TRAPPED IN THE HIGH RISE After weeks of cleaning toilets and floors in half the buildings in the Loop, Debbie Collins finally was assigned the prestigious North Michigan Avenue building she wanted. Several weeks earlier, she had taken a part time night job at a large custodial company. She, of course, was not a cleaning woman, but a high powered advertising agent on her way up. She was determined to get into her main competitors offices to see what they were up to and this was a good as way as any. Working days at her own ad agency and the nightly custodial work, were wearing her to a frazzle. But, now, she was IN!!.......and she wasted no time! The first private office she entered was small, but my god, files were left open on the desk and the computer was still on! Somebody's security sucked, she thought! Her heart thumped in her chest as she started making copies of everything she could find......including making disc duplicates. She was alone on the deserted 6th floor, but every noise startled her. After 15 minutes of diligent copying, she was deeply engrossed in her industrial espionage, and did not hear the footsteps. The man stood for several minutes at the office door watching her. "WHAT! are you doing in my office?" he shouted the first word. Debbie jumped with fright! Files and discs crashed to the floor. "Just......just cleaning.....AND YOU SCARED THE HELL OUT OF ME!" she answered and shouted, figuring maybe a good defence would be a good offence! "BULLSHIT! I've been watching you for five minutes! the man answered, still standing in the only door way. Debbie looked at him. Jesus! A Nick Nolte! Big, dishevelved blonde hair, white shirt sleeves rolled up, no tie, suspenders. "Wait just a minute! I KNOW YOU!" he stated. "I mean, I don't know you personally, but you work for...... .......YES!......Baxter and Ames!" "NO!......I don't!" Debbie replied. "I work for Chicago Custodial Services," she emphatically added. "Well.....that maybe so, but you also work for Baxter..... ........I remember the red hair!" he argued back. "YOU'RE A GODAMN SPY!" he shouted. Debbie was trapped. He knew her all right. He even described a dark green two piece suit she wore at an ad luncheon. She would think of it later as to how he had noticed such details, but not now. He grabbed her purse and pulled out her wallet. She did not protest. He pulled out her driver's license and placed it in the copy machine......set to "Enlarge". He held up the paper. "Well Miss Debbie Collins, of 1640 N. Damen, what do you think will happen when this gets out?" he asked, still standing between her and the door. No answer. "First, the custodial firm will lose our account and maybe 30-40 people their jobs. And you will probably lose yours, and be black listed by every legitimate agency in the city and state. And, oh yes, an arrest record. Probably probation, but my boss would push for the maximum.....1-3 years, I would think," he fired the consequences at her. Debbie started to plead. Plead for the lost jobs of the cleaners and her own skin. Offering all sorts of promises for his silence. "Tell you what, Debbie," he started to say, "you are going to sit down and write out a confession right on this paper with the copy of your license and photo, and that you will also write out in your own hand, that you will submit to the punishment I will inflict, which will include, but not be limited to, a bare bottom spanking! Maybe THAT will teach you to play fair and respect the rights of others!" he finished. Debbie was stunned! She was 34 years old and had not been spanked in over 20 years! Her mind raced. THERE WAS NO WAY OUT OF THIS! She HAD to do it. A spanking and it was over. How bad could it be? This was a sophisticated man, not some mugger! "OK.......a spanking, and this is all over? You'll not bring any charges?" she asked. "That's right. Your choice. You have 5 seconds to make up your mind." he answered. "I agree," Debbie answered and started to write out the confession and the particulars as the man dictated the words to her. When she finished, the man took the paper and read over it, folded it, and placed it in his pocket. "GOOD! Now take off all your clothes." he stated so calmly! (OH GOD!) Debbie thought, this is going to be TERRIBLE! Her eyes teared and nose sniffled as she started undressing. First, the custodian smock, then her blouse, slacks, shoes and socks. She turned from him and removed her bra, then as fast as she could, pulled down and stepped out of the panties! She was naked. A figure that would be considered "very good" by most anyone. He barely glanced at her and said: "OK, let's go," and stepped out of the door way. "Where?" Debbie asked, gulping at the same time, while moving towards the door. When she was outside his office, he locked the door! Her heart was thumping with fear and anticipation! Her vulnerability of having her clothes locked away terrified her! With a bow, and a cavalier wave of his arm, he said, "apres vous" as he motioned for her to lead the way down the hallway! The hallway floor was polished terrazzo, and it was icy under her bare feet. She felt her nipples erect in protest to the cold. She started to walk down the hallway in the direction the man pointed. "All the way down," he said. To Debbie, the hallway looked a