Mr. Trample Fantasy
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The Care Taker
🕑 Added 2022-07-14 15:43:04 +0000 UTCBill Jones was the caretaker for St Josephs Sixth form college for girls and had been for the last ten years. He loved his job and would do anything for the girls. All of the girls were between 17 and 19 years old and all of the teachers were female.
Bill had a trample fetish that no one new about and used to spend most of his days fantasizing about the girls and teachers walking over him without knowing he was there. If anyone ever knew of this fetish it would likely cost him his job however.
Bill was not highly paid but considering he had his own apartment within the school this was not such a bad deal. As the girls came in to college he would peer under the door and watch all the shoes go by, often becoming aroused at the sight.
About five years ago Bill was having problems with the plumbing in his bathroom which was set lower than the rest of the apartment. It was clear that a pipe was leaking but it was beyond the wall behind the toilet. Bill looked at all of his options and decided he had to remove part of his wall to access this. He gained permission of the Principle and set to work one weekend when the college was closed. As the wall came down Bill realised that behind this was the dead space under the floorboards of the school and off he went to investigate. Before long Bill realised that he had access to the entire ground floor of the college under the floorboards and he could almost stand full height as this was a very old design for a building. After a while Bill decided to walk round the college and visit all of the rooms with a hammer and a few nails in tow. Each teaching room he entered he would estimate where the lecturer would be standing and pulled back the carpet and drove a nail through the floorboards. He then moved to a random desk and did the same where he thought the student’s feet would be. Bill followed this up by drilling one inch holes next to the nails and scuffing the underside of the carpet enough to see through without anyone being able to see the holes.
It took a full day but Bill managed to cover every room on the ground floor including the dining room, staff room and library. He went back to his apartment and entered the dead space again and proceeded to fill all the holes with pieces of wood that could be removed as required by holding them in place with a board that swivelled. Bill was able to use the nails as a marker to find his holes so he could have the view he’d always dreamed of.
The next day Bill fixed his plumbing and replaced the wall with a piece of wood that was hinged to allow him access to the space under the college. Once finished Bill painted this secret door the same colour as the wall and stepped back to admire his handywork, brilliant - you could barely tell there was a door there.
On Monday Bill hurried about the school doing his usual jobs and had finished his workload by 11am. He approached the Principle and told her he would be busy this afternoon checking all the plumbing but if she needed him then she just had to ring him and he’d be close enough to answer the phone.
Bill returned to his appartment and entered the dead space armed with a plan of the college. Above him Bill could here the useal sounds of talking, laughing and walking. He approached one of the nails and stopped. He listened carefully and could here the dull sound of a tutor talking and decided to remove the wood from the hole. Bill stood on a brick and was able to press his eye to the hole and see the room above him. At first all Bill could see was the celing and a small piece of blackboard was visible then suddenly his vision was filled with the sight of the science tutor stepping close to the hole. Her shoes were visible and he could see all the way up her skirt. At last Bill had the view he’d always wanted and he became quite aroused. The tutor started writing on the board and Bill felt like an insect under her. Eventually the temptation was too much and Bill slowly slipped his left little finger through the hole and left it in place. He was still able to see past this and watched the tutor writing, her foot only inches away from his little finger. Bills heart was beating faster now in anticipation of the inevitable, the tutor stepped back and he held his breath. He could feel the carpet compress but her foot had landed just next to his finger without actually stepping on it. Bill could see his finger and her shoe almost making contact and his excitement grew. Eventually she walked away and he lost sight of her for a moment, he could hear her talking then he heard footsteps then his finger was crushed. He had not been expecting this and he tensed, through the hole he could see the back of the teachers shoe and her heel planted firmly on his poor finger. Her shoes were dressy with a heel ending in about a 2 inch diameter heel and all of her weight was now channeled through this heel onto his poor finger. Despite the intense pain, Bill knew he couldn’t utter a sound or he’d be caught so he gritted his teeth and endured. The fact that the tutor was totally unaware of the pain she was causing probably intensified the pain as she didn’t think twice about applying all of her weight - why should she it was only the floor. For nearly a minute she stood on Bill’s finger before twisting on her heel and moving off. Bill heard her say something about nearly dinner time and replaced the wood and moved off to the dining room.
Bill loved this college, although the girls did not wear any kind of uniform they were expected to dress smartly as young ladies and this meant nearly all wore some form of heels. The nail Bill had placed in the dining room was next to the serving area and he knew all the girls would pass by when they queued for their meal. He’d set it just back from the till to catch all the slow moving traffic for a great view. Bill wasn’t too concerned about the view however as he’d been far to aroused by the crush he’d just experienced. He removed the wood plug, inserted the same finger and waited. Eventually he heard the bell and this was soon followed by the sound of the girls entering the dining room. After a short time Bill saw the first girl step into view, again he was the helpless insect lying invisible on the floor in front of uncaring feet. The girl passed over him without hitting his finger and the next came into view. Bill knew there were over 700 students at the college so figured even if only a quarter stepped on his finger he would have to endure about 200 girls stepping on his finger. The second girl stepped on his finger with her hard sole. The pain was brief and she’d gone. The fifth girl stepped on him with the same result. By the time the sixth girl towered above him a queue had formed at the till. She towered above him, feet either side of his finger. She was an attractive brunette wearing the customary heels that ended in a 1inch diamater tip. She eventually moved on and the line advanced. A pretty blonde girl was now standing on his finger with the sole of her right shoe, painful but bearable, again the line moved. The next four missed him narrowly then a plump girl found his finger with her heel. The heel was narrower than the tutors and she was clearly heavier. The pain was intense and Bill had to bite his free hand. She stood their uncaring and oblivious to his pain then moved on totally unaware of the suffering she had just caused. Another heel found the mark. A tall girl now pinned him mercilessly to the floor. This girl kept rocking back on her heels and Bill was in agony. This continued for over 25 minutes and Bill estimated well over half had stood on him in the queue. He replaced the wood and looked at his finger, his nail was already turning black and his finger was totally flattened and sore as hell. Bill hadn’t realised the intensity of the crush he’d receive but was totally turned on now.
