It was set than. Jackson had finally done it. It must be for real now... now that he had actually set an actual date and time. As he sat in front of his computer in nothing more than a robe that lay wide open, he hit send on his e-mail. He could not think of a time in recent memory that he was more sexually aroused. Casually, as he did thousands of times before, he took a pump of the skin lotion that sat next to him into the palm of his hand and rubbed his rock hard cock. Ten seconds later, he had cum all over his naked chest, wiping the excess with the inside of his robe.
Jackson had recently discovered Craigslist. It opened up a vast world that he could only have fantasized about prior to this episode. Now it had become more of a possibility, and in this case, even a reality.
Through his exploration of the website, he stumbled upon the "men seeking men" section where just for kicks one night he typed the word "bondage" in the search bar. Scores of ads came up for men looking to enslave other men in various forms of bondage and perform on them acts such as flogging, water sports, simulated rape, fisting, etc. while tied up and helpless.
He could not believe his eyes. At 29 years old he had always fantasized about these very scenarios from a very young age. He could remember becoming as a young boy from watching cartoons of his favorite superheroes that were captured and bound. Unfortunately, he could not possible act them out as he had no idea how to do so. But this was so easy. Through the anonymity of his computer and fake e-mail addresses he created for this very purpose, he could screen ads until he found one that fit his fantasy. As he read ad after ad, he replied to several but none really seemed "perfect".
In an attempt to take matter into his own hands he finally posted an ad of for himself. He titled it "Sub Slave Looking for Master". It read:
29 YO Male 6' 155 GL surfer type, blond hair, athletic, 7" cut, completely hairless, looking to be stripped naked and bound for your desire. Into kidnap scenarios, interrogation, etc. bound to be whipped, tortured, forced oral, raped (safe), or whatever you deem fit. Please send a pic.
With this ad alone, he received more than thirty replies, mostly just guys looking to get lucky for one night, many who were just giving shout out with no actual motive but that. As he sifted thought the replies, one caught his attention. It was from a forty seven year old male who was a self professed "Bondage Master." Through his e-mail, he invited Jackson to come over to his dungeon for a session. He further specified that once inside he was to strip naked, be evaluated and than bound. From there he would be led to his dungeon which contained a multitude of bondage equipment, including a steel cage and a saw horse. The rest would be a surprise. Through his e-mail, the author also stipulated that he must be freshly shaven from neck down and be ready to spend the night. Attached was a nondescript picture of a naked middle aged man, slightly tone with a bit of a belly. Also attached were pictures of a several young men, bound naked in various stages of bondage.
Jackson once again could not believe his eyes. This seemed perfect. Though a rational person would have been wary, Jackson was thinking not with his head but as is too often, with his balls. He quickly shot back a reply and set up a date and time for Saturday afternoon. The session would continue though Sunday morning. This he thought would be great since it would allow him to rest up on Sunday for work on Monday.
On the other end, the Master could not believe his luck as well. This was almost too easy, like "shooting fish in a barrel." All he could think was that this guy was actually going to just walk into his house, a total stranger he met on the internet, and allow himself to be bound helpless for his pleasure. This was way too easy indeed.
The morning of their scheduled meeting, Jackson awoke at the break of dawn. Usually he liked to sleep in on the weekends, but on this particular morning he was far too excited. His head was racing. One of his most intimate sexual fantasies was about to be realized. Jackson did not see himself as a homosexual. He was actually quite the opposite, a ladies man of sort. His surfer boy good looks and his lucrative high powered job assured that he never had to work too hard for female companionship.
His foray into bondage and subsequent encounter with a man was not a sexual one, though sexually exciting, he rather saw this as an exercise in ceding control of his life. In his high powered job, he was the boss, always telling people what to do and when to do it. This session to being stripped naked and allowing a stranger to tell him what to do, or more importantly, forcing him to perform acts he would never think about doing was more a therapy for him, a way of taking a vacation from his life no matter how temporary.
