Jenny's Fantasy
by Mike
Jenny lives out her long-held fantasy of a bare bottomed caning
Ever since she saw a boy return to class after being caned, Jenny had had this fantasy of what it would be like. But could she really cope with the reality?
Jenny had now been left school for three years. A month ago she had celebrated her nineteenth birthday. She was a petite girl, only five foot four inches without shoes, but very pretty. Her hair was natural blonde and cropped at the neck. Her skin was evenly pink and smooth.
Standing in front of the mirror, completely naked, she admired her nicely pert, ample breasts, her nipples standing to attention in a state of arousal at what lay ahead that morning. Her eyes drifted down her body past her slender waist and to the vertical crease of her pusssy, completely bold and visible. Jenny liked to shave. She felt so much more feminine with a smooth pussy. And it was a cute little pussy. Her lips were quite visible, but not over large, and they glistened slightly, the moisture giving away her aroused state.
She leaned over and picked up the bra and pantie set she had bought especially for the occasion, and gently put them on. The material was a prostitute red and so thin as to be almost transparent. The bra cups formed nicely around her boobs, her nipples pushing out the material as if it wasn`t there. Her panties fitted tightly over her perfectly formed bottom, the center crease very visible through the material, which also formed itself into the shape of her pussy lips – slightly darkening over that small area from her dampness.
Jenny stood again in front of the mirror, looking at a body that still appeared quite naked through her underwear. She trembled slightly at the thought of the eyes that would soon be enjoying this sight. She continued to get dressed, putting on a beautifully pure white long sleeve blouse and a red skirt that came barely four inches below her crouch. The skirt was light and flicked around her legs as she moved, and had a pretty two inch wide red leather belt with matching red buckle. She finished off her outfit with a pair of white ankle socks and red high heel shoes that lifted her an extra two inches, making her legs look longer and pushing her boobs into her blouse.
She sat down and waited. Toni and Anna were to collect her at 9am this Saturday morning, barely a quarter of an hour away. Her thoughts drifted back to how this all began and fear started to creep back, as it had done many times over the last few weeks.
Jenny had a fantasy that had begun about five years previously. One day, at school, she was sitting in class when one of the boys had come in late. His face was bright red and it was obvious that he had been crying. He had just come from the headmasters study after being caned. She watched as he gingerly sat at his desk, shifting from side to side in an attempt to lessen the pain he was obviously in. Jenny began to wonder what this would be like. There was no chance of it happening to her, she was a good pupil. And the thought of it actually happening filled her with dread. But what would it be like?
This thought never went away and slowly the fantasy began to evolve. She would pleasure herself thinking about being summoned to the headmaster, being made to bend over the chair in the center of his study, and then humiliatingly caned. As with all fantasy`s, this began to get more and more exciting. Eventually, she imagined she was in front of the class. She was being made to strip naked and bend over the teachers desk, displaying her bare ass and pussy for all to see, totally humiliated, before receiving six strokes of the cane across her naked skin. The more humiliated she was, the better the fantasy. She could get very wet just thinking about it.
This would have been fine if she`d kept it to herself. But during a boozy, girly night in at Anna’s flat she had confided to her two friends. Toni and Anna could not believe what they were hearing and thought it hilarious. But later, when they were together alone, they decided that it might be fun to try and set something up.
Toni knew a friend, Steve, who owned his own small business at a place out of town and she thought this could be ideal. She knew a caning would probably be noisy, and a factory floor would be a good place not to attract attention from anyone outside. Also, this place was in an area where Jenny would not be recognised. She paid Steve a visit and outlined her plans. Steve looked aghast at first but the idea did appeal, especially that he could use his own staff as an audience. He agreed that he could possibly set something up for a Saturday morning, when the industrial area would be relatively quite, but Jenny must be completely sure of this and she should contact him personally to agree. He would discuss it with his own staff and let her know.
A few weeks later Toni got the call she wanted. Steve could set this up. He had approached some of his closest staff and they were all keen. There would be six males and two females, plus Steve himself.
Toni and Anna now had to convince Jenny. Would she be willing to actually fulfil her fantasy?