He returned to his apartment and closed the door behind him and proceeded to do his rounds. He had a spring in his step and smiled to himself as the girls said hello, not realising they’d probably been putting him through hell an hour earlier.
After college finished Bill decided to get a bit more adventurous and returned to the space with his drill and more wood. He returned to the science room hole and enlarged it and then fetched a trolley to lie on. He placed it under the hole and squeezed on to it. With a bit of effort he was able to insert his tool through the hole and lie it between the floor and the carpet. He then drilled a small hole next to his eye so he could see what was going on and tested it. He could get a better view from this angle and could see most of the room in front of him. Bill replaced the wood cover and returned to his apartment, he went straight to bed hoping tomorrow would come faster.
Bill woke at about 6am. He’d been dreaming and fantasizing about the coming day and had woken up with a large swelling to prove it. This made Bill think however, he hadn’t thought about the likelyhood of getting aroused and making the “lump” in the carpet bigger and more noticeable. Bill cursed quietly to himself and started thinking. He remembered reading somewhere that if the blood supply was restricted then it was possible to maintain an erection for longer, this must mean the opposite was true. Once his morning arousal had diminished Bill tied a shoe lace around his cock and tightened it, he checked his watch and noticed it was almost 7am. Time to test his theory he thought. Bill entered the dead space and approached his enlarged hole. He arranged everything as it was the night before and inserted his dick into the hole and ensured it was straight between the floor and carpet. Bill looked through the hole and waited. About 15 minutes later he saw the door open and the cleaner enter with her vaccum cleaner. She was quite attractive but carried a bit of weight, Carol she was called if he remembered correctly. His dick was throbbing now due to its lack of blood and Bill was experiencing arousal as he watched Carol dotting around the room with her polish. As far as he could tell his dick remained in it’s limp state but hurt a bit now. At one point Carol stood close to his spy hole and he could see she was wearing shoes with chunky heels, what a view. She moved to a socket and plugged in her vaccum, the machine started and Carol started cleaning the carpet. Bill was becoming quite excited now and eventually the moment came when she was actually vaccuming his dick. Bill hadn’t realised how painful it would be and as the machine was pushed and pulled over his dick he had to grit his teeth. Eventually she moved forward and stood on his dick. Bill started panicking a bit now because he could see from his spy hole she was staring at the area his dick was with a puzzled look on her face. Bill realised that she was standing on his dick because she’d seen a lump in the carpet and it was her job to make sure there were none. She increased the pressure and started grinding the lump flat, Bill’s face was now bright red as he held his breath and gritted his teeth, his dick was on fire and felt as though it was paper thin. It was clear the lump remained however and Carol was becoming quite annoyed about it and placed her heel over the offending object and applied all of her weight, how Bill didn’t scream was quite amazing but he managed to remain quiet despite the torture he was enduring. Carol was really pissed by now and appeared intent on fixing her carpet, as a result she raised her foot and stamped down on the carpet. She repeated this move five times until she actually stamped Bills dick back through the hole and became happier. Bill could see Carol continue her work then she eventually left the room without a care in the world. At this point Bill climbed down and returned to his room to survey the damage. His dick was still limp but very purple, he was in absolute agony and felt like vomitting as he untied the shoelace. As the blood rushed back the pain increased and Bill could see small cuts start to leak blood, probably due to the stomping he’d just received.
Bill was having second thoughts now, his dick had been savaged and he didn’t know if he could go through any more today so he went to do his rounds. It was about 8:30 now and a few of the girls were arriving, Bill exchanged pleasantries with a few then noticed the science tutor walking down the corridor. She Was wearing a grey suite with knee length skirt and a pair of black shoes with a reasonably low heel, Bill noticed how stunning she looked and immediately lost his common sense. He made his way back to his room and reached for his shoe lace.
Bills dick still hurt like hell but he managed to tie on the shoe lace, he proceeded to his hole in the floor and positioned himself as before. It took a while longer this time however due to the pain and he’d just got positioned when the door opened and the tutor entered. She walked to the desk just by his spy hole and sat down. From where Bill was positioned he could just say see under her desk and what a view it was. He had to strain his neck a bit as his spy hole was at the end of the desk but it was worth it. Bill could see why she’d nailed his finger so well yesterday as he estimated his dick to be about half a meter from the blackboard and about dead center of it. If any teaching involved using the blackboard he was for it.
After five minutes he heard a bell and the girls filed into the room. The tutor went through the usual roll call then settled down for teaching. She stood in front of the class and Bill braced himself, she paced around for a while saying something about properties of elements and then stepped on his dick. The pain was intense but short lived as she stepped straight off again but the sight of her looking totally uncaring and unrealising of what she was doing really turned Bill on. This happened twice more before she sat on the edge of her desk and asked one of the girls to play the video she had prepared. This lesson was obviously a video lecture and Bill felt a little cheated of his fun, the fact that only a few centimeters above his head the lecturer was dangling her feet made up for this however and Bill settled down to enjoy the view.
