if he really pulled the look off and actually convinced as a female rather than look like a man in a dress. Most regular working guys would happily sound their truck horns or shout a few obscenities at a woman and then carry on their way, but he didn't want to find out what they might do to a man dressed the way he was.

Truckers were one thing, but Michael soon faced a new challenge. He reached a major road junction that marked the end of the industrial zone. There was a four lane express road across his path with a bridge over it. Once he had crossed this he would be in what looked like a seriously run down commercial and residential zone. Michael's stomach did flips as he tried to remember what came next. He would need to take a right, walk two blocks, left, then right again, take an underpass beneath another big road and keep going for two more blocks. His feet and legs were killing him already and breathing was getting harder. He pressed on.

There were a lot more cars now. Not exactly bustling, but more than enough for comfort. This was not a good neighbourhood, and some of the comments he was getting were pretty nasty. Luckily, if not amazingly, nobody seemed to foil his disguise. He seemed to be convicing as a woman, albeit some kind of slutty fetish whore. A lot of the comments were actually quite appreciative. Michael was very aware that the poor quality of the streetlights around here were being very kind to him. There was one moment of panic when he saw a gang of waster street kids ambling towards him. He knew he would be in for trouble if they saw him so he dived into an alleyway and hid behind a dumpster until they had long passed.

It seemed like forever before he finally reached his destination. The relief he felt in not screwing up his directions didn't make up for the pain in his legs and chest. The 'X' on the map had led him to a shabby parade of small stores. Next to a closed up hardware store was a yellow painted door. Michael checked again and there was definitely only one yellow door. He pushed it, and it swung open into a gloomy stairwell. This would be the apartment above the hardware store, he supposed. He found the light switch which dimly illuminated the stairs. After his lengthy march, climbing the staircase in his killer heels was just one more piece of agony.

The apartment was small, dirty and gloomy, and sparsely furnished. There was a bed, a couple of chairs, a locked closet and a dressing table with a large mirror and a phone. A door led through to a tiny galley kitchen and a small bathroom beyond that. Michael was exhausted, hot and sweaty beneath all that black plastic and the thick wig, but even so the mirror caught his attention immediately. At last he was able to properly see what the looked like and he was impressed. The clothes were tight fitting and stunning, the collar looked quite elegant in a fetishy way, his hair looked absolutely natural. What really surprised Michael was his face. It was still him, he knew that, but the make up, the botox and the full cherry red pumped-up lips had softened and shifted his features into those of a quite passable and striking female. He was not surprised that nobody had seemed to guess his secret at first glance so far. He was naturally of a slim to medium build anyway which had obviously helped, he reckoned that even in these heels he was probably a whisker under 6 feet tall.

Micheal eased himself down onto a chair in front of the mirror and scrutinised himself more closely. Now he was indoors and in private, he was able to once again enjoy the feeling of transformation that he had undergone. His face was really flawless, though perhaps a little touch up of powder might be needed. His eyes were another triumph. Michael had never attempted proper eye make up, or really bothered a lot about make up at all in his previous dressing sessions, so to see his dark eyes set off so beautifully was really something. He was quite in awe of himself - exactly the picture of femininity he had hoped he might achieve. That was only part of it though, and Michael knew that these looks could be achieved far more easily and far cheaper than this 'adventure' had cost. Looking around he saw two envelopes on the bed marked with a simple '1' and '2'.

Opening envelope one, Michael found another letter. With heart quickening he read.

"So Lisa, if you are reading this then it seems that you are still in the game and haven't got yourself hopelessy lost. The delightful little slum you find yourself in is your home for the night. We hope you will be comfortable.

For now, Lisa, you are our whore, and like any other whore you are expected to pay your way." Michael gulped as he read this. His imagination already way ahead.

"The rent for your apartment is £100, payable to the landlord when he pays a visit later on. He works very late. If you do not pay him then you do not get your next instructions and we disappear. I really don't think you want to be left in that state all alone, lost and homeless do you? There is make up in the dresser draw for you to fix yourself up when needed. There is some food in the kitchen if you need it. You may have already discovered that the phone takes incoming calls only. Open the next envelope Lisa, and enjoy your evening."

Michael was in turmoil. This was already sounding much more serious than he had bargained for. Reality was so much more scary than fantasy. He opened up the next envelope and gasped at the contents. There were four postcards and a slip of paper. The postcards were all the same, showing Michael in his full outfit pouting lustilly at the camera. When did they take this? He had absolutely no recollection of it. More horrifying was the text emblazoned on the card which read simply 'TV COCKSUCKER LISA' and then across the bottom of the card 'CALL ME' and a phone number. The slip of paper gave him instructions to go out right now and put these cards up in the four nearest call boxes and start earning some rent. That was it, no further help or instruction. Michael was beside himself. He remained frozen to the spot for some minutes stuggling to decide what to do. He wanted out, but how? He had no way contact these people, no way to beg for an end to the game. Another part of him was deeply aroused, the fantasy part of his brain telling him that this was exactly what he had dreamed of.

