from Kay

Dear Helga,

My name is Kay, 29 years old. I am a lesbian and have a partner of three years. Her name is Lauren, 43 and she has a son whom we now call Belle (formerly Ben) he is 23 years old. Sometimes we call him our little Bellaweena. I should mention that I am professional dominatrix and I very much enjoy my job... my clients certainly enjoy it too. Lauren and I met through a friend and started a relationship. Just before her divorce, she had accepted she was attracted to women not men. At the time of our meeting, she had been divorced from her emotionally abusive husband for 5 years. I promise I'd use my UFC/ wrestling skills to kick his ass if he ever tried to give her trouble. I think she was charmed and comforted by that. So we fell in love and in less than a year, I had moved in.

Her son however, then 21 was not a fan of me as I assumed a parental role over him. I didn't care that he was not my biological son, nor that he was an adult and only 6 years younger than me, I am in a committed relationship with the person who owns the house and expected him to follow my rules as he would his mothers. But he remained defiant of me. I wanted to put him in his place for disrespecting me. In my beautifully dark mind, I began to fantasize about putting him into a submissive role where he would provide entertainment and pleasure for myself and Lauren. The ultimate tactic I felt would be most effective for this goal would be to feminize him. I would drop subtle hints to Lauren here and there about how I wanted to make him sweet and girly for us. So much easier to control. She would always respond in the vein of saying "Oh there's no way he would let us do that." I told her I'm a dominatrix, trust me I know ways. She would say things like "Oh your so bad with your kinky ideas Kay."

I continued pushing until one day she became aware that it was something I really wanted. Again, I pitched the idea again to her one night. She started responding. "You're serious aren't you? I was thinking about it the other day, it's actually really not that crazy of an idea." I told her I loved her very much and I knew she loved her son so I would never do anything unless she wanted me to, but I knew she was starting to entertain the possibility. She said she loves me and knows I know this kinda stuff very well. If I thought this is going to be good for us then she trusted me. I kept discussing and convincing her to the point where she actually became very enthusiastic. My arguments included the fact that he was a lazy little shit. He had hardly held down a job in the nearly 4 years since leaving school, never did a damn thing to help around the house, just played his stupid video games all day wasting his life away. Another convincing sway I made to her was that we wouldn't want him ending up like his father now would we? I also showed her stories and articles I had saved advocating for petticoat discipline. She began to learn how even the most stubborn males can be drastically changed by their female charges. I pushed the notion that Lauren could have a precious little sissy daughter, one that would be soft, sweet and obedient and ensured her it's quite satisfying having a feminized male around to serve you. She had somewhat of a distaste for the male sex and felt it would be a good thing to eradicate the maleness from her son, thus improving him to a much more preferable image.

My loving girlfriend Lauren was now 100% on board and I explained to her the plans. Fascinated, I had always asked my sissy clients where they bought their things from, so I had many sources to pick and choose from. I made quite a lot of money from my profession so cost wasn't an issue. His mother and I searched for pretty little sissy dresses. We picked the designs we liked best, four dresses in total: two satin - one pink one and one blue. Then two PVC maid's uniforms - one white and one black. Of course his outfit wouldn't be complete without a petticoat or two would it? We could only guess his measurements but as it turns out, we were pretty spot on. We had a lot of fun shopping. He would need to be firmly restrained during his initial training but of course, I was well stocked in bondage gear. I told Lauren this plan would work better if she wasn't home so she went out for the night with a friend.

Males, particularly young ones will be quite distracted by something sexual, they turn into brain-dead zombies. I always preferred tight, revealing clothing for myself even for casual wear. I knew he was attracted to me, I've seen him goofliy stare at my boobs and ass thinking I don't notice. This was going to be one of my tools against him. I had bought some take out burgers for his dinner.

There is an edible gel I offer my clients, used to enhance sexual arousal which I spread inside the burger. The gel will work very quickly, within ten minutes or so, he would be hard as a rock. I could tell by his face it had kicked in, but he wasn't about to get up and walk away with a raging hard on. I pulled out my phone and showed him photos of clients I had sissified, in their dresses and or lingerie just to get his reaction, some knowledge of what I'd be dealing with. Of course he was annoyed and disgusted, oh if only he knew it would soon be him. My plan was to seduce him. I told him how I thought he was sexy and that since his mother was out, we could do what we want. He was speechless and dumbfounded. I told him I knew I had been a bitch to him and I wanted to make up for it.

