Category: story

It was very sad and ironic. I had just turned 18 and was due to be released from the orphanage at the end of the school term. But then this had to happen.

I entered the office of Mrs. Boxworth, the Headmistress of the orphanage, with trepidation. She sat at her desk, wearing a high-necked white blouse and a black skirt that reached to her ankles, not quite covering the high-top black shoes. The blouse swelled in front, asserting the presence of her magnificent breasts that was famous among the boys of the school, almost as famous as the severity of her punishments. I handed her the note I was carrying from my classroom teacher. She read it with arched eyebrows and a grim, determined smile.

“So, James, Miss Sullivan has sent you to me for ‘special’ discipline. You have been very, very wicked. Do you admit your offense?”

“Yes ma’am, Miss Sullivan . . . saw me.”

“And will you please describe your iniquity to me?”

“I … I was in the restroom … you know, touching myself.”

She drew in her breath sharply. “I see. James, that practice is not only disgusting and immoral, but more harmful than you can even know. I shall have to punish you very severely, for your own good.”

Mrs. Boxworth led me into a small adjoining room, and closed the heavy door behind us. In the center of the room was a straight-backed wooden chair, of curious design I had not seen before. A large U-shaped gap bit into the front edge of the seat, so that an occupant would be supported along his thighs and buttocks, but his crotch would hang suspended over the gap. A low stool stood in front of it. An assortment of whips, paddles, and rods of various shapes hung on one wall. I knew that I was in for a whipping, but the array of implements puzzled me: they all seemed too flimsy and light of weight to do much damage to a teenage boy’s buttocks. I began to have an ominous sense of foreboding, without understanding why. “What … what are you going to do to me, Mrs. Boxworth?” “This is your first time to receive ‘special’ discipline, isn’t it, James. Of course, you are to be spanked, but I think that you will find that it far exceeds your expectations. Now remove your britches and underwear, please.”

School spankings were always administered on bare flesh, and I was not surprised at her order. I dropped my trousers and stepped out of them, standing shyly before her, naked from the waist down. I expected the usual “bend over and grab your ankles”; but instead, she set me in the half-bottomed chair and produced four short leather straps with which she bound my hands behind the back of the chair and my ankles to the chair legs. Finally she took a wooden rod that terminated at each end in a padded “Y” and placed it between my legs, looping leather thongs around each knee to keep it in place. The rod held my legs widely apart, and my naked genitals, dangling above the gap in the seat, were fully exposed to her. I was terribly anxious at these proceedings.

“What is that for? Please, Mrs. Boxworth, what are you going to do to me?”

She smiled, and explained, “The discipline you are about to receive is ‘special’ because it is applied to the ‘special’ parts of a young man, on which whipping is most effective. This brace will keep your legs separated, and you readily accessible.”

I could scarcely believe what she was implying. “What… what do you mean?”

“Don’t you understand yet? I mean, James, that you are to be whipped on your male organs.” I shuddered in horror. “No! Please! I couldn’t bear it!”

She looked at me with genuine sympathy, and gently stroked my cheek. “Then pray for courage.”

She withdrew from the wall a short rod that broadened at the end into a small paddle, rather like a miniature carpet beater. She drew the stool up in front of me and sat down. “Now James, we are ready to begin. I have secured you into this position so that you may watch the proceedings. I’m sure they will interest you greatly.”

She held her implement in front of my eyes. The small paddle on the end was cupped, rather like a soup ladle, and I shuddered to think for what purpose. “We call this the ‘slapper,’ and you will come to know it well; it will be your faithful friend in leading you from the paths of iniquity.”

She moved the slapper between my legs and brought it up slowly to my testicles, which fit neatly into the cup of the paddle, and hefted them in a gentle, almost caressing motion, “It is appropriate, is it not, to apply the discipline here, for these small Glands and their little appendix were the seat of your offense. Perhaps you did not know, as you were engaged in that loathsome act, that they can provide agony even beyond the wildest ecstasy?”

