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She was a seemingly quiet and solitary young woman of around thirty. Though not unattractive, she dressed very plain and often mismatched. Being rather shy and reserved, you would never see her going out with guys. She just lived above her employer's office and kept to herself. Perhaps she was even a virgin, destined to become an old maid. Who knows, she may have never even masturbated to bring herself sexual pleasure. However, deep inside lurked a horny vixen, who longed to enjoy the pleasures a man could provide.
He was an older gentleman who lived in the same neighborhood. At least, for all appearances, he was a gentleman. Although, he had several women in his life come and go, for the last few years he had lived all alone, keeping mostly to himself. Secretly, he was a dominant, who derived most of his pleasures from hearing the women who served him squeal from both pleasure and pain. He trained them to service him and to give their bodies over to his total control. These women lived to enjoy the painful pleasures and multiple orgasms delivered at the hands of such dominants.
Except for his ex-wife, who left him because of his controlling nature, he met the other women who had been a part of his life through personals sites on the internet. He never enjoyed the bar scene and had no interest in the sluts who frequented these places, throwing themselves at any available man, once they had enough alcohol in their systems.
He kept himself clean and, though a little overweight, he was also in reasonable physical condition. He had no interest in the risk of contracting a disease from any these easy women. Besides, you could not just walk up to a woman in a bar and tell her you wanted to take her home, tie her up, whip her and use her for your pleasure all night long. Sure, many of them may enjoy it. But, besides the health risks, a man could get himself thrown in jail and labeled a sex offender, if he approached the wrong woman, even, if she had already followed him home. No, he knew that if he found the right woman for him, they would have to share similar interests and be aware of each others interests before they ever even met in person.
With the lack of a submissive woman in his life to help him release his pent-up desires, he resigned himself to strange rituals of self-bondage and pleasure. After all, if you don't use it you will lose it, the saying goes.
Since he had no one in his life to dress in the sexy lingerie he preferred, he would often dress himself in those same silky and lacy articles of clothing, just so he could enjoy the feeling of the material brushing against his skin. It brought him no real pleasure, but, attempted to satisfy this one of his fetishes.
And, not having anyone else to tease and torment, he turned his attention to himself. If he could not tie up a woman and tease her until he was ready to bring her to repeated screaming orgasms, then he would just have to do it to himself. After all, someone needed to suffer, in order to reach their climax.
Unfortunately, when these desires continued to go unfulfilled, the need continued to grow. With the growing need came greater torments and risks. Those risks would eventually backfire on him, if he got careless, and he did.
It started by adding chastity play to his list of torments. In order to tease himself for longer periods of time, he purchased both CB-2000 and CB-3000 chastity devices, along with KSD-G2s and altered them until it was impossible to pull himself out or remove it without a key in his possession. At least he could not free himself, without the chance of doing himself serious harm in a very tender area.
But, this was not good enough. After all, he still had the keys. Soon, he got the idea of hiding the keys someplace inaccessible. But, where could he hide the keys and not be able to retrieve them? After all, he was really a dominant and had no interest in turning over control to a key-holding mistress. This was just sexual play to provide some degree of satisfaction until he found another worthy submissive.
Ah, he thought! There is a park about a mile away from his home which was locked behind fenced gates at night and surrounded by water. There was no way he could access his keys at night if they were hidden in there. Now, his manhood would have to stay locked up and untouchable all night long, until he could retrieve the keys. Occasionally, he even managed to keep himself from retrieving those keys over the weekends, further increasing his sexual frustrations.
Soon, even that was not enough to satisfy him. Sure, he could apply wrist and ankle cuffs and/or use yards of rope to restrain his body for a while. But, again, he still had the keys to those locks. And, ropes provided too much risk of never getting loose; perhaps even cutting off circulation to the limbs he needed to free himself. From his reading on the internet, he learned to place the keys inside a container of ice, so he would have to wait for the ice to melt, in order to get free. With practice, he discovered a container which, when filled with water and frozen, took most of the night to melt. Now, he could trap, tease and torment himself all night long.
But, even this, was a risk which struck him with a degree of terror. If the keys did not drop where he could reach them for any reason, then he would be stuck there and probably die. After all, he lived alone with few visitors and preferred to gag himself, so the neighbors would not be able to hear his moans or screams.
The place where he lived was fairly protected from the outside world by tall trees which partially obscured the view of his apartment. Although, out in front of the building, the street was very busy late into the evening, his home was still fairly secluded. The only decent view of his place was from the building next door. This just happened to be where that plain and simple young woman lived above her employer's office.
This was the same young woman he had watched for years and found intriguing; thinking, with a little guidance from a dominant, she could be a very attractive woman. Yet, try as he might to strike up conversations and perhaps catch her interest, she seemed unapproachable. He had even harbored fantasies that her shyness was really designed to hide her submissive nature and desires to serve, should the right man walk into her life. Little did he realize just how right he was, about this interesting young vixen. He didn't know that she was capable of giving him everything his heart and sword desires.
One day he got a not so bright idea. If he placed the key to his apartment outside his window later at night, perhaps after day-break there would be a chance of her noticing and then he could be discovered and released before he would die of starvation and dehydration. As long as his release worked, he could collect the key again, before it turned light and became visible. Or, maybe his friends would stop by, see his car was there and check around to see if he was out back and find the key to rescue him. At least they knew he was a kinky pervert.