I stood up, pulled off my top and pulled down my shorts to reveal to him I was wearing some of my sexiest lingerie. His jaw dropped wide open. I made my way over and sat on his lap. I said, "You know, I really get turned on by these sissy men in their dresses." He stuttered "R-really?" I then pulled a bag he had failed to notice from under the table and pulled out the blue satin sissy dress. I thought it was just slightly more likely he'd be willing to try the blue one rather than pink. "You know it would be really hot if you tried this on for me." Almost snapping out of his daze, he said "What? No I'm not wearing that!" "Oh pleeease" I said, "Just for a minute and then I'll let you do whatever you want to me." He said, "Just a minute?" I said, "Yes just a minute I promise, I'll even put it on for you. Males are easy to manipulate when horny, their decisions aren't always the smartest. Without him even answering, I stripped him down... naked and saw his very hard cock, twitching and aching for some attention. I told him playfully arms up! Very quickly, I lowered the dress over him and zipped it into place, then tied the sash quite tight. I then told him to stand up and do a pose. I showed him what to do. I limped my wrists, with one over my open mouth and the other in a 'little teapot' stance. The other pose, I curtseyed, telling him to grab the skirt as he does. He reluctantly went along with it. "Now keep doing those 2 poses for me." Then I pulled out my phone. He realized straight away what I was going to do and he snapped out of his poses and said "Hey what the f*** are you doing?" and tried to pull off his dress.

What he hadn't noticed is that it was a lockable one and I had clicked a padlock in place after slipping it on him. This and the sash made it impossible for him to remove. "How does this come off, take it off me!" he demanded. I said sternly "I'll take it off when you pose for the camera. He didn't see that as an option. He balled his fist and started to approach me. Very speedily, I bear hugged him, swooped him just off his feet and dropped him to the ground. I then grabbed his wrist and put him in an arm-lock. He moaned in pain and begged to be let go. "Are you gonna have some nice pictures taken? "YES! he cried, "Are you gonna do some girly poses for the camera?" YES YES just let me go!"

Defeated he stood up. "Now do the poses you were doing, and face up! Look at the camera and smile!" After a few snaps, I simply pulled up his skirt high and told him to hold it there, revealing his still helplessly erect penis and took some more photos as he bowed his head in shame. Okay that wasn't so hard was it? I told him to turn around and I'll remove the dress. I told him to reach behind and push the sash out to give it slack so I can undo it. This then gave me the opportunity to restrain him, cuffing his wrist with a pair of leather shackle cuffs I had hidden in the same bag as the dress. Before he could swing his other arm around, I yanked it and cuffed it too. "Hey!" he said in shock. "Shut up!" I spat. I then pressured my foot on the back of his knee which forced him to kneel, attaching cuffs to his ankles. Finally, standing from behind him, I took a phallic gag and forced it into his mouth, he never saw it coming and I buckled the strap at the back of his neck. "Now look at you, nice and restrained, just how I like 'em." He was clearly angry and nervous, struggling against the cuffs and moaning into the gag.

"Congratulations. You are about to enter a new life, one where you serve me and your mother. It's time we made some use out of you. He started to struggle and moan even louder. "Oh you don't like that? Well that's okay I'll just post these pictures to your social media accounts, see?" I showed him my phone screen. "That's your page isn't it? If I click upload a file and... oh look at these pictures that pop up." I stood up and began mock typing,"What should the caption be? Feeling girly #sissyboi? How did I get into your account? You had the password written down on a post it note in your drawer you idiot. And you shouldn't use the same password for everything dumbass!" He started freaking out. I gently stroked his face '' Shhhh, calm down, don't worry, I won't post these as long as you co-operate. Sound good?" He nodded as he calmed down. I took his chin in my hand "Okay now listen carefully. Your mother and I agree you aren't really doing anything of value with yourself, so we have decided to put you to good use. You are now our servant. You will do what we say, when we say it. If you're good, you'll be rewarded. If you misbehave however, you'll have to punished and trust me, you don't want that." Do you understand, or do I need to repeat myself? Nod if you understand." He nodded sadly. "Good! Honestly you should want this too, don't you want to make your mother happy. This is what she wants for you so for once in your life, don't be so selfish."