“What the hell are you talking about” Jenny raged as Anna spluttered out what had been arranged. “You want me to stand there naked in front of a group of leering strangers, and get my arse caned into the bargain.” “But that is your fantasy” said Anna. “You have dreamed about this for years. It will be just one morning in your life and you will have the memory of what it is really like to be humiliated and caned to put into your fantasy for years to come.” There was no convincing Jenny. She couldn`t believe that her two best friends would even discuss this with other people, let alone try and set it up. Anna decided to leave the matter there, saying only that maybe she should think about it over the next few days.
That night Jenny sat alone in her flat. The TV was on but she wasn`t watching, her mind was swimming with what she had heard earlier. She was fuming inside that she had been betrayed by her friends over something that was said through too much booze, and should have been private. As she sat there her mind began to drift back to her fantasy world. She imagined herself, as always, being summoned to the front of her class. But when she got there and turned around, the scene was different. She found herself staring at strange faces, adult faces. Her hand went between her legs as she imagined herself being made to strip and stand there, with the total humiliation of all these strange eyes burning into her naked body. She began working at her clit as her imagination had her bent over the desk; legs spread enough to give all these prying eyes an unobstructed view of her cute pussy and even a sneaky hint of her most intimate bum hole directly above. As her caning began, her fingers worked feverously at her pussy until she exploded into orgasm.
As she sat there completely drained, her thoughts went to her changed fantasy. Strangers staring at her had made the humiliation greater and her orgasm was stronger than usual. Would it work to make this real? The thought actually appealed for the first time, but could she physically stand naked in front of a group of strangers? Then there was the caning. This is where her fantasy had started, and it had to be part of it, but could she go through with it? Could she bend over and allow a man to physically cane her naked arse, and in front of an audience at that? Why was she even thinking like this? She didn`t know, but the thoughts were certainly turning her on again and after a few minutes of frantic fingering, she orgasmed again.
Next day, Jenny tried her best to stay busy and put all thoughts of naked displays out of her mind, but it didn`t really work. It was not a good idea, walking around the supermarket in a daze, trying to rub her legs together to avoid the urge to masturbate right there in the aisle.
What the hell. It could be quite exciting to strip in front of a bunch of strangers, flaunting her tits and pussy for all to see. She had a pretty body, nothing to be ashamed of. Most men would not turn down the chance to see her; they would probably want to masturbate at the thought. So they were to see her with her naked arse in the air, being caned. So what, maybe it would give some of them a new fantasy. They would never see her again. She would finally have the experience of being caned; she would never get this chance again. Is it a chance too good to miss? What the hell was she thinking? She couldn`t believe that she was even entertaining the idea, but the pull was getting stronger. She had wondered for years just what a good caning would be like, and the humiliation of being watched had given her many a good orgasm.
This has got to happen she thought. So she`d have a sore arse for a few days, she`d have a memory for life. Then and there she rang Toni on her mobile and told her to get on and organise it before she changed her mind. Toni couldn`t believe what she was hearing. Here was her best friend asking her to be set up to be totally exposed in all her naked glory for all to see, and to take six of the cane across her bare backside . She was going to make sure her friend got the humiliation and hiding of her life and she was going to be there, with Anna, to see it. She now had one major surprise to organise, and she wasn`t sure if she could pull it off.
Suddenly Jenny was shocked out of her thoughts by a knock at the door. She glanced at the clock. 9am. Oh my god this is it she thought as she went to open the door. She pulled Toni and Anna inside quickly so her neighbours didn`t catch a glimpse of the way she was dressed. “My God!” exclaimed Anna, “You look like you`re ready for a night on the street”. “Anyway, no time to lose. We have to get you to your punishment on time. Everyone will be waiting.”
Jenny didn`t really want to go outside dressed as she was and she wanted the girls out first to make sure the coast was clear. Toni and Anna went to the car, looked around and beckoned Jenny out. She locked her door, ran up the path out onto the street and straight into a bunch of teenage lads. “Wow,
Show us your tits luv” one of them leered as she fell into the back of the car and yanked the door shut. “Drive you bastard” she yelled at Toni, who was in fits of laughter.