Although the meeting was not scheduled until 1:00 P.M. at the Master's house, he wanted to start preparing now. As instructed, he got into the shower as he did every morning, and began to shave himself from neck down. It was probably a combination of the way his freshly shaved body felt and the nervous anticipation of the afternoon, but Jackson grew rock hard. Unlike previous mornings where if the desire hit him, he would jack off in the shower, he refrained from doing so since he wanted to maintain a high level of sexual anticipation.
Just as he was about to finish his shower, Jackson remembered one important piece of business. Sitting atop his sink, laid a plastic bag from the local drug store containing a new enema bag he had picked up several days before. Knowing intuitively how these things worked, he had actually never used one before. After reading the instructions and fumbling with the assembly, he proceeded to fill the bag with warm water from his sink. Jackson felt the best way to go about this would be to use it in the shower, just in case there was any spillage and than run to the toilet to relieve himself. He hung the bag on the shower nozzle, and than laid on his back propping his butt up with his feet, using the side of the shower as a purchase. Slowly his slid the nozzle in his butt, noting how weird this felt. Jackson's asshole had always been an exit only. He had a girl once try to stick her finger there during a love making session to which he pushed her hand immediately after realizing what she was attempting.
The warm water filled his bowels slowly. He could feel the water tricking down the length of his bowel, slowly distending his belly in doing so. Several times he felt waves of cramps come and go. He knew this to be natural and that they would soon pass. Before he knew it, the bag was empty, it contents more or less save for a little leakage, in his bowels. As he lay there in at the bottom of the tub, now in a modified fetal position, he tried with all his might to hold in the water. Wave after wave of cramps continued to fill his bowels, until he could not possible hold it any longer. Instead of letting this shitty water fill his shower, he got up and out of the tub to sit on his toilet so that he could let it all go. A combination of water and shit left his bowels with amazing force and speed. He had never felt this sensation before. It was like having diarrhea multiplied by ten. When he was done, he decided to perform the task two more times. He showered again and sat nervously anticipating his meeting. The hours or even minutes could not tick by fast enough.
An hour before his meeting, he changed out of the bath robe he had been lounging in throughout the morning onto the clothes he was to wear. Knowing he was going to be stripped naked upon arrival, he was torn between wearing something casual versus wearing something the showed a little effort. He decided on a pair of expensive designer jeans, and a polo shirt. This way he did not look like a bum but also not like he was attending a wedding. The most important aspect of his attire was not what showed on the outside but underneath, mainly the type of underwear he wore. Jackson had actually given this much thought. Between boxer brief, boxers or something a little more provocative, he decided on the provocative, a men's g string he had ordered on-line with a mesh pouch that hid very little. The pouch barely covered his cock and balls, and having never worn a thong before, the sensation of a string sliding between his butt cheeks and resting on his asshole created great sexual desire. As he put it on and slid the jeans over his freshly shaven legs and exposed ass, he could not help but feel an erection coming on once again. As before, he suppressed this sexual desire and just grabbed his keys so that he would not be late for his meeting.
The Master's house was about one hour away by car. One of the things that influenced his choice was proximity. The last thing he wanted was to serve someone locally and than run the risk of running into them somewhere in town. By choosing someone an hour away, he felt that this would greatly diminish his chances for a random run-in.
As he drove up to the address the Master had provided, he noted it was a nice but otherwise nondescript house in an upper middle class neighborhood. This was not one of those often cliché gated houses with a long winding road leading up a hill to a mansion that was often described on so many novels or short stories of this theme. It was still a good sized house though, probably if Jackson had to judge from its exterior, a two story house with four or five bedrooms and a three car garage.
Nervously he sat in his car with the engine shut off, trying to collect his thoughts before the walk to the front door. There was so much going trough his mind. Not only did he have butterflies, but felt like they were going to burst through his stomach any time now. With a clammy hand, he reached for the door and slowly got out. Even though he parked not more than thirty feet to the house, it seemed like an eternity has he placed one foot after the other on his way to the front door. When he finally got to the door, he paused for one last moment before ringing the doorbell, thinking to himself, "There's no turning back now." He rang the doorbell and waited.