He knew there were risks. There were always risks. Maybe someone else, other than his neighbor or his friends, would wander through and find the key. Perhaps some of the nice young college girls in the area would wander through the yard and happen upon it, see him lying helpless on his bed through the sheer curtains and decide to have some fun of their own. Not such a bad thing, as he may get some sexual pleasure, after all.
Or, it could be a group of guys who discovered his not-to-hidden secret. This was not such a pleasant risk, as he never found any interest in other men. He was strictly heterosexual and getting used by a bunch of guys would be humiliating at the least.
Then again, those of a criminal mind could discover the key and steal everything of value he owned. They may even take advantage of him and beat him senseless in the process. Still, his apartment was fairly secluded and those chances were very slim, at most.
Another possibility was that his neighbor would notice, but call the police, instead of rescuing him, herself. This would be embarrassing. But, he would live, and since he was not breaking any laws of which he was aware, he should only have a lot of explaining and apologizing to do. After all, he was not exposing himself or approaching anyone. He was tucked away in the privacy of his own bedroom behind curtained windows.
His sexual needs got the better of him and he decided the risks were a chance he was willing to take, in order to attempt to satisfy his urges. After all, there were some small chances he could enjoy himself more than he hoped. And the worst that would probably happen is his rape and humiliation, at his own hand. At least if discovered, he would probably live. He never foresaw the other possibility; the one which would change things in a way he never really imagined.
The weekend was here, again, and it was time for a long session of self-torment and pleasure. Several weekends of this type of play had come and gone, without incident. There was even a time when he had set out the keys and a group of people had wandered between the buildings early in the morning and never even noticed him through the curtains. So, he thought he was safe.
That Friday, as he had done many times, he took the keys to his chastity device down to the park and hid them in the trees, where it was very unlikely of anyone discovering and taking them. Now, his manhood was locked away and throbbing for release, until he retrieved the keys. This was a release which would wait for quite a while.
After hiding the keys to his chastity device, he returned home and spent the evening reading stories of others who enjoyed similar pleasures to his own. When he ran out of stories, he watched hours of sexually graphic movies, until he became so tired, he finally went to sleep.
However, sleep never lasted more than a couple of hours, before he woke up with a strong need to relieve himself. Perhaps it was nocturnal dreams arousing his sexual desires and causing him to swell inside his little prison. Perhaps, it was only a strong need to urinate, which caused the swelling. Either way, those swollen wake-up calls just added to his torment and increased his deep need for release.
Despite his desires and enforced torments, he managed to get through the day without breaking down and traveling to the park to retrieve those keys. He occupied his time by cleaning around the house and taking care of other projects. Part of his time during the day was also spent preparing for the grand torment to come in the evening.
He cleansed himself inside and out, giving himself several enemas to remove any need of defecation while he was restrained that night. This also allowed him to insert a large plug, adding to his torture, by stretching and filling his ass, all night long. He shaved off all his body hair and rubbed baby oil into his skin, afterwards, so his body would feel soft and smooth while being rubbed by the silky lingerie he would wear that evening. After all, if he kept his body in its naturally hairy state, it would detract from the pleasure of feeling all that nylon sliding across his skin.
By this time, it had become dark, again. It had now been over 24 hours since his throbbing manhood had been locked away in its prison. It would be at least another 12 hours that night, before he could retrieve the key in the morning and masturbate himself to exhaustion.
He typed up a note on his computer inviting any unexpected guests to use him and train him as their sexual slave. This just helped to add another bit of uncertainty to his predicament. Upon finishing, he opened his bedroom window and placed his door key on the stone lintel right below. His window sill being over six feet above ground, he doubted anyone could see it sitting there. Anyone, that is, except the woman next door if she were standing on the front porch or looking out the window in his direction. And then, it was lying flat and she would really have to give a good look, in order for it to catch her eye. But, at least he felt some comfort that there was a chance of rescue if his release failed.
Then, he taped the note to the mirror above his dresser, hoping nobody actually discovered it. What a dangerous and interesting night it would be if anyone actually discovered his key and took advantage of his situation. The note said:
It was later in the evening, after several more hours of tormenting his frustratingly caged manhood, when he finally decided it was late enough to apply his bondage for the night. Tonight it would not matter how hard he became in his chastity device or how bad he needed to urinate to reduce the swelling in his groin. He would not get relief until the keys to his chains and locks melted their way out of the ice. For the next 5 or 6 hours, he was to be a prisoner of his own demise. If only he knew exactly how his weekend was about to turn out.
He began by wrapping his waist in a restricting waist cincher to pull in his slightly overweight belly. Over the top of that, he wore a waist-nipping corset with eight garters to support his full-fashioned nylon stockings and further restrict his waist, along with is breathing. Next, he slipped into 5" stiletto-heeled black patent shoes with buckling ankle straps which prevented their being kicked off before he regained his freedom. Those shoes placed a lot of pressure on his toes, which further added to his suffering. Gawd! How he wished it was a woman wearing these things for him, instead of having to do this to himself for what little pleasure it provided.
Now, he had to walk around to finish his preparations, while wearing those high heels which made him take small, dainty, torturous steps with bent knees. The next step may have been the worst, because of those sexy shoes. Now, he was ready to install the butt plug and the belt which would ensure it could not slide out until the keys dropped into his grasp or someone discovered and released him. After that was inserted and locked in place, he slipped into a pair of loose fitting nylon panties which would slide across his groin and a slip to slide across his chest and thighs.
