I'm Josie, thanks to the help of Meghan and her daughter Courtney, I was inspired and able to Petticoat my son Mitchell. The three of us had been making plans for months. Mitchell was mostly a well behaved young man but he did something that upset me. With only hours of notice, he announced he was going to travel for a year.
Naturally this meant leaving his job and spending all his savings. But the worst part was that he was going to visit these seedy locations known for their partying reputation, the kind where drug and alcohol abuse are just one of the dangers. I expressed my strong dismay and begged him not to go but it was like he didn't even care. He started arguing with me and we left things in a bad place. I worried a lot after that day and found it hard to continue my business. He did however call every now and then and seemed happy.
But if he thought he could just return home after how he left things and all he put me through, there would have to be serious changes. I wanted to ground my baby forever, like a house pet. I was enthralled with Meghan's efforts. Stunned to see my boorish ex-student Casey turned into the sweetest little baby girl, so obedient and such a delightful sight having him clean for me, it really restored something in me.
Meghan and Courtney preached to me how good life was with a sissy servant and I started to imagine a life with Mitchell the same way. They stressed the importance and glory of free time and peace of mind. After my experience babysitting Cassandra, I can verify that the overwhelming rush of power and dominance cannot be exaggerated. I can also say how wonderful it has been that after a long day in front of my computer, to sit down in a clean house and read a book rather than having to worry about house duties that I otherwise would not have gotten to for weeks.
It was decided! Meghan and Courtney would assist me in transforming my wayward son into my sweet baby daughter just as Cassandra's mum had done to her. Everything was set well ahead of his arrival date. The three of us had donated all his clothes and belongings, (salvaging the valuable things) and stocked his new wardrobe with a few gorgeous sissy dresses custom ordered online including one very similar to Cassandra's favorite one. We had bought many other girly items of clothing that would make him look absolutely adorable such as tights, a petticoat, corset, heels plus adult baby gear: a romper, bonnet and large dummy. I had also stocked up on disposable adult nappies and at Meghan's recommendation, I ordered online a steel chastity cage. Until Meghan had lifted Cassandra's skirt to show me his caged penis, I had not known such a brilliant thing existed. Controlling my son's arousal would contribute to his upcoming submissive role and serve as a harsh reminder that I'm in charge.
The day had finally arrived, my heart was beating with excitement. Meghan, Courtney and myself were eagerly waiting in the living room for his arrival, ready to strike. "He's here!" I yelled. I greeted him at the door and hugged him. "Welcome home honey!" This greeting was more of a lure into a false sense of security... I was still upset with him for leaving like he did. He smiled and greeted me back as I let him in, acting his usual male self. "I have a surprise for you!" I said gleefully. Meghan called Cassandra in from the next room. Cassie smiled and curtsied to Mitchell and said in her baby voice: " Welbumb homeb Mischuel".
With eyes wide open and mouth dropped in an utter state of confusion, my son yelled, "What the hell is this, what's going on!?" I said, "You remember Casey, well after his mother and sister had enough of his attitude, they turned him into their baby girl! What do you think of that?!"".... Uhhhm" he simply replied in a nervous tone". "How could you do that to him!?" he continued. I replied, because it's made him a much better person… and I've decided it's something you need too!" He protested angrily "NO WAY!! There is no way you're doing that to me!" I told him it was too late, my mind was made up and this was the way it was going to be.
I gave the nod to Courtney and she quickly grabbed him, pulled him to the floor (she is a very athletic girl) and with a pair of handcuffs, she secured his ankles. He barely got a yell out before Meghan shoved the dummy in his mouth and fastened it behind his head. As they held him down, I yanked off his shirt and told him to stay still while I cut away his shorts and underwear. I imagine he was feeling quite violated as these three women subdued and stripped him, evident in his screams and struggles. We got off him and he tried to get up and run but tripped with his ankles still cuffed, a demonstration to make him realize resistance is futile. Courtney hauled him to his feet. I was told I had the honor of putting the pink satin dress on him! I held it in front of him taunting "You're going to wear this, isn't it beautiful?" "Arms up!" Courtney ordered as she raised them. Shaking desperately trying to free himself from her grip, I put the dress over his head and in place.
We all laughed loudly and said how pretty he looks. We carried him to a chair and tightly tied his wrists to it. We told Cassandra to stand next to him. "Aww what a lovely pair… like sweet sissy twins!" I said. After giving him a minute to calm down, I told him to listen. I explained my disapproval of his attitude with this trip and all it's resulting circumstances. That is the reason this was happening to him. "I'm never letting you go again, you're going to stay here as my good baby girl!" Tears had now begun to well up in his eyes. I said "Yes Cassandra resisted too but she eventually accepted it. We've chosen a new name for you too... from now on you are Michelle." I revealed his new chastity cage. With not a word of explanation, I assembled it on him. Though confused by the strange device, I knew he was smart enough to figure out what it's for. Meghan said "We have an effective method for calming sissies like you down.