After a while the video finished and the tutor resumed her talk, shortly into this however the lecture room door opened and the principle walked into the room. She was a lady in her mid forties, reasonably attractive wearing a black business suite and the scariest pair of stilettos Bill had ever seen. She made her apologies and started to address the class. Bill was well turned on at this point as she was stood dead center of the blackboard with her feet planted either side of his dick. She spoke about a forthcoming event and stated she needed the names and addresses of any students interested who were to add their names to the sheet of paper she would now pin on the board. As she moved to pin the paper on the board she shifted position, turned round and planted her right foot squarely on Bills dick and left it there. Bill was in agony and this intensified as she raised herself up on her toes to pin the top of the paper to the board. Once pinned she turned to face the class and placed her left heel on his dick and settled into her shoes putting all of her weight down. As Bills dick was wedged between the carpet and the floor there was no movement or chance of escape and he felt as though her heel was going right through his dick and pinning him to the floor boards. She spoke for about two minutes without moving then asked the girls to add their names and stepped off. The relief was instant but Bill was still in agony. The principal stood next to his spy hole now and looked like a giantess as she stood there arms folded. Bill was so taken with the view that he didn’t notice the girls edging their way toward the blackboard to add their names until the first girl found his dick with her right foot. Again pain shot through Bills dick as this black haired tormentor now flattened his dick. Bill noticed that all of the girls were now forming a queue behind her all waiting to add their names to the list. Bill strained his neck and noticed they were all wearing heels of some sort. The first girl moved off and a small brunette placed her heel on Bills dick and added her name. It was getting intense for Bill and his teeth were gritted and tears streamed down his face. Another brunette added her footprint to Bills tortured dick as she wrote her name then casually stepped off making room for a plump blonde girl to flatten his dick with her sole as she wrote her name, this time the girl twisted her foot as she moved away and a tall redhead placed her spike heel on the head of his dick and commenced writing then stepped off. Each girl was taking about thirty seconds to write their names and addresses and every one of the class stood on Bills dick as they wrote. He was in absolute agony as the queue went down to four and this was about to double. With only three girls remaining, the blonde teenager currently flattening his dick spun on her sole as she stepped off and the unthinkable happened, Bills shoe lace loosened and despite the pain his dick started to harden. The next girl was a brown haired girl with reasonably high but chunky heels on and it was one of these heels that landed squarely on the head of his dick. The pain was double what he’d experienced before and she rocked back on her heels and spun round when she finished. Another brown haired girl stepped up onto his dick with her sole and started writing, she must have been able to feel his dick because she started subconsciously playing with the lump with her shoe as she wrote. Bill could feel himself building up to a climax and had to really concentrate so as not to ejaculate and be detected.
The bell rang and the students filed in. The tutor greeted them and commenced with the lecture. Bills world turned black for a few seconds as she stepped right on his spy hole then she was gone. He could see her approach the blackboard and start writing out the lesson contents. As she wrote he could see her edging closer to his dick until eventually she placed the sole of her right shoe on it. As she applied her weight Bill could feel his dick becoming flatter and flatter until she had completed the move and was standing full weight. The crush was severe and Bill had to hold his breath to stop from crying out. She started prodding the “lump” with her foot and Bill heard her saying to the class “ The principal wasn’t joking when she said to expect a few uneven areas in the floor was she - still I guess we’ll all have to get used to it”. With this she lifted her left foot to move again and for a short time Bill experienced her full weight on his dick, he was pleased it was only a short time however as the pain was absolutely incredible.
At one point during the lesson Bill counted twenty seven times the tutor had stepped on his dick but had never nailed him with her heel, that was until now. Bill could see her talking to the students with her feet about six inches from his dick. She was shuffling and moving almost constantly and narrowly missed him a few times until she took a small step back and planted the heel of her left shoe right onto the tip of Bills dick. As she stepped back he could see her knees lock and Bill knew she was now full weight. The combination of the fact she was only stood on the very tip of his dick and the fact she was used to the footing now and did not consider it anything to worry about caused Bill to endure the most seering pain he had ever experienced. He was crying silently to himself thinking he would be unable to bear anymore pain when it doubled as she started raising herself up and down on her heels as she listened to a student answering a question she’d asked.This went on for about forty seconds and Bill was just on the point of screaming when she stepped to one side and allowed the student the opportunity of working out her question on the blackboard. No sooner had the pressure eased when a raven haired eighteen year old planted the heel of her black ankle boots onto his dick. The boot heel came to a half inch tip which in turn rested squarely on the shaft of his dick and again Bill found himself almost impailed to the floor under the heel of an uncaring woman. She was a bit stumped with the question and stood looking at the board for about a minute trying to figure out how she was to answer the question and during this time her left leg was crossed over her right so that she was standing with all of her weight going through her right foot, the heel of which was doing it’s best to find a solid base about a couple of milimeters directly under Bills dick. Bill had never experienced such a sustained and brutal crush under the unknowing foot of a woman before and the tears were streaming down his face. His hand was bleeding due to the fact he was biting it so hard but despite this Bill was so turned on as all he could see was the face of an angel staring at a blackboard with a puzzled look in her eye.