I continued laughing, "It seems your libido has deceived you! You were so blinded by horniness that you let yourself fall victim to my plan. Your careless male need can really get you into trouble can't it?" He looked terribly ashamed at what I said, no doubt he agreed with my words ringing true. "I'm going to call your mother and tell her everything is set to go. but first..." I helped him to his feet, lifting him by the arms and then ordered him to walk. The ankle cuffs had a few inches of slack between them so walking was possible, albeit with small shuffling steps. Down the stairs into the basement, his new home. I lay him on his back on a padded latex mat. I raised his skirt to access his penis, now much softer after the ordeal and the gel worn off. I saw the disgusting little worm and knew what had to be done. I had a steel chastity cage, a very high quality one with many ring sizes for fitting options. I picked a size larger than I believed he needed, just in case for safety reasons. There would be plenty of time to give him a proper fit latter. I knew very well the effect chastity had on males, it would be an essential part of his training. I told him to relax, you're going to feel something. "Now what you're feeling on your pathetic little dick is chastity cage. You'll find you can't get fully hard in it and cumming is impossible. You'll wear it from now on unless we decide to let you out of it. Your orgasms must be earned, you'll only get them with good behavior.

I then laid beside him, staring into his eyes then grabbed the cage and started to playfully jerk it causing stimulation. He moaned as it began to get swell and hard. This confirmed to him my words were true. Laughing as I teased him, "so helpless aren't we." I helped him turn onto his stomach. Taking some rope, I tied his wrist cuffs to his ankle cuffs and pulled them together as close as they would go thus leaving him in a hogtie. He was unable to move, clearly uncomfortable and possibly in a little pain. I told him I know it's not fun, but he'll have to get used to it as he would be spending a lot of time like this." Finally the pi&eagrave;ce de r&eagrave;sistance, I took off my thong and put it over his head, positioning the crotch over his nose, a little gift to torment him through the night. I had been quite horny myself since Lauren gave me the go ahead... let's just say the panties were 'well worn'. "Now don't go anywhere, I teased "I'll be back later, you just think about how much fun we're gonna have" I laughed. I called Lauren, she was so happy everything went smoothly, and excited to to have the first step completed.

Upon her return, she could hardly wait to see him. I smiled as I embraced her gave her a big kiss. I was just as excited for her to see him. She gasped in amazement "Oh my god look at him! So precious and helpless!" He seemed disturbed by at his mother's reaction, no doubt confirming to him that she was supportive of his misfortune. She inspected him, not knowing how to take all this in. "Oh Kay, this is absolutely perfect. Thank you so much! She almost cried as she hugged me. "There's no going back now, he belongs to us. Just leave the training to me and I'll make sure he serves us well." She spoke to her helpless son, "Will you like that sweetie? Making Mummy and her partner happy? Being our little princess? He moaned through the gag once again. Lord knows what his answer was but I mockingly said "I think he said yes he would love that!" I told her we will leave him here for the night, let whats happening to him sink in. I'd just need to finish preparing him for the night. There was still the little issue of his bladder. It was only just past 8pm and he was bound to need to pee sometime between now and the morning." I went and grabbed a pack of disposable adult nappys and fixed a pair on him. I held his hand. "Now Ben, or should I say Belle, as you'll be known as from now on, I need you to make sure, that if you have to pee, you will, it's not good to hold it in. And if I come down here tomorrow and your nappy isn't wet, I'm going to be very mad, and I promise you don't want that. Squeeze my hand if you understand". He squeezed my hand. "Good girl, now try to get some sleep, we got a big day tomorrow." We ascended up the stairs and locked the basement door. We talked about how everything went and what's next, and laughed at the photos I took of him. That night, we had some amazing sex, riled up from the exciting events.

