I have updates on my progress with my sissy maid cousin I'm sure you will love to hear! I had him read my previous letter. Not this one however, at least not until much later. I wanted to write this to you Helga without the knowledge he won't be reading it any time soon so as not to alter any details just for the sake of his torment. At the end of this letter though, I want him to write a few words of his own to you, which I will attach at the end. I showed him PDQ and our exchange of emails which he was very embarrassed by. I have him read all the new letters from PDQ each month to me aloud which is great for practicing his female voice but most importantly learning about petticoating and to normalize it for him in a sense.
So anyway, he has improved a lot in the months since I last wrote to you thanks to my relentless determination to mould him into the perfect sissymaid. After almost 2 months of waiting, the PVC sissy outfits and accessories finally arrived! The extra tight, super short dresses, panties, maids bonnets, stockings and gloves. It was all quite expensive but oh so worth it. Presenting them and dressing them on was next level for him, it was almost like beginning the petticoating again, much worse than before. As you could imagine he was very unused to such feminine and sexy sissy wear. He couldn't believe the new level of f***ery that was happening to him. He sort of went still with anger and frustration during the dressing process as he knew there was absolutely nothing he could do about it.
I on the other hand was high on a rush of excitement and admittedly, a little arousal finally fitting my preferred choice of wear for him. I stood him in front of my bedroom mirror and the look on his face was priceless. A huge grin forced itself onto my own as I felt his ego being crushed! I wanted him to take it all in and truly feel the weight of his situation. In front of the mirror, I sat him on a chair and secured his wrists and ankles to it with some duct tape. I watched him for a while as he kept bowing his head away in shame, unable to stand the sight, yet unable to help but keep looking back up and over himself again in astonished assessment. I kept him there for about an hour during which he began to audibly sob. It had finally all caught up with him and he awoke to the reality of it. In response, I taped his mouth to keep him silent. He was truly broken but I wasn't done yet.
In the heat of the moment and to add insult to injury, I decided now would be a good time to implement a method I have seen on letters to PDQ. After removing the bonnet, I took off my panties and lowered them over his head, leaving him breathing in the wet crotch section then replacing the bonnet once more. New shock and tears began for him as I laughed. "Mmm yes don't my panties smell good? Breathe it all in now." It felt so good having my panties over his face, forcing him to breathe me in, I can't quite put it to words. He had never seen this side of me and I'm sure he gained a whole new respect for me since. Even after releasing and putting him back to work, I kept him gagged and panty hooded until dinner time. As you know Helga from my previous letter that this is not his first experience with my soiled panties. I mentioned how he had to everyday, wear my pair of mine from the day before with a devious excuse to do so. I still have a reason to re-use them by having him sleep with the pair from that day over his head the whole night while he is secured in his sleep sack. I love sleeping with him down there next to me knowing he's breathing in my scent all night long. I often masturbate whilst thinking about it into the next pair, knowing where they are going.
At first, he was quite unhappy in the demeaning and humiliating outfits, not to mention how tight they were but knew very well by now not to dispute it. He's been getting around in them for almost a month now and for the first couple of weeks, I enjoyed every second of his discomfort and humiliation. I'm sure he's no doubt reached a new level of low self opinion, a weighted blow to the male ego for sure. Verbal humiliation is important as well as I love complimenting and mocking him on his appearance; "Such a girly little thing you are. What a gorgeous, sexy outfit! You must feel so soft and pretty in it. I bet you're loving every second, you know this is what you really want." It's amazing what an outfit overhaul can do! I noticed a rapid improvement in his demeanor, skill and obedience soon after.
Before the new outfits, he was indeed getting used to the new position. It was becoming his identity and purpose to please and serve me, replacing the old, no hoping useless male one. Since the new outfits, he's definitely realized this is not just a little arrangement we have but a permanent lifestyle and a complete re-moulding of self. He's also managed to learn that willing submission will earn approval and praise that he now seems to crave. I notice his enthusiasm growing in all sorts of instances and I think he likes having skills he can say he's very good at and take pride in, most particularly whilst watching him apply his makeup each morning, even if though it's a feminizing task, trying very hard to make himself look the prettiest he can be for me.
