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Sissy Girl Stories


The Landlady

By Maxine

Sunday Afternoon… "So, you understand the Terms & Conditions of your stay?" She asked the quiet young man across the table as he finished his Coke and stared at the contract before him.

"Yes ma'am, I do." His Indiana accent was soft, in keeping with his slight physique. He picked up the pen next to the document dated it and scrawled a barely legible signature across the bottom of the page.

"Last chance now 'boy'." She emphasized the word boy in her special tone, "You are all mine for one week, thereafter on a week by week basis, your service is to be 7x24 all under my instruction and control. You will have a room, the one you have seen, and that is all. So either get up and leave right now before the ink dries on this contract or get up and strip and put all your clothes in the box in the next chair."

He paused for but a moment then stood and removed his clothes. As he stripped he could not help but glance over at his new owner for any reactions. He was fairly muscular and rather well hung, he thought. This, with his long hair, in a ponytail as usual, generally got the women in his life hungering for him.

His clothes he carefully folded and put in the box. They were not much, but they were his. The past year had not been kind to him. He had gone through two jobs after his last girlfriend had left in a huff. He seemed to just drift with no direction. It wasn't that he didn't have the brains or the skills, he just lacked motivation and will. This setup in Phoenix seemed ideal. Free room and board and all he had to do was take care of the place and once in a while jump the old girls bones. Hell, she was even good looking in an older sort of way. Very well preserved he thought as his gaze crossed over her lovely legs and took in again the set of breasts that he had been noticing ever since he walked in the door. Here, he thought, I can get my head together, have some sexy fun and then when I am ready I can move easily without any encumbrances. B&D? S&M? He had gotten around those issues by making stuff up as he went through the interview. Hell, she would never mess with him anyway, she was just a little old dreamer.

She watched as he put his past life away in the box. He was not nearly the stud he thought he was. And 'really', did he think she was daft in the head? She had caught him out in minutes during the interview. Of course she had been questioning his honesty ever since reading the resume he had sent. Subtle research and a few questions with relatives in the area he came from served to satisfy her of his real situation though and she felt he could be molded. She smiled though as she wondered if he would survive the molding process.

Done he turned to look at her and receive his first instructions. "Seal the box with the strapping tape and put it by the door for now boy."

Taking the tape he sealed the box well and placed it at the door near his two suitcases, garment and gym bags.

"Those will be attended to later boy. For now come here and lie down." He moved to do so and placed his head, as directed, near her shoes. "You may begin by licking the soles of my shoes and then the heels, when you are finished you may remove them and massage my feet. I want you to kiss my peds, lick them and smell them deeply as you massage them. Is that all clearly understood boy?" She finished and without waiting for a reply she placed her 3" heel directly on his face and picked up the phone.

As he started in on the shoes he thought to himself, "Not too bad, I can handle this." In the meantime the phone conversation went on above him. Over his head, so to speak.

"Yes dear I am all set here."

"No, the project will move along as planned and I expect no troubles whatsoever."

"Of course sweetheart, I will have insurance that will secure me."

"Yes, if you could take the rubbish out later that would be fine."

Piece of cake he thought. No rubbish duties, and the lady was getting more insurance. Who knows, he thought, as the first shoe came off and the smell of well worn nylons engulfed his senses smothering him with womanly earth scents, maybe I can work just enough to have her list me as the beneficiary.

Now that her phone call was done she was ready to teach this young boy how to really work with a Lady, all he was doing right now was getting her foot wet, hardly good foot worship at all. No tongue between her toes, no sucking of each digit like the little cock just some of many of hers he would have to get used to. So much work, so little time.

"Up boy." She spoke abruptly, commandingly, after all she now owned his ass.

Once standing she had him spread his arms and legs and then with a flirtatious smile began to run her strong hands over his body. Soon he was aroused and that was what she was waiting for. She started rubbing a soothing, warming lotion over his whole body. Legs, arm, chest, buttocks, every crack and crevice was thickly covered with the gel. He never even noticed, his head tipped back in an erotic fantasy of his own, that she was now wearing thin surgical gloves as she spread the permanent depilatory over his frame. However, soon he noticed the soothing rub and the warming lotion were getting too warm, almost hot to the touch. Then it became really uncomfortable and he looked at the lady and saw her little malicious smile looking back at him.