The next morning, around 6:00, I walked down to retrieve him, not sure if he had slept or not. "Morning Bellaweena! Did baby wet her nappy?" I was pleased to find his nappy soaking wet. "Good giiirrll I'm very proud." I'm sure he would have felt very ashamed of being forced to piss himself in a nappy. His body fell flat in exhaustion after I untied the rope hogtying him. I removed the nappy leaving his bottom naked for something else. I intended to start each day with a routine paddling. He would receive this regardless of behaviour. I had bought home a piece of BDSM furniture known as a 'spanking horse'. Alongside that is a cage with thick bars and a padded latex mat. This is where he would be spending his nights, if not bound in some way. I also had a big rubber bondage sack he would spend some time being all snug in. I removed his cuffs but kept the panty mask on and his mouth still gagged. I yanked him to his feet and told him to move forward. Positioning him over the table and shackling him secure. I felt a positive rush as I took the first wack with the long paddle. His body jumped and he yelped. Slowly increasing the intensity of the whacks, observing his reaction and what he could take. Soon though I cranked up the dial and mercilessly laid into his backside causing him to scream into his gag. I must have laid about 30 whacks, thoroughly enjoying myself as I did. His bottom was crimson red and tears were pouring down his his equally red face as he sobbed. "Now wasn't that fun? You can look forward to that everyday!"

Once freed, I guided him to the kitchen. I sat him down on a chair and finally removed his panty mask and gag. He sighed with relief. I cautioned him not to say a word, he is only to speak when spoken to. Even then his vocabulary will be limited. 'Yes Mistress Kay' and 'Yes Mummy' would be his only acceptable responses. It was time to get him fed, he must have been hungry after his ordeal. Unfortunate for him, his diet from now on would be restricted and healthy, promoting a slim and delicate figure. I sure hope he enjoyed that last burger haha. For breakfast, a bowl of oats with soy milk, nuts, flaxseed and dried fruit. Soy, flaxseed and dried fruits are all excellent for promoting estrogen in the body. For his lunch, some boiled eggs and a chickpea salad. And for dinner, a plate of boiled chicken and steamed vegetables. For hydration, he gets 3 600ml bottled waters a day. I told him to eat. Being hungry, he happily ate it down then drank the bottle of water. "Now let's get you properly dressed and made up for your first day as our girl." It was 6:30ish on a Saturday, still very early. I told Lauren her new son would be there at 9 to serve her breakfast in bed.

Leading him to the bathroom to strip him, I reminded him that there a photos of him I was just looking for an excuse to post. That is unless, he fully complied with my commands. I also mentioned that if he ever wanted to cum again, that was yet another incentive to listen carefully and please me. It was here in the bathroom mirror he caught the first glimpse of himself, no doubt in disbelief that he was in such a garment. I then removed the dress, first untying the sash, then unlocking the padlock, pulled the zip down, pulled his arms through the puff sleeves and let it fall to the ground. He obviously felt very exposed and vulnerable being so naked in-front of me. First I asked if he had to poop to which he responded, "I don't know" I slapped his face hard, he was stunned! With a slightly raised voice I spat "What did I say before? 'Yes Mistress Kay! -'No Mistress Kay!' I didn't even ask him again, I just rushed him to the toilet and sat him down saying he had ten minutes. I closed the door and left him to it while I prepared some things. When asked if he had done much, he almost simply said no before correcting himself out of fear to say "No... Mistress Kay". "Well you'll have another chance tonight."

Standing him in the shower,I applied hair removal cream to his entire body, scraping the hair off a few minutes later leaving clean, smooth skin. Sissies must be nice, soft and hairless, not that he had much hair anyway. It was difficult getting everything off his pubic region with the chastity cage in place but there would be plenty of time for correction later. After showering the cream off, I had him step into the bath, washing his body with creamy moisturizing soap, especially on and around his cage. He felt alerted when I reach between his buttocks and gave everything there a thorough wash. I took a toothbrush and instead of toothpaste, smeared the bristles on a bar of soap. Without warning and grabbing his jaw with one hand, I shoved it in his mouth and began brushing, He was gagging and choking in revulsion. I said mockingly, "Woops! That's not the toothpaste! Guess you'll be tasting that for a while huh." After drying him in a fluffy towel, I blow dried his hair into a the girliest style I could with what hair he had then generously applied a skin smoothing cream to his whole body.

