The Convict/My Prison Folder
The Holding Centre
My Day In The Cell
I Am Sentenced
Arrival At The California Institute
I Start Serving My Sentence
Ms Mary Keeps Me In Order
The Stories of Yvonne Sinclair
The Story Of T
The Sacred Feminine
The Weight Loss
A Caning By Miss Spiteful
A Visit To Greenwich
At My Lady's Pleasure
Ball Shackle Story
I Met Claire In A Coffee Shop
Long Weekend Conclusion
Robin's Electrical Torture
Slave To The Cane
The Escape Artist
The Huntress Caning
The Language School
The Worm's View
The Bossy Bank Women
Chapter 7 - Ms Wilson
I was still kneeling, my hands still cuffed behind my back, and my ankles shackled. One of the guards stepped forward struck me across my buttocks with a short black leather whip. It really hurt!
“Stand up, convict. Walk straight ahead....keep your eyes ahead and down on the ground.....back straight!......No talking! I will be right behind you!” the guard ordered.
I obeyed. Everytime she instructed me to turn, she also gave me a stoke of her whip across the back of my legs. It hurt like hell! There was no reason to use her whip! This woman was obviously a sadist!
She directed me to a stone building at the far side of the courtyard. Inside, we came to a closed oak door.
“Kneel” the guard ordered, with another stroke across the back of my legs.
I obeyed. The Guard knocked on the door. “The new Convict is here, Ms Wilson” she called.
“Bring him in, Mary” I heard a voice call from inside the door.
“You will enter on your knees, Convict, without speaking, and with your eyes on the floor! Do you understand?” said Mary.
“Yes Ma'm” I said, trying to sound docile. I did not want to get the whip again!
Mary swung the door open.
“In, Convict” she ordered. And gave me yet another stroke across my legs! The Bitch! If only I could get out of these handcuffs!
I shuffled into the room on my knees, my eyes fixed on the floor in front of me. I was desperate to escape, but I coudn't do anything while I was in these cuffs and shackles!
“Stop” said Mary. I stopped.
My eyes were down on the floor, but I could just see the legs of a large desk in front of me. And a pair of woman's legs. She was wearing black high-heeled shoes. I felt my ankle shackles being moved, and heard the click of a padlock. The guard had padlocked my shackles to a steel ring in the floor.
I heard a voice from in front, above me. I did not make the mistake of looking up without permission!
“Convict Smith....I am Ms Wilson, the Director of this Institute. This is a Private Institute for the confinement of selected men. Most inmates are troublesome husbands who are placed here by their wifes, some for short term punishment, and some for permanent confinement. Other inmates are males with unncontrollable masochistic desires. We are especially pleased to confine such men, since it keeps them out of the trouble that their impulses would otherwise get them into. Finally, we also accept Federal convicts sentenced to life terms, such as yourself, since the Government is short of prison space, and we offer completely secure imprisonment at very low cost to the Government. The Government income from Federal prisoners, like you, is an important source of revenue for us, so we make sure our prisoners never escape. We do that very simply: we keep our prisoners locked in their cells, 24/7”.
I heard the rustle of papers.
“Oh. I see from your folder that you have a life sentence! Do you have hopes of escape? None of my prisoners has ever escaped! I assure you, you will serve your complete sentence! In full!”
She laughed. “It might take a few years for you to understand that! But you will!”
She returned to turning the pages.
“And I see you are classified as “violent, dangerous and an escape risk”. Very well. You will be kept under maximum security. That means you will be chained, and will be kept in one of our strip cells! I'm sure you know what that is! You'll be naked, in a bare concrete and steel cell. No loose articles. None at all! No reading materials. No radio or TV! No appeal! No visitors, except members of the Institute!”
I groaned inside, but I dared not speak.
Mary spoke. “Ma'am...excuse me....there is also a personal letter from Ms Jenner in this convict's folder.....I was asked to draw your attention to it”
“Thank you Mary” Ms Wilson said. “Here it is.....”.
“Hmm........” there was a pause as Ms Wilson read the note.