Jenny had no idea where she was being taken, She had met Steve once at Toni`s house to explain what she was thinking and to let him know that she was serious (that was an embarrassment in itself) but she had no idea where his factory was, or indeed what he did. Toni drove out of the city and onto an estate that Jenny had never seen before. The trip took around forty minutes, giving her plenty of time to realise just what she had in store. She knew her friends had planned this to the last detail and she knew they were planning hell. For some reason, for the first time since seeing that boy in her class all those years ago, it finally hit home just what a good caning meant. Why had she never thought of this before? At her school the headmaster caned the boys. His caning was felt to be too severe for the girls so a female teacher was tasked with that. Jenny just knew that the girls had arranged a man to cane her. The boys were also caned whilst dressed. She was going to have to present her naked backside. What was she thinking of agreeing to this.
All too soon they arrived at an industrial estate well off the main road and pulled into a factory car park. “You are to get out now” said Toni. “Walk over to those doors over there. Inside there will be a receptionist. Go up to the desk, give your name and say you have arrived for your punishment. We will see you inside in a little while.
Jenny’s heart was racing as she tried to get out of the car in some sort of decent fashion, her skirt riding up to give a glimpse of her now very wet panties. She walked briskly to the door, not wanting to be seen, and hurried inside. She stopped immediately she was through the door, taken aback by the extremely pretty girl standing behind the desk. She was tall and probably around twenty-five years old, with long auburn hair down over her shoulders.
Gulping loudly, Jenny walked up to the desk. “Yes, can I help you” the girl said matter-of-factly. “Hi, I`m Jenny Harris. I`m here for my punishment”.
The girl picked up the telephone. “Mr Carter, I have a young lady here, a Jenny Harris. She says she is here for her punishment”.
“Mr Carter is expecting you” said the girl. “Please follow me”. As she stepped from behind the desk, Jenny became more aware of just how tall she was. At least five foot ten, and immaculately dressed in a black trouser suit. She followed the girl along a corridor and waited as she knocked at a door. As they entered she first saw Steve sitting behind a large oak desk. This must be his office, she thought. Her eyes then caught another girl standing against the wall. This girl also looked to be in her twenties, again in an immaculate suit and with long blonde hair.
“Ms Harris to see you sir” The tall girl said. “Ah, Ms Harris. Please come in. I understand you have come here this morning for your punishment, so let us begin. I believe you have been having naughty thoughts about being caned. Well young lady, we are all here today to teach you that you should be more careful about what you wish for. I am sure that when you leave us this lunch time you will be more than aware of what a sore bottom feels like. Please remove your blouse and skirt.” Jenny was taken aback by Steve’s last words. Here she was in a strange office with Steve, who she didn`t actually know, and two strange girls, and he was asking her to undress.
She slowly began unbuttoning her blouse. She could feel her legs shaking, and she was definitely getting damp down below. As she peeled off her blouse she could feel the eyes of these two young girls fixed on her boobs, barely hidden under her bra. The skirt was more of an ordeal; she knew what would be visible when this came off. Nervously, she undid her belt and pulled at the zip at her side. The skirt was light and the weight of the belt made it drop to the floor instantly. Jenny now felt very vulnerable, well aware that her knickers must now be very transparent from her wetness. “I think we can also lose the shoes and socks” said Steve. This was now embarrassing. Jenny was only in her bra and panties and she had to bend to remove her shoes, and the girls were now right behind her.
She stood in front of the desk now just in her underwear, watching Steve’s eyes as he looked her up and down. “Very pretty” he said. “Ms Banton, would you be good enough to remove her bra.” The tall girl now stood next to Jenny. Oh my god thought Jenny, this girl is going to strip me, no girl had touched her like this before. The girl slowly pulled the straps of Jenny’s bra off her shoulders. Feeling around the back, she unclasped the hook. The bra didn`t move, sitting snugly on Jenny’s pert boobs, until the girl gave a gentle pull.
Jenny stood there now almost naked, her face as red as her knickers. What was she doing? “Tie her hands now Ms Banton, and the gag if you please” Before Jenny could react her arms were pulled forcibly behind her back, making her boobs wobble as they stood out proud in front of her. She felt her hands being tied with something soft. A ball gag was now pushed into her mouth and tied tight behind her head. This made her retch a little. “Now the show begins” said Steve. “Bring her along ladies.”
