1 comments/ 74646 views/ 11 favorites My Mistress' Skirt By: Sonny Boy Jacobsen MA'AM PART FOUR - MISTRESS FAVORITE SKIRT In retrospect, it was one of the dumbest things I have ever done! The only excuse I can offer is that I was a bored teenager on a hot summer's day, and I wasn't thinking straight. Mistress Mona, whom I shall hereafter refer to only as Mistress, and I had gone into town to go shopping. We had bought some clothes for me, but the bulk of the day had been taken up looking round places for Mistress. It was the first Monday of the school holidays, the day you realize that there really is no more school for ages, and this was NOT how I wanted to spend it. I had suggested that I could go and browse some bookstores while Mistress did her shops, but she said she wanted someone with her who could tell her what things looked like on her. I didn't really enjoy doing this, but it was one of those things you just have to do. In the three years since my father had died, Mistress and I had become close, and this was something I knew she enjoyed. So, I dutifully trailed round after her, offering comments on items she tried on. She had bought a couple of pairs of shorts, and was looking at shoes when it happened. Bored out of my mind, I was feeling a tad mischievous. Mistress was wearing a long, light summer skirt which billowed around her legs. She had crouched down to look at the bottom rack of a display; her skirt was pooled on the floor around her. Surreptitiously, I moved my foot so that it was pinning the skirt to the floor. I figured that she would try to stand up, fail, and maybe fall over. Nothing more. A bit of idle mischief which I would apologize for and pretend was an accident. Unfortunately, I had rather over-estimated the strength of her garment. When Mistress suddenly jerked to her feet, the skirt was just not up to holding her to the floor, and so ripped all around the waist! Mistress ended up on her feet, with half of her dress around her ankles. I just stood there stunned, gaping at her. Gaping, because with it being such a hot day, Mistress had chosen to come out without any panties on. So I suddenly found myself staring at her firm, naked buttocks! Several other people in the store saw her as well, and there was a chorus of gasps and giggles. Mistress whirled round towards me, her face crimson with embarrassment, and I got a look at the small tuft of raven hair that crowned her pussy. At that moment, a woman's voice said "I bet she won't find shoes to go with THAT outfit!", and everyone laughed. Mistress was just frozen to the spot, paralyzed with sudden embarrassment. I stared openly at her nakedness, feeling my cock rising involuntarily. I was suddenly conscious that Mistress could see the bulge in my shorts, and I looked at her face. She frowned at me, and I saw her eyes look down and take in the sight of my foot, still placed squarely over the remains of her skirt. Her face grew dark and contorted with fury. I stepped back, just as a kind saleslady hurried up to my mother and quickly ushered her off to a back room. She emerged several minutes later wearing one of the shorts she had bought, into which her top had been tucked. She swept towards me, caught my arm in a vice-like grip, and dragged me from the store. We marched at a fast pace to the car, Mistress never letting go of my arm and forcing me to stumble and jog to keep up with her pace whilst maintaining my balance. When we got to the car, she practically threw me inside and we drove off. I started to speak, but she cut me off "SHUT UP! Just keep quiet! I don't want one word out of you 'til we get home". When we got home, I was told to wait in the lounge while Mistress changed. I sat on the edge of the sofa, trembling with fear and guilt. I really hadn't meant things to get so out of hand. God only knows what Mistress would do when she came downstairs, but I had a feeling I wasn't going to like it! In a few minutes, she came down wearing tight blue jeans and a low-cut T-shirt. It was her usual outfit around the house in summer, designed for comfort. Yet in the light of recent events, I couldn't help noticing the way it emphasized her figure. She sat down beside me and in a quiet voice asked me to explain why I had done it. I stammered out the truth, that I was feeling bored and wanted to play a trick, but that I hadn't meant it to turn out like that, and I was really, really sorry! "So, what you're saying is that you did mean to humiliate me, just not quite as much. Is that it?" asked Mistress coolly. "No, not humiliate, I just.." "So, you think that falling into a display of shoes wouldn't be humiliating?" "Well, er, yes, I suppose it would, but..." "So, you did mean to humiliate me? Didn't you?" "Ummm, well, yes, perhaps just a little, but I didn't think..." "No, you certainly didn't, did you?!" The heat was rising now in Mistress's voice, her anger once more coming to the fore. She sat back on the sofa and looked hard at me. "Stand up and take your clothes off. I want you naked, naughty