Just like Cassandra several months before, Mitchell was going to experience a time out. I had no sizeable linin cupboard but I cleared space in my wardrobe for him which worked just as well. We all dragged him to his punishment space. I fixed a nappy on him and said to use it if you have to go wee wee. "You'll be in here for a while." Finally thanks to the fantastic tip from Meghan, I went to my room to remove the panties I had been wearing since yesterday morning. I returned to place them over his head and positioned the crotch over his nose, his eyes in shock as I did. He was left for two hours. Meghan said to Cassandra "You're going to have a new friend to play with Cassie, won't that be fun?" He answered "Yeff mumby, she wooks bery pwiby, I cumb wai to pway wiff her." Cassandra had an easy week, I was saving forty percent of the housework for my new daughter. Then ten percent of his duties will consist of one task I desired that Meghan had not expected from Cassandra: Cooking! While Meghan was determined to put her baby to bed early, I would be teaching Michelle how to cook for me. Thus his bedtime would be later.
Once his time out was complete, Courtney put her make up skills to work. Still tied to the chair he received his makeover… mascara, blue eye shadow, red lipstick. She said he was ready so we walked in to see my son so well made up, so lusciously feminine, he was unrecognizable! I hugged him and kissed his forehead, and told him how happy I was with his appearance. I told him I was going to free him from the chair but he had to do as he was told. "Things will be different now Michelle, good girls do what they're told. I expect total obedience from you. When I tell you to do something, you'll do it! Understood?" He nodded. "Good girl.
Now I'm going to show you what happens when you don't comply". Meghan pushed him face down on my bed and cuffed his hands to the bedhead. I got a long thick ruler and whacked his bottom ten times. Crying and shaking, I told him as long as he behaved, that it won't happen often. We completed his attire with a petticoat skirt, tights and a bonnet. With demonstrations from Cassandra, Michelle was educated in conduct. I told him that Cassandra will act as your role model and mentor and he should strive to be a good baby girl just like her. The three of us had a lot of fun that afternoon and I felt this great joy wash over me. Michelle and Cassandra needed to be fed. We strapped him to his high chair and presented Meghan's special mush in front of him. "Open wide baby" after I spooned it in, he spat it out in disgust. "What the hell is that!?" he whined. I slapped him across his face. "How dare you! Meghan worked very hard preparing that for you, now eat it up like a good baby or you'll starve!" I made him eat it while he cried.
My new sissy son was a delicious sight I simply could not look away from. I was pleased to see he had wet his nappy. "What a good baby" we all said pulling his nappy to have a look. The shame bought him to tears. I asked him if he needed to go poo. He shook his head no. I explained that he can't use his nappy to poo (we don't like messy situations) and he'll have to wait until morning where he will use a potty. He understood. "Lets get him shaved!" Courtney said excited. After stripping him, we watched as Courtney removed all his body and hair and what little facial hair he had. (We are now considering laser hair treatment for both Michelle and Cassandra.) At 3 o'clock, we bathed him but he needed another spanking for refusing to get in the tub. Everyone, even Cassandra, watched as I washed him from head to toe. Maximum humiliation was surely felt. Meghan and I took him to his new pink painted room, where he saw for the first time what his new life is all about. If he wasn't already gagged with a dummy, he would be speechless. He set his sights on the new cot and change table built by Meghan's contractor. He was clearly in awe at the length we had gone to feminize him. His room decorated with dolls and baby toys. Meanwhile, Courtney was bathing Cassandra. I had ordered the most sissy piece of sleepwear imaginable: a pink, tight PVC romper, 2 of them... one was for Cassandra! What she didn't know was that her and Michelle would be having a little sissy sleepover.
At Meghan's recommendation, they would be put in his cot early for his first night as my baby daughter. We laid him on the change table and powdered him up and applied his fresh nappy then I slid the romper up and zipped it. It was fingerless and padlocked at the top so it was inescapable. Soon after, Courtney brought Cassandra in and the process was repeated. Cassandra started to figure out what we had planned. Meghan told her "You'll be spending the night all cozy with your new friend Cassie" She didn't look too happy about it as Meghan fastened her dummy.