“This letter informs me of the nature of your crime! You are a convicted serial rapist! Its good that Ms Jenner told me that! You can be sure that I will remember that, if I need to discipline you!”
“And..... I see that Ms Jenner recommends that you be punished immediately you arrive, for insolence to her during your sentencing! I shall of course be happy to oblige my friend Ms Jenner. She recommends 20 strokes of the cane! So that is what you shall have!”
'You may look up at me now, convict!” she said.
I looked up. She was staring down at me, with her wide dark eyes. I could not bear her eyes. I immediately lowered my eyes. Not that she was ugly....on the contrary, she was too lovely! But I could not bear her burning eyes.
She was old. In her 30s at least. It was hard to tell, but definitely a lot older than me. I only dated girls. I again thought how strange it was that older women attracted me so much.
“Very well....it's good that you look down. Its the correct response, since you are completely in my power. And I can see it came naturally to you....from your heart! I like that! But I wanted you to know who will be in charge of you from now on!”
Ms Wilson walked around behind me.
“Keep your eyes down, now, convict!” she ordered.
She stood behind me. I knelt, naked. Her prisoner.
“Prepare him, Mary, please! I'll give him his punishment myself! I'm in the mood for it!”
My ankle chains were unlocked from the ring. I was ordered to crawl to a wooden bench in the center of the room. It was constructed of a heavy oak plate, about 5ft long and 3ft wide. At each end were pillories, one for ankles and the other for neck and wrists. The wood was dark and polished hard and smooth by much use. I was ordered to kneel on the plate. My ankles were locked in the pillory. My head was pushed down and the pillory locked around my neck. My face was held a few inches from the floor. I was held in a keeling position, my ass held up high, perfectly positioned for caning. My wrists were still cuffed behind my back. I felt a chain passed around the cuffs, and my cuffs were pulled up hard towards the neck pillory. I heard the click of a padlock.
I heard Ms Wilson walk around behind me. I felt her hand run over my buttocks. I tensed.
“Relax, convict” she ordered. “There is little you can do!”
I felt her hand on my skin. Her fingers traced the weals on my thighs. “I see that Mary has had to use her whip down here...”
“Only on his legs, Ma'am” said Mary “his ass is still unmarked!”
“Yes.......I do see that....thank you, Mary. I like to work on unmarked buttocks......and this boy has such nice smooth skin!”
She continued caressing my skin with her hand. “I love to see an unmarked male ass..... waiting for my cane!“ she said quietly into my ear.
I trembled. This woman was a sadist too!
And I had never been caned before! I had no idea what to expect! It was probably going to hurt!!!
“Does my touch frighten you, boy” she asked, stroking my buttocks gently.
I was silent.....I wasn't sure if I was allowed to answer.....she had not given me permission to speak...
She realised why I hesitated. ”You must always answer direct questions, convict” she explained. “Also, you may beg during your punishments! We enjoy hearing men beg when they realise they're going to be punished! And anyway, you will not be able to remain silent once your punishment begins! You have our permission to yell as much as you like, during your punishments here!”
“But even then...when you beg, beg respectfully.......unless you want extra strokes!”
“So, answer my question!”
“Your touch feels good, Ma'am. But I've never been caned before! I'm scared of the cane!” I said desperately, scared. I was helpless before her.
“Oh! Never been caned! I'm pleased! It's a rare pleasure to give a man his first caning! All the convicts here..... they have all been caned SO often.....” she sighed. She did not seem sad however.
“This will be a new experience for you! And it's completely understandable that you are scared..... you should be frightened of the cane!”
“Now, since this is your first time......its my privilidge to show you why boys fear my cane......”
I heard her take a step, then the whistle of her cane.....
I yelled in pain, I could not help it. I bucked in the straps, but could not move! It felt like a line of white-hot fire across my buttocks! The cane was MUCH worse than I had imagined! Sweat ran down my face.
“Please......it hurts” I moaned.
She laughed “Did it? Really?” she said, amused. “And you bucked so nicely! I like it when I see that boy feels it!'
I felt her hand run over my buttocks, and her fingers tracing the line of the stroke.....I could feel that a raised wheal was aready forming!
