It's so nice to talk to you again. I write to you once again about my own sissy daughter. As promised, here is an update on Cassandra's progress. I'd like to inform your readers of our divine exchange of emails where new ideas for Cassie's punishment were discussed. I must credit Helga for her fascinating suggestions and solutions. I had promised to spend a month trying out the new techniques and then report their effect. This all started when I sent a list of additional details to her and she gave me her input much to the delight of my daughter and I.
I would like to share these details. First I had explained how his time out session was actually a last minute idea. It wasn't until after he was secured to his chair that I had told Courtney that's what we'll be doing. The thought of him helpless, bored and in a weakened position in the dark for 2 hours struck me as a very effective punishment and I was sure it would calm him and give him time to process what was happening. It became a regular and favorite punishment as soon as I realized it's effectiveness. I had him nude during the time out because as you can imagine, it would make him feel exposed and fragile. The other idea was to hood his head with something, perhaps a pair of soiled panties.
I informed Helga that I had an idea to keep Cassie's hands secured at his front with cuffs whilst having to do housework to make it that much more difficult for him. She then suggested I make him clean the kitchen floor with a toothbrush. I extended this thought by also having him clean the bathrooms and toilets with one as well. I told Courtney of these ideas and she simply couldn't wait to try them out.
So here is the scenario of these plans put into action: On a Saturday, I secured his hands together at his front with handcuffs. He was confused and had no idea what he was in for. We had been having usually warmer weather so today we were going to try having him work completely nude (not even his nappy) only a pair of heels. We had purposely made a big mess of the kitchen, bathrooms and toilets. Courtney handed him her toothbrush she was about to throw out. "Today you will be cleaning with this." She said. I added "You have 1 hour to get everything done!" This was a ridiculously unfair amount of time and unrealistic expectation to complete the job given his bondage and cleaning tool. "For every minute you are late and for every bit not cleaned properly, you'll get 2 minutes in time out." Oh the look on his face, he couldn't understand why we were being so particularly cruel.
He struggled to clean and was panicking to get it done in time. He must have been kidding himself if he thought getting it all done within an hour was a possibility. It was so funny to watch but we had overlooked the fact that because he always had a nappy on, he was used to urinating himself whenever the moment struck him, therefore he had little control over his bladder and being so nervous, hadn't even realized that he urinated all over the kitchen floor. By chance, Courtney caught him in the act. "OH MY GOD!" she yelled. "The stupid sissy is p***ing in the kitchen!" I added "You bad sissy baby! Clean this up at once!"
He apologized over and over as he cried and begged for forgiveness. Mercilessly, we both got struck into his behind with the ruler. I knew it wasn't really his fault but any chance to assert our dominance through a degrading situation is always taken. By the time passed and mistakes made, we had calculated he earned 5 hours which conveniently would end an hour before weekend bedtime at 4PM. We complained mockingly that it shouldn't have taken so long (knowing full well it was beyond his ability given the state he was in.) From that day forward, he only does chores cuffed and all scrubbing is done with a toothbrush. It's proven delightfully difficult for him and very entertaining for us.
For his longest time out ever, was the time to try the soiled panty hood. After tying him to his chair, I went to my room and pulled off the pair I had put on for bed last night. To his horror, I placed them over his head! We both laughed loudly. "Enjoy the smell of my panties sweetheart." For 5 hours I felt such a positive tingle as I imagined him naked in the dark with no choice but to breathe in my worn panties. With an agitated and tear stained face, we came back for him. I said "If you had finished in time, you could have avoided this punishment." Then Courtney whispered in his ear. "Next time you'll get to experience my panties!"
The next day he experienced just that. As I prepared him for yet another lengthy time out, Courts returned from the gym. She went to her room and removed her thong, this time ready to go in her sissy brother's mouth! All part of making his time out more unbearable. He struggled and moaned as she tied a stocking over his mouth and around his head to keep the panties in place. Soiled panty hoods and gags are now a permanent part of his time out. We alternate between who's go over his head and who's go in his mouth.
Courtney simply adores having complete power and control over her once tyrant brother... seeing him in such a delicate form. I really don't know what I would do without her and her enthusiasm for looking after Cassie. She told me it's a quite a delightful thing to constantly tease and taunt him and cause him despair. At this point I'd like to mention, one thing Courts loves to torment him with is making him look at pictures of boys. Despite his heterosexuality, she is determined to turn him on to guys. She's always showing Cassie pics of sexy men on the iPad she took from him. It's a real way to mess with his mind and also shows him what he can never be.
One idea was conceived mutually between Josie, Courts and myself, that our 2 sissy daughters would be spending a lot of time getting to know each other. When they do chores together, we decided to handcuff one of their left hands to the other's right. They are stuck together and have to work cooperatively as partners to complete their chores. Soon we might try cuffing their ankles together in the same fashion. It's fun to watch them struggle. Of course there's their ballet lesson from the DVD when they get to spend some quality fun time together. At least once a week, the pair has a sleepover and share a cot. I just had my bathroom redone with a much bigger tub, the 2 are occasionally bathed together, sometimes fed together, and because they work together, they receive time outs together.
Once they are stripped, one of them will be tied to a chair and one will be seated on the other's lap with their hands cuffed around and behind the back of the one in the chair. When they are being released, we can see their erections in their cages and we tease them about being lovers. Looks like Courtney will have her wish after all. Perhaps a mutual milking would be a fun activity, Michelle has yet to have hers.
