Dear Auntie Helga,
My long journey into sissification and submission started many years ago before marriage and the internet. So probably like many others it wasn't much of a journey, as opportunities were very limited to purchase anything appropriate. So the desire went unfulfilled, but was always there.
And then I met my beautiful wife, Elizabeth, and in the heady days of romance, courtship and marriage, the feelings were suppressed. It just didn't feel right to burden her with such a surprise, and the fear of rejection was too great. But as the internet increased the range of possibilities, and the embarrassment of purchase in person was removed, the time came when I could no longer resist the urge to dress as I had long wanted.
I didn't want to have "the conversation", so decided to try and broach the topic in another way. One day I bought my goddess an Anne Summers French maid outfit. She wore it once, but of course I hadn't really purchased it for her, and one Sunday morning I surprised her with tea and toast in bed, appropriately attired at last. Let's just say it met with great approval, and great reward (!), so emboldened it became a Sunday tradition. Lying in bed each week to test the water I would talk about how a proper maid should really have the next item, lipstick first, which my wife immediately obliged with, and maybe a bit of eye shadow too. Next week I borrowed a suspender belt and stockings from her drawer, which, to judge by the response, really turned her on. And so over a year I built up a full outfit, wig, shoes, petticoat and more besides.
Step by step I had gained acceptance of my new position as the sissy maid, even if I hadn't used that expression yet. But to my relief I hadn't needed to have that awkward conversation that most men struggle with when introducing the subject of cross-dressing and submission, and by introducing each part of the outfit one by one, never gave her too much of a shock - thankfully always to great approval, and sometimes amusement.
Over the next few years I found a mail order shop, Wendy Jane, long gone, that sold sissy dresses of different colours, so again, I softened Elizabeth up "Celeste really needs a pretty pink dress, doesn't she?", and in time pink, baby blue and yellow dresses were added to the better quality black sissy maid's outfit I'd already purchased. Each one met with a positive response, and when I offered to do domestic duties dressed - well what wife would refuse that offer?
With chores now a regular feature when dressed, the time came to purchase some appropriate items of discipline so that, with a little encouragement, my now mistress was encouraged to punish me in the event of any transgression or below quality work. And suddenly that encouragement turned my wife from a willing participant in my harmless pleasure to the dominant mistress that I had so long craved. There was to be no turning back now...
With Mistress now in full control over me, I soon found that maid was on duty more and more frequently. My underwear drawer quickly filled with satin and lace, and several more sissy maid dresses arrived, some pastel colours, some bright, some gingham, and more petticoats too. Every outfit would have heels to match. Each night my dress for the following day would be hung out ready for me, depending on Mistress' mood.
Mistress also decided that even when not a maid, women's clothing would be the norm around the house. So over time a full wardrobe was acquired, and each day Mistress lets me know whether I am still to be a sissy maid for her pleasure, or can choose my evening attire for when she returns home. But whichever is chosen, Sissy Celeste has to have the house spotless, with any specific chores completed, and with the dinner in hand on her return from work. I was also told that I would need to be completely smooth, and now my daily ritual includes ensuring my body is completely hairless before starting my morning's duties.
Chastity became a key part of my training too, which Mistress discovered to her delight quickly resulted in a much more attentive and submissive maid. My devices gradually become smaller, which Mistress told me was necessary as my already pathetic apology of a penis withered to an even more inadequate size through lack of use. Over time, removal became even more infrequent, just enough to prevent any health problems, and usually only permitted when restrained, to prevent any inappropriate temptation on my part.
It won't surprise you to know that the daily inspection usually finds some fault in my work, and this is duly rewarded with an appropriate punishment later in the evening. If I'm lucky it will be a short over the knee spanking, but usually the flogger or paddle is called for. I dread the evenings when I have to kneel before her to present the tawse or cane, though I know that it's all part of a sissy's training. Weekends are reserved for more elaborate punishment based on my overall performance during the week. They often involve a humbler or rear hook, and those together with electric stimulation concentrate my mind on how I should improve my behaviour and work.
Until recently Mistress would always lay out which nightie she wanted me to wear in bed, be it a demure Victorian cotton one if she was tired, to a flirty baby doll if she wanted my tongue to worship her. As mentioned, my rewards however have slowly reduced, with removal of my chastity cage becoming more rare, and the introduction of milkings replacing the more carnal pleasures. When I questioned whether Mistress missed such attention, she observed that my tiny member had not been capable of giving her any pleasure for many years, so for her it had only been a chore to humour me. Mistress also has learned about ruined orgasms, which ensure that the milking is purely on health grounds, rather than giving me any pleasure.
However, in the last year things have taken a wonderful new direction. As a birthday surprise, Mistress bought me a baby blue broderie anglaise baby dress, nappy cover and bonnet. Delighted by how pretty and sweet it was, I soon become her baby boy every night. Why a boy? Well she delights in fiddling with my tiny hairless winkie and marbles and telling me how they are so small that the doctor is going to have them removed and turn me into a pretty little girl. So now I have several baby outfits, pink, blue, floral, two piece outfits, rompers, and each night Mummy chooses which I wear. And she's got me some sweet little party dresses for Sunday best too, with petticoats, thick tights and Mary Janes to match. I do like it when Mummy makes me up with her powder and lipstick.
I've now got my own nursery, with Peter Rabbit soft furnishings, and every night Mummy bathes me, pats me dry, powders my botty and puts my nappy on, together with mittens and booties. The mittens are padded and tied, leaving me completely helpless for the night. After a story and a bottle I'm put to sleep with some lullabies. I fall asleep such a happy baby, and even enjoy waking up with a full nappy as I've trained myself not to wake up during the night too.
Sunday morning has now become my regular milking time, always heralded by Mummy tying my pacifier in place to avoid any noises unbecoming for a baby. She gently tells me how important it is to rid me of all my little boy juices before the doctor can come and do her snip-snip. Recently Mummy has started spoon-feeding me my creamy squirties, as she's explained that it means less cleaning up for her. Though as she still stops just short, the resulting dribble is barely a spoonful now. I've also been told that Mummy is considering a new technique for milking that doesn't involve removing my cage, and even less enjoyment for me. In preparation for that she's starting plugging my botty at milking time, as she says I will need to expand a bit more before it's ready for her.
So now I'm Sissy Celeste every day, and come bedtime I'm Mummy's sissy baby too. I really am so lucky to have such a wonderful understanding wife who has taken control of my life and helped me find my true position as a submissive sissy. I do worry though that she does not have enough pleasure herself, and that she should invite one or more gentleman friends back to entertain. Do you think it would be appropriate of me to suggest that to her? I would like to have a Master and Daddy and think it would be good for her too.
Thank you for your letter Sissy Celeste. What a wonderful letter and thank you for sharing the details of your sissification and becoming the beautiful sissymaid you are today. Your honesty with your glorious wife has led to this lifestyle you share now, her dominance will continue to grow over time as will your willingness to submit. Should there come a time when a real man joins in, well, of course that would be her decision though I will say that if your relationship is one where she will allow you to make your feelings known, then certainly you could express yours about including a Master with all that entails.