"Quickly boy, move into your bathroom." She shooed him away slapping him almost playfully on the buttocks, almost playfully.

He had never realized that his attached bathroom was so specially outfitted as she pointed him into a corner. He now noticed that there was no conventional showerhead in the enameled and tiled area only a powerful hose setup. This she began to unreel off the spool and then pointing the nozzle directly at him began to rinse his body with a blasting spray.

"Spread those legs boy." She commanded and when he hesitated she continued, "better to let me clean you with this than to develop the blisters that will come if you don't let me get it off."

Reluctantly he complied and soon the hard stream was crushing his balls and bruising his cock. She made him peel back the skin over the head so as to thoroughly cleanse the entire area. Then he was turned about and the spray went down his crack almost forcing itself inside his anus like an enema.

Speaking of which, now he noticed, in a quiet moment, that his landlady was hanging a full bag from one of the many hooks 'decorating' the walls and attached to it was a sizeable enema nozzle.

"Assume the position." Legs spread and arms against the wall he waited as she approached and then felt the nozzle pressed against his rectum. Slowly, firmly, it penetrated him and he was so embarrassed. Yet he would go along with this, he had agreed to it and after all, he had been through enemas before in the hospital.

"You will be cleansed now inside my boy. This is a one-gallon enema bag. You will take half now, half again and then one full gallon. The mixture is my own concoction of salts, soaps and unguents that causes certain scrubbing sensation you will come to enjoy, for I insist on assholes being clean." She laughed as she opened the clamp and let the fluid fill her new tenant, her slave. The mixture bubbled and churned inside of him, scrubbing the walls of his colon and filling him with a flatulence he had never felt before in his life.

Soon he was begging for release, the words music to her ears. Finally when release was granted it was again before her and the release was loud, embarrassingly so, and smelly and just plain disgusting. She however, just kept on with her stated plans and soon he had endured the next enemas as well, followed by a hard cleansing again with the iron hard spray of his shower. At last the trial seemed over and he looked at his denuded body, red and sore from the water beating, sore inside from the enemas and he felt spent. He was so tired and he felt as if he had been beat on for hours.

"Now boy come here." More directions to follow, it was all he could do to even move. His head was spinning. He was not certain of anything.

She smiled delightedly as he allowed her to dress and position him. The small amount of alcohol in the enema had gone directly into his bloodstream and the research she had done bore fruit in his complacency. He was a tired, winsome drunk. Of course the physical stress of the shower, the depilatory and the enemas had taken their toll as well. The flesh colored teats glued to his chest looked real, even in normal light and the earrings, garter belt, stockings and 'fuck-me' heels made him look like a real TV. His hair had dried and she had made it fluff as well as applied a bit of make-up. Here she could have used his cooperation but the boy was indeed a bit tired. She smiled at the results of her efforts.

Next out came another camera, the bot had not realized that every moment of his life was being taped and recorded. This was done thanks to his predecessor and that one also had the ability to professionally edit this into ANYthing she wanted it to look like. For now though she placed limbs thus so and used the toys of her liking, a large dildo for instance stuck between rouged lips, even with his eyelids closed merely made it look like she was in rapturous ecstasy. In his stupor he was easily positioned against the wall, bent over head facing back between his legs, ankles spread, in a "come and take my ass" look, especially with the seams of his stockings so straight. The addition of a realistic looking and VERY large dildo to his ass was hardly noticed by the slave, certainly he was not in a position to refuse. The picture with the dildo half-in and half-out told the whole story.

Ultimately she led him to his bed and removed the comforter. He would never being using it anyway. This revealed a very sturdy cast iron bed with welded rings around the head and foot boards. Other features were out of sight for the moment but would come into play later. For now she laid him on his back and secured his hands and feet to the corners most competently. Patting his rosy cheek she left him to recover.

Moments after making a call the door opened and two women came in and greeted the landlady with a mixture of deference and eagerness. One of the ladies was perhaps 20 and the other well over sixty, but a spry sixty from the glint in her eyes. Coffee awaited them at the table and all three sat down to discuss the new project.

After they finished talking the young lady rose and took the man's bags out to his car. She then drove off to a secluded garage area and locked the car and its possessions away. Walking back to the apartments she couldn't help smiling and thinking of what her aunt had in mind for this new 'tenant'. She was glad school was out for the next two days and she smiled more as she felt her thighs dampen in her anticipation. She quickened her stride as she realized he was going to be up in about 4 hours and they still had things to prepare.

