0 comments/ 26602 views/ 2 favorites The Perils of Penelope By: decimus Stephen checked his watch. Fifteen minutes to the end of the working day. He began his usual 'home time' ritual by closing down his computer and then moved to put away the long lists of cash flow forecasts and bank statements. The business was doing well, but it could be doing better. One more big client and things would definitely be looking good. That wasn't his department though. His organised mind ran, quite simply, to organising. He did not have the flair and gut instinct required to create and sell their services. Those skills and responsibilities belonged to Penelope. A tentative knock on the door interrupted his thoughts. Speak of the devil and there she was. All designer clothed and power dressed. Penelope had the classic look of those top-drawer 'girls in pearls' but she was driven by more than a desire to go grouse shooting on Daddy's estate. There was something different about her, something that got the clients going, something that, because he didn't possess it himself, Stephen could never quite give a name. Whatever it was, young Penelope had it; and that, most of the time, was the secret of their success. "Stephen," She said, her voice unusually gentle. "The Johnstone file. Could you review it for me?" He looked up, directly into her blue eyes, noting the slight flush to her cheeks. She was a capable woman. It was not often that she asked for his help. He checked his watch once more. The gym could wait. "Leave it here." He replied. "Come back at six and we'll go over it." Then he watched her as she placed the file on his desk, her eyes unable to meet his. Half an hour later he knew all he needed to know about the Johnstone case. This was a company that was clearly in the market for their services; that would just as clearly have benefited from them, Yet Penelope had somehow overdone the selling. Johnstone's initial enthusiasm had turned to indifference; whatever technique she had used had been the wrong one. It happened sometimes; those who are blessed with flair and creativity can occasionally overdo it, turning a money making chance into no chance at all. At six precisely Penelope knocked on the door once more. Stephen motioned her in and took one last look at the file before closing it with a snap. There was no other chair in his room so she could only stand in front of his desk with her hands clasping somewhat nervously in front of her. Taking his time Stephen looked her up and down, taking in the soft curves of her body encased in the armour of her city suit. Normally he would have been more subtle in his appreciation of her, but they both knew that with this case Penelope had made a mistake. Consequently he felt free to take a few liberties. "You flirted with him didn't you." He said. It was not a question. Flirting was Penelope's favoured selling technique. She nodded. "Say it." Said Stephen. Penelope looked at the floor. "I flirted with him. The man from Johnstone's," she looked up at him, defiant, "but, he liked it, and it was only flirting!" "I'm guessing," Stephen interrupted, "but I bet he liked it when he was on his own. It was only when you flirted in front of his secretary that he changed his mind." Penelope looked down again and then up at him once more. She was always surprised when he saw through her wily ways. She operated on a quick, instinctive level. His strengths were more thoughtful. "How did you know?" She asked. "You should have checked their headed paper and the company search I had done more carefully. His secretary is actually his common law wife; and she owns just as much of that company as he does." "Oh." Said Penelope. "Yes." He replied. "Oh." Stephen was enjoying the power he had over her. He knew she was used to getting her own way. Next he let the silence work on her; allowing the foolishness of her error to hit home. She was only ever this vulnerable when she was in the wrong. "I'm sorry," She said. "It won't happen again." "I'm going to make sure of that. You of all people should know how important it is to pick up a client like the Johnstone Company." Penelope had her eyes firmly fixed on the floor. Stephen looked her up and down once more. He sighed, "I'm going to have to spank you, Penelope." "That's outrageous!" She cried; then she noticed the serious set to his jaw. Penelope quickly thought it might be better to plead. "No, please, not that.." Stephen was firm, as he knew he had to be. "Penelope. You know why you are here. You know you deserve it. If you argue it'll just be a harder, and longer, ordeal." She paused, caught between her instinct to rebel and her knowledge that she was in the wrong. Stephen believed