To address your readers directly for a moment: In our exchange of emails, Helga inquired whether I use, or plan to use the intimate services expected of sissy maids. Well I had planned to use a potential sissy boyfriend or husband for oral service so even though he is my cousin, he is still my sissy and thus have absolutely no problem is using him in such a way. In either case, it's not something to be rushed. Establishing positions and getting familiarized with one another was something that had to be taken care of first. I wanted to drive him to a point where he would actually want it too. Helga had fantastic ideas for conditioning him to love my body. I had already established a foot worship routine where he rubbed/ licked my feet and sucked my toes as well as taking care of pedicuring duties and Helga mentioned we should bond by painting each others nails which was delightful.
She also recommended a dressing routine where he is to undress me for showers, watch me shower, dry me and re-dress me all while being locked for months. He even has to wash my body if I'm bathing. Running soapy slippery fingers over wet glistening breasts drives him crazy! He had never even seen a naked woman before in real life let alone touched one so despite me being his cousin, combined with the months of chastity, the poor young hormonal thing is riled up which is evident if not by his longing eyes then by his heavy breathing and seeing him strain in his cage during the service. On the weekend, a warm bubble bath with candles whilst he slowly washes my body and hair, virtually messaging me is very relaxing. I love having him pamper me with a good blow dry and lotion application too!
Speaking of chastity, at the beginning of his petticoating, I had promised that if he behaves, I'll let him out of chastity to orgasm. Initially I thought once a month or every two months would be good. But here we are 5 months later and I simply have no desire to let him have one. I love him perpetually frustrated, thus addicted to me and don't like the idea of giving him such pleasure and relief. The thought of the silly little thing free from it's cage and fully hard doesn't sit well with me either, It really does belong locked up, and soon in a much smaller cage too! The only time I let it out is to shave the area and thank goodness it grows slow and in very small amounts. He does get rock hard when I handle his genitals for shaving and rest assured, he is given a very hard spanking later for such a disrespectful display. Fret not Helga for I am aware that males need milkings for healthy prostates which is why I began researching articles and videos on the matter. He has had two successful, orgasm-free milkings now and will receive them every month. I loved having my fingers penetrate his sissy hole, gently messaging his organ and eventually watching the fluid drip out like a tap. He moans and twitches a little but he doesn't enjoy the process of being invaded and worked like that. Both times he was surprised when it was over and he felt no pleasure.
I have him on all fours in the bathroom on a bathmat then sit on his back like a pony before getting my gloved fingers in there, it's an oddly powerful feeling. I explained to him that this will replace his orgasms and he will never be allowed the pleasure of one again. He cried and begged, how could I possibly deny him orgasms permanently!? I told him because that's how I want him and a pathetic sissymaid with a tiny locked penis isn't deserving of one nor has any say in the matter. This was the perfect opportunity for something I had been wanting to try. I had gotten carried away and found myself horny, unable to help grinding on his back as I administered the message. I said to him, "I'll show you what a real orgasm is." I had him crawl behind me to the bedroom. I sat on my bed, spread my legs and pointed to my pussy then ordered him to come closer. He crawled over nervously but also with arousal in his eyes. I told him to begin licking. The moment I felt his tongue I was buzzing. I began moaning in pleasure and so did he. I clamped his face between my thighs and grabbed his head, pushing him into me as I rocked and squirmed. Eventually he bought me to a furious orgasm that the neighbours definitely heard. As I lay back on my bed in a dizzy wave of euphoria, he remained kneeling there obediently. It was done, the seal had been broken. I knew from that point on, I would be using his tongue regularly and he is now my avid pussylicker.