Through the door he could hear faint rustling as person on the other side came to the door. After a few clicks of the lock, the door opened.
"Master?" he inquired.
"Yes, you must be Jackson. So nice to finally meet you in person. Please come in." Although he had never actually done this before, the greeting was not what he expected. He expected the Master to assume his role right away, and not ask him in as if he were a guest coming over for Thanksgiving Dinner. Moreover, the Master's appearance did not resemble the picture he had sent on Craigslist, in fact, he now believed it to be a fake. Before him stood a middle aged man who was slightly overweight, with slightly graying hair and an avuncular face. He almost seemed too nice to be a Bondage Master. The Master was dressed extremely casually, in khaki's and a button down shirt and wearing house slippers.
What threw him off even more after inviting him in was when he asked him to have a seat on his couch. The inside of his house was well decorated, best described as a cross between Ethan Allen and Crate and Barrel. Jackson sat down as the Master offered him something to drink to which he politely declined. He was just too nervous.
"It's such a pleasure to meet you," the Master started. "Before we get started, I've been doing this for twenty years. I have a great day planned for you. The only thing I'd like to do is establish a safe word. The rest, you'll have to just trust me, if that's OK with you."
"That's fine with me," he blurted. "As for the safe word, I guess we'll just keep it simple. How about 'stop'."
"Stop it is than". With that the Master stood up, warmly motioning with his hand for Jackson to follow. He led him down a hall through the kitchen to a door Jackson thought was a closet. He opened the door leading to a flight of stairs going downward. "Let's go down into my playroom," he said invitingly. With that Jackson followed him to what appeared to be a moderately sized room, where the sawhorse and steel cage he had discussed in his initial e-mail sat. The only other obvious article in the room was a twin bed and what looked like a whipping post. Other than that, there were various cabinets and dressers where the "toys" were likely stored but out of immediate sight.
"Please," said the Master in a calm tone. "If you don't mind, let's get started. Turn around and face the wall and get undressed."
With that Jackson did as he was told. First he pulled his Polo shirt over his head, laying it neatly on the bed next to him. He than removed his shoes along with the socks, placing the socks on top of his shirt. Slowly he unbuttoned his jeans and started sliding them down exposing his g-string.
"Nice," said the Master. "On second though boi, why don't you keep those panties on. They really frame you ass nicely." While Jackson was still undressing, he could hear the Master fumbling in the cabinets, but because his back was turned, he could not see what he was actually doing.
"Now, please stay turned around and place both you hands on top of your head," instructed the Master as he slowly approached Jackson. Jackson could feel his warm breath as he walked up right behind him. Slowly the Master, with Jackson still assuming the position began feeling him up in a gentle and sensual manner, first around his chest, working down the front of his stomach, towards his ass and than brushing ever so slightly on his panty contained cock, bringing it to life.
The Master, while Jackson was still facing away from him, led him with a mere hand to the small of his back to the whipping post, a phallic like object made of wood in the middle of the room that extended to the top of the ceiling with steel manacles that dangled from the top as well as laying invitingly at the bottom. Jackson thought to himself that this object actually looked like an old tree trunk, debarked and sanded smooth to remove the possibility of splinters.
"Please relax your arm," he said has he guided Jacksons left wrist above his head and fastened the manacle around his wrist. He soon did the same with the other.
Jackson did not see what he did next, but the chains attaching the manacles soon began to shorten into this wooden object he was pressed against with his near naked body until his arms could be stretched above his head no further without him going onto his toes. In fact, he actually intermittently went to his toes to help lessen the tension he felt on his upper back and shoulders.
"Are you feeling OK?" inquired the master.
"I'm fine," blurted Jackson.
The Master than gentle ran the palm of his hand seductively from Jackson's shoulders to the back of his legs, paying particular attention to his ass. "Are you ready to be punished boi?" he inquired in a slightly more assertive tone than before.