mile long! He was a few paces behind her. She dared not look back at him. She KNEW what he was watching! She tried to walk "dignified"! Her body was betraying her. She could feel droplets under her arms, squirts of arousal in her groin, the pressure on her bladder, stomach growling, all the while her feet slapping against the cold stone. She was acutely aware of the movement of her bottom, as the cheeks moved and jiggled with each step. NEVER, had she felt so embarrassed and exposed! What if someone comes by!!! Finally, the reached the end of the hallway and they stopped. He pushed the button and the elevator doors opened. The same polite hand jesture told her to enter first. The doors closed and he used his key to access the 45th floor. "Stand with your face in the corner and don't make a sound," he instructed her. With a kind of weird relief, she turned her back to him and stood as told, feeling ridiculous. He was humming to himself as the elevator raced upward! "PING!" The floor bell startled her and she felt the assent slow and the doors open. "AH, Senor Ted! You are working........late.........again?" the cleaning lady said, her cheerful greeting turning to belwilderment as she saw Debbie's bare assed and motionless form! Ted pulled the cleaning cart inside the elevator and the lady followed. "Yes, Maria, you know how it is," he smiled, "what floor?" "Tweenty-seben, came the accented reply, as she looked up and down Debbie's ass and again at Ted as the doors closed and the elevator silently began its climb. Debbie closed her eyes. She could not BELIEVE this was happening! "Don't worry, Maria," he said, "I'm just taking this bad girl upstairs for a well deserved spanking." Marie replied "I see" but really did not. Debbie cringed! "Her bottom looks nice for a spanking, don't you think, Maria?" he asked the woman. "Si, Senor, I tink so," Maria blushed. They reached the 27th floor, and Maria and the cart exited. She bid good evening to "Mr. Ted", ignoring Debbie completely. Giggling as the doors closed once again. In seconds they were at the 45th floor, ears ringing. "OK, OUT! Turn right and walk straight ahead," Ted ordered Debbie. Again, her bare feet slapped against the cold floor as Ted followed. "Stop right there," he said after about 30 paces. He moved around her, unlocked the door, and ushered her inside. Then relocked the door. They were in the executive fitness center! "OK, spy, time for your workout! Get on the treadmill!" Ted ordered! "You said a spanking! What the HELL is this all about??!!" Debbie screamed back! "AND THAT'S EXACTLY WHAT YOU"RE GOING TO GET! NOW....YOU WATCH YOU'RE TONGUE OR SO HELP ME GOD, YOU'LL REGRET IT! GET ON THAT TREADMILL........NOW!" he yelled. Debbie did not like the way the veins popped out against his neck and did as she was told. She grabbed the hand rail and waited. He turned the machine on and she was forced to walk.....nude!!! My GOD! This was humiliating! Ted stood at her left side and with his open hand, started slapping her ass!!! Her legs kept moving and he kept slapping! Up and down each cheek and the backs of her thighs! It stung like hell! He increased the speed of the machine and Debbie walked faster to keep up. Ted was measuring his swats, pausing 2 or 3 seconds between each one. Again, he increased the speed. Debbie was walking fast....almost as fast as she could! Her cheeks rose and fell, and rubbed against each other as the firm hand continued to slap and slap and slap! She was breathing hard and her breasts were heaving and bouncing from the forced march and the punctuating smacks to her bottom. She did not know how long she could take this! Her knuckles were white from gripping the bar, and the stings of the slaps were exploding in her brain........and in her groin!! As a diversion, he slid his hand between her walking legs, thumb up pressing against her bottom hole, and his index finger sliding along her sex. With her eyes closed and head down, Debbie "walked" against the friction of the hand. He went to the other side and slapped her ass at least twenty more times. Debbie was squeaking out little shrieks of protest, and starting to sob. Ted shut down the machine and Debbie stepped down. Her eyes filled with tears, panting from exhaustion, and her bottom on fire! "OK, We'll finish up on the leg press," Ted stated, and led her over to the bench. "OH, PLEASE! NO MORE!" Debbie pleaded. "Not that easy, sister!" Ted replied, "now lay down on the bench, face up!" he ordered. She had to stradle the bench to lay down. Ted placed her arms over her head, and brought down the padded weight bar to the back of her biceps. The weight he added pinned her arms down. "Lift your legs to the platform," he instructed. Debbie had to shamelessly spread her legs and bend them in an "L" position to accomplish the direction. He added just enough weight to force her legs to "squat" then another 20 pounds, making it utterly impossible for her to lift the platform! Her arms were pinned over her head. She was laying flat on her back. And her legs were up and spread, with her bare split bottom hanging just over the edge of the bench!!! "You look a little warm," he stated staring at the well exposed sex lips and the pucker of her anus! "I'll just cool you down a little before we resume," he