Ready to settle in for the night, he walked about the apartment turning out lights. He only left the usual nightlight on in the kitchen and a low-wattage table lamp in his bedroom, so he could see what he was doing for his final preparations. He also left several whips, dildos and sets of clamps setting out on the dresser, just in case someone actually did discover him and decide to take advantage of the situation. It would keep his mind jumping with every noise he heard. Oh, it was going to be a long, hard night! This would be more interesting than he had previously experienced and it was his own doing.
Once he was dressed in all his silky nylon lingerie, he placed leather cuffs, hood, collar, ropes and gag within reach on the bed. He buckled 4" wide leather cuffs around his ankles and tied a three foot spreader bar in place between them. Now, not only was he wearing shoes which would place him on his toes; but, his legs were spread wide open, providing anyone access to a wide area of his thighs and crotch.
Lying back on the bed with his legs draped over the end of the footboard, he grabbed a couple more ropes and wrapped them tightly around his knees, leaving several feet of the ends unused. The ends were stretched out to rings in the sides of his waterbed and tied tightly with several knots, keeping his knees spread as wide as possible. His lower body was now totally helpless and vulnerable.
But, this night was to be so much different from all the others. This would be the night which would change his life. He never realized the girl next door was watching from her second story window. She peered into his bedroom through the sheer curtains covering his windows and providing him with a false sense of security, with mixed feelings of amazement and frustrated desires of her own.
She watched, as he slipped on the wrist cuffs and attached chains to the buckles. The clasps on the chains closest to his wrists would allow the cuffs to be removed very easily, if only he could reach them. The 3" wide cuffs would not allow such a luxury to their prisoner. They would only give this option to an outside party.
Now for the final touches. He slipped a padded leather blindfold snuggly over his eyes, blocking out all light. Next, he applied a lycra hood with an attached locking leather collar over the top of the blindfold and locked the collar in place. The hood had only one opening for his mouth and was thin enough to allow him to breathe through his nose, but now, it was impossible to nudge the blindfold off his eyes or remove the hood. Finally, he placed the ball gag harness in his mouth and buckled the straps very tight, pulling the ball deep into his mouth.
Feeling around on the bed next to him, he found the locks for his wrists. Slipping each one through the end links of the chains from his wrists, he reached out and locked them to other chains attached to the bed rails. This stretched his arms out to the point where bending his wrists to reach the snap buckles attaching the chains to his cuffs was even more difficult, if that was possible.
Now, all that was left to do was lie in torment until the keys finally melted and provided release from his self-inflicted torture. Or, was that all that would happen this evening?
While he was busy preparing his wild invitation and placing his apartment key on the window sill, she was enjoying herself with a nice long, hot bath. But, now the bath water was getting cold and it was time to get out. Drying herself off, she looked in the mirror and examined her self. She wondered why she could not find a nice man to be part of her life. She did not think she was ugly and she definitely was not fat. Yet, others less attractive than her managed to find happiness and comfort in the arms of a man. She sighed, wrapped herself in a pink fuzzy robe, and walked out of the bathroom, turning out the light behind her.
Just then, she thought she heard a noise from between the houses. She wandered into the spare room to peak out the window and make sure there was not a prowler. Invisible to her neighbor through his curtains, she stared out the window in disbelief at what she saw. What kind of pervert was living next door? She would have never suspected anything like this from passing him on the sidewalk or from their brief chats.
She watched as he lay back on his bed and slipped leather cuffs around his wrists and locked them in place. Then she saw him slide the blindfold over his eyes, pull the hood over his head and lock a collar on, preventing the hood from being removed. Now she watched as he pulled the red rubber ball gag into his mouth and attached all the straps around his head. "Won't he suffocate", she thought to herself? He has to be crazy. At the same time, she found her hand wandering down between her legs, while her legs clenched tightly together. Reaching under her robe, she found herself getting wet. She could not believe watching this bizarre act was getting her excited. Was it from seeing her neighbor partially dressed and in women's clothing? Or, was it the act of bondage which tripped her trigger.
Sure, she had imagined being taken forcefully. But, she had never had any fantasies of bondage and slavery. Yet, she found the thought exciting and wished it was her in the restraints.
As she turned to walk away and take care of her own needs, she caught a brief glimmer of light on the windowsill, as a car passed by on the street. Its headlight flashed on something lying on the windowsill. As another car drove by, it happened again, and she had a brief glimpse of a key lying there. "Is he expecting someone", she thought? "Or, is that an invitation to me", she wondered? Thinking it could not be for her, she turned and walked away to go satisfy her own urges and get ready for bed.
About two hours later, after having settled in to bed and tossing and turning for quite a while, she realized she could not get the image of her bound neighbor out of her head. Nor, could she manage to satisfy the feelings flowing from between her legs. She got up and wrapped her robe around her body and wandered over to the window where she had observed everything, earlier.
She could not believe her eyes. Over two hours later and there was her neighbor, still chained to the bed. And, he was still all alone. Not only that, but, he was jerking around in his bonds and grinding his crotch in the air like he was trying to rub against something. In fact, the slip he was wearing had ridden up his hips and over the top of his panties, giving her a better view of the lump underneath them. She could not believe how hard he looked under there. She could not believe he was doing this to himself.
Without realizing what she was doing, she reached one hand between her legs and the other hand reached to her breast and started pinching her nipple. This scene was actually making her hornier than she had ever been in her life. As she opened her legs to allow her fingers to slip inside, a large stream of juice ran down her leg.
At the same time, she found herself think he may be in some kind of trouble, deciding she had better get dressed and go check to see if he was OK.