With that, Jackson soon felt his back lightly paddled with what felt like a riding crop. It stung slightly, but by no means painful. Jackson even thought to himself that he wanted to be struck a little harder.
The Master proceeded to paddle Jackson with the crop for another minute. All the while, Jackson could only speculate what the Master was doing since his face was pressed snugly on the post. What happened next was completely unexpected. After a thirty second interlude from the paddling, Jackson heard a whoosh and than a pain on his ass that could be described as the most painful experience of his life. It was so unexpected and dramatic, he actually grunted as he threw his head back. What he was unable to see was that the Master had exchanged the crop for a cane, much like the canes they use in Singapore to punish criminals. The initial caning had not only left a red mark, but a small gash in his left butt check that was starting to ooze blood.
Before he could collect his thoughts, he felt yet another swish land square on his ass, once again, causing his head to throw back. He panicked. The only thing he could muster was the safe word. "Stop!" he garbled though the sheet of pain that enveloped him.
The Master, completing ignoring his pleas continued to hit him with the cane four more time, twice on each ass. By the time he stopped, Jackson's ass was crisscrossed with six deep gashes, all breaking skin, with blood seeping out the wounds.
Jackson now hung limply on the pole, had not the shackles around his wrist kept him from falling, he most likely would have curled up into a ball on the floor.
"Is this what you were expecting," inquired the Master in once again a calm inviting tone.
"Please, what are you doing? Please let me down." Jackson's face was wracked with pain, his whole body glistening with sweat.
"Well that would take all the fun out of it. Boi, I can't believe you agreed to all of this. When I saw your ad on Craigslist, I didn't think you would go through with it. The rest is just icing on the cake. Let me tell you something. You're mine now. The walls are soundproof. I'll merely move your car into the garage so that there will be little trace of your being here until I decide what to do. No one would ever suspect you being here, and from what I can tell, I'm willing to bet you told no one you'd be here."
Jackson was in disbelief. He was helpless, in the hands of a madman. Moreover, he had volunteered for this. His mind was again racing, not from excitement as was the case this morning but more out of fear and hysteria. This was all under his free will. This man could very well kill him; at the very least permanently maim him. If he had it to do all over, he would promise never to do this again. But that was not an option now. All he could do was wait, and hopefully not be injured too severely.
Even if he were to be released, the police were not an option, considering the overall embarrassment he would face by not only his friends, family, and coworkers, but to the community as well, considering a story like this would surly make the local new. This was certainly to use a popular phrase in his line of work, a "lose lose situation."
As the master was saying this to Jackson, he casually walked up to him and reached for his balls from between his legs, placing his hand under his g-string and squeezed with all his might causing Jackson to go into light convulsions. "Arggggghhh!" he screamed. It felt like his balls were on the verge of popping. The pain radiating up into his abdomen was unbearable. After about ten seconds he finally let go. As he did this, he casually grabbed the pouch of Jackson's g-string, and with one motion, ripped the entire thing from him so that he was now chained completely naked on the post. Jackson's balls felt like they were going to explode still, even though the Master had released the pressure.
The Master next adjusted the tension of the manacles once again on the whipping post, raising Jackson's arms slightly higher so that now he had no choice but to be on his toes. He than attached the leg irons to his ankles so that now he was more immobilized that before. Once again, he struck him with the cane, this time on his back, and once again eliciting a primal scream that far surpassed the ones before. The pain was so overwhelming that Jackson pissed himself on the final blow. He probably would have shit himself as well for it not been for the enema he gave himself before coming.
"Stop please. Let me down. I've had enough." Jackson was crying now, sobbing uncontrollably.
The Master responded with a brief, "No."
"Let me tell you something," he followed. "From this point on, you are no to speak. I could gag you but as I said before, the room is soundproof. Also, I want to hear you scream to the best of your ability. You're here until I say so, so get used to it. If I here you utter another word, you will be amply rewarded with ten more strikes of the cane. Got it? Now I've seen you pissed yourself. When I finally let you down, you will get on the floor and lick it clean with your tongue."