boy, right now!" Blushing, I got up and started to strip. I wasn't sure quite what was coming, but I knew I deserved it for embarrassing my Mistress so much. When I was naked, I turned to look at her. She stared at me, and I blushed some more. "Right. Stand facing the window, hands behind your head, legs a bit more apart." Nervously, I assumed the position. It felt so strange to be doing this, and I started to worry about what Mistress had in mind. She stood up, and walked slowly around me. She stopped when she was behind me, and leant forward, so her head was next to my ear. "You'd better get used to this." she said quietly. "Because from now on, you're going to be naked all the time unless I say otherwise. I've never been so embarrassed and ashamed as I was today, and I'm going to make damn sure you know how it felt." Mistress went and sat down on the chair next to the window. She stared at me for a moment, then spoke. "Sonny, I want you to realize that your punishment for this is going to be very different from anything you've had before. I imagine you thought you'd be in for an extra hard strapping and then that would be it. Well, you are going to get that, it's true. You're going to be spanked and strapped and caned and anything else I can muster. And it's going to be hard! Not just a spanking, I'm going to give you a whipping! I'm going to punish you like you've never been punished before! However, you're also going to be humiliated. I'm going to do everything I can to embarrass you, tease you and generally make you feel frustrated and wretched. Maybe then you'll understand how I felt today." I stood in front of her, trembling. I had never seen Mistress like this before. It was obvious that she was deeply upset about what had happened, and she was going to take it all out on me! I stared at her, my eyes wide with fear. Mistress suddenly jumped to her feet. "Right, keep your hands on your head and follow me." she said, walking towards the door. I followed her out and upstairs to her bedroom. Mistress stood up and piled all the pillows from the bed up near the edge. Then she went over to a drawer and took out her strap. This was a special strap made from harness leather for extra thickness and weight. I had only felt it a few times before, when Mistress thought I needed a particularly severe punishment. She smacked it against her hand and I shuddered. "Lie on the bed with your hips over the pillows." Mistress commanded. "I want that bare bottom nice and high." "Oh please, Mistress!" I cried. "Please, you can't! I'm sorry, really I am, please don't strap me! I can't take any more, it hurts so much!" Mistress's face darkened with anger and she stepped up close to me. "This is your first and last warning." she said in a voice filled with menace. "If you argue with me again about a punishment, I'll tie you down and use a fresh willow switch on your bare balls, is that clear? Now do as you're told!" Mute with fear, I clambered on to the bed. The pillows pushed my naked ass cheeks high into the air, and I shivered at how vulnerable it made me feel. THWACK! The strap hissed through the air and bit into my unprotected buttocks. I went rigid and howled as the heavy leather landed. The stroke of the strap seemed to tear into my tender flesh. "There! THWACK! Maybe this THWACK! will teach you THWACK! not to try to embarrass THWACK! Your THWACK! Mistress! THWACK!" "Oh please, Mistress! THWACK! Aaaiieee! Puh-please! THWACK! Ooowww! I'm so-sorry! THWACK! Aaahh!" I wailed, but Mistress wasn't listening. Again and again the strap arced through the air and landed on my bottom. Mistress grunted quietly with each stroke, really putting her whole body behind each swing. After several more strokes, she paused. "Sonny boy, I'm going to give you five more strokes, and I want you to count them out loud and say 'thank you, Mistress' after each one. If you make a mistake, you get two penalty strokes. Here we go!" THWACK! "Oooww! Wuh-one, thank you, Mistress!" THWACK! "Aiieee! T-two, thank you, Mistress!" THWACK! "Unngh! Three, thank you, Mistress!" THWACK! "Ooooh! F-f-four, th-thank you, Mistress!" THWACK! "Aaaahhh! Fuh-five, thank you, M-Mistress!" With that I collapsed sobbing on the bed. Mistress put down the strap and knelt beside me. "Well, dear, I hope you got a good look at my pussy for all of that pain. Now, Mistress is going to rub some cream into your butt to soothe it. We want to keep those buttocks nice and soft and sensitive, now don't we?" She giggled quietly, and stroked my hair as I lay still, weeping quietly into the bed as Mistress got some cream and started gently massaging it into my bottom. It burned like ice at first, but soon I felt the pain start to diminish slightly and be replaced by a dull ache. For the rest of the afternoon I followed Mistress around the house, still naked. When she decided to sit in the lounge and read, I lay on the sofa beside her, so she could glance across at my crimson buttocks whenever she felt like it. When she went to make dinner, I helped her when I