Eventually she shifted position and the lesson returned to it’s usual routine. The tutor stood on his dick another fourteen times before the bell went then Bill was alone. Bill removed his dick and forced some of the tubing under the carpet just to make sure the tutor always felt a “lump” under the carpet and became used to walking on it. Bill made his way back to his room and untied the shoelace, his dick was the wierdest shade of purple and the tip was heavily bruised. Bill was also amazed to see the shape of a heel print showing as a bruise in the centre of his shaft and felt a little sick.
Bill still had a job to do however and went about his daily duties till dinner time, this found him in the dining room working on a piece of equipment on the floor next to the servery. As the girls queued for dinner Bill could see them walking on the area of rubber tubing he’d hidden and noticed no one seemed too bothered. One of the students said to Bill “how long do we have to put up with this for?” and Bill replied “ there,s nothing I can do about it I’m afraid” “oh well” she replied “I guess we’ll just have to get used to it”. Bill smiled to himself at the prospect - he had big plans for this room.
With fifteen minutes of the dinner break remaining, Bill made his way to the history room via the underneath of the school and again arranged his platform. This time Bill was going without the shoelace and his heart was racing. He squeezed his already aching dick into the hole and watched through the spy hole and waited. Bills dick was hard at the prospect and when the students filed into the lesson his dick was throbbing. Bill watched all the feet pass the desk until a pair of court shoes stopped and the student sat at the desk. From his vantage point Bill could not see the students face but her legs were encased in nylon and beautifully formed. She crossed her legs left over right and instantly found Bills dick with her hard sole. The pain wasn’t too bad and the student was starting to explore the “lump” under her foot. This exploration went on for about five minutes when Bill heard the tutors raised voice. “ Miss Jenkins, is there any reason as to why you’re fidgetting in my lesson instead of paying attention?” “I’m sorry Mrs Davis” came the reply from above the desk “ there’s something under the carpet though” “You obviously don’t listen to the principal either then do you? You were told that Bill had to seal some holes with rubber and you’ll just have to get used to it.” Bill smiled to himself at the thought of the indignant look he could imagine on the students face.
At this point the student started using his dick as a see-saw for her foot and kept rocking her sole over his dick for twenty minutes. Bill is only human and after only two minutes of this managed to ejaculate. If only she knew she was innocently giving the caretaker a footjob whilst doing her work she’d faint on the spot. Eventually she changed position and swapped legs. This time her heel found the mark and Bills pain increased. This girl was one who liked to raise her feet when her legs were crossed and each time she did her heel slid forward slightly and slid back when she placed her sole back on the ground. She seemed to do this non stop and then started lifting her foot and doing fast tapping motions while her sole was raised and this was prolonged for about a minute each time her sole was raised. On top of this she kept sliding her foot in and out of the shoe in the air and this caused Bill to ejaculate another three times before the bell rang and she disappeared from sight.
Bill decided he’d just spent the best hour of his life under that desk and went back to his room, remembering to add some rubber tubing to the underside of the carpet as he had a feeling he’d be back to this spot a few times and logged Wednesday afternoon in his mind as she’d be back in the same seat next week.
As Bill was walking toward his tool shed to retriev the lawn mower for the rest of the days work a young blonde student approached him. She was gorgeous, wearing an all grey skirt with a white blouse and grey jacket and familiar looking black court shoes. “Hey Bill” she called “Do you realise I’ve just bought a mouth full from Mrs Davis because of your stupid floor” Bill replied “I can only do my best love” “Well its irritating, you can’t help but to fidget with it and it gets you into trouble” “ I’m sorry” said Bill, and before he knew what he was saying he’d said “why don’t you wear sharper heels and try and see if you can grind it flat next time your in the room.” “Good idea” she replied “I’m back there first thing Friday morning and I think I’ll give it a try”. As she walked away Bill thought he’d make an effort to be there on Friday as well only about half an inch below her feet.
That night Bill lifted the carpet in the dining room and drilled an even larger hole by the serving hatch that replaced the original and returned to his room before the most daring plan he’d had yet became a reality.
The next morning, Bill got up early and accessed the space under the floor again. He headed for the dining room and took his trolley with him. Bill knew he’d have to set up early as he’d have no time during the day so he worked frantically. He removed the covering wood and lay down on the trolley, once comfortable he added a car jack under his head with a pillow and started to raise it. In less than ten seconds Bill had his face firmly fixed in the hole in front of the serving area. Once Bill knew it could be done quickly he lowered his head and replaced the wood cover then returned to his room.
Bill worked as normal throughout the morning but couldn’t stop his heart from beating quickly. He arrived at the Principals office at 11:30 and informed her he was going to buy supplies and wouldn’t be around for the rest of the day. After this he returned to the space under the floor and took up his position under the dining room. Bill was wearing safety glasses with a dark lens and once in position could just see what was going on above him but hoped no one could see him.
As he lay there he remembered the crush he had sustained to his finger when he’d placed it in the way of the girls at dinner times and began to wonder if this was a good idea. Once they were in he would have to stay put and couldn’t retract his face like he could his finger or dick as the hole was too large.
As he lay there the doubts increased and Bill finally made up his mind to forget the whole thing. As he reached for the car jack the bell went and Bill realised it was too late to back out of it now. He was committed and there was nothing he could do about it.