Jenny was marched out tied and gagged, her little arse wiggling under her tight panties. Suddenly she felt very scared. They had gone through a door into what was obviously Steve’s factory floor. In front of her was a steel platform about three feet high. On top of this was fastened some contraption that looked like scaffolding, shaped like a table with no top. The two front legs were shorter than the back ones making the table seem to lean towards her. Beyond this platform was what had really caught Jenny’s eyes. Her audience. Sitting there must have been more than half a dozen people. Jenny was forcibly marched round to the front of the platform. There she stood in all her glory, naked apart from a pair of wet panties, hands tied behind her back and a gag in her mouth that was now causing saliva to dribble down her chin.
Steve and the two girls took their places in three empty chairs on the front row. Also on this front row were Toni and Anna, big cheesy grins on their faces. “Now we have the main attraction standing before us” said Steve, “It`s time to meet the man who will cane her pretty little bottom.
Jenny turned her head as a side door opened. Oh my God, NO! Through the door walked John Chambers, Jenny’s old headmaster. How the hell had Toni arranged this. John walked up and shook Steve’s hand, turned and faced Jenny. In his hand was a vicious looking cane, about three feet long and a quarter inch thick. She could feel herself blushing all over. John was a handsome man in his forties with silvering hair and Jenny had once had a silly schoolgirl crush on him. And here he was now, standing two feet away from her naked bound body, and all she could do was dribble. Her eyes focused on the cane. She had never actually seen one before and had not realised just how menacing it looked. Soon, much sooner than she wished, John was going to be using this instrument of torture on the tender stretched skin of her naked bottom.
“I think it`s time for you to lose the knickers” said Steve. “Ms Banton, please do the honours and bring them to me.” Jenny didn`t really pick up on the last few words, horror had overtaken her at the thought of this girl now removing her panties. The girl approached Jenny and knelt at her side, her hands reaching for the edges of Jenny’s knickers at her hips. With a nod from Steve she slowly pulled. The knickers soon came away from her bottom but with Jenny’s legs close together they travelled a fair way down her thighs before eventually pulling away from her groin. Her audience began to applaud as they fell to the ground. The girl lifted Jenny’s calves, one at a time, helping her to stand out of them. Holding them high for all to see she walked back and passed them to Steve before retaking her seat. Steve held them for a while, feeling their smooth and very moist texture. Then, staring Jenny straight in the eyes he slowly brought them to his nose, taking in the aroma of Jenny’s sex. He folded them neatly and put them in his Jacket pocket. “A memento of the occasion” he said.
Jenny stood there mortified. Here she was in front of maybe a dozen people completely starkers. Her hands tied behind her back forcing out her boobs, and her pussy so obviously on view for the world to see. And to cap it all she was now dribbling profusely from her ball gag, her saliva making little streams of glistening water travelling down between her breasts and onto her stomach. She suddenly thought that she had no idea where her clothes were, except for the knickers that were now lost in Steve’s pocket.
John took hold of Jenny’s hand and turned her to face the platform. This was the first glimpse her audience had of her soon to be caned bottom. “Up the steps my dear” John said. The sudden feel of the cold metal steps made Jenny stumble and lean forward to try and regain balance, giving her audience a magnificent view of her pussy which brought a loud cheer. She stood at the top, now visibly shaking, looking at the contraption in front of her. The two girls that Jenny had met only a short while ago had followed her. They moved her close to the frame and released her hands and gag. “I`m sure everyone would want to hear your screams.” the tall girl said.
They manhandled Jenny over the frame. As her waist folded over the bar her feet came off the ground. Her torso was brought down onto the cold steel bars. The girls then proceeded to tie Jenny to the frame. Her hands were tied first, her arms outstretched wide in front of her. Her legs were then pulled taunt and her ankles tied to the frame about shoulder width apart. The girls then tied a cord around each of Jenny thighs, their hands brushing against her intimate parts as they fastened her legs to the frame. Jenny was now very frightened. She was trust up solid against this unforgiving contraption, stretched into a position that had made the skin of her bottom tighten. Her feet were off the ground and spread to give her audience a ring side view of her glistening wet pussy, the lips now peeking out beyond her cheeks.