added. He took a squirt bottle and started annointing her bottom cheeks with cool water! He squirted her slit, even inserting the nozzle slightly to squirt up and down! She felt her clit throb as the nozzle touched it! Ted refilled the bottle, letting the tap run till ice cold. He started on her anus! Her cheeks were so spread, she could not even clench them closed, and her anus was wide open to his assault! The water teased around the sensitive pucker and when the nozzle inched its way inside, she thought she would die! He was using an index finger to poke at the crinkled membrane while he squirted it!!! The teasing sensations were maddening!! "There, that should cool you off and take your mind off things for a while!" he chided as he walked into the shower and dressing area. "Thought there was one of these in here," he came back saying, holding up a wicked looking wooden hair brush for her to see. Debbie's eyes were wide looking at the brush. Ted smiled then took a position at the end of the bench. He first rubbed the bristled side against her cheeks. Debbie tried to squirm against the irritation. She closed her eyes. OH JESUS! HE WAS BRUSHING HER PUSSY HAIR! He sat down like an Indian between her legs and continued to brush at her sex lips. With his other index finger, he started to coax apart the rubbery folds of her slit, letting the brush glide back and forth of her protruding clit! Debbie moaned. She could feel the arousal gripping her groin. Ted smiled as a drop of her juice leaked out. He caught the drip and guided it to her bottom hole! More moans. Just when she thought she was going to climax he stopped and brought the back of the brush down hard on her naked ass. He stood up. SPLAT! the sound was firm. There was no shock resiliency in her stretched to the max cheeks. The sting of the sciatic nerve seared her brain. A wordless shreik from her open mouth. Her reflexes tried to lift the platform. It only succeeded in flexing her thigh muscles in a useless excercize. SPLAT! to the other cheek and again the "ack...ack" of an almost wordless shreik. Five more times to each cheek. It felt like a hot iron was tearing at her flesh. He worked the brush up from the back of her thighs across both cheeks, then back again, hardly ever pausing. He set the brush down, and started again with his hand. He slapped her open sex lips half a dozen times, then the cheeks and insides of her thighs. She screamed and pleaded for Ted to stop. And he did. Only to sit back down between her legs and just watch. The cheeks were almost a bright red and twitching uncontrollably. He touched the welts here and there. Then kissed them. Then licked them, running his tongue over the indented and swelled ridges. Debbie began to breath heavier. Her belly contracted and the fire in her groin was reignited. Ted's tongue flicked at her cheeks, then in between! Debbie shuddered. This was unknown to her. The tongue teased at her anus and it pulsed shock waves to her sex. He licked and licked then started upward. Debbie moaned aloud. The tongue glided over her sex, then wormed its way inside, and up to the very top. Exploring her fountain hole and throbbing clit. Her sex lips puffed open, inviting the soft tongue. The tongue constricted itself and used its tip to flick back and forth over the clit. Pushing at it from above and below. It stopped. She looked up and saw Ted standing, taking off his clothes. "Please.......hurry......." Debbie whispered. Ted smiled. When he was naked, he lifted the weight from the platform and lifted it up, freeing her legs. He guided his erection into her and the legs closed upon the small of his back like a vice. As he knelt, he pushed his hips forward, pulling on Debbies hips to meet his thrusts. They fucked in perfect unison, each enjoying the pleasures of each other. When his hands slid up her torso and grabbed her nipples, she climaxed. Not even the pain of her bottom rubbing against the bench could hinder her orgasm. It enhanced it! Wave after wave of ecstacy pulsed through her. She could hear the squish of passion and could feel the powerful hands and hips envelope her. She was racked with climax like never before. Ted withdrew and again sat on the floor. Debbie lay panting on the bench. Her legs lewdly spread wide. She did not care. His hand reached up and touched the sensitive clit, causing the legs to snap shut like a bear trap! He chuckled. Debbie groaned and smiled. He opened her legs and crawled up over her body and kissed her on the mouth. "There, there," he said, "Now that wasn't too bad, was it?" he added and asked. She smiled her agreement. "It's getting late, and we need to start the second part of your punishment." he calmly spoke. "OH GOD! NO! I can't possibly take another spanking!" Debbie pleaded. "Oh, I know, another spanking is out of the question, for now anyway. Your ass is much to tender. I was thinking of something else." he chided. "WHAT??!" Debbie asked with alarm, breathing heavy again. "Oh......well..........I was just going to find out how ticklish you were!" he smiled, hands on her ribs. Debbie's eyes puffed out like an owl! She was horribly ticklish! She tried to squirm off the bench. Her arms were still trapped and Ted was attaching weight cuffs to her ankles and tying her down!!!!!!!!!!!!!!!!