And now it was time for a special surprise! I ordered him to bend over and grab his ankles. He shuddered in shock as I began to lube his anus... in preparation for a butt plug to be inserted. At first a modest size and a for few hours a day but I eventually would be inserting larger ones for longer periods over time. When he felt the poke, he moved forward and resisted, then begged, "No please don't put that in me" I Just stared at him. "Are you done?" I think he suddenly realized he had no choice but to comply, with the looming threat of his pictures being posted. He simply went back into position. He would feel violated and passive having his ass filled and that will be good for destroying his male confidence. I then ordered him to walk around and get a feel for it. It gave him a natural sway in his hips and wobble in his butt. With the moisturizer absorbed and dried, I applied clouds of scented baby power all over his body for extra softness. I sat him back down, he would have felt the plug pressing harder and I secured him to the chair with leather straps around his chest, hips and ankles. I then told him he needed some pretty make up and that he'll be learning to do his own soon.

My vision for his face was a glamorous yet overdone look. First an application of foundation and contour, shaping a more feminine face. His eyebrows didn't need plucking, just shaping with a pencil. Coated his eyelids in pink glitter eye-shadow. Drew on some winged eyeliner. Adhered some big, thick false lashes that fluttered beautifully as he blinked. And finally coated his lips in a shade of hot pink matte lipstick. There is no way to describe his face looking back at him in the mirror, and I doubt he could have found the words either! "You pass so well for a girl Belle, so pretty and sexy! I bet all the boys would love to spend some time with you." He sure didn't like when I said that haha.

Freeing him from the chair, I led him to his old bedroom, which was to be converted into his 'changing room'. I threw open his wardrobe "All your old clothes are gone Belle, look at all the pretty new things you have to wear!" His eyes widened at the sight of the dresses. I think it was starting to sink in how serious and permanent this was. I applied a fresh nappy. The nappies would make things a tad more convenient for the moment, no toilet break interruptions. Next I sat him on his bed to put on some stockings. White nylons, with lace and bows at the top. He let out a guilty moan of pleasure he was obviously trying to fight back as I rolled them up his legs. "It's okay to enjoy this Belle, see how nice soft, shaven legs feel?" His feet were roughly the same size as mine so I fitted with a pair of my ankle boots, with a 5 inch heel... and these ones locked! "You won't be getting these off, Belle" as I clicked the padlocks. I had him walk a few circles in them to get a feel for them. Obviously it felt weird for him but managed okay and it was quite cute to watch. For his figure and posture, I wrapped one of my corsets around, telling him to suck in his stomach as I laced it tight. I bet by now he was starting to feel a sense of entrapment. I had him step into a very frilly and fluffy petticoat and then to top him off, I fixed some satin ribbons in his hair. No sissy outfit would be complete without a nice dress. His arms up, I lowered a white PVC maid dress with hot pink frilly detailing. The skirt of the dress sat perfectly on the waves of petticoating. I stepped back to admire my work, "Absolutely stunning! You look divine, so gorgeous. Your mother is going to love what I've done to you."

I demanded he pose for some photos. One blowing a kiss, and one with hands on knees, mouth open. "Look at you! No girl in the world would be caught dead in such a prissy outfit. Yet it suits you so well." He actually looked quite ridiculous and that's what I meant by 'suits him well'. He was a pathetic sissy and he looked the part! I continued, "And you actually believed that I wanted you. Ha! Dream on. Only guys would be interested in you dolled up like that. Perhaps we'll start your own Instagram page, and you could have thousands of admirers, just imagine." It was hilarious seeing the look of utter humiliation he had hearing my words. I finished off his uniform by attaching the leather ankle cuffs, again, with enough slack to move and work but not enough for total freedom. And finally attached an item I'm particularly fond of, a padded leather collar and leash, to lead him around in. The combination of the butt plug, the heels, the corset, the ankle cuffs and now a collar to tug and pull on, he would have a world of difficulty in moving around.