could, otherwise I stood in the corner, hands on head. Dinner itself was agony. I asked Mistress if I could eat off the fireplace mantelpiece standing up in order to save my aching bottom, but she insisted I sit normally. Sitting on a bottom that had been so thoroughly strapped over was torture, and my eyes watered throughout the meal. When it was over, I was sent to do the washing up, after which Mistress sat in the lounge and watched TV, while I stood in the corner again. After about half an hour, she relented and allowed me to lie on the sofa and watch with her. That night was dreadful! I slept fitfully, unable to relax. My teenage libido was in full control and my cock was stiff the whole time. I did reach down and stroke it lightly, but I didn't dare do anything else for fear of waking my Mistress, who I knew was a very light sleeper. Finally sheer exhaustion overcame me and I dropped into a deep sleep. The next day, after lunch, Mistress announced we would be going out shopping. A look of terror passed across my face, and she quickly reassured me that it wasn't going to be like last time and I wasn't going to get spanked. "Just behave yourself, and everything will be fine." she said. "Although if you're a bad boy, I won't hesitate to spank you in public!" With that, she led me to her room and gave me a pair of pink cotton panties to put on. Blushing, I pulled on the panties. To my surprise, my cock started to swell, and I blushed even more. Mistress saw it and laughed. "See?" she crowed. "I knew you liked wearing girls panties! You really are Mistress little panty boy, aren't you?" "Y-yes, Mistress." I stammered. "Well say it then. Tell me what you are." "I-I'm Mistress little p-panty boy." Mistress laughed again, and told me to go put on a t-shirt, shorts and shoes. Then we went to the car and drove off. We ended up in a part of town I didn't know. It was away from the center, and seemed a little run down. Mistress parked the car up a side street. She turned to me and smiled. "I want you to take your shorts down and off!" "What?!" I exclaimed. "Here? But-but people will see!" "Do as you're told, unless you want to be bent over the front of the car and spanked!" There was no way I could bar that, so I quickly tugged my shorts down. Mistress told me to throw them into the back of the car, which I did. I looked down at myself , my lower half bare except for the thin pink cotton panties stretched across my groin. Mistress giggled and walked off round the corner. The weather was still very hot, and sweat rolled down my face as I waited in the stuffy car. Later that night, at bedtime we went upstairs to my room and I lay down gratefully on my bed and closed my eyes. Mistress fetched some cream and started rubbing it into my bottom. My eyes had remained closed the whole time, and I just tried to relax and enjoy the soothing feel of the cream. It stung horribly at first, but soon I felt it doing its work. "Open your eyes and look at me, Sonny." said Mistress quietly. I rolled onto my side and looked at her, my eyes widening and my mouth dropping open as I saw what she was holding! They were padded leather handcuffs, held together by a long length of thin chain. Mistress grinned at my reaction. She threaded the cuffs round the bedpost, just below the headboard, then fastened them briskly around my wrists. I was now secured to the bed! My hands could come down about as far as my chest, but no further. Mistress grinned at me. "I'm sorry to have to resort to this," she said, "but it seems to be the only way I can be sure you aren't going to masturbate, you little panty pervert! Now try to relax and get some sleep." After she left, I lay there stunned. Handcuffed! What's more, handcuffed with what looked very like sex toy handcuffs! My cock became stiff as I thought about being tied up like this. Of course, I could do nothing to relieve my stiffness, that was the whole point! I lay there twisting in sexual frustration for a while, and then began to think about what had just happened, what lay ahead and my mind whirled. Eventually, tiredness overcame me and I dozed. When I awoke, it was dark, and Mistress was kneeling beside my bed. Naked except for tight blue jeans. My cock leapt as I stared at her. "How are you feeling?" she asked, and I told her I felt OK, but still very sore. Mistress chuckled quietly. "Good. I intend to keep it sore for awhile." My cock throbbed at my Mistress firm demeanor. So I was right, she had been getting turned on by punishing me. She then reached over and stroked my hair. "Now, you go to sleep and get a good night's rest so you're nice and fresh for tomorrow. There's a bucket by your bed if you need it, because I'm going to leave you cuffed all night to prevent any unauthorized masturbation!" With that, she leant over and kissed me goodnight, her bare breast rubbing against my shoulder. I lay there confused, stunned and frustrated. My cock was pulsing and twitching, but there was nothing I could do about it! I tried rolling over and rubbing myself on the