I led Jaime from the garage to my master bedroom in the back of the house and told him to get in the Waiting Position as he had done before and to remain silent until he was told he could talk.  I smiled when he nodded his head up and down for yes since he had just been denied the right of speech.  Perhaps he may just become as valuable as he appears on first glance, but that was rarely the case and each sissy was a reflection of the woman who transitioned him from his maleness.  He was merely the canvas.  I was the artist, and I hungered to begin my art.

I thought about securing him to a wall hook, but since he had not had his obedience ring piercing under his scrotum, I could not yet use one of the little locks I require all males to have attached to their obedience ring so that at any time I wish I can use my master key to unlock the lock and then lock them to one of the many eyehooks securely mounted at various places around the house and grounds. I was more interested in getting him clean and introduce him to my strap-on before introducing him to the worship of my pussy.

“I know it seems your world has come crashing down around you, Jaime,” I told him as I entered the master bathroom where I had one of the two walk-in closets converted to a workspace for sissy training and I had taken my time in designing it to make the most of the space and it had been well worth the effort.  “And in a way it has, I suppose, but this is what has been decided for you, Jaime, and the best thing for you will be to accept your new circumstances and learn obedience and devotion to your new owner,” I continued as I began selecting things from one of the built-in shelves.

“And I am your new owner, of course,” I said happily.  “Did you know that, Jaime?  Did you know I own you now?”

“Um, no, Ma’am,” he answered from his humble position.  “I did not know you could own someone.”

Laughing, I emerged from the training closet with several pink disposable lady’s razors, a scrubbing brush, washcloth, and, of course, the bottle depilatory cream and turned on one of the special water nozzles that were custom-designed to fill up the huge, four-person Jacuzzi bath in minutes rather than hours.  “Oh, you are trying to be smart, I think.  Can’t own someone, how cute,” I said smiling as I set a bottle of lady’s shaving cream along with an opened bottle of bath salts next to the other supplies on the side of the huge tub.

“Well, you can own a sissy maid cuckold, like you,” I told him plainly.  “Female Supremacists like me have been systematically transforming bois like you into sissy maid cuckolds for decades now, Jaime.  We are working toward the establishment of a matriarchal society known as the Gynarchy, and in this new world inadequate males such as you will be transformed into sissy maid cuckolds and will be owned by the women you serve.”  Only a week away from turning seventeen, at least according to Susan, he would be seventeen in a week, he was afraid and unsure of what was happening to him and why.

Picking up his leash, I jerked once and the boi immediately began to get to his feet, still slowly and unsure of himself but it was obedience.  “We will now learn 'Perch Position,' Jaime.  Stand-up straight and tall, feet together, knees together,” I instructed him as he tried to process my wishes and do as I ask.  “Now your arms are at your sides, but your wrists are held together at about the center of your chest, almost as if you were begging,” I instructed him.  It took a little arranging to get it just right, but overall, I was pleased.

“Good girl,” I said to both praise and humiliate him.  “Now, Jaime, I want to get you cleaned up, top-to-bottom, and while we are working on getting you ‘sissy-clean,’ I will explain some of what is happening to you.  Now step into the tub and be sure to watch your step as it might be slippery,” I told him as he obeyed my instructions and stepped into the bathtub for the first time.

“Now first, you will be getting rid of all that boyish hair,” I told him.  “First, let’s do your legs.  You will use the washcloth and soap to first clean your legs, Jaime.  I am assuming you understand what that means,” I told him as I unfastened his training collar and watched him begin to do as he was told, first tentatively and then, once he understood what was wanted, with some dedication and what I thought was attentiveness to task, a good sign if I truly had recognized the trait. 

He was a very, very pretty boi, I recognized once more as I watched him clean himself.  Although much too fat for a sissy, he was naturally small and not very muscular with wonderfully thick, dirty-blond hair he had grown down to his collar.  His lips might need a little work, but generally speaking, he had that look sissies sometimes have on their own — that suckable lips/mouth combo that can be so hot.  His breasts had wonderful potential as well and I simply loved the shape and look of his nipples.  I would use only hormones to grow small, cute breasts on this one, I realized immediately.

As he was finishing washing himself I sat on the edge of the tub and motioned for him to come closer.  Already, I could see he was fighting an erection and my touch would likely be enough to let his little boyish cocklette get hard as I put my hand around his waist and began to apply shaving lotion all over his body and when I thought I had enough I began rubbing it around and in between and over until I covered him from waist to knee where the water level had reached and I quietly turned off the loud nozzle from filling the tub any higher and returned to my work.  I began with his thighs and once finished I moved on to his pubic region.  Fortunately, he was not very hairy, and a few electrolysis treatments would have him permanently denuded.

As I began to shave him, he began to fidget, ever so slightly, and in a few seconds, I watched as his cocklette grew to its full, erect size — barely four inches long and likely less than an inch in diameter.

“You are very small, Jaime,” I told him as I continued shaving him.  “Do you know that you are much, much smaller than average?”

“Um, I, um, guess,” he said quietly.

“You guess?”

“Yes, Ma’am,” he answered.   “I mean, I have never seen another man, so I don’t really know.”