that it was at moments like these that she was at her most beautiful. "Look." She said, "I made a stupid mistake. I'll do anything to make amends; but, please, don't spank me." "You decide, Penelope." He replied. "I can go to the board with this or I can tan your backside." He paused, then added, "Anyway, you say you'll do anything to make amends. So you'll certainly be able to put up with the minor inconvenience of having to stand for the rest of the afternoon." It only took her a few moments to make her choice. Penelope nodded, then her hands fell to her sides as she waited for his next instruction. "Say it." Stephen's words brought an increased blush to her face. Eventually, Penelope forced the words out, saying, in a small voice, "Please Stephen, I deserve to be spanked." Stephen spoke slowly and clearly, knowing that each word would work it's different magic on them both. "Undo your hair" He said. "Lift your skirt up to your waist. Take your knickers down to your knees. Bend over my desk." He paused. Penelope's blue eyes were burning into him. "Do it in that order, and do it now." He loved to watch her; and she had discovered that she loved being watched. Somehow his firm tone and watchful eyes pushed the right buttons. She wanted to provoke him. In moments she was tossing her long hair loose from it's coiffure. Then, with legs slightly apart, her delicate fingers took the hem of her knee length, pleated skirt and raised it up, above her stocking tops and past her flimsy, high cut knickers. With one hand she held it at waist height. Stephen ran his tongue over dry lips, tasting his own anticipation. He could sense that it was matched by the young woman in front of him. As his eyes roamed over what she had freshly revealed he felt the familiar stiffening of his flesh. He was charmed by her charms, bewitched by her chemistry. She usually dictated the way things should go, so, it was hard to set the pace himself. "Don't think that such a blatant display will make it any easier for you." He said. "Take that excuse for a pair of knickers down. Now." He sounded firm, harsh even; but they both heard the catch in his voice. She was getting to him. He resolved to take it out on her pert buttocks. There were two sides to it for Penelope. On one hand there was the rush of blood to her loins that she was experiencing as she posed provocatively for him. On the other there was a certain sense of shame at what she was doing; a rush of blood to her head if you like. The two feelings combined to create a strong emotional brew; it was always surprising, but she liked it. It rose to a crescendo when she was removing her knickers. When her carefully trimmed curls came into view, as his cool eyes feasted on the sight of her swelling mound she became acutely aware of her own power. She leant forward onto his desk, her eyes on his, then flicking to his lips, and then quickly to the squirming bulge in his trousers. "Are you ready?" He asked. "Yes." She replied, thinking, in more ways than one. She was surprised though, when he kissed her. He had never kissed her before. His tongue was warm and wet; pleasantly roaming inside her mouth; her own tongue pressed against his, tasting what was to come. Then he thrust his hands down the loose neck of her top, his fingers somehow finding the stiff buds of her nipples straight away. He squeezed gently, allowing them to stiffen further, and then squeezed again. Penelope's pussy throbbed in response and she groaned into his mouth. Abruptly Stephen stood up, bringing his own stiffness to within inches of her open mouth. She watched as he began to unbelt his trousers, surprised at how much she wanted to mouth his fleshy pole. So near, she thought. So near and then so far, because Stephen moved away, around the desk. The next thing she felt was his cool hands on the curved flesh of her bum cheeks. Cold fear replaced hot anticipation in her heart. He was going to spank her. Oh God, he was going to spank her with his belt. Stephen swished the leather belt through the air, once, and then twice. The third time he cracked it down hard onto the cheeks of Penelope's arse. Then because he liked the way she yelped, he did it again. Two red stripes criss crossed her otherwise alabaster cheeks. She had cried out both times but she'd also held her position. He was pleased. Stephen caressed her soft flesh feeling the cool and the warmth of each stripe. His fingers strayed further and he heard Penelope sigh as they found her wet pussy. He lingered there, touching her, teasing her. She rocked back against his hand, hungry. Two more swift cracks of the belt assailed her sweet posterior. Penelope's hands gripped the desk top. White knuckled she