bed, but I couldn't get it to work, and flexing my butt cheeks like that was very painful. I also realized I would suffer if Mistress came in and found the sheets covered in cum. So I just lay down and tried to think of other things. Eventually I fell asleep. The following night, come bedtime, when we got to my room, Mistress had me lie on the bed and then cuffed my hands to the headboard as she had the previous night. Then she knelt by my bed and smiled at me. "I've been saving this news for tomorrow." she announced with a fierce gleam in her eye. "Tomorrow is going to be the climax of your punishment, and it's going to be very special. I know I'm going to enjoy it, anyway!" She laughed. "However, I couldn't let you go tonight without some form of punishment. The pink panties seem to work well, but this.." she reached down and stroked my quivering erection, " this seems even better. I bet you'd like to rub it now, wouldn't you? I can feel it twitching. Here you are, all excited, with your Mistress bare butt only inches in front of your face, and there's nothing you can do, is there?" she chuckled gleefully. I groaned with frustration, and she laughed even louder. "Now Sonny boy, I did promise you were going to be teased and humiliated, as well as spanked, didn't I?" "Y-yes Mistress" I said wretchedly. Mistress beamed at me. "Well, what could be better than this then. I'm going to leave you all hot and aroused and desperate to come! What's more, I'm going to go next door and rub my hot, juicy pussy until I have a super orgasm! Just think about that!" I groaned, and Mistress dissolved into fits of giggles. Drops of pre-cum oozed from my prick as I imagined her naked on her bed, leisurely masturbating over thoughts of my freshly spanked butt. Without warning, she reached over and squeezed my cock hard, making me wince. "By the way, Sonny boy," she said coolly, "if I find any traces of nasty boy cum on you or the bed tomorrow, I shall take a switch to your bare balls. So don't get carried away, now!" She went next door to her room, and soon I heard the sounds of her moaning. She was right that I was in danger of just coming without any stimulation, I was so aroused. However, the thought of getting switched across my balls was just too frightful, so I writhed on the bed, bending my boyish pintle against the firm mattress 'til it hurt, trying to think about mundane things, anything to avoid an orgasm. Finally, Mistress's moaning ceased, and I was able to relax a little. My cock was still hard, but the worst danger had passed. It took a long time to get to sleep, but I finally managed it. My day of reckoning had arrived. After dinner, Mistress took me upstairs and gave me a shower. She then gave me a new pair of panties to put on. They were like french panties, but cut much higher up the leg, so that part of my buttocks were exposed, and made of translucent white nylon. Once I had put them on, Mistress handcuffed me to my bed as if I was going to sleep. To my surprise, she then stripped off in front of me! My cock swelled inside my panties, tenting them obscenely. Mistress laughed and stroked the bulge, sending shivers through me. "We're going to have some company in a little while." she said. "Just a few friends coming round to help me with your punishment. I think this evening's going to be a great deal of fun! I'm going to go and change before they arrive. I'll come and get you when they're here. You just lie there and think about how humiliating it's going to be, and how sore your bottom will be when you go to bed tonight!" With that she left, and I lay on the bed in a daze of arousal, fear and anticipation. Before long I heard the doorbell go, and female voices in the hallway. A few minutes later it rang again, and there were more voices. After a while, I heard Mistress's footsteps on the stairs, and she came into my room. She was wearing the exact same outfit she wore the day I tore her skirt in public, and looked simply stunning. I stared open mouthed at her, and she grinned at me as she unfastened my cuffs. "Come on, Sonny boy. Time to meet your guests! I think you'll recognize everyone. When we go in, I want you to go up to each person, say hello, and tell them you hope they will enjoy spanking you this evening. Understand?" "Y-yes Mistress." I stammered nervously. Mistress chuckled and stepped back, her eyes never leaving mine. "There's one more thing you should know, Sonny boy." she chuckled. "Mistress isn't wearing any panties!" She hitched up her skirt briefly, flashing her sexy pussy at me, then lowered it again. My cock hardened instantly, and Mistress laughed. "Mmmm, that does make a nice bulge in your panties!" she giggled. "You just keep thinking about how much I enjoy punishing you!" With that, she took me by the arm and led me downstairs to the dining room. My Mistress' Skirt As we entered, I noticed that the dining table had been pushed against the wall, leaving a large space in the middle of the room. The chairs were arranged along the sides of the room, and