“Oh, Jaime, that is so cute, that you still think you are a man,” I said, laughing.  “You are not a man, Jaime.  You never were much of one, anyway, and now you are becoming a sissy maid cuckold for me.”

“Um, yes, Ma’am,” he answered, clearly excited and responding the way a sissy should to being humiliated by a strong woman. 

“You are a weak, panty waist sissy,” I told him as I continued shaving him.  “Look at how excited you are getting from being dominated and controlled by a powerful woman who knows what you are and what to do with you.  No real man would allow this, and it certainly would excite him.”

I had him reach back and pull his bottom open for me so I could shave his bottom and after I had done a fairly good job of removing all hair from his bottom I took his scrotum in my hand and squeezed his sac in my hand until it filled out like a balloon that is filled with air and then began running the razor across his scrotum until it was reasonably free of hair.  He winced slightly, but his erection remained and if anything grew even harder at my treatment.

Moving to the walk-in shower, I started the water and reached out for his hand as I instructed him to step out of the bath and into the shower.  Making sure the water was warm before I let him step under the shower, I wanted him to keep his erection and use it to humiliate and emasculate him as we removed all the hair from his neck down.

“Step under the water and wash all the shaving cream off your body now, Jaime,” I told him.

“Yes, Ma’am,” he answered as he stepped into the shower and began letting the water wash the shaving cream from his body.

“Are you ready to admit you are not much of a man, Jaime?” I asked as he washed away the shaving cream.

“Um, I, um, I guess, yes,” he said, nervously considering my question as he washed away shaving cream and tried to ignore his erection.  “Yes, yes, okay, I can see why you think so,” he added.

“Oh no, sissy boi,” I laughed.  “It’s not an opinion.  It is a fact.  You are not a man and never have been a man, Jaime.  Just accept it and you will be happier.” 

He had washed away most of the shaving cream and I told him to step out of the water and face me with his hands on top of his head and his legs spread about two feet apart.  Once he was in position, I began to apply hair removal cream on his thighs, legs, pubic area, and under his arms.  Unable to help himself, he whimpered with sexual pleasure as I worked the cream over his body.

“How pathetic,” I said laughing at his excitement.  “You are excited and want more, don’t you, Jaime?”

“Um, yes, yes, Ma’am,” he answered, the lust in his voice incredibly obvious.  “I am excited.  I do want more!”

“Good girl, Jaime,” I praised and humiliated him at the same time.  “Perch Position now, sissy, Perch, pretty little sissy.”

Jaime immediately stood up straight and brought his hands to his chest, wrists broken to make it look more effeminate, arms tight by his chest.  His cocklette remained fully erect and I could see seminal fluid beginning to leak from its head.  After ten minutes, I could see the depilatory cream was beginning to burn his skin and he began to twitch as it heated up.

“Under the water now, sissy,” I finally told him and with that, he hurried under the relief the running water offered as it removed the cream.  I used a washcloth to remove more of the cream and we both watched as the small hair he had left below his neck washed off his body and down the drain.  After he was free of the cream and his body hair, I told him to return to the tub and begin rubbing his skin with a hard bristle brush to get him nice and pink and raw.  He began to scrub himself, but the hard bristle brush was painful after the chemical action of the depilatory cream on his skin.

“Bear down, Jaime,” I told him.  “You must remove all of the skin that was burned with the depilatory cream before we can move on to cleaning your insides.”

“Yes, Ma’am,” he replied, really trying to do what I asked of him, and I let him try his best for a few minutes before telling him to stop and taking the brush from him.

“On your hands and knees, sissy,” I instructed him and quickly he complied.  From the ‘Training Closet,’ I pulled the stainless-steel enema stand and filled the pink enema bag with warm, soapy water from his bath.  Seeing what I was doing Jaime panicked and jumped up slightly and I grabbed a handful of his hair with one hand and jerked him up, so our faces were close.  “That will get you punished, Jaime.  Now, are you going to allow me to finish getting you sissy clean inside and out or do we spend the morning teaching you all the ways my paddles and whips can make bitches suffer?”

“Yes, Ma’am,” he said, beginning to cry once again.

“Behave, or your punishment will only grow in severity,” I said as I let go of his hair and first attached the tubing to the bottom of the enema bag, and then I added the insertion nozzle with the expanding pump.  I worked a little lubricant up inside him before pushing the nozzle inside him, slowly but without pausing to allow him to stretch and soon he was whimpering in both pain and pleasure as I began to pump the expanding nozzle and let him feel it grow larger and larger in his ass until it was so tightly secured in his rectum there was almost no chance of him releasing it without my permission.

“That’s it, bitch,” I said as he continued to moan and whimper.  “You are actually very lucky I am making you into my sissy maid and cuckold, Jaime.  Look at how pathetic you are already, moaning and humping the enema nozzle like the sissy slut you were made to be and that I will help you become.”

“Y-y-yes, Ma’am,” he whimpered as I turned the water flow on and watched him react to being filled with the enema water.

