Dear Auntie Helga,
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I would imagine I am unusual in writing to you as I am a 60 year old dominant male who has over the last 40 odd years trained literally dozens of sissy men to serve their betters and become useful as sissy maids.
My first experience was as a 20 year old when I spent a summer staying in London with my aunt and uncle, I always had a soft spot for my aunt as she was only 28 and extremely attractive my uncle was a quiet man of 32 at the time and it was always said in the family that Janet (my aunt) "wore the trousers" What I did not know was that Frank, my uncle, wore the skirts!
How I came to find this out was one day when I had been to a football match and returned home my aunt Janet was sitting in the lounge looking very annoyed and Frank was nowhere to be seen. My aunt said "sit down please I have something to tell you" I took a seat and my aunt informed me that my uncle was upstairs waiting to be punished for being naughty, I had a job not laughing but said "naughty Aunty?"
It was then that she told me that just after the war my grandmother found herself widowed when my grandfather died of lung cancer leaving her with 5 children to bring up, 3 girls and 2 boys (David my father and uncle Frank) and that Granny used a method of punishing the boys called petticoat punishment, at this time I had heard nothing about the subject. Basically my aunt said that granny had found it very effective and that my father never gave her any cause to use it on him after the first time, uncle frank on the other hand spent most of his adolescence in his sisters old clothes and in fact when he was 18 and my aunt just 14 she was a friend of the family and often saw him dressed as punishment.
My aunt then said that a few years later when she and Frank got married she informed him that at home he would be her sissy maid at all times and would only wear female clothes in the house, the only exception being when they had visitors, hence I had not been aware. My aunt then asked me if I wanted to see "Francene" and also learn how she made her income I was fascinated so followed my lovely aunt up to the third story of their home where I had never been.
There was a small landing with three doors off it and she opened one to show a baby's nursery with a cot, high chair, etc. but all adult size the next room was a school room with desks and blackboard and the final room was what I now know to be a BDSM dungeon in the middle of this room was a low whipping bench with what looked like a French maid tightly tied to it with their bottom in the air and their frilly panties around their knees
My aunt led me to this person's head and I realised it was my uncle, heavily made up and gagged, he looked appalled to see me grinning at him my aunt then said "Francene" is going to be caned did you want to watch or leave I told her i wanted to watch and she then laid into her husband with a vicious cane, after about 30 strokes she asked me if I fancied giving the sissy a few strokes? I gasped and said yes, and that was the first time I got the thrill of caning a sissy one I have never got bored with! After that I spanked and caned Francene often during my stay and also moved into my aunts bedroom and we became lovers (there was no blood relationship) and I learnt she had always wanted to cuckold him and with me it was the ultimate humiliation.
During that summer I learnt that men would pay well either to be dressed and beaten or to beat Francene my aunt told me she never had sex with clients but was happy for them to use Francene sexually. I left after that summer for university at Southampton where I studied electrical engineering.
I had a quite normal first year although I spent all my holidays in London with my aunt and her sissy however during the first part of my second year I came across my first sissy, a fresher named david who I instinctively knew was submissive and having invited him to my flat for a meal and drinks got him thoroughly drunk and soon had him agreeing to go to the freshers ball which was a fancy dress party dressed as a schoolgirl with me as a headmaster.
I had great fun at the party and David, who I renamed davina became my sissy live in maid for the rest of that year and the following two of his degree. I stayed in Southampton having got a good job there and davina stayed as my sissy maid until she finished her degree in history by now she was my slave as well as my sissy maid so I informed her she would not be getting a job but would be staying as my full time sissy maid, it took a fair few canings before she agreed and also a trip to my aunts for training before davina realised her true destiny, to serve her betters.
After some ten years I had my own engineering business and had began training sissies more assisted by davina who was by now devoted to me and living 24/7 as a female. Things continued much like this for the next few years until I got the sad news that my beloved aunty Janet was dying of liver cancer. I sold my business and moved in with her davina came with me obviously, much of our time was taken up discussing Francenes future as Janet had divorced her formally several years previously and had made me the sole beneficiary of her will.
It was decided by Janet and myself that Francene, (now 60) would transition fully as a female before Janet died and be put into a residential home to live out her days, it did take several thrashings before Francene agreed but eventually she did and had her final surgery a month or two before my beloved Aunt passed away.
I had already got her nursing home lined up and she went in there a couple of months later I still visit her every two weeks and cane her in her room for old times sake! I then began to train sissies full time with davina's assistance my preference was to train reluctant husbands who had either cheated on or far worse abused their wives and usually agreed to training as a sissy to avoid a divorce.
I confess the pleasure of turning a wife beater into a simpering sissy maid is huge and one I never tire of especially when I, ironically, show the once beaten wife how to thrash their new sissy!! I am currently in the early stages of training a new sissy who has just turned 18 a son of a friend who assaulted his sister and agreed to accept my training as an alternative to prosecution as yet she is still very much reluctant but I am breaking her and also now have enough pictures of her that she will not want sending to her old friends!!
I do hope you find this interesting although in many ways different to your normal correspondence.
Thank you for your letter Edward. I found your account very interesting and it brings to light that not all sissy training is female led though obviously that seems to be the norm. In today's world of gender fluidity and conventional roles being dynamic I see no reason why a male could not be involved in convincing the submissive male to live the productive life of sissymaid. Your aunt's treatment of your uncle Frank was a major influence on you and for the better for everyone concerned.