It was now just past 8:20am, Time for his first cooking lesson. He had never so much as used a frying pan before. I taught him how to make scrambled eggs, Lauren's favorite. He made plenty for me too. He knew how to make toast+ jam and I supervised the making of the coffee to make sure it was perfect. I armed myself with a riding crop, from which he would be receiving a hard cut from should he fail to do anything satisfactory. For now, I had him perfecting the curtsy. Being a beginner, he copped a hit of the crop to his thighs and arms after each of the 20 attempts. Lauren was already sitting up in bed, obviously hungry, but also very keen to see her fully transformed son. We finally arrived. "Lauren, please meet your new daughter!" She put her hands over her mouth and gasped, then started to well up tears of joy. "Oh my God he is... I have no words. Look at him! He's absolutely..." She was stunned and becoming very emotional. Belle was humiliated and defeated. I was satisfied and proud.. I brushed the crop on his thighs, "Serve your mother her breakfast." Yes Mistress Kay." He answered as he started shuffling forward uncomfortably. Lauren said "Oh wow he's responding so well."..."What a lucky boy! Being able to be made so pretty."

Lauren was even more thrilled when Belle finished of the serving with a curtsy. As she enjoyed her breakfast, I had Belle kneel at the foot of her bed to give his mother a foot massage. Once she had finished eating and Belle took her tray, I made him rub her shoulders and back. "Soft but firm." I told him. Lauren was already appreciating very fast the benefits a sissy son could bring. She kissed me and thanked before setting off for a shower. I used this time to begin training Belle. He was to clean up everything from this morning. First to clean the pans, plates etc. from breakfast. Then to pick up his dress from the night before, which had to be hand washed carefully. Along with mine and Lauren's clothes from the night before. Then to clean the mess in the bathroom. He earned countless strikes of my crop along the way, for both actual and minuscule mistakes. Lauren later joined us and observed, "Look at that! Cleaning. I'd never thought I'd see him do that." "Oh Yes." I replied. "He'll be doing all the cleaning from now on, we won't have to do a thing!"All this took no more than a couple of hours, but there were other things to learn that day.

Rewards are just as important as punishments when training males. They are slaves to their libido's and as I mentioned before, he was always checking me out. Even during his transformation this morning, I still caught him hopelessly staring at my breasts through my robe, it really is funny how their mind operates. I planned to use this as positive reinforcement. We all gathered in the living room. I undid my robe to reveal my bare breasts to him. I told him "it's okay, you can touch them." He looked at me like it was a trap. I grabbed his hand and placed them on my chest. "Go ahead, squeeze them, move them, do whatever you want." He was then taken back by the sudden strain in his chastity cage, a sensation still quite unfamiliar to him. 'You'll get used to that, focus on me." "Now repeat after me, I will obey Mistress Kay at all times". After he spoke the line, I commanded "Again" each time. This would condition him to a point of mentality where he will want to please me in order to receive sexual rewards. I told him, we will do this every morning and night, so long as he behaves and does as he is told. I also told him that he was very lucky because only boys who are sissies get to touch my breasts. It was now his Mother's turn to earn his obedience. She would need to offer him a bit more encouragement since she was his Mother and all. I told her to stand behind him and reach around to grab his caged penis. I directed her to slowly and firmly pump the cage, moving his restrained cock, thus applying an uncomfortable, yet somewhat pleasing stimulation. I said that if she wanted, she could also gently grasp his testicles, give them a soft brush or a tug. Or she could even press on his plug. Then I told Belle to speak the lines, 'I will obey my mother at all times.' I told Lauren to say 'Again' softly in his ear each time the line was spoken.

Males really do blindly ignore the situation they're in when sexual stimulation enters the equation. Despite it being his mother stimulating him, he couldn't help but breath heavy, moan and enjoy it, although it was obvious he was quite frustrated at being teased with no release. For a whole year, we had these fondling sessions. It was a practice that not only gave him the mindset to obey, but kept him looking forward to it. We were the ones gifting him with the pleasure so we must be respected. This was a daily little 'keep going' treat. He was always very excited to touch me and to get touched. This kept his enthusiasm high and prevented him falling into mental rebellion, thus ensuring a functional servant .