In spite of my fear, the gentle oscillation of my organs began to have an effect. My penis stretched and reared its head. “James! What is the meaning of this lewd insolence! Do you flaunt your carnality even in my face? Cease this disgusting display at once!” I pleaded, “But Mrs. Boxworth, I can’t help it when you… you’re making it …”

“What, do you blame me for your wantonness? I’ll make you sorry!” She lowered the rod and then with a flick of her wrist brought it up sharply between my legs. There was no doubt of her practiced skill as the paddle made precise impact with my testicles in a clearly audible “spat”. A searing pain gripped my viscera and I howled in misery.

“There, that’s better. Your member has lost its lascivious tension. What, are you in pain already? But we’re just beginning. Watch, James.” I tried to close my thighs to protect the vulnerable targets, but the brace kept them apart. She delivered three more quick slaps to my manhood, leaving me shivering in agony.

“Now, young man, as I have your attention, we will discuss the loathsome practice of self-abuse.” She began telling me of the evil and injury resulting from the practice of my vice, punctuating her words with regular assaults on my genital sacs. She applied the punishment in unhurried, measured strikes. Each began with a swift upward flick of her wrist, executed with a practiced skill, catching my dangling testicles precisely in the cup of the slapper with a quiet but devastating “spat”. As the resulting wave of pain and nausea washed over me, she held the slapper against my glands, cradling them in a soothing gesture. As the agony began to gradually subside, she slowly lowered her wrist and began again.

The torment I suffered was awful, worse than I could ever have imagined. Yet after some time, an unexplainable transformation began to take place. The pain was no less, but its very intensity confused and altered my senses. I felt a glowing heat at the core of my manhood, and the ache crossed over and became an indescribable sweetness. With each upward sweep of the slapper I began to welcome the blows on my tender bulbs, to relish being tied helplessly before this terrible but beautiful woman. I felt myself opening to her, spreading my legs and sliding my hips forward, offering my vulnerable maleness to her intimate caress. Through a haze I thought I saw just the trace of a smile on her lips.

Finally she ceased, put away the slapper, and allowed me to catch my breath. “You took that well, James, with humility and acceptance. Now we are ready for your next lesson. “Returning to the wall, she took down another implement, a wooden rod about a foot long to which a half-dozen short leather straps dangled from the end. She sat down and pointed the rod at my penis, a shriveled bud after the punishment of my glands.

“Now we shall address another part of your person, James. It is this small member that was the object of your lascivious mischief, was it not?”

“Are you going to . . . beat it like the other?”

“Yes, and no, James. We will whip it, certainly, but our purpose will be somewhat different as you shall presently see.”

She began flicking the whip back and forth across my flaccid penis. The punishment was surprisingly gentle, producing a light stinging that was almost pleasant, and certainly stimulating. My member, well trained by the regular but unsophisticated attentions of my own hand, began to respond the novel sensations. I recalled her earlier displeasure at this response and tried to suppress its insurrection by force of will, but it rose rebelliously in my lap.

“Well, James, it seems as if our work is not yet finished. Would you care to explain this manifestation?”

“I’m sorry! I know it’s wrong, but I can’t help it.” I knew better than to imply that it was her actions producing my insolent erection.

To my surprise, Mrs. Boxworth accepted my apology. “I know, James, I know. This organ is surely the seat of a young man’s temptations. It recognizes no master, but arises disobediently at its own impulse, and subordinates his will to its own voluptuous needs. See how it lewdly swells and puts itself forth to my whip, though I know you struggle against it.”

“I’m trying to make it .. . go down, but it won’t.” I was thoroughly off balance now by her unexpected sympathy. She continued to flick the whip across my erect penis from side to side, with increasing intensity. The whipping leather stung and turned my bobbing organ an extraordinary shade of red, but I found the sensations far from unpleasant.