Sunday Evening…

"So our little boy is awake finally." The Landlady gazed down imperiously at the captive male. Her two assistants stood just beside her with small smiles on their faces.

"Boy, I will introduce you now to two other Ladies that will be instrumental in your training and maintenance. On my right is the lovely, and young, Atheris named for a particularly deadly black viper. Let me assure you she is just as dangerous."

The Lady Atheris looked down and waved at the helpless boy. His eyes widened in fear, fear that made her smile all the more when he recognized the needles protruding from the palm of the vampire glove she wore.

"And this my young man is the Lady Elizabeth. Lady Liz to her friends, one of which you are not." She indicated the spry, gray haired lady on her left. She too smiled down at the bound slave and slowly took in his crossdressed form, licking her lips greedily as she took in his manhood.

"You may refer to me henceforth as Lady C. In the days ahead," she continued, "these Ladies will help me with you so that you are constantly watched and disciplined for any infractions. Or indeed just disciplined just for our entertainment. No doubt you came here thinking that your life would be easy and largely carefree. No doubt you thought that you would be able to 'jump my bones' as some have thought in the past. Let me assure you here and now that nothing could be further from the truth." An evil smile filled her eyes as well as crossed her lips. The boy had not spoken once yet and that alone had saved him his first encounter with Athris' glove. Regardless, he would feel it soon.

"Indeed it will be Lady Liz that jumps your bones. You will find that I will also jump your bones, but in my own unique way," And holding out her hand Lady Liz placed a complex leather belt and harness arrangement. An arrangement that had at its center a rather large, severely long and grossly twisted black dildo. "You my pet shall get used to accepting my taking of you. Just one of the many reasons why I insist upon you being clean inside and out." She stepped into the harness and Lady Liz and Atheris began cinching and strapping the sides and back to her so that her weapon, one and a-half inches in girth stood out a full, straight ten inches from her body.

"As for young Lady Atheris here you will find her appetites most interesting. And insatiable." At this time Atheris sat next to the man on the bed and began to softly stroke his cock and cup his balls in her viperous grip. Immediately the boy jumped and tried in vain to struggle against his bondage as the needles scored his flesh and penetrated his cock and scrotum in dozens of points.

"For now we are going to indulge ourselves in getting to know you. You will remain ours until we have either had our fill of you, you die or we elect to sell you south of the border. The latter options are wholly dependent upon your attitude." She could tell that he was scared at her pronouncements and was about to speak out despite the agonizing, twisting grip his balls were now being held in. "Do not attempt to protest or negotiate. I know hold several forms of insurance over you to insure your continued, if not whole-souled, cooperation. You see you posed for an entire series of photos earlier." These, fresh from the developers, she held before his wide eyes. Then clicking a controller she drew his attention to the TV in his room. "These, and prior and following actions are being taped for my benefit and archives. I have a dear former pet, now the property of a wealthy socialite her in town, who can make these videos demonstrate ANYTHING we want them to my boy. Do you understand your situation?" She looked down and saw the arrogance and fight diminish in his eyes and defeat begin to blossom. He nodded.

"Well and good. You really do not, not yet, but you will my boy, I promise you that you will. Atheris, why not take a break and go to the bathroom." Atheris immediately stopped her glove play and went to the toilet where she peed in a loud, long stream.

"My dear Lady C there seems to be no TP here for me to use." Lady Atheris intoned almost comically, already knowing what the reply would be.

"Well the boy doesn't need any. He will be trained to defecate each morning and then receive his cleansing shower. In this situation it seems you will just have to use his lips and tongue as your TP my dear." Lady C looked back to the boy and caught his grimace. She did however give him points for again not speaking out, perhaps he was a keeper after all. Time would tell.

In the meantime Atheris had moved to the bed and standing astride his shoulders she began to lower herself slowly, seductively, teasingly onto his face. Once down she reached behind with both hands and pulled her cheeks apart slightly, just enough to make certain that his nose and his mouth were both tightly covered with her seat. To make certain that his tongue gave every effort she placed her needle gloved hand over his nipple and "scratched" - just to keep his attention.

Lady Liz looked to Lady and received a nod. Immediately she stripped the nylons from legs and bound the males hardness with them. In moments his balls too were securely wrapped in a neat little package. Without a seconds hesitation she then mounted her bound stud and began to ride him with a frenzied abandonment. It had been too long since a cock had stretched her pussy and she was hungry for this one.