Being fairly warm on this early spring morning, she slipped a light sundress over her head and slipped into a pair of sandals to protect her feet.
Sliding out the back door and around the building, she realized that she could get a better look into his window, because of the different levels of the ground between the buildings. "He really looks like he is in trouble", she thought to her self. "Nobody would be shaking around restrained like that, unless they were trying to get free." From her current viewpoint, she could clearly see that the shiny object she spotted earlier was a key. Slipping over to the window, she reached above her head and felt around for it. While there, she realized he had left the window partially open and could hear him moaning into the gag.
Lying there, grinding on the plug in his ass and trying to get his cock to release its built up fluid, he thought he heard a rustle of leaves and a small branch snap outside his window. He stopped shaking and listened with both fear and excitement of what it might be.
Next, he heard a light scraping sound from the stone window sill and something moved the key he had set there earlier. "Oh my god, was that a stray cat or did someone find the key before he could get free", he thought to himself? He began to panic and could only imagine the possibilities. It had been very quiet, so at least he thought it could only be one person, if it was not a cat. Still, who or what was it? His cock suddenly began weeping, profusely. He could actually feel it running down between his legs and it didn't seem like it was going to stop. The need to cum was all he could think about at that moment and he started shaking wildly, again, despite wanting to keep quiet and hear what was happening outside his window.
Next thing he knew, he heard a female voice quietly call to him through the window," Are you all right?"
"Mmmmmmm, mmmm", was all he could answer.
"I found your key on the windowsill and I am coming in to help", she called out to him. He recognized the voice of his young neighbor and started flowing from the tip of his cock, like he was being milked from the large plug rubbing against his prostate.
Moments later, he heard the lock and the door opened and closed, being locked again behind her as she entered his apartment. Then, he heard her stumble around in the dark entrance as she found her way to the light coming from his bedroom lamp.
"Oh my, you certainly did get yourself into quite a predicament", she said. "I never imagined how sexy a guy's legs could look in a nice pair of stockings". I've only seen nylons like those in old movies". "Look at those heels, can you actually walk in them", she asked?" Maybe you can show me later, after I let you up". "Mmmmm" was his only response.
Glancing around the room, she spotted the note he had posted on his mirror. "So, you're a naughty slut that needs punished and trained?", he heard her say? "Well now, you should be careful what you ask for, you might get more than you can handle", he heard next.
At that moment, his cock spurted like a small orgasm, creating a wet spot on the front of his panties and he felt a lump in the back of his throat. "Bring it on babe, I need it bad", he thought to himself, not being able to do more than grunt.
"Looks like I got someone even more excited", she said, as she began running her hands up and down his stocking clad legs. Reaching up to the puddle sitting atop his stained panties, she began rubbing her finger around in it. He began moaning louder and grinding his crotch into her fingers as hard as his bonds would allow.
"What is this under here" she asked, feeling the hard bars of his CB-2000 through his soaked panties. "I've never been with a man, but, I don't think that a cock should be this hard and bumpy", as she reached up and pulled the waist of the panties down as far as his spread legs would allow. "Why is he all locked up, like this, was he a very bad boy"? "Look at all that fluid running down underneath your ass. I guess he is a bad".
"Tell me if you like this", she says, as she ran her tongue all around his cock in between the bars, licking up as much of the fluid as she could. "MMMMMMMMMMMMM", he screamed into the gag.
"I'll take that as a yes", she said. "I think I like him all helpless like that, so we'll leave him to suffer for a while". "Will you behave if I remove that gag"? "Watching you from my window next door made me almost as horny as you." "I need some relief, and since your not going anywhere for a while, I think you'll do nicely." "I watched you put on the blindfold under that hood, so I know you can't even see what I look like without my clothes." "I hope you enjoy eating a little hair pie." "I see you keep yourself shaved, but, I don't." "Be a good boy and I may let you free when I am satisfied."
He felt her get up from between his legs. Then she said, "This short braided leather whip may come in handy in case you get out of line." "And, what are these for", she asked as she picked up a pair of clover clamps attached with a chain? "I've seen them used for sewing, but, where do you use them"?
"I sometimes like pinching my nipples, let's try them there" she said, as she reached up and attached one to each of his nipples, through the silky nylon slip. He grunted as each one was applied. "Oh, does that hurt", she asked? "That will give you more encouragement to be nice to me".
The next thing he felt was the bed sinking on one side, as she climbed up near his head. Then, he felt her reach around and unbuckle the gag straps.
"Now, I have been saving this up for such a long time, so I may be a while. I hope you're up to the task." "I know part of you is, but I need your tongue to get busy. Now"!
She settled down hard over his face, spreading her ass cheeks over his nose to muffle any sound and swung the leather braided whip down hard on each of his thighs, several times, leaving streaked red welts with each strike.
"And, don't stop until I tell you." "We have the rest of the night." She pressed down harder on his face, taking away his breath and reminding him who was in control. Holding there for almost a full minute, she finally eased up and allowed him to catch his breath, but kept her lips spread over his mouth. Then she said,"Oops, I guess I need to let you breathe, once in a while. I wouldn't want you to suffocate under there".
"That's it, deeper; fuck me with your tongue, faster". For a virgin, she was a fast learner at controlling a helpless man. "Oh yeah, I like this." "Why didn't I get closer to you a lot sooner"?