were occupied by four women. I gasped in shock as I saw who they were! Sitting there were Lady Pamela and Lady Denise, from the shoe shop where all this had started, our next door neighbor Lady Christina, and my form teacher at school, Lady Irena! I stood there stunned and blushing furiously, as they all looked at me and laughed. My embarrassment increased as I realized my cock was still hard and very prominent, and showed no signs of going down! I realized with a shock that this must have been the purpose of Mistress's little exhibition upstairs, but the knowledge only added to my arousal. "Oh my!" said Lady Irena. "He does look smart, doesn't he!" "I see the little panty slut has excited himself." remarked Lady Pamela, and my face went crimson with embarrassment. Remembering Mistress's instructions, I went up to Lady Denise, who was closest to me. "H-hello, Lady Denise. I-I hope you enjoy p-punishing me this evening." I stuttered. Lady Denise smiled. "Oh, I'm sure I will Sonny boy." she said huskily. "I do so enjoy spanking naughty boys like you in my shop, and this promises to be even more fun!" She reached out and stroked my cock. "Looks like you think so too!" she purred, and they all laughed as I moved to stand in front of Lady Pamela. "Hello Lady Pamela. I hope y-you enjoy punishing me this evening." Lady Pamela grinned viciously at me. "Oh don't worry, Sonny boy, I'm going to have the time of my life! I'm really going to enjoy getting to your bottom! You're just a filthy little panty slut and I can't wait to hear you squeal!" I trembled at her words, and then moved on. Lady Irena was a new teacher at school, and was already very popular. She was a nice woman, and was also extremely attractive. Several of the boys had a crush on her, including me. Mistress Mona had quickly deduced this from the way I had talked about her so much, and had given me a few words of advice on how all boys had crushes, but not to let it get out of hand. I had been grateful to her at the time, but now I was terrified that she had used the knowledge against me. My fears were soon realized! "Hello, L-Lady Irena. I hope you enjoy punishing me this evening." "Thank you Sonny boy. Your Mistress told me what a crush you had on me and now I have the evidence before me!" she chuckled, staring pointedly at the bulge in my knickers. "So I'm sure you're going to enjoy stripping for me as much as I'm going to enjoy spanking you! It's so rare for a teacher nowadays to get the opportunity to punish one of her students properly. I'm so looking forward to it!," She threw her head back and laughed out loud. "H-hello Lady Christina. I-I hope y-you enjoy p-punishing me this evening." I stammered, now extremely nervous. Lady Christina represented my darkest secret, and if Mistress had told Lady Irena about my crush, I knew she must have told Lady Christina about what had happened! My cock throbbed urgently at the thought. "Well hello Sonny boy! " said Lady Christina brightly, her eyes gleaming. "Your Mistress tells me she had to strap you not long ago for spying on my sunbathing, is that right?" "Y-yes Lady Christina, I'm sorry!" I blurted. A couple of weeks ago, Lady Christina had been nude sunbathing in her garden. She had a warm honey-colored tan, with sharply contrasting bikini tanlines showing off her beautiful butt to perfection. Mistress caught me jacking off and staring at her. She told me off for not respecting Lady Christina's privacy, and gave me a good bare-bottomed strapping to drive the lesson home. "Well, I know your mother punished you for it, but I'm looking forward to being able to add some punishment of my own! I'm sure I can make your nasty little pintle behave properly!" She laughed loudly as I blushed crimson, and the others joined in. Mistress then beckoned me over to the table and made me bend over it. She then tied my wrists and ankles, so I was bound securely and unable to move. My bottom stuck out obscenely, my legs slightly parted so as to put me in the perfect punishment position. She then stepped back and pulled my panties down, at which a chorus of whoops and laughs erupted behind me! "Look at me Sonny boy!" commanded Mistress, and I turned my head to one side. My blood ran cold as I saw that Mistress was holding a long, thin wicked-looking cane! "Isn't she a beauty?" chuckled Mistress. "I know you're just going to love it!" She moved out of sight, but continued to speak. "Right ladies, four strokes each. Denise, you go first." I heard movement behind me as Lady Denise stood up and took up position behind me. She swung the cane experimentally a few times, and I winced and trembled as I heard it swish through the air. I heard Lady Denise giggle quietly, and then she swung the cane through the air and brought it down across my buttocks. ssssTHWACK! I yelled loudly as the cane bit into my already sensitive buttocks, leaving a white hot line of pain. sssTHWACK! The second stroke landed higher up my bottom, and I cried out again. sssTHWACK! sssTHWACK! The next two came quickly, but both