The Master had everything scripted out. He had prepared for this moment since his first communication with Jackson. In silence now, not wanting to tip Jackson off the tortures that awaited him, he decided to stop speaking to him all together. The element of surprise would in itself be part of the torture, part of his devious plan.
Once again he reached into a drawer and approached him once again. In his hand was a jar of Icy Hot to which he placed his hand and started to smear it in all of the cane marks. At first Jackson almost found it soothing, kind of cool, but within moments he realized what was happening as the heat started to escalate. Before he knew it, the heat was of unbearable levels. "Arrrrrhhh," he cried. Thinking he could possibly shake off the Icy Hot from his body, he started writhing uncontrollably. Sweat started pouring down his face. As he was doing this, he felt the hand of the Master approaching his anus and balls from behind. He was smearing a big glob all over his dick and balls and than lubricating his asshole with it as well, sending him into even a more intense level of pain. The ball and cock felt literally like it was on fire. Jackson even questioned to himself if he skin was indeed being seared off.
As he hung there, thinking the pain could get no worse, the Master calmly walked up to him and cocked his fist back and with all his might, slammed it into his exposed kidney. He repeated it to the other kidney. A huge "oomph" left Jacksons mouth. Even though the Master had instructed him not to speak, he screamed for him to stop. "You're killing me"
Silently, the Master picked up the cane once more and without uttering a word, slammed caned him on the back of his legs ten times as previously promised. He followed that up by smearing Icy Hot into those wounds. Jackson was hysterical at this point, writing now so severely, it looked like he was smashing his forehead into post.
"Hang in there," he softly whispered. "What would I be if not a man of his word? When I say don't talk, I mean don't talk."
The Master once again went to a drawer and pulled out an object. This time it was a very large butt plug. As he approached Jackson, who was now a babbling mess, using the Icy Hot as lube as he smeared it all over the tip. Jackson could not see what he was doing and in fact was completely oblivious to his surrounding as since his pain was overwhelming. He felt the tip of the butt plug at resting on his pre-lubed asshole and than felt it ever so slightly begin to broach the opening. Slowly, his asshole began expanding to fit girth to the point he felt it could expand no more. Unfortunately, for him, only a fraction of the plug was in him. He still had the thickest part to go. As the Master slowly inched the butt plug into his virgin asshole, Jackson thought for sure his ring was going to rip. The searing pain was intense. To make matters worse, the ripping was creating new fissures for the Icy Hot to spread. No only was he being torn apart, he felt like he was being burned alive as well. With one final pop, the butt plug was in. As much as he tried to expel the foreign invader, he could not. He thought if he wildly bucked is hips, at least to the level his tight bondage allowed, it would some how ease the pain for the foreign invader.
Once again the Master reached between Jacksons legs from behind and grabbed his balls. Squeezing as before with all his might, he held the pressure for a full twenty seconds this time. "Arhhhh!" screamed Jackson once again. His eyes, emblazoned with agony, he tried to get free, like a trapped animal, as he writhed like never before. Unfortunately, this only cause the steel manacles to dig into his wrist and ankles, causing small trickles of blood to form where they were attached. He was going no where.
The Master, during the entire time was suppressing his own sexual desire. After all, this was his fantasy as well. As Jackson tried desperately to collect his thoughts, rationalize this very irrational situation, the Master himself began stripping himself of all his clothing. He finally walked up to Jackson from behind and pressed his naked body upon his. He placed a condom on his rock hard cock and in one fluid motion, removed the butt plug from Jacksons now stretched asshole and placed the tip of his penis at the opening. He would have loved to have fucked him bare back, were it not for the Icy Hot coatings Jackson's bowels. Fortunately for him, their heights were more or less similar, and the Master found if he hunched down slightly, he could rape Jackson's asshole without much adjustment. With that, he slowly began slipping his cock into Jackson.