"Now, stroke my clit with long, gentle strokes". "Gentle", she screamed at him. "I guess you do need training", as she brought the whip down on his thighs repeatedly, causing him to scream into her pussy. "Those vibrations feel great". "Looks like your thighs are going to be very tender, before I am through with you".
She continued to whip him for what seemed like forever, while grinding her dripping cunt against his moaning and screaming mouth. Of course, hardly a sound could be heard, as she was pressed down so hard on his mouth. She screamed out in her first orgasm of the night. The juices from her pussy began flowing so hard he could not swallow fast enough and began choking.
"There, there. That's a good little slave", she said as she eased up the pressure on his mouth and allowed him to catch his breath. "That's it, get a good breath".
"Now, back to work", she yelled as she reached down to the chain connecting his nipples and pulled up sharply, causing him to arch back and bury his face back into her box, again. He screamed into her pussy as she continued to pull upwards on the chain, until it felt like she would rip the nipples right off his body.
And then it happened, she pulled so hard the clamps slipped off his nipples because of the nylon caught between them. She could hear him whimper and begin to cry from the intense pain of blood rushing back into his previously compressed flesh. "Don't think you're going to get off that easily", she told him.
Reaching down and grabbing hold of his tender nipples, she began to twist and pull them with her fingers while digging her long nails in deeply. "Now, get back to work, you have a long way to go in order to earn your release". He whimpered, "Yes Mistress", and buried his tongue so deep inside, he thought he felt the frenulum begin to tear.
Just then, the keys for his release broke free of the ice, swung down on the rope hanging from the ceiling and smacked her in the arm. "So, that is how you planned to get free". "Sure took a while for these to drop". "Seems you like to be restrained, tortured and used for long periods." "Well, who am I to deny you such pleasure, when you have given so graciously to me"?
When she commented about the keys dropping it distracted him and he eased up on his service. She was not happy about his lack of diligence. "Get that tongue back to work, slave, I didn't say you could stop", he heard her yell. Just then, she began whipping directly on his ball sac, again and again. He began whimpering, screaming and pleading for her to stop.
Unfortunately for him, none of this escaped from beyond the pussy lips pressed tightly against his mouth. In fact, the vibrations only encouraged her to ride him harder, and so, she continued to whip his balls until everything coming from him was screaming vibrations quickly bringing her to her third climax of the evening.
She whipped his balls harder and harder, until she broke right through the third and into the fourth orgasm. Now, there were loud screams carrying through the apartment, as she passed plateau after plateau. All the while his balls suffered from the whip strokes. After reaching a sixth orgasm, she screamed out, "Oh my god, yes, that was wonderful". Then she finally slumped over across his body, with her face buried between his legs and collapsed.
Though she did not tell him he could stop, he finally relaxed and began gasping for air, as the pressure was released from his face. "My, what a good little cunt licking slave you are", she exclaimed. "Yes, you may rest, now, my pet". And, both of them lay there completely exhausted.
When she finally began to stir, he asked, "Maam, could you please release me, now?" "I really need to pee, bad". "Oh no, my dear", she laughed at him. "You did such a wonderful job; I may never let you go". "But, if you behave and answer a few questions for me, I may help you with your urgent problem. Will you behave", she asked? "Yes, maam", was his reply.
"Good!" "Now, where are the keys to this silly cage, protecting your boyish charms"? "I don't have them", was his reply. "What", she inquired? "Are you locked in this forever? Or, does someone already own this pathetic little worm", she asked, again?
"No maam. I hid the keys at another location, where I could not access them during the evening", he stated. "I hid them away, in the park about a mile from here, which is locked from sunset to sunrise". "This ensured that I would have to endure my torment all evening. Otherwise, I may not have been able to control myself".
"I see", she exclaimed. "We'll deal with that in the morning, then". "Now, what about this leather belt locked around your waist"? "Do we have the keys for that"? "And, what exactly is its purpose"?
"Yes maam, I do have those keys. They are on the key ring which dropped down a little while ago". "Its purpose is to hold a plug in my butt, so I cannot expel it", was his response.
"So, you pervert, you like having your ass filled"?
He looked meekly at her and replied,"Yes maam".
"You have been good and answered my questions, honestly". "I guess I should keep my promise and help you relieve your bladder".
Noticing D-rings attached to the sides of his leather belt, she released his hands, one at a time, and re-attached each to his side, before loosening the ropes which held his knees spread wide. Then, she untied the ropes which held the spreader bar attached to each of his ankles.
He sighed, finally being able to bring his legs together. Then, quickly spread them apart, again, when he felt how tender the insides of his thighs were from the thrashing she had given him, while driving him to provide better service.
Grabbing his arm to steady him, she helped him to stand up, which was not easy in the 5" heels, after being spread wide and unable to move for such a long period.
She held his arm and guided him to the bathroom. Along the way, she commented to him, "You do a much better job of walking in those heels than I ever could".
She guided him in front of the toilet and asked,"I suppose you want to use your hands"?
"Yes please, I also need to sit, due to the chastity device" was his reply.
"Well, I suppose it wouldn't do any harm to give you the use of one hand, since you are still blind and helpless. But, if you try and attack me, I will flush these keys down the toilet. Do you understand?"
"Yes maam, I promise to behave".
"Are you right or left-handed", she inquired?
"Right, maam. Could you also unlock the belt, so I can remove the plug from my ass? It is getting quite sore."
"No", she stated, "You wanted your ass filled, and so, now it stays that way until I say so." "You're lucky I am allowing you to pee. But I am not through with you and don't want to have to play in a puddle of piss".