Of course, the orgasms he gives me now are even more intense and satisfying not just because he's had plenty of practice, but also because I usually have him fully dressed in his delectable sissymaid outfits which is a very satisfying sight to enhance the experience. Yes something about the extra tight dress with way too short skirt resting on a frilly petticoat exposing tight panties. Topped off with the stockings, gloves and maids cap all in shiny, hot pink PVC looks incredibly scrumptious on him. And soon, I'll add another layer of sexiness (or for him, discomfort) by ordering a corset for waist shaping and some nice matching heels to walk around in. Being a bit of tomboy myself, I simply enjoy a T-shirt, jeans and runners with little to no makeup. This makes for a very nice contrast between us. I'm sure he is jealous I get to wear whatever I want while he has to wear such a ridiculously feminine get up, with much more makeup than myself. To compliment the upcoming waist training, I've already been training him with booty workouts. I require and nice shapely butt from my sissymaid and I will work him hard to get it. So far, it's shaping up nicely so to speak. And the best part, he does it all in a white latex leotard, one that rides completely up his butt which I enjoy grabbing and slapping during the workouts. They are also crotchless, leaving his caged boybits dangling out. This is mainly to avoid crushing his balls during movements but also looks really nice. He's described the leotard as 'worse than being naked' because he is fully exposed yet still in a girly costume.
I got the subtle nudging from you Helga in your emails that you were encouraging me to refer to him as her/she which I promise to do in future letters, but as a lot of this letter was detailing the improving transitions from useless male to perfect sissy, I thought the he/him pronouns would be more appropriate, if not for clarification sake. I never did mention his original name because honestly it's not important but I am delighted to share with you her new name: 'Lillie Shinygirl'. I know it sounds like a mouthful but for some reason, I love saying it, calling her and addressing her that way. It defiantly conveys the vision she is. I would still love to one day be able share Lillie Shinygirl with my close friends and also her Mother and mother's boyfriend but at least right now, the cons are outweighing the pros. I guess I just don't want anything to jeopardize our little relationship and end up losing my sissy maid. Well that's everything that's gone down these past months since last writing you that I hope you enjoyed hearing about. It's been an absolute treat training her and having such a pretty, sexy maid serve me I feel so lucky. Of course it's even better now due to current events, I work from home and get to spend the whole day with her. She often messages my legs or shoulders while I type away, just like now writing this, she is slobbering her tongue on my feet. I'm quite worked up upon completion and think another pussylicking is in order. "Up now Lillie!"
P.S. I will now pass on to my sissy maid for a few words of her own. Well... it's mostly her words:
Hello Auntie Helga,
My name is Lillie Shinygirl and my Mistress has ordered me to write a few lines that tell you my side of being petticoated and serving as her sissy maid. I was first told to thank you for your website and for publishing the letter about me. I can't actually believe something like petticoating exists and that many people do it. I'm shocked by what I read a lot of the time but I'm also comforted knowing I'm not the only one going through this. I couldn't believe the letter she wrote to you about me and that you know everything and even worse, I have to write to you now. She's told me to just write down my honest feelings so here goes. I hate the new dresses and things she makes me wear. I'm wearing them right now and I feel ridiculous and pathetic but strangely also very pretty. I also hate the name she calls me I really do especially when I have to write lines of 'My name is Lillie Shinygirl'.
I thought I could manage getting used to our original agreement in the old dress but now things are getting crazy. And I hate that she won't let me cum. As you know, she keeps my penis locked up in a chastity cage. I was hoping she would let me out but is saying I can't cum ever again which worries and frustrates me. I hope she changes her mind one day, maybe if I please her enough. Despite all this, I do appreciate and respect her and know she's fair in a lot of ways. I enjoy keeping her home clean and cooking her nice meals, watching her smile at me for a job well done. She allows me intimate privileges that I look forward to and love pleasing her with. She's made me realize what a hopeless male I was and I'm thankful she took me in and gave me purpose, even if I don't fully agree with it but she knows best and I'm sure I'm where I belong. For this, I always aim to please her as best I can. I often lay awake at night thinking about the future and it's looking like I'll be stuck here for a very long time under my cousin's command so I figured I better get used to it. Thank you for listening to this sissy's thoughts Ma'am.
Thank you for your letter Kate. Your experience is an inspiration to us all, your training of your cousin is well thought out and carried through with strict administration which is always best.
Lillie Shinygirl, you are so fortunate to have a Mistress of Kate's expertise, to have her take her valuable time mot train you to worship her, from her panties to her glorious body. Having these wonderful uniforms to wear just makes this so special, I hope you appreciate it all.