Lady C looked on and enjoyed the scene of the bucking young boy. His face being ridden mercilessly by Atheris and his cock being milked by Liz. Soon both women were swooning in the midst of their first climaxes. She didn't have the heart to tell the boy that they regularly expected three or more per day. Each. He would find out soon enough. As for herself, she could already feel the heat in her loins. The special harness had an interior cock that filled her own pussy and throbbed with its own vibrations. These would be intensified greatly once she took his male pussy for her own.

The riding women climaxed, held each other in a supporting embrace as they did so and then jointly turned to Lady C with smiles on their face for their next directions. Lady C merely split the fingers of one hand and wagged them at the Ladies. And as lady Atheris climbed from her perch lady Liz moved forward to take her seat on his face and drench him with their mutual juices. Making him drink his cum from her pussy.

Down below Lady C and Lady Atheris undid the ankle bondage from the bed and ran it through ceiling pulleys, pulleys that raised his legs and bent him into an L, his ass well off the bed.

Now it was Lady C's turn to enjoy her pet and she did so with gusto. Using just the cum that had trickled down to his anus as lubrication she began to work he way slowly, steadily deeper and deeper into his ass. Having been greased, lubed and stretched earlier by the enemas his ass was ready to take her in fully. She set a grueling rhythm, but one that was in synch with her needs, not his comfort. Minutes passed until finally she arched her back in a grand gesture and impaled him most forcefully, burying herself deep in his ass, his pussy, which was hers from now to time indefinite.

Hearing Lady C climax Liz could hold back no longer herself. In a giant climax she ejaculated all over her prisoners face, filling his mouth, flooding his nostrils, blinding him with her womanly cum. Coughing, choking, hacking he was finally released from face sitting bondage and allowed to catch his breath. A keening wail was heard from him as well when Lady C withdrew her ever-stiff rod from her new found pussy.

"Not bad boy. Not bad at all, for a start. Now Lady Atheris will release you. You will be allowed one glass of water, a chance to pee and then be tied to the bed for sleeping. ANY trouble on your part will bring out the Black Viper in our girl and you do not want to face that before you have to. Do you understand?" Again she watched closely as the spent youth nodded his head slowly, tiredly and accepted his orders, his place in their family.

Leaving the room Lady C's head was filled with plans for the morrow.

Monday morning…..

He woke to the feeling of heavy thighs sliding over his face. His arm and leg muscles had atrophied from the night of bondage and he felt as if he could barely move. He knew to open his mouth and greet the warm pussy settling about him with his tongue, still sore from the previous day's activities.

"Now boy," She began, "this is your first wake-up call. I have saved my toilet for you. Be certain not miss a drop dear. For this first session I will go slow with you." She began to release herself in short steady spurts, placing small pauses between them. This control exercised muscles that inevitably made her hot and by the time she was finished she was frantically riding his face in wanton passion. Always controlled in the presence of her friends alone she was a sexual tigress. Her appetite was virtually insatiable which was why the 24x7 servitude arrangement was specifically mentioned in her ad. The boy was hardly ready for her climax, for when she did she came copiously, gushing cum all over his imprisoned face. Unprepared he had no way to keep up with the volume that swamped his senses.

When she was done she rose and let her night dress fall and cover her. Turning to his bonds she released him, and in a display of kindness actually rubbed the blood back into his extremities. Eventually he sat up and then, with her assistance, stood up and stretched his body out completely.

Before he could get too comfortable she led him to the bath area and had him strip off the feminine apparel and complete his morning ablutions. These however had the one added chore of taking his enemas. "You know my sweet pet," she began to inform him, "these enemas can be terribly habit forming. In fact, after regular usage there will come a time when you will be dependent upon them. Isn't that interesting. Something you will always remember me by boy." Her evil smile tore into his brain as his bowels emptied into the bowl. Then it was time once more for his 'shower' and once more the forceful spray beat him near unconscious. Then he was led to the bed and allowed to stretch out on its frame.

During his recovery he could feel her manipulating his manhood and family jewels. He smiled in exhaustion, to beat to even care. That is until her heard a soft 'click' and then his limbs shot straight out from his body and a mighty "GOD DAMN" was torn forcibly from his lungs. Thereafter he immediately went into a fetal position, his body shaking uncontrollably, bile rising in the back of his throat, involuntarily his hands reached down to cup his scorched balls, not expecting to find them, only to find them still there and apparently well, though bound now by a sterling metal ring and small metal box.