licked her lips. She didn't know how many she would have to face. She hoped he would stop when she was ready. Already the heat from her abused backside was throbbing, and the different heat of her wet cunt was mingling with it; changing the pain and being changed by the pain. She heard the belt fall to the floor, felt one, and then two of his fingers slip inside her. There's nothing like the sensation of being filled, she thought. Slowly In and slowly out; in and out; his rhythm equal to the hot throbbing. Then he used his hand in a different way, spanking lightly on to her flesh. Her skin began to get that crimson glow. Now, only one hand supported her body on the desk. The other had stolen between her legs and was gently circling the hard nub of her desire. Stephen watched her fingertips rubbing around her clitoris and became acutely aware of his own desire. He channelled it though, spanking her harder, making her gasp with the delicious pain. He stood behind her, and before long was pressing himself against her while still spanking her reddened flesh. In turn Penelope ground her hips back at him; slipping her fingers back, groping for, and finding, his hard cock. Stephen stepped away from her questing fingers. Slowly he unzipped himself, enjoying the sudden freedom. He placed the head of his thickness at her entrance, rubbing her with it, making it wet, teasing them both. Penelope gasped, "Fuck me, please, fuck me." He slid his length gently into her, relishing the joy of pushing himself inside her velvety wetness. Then he tried to recapture the feeling and thrust again, and again. His hands rested on her hot flesh. Once more, to the rhythm of his own cock thrusts, he began to spank her. Punishment and penetration, pleasure and pain; waves of both washed over the unfortunate Penelope. Mind you she wasn't complaining. Her fingers nestled between her thighs once more, circling and pressing wherever a little extra sensation was needed. She loved the feel of him inside her, thrusting, faster now, deeper. She loved the feel of his hands on her burning cheeks even more. That was what she needed. She'd known it the first time she'd seen his hands. They were delicate, fine boned and yet big enough. His touch was the gentlest and firmest that she'd known. "Yes." She said, and ground her hips back at him, wanting him further inside. "Yes." He replied, reaching forward to grab her hair, so that he could pull himself in deeper. He looked down once more, saw his bigness entering her, felt himself inside her, knew that he couldn't hold it. Hot sperm jetted into her wetness. His coming pulsed inside her, pushing her own body into a screamed orgasm. "Fuck me!" She said. "Fuck the naughty girl!" It was too much. Papers flew and a telephone hit the floor. Stephen and Penelope collapsed onto the desk, laughing, gasping, released at last. For a moment they held each other, then, slowly, reluctantly, he had to let her go. It hadn't been easy working for a woman; not at first. Not if you were like Stephen. Then, after a while, he'd seen just how good she was. Let's face it he decided, she's paying my wages. Which means I'd better give her all the help I can. Penelope didn't make many mistakes; maybe two or three in a year. The first time that she'd asked him to correct her behaviour he hadn't been too sure about it. She'd really had to plead with him. Of course, these days it was a labour of love. The Perils Of Penelope Pitstop As a child I used to love watching all manner of cartoons (as a matter of fact I still do) but one that particularly sticks out in my memory is "The Perils Of Penelope Pitstop". Not for it's great scripts or animation but for the weekly concept of a beautiful, seemingly helpless blonde heroine being hunted and tormented by her Guardian's secret identity, The Hooded Claw and his men. That masked villain tried time and again to do away with the beautiful Penelope without any success but the mere thought was enough to set my young mind racing. Just once I wanted him to win, to succeed and have his wicked way with the helpless innocent heroine, just once I wanted the bimbo to lose! But not to see her perish though, nothing quite so extreme, no my impressionable burgeoning mind wanted something much more sexual and carnal for the character, that she would receive the damn good fucking she so clearly needed. In fact, in retrospect, my love of all things non-consent and reluctant (in terms of erotic stories, magazines, films and fantasies) would have blossomed while watching the cartoons and wishing for the bad guys to lose. All of which I hope explains why I've written this story now and in the manner I have. Please remember to vote and leave