"Thank you, maam, neither do I."
When he was finished, she helped him stand and re-locked his free wrist to the side of his belt. While guiding him back to the bedroom, she stopped him in the middle of the living room and told him to stay where he was.
Stepping back to get a better look, she commented on his appearance. "You look rather sexy in those stockings and heels. I think I could get used to this. Maybe I should keep you like this all the time and use you as a maid."
"Thank you, maam."
Noticing that while he was standing there, he could not stop clasping his thighs together, she inquired about it. "Is there a reason why you keep clasping your thighs and squeezing your ass cheeks"? "Do you have a problem"?
"I have two rather large problems, maam." "I would really like to cum, but, I know that cannot happen until at least after sunrise." "Also, the plug in my ass is pressing very hard against my prostate. That is making my desire much more desperate."
"I see", she laughed at him. "I guess they are your problems and you will just have to learn to live with them." "Now, let's get you back in the bedroom".
Guiding him back into the bedroom, she centered him against the foot of the bed with his back facing it, again, and helped him lay back down with his knees draped over the footboard. Releasing his hands one at a time, she reconnected them to the chains at his sides, stretching his arms back out, helplessly. Next she reattached ropes at his ankles and pulled his legs back towards his chest and tied the ropes off near his hands. This held his legs spread and exposed his ass.
Then, she searched through the ring of keys until she found the one which unlocked the belt holding the plug in place and laid it out underneath him. Grabbing the base of the big red plug, she began trying to pull it from his ass.
"Ah", he complained. "You're ripping my ass apart. Could you please be careful? It has been in there quite a while and needs to be worked out very slowly. It would help if you worked it out, like you were trying to fuck me with it."
"Interesting", she told him. "Sounds like fun to me. You asked for it." She began to push and pull on the base of the plug until it finally began to slide out. She was amazed at just how large it was and how narrow between the plug itself and the base. It must have been at least 2 inches in diameter and no more than one inch just before the base. She continued to work it back and forth until it finally started to push itself out.
When it was just about ready to pop completely out, she saw it was about 8 inches long. Just then, she shoved it back in hard and fast. This caused him to emit a very loud groan. She chuckled to herself and began fucking him with the plug, just so she could hear the effect it had on him. Looking at his caged cock, she was amazed to see how much juice began flowing from the tip.
Stopping for a moment, she noticed a package of condoms lying on his dresser. Reaching up and opening one, she stretched it over the end of his CB-2000, until it completely covered the cage. Then, she continued pumping the plug in and out of his ass for another ten minutes. All the while, the fluid continued to flow from the eye of his cock, slowing collecting inside the condom.
"Well, that was fun", she commented as she finally removed the plug. "I thought that would milk you dry; but, you just keep flowing". "Time to move on to bigger and better things". She reached for the ball gag she had removed earlier and held it against his mouth. He kept his mouth closed, until she reached over and twisted hard on his nipple. When he opened his mouth to scream, she shoved the ball back into his mouth and began buckling the straps back in place. "I don't want you disturbing the neighbors with what I am going to do, next", she told him.
Then, she reached up to the dresser and picked up a 9" dildo and harness, he had laid out earlier. Commenting to him, she said, "Since you enjoy having your ass stuffed so much, you should really enjoy this". Grabbing a bottle of lubricant which was laying next to the dildo, she inserted two fingers into his ass and spread them open. She placed the tip of the lubricant bottle inside his ass and began squeezing it until she was satisfied he was well lubed for her next assault. With his legs pulled back as they were, the lube just flowed deep into his open hole.
Placing the bottle of lube back on the dresser, she picked the dildo back up and noticed there were actually two dildos attached to the harness. One faced out for fucking someone and the other faced inward, to stimulate the fucker. She thought to herself,"This is going to be better than I imagined".
Carefully, she began inserting the smaller dildo inside her virgin hole. She was still dripping from their previous engagement, so it slid right in without problem. Pulling the straps around her waist, she continued to buckle them as tight as possible. She relished the feeling of the dildo pulled deeply inside her dripping cunt. Before this, she had only experienced her own fingers and they weren't a quarter the size of this intruder. She began to appreciate what her neighbor must have experienced with that plug so deep in his ass for so long.
She chuckled to herself, "Just wait, my little panty slave".
Kneeling on the bed between his spread legs, she placed the head of the larger dildo against his puckered rosebud. She slid the head inside and held it in place. Reaching up, she grabbed each of his nipples with a hand and began pinching them, harder and harder. When he began moaning into the gag, she plunged the dildo forward in his ass, burying it to the fake balls at the base. He moaned long and hard into the gag, and raised his head up, straining the muscles in his neck, at the sudden force of her thrust.
When he finally settled back down, she lay down on top of him and began a slow, rhythmic thrust in and out of his ass. With each stroke, she pulled the dildo almost completely out, and then, slowly pushed back into the depths of his tender hole. With each thrust, he grunted into the gag.
As the dildo inside her began to work its magic, she began to care less about what this act was doing to her partner. Her only concern was her own pleasure. After all, this was her first experience with actual intercourse. As the pleasure built inside her, she began thrusting into him harder.
Slowly, she began to feel another orgasm building up inside her. Her thrusts gained in momentum. With each thrust, now, he just lay there tossing his head back and forth and pulling at his restraints. You could hear the air rushing out of his nostrils each time the dildo was rammed into him. It was like she was hammering his diaphragm with each stroke.