After a few seconds Bill could hear the first girls talking and laughing as they filled their trays with food. The first came into view and walked towards the till. She was tall and dark haired and as she strode forward toward the till she stepped on Bills mouth with the hard sole of her right foot. The pressure was only momentary but the pain was intense. No one had stood on his face before and he was quite unprepared for the force of the crush. Bill had barely cleared his head when a sharp heel crashed into his forehead then went as suddenly as it hit. Bill was sure his lip was split as he could taste blood and he was really getting panicky at this point. The pain Bill had endured from two girls was enough and he was fully aware he had about another 700 to pass above him and the majority of these would be slower and even stationary as the inevitable queue formed at the till. Another girl passed overhead and the sole of her shoe pressed down on his right cheek as she stepped on his face. Due to the pain his eyes were watering and this combined with his dark lenses made it virtually impossible to distinguish anything other than shapes above him. Another foot found Bills face, this time a heavy sole flattened his nose as the unknowing assailant used Bills face as the floor. The tears increased but his nose held fast. The noise above him was increasing as more girls arrived. Another girl casually stepped onto his face, this time her chunky heel found his eye. The glasses held fast but dug into his eye sockets giving Bill the feeling his eye was being squeezed from his head. No sooner had this pain subsided then a sharper heel found his cheek and this in turn was replaced a few seconds later by a softer sole stepping onto his mouth. Bill was actually getting a bit nervous now, up until this point he had been in control of situations and could escape if it became too much but now he had lost the element of control. Another young lady stepped onto his face and planted her heel unknowingly in the centre of Bills forehead and there it stopped. Bill was in the most pain he had ever experienced in his life, here he was flat on his back while some woman was casually standing on his face with her heel digging into his skull. The heel itself was about two inches wide and Bill was thanking god it wasn’t a stiletto but despite this the pain was so intense he actually wet himself. The queue moved forward and Bill got a small break as a girl towered above him with feet planted either side of his face. His vision was blurred still and he could barely make out the shadowy figure towering above him as she moved on and Bill found his vision obscured by the foot that had just planted itself squarely over his eyes. This girl was heavier and Bill now had a chunky but hard heel planted on his mouth while her sole covered his nose and eyes. Bills nose flattened but held but to his horror he could feel his two front teeth slowly being pushed into his mouth. Bill had reached his pain threshold already and he groaned slightly as his pain entered a whole new level as his teeth slowly began to creak as they were forced to bend under the weight. Just as Bill was sure they would break she stepped forward and Bills face returned to it’s original shape.
The next girl stepped forward and her chunky heel found his nose. This time Bill felt a sickening crunch as his nose finally gave way to the pressure and broke causing him yet more pain. The young lady now crushing his nose just stood and waited with no idea of the exquisite agony she was causing Bill each time she rocked back on her heels.
For over forty minutes the entire college walked on, stepped on and generally abused Bills face. He was not aware of all of it as he’d blacked out after about the three hundredth girl stood on his face and didn’t regain consciousness till about 3pm. Bill had never had a headache this bad before and he slowly and painfully extracted himself from the floor and promised himself never to do that again..
On returning to his room Bill looked in the mirror and was horrified to see his face bruised, bleeding and swollen so badly he could no longer make out his features.
He’d have to be more careful in future and Bill was pleased it was nearly the end of the week. He’d take it easier tomorrow, besides it was Friday and he had a date with destiny under the desk of a pretty blonde student intent on crushing his dick.
Bill phoned the principal at home later that evening and told her he’d been beaten up pretty badly and was unable to work for a couple of weeks. She told Bill to take as long as it took and he smiled to himself despite the pain knowing he was now as well as invisible for the next couple of weeks
Friday morning saw Bill wake up with the worst headache he’d ever experienced, he checked the mirror again and couldn’t believe the difference a night made. He looked worse now, his entire face a mask of bruising and congealed blood. He felt weak but there was no way he was missing today for anything. He remembered the pretty blond student who had commented on the “lump” under her desk and his suggestion for ridding herself of it. Bill cheered up and headed below the boards again. It was only 8am but Bill was going to be sure he had the best view in the house.
Bill found the hole under the desk in the History room and inserted his already hard dick into position, his anticipation of the return bought with miss Jenkins made him harder than ever. From his vantage point Bill could see everything quite clearly and slipped into a dream world until the morning bell startled him back to life. After a few seconds Bill heard the door open and watched the procession of shoes stride in. Eventually Bill noticed a wickedly high pair of black platform boots with a very narrow heel indeed stride into the room, they stopped at his desk and the chair scraped back. Miss Jenkins had arrived.
As she prepared to sit Bill couldn’t help noticing how these calf boots clung to her legs, they were the shapliest he’d ever seen. Her legs were fully visible to Bill as she was wearing a very short black skirt. Miss Jenkins sat down and crossed her legs and Bill could just make out her panty line, if it was at all possible, Bills dick got harder. Her right foot was planted only inches from his dick but this didn’t last long as miss Jenkins started to slowly move her foot towards his throbbing dick. Eventually she made contact with the source of her previous annoyance and raised her foot onto her heel and slowly rotated her foot then lowered it onto Bills dick.