your comments at the end and keep in mind it is purely based on the fictional cartoon characters. * Penelope Pitstop, Heiress to a vast fortune, is in perpetual peril from her fortune seeking guardian, Sylvester Sneekly, who unknown to her is really that villain of villains, The Hooded Claw. Penelope sat in Sylvester's office and flicked her luscious blonde hair and filed her fingernails, to all intents and purposes she looked like she wasn't listening to his nasally whine but she was. Sylvester for his part wanted to jump across the desk and strangle the blonde bimbo who was keeping him from his rightful fortune, all she had to do was die and he would inherit it. Still he couldn't be seen to perpetrate it, hence his act now, all sweetness and light as he told young Penelope of a maiden Aunt Bessie who had died across state and had left Penelope a valuable clock in her will. "Why I do declare, I do not recall any such relative! However, if the sweet little old thing wants me to have that heirloom then I must get right over there!" And with a shine of her white goggles and another flick of her hair Penelope rose up, accepted the directions from Sneekly and flounced out the door of his office, allowing the glasses wearing Guardian to sniff her sweet aroma and affording him the perfect view of her bubble shaped ass disappear from his office in her figure hugging leggings. He waited a full minute until he heard her cartoon car start up and rev out of his car park before dialling to the house he had just sent Penelope to. "Bully Boys? She's on her way, make sure you get her and no mistakes this time!" The Hooded Claws goons nodded to each other and chuckled while back in the office Sylvester Sneekly (via a quick costume change) had been replaced by the magnificently cackling, evil Hooded Claw. "Hahahahahahahahahah!" And with that he speeds from the office to pull the string of the cords of his latest carefully constructed plan to rid the world of sweet Penelope Pitstop once and for all. * The drive passed in a flash, Penelope spending most of the journey powdering her cheeks and carefully applying more and more lipstick as she drove. She paid little heed to the bright yellow sun nor the two-dimensional cacti and rocks at the road side, nor still the fact that the road was getting more and more remote and indeed, for the last half hour she had not passed a single car of house. Aunt Bessie must have lived like a hermit, mused Penelope when she finally looked up to see the rickety shack in the distance that Mr. Sneekly had sent her to. Behind the old house's net curtains the Bully Brothers watched intently as the sexy blonde got out of her car, they could hardly contain their excitement as she turned her back to them and bent over to collect her handbag from her convertible. The sight of her amazing ass was too much. The pink material of her trousers was stretched to the limit and both hoodlums were having similar, carnal thoughts at that moment. She turn and straightened and wiggled her way towards the front door. While Bully #1 prepared his disguise by adjusting his butlers outfit Bully #2 made sure her had his ropes and cords at the ready. Penelope barely registered the rundown old shack of a house, to her such matters were superfluous she walked to the door (being careful to keep her pristine white boots clean) and knocked on the heavy door. It opened altogether too quickly, like the butler had been waiting for her and he looked somewhat familiar but Penelope was too trusting to question that. "I do declare, what a quaint old place! My name is Miss Penelope Pitstop and I am here by way of Mr. Sylvester Sneekly to collect a heirloom left to me by my late Aunt Bessie." "Um, yeah, step this way Miss Pissmop, ah I mean, Pitstop." She followed him through the dusty corridor and into a living room that had been stripped of all furniture, just an old clock ticking on the far mantelpiece. She stepped towards it but before she got far a rope was wrapped her waist and arms and pulled tight. She squealed in surprise. "Help! Help! Hel.." Her last plea cut off by a gag placed between her red lips and pulled tight. With her silence ensured, her arms neutralised all it left Bully Boy #2 to do was wrap the remains of the rope around her slender ankles and render her helpless. "Good job, now lets lift her up and take her to the kitchen while we wait for the boss!", grunted the happy Bully. * Laid flat across the bare wooden table, Penelope had time to consider her predicament. This was obviously another cunning plan by that evil Hooded Claw. This time it looked like the madman had her right in his clutches. At least she had been able to wriggle her hands free enough