“No, James, it is too strong for you alone. Do you feel how your member throbs and stings, James? The very Devil is in your flesh, and we must draw him out. We must whip the Devil out of your member, James, and make your organ humble and obedient once more. Will you work with me, James? Will you work to push the Devil out?”

I had no idea what she was talking about. I only knew I wanted the delicious stinging whip to continue nipping at my ruddy penis. I could feel myself becoming increasingly excited, and my member was emitting small clear droplets of arousal.

“You must bear down as I whip you, James, and press the Devil out. Your male organs are full of the Devil’s own spunk, and we must rid you of it. We’ve loosened it up in your glands with the slapper, and now I’m going to whip the semen out of your member.”

She maintained the maddening stinging rain on my penis, as I arched my hips in the chair to meet the whip. I could not believe this was happening, but I did not question it. The combination of pain and pleasure in my organ transported me into an almost unbearable rapture. “Please, whip it, whip the semen out. Oh! Mrs. Boxworth! I feel . . . Oh!”

“It’s starting, James, the Devil is starting to let go. Press him dear, bear down and push the Devil’s semen out.”

She continued to whip my penis from side to side as it throbbed and jerked, and the spasms of release began. But when the first pearly stream burst from the tip of my penis, she withheld the whip, and encouraged me only with words. “There, that’s it, James. Push for us. Push the Devil out of your member.”

I was wild with urgency as she stood idly aside, watching my penis ejaculating nakedly by itself. “Please, ma’am, please! Whip it! Whip it some more!” I begged, desperate for her touch.

“No, James, I’ve done my work. We must not tempt the Devil with further whipping, because he is making it feel too good right now. Just go ahead and squeeze inside yourself, and express all the semen for me.”

I thrashed in my bonds, trying desperately to find a way to rub my spasming penis on something. In an agony of frustration I watched my naked and lonely organ, untouched, spurt jet after jet of sperm into the empty air.

As I sat in the afterglow of release, covered in my own male juices, I thought that there was an end. But Mrs. Boxworth had one more surprise for me. Turning to the wall once more, she took down an ivory-handled knife, with a short blade that curved at the end into a cruel hook. The light gleamed on the blade, which I saw was sharpened on the inside of the curve.

She reached down and encircled the neck of my scrotum with thumb and forefinger, pinching my aching glands painfully. Her other hand took the knife and held the wicked curve of the blade against my sac, gently feeling for the precious testicles hidden but vulnerable inside. I shuddered at the touch of the cold steel on the wrinkled skin of my scrotum. “We have covered much ground today, James. I hope that you have learned enough. But if these arguments have not convinced you, there is one final measure I will take. Castration will surely put an end to your vicious habit. I would rather prune these fruit of carnality with the gelding blade and let you live you live as a neuter, than allow them to lead you to utter ruin.”

Her words filled me with indescribable terror. I had no doubt of her earnestness. “Please, please, Mrs. Boxworth, don’t! I promise to be good!”

She slid the razor-sharp knife over my scrotum, shaving off the hairs. A few flicks of the blade, and I was as smooth and hairless as a newborn babe. “There, that will serve as a reminder, when next you feel inclined to yield to your unnatural urges. Remember that if you are caught abusing your balls again, I shall take more than your pubic hairs.” I looked down at my pink, denuded scrotum and blushed in humiliation.

There was no more punishment. She released me, and told me to reflect carefully on what she had said. I left her office, walking slowly and awkwardly, wincing with every step at the lingering ache in my testicles, but as I walked and relived the incredible punishment in my mind, another feeling grew within my loins, welling up and consuming all else. I rushed into the hall lavatory and locked myself within the toilet. Beside myself with urgency that belied my recent release under her whip, I tore open my trousers and stroked my member to a furious, shuddering climax, spraying the walls of the toilet. with the jets of my semen. Finally at ease, I rearranged my clothing when the door of the toilet was opened and there stood Mrs. Boxworth with a smile and evil gleam in her eye. “Well I see I going to prune your fruit after all” and she grabbed my arm and starting dragging me down the hall. I started crying and screaming trying to get away, but she was too strong and shook me as I fought her, I was crying out “NO, NO, DON’T DO THIS TO ME!”