were slightly misplaced and were less painful, although I still grunted at the impact. I heard Lady Denise return to her seat, as the others applauded her efforts politely. I lay on the table, breathing hard. The cane had stung badly, but it had not been too bad. However, I was aware that Lady Denise was the youngest there, and the most inexperienced. I suspected that Lady Pamela would be next and I was dreading that! I was surprised to notice that my cock was still half hard, and the applause that Lady Denise received had served only to make it start to stiffen again. This did not go unnoticed by Lady Pamela, as she stepped up to take her turn. "Oh for God's sake, Denise! You didn't even remove his erection for him!" she exclaimed loudly. I blushed as the others laughed at her words, and then stiffened in shock as she reached down and took my cock in her hand. First she lightly ticked the tip, then she stroked it steadily, firmly, and in no time at all I was rock hard and quivering. "There. Now I'll show you ladies how to get it from rock hard to completely soft!" she declared viciously. She stepped back and swung the cane. sssTHWACK! "Aaaiiiieee!" I screamed loudly, my eyes watering as the cane tore savagely into my bottom. Lady Pamela had landed her stroke perfectly on the join between buttock and thigh, and the pain was intense. I couldn't believe how hard that stroke was. Lady Pamela was clearly an expert with the cane! sssTHWACK! The cane landed very close to the first stroke, and I yelled and thrashed against my bonds. sssTHWACK! Another vicious stroke to the same place, and I screamed. The agony was intense! Tears poured down my cheeks and I moaned as Lady Pamela paused to admire her handiwork. sssTHWACK! The last stroke landed at a slight angle, crossing all the previous welts Lady Pamela had left! I yelled at the top of my lungs, jerking so hard I felt the table move, and for an instant I feared I was going to pee on the table. The effect of the cane landing so hard on those fresh welts was horrible. It was like someone holding a red hot cigar to my bottom! As I slumped onto the table sobbing loudly, Lady Pamela stepped up and reached between my legs. "See?" she said, flicking my now flaccid and shrunken cock contemptuously. "Completely soft, just like I promised." She sat down, and there was a thunderous round of applause, and many compliments on her technique. After this, I was a allowed a slight rest. I lay on the table trying to regain some control, and listening to the surreal sound of Mistress pouring cocktails for her guests like it was a wild party. Once I had settled down, Lady Irena stepped forward to take her turn. "Well, that's a hard act to follow!" she chuckled, "but I think I have the solution." sssTHWACK! The cane hissed through the air and bit into my left thigh, the tip curving cruelly to bite into the tender right thigh. I howled in pain and surprise and danced against the table. "Nice shot!" I heard Lady Pamela remark appreciatively. sssTHWACK! The second blow repeated the trick and had me jumping and twisting against the table. Then there was a short pause and I heard Lady Irena moving behind me. "Ahh, the advantages of being born ambidextrous!" she sighed. Just as I realized what this meant, the cane hissed through the air. sssTHWACK! It landed against my right thigh, giving it the same agonizing treatment to the left thigh. sssTHWACK! The last stroke bit into my thigh. I danced wildly against the table sobbing in pain. Lady Irena sat down and was applauded. "Excellent!" cried Lady Pamela. "It's so nice to meet another so skilled as you!" Lady Irena said nothing, but I could easily imagine the smile on her face. After a short pause, I heard Lady Christina stepping up to take her turn. "Well, this is a fine kettle of fish!" she said. "I'm going to have one helluva time trying to find a fresh spot to swipe." I trembled at her words. I heard her shift, and then sssTHWACK!, the cane was brought up between my legs with a sharp upwards flick. It landed right on the tip of my penis. Although I was still soft, and it wasn't too painful, I still yelled loudly. In my current state, the slightest touch was torture. sssTHWACK! sssTHWACK! Two more strokes landed, very near to each other on the center of my shaft. I screamed and sobbed, writhing against the hard surface of the table. "You are being a bit charitable, aren't you?" I heard Lady Pamela say, and I sobbed loudly at her cruelty. At that moment, unbeleiveably I began to get hard again. "I just like punishing young boys ," replied Lady Christina. "It's your fault for being so selfish earlier!" Everyone laughed, while I lay sobbing on the table, grateful for the brief respite. sssTHWACK! I screamed and bucked. Lady Christina's last stroke landed vertically, in the crack, against the boy hole, bringing me to full erection in the process! I slumped down on the table, sobbing hysterically. My bottom still burned furiously with the pain. Seeing the state I was in, they decided to give me another rest before