to press her secret alarm button on her belt to alert her usual saviours, the Ant Hill Mob. Hopefully, those loveable midgets would already be on their way to the tracker and to her rescue. Still they were pretty much useless fuck-ups, she thought, perhaps she should employ other methods to achieve her safety. She began to writhe and moan into her gag until one of the dumb Bully's released the gag and allowed her to speak, his crotch just inches from Penelope's sexy mouth. "I say, am so uncomfortable here and my mouth is so dry, I surely could do with something to suck on. Say something thick, and manly and meaty and cock flavoured!" It was the correct approach as subtlety was not to be used on the Bully Brothers. Before long he had undone his trousers and unleashed a hefty cock and presented it to Penelope's mouth. "Oh well, the things I do!" she said before gulping a mouthful of cartoon cock into her. Well as Bully #1 received a divine blow job from the blonde Goddess it came as no surprise that his compatriot wanted to join the action. Penelope felt the belt of her pink trousers being undone and then the tight pants being hauled down. As she felt the hard skin of another erect cock press against her she concentrated on sucking the cock in front of her. "I always was an ass man", proclaimed Bully #2 as he helped himself to a slice of prime female meat. So there our heroine was, tied and stretched over a table and taking double dick, one in either end, one in the mouth and one in her ass and really, except for the imminent arrival of the Hooded Claw and his latest plan to do away with her she was actually quite enjoying herself. It certainly wasn't the first time Penelope Pitstop had taken double penetration from multiple cocks, what with being quite the loose nymphomaniac in her spare time (oh, did you not know?). Even better, the dumb clods had undone her bonds as they had neared climax and as she readied herself to take their thick seed into her mouth and into her asshole she also studied the room to find a possible exit. The Bully Boys heaved and grunted and filled the blonde with their seed from both ends and as they stood back to try and recover Penelope made her break for it. She had timed it perfectly and was at the door before they realised what was going on, now all she had to do was get out and reach her car and get out of here. She flung the door open only to come face to face with her evil nemesis The Hooded Claw. In seconds she was in his clutches and being dragged back into the kitchen. * Meanwhile, the Ant Hill mob and their car Chugga-boom have managed to get lost and, as per the Claw's tinkering with signs are headed straight towards the edge of a cliff. Can they reach Penelope in time to save our Southern heroine? Can they save themselves? We'll see! * Further down the deserted valley the Bully Boys (fresh off a real roasting from their boss) have Penelope hoisted overhead, having trussed her legs and arms again and, led by the Hooded Claw are headed towards the railway line that lies half a mile past the house. "That's it you dolts! Let's see if you can get this right at least!" The twin hoodlums kept their heads down and their grumbles to a minimal, they knew they had fucked up but neither would have swapped what the blond nympho had done for anything. Still now was time to do what they were paid for. They had just reached the railway tracks and the boys knew what to do next. As The Claw detailed his villainous plan to the helpless Penelope they undid her bonds only to retie them but this time actually around the metal sleepers of the track. Poor Penelope was ties tightly across the rails, her head over one side and her feet over the other. "Ha! This time Penelope Pitstop I've got you! You won't escape this time, in just ten short minutes the three thirty train will come along this canyon travelling at up to 100 miles per hour running right over and through your pretty little body!" Finishing this proclamation The Claw despatched the Bully Boys back to get the escape car ready while he stands over the helpless Penelope relishing his moment of ultimate victory over his long time rival. "Well Penelope, it looks like it's all over for 'little ole you', doesn't it? Got any last minute requests? Please beg me for mercy one last time!" Penelope finished chewing the wad of gum in her mouth and opened her sweet little mouth. "Why Mr. Hooded Claw, I do declare that from this position down here I do think that you are somewhat aroused, how about you let me do something about that?" Well if his Henchmen had been unable to ignore the prospect of Penelope Pitstop's oral ministrations so was their boss. Those sweet pink lips, those