by Kyoko Church
I closed my eyes and thought deeply about how far all this would go. I opened my eyes once more when I felt the maid’s hands on my balls.
‘I am going to lather you up a little,’ she said, half-whispering. ‘Please don’t move.’
I saw the straight-edged razor in her hand and knew I dare not move. Nonchalantly, she coated my testicles with a thick lather of shaving cream. It was quite cold to the touch and I felt my cock shrivel slightly at the first touch. She then lathered the area around the base of my cock.
I closed my eyes again at the first touch of the blade to my privates. I was leaving my most worldly possessions in what I hoped were the capable hands of a young maid.
I felt the blade contact the sensitive surface of the testicles. I clenched my hands tightly.
‘Relax, Mr Morton, I have done this many times before.’
Somehow I assumed she had. As she removed the hairs around my balls, she applied more lather and soothingly warm water as needed to accomplish her mission. The rest of my pubic hairs were next.
I was almost petrified, but kept perfectly still and came through the procedure unscathed.
Jennifer dried me with a soft cotton towel. Her touch urged my manhood slightly, but I maintained my dignity long enough for her to help me from the table.
‘Come with me, please,’ she said politely.
‘My clothes?’
‘You won’t be needing them where you are going, Mr Morton. Not for the rest of the evening anyway.’
Totally naked, my cock swinging freely, I walked next to Jennifer to a room at the far end of the corridor. She used a key to open the door and held it for me to enter. There was only one item of furniture in the room, if you could call it furniture: a black sawhorse with a thick red velvet pad on top of the crossbar. And leather cuffs at the bottom of each of the four legs.
‘You will lean over the sawhorse, Mr Morton,’ Jennifer said, ‘your tummy on top of the cushion.’
With more than a little trepidation I moved across the thick carpet to the ominous-looking contraption that stood in the centre of the room. Hardly had I bent over it when the maid moved to kneel behind me.
Quickly she pulled my left leg to the side, affixed the leather cuff around it and tightened it just enough to cause slight discomfort. She moved to the other side and did the same with the right leg. I could only imagine the view she was getting with my legs spread wide and my genitals swinging in the breeze. Before I knew it, my wrists were shackled to the front of the sawhorse.
For good measure, she drew a strap from one end of the sawhorse to the other, pulling it tightly over my back, ensuring that movement was all but impossible.
Before she left, she placed a blindfold over my eyes so I was left in almost total darkness.
Then Jennifer was gone, leaving me naked and alone.
Miranda deliberately left me naked and alone like this to ponder my fate. I knew I was about to be whipped for the first time in my life, but I had no idea what else might be in store for me.
The minutes passed.
I was getting worried here.
The door opened.
I had no idea if it was Jennifer or Miranda who moved behind me. Whoever it was moved so quietly I could hardly hear movement. I strained to listen in the darkness.
Then, without warning, I heard a slight whistling sound, followed by a loud crack of leather against flesh.
Her leather.
My flesh.
My cry reverberated throughout the room.
‘My dear Mr Morton,’ came the voice through the pain.
It was Miranda. Wickedly beautiful Miranda who was also wickedly painful Miranda.
‘If you are going to be a baby about this we are going to have to gag you. Please try to be a bit more quiet.’
I braced myself for the next stroke. Instead, I felt a few light taps from the tip of whatever she was using. Then she reached back. I braced again, clenching my ass cheeks tightly.
‘The more you clench like that, Mr Morton, the more it will hurt. You will need to learn to relax and accept.’
Easy for her to say.
And the second I relaxed she whaled into me with a second stroke that must have left a huge gash. It didn’t, of course, but it sure felt like it. My ass felt like it was on fire from just two applications of her merciless whip.
‘He is taking it better than I thought, but he has so much to learn,’ said Miranda.
‘He is streaking nicely already,’ said a second voice.
Maid Jennifer.
‘His balls look very nice. You did a fine job, Jennifer.’
‘Thank you, ma’am.’
‘Would you be kind enough to tease them for me?’