Slowly, the pain lessened. I could breath again.
She walked around in front of me. “You mark very well! That stroke made a really nice weal! I wonder what twenty will look like on you! You seem to be calm now...... so let's try another.....”
“NO! Please......Ma'am, please don't............No, please!!!!!
She walked briskly back behind me.
“It's time for your next stroke, boy!”
“OHHHhhhhhh!!!!.....please.....!!!!!!!” I yelled.
The second stroke felt even worse than the first one! And the pain seemed to be taking even longer to decrease!!!!
Her fingers gently traced the second weal, which was rapidly rising, about an inch below the first, and exactly parallel to it. This woman was an expert with the cane!
“That was a good weal, too!” she said with pleasure in her voice.
“And did that one hurt too?” she asked sarcastically.
I heard her take a step, and the whistle of the cane....
CRACKKKKKKKKK!!!!! That one was easily worse than the first two....
“I've already told you....you must answer me when I ask you a question, Convict! “she said, her voice sharp now. “That disobedience has earned you five extra strokes!”
Oh God! Five extra! Oh....
“Yes, Ma'am!” I gasped....”Yes! That hurt! It really did, Ma'am!!!!! Ma'am....please.....forgive me! Please don't give me five extra! Please! Please! Please!!!!!”
She ignored my begging.
“Sorry. I never relent over any punishment! Its a principle of mine, never to relent! Its the only way to obtain obedience, I've discovered! So....you will have five extra, no matter how much you beg!”
I pulled desperately at the straps. I could not take that many!
“And....that was just the start. I'm going to give you the FULL punishment now! This will be the remaining...let's see...... twenty-two strokes! You will get them all, without a pause! This is where you learn to respect the cane......”
'NO!!!!!!!!! Please NO!! Please NO!!!!!!!!!!!!!Please Ma'am!!!!! Please!!!!!!!!!!!!.......
She laughed. “Beg all you want, convict.....it won't help you!”
I heard her step back.
“You WILL learn to respect the cane, boy!”
Her cane whistled. Then again, and again..........She gave me the remaining 22 strokes, rapidly and without pausing, as I bucked and yelled, tightly strapped down to her punishment bench, my ass held perfectly in position for her cane......
At last it stopped. I was sobbing and moaning, struggling in the straps.....it was SO painful, it was worse than anything I'd ever experienced......now I knew what a caning punishment was like! I'd never be disobedient again! Never!
I felt her cool hand running over my striped ass. Over my sobbing, I heard her talking to Mary.
“Beautiful! Come and look at his ass, Mary! Such nice marks! He marks so well! And I do so like the way he bucks and yells when he feels the cane! He's really good! Let me know if he needs any canings again....if I have time, I want to do them myself! And get him scheduled for a weekend party as soon as possible!”
“I'm sure he will need lots of canings, Ma'am....” I heard Mary answer, with a laugh.
Ms Wilson turned back to me and spoke sternly.
“You now know what a punishment caning is like in this Institute! Here, I insist on COMPLETE OBEDIENCE from all inmates! If you wish to be caned again, all you have to do is to be disobedient! If I get any reports of disobedience, I will cane you myself!”
She lifted my chin, and stared into my eyes. She seemed to be searching for something in my face.
She smiled. “Ah.....it is there, in your eyes.... you can't hide it!.........you have spirit.....I see you are still proud!......you sgtill don't submit, do you....even now you have felt the cane?....... So wonderfully brave! But I WILL break you, boy! I WILL make you submit to me, completely! ALL my prisoners submit to me....eventually!”
“But with someone arrogant, as you are, I will take special care. So Ms Mary will be your supervisor. She is experienced in handling men like you!
She turned to Mary.
“Take him to his cell now, and lock him up. I'll put a note in his folder that his sentence formally began at.....fifteen minutes past seven. So please have him locked up by then. Keep him well disciplined, and bring me monthly reports please. Bring any gross disciplinary issues to me, of course, for caning. And I'll personally inspect him again after his first year. Thank you Mary.”
To continue this story, click My Cell
Back to the top