Mistress Mona took her turn. More refreshments were poured, and I was dimly aware of conversation and laughter. I couldn't take in the words, though. I was only aware of the blazing pain in my buttocks. My sobbing slowly quieted, and I lay limp as a wet dishrag across the table. My arms and legs were aching from pulling against my bonds, and I felt totally wretched. To my intense relief, I was left alone for quite a while and was able to slowly recover my composure a little. All too soon, however, I felt Mistress's fingertip tickle my dick. "Are you ready now, Sonny boy?" she asked. "One last set and then it's all over!" She moved away without waiting for an answer and I heard her moving away. The conversation faded as they all waited for the final act to begin. To my surprise, I heard Mistress Mona leaving the room. The others were clearly puzzled as well, until she returned. Then I heard a soft murmur of appreciation, and Lady Denise's voice asking plaintively, "Just what the hell is that?" "A Bare Bottomed Bonus!" laughed my Mistress. "It's freshly peeled root ginger." explained Lady Pamela. "Very nice! It dissuades him from wanting to clench his behind. You'll see what I mean in a minute." I heard Mistress Mona coming over to me and felt her hands on my bottom. Suddenly something slippery was being pushed into my boy hole! It slid a short way in and then stopped, but almost instantly my hole began to itch and burn maddeningly. I twitched and danced against the table, moaning softly, and I heard the women behind me giggling. "It burns his little asshole." I heard Lady Pamela smirk. Then they fell quiet, as I sensed Mistress Mona taking her position. "Now like all the best spankings," Mistress Mona proclaimed, "this one is going to end with six stinging strokes, each just as hard as I can possibly make them!" I whimpered as I waited for her to strike, wondering if I could take it. sssTHWACK! The cane fell diagonally against the center of my bottom, bisecting across the previous weals. I yelled and fresh tears filled my eyes. sssTHWACK! Another one fell in much the same place, and I screamed and twisted against my bonds. Every time I tried to clench my bottom cheeks together, the ginger would burn my boyhole and force my bottoms to open obscenely, as if begging for the next stroke, which my Mistress was all too happy to provide. I sobbed steadily. sssTHWACK! The cane caught me on the backs of my thighs. I squealed and tugged but to no avail. sssTHWACK! Both thighs again. Since Mistress was not ambidextrous, it thankfully missed the previous weals, but not by much! Added to the way the ginger was making my boyish anus burn and itch, it was enough to have me writhing and jerking against the table, much to the delight of my audience. sssTHWACK! The next stroke landed right on the crease where bottom meets thigh, right where Lady Pamela had applied all her cruel strokes! I screamed loudly, bucking and thrashing against the table. "OK Sonny boy, final stroke. This is going exactly where the last one went, so get ready for it!" "Oh no! Pleease M-Mistress! Please no more!" sssTHWACK! "Aaaaiiihhhhh!" My pleas fell upon deaf ears as the cane slashed down and I screamed. The cane stroke slashed into my left thigh, sending the tip, which bent upon impact, whistling into my throbbing erection. The pain exploded in my penis and butt at the same time, tearing me in two. But at last it was over. I slumped down on the table, sobbing loudly, as everyone applauded Mistress's performance. Soon afterwards, I felt hands at my wrists and ankles, as everyone helped to release me as quickly as possible. I also felt the ginger being unceremoniously yanked from my bottom. I could barely stand after my ordeal, and Mistress and Lady Pamela each put one of my arms over their shoulders and helped me to my feet. As they helped me to move, Lady Pamela stood up and came to stand in front of me. I looked up at her nervously. She was smiling, and for once there was real tenderness in her face. "Sonny boy, I just want you to know that I'm very impressed by you. You took your punishment bravely. It was wonderful." With that, she leant forward and kissed me warmly on the mouth! In spite of the pain, I felt my limp cock twitch slightly. Then Mistress Mona and Lady Pamela took me upstairs. They laid me down on Mistress's bed, and Mistress rubbed cream into my bottom. She also placed ice packs on my behind. Then they left me alone and went downstairs. I lay on the bed, still crying occasionally, before finally falling asleep. The strain had overwhelmed me, and my mind took the kindest option available and just shut down. I was awakened by the bedside lamp being turned on. I rolled over onto my side and saw Mistress kneeling next to me. "How are you feeling?" she asked gently. "Effin' sore!" I said, with feeling. Mistress smiled. "You did very well down there." she nearly whispered. "Everyone thought so, not just Lady Pamela, they were all very impressed, and so was I." She stood up and began to undress. I watched