“Just one more thing before we invite John up on the platform” said one of the girls. “I`m sure you wouldn`t want your audience to not see every part of you and there is still one little part you are hiding.” With this Jenny felt the girls` hands on her bottom, pulling her cheeks apart and stretching out her cute little bum hole. Another cheer. Jenny was now starting to cry. How could they expose her like this? No one, not even her, had had this view before. She would never see these people again, but her two friends she would, and they were now staring at the petite ripples of skin encircling her most intimate entrance. After what seemed like an age, the girl released her grip, running her hand over Jenny’s cheeks before walking away
Jenny felt a hand begin to caress her breast, and was startled by Johns face right up against hers. “I`m very,very good at this”, John whispered. “After the first stroke you`ll be offering me a blow job to stop.” John squeezed tighter on Jenny’s left breast, then disappeared back behind her where she couldn`t see. What was happening? The room was quite and Jenny lay there for what seemed minutes.
Suddenly Jenny’s world changed. John had swung the cane to hit high and straight across the naked, vulnerable skin of her bottom with devastating force. The pain was excruciating. Jenny felt as if her backside had been split in two, her whole body went rigid as she fought to pull away from her bonds. This first stroke had caught her so by surprise that she was to busy drawing breath to utter a sound. Tears welled in her eyes as she fought against this unimaginable pain.
The second stroke hit with equal force and an inch below the first. This time Jenny did scream, her arms and legs pulling to free themselves, but to no avail. Jenny had never in her life felt pain like this; it seemed to consume her whole body. Never could she have imagined it in her fantasy. “Stop” she yelled, “please, no more.”
John walked around and bent down in front of her. “Are you offering me a blow job” he said. “Yes, yes” she cried, “just please stop.” John said nothing and walked back behind her.
Two ugly weal’s had appeared across Jenny’s bottom, one parallel and an inch below the other, showing clearly the accuracy of Johns handwork to his audience who up till now had been quite and transfixed. “Whip the bitch.” All eyes turned to Sue, the tall girl who had just before had Jenny’s arse spread for all to see. Then slowly others began to join in. “Show the bitch what for, make her beg.” The spectators were now really beginning to warm to the occasion, but not anywhere near as warm as Jenny’s bottom was becoming.
The third stroke brought a piecing shriek. Jenny’s whole body shuddered and red marks were starting to appear around her restraints as she struggled feverously to escape the horrendous pain overwhelming her. After the first two stokes, the pain had subsided slightly. But not this time. Her backside was now a complete explosion of pain that was not going away. Again she screamed “Stop, stop this. I can`t take anymore. Please stop now. I`ll do anything, just please stop”.
Her audience was now beckoning John for the next stroke. “Cane the whore.” “Make the bitch squeal.”
John just stood there admiring the three gruesome weals across Jenny’s once pretty bottom. Three perfect lines each one inch below the other. Her whole backside had now turned bright red. Even with the way Jenny had been stretched over the frame, she continued to pull at her restraints, trying to break free from this torture. The slight movements she could make caused her breasts to perform a dance beneath her, which was not lost on her admiring audience.
After what seemed like an age, with Jenny begging for her ordeal to end and her audience baying for more, John positioned himself for the next stroke. Without warning to Jenny the forth stroke was more vicious than the previous three had been, again with superb precision, an inch lower on her naked skin. A devastating pain surged right through Jenny’s poor body, causing her to fit uncontrollably. A thin stream of urine spurted from between her legs, hitting the floor about two feet behind her, much to the delight of her audience who began pointing and laughing. Jenny continued to pee, not able to control her body anymore, her convulsions forcing the thin stream to flick around.
John stood back, admiring this watery display from close range. When it finally stopped, the last dribbles running down the inside of her right thigh, he walked round to where her head was hanging down between her outstretched arms. He knelt next to her and lifted her head by her hair. Her face was a mess, contorted with pain and fear, tears covering her cheeks and running into her mouth. She looked at him with distant bloodshot eyes and whispered “please stop. I beg you to stop. I really will do anything.”
“Suck me” John said softly. With her head still held by her hair, she gently nodded. John stood in front of her. Still holding her head up he undid his flies and took out his dick. John was aware of the audience but the thought of Jenny’s pretty lips around his manhood was too inviting, and anyway Jenny’s body would hide him from view. Masturbating till it was hard in his hand a few inches from Jenny’s face, he moved forward till it was touching her mouth. Jenny, still shaking, her body wrecked with pain, slowly parted her lips, inviting him in. John slowly fed his dick deep into Jenny’s mouth and let her seal her lips around it. He moved back and forth half a dozen times letting her feel his hardness in her mouth, then pulled it out with a jerk, letting her head drop. “Not that easy young lady” he said. “You asked for six of the best, and six of the very best is what you are going to get.”