She merely laughed and said “You should have learned from the last lesson I taught you, now I am going to solve this problem permanently!” I screamed in terror and fell to the floor as I saw the half-bottomed chair and the four short leather straps with which she had used bind my hands behind the back of the chair and my ankles to the chair legs last time. I again jumped up and fought her with every fiber of my young body. I broke away and was headed to the door just when Miss Sullivan came though the door. I ran directly into her capturing arms.

Mrs. Boxworth said “hold him Alice” then Mrs. Boxworth grabbed my jacket shoulders pulling the jacket shoulders down pinning my arms behind me while Miss Sullivan grabbed my head and hair. I screamed, “Mrs. Boxworth is going to hurt me!, Help me!” Miss Sullivan laughed and said “Jane are you going help him to a better world?” Mrs. Boxworth laughed and said, “He can’t control his own urging and castration is the only solution for a young boy like him, Alice please help get him ready to receive the treatment.” Alice held me tight while Mrs. Boxworth started working on the belt of my trousers. I Felt her hands loosen the belt and I tried to break away but Miss Sullivan held me tight. Quickly Mrs. Boxworth found the button on my pants and unzipped me. dropping my pants to the floor. I screamed again and Miss Sullivan said, “Can’t you do something about his noise Jane?” Mrs. Boxworth said, ” Alice I have a gag I always use when pruning boy fruit, wait while I just reach behind me.” She took something off the hook behind the door that looking like a horse’s harness, saying to Miss Sullivan, “Alice hold his head up”. I tried to break away again but Miss Sullivan grabbed me hard saying to Mrs. Boxworth, “Jane you need to relax him” Mrs. Boxworth reached inside my underwear rapped her hand around my scrotum and squeezed tightly, I screamed and passed out.

When I came to I was aware that I was again tied in the open bottomed chair and I could not say a word because my head had a leather gag tied to my mouth covering all but my nose and eyes. I watched Mrs. Boxworth and Miss Sullivan sit on Mrs. Boxworth desk, they both were almost naked holding each other close and were kissing each other hard on the mouth. Mrs. Boxworth said to Miss Sullivan, ” I love to castrate young boys as cute and sweet as him. They are all too innocent and their nasty balls change them. “I know” said Miss Sullivan “I am really getting turned on with the thought of this castration myself. I really think almost all men and boys should be castrated except those we would keep for breeding purposes and those men should be castrated after 30 years of age, so they don’t father any retards” Mrs. Boxworth nodded and said, “I have to agree with you, Alice most men think with their balls instead of their head and most of the problems come from men”. She then took Miss Sullivan to her and kissed her full on the mouth while caressing the younger woman’s breasts. Miss Sullivan moaned, and moved her hands to the larger breasts of Mrs. Boxworth caressing the nipples between her thumbs and forefingers. Mrs. Boxworth moaned a deep happy sound and kissed Miss Sullivan harder. I dropped my head and closed my eyes as the two women had sex with each other.

I heard the to women stop making noises as they grew quite, then I heard Miss Sullivan call, “Jane I am concerned won’t he bleed when his balls are cut off?” Mrs. Boxworth said. “When they are at this age there is a little blood but they bounce back quickly.” Mrs. Boxworth got off her desk and said, “I have to give him something to make him somewhat more cooperative before I take his balls off”. Miss Sullivan said “What is that?” as Mrs. Boxworth produced a syringe and a bottle. Sticking the needle into the bottle she due out an amount of the fluid and tapped the syringe and smiled. “I get it from my sister, who is a doctor” she said smiling “she has found a large number of men in the town requiring castration with cancer of the testicles or prostrate, they usually beat their wives. It is surprising how much that happens” and she and Miss Sullivan laughed.