"Boy, what you just felt was setting three of ten on this remote unit. The effective distance is about 100 yards. Of course then what happens is that the unit just fires off repeatedly at its highest setting until the battery unit expends itself. Maybe 15 to 20 minutes under a full charge. Certainly enough to complete fry your balls. You see this is a modified Taser unit delivering around 75,000 volts. You just felt maybe 25,000 tops. There are three of these Behavioral Modification Control Units and each of your new owners has one in their possession. Breaking one, or all, causes the override feature to take effect as well." She sat next to him on the bed and continued. "So let me summarize for you boy. Do you understand what I am telling you?" She jostled his arm and heard his faint, almost sobbing 'yes' in response. "There, there boy. You are all right, for now." She turned his naked body over and spread his arms away from his scrotum. She then began softly massaging the tender flesh as she told him his circumstances. "So you must understand there is no running away. This box and band are locked on with a special pick-proof lock the key for which is no where on the premises. They are also electronically daisy chained and so stealing one does you no good, get beyond 300 feet from two units and your balls will fry." To punctuate that comment she squeezed his balls hard and grinned as he squirmed in her grasp. "And as to running, that is what you will have to do. You see your car is nowhere to be found. As for my transportation I have those that run and fetch for me or will come and take me out if required. But I am perfectly happy to remain here at home and have you care for and pamper me. Lastly, you also have no male attire to wear. All your clothes were disposed of yesterday while you slept. You will find in your small closet and dresser all the clothes you will need while you remain here. All distinctly feminine in nature. I doubt you would want to be seen in public dressed in them. Not yet anyway."

She rose from the bed and walked to the closet and dresser gathering certain items from each. Motioning for him to rise she held the items out him one at a time and had he don them. Soon he stood before her in red. Red sheer bustier, red skimpy panties and red thigh highs. Now she directed him to the corner setting. There he sat, as instructed, before a lady's vanity complete with all manner of make-up and basic jewelry.

"For now boy," His head nodded forward in tiredness, SMACK, SMACK, twice she cuffed him upside the head to gain his attention. "PAY ATTENTION BOY!" she shouted at him, not loudly, but intensely and for reason that all the more scary to him.

"I will, I will pay attention." He murmured ducking an anticipated blow that never fell.

"You will be told this once, demonstrated once and then Lady Atheris, on her next visit with you will help you ONCE. Thereafter you will be expected to fix your make-up perfectly each day. You also have a video, the only one you have I might add, that covers make-up techniques and acting like a young lady. How to walk, to talk, to sit, to stand, basic proper decorum and manners. In short, from now on you be treated and used as a slut but expected to conduct yourself as a lady. Do you comprehend all of this." She asked him, turning his face to her so she could look him directly in the eyes.

His shoulders slumped in defeat as it finally registered within him. What had he done? What had he gotten himself into? He was caught, he tried to think, but couldn't come up with a means of escaping these devil women. His eyes left hers, falling towards the floor, as he told her "Yes."

"Good. Then let us begin for you need to start breakfast soon. I am famished after last night." She kept up a constant dialogue as first she took a small gun-like instrument from a drawer and pierced his ears. The piercings she quickly filled with fashionably small zirconium studs. Next she took a set of specially made 'permanent' nails from the drawer. In addition to their own adhesive she applied a small drop of SuperGlue. She showed him how to form the nails, apply a sealing coat, then a base coat and finally a top coat. During this transformation process she talked with him, and treated him like a girl friend. Here in this woman's world, his own little corner, he was safe.

The transforming was not complete though. His face needed work. She began with a small sponge and a creamy base. This was smoothed over his entire face rather thickly. Next powder was applied and highlighter to accentuate his cheekbones and reduce skin glare. A bit of eye-shadow and lip lining followed by a red gloss and he was almost ready. Standing behind him now she took his new brush and pulled it through his hair, his tresses.

He was staring at himself in the mirror. He could not believe it, "where did I go?" he could only stare and wonder to himself. The somewhat good looking woman staring back at him looked lost. Above him Lady C watched the process take place and smiled in a most satisfied and devilish way.


Sissy Girl Stories