John knew how to cane, and he still had a couple of tricks to play. The fifth stroke was aimed diagonally across the four very distinct weals. Jenny’s head shot up almost as if it was trying to leave her body – and the pain – behind. She had now lost all sense of anything around her. All she knew was an all consuming pain right to the very core of her being. She no longer had the strength to scream, all that came out was a strange gurgling sound.
Again John walked round and lifted her head sharply by the hair. He looked straight into her wet eyes. “You still have one stroke to count – and girl are you going to know about it.” Jenny’s eyes widened and she tried to shake her head. She wanted to plead but the words just wouldn`t come out.
John had saved his party piece till last. In his days as Headmaster he knew how to make even the toughest of boys squeal, and they were wearing clothes. Jenny’s naked tender bottom just didn`t stand a chance. John positioned himself, stepped forward and landed the cane with an enormous crack on the crease line that divided Jenny’s bottom from the top of her thighs. John knew this to be the most sensitive area and the result was spectacular. If the frame that Jenny was tied to had not been fastened down, surely it would have moved across the floor with the violent jerking of her body. This time she did scream although more air than sound came out. Her breathing was now rapid as she tried to comprehend the pain surging through her. Her rear end was on fire and the heat seemed to spread to every nerve ending in her body. Tears came full flow as she sobbed uncontrollably, pulling at her restraints in total desperation.
The way that Jenny was stretched across the frame meant that the last stroke, aimed across the crease at the top of her thighs, had also caught the center of her pussy. Her lips now began to swell slightly. They were still wet from Jenny’s original moisture and her pee, and now they began to glisten gloriously red in the light.
Jenny had settled a little now, no longer pulling furiously at her restraints. She was still twitching slightly from the pain that was still exploding in her bottom, and sobs could be heard. Her behind was now turning a deep purple between the six ugly weal marks. She felt the bonds on her thighs and ankles being released letting her legs free to dangle. She couldn`t get up, her hands we still tied to the frame, leaving her still outstretched over it.
“We need to do something about those weals” she heard a female voice behind her. Sue knelt next to her and sprayed all her rear end with an antiseptic. Nothing happened for a few moments, and then suddenly Jenny erupted. The spray had penetrated her wounds and the stinging heat was unbearable. Jenny began to thrash about on the frame. Now her legs were released they danced about in all directions, occasionally crossing to try and rub her lips together. Her pussy was obviously very sensitive and didn`t like this spray one bit. Her bottom and all her most intimate area was on fire. She caught hold of the frame with her foot and arched her back, lifting her backside up into the air and then dropped down again onto the steel pipes, thrashing her legs about and squealing uncontrollably. Her audience was loving this view. Her display would have won her a job in any seedy strip club.
This went on for a good few minutes before Jenny eventually settled again. “Please let me go now” she sobbed to anyone that would listen. “You`ve had your fun now please untie my hands.”
Sue came up and untied Jenny’s hands, but she was held by the other girl whilst her arms were pulled in front of her and tied again. The two girls lifted Jenny from her torture frame and stood her up, but with her hands now tied at the front she was not able to run them over her aching bottom. She was turned to once again face her audience. For the first time they could see the state of her face. Two bloodshot eyes with tears streaming down her cheeks, snot running from her nose. Her body also bore the marks from being pressed against the steel poles. They broke out into a spontaneous applause of appreciation at what she had just allowed them to witness.
“Come here miss” said Steve. Jenny tried to walk but the first step caused agonising pains in her rear. Sue and the other girl that Jenny didn`t know helped her slowly and carefully down the steps and stood her in front of Steve. “Now young lady, was that what you wished for” Jenny said nothing. It was all she could manage to stand, twitching from one foot to the other to try and somehow stop the pain that was engulfing her devastated naked bottom.
“Well,” said Steve “I think that concludes your punishment. Ms Benton, please bring Ms Harris her clothes, and release her hands.