her slowly take off her skirt. Underneath she was naked but for stockings and suspender belt, and my cock hardened rapidly. She quickly removed these and then climbed onto the bed next to me. "Lie on your back, Sonny." she said. Nervously I obeyed, wincing as my buttocks rubbed against the sheet. My eyes watered as the weight of my body started my bottom throbbing again. I looked over at Mistress pleadingly, but she just smiled. Then, to my surprise, she leant over and took hold of my still hard cock and began to stroke it. "You know Sonny boy, when we started this, I just wanted to get back at you for making me feel so embarrassed and humiliated. I was determined to make you feel just as humiliated." Her fingers continued their gentle fondling of my cock, which was now fully hard. I ceased to be so aware of the pain in my bottom as I focused on the seductive lilt of her voice, and the feelings in my balls. "As we went on, however, I realized that I was starting to really like humiliating and punishing you. I know that's pretty terrible of me, but it's true. It made me really hot. I also realized that you were enjoying at least some of it as well. You were, weren't you?" "Not the spankings!" I cried. "They really hurt!" "I know, darling. " said Mistress. "Don't worry, you won't have to take another spanking like today's ever again, I promise. But you really did deserve a couple of good spankings for what you did, though, didn't you?" "Y-yes Mistress." I said quietly. She was right, of course. It had been pretty bad of me, and I did deserve to be punished. Mistress leant closer to me, her breast brushing erotically against my arm. "But you did like being humiliated, didn't you? You got hard every time." "Y-yes Mistress," I admitted, blushing furiously. "I suppose I did like that. It felt really strange, but it did turn me on." Mistress smiled, and her fingers quickened slightly on my throbbing erection. "I know." she chuckled. "That's why I've decided we're going to continue some rituals, even though your punishment for ruining my skirt is over." My cock throbbed at this, and Mistress giggled and began to stroke me steadily. "For a start, you're going to keep wearing girls' panties around the house, and nothing else! Lady Pamela says she has a friend who runs a lingerie shop in town, and who will be delighted to help! When you've healed properly, we're going to go down there and get you some pretty little panties of your very own!" I moaned softly as my cock began to pulse, and my mind whirled with the thought of our impending shopping trip. "Speaking of Lady Pamela," she continued, "Pam tells me that she needs someone to work part-time to help out in the stockroom. You did say you wanted a summer job, so I've agreed that you will spend one and a half days a week at her shop. Since the work is all in the storeroom, you'll be able to do it wearing just your girlish panties. Of course, I've told Lady Pamela that if you misbehave in any way, she has my permission to spank you for it!" A chill ran down my spine at this, and yet somehow it aroused me as well. "It seems that Lady Christina needs some help as well. Her garden is a little big for her to manage, so I said you'd help out Saturday afternoons. You'll be allowed to dress normally, of course, but she will still spank you if you don't work hard enough." My cock was throbbing now, as Mistress's hand worked up and down it briskly. I just lay there, panting quietly as Mistress laid out this incredible program. "Of course, we don't want these jobs to get in the way of your education, so Lady Irena has kindly agreed to spend half a day with you to keep your studies up to par. Although judging by the way she was tickling her pussy while you got your caning, I'd say you might get some pretty severe lessons! I've never seen such a display!" I moaned loudly, and my balls tightened. Images of Lady Irena naked before me filled my head. Mistress grinned and quickened the pace of her hand, stroking me fast now. "And then there's ME, Sonny boy. Mistress is going to keep an strict eye on you from now on. You'll be spending all your time at home in just panties, and if I hear any complaints about you, you'll be bending over for a severe strapping or a nice, painful caning!" Mistress was masturbating me hard now, and I felt my orgasm approaching rapidly. "Mistress likes spanking her little panty boy! Mistress knows that bad little panty boys need lots of spankings on their bare bottoms! Plus it makes Mistress pussy really hot. Whenever Mistress feels a little horn-ay, she's going to put panty boy over a chair and spank him! She's going to spank him until the pussy juice is running down her thighs, and her bad boy is really sorry!" I came hard, moaning loudly as six hard jolts of semen squirted from my cock and splashed over my Mistress and myself. I could hear Mistress giggling as she continued to pump me, but it seemed like miles away. I was lost in my reverie, and in the thought of all the humiliations and spankings that were yet to come.