She had applied quite a bit of pressure and Bill felt his dick flatten, it was as well she was wearing platforms as Bill was convinced if she hadn’t been she’d have felt the blood surging through his dick. Slowly and deliberately she now arched her foot so that her heel raised from the ground and she slowly started to grind her foot into the “lump”. Miss Jenkins seemed to be deliberately taking her time so as not to incur the wrath of her tutor again. Each time her foot twisted brought Bill closer and closer to an orgasm, he could feel himself ready to let loose but nothing was happening. Bill realised that the pressure his dick was under was the reason he couldn’t shoot his load and after a few more minutes of this torture it began to get painful but still he was allowed no relief. Eventually she moved her foot and Bill started to orgasm, no sooner had the first drop of come reached the opening of his dick Bill felt the tip of her heel make contact with the base of his dick. The pressure was incredible and Bill found himself unable to come again and even though his balls were screaming out for release the pressure of miss Jenkins’ heel made it impossible. To add to his frustration Bills cock now exploded in pain as miss Jenkins raised her foot up so that only her heel was on the “ground”, again the grinding motion continued at the same slow pace and Bill found himself biting into the floor joist near his head. Bill now discovered that as long as she had her foot on his dick he could not retract it, he was pinned down at the mercy of this teenage goddess for the next hour or so. The grinding continued and Bill was held at the point of orgasm in intense agony as he watched those pretty legs at work. She must have been applying all the pressure she could because Bill could see the muscles in her legs really bulging. Bill began to panic now as he could feel the skin of his cock tearing now, he tried to insert his finger in the hole as well to relieve some of the pressure but couldn’t, he did notice blood on his finger when he removed it though. Eventually the heel lifted and Bill felt weak as a stream of come left his dick only to be stopped as her heel now positioned itself an inch further up his dick. Bill was in absolute agony and the tears now streamed from his eyes, he was already in a weakened state following yesterdays trauma and he was close to screaming as the grinding continued. As far as miss Jenkins was aware there was a piece of rubberised solution under the carpet that was annoying her and she was determined to flatten it, anyway that’s what the caretaker told her to do so she couldn’t be doing any harm now could she!
To add to the grinding motion, Miss Jenkins was also rocking her foot from side to side. Bill began to tremble with the pain and tears were now flooding down the sides of his tortured face making his wounds sting. Despite the pain however the motion of Miss Jenkins’ foot ensured he was still on the brink of orgasm with no sign of release causing frustration to mask the pain slightly. As her heel lifted again he began to come stronger than ever but almost immediately her heel found a point still further up the shaft of his dick cutting off his relief and increasing his frustration. The grinding commenced again and Bill found yet another part of his dick screaming out in absolute agony as her uncaring heel tried to crush it into the floorboards. He found himself gazing up at those perfect but lethal legs wanting to scream out “just finish it bitch” as his balls started to throb in protest of being forced to produce so much sperm without any way of releasing it. Bill could sense at this point that his dick must be in a bad way as he felt dampness on his member, lets face it for the last hour of the lecture Miss Jenkins had been mercilessly grinding his dick with her heel without realising her caretakers’ dick was taking the full force of her assault. Bill was in such agony he couldn’t believe he would ever experience pain worse than that he was sensing now. He was wrong.
With only twenty or so minutes of the lecture left, Miss Jenkins raised her heel again and Bill started to come, he felt her heel come down again next to his dick without hitting it and was allowed full release. He came more violently than he thought possible and became really drained. He decided to try and save himself more torture and attempted to extract his dick from the hole. Miss Jenkins was having none of it however, she could tell she’d missed her intended target and repositioned her heel over that annoying “lump” in the carpet. As her heel came down and her foot raised to increase the pressure Bills head exploded in absolute soul destroying agony. He hadn’t been quick enough in extracting his mangled dick and her heel had come crushing down on the most sensitive area of a mans dick. The head of Bills dick was now been mercilessly crushed under this stunning blondes heel tip and Bill could see she was really putting all of her strength into it, her leg muscles were straining and he could see veins starting to swell as they transported the extra blood needed for the effort. He couldn’t help himself and he started writhing under the boards, it made no difference to Miss Jenkins however who remained unaware of the suffering she was causing underneath her spiked heels as she continued her slow annihilation of the annoyance. After about ten more minutes of this agony she appeared to tire and her foot lifted and moved back over Bills dick until the sole was again flattening his tortured dick. Bill could tell his dick was in a mess because as Miss Jenkins sole covered his entire dick and it was now limp, the pressure was causing his cuts to bleed quite a bit and Bill could feel the blood trickling over his dick. For the next few minutes or so Miss Jenkins ground away at Bills dick with her platform sole until finally the Bell rang giving Bill blessed relief at last. He could see her uncross her legs then as a kind of parting shot stomped as hard as she could on the “lump” with her heel as she stood up. Even though Bill could see it coming there was nothing he could do but tense himself as his world exploded into a new dimension of pain, the tears streamed down his face and without knowing it he slipped into semi consciouseness with the pain. He started dreaming of this blonde girl giving him a foot job but not actually letting him come when he almost orgasmed and unknown to Bill he got hard all over again then drifted back into consciousness.
Bill decided enough was enough and tried to pull his dick out of the hole and retreat back to his room and sleep it off. To Bill horror he discovered that the wood around the hole was splintered following Miss Jenkins assault and as long as his dick was hard he couldn’t remove it without impaling it on the jagged wood around the hole. Bill concentrated on negative thinking to try and make his dick go limp but every time he got close the image of Miss Jenkins returned to him and he found his dick going harder again. Bill managed to reach a screwdriver in his back pocket and started to work on the wood trapping his dick. He was about half way through the obstruction when the bell went again. Bill froze in terror knowing he’d find it difficult to go through another hour and a half of torture on his dick and worked harder at the wood. He tried to remove his dick but it was still too hard. Out of the corner of his eye Bill saw the room door open and the next class file in. Bill was stuck fast and there was nothing he could do about it.