As she neared her climax, her hips began working more like a machine than a human. The strokes continued their full length, deep in and out of his ass; but, they continued to increase in speed, like a steam locomotive running out of control. She was moaning hard, now. But, he was emitting one continuous howl. She thought to herself, that if not for that gag, the neighbors would not need to call the police, he would probably be heard all the way down at the station.
Suddenly, the strokes became very short, but very powerful. She was reaching her orgasm. She began yelling at him as she hammered his ass.
"Take it you worthless bitch. I don't need that pathetic little locked up cock of yours. I'll just fuck your ass into oblivion with this wonderful harness you left out for my pleasure."
With that, she gave him one final thrust and collapsed on top of him. She wrapped her arms over his head and laid her head alongside his and licked his ear. They both lay there panting and quivering, for the longest time. In moments, they both passed out.
As she finally drifted back down to earth, began to remember where she was and noticed that the sun was starting to rise. She raised herself up and reached down in between their groins. Feeling around the base of the dildo which was still buried deep in his ass, she began prying it off the harness attachment.
When it was free, she pulled herself up off of him while holding the dildo inside. Once she was off the bed, she pulled the straps from his chastity belt back up and used it to hold that 9" dildo inside of him. As she buckled the straps, he began shaking his head back and forth. "Ugh, ugh... ugh, ugh", she heard him complain. She pulled the straps as tight as she could, burying the dildo deeper in his ass than it had reached during their long previous session. As she closed the lock, sealing his fate, yet again, she told him, "Oh yes, my little slut, I have one final torment for you, before we settle down to get some rest.
She unbuckled the gag and pulled it from his mouth with a sudden plop. When it sprung free, she placed her lips upon his and drove her tongue inside his mouth, kissing him passionately, for several minutes. Then, she rifled through the keys to find the one which unlocked the collar around his neck. With that unlocked, she pulled the hood over his head and removed the blindfold. She bent down again and began licking the tears from around his eyes and cheeks.
Pulling herself away from him, she asked, "Do you have anything else to wear over the top of all this lingerie, to finish dressing as a woman"? "Yes maam", he replied. "W-w-w-why", he asked? "Because you will look awfully silly walking through the park to get your keys, dressed in only your lingerie and heels". She stated. By now, he knew it was best not to question further; but instead, he had better just co-operate.
She freed his legs, then, one at a time released his hands and re-locked them to the sides of his belt. "My god, you're a mess", she commented to him, "I sure worked you over pretty good". "I better get you cleaned up so I can finish preparing you for our little trip to retrieve your keys". "Go into the bathroom so I can wash your hair and face".
As she watched him walk towards the bathroom with that huge dildo still buried in his ass, she spoke to him, "This is going to be an interesting trip. I love how you swing your ass with it stuffed like that and wearing those sexy heels".
When she finished cleaning him up, he told her where she could find everything she needed to complete his transformation. She had him pull up a chair in the bedroom, while she went through his closet collecting everything she needed. She was surprised at the collection of make-up, and the gorgeous red wig. In the back of his closet, she found a pretty blue sweater and a short black skirt.
She freed his hands and made him promise to behave again. She also promised that this was the finale of their encounter before they would settle down and get some sleep. Tossing the sweater and skirt to him, she allowed him to dress himself and then sit back down in the chair so she could fix his face.
Reaching into his make-up bag, she found a set of long false eyelashes and decided to apply them, before proceeding with the rest of his make-up. When the lashes were in place and the glue was set, she applied a layer of foundation and powder. Next she took her time with his eyes, being careful to get them looking very feminine. Then she applied a layer of long-lasting lipstick and topped it with a coating of gloss. As a finishing touch, he had a pair of clip-on earrings and matching necklace.
When she was finished, he could not believe what he saw in the mirror. He looked so good; he would willingly fuck himself, even though he was really a man. "How did this plain looking woman manage such a great job of feminizing me", he wondered?
"Now", she told him, "We better get going before too many people start flooding into the park for their morning exercise". "I will drive, since I can imagine it would be rather difficult in those skyscraper heels". Locking the apartment behind them, as they reached the front door of the building, he stopped for a moment.
Reaching behind himself and under his skirt he re-adjusted the dido in his ass with a loud grunt. Pulling the skirt back into place, he looked at her and said,"Ok, let's get this done". But, he could not believe he was going out in broad daylight on a Sunday morning in full female attire, while forced to endure a huge pole up his ass, no less. Yet, he could feel his cock continue to leak fluid into the condom which was still covering his chastity device.
As they approached the park, he explained to her where he had hidden the key. He couldn't believe the bitch parked in the farthest space she could, from where his key was hidden. She was not making this easy on him. But, at least, she stayed right by his side and held his hand like two lesbians out for a walk in the park.
As they approached the hiding place, they noticed a couple jogging towards them from a distance. She stopped and turned him so his back was facing them, wrapped her arms around his waist and planted a deep passionate kiss on his glossy ruby lips. She also reached lower and fondled his ass, lifting his skirt slightly, as the couple passed by, flashing his thighs and stocking tops to the couple.
After they passed, she saw the guy turn around and start jogging backwards for a moment. When she saw this, she winked at him and threw him a kiss, causing him to trip over his feet and fall backwards. The guy's wife stopped, turned and yelled at him, "Get a good enough look"? He looked back at the apparent lesbian couple with a red face, picked himself up and ran off to re-join his wife.