We laid the two beside each other. I said to Meghan that since the rompers make them helpless, there's no need to restrain their wrists." Instead, I had an extra set of bars hinged to the top of the cot that closed and locked. It was essentially a cage. We just stared and had a conversation over them for a good half hour. Meghan said "A perfect baby girl and a bad sissy about to begin training, sleeping side by side. What a wonderful sight!" They weren't friends when they were boys. In fact when they were ten years old, they had a punching brawl with each other and then another at age 14. They would be getting along much nicer now (laughs). I hugged both Meghan and Courtney and thanked them profusely. A tear of pure joy broke from my eye! "It is a very exciting time for us!" Meghan said. We had a nice dinner and talked about feminization training well into the night.
The next day began his training in housework. We dolled the pair up all nice and laced Michelle's corset tight. The 2nd uncomfortable thing for him was a pair of high heels. He struggled to keep his balance for days. For weeks before, we had told Cassandra that she will be responsible for teaching him household duties. The two of them remained dummy gagged so neither could plot rebellion and with a suggestion from Meghan, the 2 were handcuffed at their fronts for their duties to make things oh so much more difficult for them and entertaining for us. I explained to Michelle that Cassandra will show you how to do something, then you'll do it! Got it? We supervised them for 20 minutes to make sure everything was right then we left them to it.
Courtney had to go to work, she was sorry she couldn't see Michelle in action. When she came home in the afternoon, she was thrilled to see the pair in the most amusing outfits. I bought each of them a matching pink leotard and ballerina tutu. I surprised Meghan with them. "They will look so sweet dancing in those" she said. We put on an instructional ballet DVD that they had to follow. They looked ridiculous with their nappies bulging out the edges of their leotards. Courtney said. "I can tell they just love prancing in those outfits!"
Once the DVD had finished, Courtney brought out 2 pairs of handcuffs from her handbag. Without telling us what she was doing, she ordered Michelle and Cassandra to hug and positioned their arms in an embrace. She then cuffed each of their hands behind the other person. They were locked in a hug, unable to raise their arms above. We all said "Aww how sweet, they must really love each other" we laughed. Courtney joked "We'll have to start planning their wedding HAHA!" They were not amused and we left them like that for an hour. Meghan had told me how Courtney promised to use petticoat discipline on her man should she marry. So latter I suggested in private, "Perhaps you should marry my Michelle. She is after all already on her way to becoming a complete sissy, it would save you the trouble of finding another guy to transform." With an agreeable grin, she responded "Hmm... not a bad idea at all. She was handsome as a guy and now she makes a very nice girl." I said "I'm sure she would make an amazing wife for you Courts!"
After many weeks of training, he has become just as good of a cook as I. First at 5, I feed him. He is fed the same mush Meghan makes for Cassandra. It was very nice of her to offer to make it for me. I bathe him at 5:30. He starts preparing my dinner at 6:15pm to be ready and served at 7:00 sharp. He places the meal at my table, curtsies and says "Pwease emjoy your meawwI mumby" Then I enjoy it in front of him while he kneels beside me, waiting to take my finished plate and wash it. I find it particularly amusing he doesn't even get to taste the delicious meal he worked so hard on. Like Cassandra, he is denied the privilege of nice food. I place him in his cot at 7:30. When I babysit Cassandra, her and Michelle make a great team. I have a little bell that I ring that calls them to me when I'm working. They curtsy and ask : Yeff Ma'am. How may we serb woo." in their cute baby voices. Whether it's a making me a cup of tea, giving me a massage, updating me on their housework, or just providing me with entertainment, when I want something, I ring the bell and they come to serve... It's great!
One month into his training and he still isn't happy about his new role but after all, it's a punishment and I don't expect him to enjoy it. Just last night after putting him in his cot, I told him "It was a few months before Cassandra took to her new life. I'm sure in time, you'll learn to appreciate and love being girly. You also should realize that this is not a game, you are my baby girl. This is your life now and I intend on keeping you like this permanently. You are being trained for the rest of your life." You could see in his eyes something had sunk in, a sudden realization of his situation, he had to accept his fate.
I so enjoyed the new free time given to me by Cassandra's efforts but now with my own sissy servant Michelle catering to my every need, life is sweet. I frequently go out on the weekends with Meghan while Courtney babysits and we babysit when Courtney wants to go out with her friends. For so many years of running my business, I neglected and forgot the purest joy of free time. There are 2 special people I have to thank for that. I owe it all to my wonderful best friend and her lovely daughter.
Thank you so much Helga, I hope you enjoyed reading my letter. Your website is amazing and I praise you for your efforts.
Thank you for your letter Josie. Congratulations on taking control of your wayward son using this very effective form of petticoating and diaper discipline. The help of your very experienced was invaluable and along with the fine example Cassandra sets for proper sissy behavior you could expect life to be much easier, for you. Thank you as well for your kind words about PDQ, it's success is due to the generosity of our contributors sharing their successful experiences.