(Taking the subject back to Cassie) His chastity is my favorite part of his training. It keeps him insanely frustrated yet docile at the same time. Though he's only had 3 milkings in 10 months (one per 3 months), I've not informed him that is his schedule. It'll take him a while to figure out. It keeps him on edge wondering when he might be given the glorious opportunity of release. Whenever a milking day had arrived, my steps were as follows:
I would strip him and cuff his hands behind his back so there is no getting carried away. I'd tie his dummy in place... I didn't mind him moaning but this helps silence it. I would lead him to my shower and stand behind him. I cuddle across his stomach with my left hand to hold him still against my body. With my right hand I masturbate him to climax. My aim was to get it done a quickly as possible. As soon as he spurted, I let go. As you can imagine he would be desperate to release, so both times it hadn't lasted more than 10 seconds before orgasm. As soon as it was done, I blast him with cold water for a minute. This shrinks his silly willy right back up ready to be caged again for another 3 months.
I don't do it for his pleasure, just his relief, she informed me of a milking technique I had heard of but didn't know much about. I had expressed my desire of preventing him from feeling any pleasure and my dismay of him being erect. I had researched prostate milking more extensively. With a latex glove and lube, you insert a finger into the rectum and massage the prostate until fluid oozes out. This is supposed to drain his prostate while feeling no pleasure. It was also suggested a witness during this humiliating act would be appropriate. I had Courtney watch and even play a little with his locked privates to help things along whilst watching for any leakage. However I am disappointed to say that our attempts have been unsuccessful. I will keep trying, but we have yet to achieve. From what I've read, it takes a certain touch and a bit of practice for a successful prostate milking. When asked if he felt anything, Cassie reluctantly admitted to a little discomfort but nothing more.
About a month ago, it was Cassie's birthday. He would be turning 23 (although you wouldn't know it by looking at him). She revealed the gift I had for him; the chastity cage with spikes in it. This is what happened on his special day; Josephine and her beautiful baby girl Michelle were invited over. He was to spend the morning in his 'birthday suit' so to speak. Josephine bought from the news shop, a sash that said 'Birthday Girl' for him to wear. I put him in the corner while we all had some cake. All of us were to give him 23 birthday spanks each... even Michelle was told he could spank Cassie as well and was actually quite excited to deliver the blows. This totaled 92 whacks and I added 8 to round it up to 100. The pair was finally allowed some cake, but only after their piece was dipped in vinegar.
It was time for Cassie to open his gifts. His thoughtful sister had bought him some naughty lingerie, his first set ever! It consisted of a red silky lace bra and thong with matching stockings. We dressed him in it immediately and my oh my did he look sexy. Josephine had bought another naughty item; a butt plug! "An essential item for all sissies, Michelle is wearing one right now!" She said. His face turned stunned as it finally hit him what the plug was for. By this point in his training, Cassie knew better than to struggle or resist. I simply bent her over, and with lube inserted the plug. He looked so uncomfortable and started to quietly moan in displeasure. I said "Oh stop whimpering, you'll get used to it. Besides, it's something a sissy like you deserves, now thank Miss Williams!"
Cassie was dreading each gift he had to unwrap but the piece de resistance; the chastity cage with spikes in it was yet to be revealed. I'm sure Cassie almost fainted when he unwrapped it. With teases and laughs from Josie and Courts, I told him to stay calm as I removed his old device and assembled the newer, more unforgiving one. Courtney said. "Your peenie is about to learn a harsh lesson Cassandra!" as she approached him. Courtney began gently playing with his caged penis to stimulate it, thus inflating it into the spikes! Squeals and cries filled the room and he eventually fell to his knees in an attempt to relieve his pain. Michelle looked on in horror, probably fearing a similar fate. "Good, just how I like you, sobbing at my feet, now kiss them!" Courtney scorned. I added. Your arousal won't be tolerated anymore Cass, from now on, whenever you feel frisky, your new device will put you back in your place. Later that day, I had one more gift for him. I gave him one last hand milking (until perhaps next year), before being locked back in the cage.
One last thing I must share. Now the weather is turning colder, both Cassie's and Michelle's attire has been changed for the season. They wear tight pink leather pants and white knee high stripper boots to keep their legs and feet warm. The usual satin dress, padded bra, corset, petticoat and nappies keep their mid-section toasty. Then with white PVC gloves to keep their hands and arms warm, a woolen bonnet and pink bubble jacket, they are as snug as 2 sissies can be... and of course a good spanking with the ruler keeps their backsides nice and heated.
Well that's about it for now. I can say that Cassie is more obedient than a well-trained pet. One order or hand gesture and he obeys faster than a bolt of lightning. He has learned that we are top priority. He knows to provide maximum service and treat us like goddesses. He looks simply adorable in his winter attire! Life is still sweet for Courtney and me. We shall write to you again for any notable updates and hopefully you have more tips for punishing him.
Lots of love,
Meghan & Courtney
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Thank you for your letter Meghan. I am delighted to hear from you both, I was happy to read that you incorporated some of my ideas into his punishment and training regime. His new device should stop any foolishness and provide security as well as remind him of his place in the pecking order... at the bottom.