As Lauren continued the stimulation, I got dressed. Today he would begin learning his new roles. He will be responsible for every bit of housework, Lauren and I will never lift a finger again so long as we have our sissy servant. Tugging on the leash, I led him back to our bedroom to teach him an important lesson. "You will show respect to me as your superior each day. KNEEL!" I took my foot and pushed his head down to the floor. "You can begin by kissing my feet, what do you say?" Yes Mistress Kay." He responded. "Kiss up and down my foot, make your way from the toes to my chins and then down again. You should be able to fit at least 8 kisses each way, then when I tell you to, you will switch to the other foot, do you understand?" He gave the standard response and performed a decent foot worshiping session, planting slobbery kisses, leaving light lipstick stains... all the while my crop gently stroking his back. I then pulled his collar, bringing him upright. I turned around to put my butt near his face, and pulled down my pants. I could sense his libido getting the better of him again. "2 kisses each cheek, then 3, then 4 and 5. Then repeat from 2 again. Understood!? Not too fast now." Again, his performance of the task was satisfying. It felt so amazing having him kiss my ass and so helpless to refuse. Afterwards I told him to thank me and told him he will provide his mother with the same gestures. It's the ultimate act of respect. It communicates a humble gratitude and that he fear us enough to please us. The kisses express a sort of begging. A begging for mercy and sympathy. It truly makes us feel like powerful goddesses!

If I'm feeling mean, I'll sabotage his work and make him redo it. The trick is a little technique called 'gaslighting', where you make the person believe they had done something they were sure they hadn't and they begin to question themselves. The goal here is to keep him sharp, always careful not to make mistakes. For example, one time he had perfectly folded the sheets, but once he exited the room, I made a big fold on one of them in the middle of the pile. After scolding him for it, I threw all the sheets on the ground and made him redo them. Another time I placed a few crumbs and hairs along the skirting of the carpet and made him re-vacuum the entire house to 'get it all'. These little sabotages are easily believable as oversights, making him genuinely think he has done wrong.

Over 2 years, our wittle Bellaweena has come a long way and Lauren and I couldn't be happier! Through vigorous and strict petticoating with a dominatrix style twist has turned him into the docile, obedient little sweetheart he is today. He cooks us delicious meals every night and is allowed our leftover scraps if we are feeling kind. He has become an expert in applying make up and now fully dresses himself in his outfits, a paradox where he himself must create and ensure his own degradation and humiliation.

I made good on my promise to give him his earned orgasms. When the time comes, I masturbate him to climax, at the cost of having to lick up his mess after which he absolutely hates. These however have been rare and increasingly harder to earn. I released him after the first month which is quite a long time for someone who isn't used to chastity. After every release, I increased the time before his next. He would have to wait an additional month longer than the last time. In 2 years he has only had 6 orgasms, including an accidental ejaculation when inserting a new plug. I know it wasn't his fault, but he was punished severely for it none the less.

At the present, he is well trained enough to no longer need such an award for encouragement. As far as I'm concerned, his chastity is now permanent. (But he doesn't know that haha.) Of course I am well experienced in prostate message if milking is required. I believe his long term chastity has forced his psyche to replace what he once found desirable, for a longing of feminine softness and authority. Eventually, the longing frustration and need for release would have him subconsciously enjoying these things as a replacement. After all, creatures must adapt to survive, discovering good things in bad situations is part of our instinct. He has been conditioned to accept his status and I'm starting to pick up moments where he seems to be enjoying himself, eager to please us in return for positive attention such as praise or sexual teasing. I'm glad he's warming up to his role but I'd be lying If I said I didn't enjoy seeing his moments of despair.

Our lives have been enriched as we certainly have more time to relax and enjoy ourselves, it's like we are on vacation 24/7! Feminizing and training Ben was defiantly the right thing to do. The satisfaction of owning him and serving us never gets old. I look forward to each new day and many years of happiness with my beautiful partner and our lovely sissy servant son.


How nice to hear from you Kay, thank you for writing and for your kind words about my site. Thank you as well for including your delightful letter describing your strict petticoating of your stepson, a layabout that obviously required the help that her mother and you are providing, one where everybody's lives are improved because of strict petticoating.


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Letter 4