‘Gladly, ma’am.’
A small hand on my newly shaved testicles, weighing the sack in her palm. Gently massaging them. Pushing them and watching them sway to and fro between my well-spread legs. Suddenly she grabbed them, squeezing them tightly, and pulled them sharply down. I winced, then cried out again from the pain. This was more than ‘teasing’, at least in my book. When she cruelly twisted my beleaguered sack while applying way too much pressure, I cried out even more loudly than I had the first time.
‘He didn’t listen very well about making noise, did he?’ asked an obviously annoyed Miranda.
‘No, ma’am, he didn’t.’
‘A penis gag might help,’ said Miranda.
‘I’ll get one, ma’am.’
Jennifer stood in front of me and shoved a long, rubbery penis-like device into my mouth, over my tongue. She quickly tied it around the back of my head. It was not long enough to force any gag reflexes in my throat, but I knew it would certainly hold back any further screams.
‘Good girl. Let’s see how well it works. You may tease him some more.’
Jennifer moved behind me again and grasped my still aching balls. This time there was no preliminary gentleness. She grasped them as tightly as she could and seemed to take delight in watching my head shake back and forth and listening to the muffled cries over the penis gag.
‘Much better,’ said Miranda, ‘the noise was getting annoying.’
‘But he isn’t taking well to the pain, ma’am,’ said Jennifer as she twisted the sack mercilessly.
‘He will learn … in time. Try teasing his cock a bit.’
Jennifer released her grasp on my testicles and quickly found my woefully flaccid cock. If her grip on my balls was painful, her locked hand around my manhood sent me through the roof in pain. She pulled it down so hard I felt like she was going to rip it from my body. Sweat gushed from my forehead. The penis gag drowned out my screams, leaving incoherent moans and unintelligible noises as the only sounds filling the room.
‘Enough,’ Miranda said and Jennifer released her grip on my manhood. I never knew such relief in my life. I heard Miranda move in front of me. I couldn’t see her behind my blindfold, but her familiar perfume wafted to my nostrils. She moved her index finger to my chin and raised my head.
‘You are actually doing better than expected, Mr Morton. There are always rewards for pain, but we are not done with your little initiation. I need to talk with you first.’
I felt Miranda’s hand behind my head, undoing the knot, pulling the penis gag out. My mouth was terribly dry. ‘Thank you … Mistress.’
‘Listen very carefully, Mr Morton. You are free to get up and leave right now. No questions asked. But if you go you will never see me again. If you choose to stay, you will be invited back at times I choose for you. Sometimes the pain will be unbearable. At other times you will be teased to the point of ejaculation, but you may not come without my express permission. If you do, you shall be punished severely.’
She pulled the blindfold from my eyes and let it rest on my forehead. At first the light in the room blinded me, but, as my eyes became accustomed to the light, I gazed upon her beautiful face. I was under her spell. I would endure anything just to be with her.
‘Do y
ou wish to leave, Mr Morton?’
‘I hurt so much, Miranda. My ass, my balls, my cock …’
‘It is nothing compared to what you can expect each time you return.’
I wondered how I could take even more pain, but out of love I calmly said, ‘I accept your desires.’
She smiled. I had pleased her, obviously, and in my heart I was happy to have done so. I looked further down her body.
She knelt on one leg, and in doing so offered me an inviting glimpse all the way up her short black skirt. She was not wearing panties, and her pussy was totally shaved. Her vulva was puffy with a prominent clitoral hood. I thought I saw some moisture inside the delightful slit.
She caught me staring at her goodies and, grasping my hair, pulled my head up sharply so I was now staring into her pretty blue eyes.
‘Did you enjoy the view you just had, Mr Morton?’
‘Yes, ma’am,’ I admitted.
‘From this moment on, you will never gaze upon any part of my body, even my face, without permission. In my presence, you must always look down at the floor, head bowed, in respect of your Mistress.’
I closed my eyes. ‘I understand.’
‘The penalty for looking at me is hardly worth the risk, Mr Morton.’