"Oh shit," he thought to himself. "He's so fucking tight." Slowly, and methodically, he began pumping, slowly at first and than working himself into a comfortable rhythm.
On the other end, amidst the sea of emotion he was feeling, Jackson now realized he was being raped. He did not anticipate the pressure he felt from the actual act, almost like he was being skewered. Subconsciously, through a combination of the pain from the rape and the overall pain he felt from the entire ordeal, he began grunting in rhythm with each successive thrust. Jackson thought he could escape the rape by pressing his hips into the post. Unfortunately for him he could not.
The Master on the other hand was working himself into a nice rhythm. He felt the orgasm building until finally; he felt he could no longer hold his seed. With a few final thrusts, his cock began spasming, at which time he pulled out, removed his condom, and came all over Jackson's naked ass. This was by far the hardest he had cum in the past year.
He was ready for a rest now. He had only one more thing to do to his willing slave. Jackson, completed dejected, rested his head on his left shoulder. The tight bondage would only allow movement of his head and neck. He hung there with cum dripping down his ass towards the back of his legs. The level of pain and humiliation he felt at this point was beyond belief.
As he had done a half dozen times before, the Master reached into one of his cabinets to retrieve and object. Unlike the previous occasions where he shrouded his intent in mystery, this time he walked up beside the tear stained face of his prisoner and held up what could best be described as a cattle brand. "I got this while vacationing in Montana. A buddy of mine uses it to brand his cattle."
A flood of emotion overcame Jackson that could best described as hysterical. The very thought of being branded was beyond comprehension. Like a trapped animal, he began bucking wildly. If he could, he would have chewed off his hands and feet to escape this psycho and what he was about to do to him. This whole time, he was able to rationalize that the marks inflicted onto him would more or less heal with minimal scarring. This was different. This would be impossible to explain even if he were to get out of the predicament.
The Master plugged the branding iron into the socket and waited for it to heat up. In an oddly gentle manner, he took the back of his hand and gently stroked Jackson's face, trying almost to calm or even soothe him. Once again, he pressed the button that tightened his binding raising Jackson to the point where his toes barely touched the ground now. "I think we're ready."
"Hold still please. I wouldn't want this to smear." Jackson could see the end of the brand, the letter "S", grow red hot.
Ignoring Jackson's pleas, but noting that he owed him another ten strokes with the cane, the Master walked up behind Jackson and placed the branding iron one inch from the small of his back, the spot where girls would get a "tramp stamp". He was really serious earlier when he stated his desire for a perfect brand. He did not want Jackson to move. In order to distract him, the Master once again reached from behind between his legs and squeezed Jackson's balls with all his might. This time he held it for a full minute. A blood curdling scream emanated from Jackson mouth. He felt for sure this time that his balls had ruptured. Just when he thought the pain could not get any more intense, the Master release his balls, and while still distracted by the pain, he pressed the brand to the intended target. As much as Jackson fought, he could not escape the brand. Between his tightly shacked wrists and ankles, and the force of the brand pushing him into the post, he was all but immobilized. The smell of burning flesh soon filled his nose, not to mention the excruciating pain from the third degree burn he was suffering through. The Master held to iron to Jackson's skin for a full ten seconds. For Jackson, this was the ultimate sensory overload, wave after wave of pain. Finally, his body could take no more and he passed out.
The Master stepped back and admired his work. Before him lay a bruised slave who earlier had what could be described as an impeccable body. The Master had used it as a canvas for his masochism. It was now riddled in deep cane marks, bruising, and to top it all off, a two inch "S" branded into the small of the back. This was a job well done. A masterpiece.
The Master was exhausted now. Once again, he hit the controls to his whipping post, but this time all the manacles loosened to the point that Jacksons ravaged body fell to the floor in a heap. He undid all the bindings and handcuffed Jackson's hands behind his back. He dragged his naked form into the cage that he had shown him in his first e-mail, placed a padlock on the door and went up stairs for a drink. Inside the cage, Jackson's handcuffed naked body lay unconsciously. The master needed to rest up for round two.