“Now, let’s discuss your new life while you are being filled,” I said smiling.  “You will focus completely on serving me and meeting my needs as your needs no longer matter.  A sissy maid is just that — a male who has been fully feminized and who serves as a maid to her owner.  Sissy maids are feminized, but you will never be a girl and I plan on dressing you and styling you so that it is obvious to everyone who sees you that you are a sissy and not a woman.”

Jaime whimpered, partly due to being filled with an enema and partly, I sensed, from the humiliation of being told what I was planning for him.  I reached up and took the enema bag in my hand, telling him to look up at the bag as I handled it.

“You have about a third of the enema inside you, Jaime,” I explained.  “When the entire bag is empty, it will be uncomfortable, but not terribly painful, because I am showing you mercy since this is likely your first enema.  I’m sure you want to thank me for my mercy, don’t you, Jaime?”

“Oh, yes, Ma’am, I do,” he moaned, his erection still mocking him as it showed proof he liked what was being done to him.  “Thank you so much for your mercy, Ms. Rebecca.  I’m very grateful.”

I smiled at his effort and entertained how much fun I would have with this sissy.  It was incredibly sexual, incredibly exciting — taking a young male and breaking him to the point he would accept feminization and even embrace his emasculation with the right training and conditioning.  To watch him become weak and helpless, and then to watch him accept he was now she and would never be able to live like a man ever again.  To enjoy the fear and shame in her face as the hormones began working and she began to develop small, sissy breasts as she became increasingly unable to achieve a full erection although I never pushed hormones so fully that the sissy became unable to achieve orgasm by having her cocklette stroked and manipulated.  Admittedly, I only allowed her to retain limited function of her cocklette so that demanding she remained locked in her chastity cage for longer and longer periods without an orgasm would be the agonizing torture sissy bois denied for long periods of time began to experience continually without relief.

“Good girl, Jaime,” I said.  “And from now on we will accept your ultimate fate and begin referring to you as ‘she’ and ‘her’ and ‘girl.’  You will never be the weak, pathetic male that defined who you are up until now, and you will never be allowed to frustrate and disappoint women by pretending that tiny cocklette is anything a woman would want or enjoy.

“And as my maid, you will be dressed in a maid’s uniform at all times and it will be locked onto you so that you cannot remove it without my permission.  And underneath your uniform, you will wear a bra and matching panties, a locking corset, and a pair of four-inch heels, also locked on your feet.  You won’t be able to do anything without my permission, and in time, as I training and condition you properly you will come to accept having your decisions made for you so you can focus all your thoughts on obediently doing what you are told.”

Jaime moaned a little louder and I could see he was crying, and crying without breaking into sobs, the way a sissy cries when she begins to see she has no choices and her life will be mine to manipulate and use any way I wish.  I laughed at her and squeezed on the enema bag before turning the nozzle to increase the flow to full.  In less than a moment, the little bitch had something real to cry about!

“Oh, poor baby,” I mocked her.  “Is that enema making you cramp?”

“Yes, Ma’am,” she agreed as she cried.  “It hurts.”

“Yes, it hurts, but it is nothing compared to how I can make you cramp if I decide you will take a full bag.  The bag you are taking currently was only filled three-fourths of the way,” I told her and brought my hand down hard on her ass to help make my point.

Jaime jumped and then, realizing her error, began apologizing and immediately tried to resume her original place in the tub.

“Stupid slut,” I said as I went into my closet and got a one-half-inch dowel rod from the dozen or so I had of various sizes and whipped it back and forth in the air to let the bitch hear the small wooden cane cut the air.  “That will cost you.  When you are told to remain in place you will remain in place, or you will be punished.”

“I’m so very sorry, Ms. Rebecca,” she said, her fear making her beg honestly.

“And why must I punish you, Jaime?” I asked her to begin her conditioning.

“Um, because I, um I moved and I was supposed to be still,” she said, now whimpering from the pain of the last of the enema filling her.

“Yes, true enough,” I agreed.  “But why must a sissy be punished?  Try to think.  Try to understand why it is necessary.”

“Um, because punishment makes me obey better,” she said quietly.  “I mean punishment makes me more obedient.”

“Yes, exactly right, Jaime,” I told her as I reached over and removed the tube from the nozzle, pushing the enema stand to the side so she could see what I was doing from where she knelt.  “I am proud of you!”

Pathetically, she responded hopefully to my praise just as every sissy will respond to the praise of her owner, all of them eager to please and hopeful that obedience will somehow be rewarded.

“Sissies like you are punished to help them learn obedience and acceptance,” I explained as I tapped her lightly on the ass with the wooden dowel.  “Punishment is hard, and it is painful, but it is good for you and necessary.  I demand absolute obedience and compliance, Jaime, and you be an obedient and compliant sissy.  Do you understand me?”

“Um, yes, Ma’am, I think so,” she said as she tried to stop her involuntary whimpering.

“Well, when I’m done, you will know so,” I said as I brought the dowel down hard across her ass for the first time, laughing as she yelped in surprise.  Soon she would be begging for mercy and then soon after that she would simply scream and cry out in pain as I would not stop until I had her nicely broken and hurting from the unrelenting pain I forced her to endure.