I nodded in agreement.
‘Now you will pay for looking up my skirt. Shame on you! Get me the cat, Jennifer.’
I had no idea what Miranda meant by a cat, but I would soon find out. With my eyes still closed, I sensed her rising and moving behind me once more. Jennifer returned from the side of the room with the cat in her hand.
‘Have him kiss it, Jennifer. You may open your eyes, Mr Morton.’
It was Jennifer’s turn to kneel in front of me. In the palms of her hands she was holding a wicked-looking multi-stranded black whip. Each of the leather tails of the whip was about a foot long and perhaps a quarter-inch thick. The handle was made of braided leather. I knew this mean-looking sucker would hurt like hell. She held the whip to my lips and I kissed the strands that would soon be the cause of pain.
She arose and handed the cat to Miranda.
‘Why are you getting whipped, Mr Morton?
I said, ‘Because … because I looked up your skirt, Mistress.’
I thought I heard a faint ‘whoosh’ in the air, then the loud crack of the twelve leather strands meeting my naked ass. Without the penis gag to hold it back, my scream echoed through the room. In time Miranda would teach me to accept a whipping without screaming, but this time I think she wanted the audio affects.
‘Are you ever going to look at me, any part of me, without permission?’
‘No, ma’am,’ I replied as best as I could, for I had quite a pain in my ass.
The whip swished again with an even louder crack, snapping my head back. I cried out. Hardly pausing, she gave me another one. And yet another. I sucked in my breath and let out a horrendous scream.
My backside was on fire from the three quickly delivered strokes.
My whole body bucked against the cuffs and chains that held my arms and legs.
‘That was merely a surface scratch, Mr Morton. If you ever disobey a rule again, you can forget about sitting down normally for a week. Do you understand?’
I took a deep breath before I could answer. ‘Yes, Mistress.’
‘Let him loose, Jennifer.’
Jennifer undid each of the cuffs and the strap over my waist, and then helped me rise from the sawhorse.
My body ached from its awkward position. I stood on rubbery legs until Miranda told me to turn and kneel in front of her.
I kept my head lowered, staring at the carpet, as I knelt submissively in front of her.
‘Part of your training, Mr Morton, is to show an appreciation of women. All women. Not just me, though you will come to love me more than anyone you have ever known. To appreciate a woman, you must know what it is like to be one. When I was in high school, I was raped, anally, by a teacher I thought I could trust. I was only fifteen. The shame and the pain were quite unbearable. You will come to know how I felt that day.’
I nodded. ‘Yes, ma’am.’
‘Every woman endures a monthly cycle, from puberty to her fifties. It is not pleasant, not at all, but it is part of life. I can’t even begin to help you understand its unpleasantness, but I can help you gain a little appreciation for it. Turn around and get on your hands and knees.’
I had no idea what she was planning to do, but I knew not to hesitate in following any of her commands. I knelt, head lowered, eyes closed, my naked ass and newly shaved balls only a foot or so from her head.
‘Get me a tampon, Jennifer.’
A tampon? I realised what was in store for me.
Jennifer left, returned in seconds and handed the white cloth cylinder with its familiar string to Miranda.
‘Open him for me.’
Jennifer straddled my hips and pried my ass cheeks apart with her hands, revealing my anus to both women. I had never felt so exposed in my life.
‘Women have to put this damn thing inside them so many times in their lives. It is never pleasant, Mr Morton, as you shall learn. And you will never know all the other discomforts associated with it. Actually, I prefer a pad, and I will even allow you to change it for me when the time comes. But the tampon will give you a better feel for a woman’s plight.’
‘I am having my period now, ma’am,’ said Jennifer.
‘And do you need changing?’
‘I believe so.’
‘Good. A little practice never hurts. But first, let’s feminise him a bit.’ I felt the somewhat hard cloth cylinder touch the centre of my anus. I braced myself. ‘Stretch him wider, Jennifer, the poor baby is still a virgin even to this small a thing.’