In a daze, Michael got to his sore feet and went outside. It was easy to locate the call boxes, which were in two sets of two about 100 yards apart on the road. He felt horribly dirty and ashamed just putting up those cards, but what really terrified him was what would happen next. Fantasies aside, Michael had never been anywhere near another man's cock. As soon as he had put up the cards, he hurried back to the apartment to wait. Unseen by him outside, a shadowy figure slipped into each booth in turn and removed the cards.

Michael sat in the dirty little apartment and waited with increasing desperation at his plight. His thoughts were veering wildly between thrilled elation at being placed in exactly the helpless situation he had so often deamed of, and the quaking fear of reality. When the telephone started to ring he almost jumped right out of his skin.

For several seconds Michael stared at the phone as if it was a homicidal alien. Finally he swallowed hard and picked up the receiver. He had no script for this, no idea what to say at all. Fortunately, the voice on the other end took the initiative and didn't seem remotely interested in small talk,

"How much for full oral?" was all the roughly spoken man said. Michael had no idea what the price should be for this, but hoped that maybe the rules of the task we a good enough clue and after some hesitation replied,

"A hundred for full oral," Michael was trying to sound as softly spoken and feminine as he could, hiding his fear behind the character of Lisa.

"You have got to be fucking kidding me!" The caller said in mocking disbelief, "I'll go to thirty IF you are real good. Deal?"

Micheal reluctantly agreed the deal and gave him directions to the yellow door beside the hardware store and the brief conversation ended. So this was going to be it; the loss of Michael's cocksucking viginity.

It was just a few short minutes later when Michael heard the foosteps on the stairs. He had no idea how he was supposed to handle this so he was just going to have to play it how he saw it. His feet were killing him, his hands and feet were hot and sweaty from their confinement and his head itched from the thick, lustrous wig. The corset seemed much less of a problem now he was used to it and not trekking across a city. When he let the guy into the room he could hardly speak except to say hello.

Sensing the awkwardness of the greeting the guy took a long look at Micheal, "Well Lisa, it looks like you are pretty new to this huh? Do you really think you are worth thirty of my hard earned? I gotta tell you though, that is one serious outfit." He stood back and took a long, lingering look at the tv whore before him. For his part, Michael tried to look as stiking and elegant as possible. Reluctantly he did admit that he was pretty new to this.

"Well all I can say Lisa is that you had better be good and give me my money's worth. You can call me Jim. Now how about I sit over here and you get down on all fours and crawl over to me real slow like you really mean it."

Jim sat on one of the chairs, with his legs apart and a visible bulge growing in his pants. Micheal spent a long minute preparing himself. He imagined it was like the frozen, fearful moment before leaping off a bridge on a bungee rope. Jim goaded him on again and Michael acted, getting himself down on the floor on all fours. Slowly he began to crawl across the room, obeying Jim's command to look him in the face as he went. Michael was moving slowly and sexily, his ass swaying seductively. This effect was more down to his reluctance to reach his destination and the tightness of the corset than any porn acting ability. Jim was appreciative,

"Ohhh yeah baby...crawl over here to Daddy," he rubbed at himself, his prick straining against pants, "Come over here and get what you want."

At length, Michael found himself between Jim's knees, reaching up and fumbling with his pants. The damn gloves made this really tricky, but eventually he freed the thick, solid cock from it's prison. Without letting himself think too hard about it, Michael parted his plump lips and slid them over the sweaty head. He sank his head slowly down the shaft, using his tongue, gripping the base with his gloved hand. That was it... he was a cocksucker. Jim moaned his approval and muttered instructions, making him go faster, slower, more tongue, suck harder, it seemed to go on forever. Michael's jaw ached as he bobbed up and down on that thick prick, wondering how long he would have to endure this.

As his pleasure built, Jim took a fistful of Michael's hair and forced him to look him in the eye, telling him to work his prick faster with his fist,

"I'm gonna give you want you want slut, I'm gonna cum right in your slutty face just like you want huh? That what you want? TELL ME?"

Michael worked that prick faster and faster,

"Yes..please cum... please cum all over my slutty...AGGH!!!" Michael was cut short as a huge spurt of juice hit him right in the eye. Jim held his head firm by the hair as he unloaded in several splattering bursts over Michael's face, making his open his mouth to take the last aftershocks on his tongue.

And so Michael finally became Lisa the cocksucking whore. Her initiation was complete.

"That was pretty good Lisa. You get the full thirty for that. See ya." Jim was up and gone within a minute, satisfied. Michael was left kneeling in shock, the hot cum facial cooling on his face, watching the paper money float to the carpet. He knew he would have to do this three more times to make the money he needed, and wondered how much more he could take.