wide, innocent eyes fluttering up at him there was nothing for it but for the Hooded Claw to yank open his trousers, release his small, hard cock and sink to his knees over Penelope's head. She was right he was so aroused as her lips circled around his cock while his mortal enemy was tied to the immovable rail tracks. In common with many evil super villains, The Hooded Claw had a real problem with premature ejaculation and with just a few short sharp sucks Penelope found her pretty mouth being flooded with the sour, watery semen of her captor and her with little option but to swallow it down to let her breath. Of course The Claw thought he had lasted ages and quickly zipped up and got out of there, leaving our heroine to lie across the rail tracks and strain her ears to listen for the approaching express train. * Meantime, the Ant Hill Mob have rescued themselves and made it back to the proper road and are speeding towards our damsel in distress, stopping on their way to spin the sign back to normal, Clyde urging their faithful ride to make greater haste. They passed The Claw and the Bully Boys at such a speed that the villains swerved off the track and crashed into the river to be swept away amid much shaking of fists and squabbling while trying to escape their car. "There's Penelope's car Clyde" announced Yak Yak. "Quiet, I can hear her shrill call for help" said Zippy and Chugga-boom kept on going past the shack and towards Penelope's rescue, but will they be in time? Of course they will. They rounded the corner on two wheels and came to a suffering halt at the railway tracks to find Penelope wriggling and trying to use a hair pin to free herself. "Penelope! There's no time to waste fellas , let's get her untied!" But the blonde had a strange look on her face as she licked the last vestiges of the Hooded Claw's cum from her lips. She rather liked the idea of being helpless and in mortal danger and was as wet as hell between her legs as a result. "Now boys! That li'l ole train isn't going to be here for a few minutes yet. I got an awful hankering for some short man cock, so why don't you untie my legs, pull down my little ole trousers and panties and help yourselves to all the pussy pie you boys want. It's the least you boys deserve after coming to my rescue once again." The vertically challenges faux gangsters needed no further encouragement and almost before the last word was out of Penelope's mouth the midgets had her clothes off and their small cock in their hands and ready for use. Fortunately these boys were able to get two cocks at a time inside our heroine's pussy. A fact Penelope particularly enjoyed as Clyde and Dum Dum's dicks banged together inside, really stretching her tight, wet pussy walls from within. Of course Penelope was more than used to the Ant Hill Mobs shortcomings in that they were all notorious for their premature ejaculation and she was quickly accepting another two of her miniature saviours cocks into her while admiring the clear blue sky above her and rather dumbly wondering what that rumbling was (she was a blonde after all). In fact it took almost no time at all for the Ant Hill Mob to spunk their seven loads of cum up inside Penelope's pussy and they were back inside Chugga Boom and heading home happy not that longer than they had arrived. It was only after they were driving past the shack and Penelope's pink sports car that they suddenly remembered that they had not tied our heroine from the tracks! Which was pretty bad as they could gear the shrill scream of the steam engine whistling along the canyon and then far past into the sunset. "Penelope!!!!" cried all the Mob. But they needn't have worried, as they arrived back at the tracks there was Penelope, now stark naked (and cum dripping down her shapely thighs), filing her nails and looking as coquettishly as normal. "Oh hi boys." "But Penelope, how? Where? When? How did you escape?" "well all that friction of you nice boys fucking me caused my roped to fray and I was able to pull the remainder off with my teeth. Thanks boys." And with that she picked up her outfit and strode back towards the shack, taking the time to top up her all over tan by strolling in the sun as the Mob admired her perfect body. Meanwhile, in a river further down the canyon, The Claw and the Bully Boys are clinging to a log and he takes the chance to ball his hand into a fist and call out in frustration. "Curses! Foiled again! But don't, I'll get you yet Penelope Pitstop! I'll get you if it's the last thing I do!" Which was pretty dumb as by shaking his fist he lost his grip on the log and was swept away leaving his big green hat stuck on a branch and the Bully Boys sharing a small smile.