I felt my anus being opened wide as Miranda began moving the tampon into me. There was no pain involved, but the humiliation was unbelievable. Slowly but surely several inches of the tube was fully ensconced. Jennifer closed my anus around the string that hung outside my ass. Miranda tugged lightly on the string to add to my embarrassment.
‘Do you feel that inside you, Mr Morton?’
‘Yes, ma’am,’ I softly replied.
‘You may take it out tomorrow morning. But not before. Understood?’
‘Yes, ma’am.’
‘Good. Now you can bestow a favour on Jennifer. Go get a pad, dear.’
Jennifer left the room and returned moments later with a white feminine pad in her hand. I couldn’t believe what I was about to be expected to do.
‘Kneel in front of her, Mr Morton. You may open your eyes so you can see what you are doing.’
I knelt in front of the young maid, my heart racing.
‘Raise your skirt, Jennifer.’
Right in front of my face, Jennifer blithely lifted her black skirt all the way to her waist, revealing a pair of pretty white shiny rayon panties.
The bulge in the panty crotch was obvious.
‘Lower her panties, Mr Morton.’
I slowly lowered the dainty undies to her thighs. Jennifer’s pubic hair was pure black. The triangular curls were thick. I felt a familiar stirring in my loins as I looked at the forest in front of my eyes. I started to raise the panties, but Miranda interrupted me.
‘Kiss it first, Mr Morton. To show your appreciation of womanhood.’
I leaned forward until my nose grazed against the delightful pubic curls. Jennifer put her hand on my head, holding it in place, and opened her legs slightly, in obvious invitation for me to kiss her pussy.
‘Very good, Mr Morton. Let’s get her back to normal.’
I pulled the panties back up after getting one last look at Jennifer’s pretty pussy. She lowered her skirt and I dutifully lowered my eyes, still kneeling in front of her.
‘He will make a wonderful student,’ Miranda said.
‘I do believe so, ma’am,’ Jennifer agreed.
‘He deserves a reward.’
‘He has had a difficult night, ma’am.�
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‘Turn around, Mr Morton.’
I turned on my knees facing Miranda, head still lowered.
‘Get me a chair, Jennifer.’
Jennifer pulled a leather armchair from the side of the room and moved it behind Miranda. Miranda sat in it, facing me.
‘You may look at me, Mr Morton.’
I opened my eyes.
Miranda was right in front of me, seated, her gorgeous legs tightly closed. I felt the presence of the tampon in my ass, but I was slowly getting accustomed to the odd feeling.
‘You enjoyed looking up my skirt earlier?’
‘Yes, ma’am,’ I admitted.
‘And what you saw there pleased you?’
‘Very much so, ma’am.’
‘If you were to see it again, would you have a desire to give pleasure to it?’
She was teasing me mercilessly, but just the thought of being asked to pleasure her hairless pussy was suddenly driving me wild.
‘I would indeed, ma’am,’ I said.
She opened her legs ever so slightly and leaned forward.
‘If you don’t make me come, Mr Morton, I will beat your worthless ass raw.’
I needed no incentive. If she were to allow me a few moments between her legs I would spend it wisely. She opened her legs just wide enough to afford me a view of the creamy lips of her pussy.
My heart was beating wildly.
My Mistress was showing me her treasure.
She pulled her skirt up, opened her legs as wide as she could and rested the backs of her knees on the arms of the chair. Her slit was opened enough to reveal a good deal of pink, very moist tissue. The sight before me was perhaps the ninth wonder of the world. Her cunt was certainly out of this world.
‘Go for it, Mr Morton.’
I didn’t care that Jennifer was behind me, watching. I leaned forward, between the widespread legs, and began kissing the puffy pussy lips. Miranda moaned at the first touch of my lips. Her womanly smell wafted through my nostrils.
Using several fingers of each hand, I boldly pried the lips apart. The slit was filled with clear and copious moisture. It was mine for the taking. With the flat of my tongue I licked her from her vagina to her clit, gathering as much moisture as I could. Her taste was exquisite. She moaned again, this time more loudly.