Mrs. Boxworth took the syringe and looked me in the eyes and said “this will make your change easier”. I started crying, as she walked across the floor towards me smiling “Oh he so cute.” I tried to scream as the needle hit a vein and she squirted the liquid into me. I became light headed and the room seemed to spin around. Mrs. Boxworth raised my head up and looked into my eyes smiled and looked over to Miss Sullivan and said, “He is almost ready.” I could not seem to focus on anything but knew I wanted to escape” Miss Sullivan walked around and lifted my head again and asked, “Jane I am so turned on, can we do him now?” Mrs. Boxworth looked into my eyes again and said, “he is ready, If you want to watch you have to wash him and yourself before I castrate him.” Miss Sullivan walked over and removed a wash basin from the Mrs. Boxworths closet and carried it over the taps and began filling the basin. She asked, “Jane do you want me to wash him with this soap bar?” Mrs. Boxworth told her no there was liquid soap next to basin and told her to make sure the water was very warm but not hot.

Miss Sullivan approached me with the wash basin and warm soapy water and began washing my penis and balls pulling on my scrotum and squeezing my sore ballsack. She called over her shoulder, “his scrotum is already shaved Jane” as she worked the soap into my scrotum. Mrs. Boxworth said, `I know I shaved him less that two hours ago, I had no idea I would be pruning his fruit so soon.”

I felt sick and light headed and room began to spin again, when I heard Miss Sullivan say, “Jane he has a erection just when his balls are going to be cut off”. She smiled and continued washing me, working my scrotum. Mrs. Boxworth was washing at the sink and said over her shoulder, “ever heard of being scared straight” and they both laughed hard. Mrs. Boxworth finished and had gloved hands as she waked over and looking a Miss Sullivan she smiled and said, “That is good Alice now go wash up and put on the gloves I have lain out for you and you can assist in the pruning”. Miss Sullivan soon returned and I thought I was going to pass out, it would have been more merciful if I had.

Mrs. Boxworth once more, had the ivory-handled knife, with the short curved blade. The light gleamed on the blade. She reached down and encircled the neck of my scrotum with thumb and forefinger, pinching my scrotum and then releasing my scrotum. She smiled and gently placed her up turned palm under my ballsack, I realized she was weighting my testicles. “Alice his fruit is ready for picking”, and Alice came forward watching closely as Mrs. Boxworth took the knife and held the wicked curve of the blade against my sac, gently feeling for the precious testicles. I screamed inside at the touch of the cold steel on the wrinkled skin of my scrotum. Mrs. Boxworth was going to take the final measure . “This castration will surely put an end to your vicious habits” she breathed. “I am going to prune your fruits with the gelding blade and let you live your life differently.”

Her words filled me with indescribable terror.. “Please, please, Mrs. Boxworth, don’t! I promise to be good! I tried to scream around the gag”

She slid the razor-sharp knife over my scrotum, opening two cuts on either side I stared like I was outside my body and watching this happen to someone else, not me. She said to Miss Sullivan, “Now all I have to do is give his scrotum a little squeeze and there they are”. She moved her hand and I looked as my testicles were fully exposed to the air. Miss Sullivan was standing there besides Mrs. Boxworth I remember her eyes had a strange glazed look. “Now Alice all I have to do is split the membrane” as she reached for my right testicle and “cut thought the sack, pared it back, and cut the ball off”. I watched is stark disbelieve as she raised her left hand and my right testicle was in her upturned palm. “Now I going to get his left and his problems will be over”. She again reached over and closed her hand over my left testicle, moved the knife over the membrane, pared it back and made two little movements of the knife and I was castrated.

I passed out as she said, “Alice, I’m going to close, hand me the thread out of that little basin and we take him to the infirmary.”