The next client was even more direct and a lot less pleasant. Michael would only ever remember him as 'the bastard' as he never gave a name. This guy wanted nothing more than to use Michael as a hole to dump his cum in. He had him kneel, then he took off his belt and used it to lash Michaels elbows together behind him, listening to no protest. He then stood in front of Michael, grabbed his head in both hands and face-fucked him. It was almost unendurable for Michael who gagged and choked as the bastard banged his throat. The more uncomfortable he was the better the guy liked it, hammering harder and yanking that wig so hard Michael was scared it would rip off. Eventually the bastard came hard in his throat, giving Michael no option but to swallow fast and hard to prevent himself choking or even drowning. The leering bastard then peeled off three notes from a huge wad of cash, and stuffed them one by one in Michael's abused mouth before retrieving his belt and leaving. Michael ignored several phone call after this, spending the time splashing his face with water and crying with shame. Eventually he was able to pull himself together enough to go and fix his make up as best he could, which would never be as immaculate as the job 'they' had done on him.

After the bastard, the job actually became a million times easier. Once you knew how bad in could be then any regular guy wanting a blow job seemed like a blessed relief. There were no horror stories with his next two clients, just a growing feeling of detachment and a sick, queasy feeling in Michael's stomach. He had finally made £120, and decided that he would answer no more calls.

It was after two in the morning that Michael was awoken by a light slap to the face,

"Rent. Gimme Rent."

It took Michael a few seconds to remember where he was. He'd had no intention of falling asleep but must have drifted off. Now there was a fat, stinking old guy standing over him demanding his money.

"Come on, come on you dirty pervert. I ain't got all night." The guy clearly didn't plan on hanging around. Michael reached out the wad of cash he had stuffed under his fake breasts and the landlord snatched the lot out of his hands.

"Hey wait! That's more than a hundred!" Michael reached for the cash but the landlord held firm,

"Too bad. That's rent plus queer tax. Don't be here when I come back and have a nice life." The landlord turned and hurried out of the door. Michael was still groggy and dazed,

"Hey wait! What about the next instructions!" The landlord was already halfway down the stairs and called back over his shoulder,

"I don't know nothing about no fucking instructions. Just get the hell out of my apartment before noon tomorrow." And he was gone.

Michael struggled to wake himself up properly. Everything ached. His jaw, his legs, his ribcage. He teetered around the apartment on his five inch heels, trying to find his next instructions but failing miserably. In the end he sat himself down again, resigning himself to wait and deciding he had better answer any more calls that came through.

Michael had to wait a long time for the phone to ring. He filled in the time by getting something to eat from the kitchen, practising his make up and generally trying to relax. He was dead tired, figuring he had only had around an hours sleep, but he didn't want to risk sleeping again. Eventually the morning light began to creep through the filthy curtains and the world outside began to wake. at around 8 a.m. the phone finally rang.

"Hello, hello?" Michael answered the phone, hoping to speak to his tormentors so that he could call this whole thing off right now. What he got was a digitised recording comprising of two words 'toilet cistern' and then went dead. Michael stared at the phone in disbelief for some moments before replacing the handset. These people were really scaring him now. Forcing himself back onto his punishing heels, Michael went to the bathroom to investigate the cistern.

Lifting the lid and peering inside, Michael could see a lone key lying at the bottom of the water. For once he was glad of his long gloves as he reached in to retrieve it. He figured that this would open up the locked closet in the living area and he was right.

The closet first appeared to be nothing out of the ordinary, just piles of junk and old boxes, but taped on the inside of the door was another envelope marked 'Lisa'.

"Hello Lisa. We hope that you are still enjoying your little adventure and that you have passed your 'O' levels with flying colours. You can be sure that we will be getting full reports of your performance from the 'clients' we sent you so you had better be up to scratch. Oh yes Lisa, they were all sent by us - we wanted to ensure you had a proper education. We hope that you have had a pleasant rest and sweet dreams of your cocksucking debut.

Now Lisa, it is time for you to return to the warehouse you woke up in. We don't expect you to have to walk of course, as you should have raised enough money to pay for a cab. There is a cab office on the corner of your block. The address you need them to take you to is on the back of this letter. It should cost around £15. If for some reason you do not have the money for this then, well, it's a nice long morning walk for you Lisa. What could be nicer? It might be starting to get a little busy on the streets of course, but we're sure you'll manage. We have decided to make this a little easier for you however, and if you look in the back of the closet you'll find a coat to put on.

Instructions will be at the warehouse. Be there by 10 or we disappear forever."

Michael felt the familiar feeling of nausea and excitement. He was going public again, and in broad daylight! How had he been so stupid as to lose that extra 20 to the landlord? He should have hidden it away beforehand. How the hell was he going to get all the way back to the warehouse looking like this? Michael dug into the back of the closet and found a shiny leather coat. He put it on and found that it came to just above the knee and was tightly fitted at the waist. Checking himself in the mirror he was stunned at the black, shiny vision that met him. His face was the only thing that broke the pattern, pale and painted against the creaking leather of the boots and coat, the slippery shine of the gloves and the sleek raven hair. He could admire himself looking like this for hours but yet his mood was spoiled by the fresh ordeal he was to go through. Dressing as a woman for this trek would be one thing, but dressing like no other woman you would ever see at 8 a.m. anywhere was quite another. He knew there was no choice, just as he himself had specified 'no choices but impossible ones'.

Lisa, the cocksucking whore dressed as a stunning dominatrix, left her seedy bed-sit and set off on her long walk.

(TO BE CONTINUED)

  

  

  

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