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.