As he watched the feet pass the desk he waited for the inevitable and sure enough one pair of shoes stopped and made for the desk. If the legs were anything to go by this girl was stunning. She was wearing black stockings and from his vantage point Bill noticed the lacy tops and suspenders and this was set off with a pair of thick soled black strappy shoes with a chunky but high heel. As she sat down she crossed her legs and Bill felt the pressure of her right sole pressing down on the lower half of his dick. Again Bill found himself pinned down and unable to retract even if he was able to.
She moved her chair forward slightly and moved her foot accordingly and now his whole dick was trapped under her sole. The pressure was quite hard but bearable after his last encounter and he could feel himself getting just a little excited.
After a few minutes she angled her foot so that all of the weight was distributed on the right of her foot. The pressure on his dick didn’t change however as it was rolled to the right under her foot and then rolled to the right as she rocked her foot onto it’s left side. It was apparent the class was undergoing an exam of some kind as he could make out the scratching of pens against paper in the silence. The rocking motion became quite rythmic and eventually Bill shot his load but remained hard. The motion continued however and Bill came again a few minutes later and again shortly after this. The cuts were now covered in salty come and hurting quite badly and his unknown assailant continued to rub in the “cream” without realising the results of her innocent actions.
A few minutes later she uncrossed her legs and reached for a pen she’d dropped. Bill caught a glimpse of the raven haired goddess torturing him. Miss Jenkins was damned good looking but his new tormentor would have looked perfect on the front cover of vogue. She sat up again and crossed her legs once more this time pinning the base of his dick with her heel. This hurt a hell of a lot more as she was crushing his dick into the splinters of wood that held it prisoner. She raised her foot up on her heel and his dick was suddenly pierced by the splinters. As she held her foot there he could feel a sharp piece of wood slowly penetrate his skin deeper and deeper. The tears returned to his eyes and he wasn’t sure if he could bear this new form of pain then the pressure eased as she returned the sole to the ground with a thud.
A few seconds later the foot raised again and Bill could feel himself being impaled once more in a slightly different place. Deeper and deeper went the splinter and to add to the torture she started a tapping motion with her foot which distorted the base of his dick and started to tear the flesh where the splinter was entering. After a while she changed legs to Bills relief and again he was pinned by the sole of her right foot and not in as much pain despite the fact his dick was more tender than he had thought possible. She started to raise her foot again but this time instead of searing pain it brought relief as her sole raised from his dick. The major source of pain at this time was when she lowered her foot, as she tended to do so quickly and with a thud causing a considerable amount of pain to Bills tender dick.
Eventually the bell went for dinner and Bill found relief as she stood and left the room.
Not wasting anymore time Bill went carefully back to work with his screwdriver to remove the splinters. His dick was limp now but still he couldn’t remove it. Eventually the splinters were removed (with some difficulty) and Bill breathed a sigh of relief as he started to ease his tortured dick from its hole. To his horror Bill found he couldn’t remove it, he figured it must have swollen due to the punishment of the morning and he found himself panicking. Unknown to Bill at this point was the fact that as the splinters were cutting onto his dick one had actually pierced a vein causing blood to well up in his dick and swell to twice its usual thickness. Bill had to think fast but was panicking too much, he realised there was a small pen-knife attached to his belt and this was to be his only hope of release. He struggled to reach it but managed eventually and started to whittle away at the wood trapping his limp but larger than life dick. He worked feverishly but as the bell signalled the end of dinner he knew he had to go through it all again and started sobbing uncontrollably under the desk until that familiar crushing sensation brought him back to reality as his dick was again flattened by some uncaring college student who knew nothing of the pain she was inflicting. Bills eyes shot open and he spotted the red boots and jeans of his next tormentor.
Bill was in big trouble and he knew it. He was only thankful he was on the sick and no one would come looking for him. The pain in his dick was still quite bad even though there was no actual pressure on it yet as he stared at the feet of this new girl he knew things could only get worse. She was wearing a pair of red boots with a heel of about 4 inches ending in a thin rectangular tip measuring about 3 cm by 0.5cm and the sole was reasonably thick.
Once she was seated she pushed her feet out and crossed her ankles and Bill was staring at the bottom of her feet only inches from his face. He was somewhat relieved she had adopted this position as he was spared further pain for the moment. She kept this position for quite some time but eventually the inevitable happened. She sat more upright and crossed her legs properly and Bill once again found his dick taking the weight of a students sole. She was obviously uncomfortable as she moved her foot about quite a lot before moving it forward slightly to a more comfortable position. The comfort of this tormentor however meant increasing agony for Bill as her heel now rested firmly over the middle of his dick causing Bill to experience yet more torture at the foot of another teenage tormentor totally oblivious of the pain she was causing. For the rest of the lesson she fidgited and kept raising her foot on her heel and Bill was feeling extremely nauseous at this point until the bell went and he was released from his torture but not the pain. Again the bell sounded for a new lesson and Bill was still trapped under the desk but this time no one entered the room, at last Bill got a break as he realised the room was empty for this lesson. He whittled away at the wood with his pathetically small knife trying to widen the hole so he could release his dick and try and get some relief. He was making progress slowly and his hand was aching due to the difficult angle he was working at and the bell signalling end of the day had sounded quite some time ago when the door of the room opened. Bill was surprised to hear the door then spotted a pair of legs and the bottom of the dress of one of the cleaning staff, he’d forgotten that the rooms were cleaned on an evening as well as the morning.