For the first time Jenny was able to touch her bottom, she pressed her hands to her burning cheeks. It felt comforting, but did nothing for the pain.
Sue had put the basket containing Jenny’s clothes on the floor. Jenny knew her panties wouldn`t be returned, but she couldn`t see her blouse. “Ah” said Steve “you made a little mess on my factory floor. I though you should donate your blouse for us to clean it up.” Jenny’s eyes widened. All she had was a flimsy skirt and a semi transparent bra to go home in. Wasn`t her humiliation and pain enough for this guy.
Despite her throbbing backside, Jenny was very aware that she was still standing in front of a group of strangers in all her naked glory. Enough was enough. She slowly got dressed. The skirt was not easy. Pulling it every inch across her poor bottom was agony. Once in her skirt and bra she decided not to attempt her socks and shoes and asked Toni to take them.
Steve escorted the three girls to the door and watched as Jenny yelped as she slowly lowered herself into the car.
The drive home was not fun. The girls didn`t really speak. Jenny was trying desperately to keep her arms across her semi-naked chest but had to keep lifting herself to take the weight off her backside. Every bump in the road caused her skirt to chafe against her wounds. She was sure that many a passing lorry driver or bus passenger had caught a glimpse of her almost naked boobs spread nicely by her seatbelt but there was nothing she could do.
When they eventually arrived at Jenny’s the girls were now feeling quite sorry for their friend. Anna went to open the door whilst Toni wrapped her jacket around Jenny’s exposed torso and walked her slowly up the path, each step causing her to wince.
Inside, Jenny slowly inched back out of her skirt. “That`s gonna hurt for a long time” said Anna, staring intently at Jenny’s purple bottom. They helped Jenny to her bedroom and she lay face down on the bed. “Leave me now” she said. “We`ll talk about this tomorrow”
Now alone, Jenny began to sob. Her bottom was still an inferno of flame. How long will this last, she thought. When will I be able to sit down properly again. Why oh why did I ever agree to this?
It had been about three months now since Jenny’s caning and her wounds were healing nicely. It was still possible to see the six marks that were once nasty weal’s across her bottom, but they were now fading pink hazy lines.
Jenny had experienced her fantasy – never did she realise how devastatingly painful it would be – but there was still something missing. Something that needed to be done for final closure. During her caning, Jenny had taken Johns cock into her mouth. She needed to drink his cum. Why, she didn`t know, but this had to happen to complete her fantasy. She needed to taste the man who had caused her so much physical pain.
She knew Toni was able to contact John, it was her who had arranged his services in the first place, so again she confided in her friend. She needed Toni to contact John again and see if he was willing to give his services one more time.
Jenny didn`t know if John was married or not. She couldn`t remember seeing a ring but at the time she was not in any fit state to notice. But hey, what the hell, he`d already groped her boob and put his dick in her mouth, one little suck couldn`t do any harm and it would stay their little secret.
A few days later Jenny got the news she was hoping for. John was well up for it but would need to come to her flat. Of course he was up for it, she thought. What 43 year old guy is going to refuse the offer of a blow job from a fit nineteen year old blonde? Jenny was happy with using her own flat. She would feel safe in her own surroundings where she could be in control, and also dress for the part.
On the Thursday night that had been arranged, Jenny dressed in only a rap around silky pink dressing gown, fastened with a cord around her slim waist. Although this gown came down to just above her knees it was very light and clingy, defining the outline of her body very clearly. It seemed to be part of her as she moved, coming alive as her boobs moved freely underneath. She didn`t wear any make-up, feeling more natural and sexy without.
Butterfies entered her stomach as a knock came to her door. She opened the door gingerly, using it to hide her body as she peeked around it. After all, anyone could have been on the other side. She smiled as she saw John standing there and ushered him in.
John eyed her up and down; appreciative of the way she was dressed. “Hi Jenny, good to see you again”. Jenny didn`t speak. She took Johns hand and led him to sit in a chair.