I awoke two days later tied to the bed with a little tent over my pubic mound. Mrs. Boxworth came in and said “I’m glad you are waking up. I want you to get out of the bed,” as she untied my restraints.

I told her, “I hate you.”

She smiled and said all little boys feel like that until their hormones are adjusted, “now get up” as she uncovered my nakedness. I tried to cover myself and hit my penis. The pain was so intense I almost passed out.

“Now get up you have to pee and start moving around,” Mrs. Boxworth said sternly, grabbing me by the hair and dragging me off the the bed roughly.

I cried out against the rough treatment my young violated body was receiving. The pain between legs was searing but I did not want her to know it so I gently slowly moved to a setting position while she eyed my nakedness.

“Good now get to your feet and go pee.”

I gingerly got to my feet and tried to walk to the toilet, nearly collapsing before I reached the toilet. I leaned against the top of the toilet shaking.

She came up behind me said, “You no longer stand to pee.”

I started crying and she put her firm hand on my shoulder. I tried to pull away but I was too weak and she was too strong. She reached over and lowered the toilet seat and pushed down on my shoulder hard. I resisted her but finally sank to the seat. I felt the cold seat against my young tender cheeks and felt the dull ache between my legs. I looked at my scrotum for the first time and saw the red enflamed shrunken violated skin, and felt hot tears running down my cheeks.

Mrs. Boxworth had a huge smile on her face and said to me, “Pee then we can get you cleaned up and ready for your new life.”

I heard little over the tears and the ringing in my ears. I started to pee and felt the pain of my castration. I finished peeing and tried to get up from the toilet and began feeling light headed nearly collapsing again. She reached down and steadied me and helped me to my feet. As she did, she reached around and handled my penis. I cried out in pain again and she smiled again, “It looks like a perfect castration job, no infection, a little pain, clearing drainage at the stitches, you are going to make it.” She went on handling me and said, “You will never be able to have sex with a girl but that is just part of your new future.”

I reeled in her arms as she helped me back to bed. She laid me out and took a basin from under bed, setting down on the bed side began giving me a warm sponge bath I closed my eyes feeling hot tears flowing again as she washed my naked body. She avoided the area of my violation until the last. She then said, “Get ready for a little pain I’m going to have to clean your surgery now so do not move, it will only hurt more if you move.”

Bracing myself I felt her hand on my penis, the pain was intense but she was gentle and easy with the sponge and she told me as she washed that soon my penis would be “nice and soft” and I would not have to worry about any more erections and the male sexual urging. I felt like crying as the pain came though loud and clear with her handling me. She finally said, “I’m all done, do you want some underwear?”

I nodded my head slowly not even opening my eyes.

She said, “Good,” and I felt her get up off the bed and heard her leave the room.

She was soon back through the door with something in her hands. She said “get up darling,” I opened my eyes upon hearing this endearment used and saw to my shock the underwear she was holding did it not look like boy underwear at all. I said to her, “that’s not boy underwear.”

She merely smiled. “You’re not a boy anymore, I intend to train you, and make you a first class eunuch in body and soul.”

I started crying again and she came over and started raising me out of the bed. I started to fight back with my anger and she slapped me across the jaw so hard I saw stars.

“Now stop fighting this, I am doing you a favor by giving you a chance to have a good life as a eunuch boy.”

I started to pull away again and she said, “Do you want me to call Alice in here to help me dress you?” I only shook my head and continued sobbing. “Very well get up and step into these.” She held a pair of shiny silky panties and I steadied myself to step into the panties. As I looked in the underwear I saw something that shocked me even more.

I stopped with one foot in and said to Mrs. Boxworth, “What is that?”

She smiled and said, “A sanitary napkin, you need to wear this until the discharge from the surgery stops.”

Warm tears flowed as she pulled the panties to my then slim boyish hips, feeling the pain of my surgery pound into my head my change in life. She had castrated me, making me a eunuch boy.