The cleaner started moving desks about and was then joined by a second cleaner who started chatting away to the first, Bill found it quite amusing that the topic of conversation was his apparent mugging the day before. Judging by the tone of the legs he could see, Bill figured they were both on the younger side and the footwear was certainly the more prefered of the younger cleaning staff. They were both wearing hard soled shoes with those chunky heels that were the fashion. Eventually Bill could see everything as the desk he was under was moved and he noticed the faces of the cleaners for the first time. He had been correct in his assumption that they were both young, he’d seen them before and considered them both quite attractive. One was brown haired and the other red and both were of slim build. He always remembered the brown haired girl had the biggest pair of tits he’d ever seen and again he became aroused. This time his arousal brought him pain as his dick was already swollen quite badly in its limp state and again he felt tears emerging from his eyes and run down his cheek.
The red head stood over him and turned to her friend and Bill heard her say “Julie, fetch the trolley some daft cows spilled some red ink on the carpet and it’ll be a bitch to get out”. Bill realised that after a full day of torture to his dick the blood must have penetrated the foam backing of the carpet and stained the carpet red. Combined with his orgasms and the grinding of dirty feet over his dick Bill could only imagine the mess that was left behind now the floor was cleared
Julie pushed over a cleaners trolley and said “there you go Kay” and Kay took from it a bucket containing cleaning agent and a hard scrubbing brush.
Bills eyes widened in fear as he realised what was about to happen. He gritted his teeth and prepared for the inevitable as Kay stood over his vantage point then got down on her knees above his eyes, pulled on a pair of rubber gloves and dipped the brush into the cleaning agent. As soon as the brush touched his dick he was in agony as every nerve screamed for mercy however Kay was unaware of this as she started to scrub the carpet with some vigour. Bills senses exploded as the hard floor brush was pulled and pushed up and down the length of his dick and within seconds he exploded and felt quite dizzy. The sheer pain of the experience was the only thing keeping him conscious as the scrubbing continued relentlessly over his battered and worn dick. Kay stopped and Bill felt some sense of relief but Kay merely wiped some sweat from her forhead, muttered something to Julie about it being a stubborn bastard and went back to work with renewed vigour. A minute or so later a voice was heard saying “Kay your wanted on the phone” and Kay stopped and Bill let out a sigh of relief. “Julie can you finish off here for me” said Kay as she got up and walked to the door treading on his dick on the way and a moment later Julie appeared, pulled on her gloves and Knelt down somewhere in the region of Bills knees and picked up the scrubbing brush.
Julie was fresh and the scrubbing started with some force, Bill could see those tits up close know and found himself able to look down the top of her dress at the bare flesh and orgasmed again only this time it brought only a wave of sheer agony as the merciless scrubbing continued. This went on for what seemed an age and Bill came twice more and was totally spent when she eventually stopped and said “fuck this”. She stomped on the carpet with some force muttering profanities as she left the room and returned moments later pushing an industrial carpet cleaner that she plugged in and pushed over to the “stain” and promptly switched on.
Bills eyes widened in fear as the noise level increased, he’d repaired this machine a few times and knew how heavy it was - it took quite an effort to actually push it and the girls were always complaining about it. Added to this the fact that it worked on the principal of forcing very hot water and detergent deep into the carpet then sucking it back out Bill was petrified.
Julie slowly pushed the machine into position about an inch from his dick and switched on the water jets then slowly pushed it forward. Bill felt the water starting to scald the base of his dick and drip through the hole onto his nuts, he groaned out loud but the noise was drowned in the sound of the machine. Slowly she covered the entire length of his dick and continued toward his face.One of the wheels found his dick and slowly started to flatten it as it edged it’s way along the shaft of his dick. As it reached the tip Bill felt something give and he vomited and moaned quite loudly, the wheel stopped over the tip of his dick and held position. Bill saw Julie switch off the water and saw her foot move to the button situated above the wheel that was over his dick and watched her press it down. The added pressure made Bill feel hid dick crunch and then the wheel moved down his dick again as the suction started. Julie dragged the machine down his dick then back up again and when his dick was clear she stopped it and walked over to the socket and unplugged it. She walked back to the machine and started to wind up the cable but in doing so placed the heel of her right shoe over the tip of his dick and applied her full weight as she reeled in the cable. Bill passed out at this point as the pain became unbearable and awoke some time later and was surprised to find his dick had worked free of the hole. He replaced the wooden boarding and rubber and felt his way back to his room, looked at the state of his mangled dick, cryed then blacked out again with the pain.
When Bill finally awoke it was in the early hours of the morning and his dick was hurting like hell. He went to the toilet and almost passed out again when all he could do was piss blood. His dick was just a swollen purple lump with no shape and a nasty gash right at the tip. (as the wheel travelled up his dick it had forced all of the congealed blood to the tip and the pressure had actually burst the skin releasing all of the blood - this is how his dick was free when he woke the first time.)
Bill decided he needed to rest for a while and would spend the summer holidays working out new ways to feed his fetish. He would stay above the floor for a while as this last encounter with teenage goddesses had left him in no fit state to endure even the slightest pressure for quite some time. He had plans though and figured the annual meeting of the union of women teachers held at the college for a full week during the holidays would be the time to try some new ideas he had.
Comments
Luis R Morales
Yeah I have that one. I’ll look for that one.
Austin Snegdle
Please do! There was some great unknown trample ones on there. There was one about being a scarecrow dummy for the neighbors, and they used him for photo ops, but I can't ever seem to find that one again.
Luis R Morales
I got tons of stories from MIstress Destiny and other past fourms that got taken down. Will post them time by time. Enjoy