Standing directly in front of him, she began to slowly gyrate, her hands caressing her body and moving up to her boobs, massaging them over the material of her gown. Her movements were causing her gown below the waist cord to dance around giving John occasional glimpses of her upper thighs, but not quite revealing her pussy. Slowly, Jenny undid the cord around her waist. Her gown now fell open at the front and her continued gyrations caused it to float from side to side giving John a close up full frontal view of her naked torso. Lifting her arms to her shoulders she slipped the gown off and let it drop to the floor. Turning away from John she bent to touch her toes, legs apart just enough to give John a ring side view of her pussy no more than a couple of feet away from his face.
“You can still just see the marks” she eventually said. “Feel how smooth the skin has returned.” John placed his hand on Jenny’s bottom, deliberately letting his fingers stroke over her pussy lips as he slid his hand from one cheek to the other, feeling the beautiful texture of skin that he had once punished so violently.
Jenny stood up and turned back to face him. Although again naked and vulnerable, she felt pleasure as she watched Johns eyes scan over her. She was now in control. She moved forward and straddled him. Kneeling across his legs she pulled his face towards hers she kissed him passionately on the lips as she directed his hand between her well spread legs, giving a little sigh as his finger entered deep into her sex. She let John explore her for a while before gently pulling away to kneel in front of him. Slowly undoing his flies, she pulled his trousers to the floor. Her hand rubbed the front of his boxers. “I think you are ready for me now” she said as she pulled away his pants, his dick now totally exposed and standing to attention. John’s dick was impressive, about seven inches and quite thick, also circumcised.
Jenny removed John’s clothes from around his feet so she could spread his legs and be free to go to work. John had used his expertise to its full on Jenny’s bottom a few months before, now she was going to use her full expertise on him. She lifted his dick in her hand, gently moving her fingers up and down its length. With it held towards her she bend forward and began to tease the tip with her tongue. John gasped at this and Jenny looked up towards him. Seeing him staring at what she was doing, she smiled and took his manhood deep into her mouth, clasping her lips around its shaft. Slowly she began to slide her mouth up and down, all the time flicking at the end with her tongue. She knew from Johns movements that he was not going to last too long, and this became more evident with the salty taste in her mouth from his pre-cum. She began to work her mouth harder, his shaft now well lubricated from her saliva and she could feel it begin to pulse against her lips. Suddenly Johns hand gripped on Jenny’s head ensuring no escape as he exploded a sea of warm sticky cum into her grateful mouth. The pulses seemed to go on for ever, filling her mouth to the point she feared she was going to choke, but there was no way she way going to release her grip. She was intent on enjoying this for as long as she could, her tongue pushing this avalanche of seamen into every part of her mouth and around her teeth. This taste was going to stay with her for a long time. Eventually she slowly let Johns dick slide from her mouth, mainly because it was losing its hardness. Still with his dick in her hand she lifted her head up towards his face and opened her lips to show him her mouth swimming in his cum, before swallowing it in a single gulp. Jenny was not quite finished. Johns cock had weeped a small amount of cum since its release and she now proceeded to mop this up, sucking on and licking around his now placid member. This was now very sensitive and caused John to flinch.
Jenny knelt down on the floor and watched John as he slowly recovered. As his eyes met hers they both smiled a knowing thank you. Jenny offered him his clothes from the floor to get himself dressed.
As John stood there now fully clothed Jenny went to a draw at the side of her coach. She took out a small hanky and turned again to face John. This was a special hanky she had bought especially for tonight. It was pure white and had `Jenny’ written across one corner. It came in a little polythene bag that had a sealed top. Jenny had become very aroused down below during her nights work and she now had a little gift for John. Staring him straight in the eyes, and still totally naked, she used the hanky between her legs to dry her dripping wet pussy. She then folded the damp square of material neatly to fit back in its polythene container, sealed the top and handed it to John.
“Just a little something to remember me by” she said as she opened the door for him to leave.
Stepping into the doorway, John turned to take one last lingering look at this perfectly formed naked body in front of him, belonging to an amazing girl who had offered him her naked bottom to be caned with no mercy, had actually asked to give him a blow-job, and had left him with a little memento of the scent of her most intimate juices. Most men would pay a kings ransom for what this young girl had actually requested of him.
Alone with her thoughts, Jenny lay on her bed thinking of the events that had unfolded over the last few months, tasting in her mouth the man who had so recently tortured her body beyond imagination. Slowly rubbing her hands tightly over her pussy she had the most amazing orgasm. This was her new fantasy.