They both laughed as the couple ran away. He pulled his neighbor back into him and gave her another big kiss and then they turned their efforts back to the task-at-hand. Finding the hidden keys, she made him turn them over to her, with the threat of her tossing all his other keys into the lake if he did not comply. With that settled, they strolled back toward the car, hand-in-hand, like two giddy school girls.
Half way back to the car, she pulled him off the trail and into a picnic area. Next thing he knew, she pulled a length of rope from her purse and told him to cross his wrists in front of him. She tied his wrists and had him bend over the top of a picnic table, securing his hands underneath the far side, so he was stuck there with his ass sticking out from under his skirt. But, she was not done yet.
Next, she lifted his skirt, tucking it into the waistband and pulled a leather belt from her purse. She looked at him and said, "If you make just one sound and attract any attention, I will leave you hear, just as you are.
She doubled the belt and began blistering his ass until the cheeks turned purple and blood was about to break through the skin. Then she reached underneath him and unlocked the belt which held the dildo. Once it was unbuckled, she let it drop to the ground and the dildo slow began to creep out of his ass. Grabbing the base, she began pulling it out until the head sprang free and then ramming it back in deep. With his legs kicking up as much as they could in the heels, he fought hard to keep from making any noise.
She must have kept this up for at least 20 minutes and he began to wonder if maybe she was waiting for more joggers to pass, so she could offer his ass to them. But, finally, she removed the dildo, pulled a plastic bag from her purse and dropped it inside. When she picked up the leather belts and dropped them in with the dildo, he suddenly felt relief, that at least he would not have to make the return trip home, with that monster buried in his ass.
Untying his hand, she rearranged his skirt and checked his make-up. When she was satisfied he was presentable, they headed back to the car. As he settled into the passenger seat, he commented," God, it feels good to be able to sit without that thing pressing against my tonsils".
When they returned to his apartment, she told him he could remove the sweater and skirt, and relieve himself; but, keep everything else as it was. He did not feel it wise to argue, while she still held all his keys.
When he was done, she was waiting in the doorway, where he had a chin-up bar mounted near the top. "Give me your hands", she ordered. And, she proceeded to tie his hands in front and then string the extra rope over the bar. Next, she ordered him to spread his legs and proceeded to tie his legs back to the spreader bar, so he could not close them, finishing off by tying the extra rope from his hands, to the bar, so he could not pull them down.
Reaching between his legs, she massaged his caged cock. Then, turning to walk away, she said, "I'll see you tonight".
He yelled at her, "Don't you dare leave me here like this after everything I have gone through, already.
She turned and looked back at him. "Oh, really? Did you forget who is in charge"? She walked over to his kitchen counter and pulled out his blender, plugged it in and removed the lid. As she dangled the keys to his chastity device over the open top he screamed at the top of his lungs, "Nooooooooo"!
"Gotcha", she spoke out. Then, she returned to his feet and knelt between his legs. Reaching up, she slowly removed the bloated condom from over the top of his cage, being careful to allow all the collected juices to run back into the latex balloon. Looking down, he could not believe it was possible for his cock to release that much juice in the last few hours the condom had been covering his cock. It was so swollen; there must have been enough to fill a small glass.
As she stood back up, she held the condom in front of his face, so he could get a good look. She looked into his eyes and told him, "Be a good little slut and open wide. All good sluts swallow". He clenched his ruby-coated lips closed and shook his head. "Ok, we'll do this the hard way", she threatened him. Holding the condom with one hand, she reached down between his legs and grabbed hold of his balls, squeezing hard, until he finally opened his mouth to scream.
At that moment, she placed the open end of the condom in his mouth and proceeded to wring every last drop of his collected juice into his mouth, watching him gulp as he tried to swallow it all. When she could not squeeze out any more, she turned the condom inside out and made him lick up every last drop. She even placed a couple of fingers inside of it and fucked his mouth, until he completed this difficult task.
When he was finally done, she knelt back down between his legs and began to remover the torturous device from his cock. As swollen as he had become from his night-long ordeal, this was not very easy. She had to be extra careful when she found the spikes sticking up, that had been filed into the ring of the KSD-G2, which he had used to ensure he was unable to pull his cock out of the device.
When she had extracted his pole, she left the ring wrapped tightly around the base of his cock and balls. His cock was swollen and purple and when he looked down at it, he thought it looked twice as fat as normal. Reaching down, she untied the rope, which she had attached to the spreader bar and threading the rope through the base ring, she pulled it tight between his legs, until he was standing on his toes to relieve the pressure on his arms. Once she was satisfied with his predicament, she tied it off behind him.
Taking his cock into her mouth, she pushed as far into her throat as she could, running her tongue all around his shaft and swallowing constantly, to massage his cock. When she had him thrusting into the back of her throat as much as he could, bound as he was, and she could not get any more of his length inside, she pulled him back out and began running her tongue around the length of his cock. As she felt his cock begin to twitch, she changed technique again and fucked her mouth with his cock, until she felt he was ready to explode. When he screamed to her that he was cumming, she buried him deep and held him there collecting every last drop of his precious seed.
Once he finished, she stood up and proceeded to give him a deep passionate kiss, exchanging his sperm, from her mouth into his and making him swallow every last drop.
When both of their mouths were free of any remnants of his seed, she untied him and suggested they curl up together and get some rest. "Once we are rested, I want to finally feel you inside me", she told him.
Curling up in bed with her arms wrapped around him and her hand resting on his now flaccid cock, she whispered in his ear, "My turn next"? And with that, they drifted off into a deep sleep.