My mother died from complications giving birth to my brother Sam when I was only 8 years old. The doctors managed to save my brother. My grandmother came to stay and look after us so my father could return to work. Gran was strict but fair and we had a pleasant childhood until I was around 17 and my Sam was 15, he then went off the rails and was continually in trouble at school eventually getting excluded. Gran struggled to find a school that would accept him for his final year and employed a tutor who could not cope with Sam's wayward behaviour and departed after only a couple of months. At this time father was called home and there were heated conversations between him and Gran. Another tutor was employed and father returned to work.
Sam's behaviour did not improve and then the police called one evening and broke the news that father had been killed in a drunken brawl. Over the next few months Sam's attitude towards myself and Gran became unbearable and the tutor again left. Sam then thought he could lounge about and go drinking, he became violent towards Gran, which I could not stand, so I attempted to intervene and ended up with a black eye for my trouble. Sam disappeared upstairs then we heard the door slam as he went off for another bout of drinking. When I went to bed later I found that Sam had been in my room and destroyed most of my dresses and some of my college work. That was the end as far as Gran was concerned and she stopped Sam's allowance and told him he had to find a job to pay his way, he responded by lounging around the house and treating us like dirt.
A few weeks later I came home to an empty house and a note from Gran saying she would be back and explain later. When she returned she told me that Sam had been arrested for violent theft and to get bail he had to reside at a fixed address so she had given her younger sister's address and taken Sam straight there. I questioned whether Gran's sister would be able to cope with Sam and she said yes with a bit of a smile. After a few weeks Sam went to court and was lucky to get away with a suspended sentence after Gran's sister spoke at court and gave assurances that his behaviour was much improved and she would guarantee it stayed that way.
I asked Gran about Sam several times over the next year and was simply told that he was working hard and could not get into trouble, again with a smile. I became more curious and after badgering she said we would go and visit him at the weekend. On Saturday morning we drove to Brighton where Gran told me her sister ran a guest house. When we arrived Gran told me to prepare for a shock. She rang the doorbell and I nearly fainted from the shock as the door was opened by Sam dressed in a maid's uniform, he was obviously just as shocked as me to see us on the doorstep and forgot to invite us in which earned him some sharp words from Gran. When we had all regained our composure a very flustered Sam showed us into the lounge where Gran's sister was sitting, then left the room with a curtsy.
Over the next hour, with the maid (Sam) being regularly summoned for tea and cakes etc, I was told the whole story. Gran's sister ran a guest house for transvestites and cross dressers. When she took Sam under her wing she laid down the law straight away. Sam had tried to rebel but with him getting no food and being locked in his room he soon began to comply. He only had the clothes he wore at court all the rest were burnt by two of Gran's sister's clients while they were at the court. After 12 hours of being locked in his room with no food he begged to be allowed to come downstairs and get some food which he was allowed to do on the promise that he would do exactly what he was told by anyone in the house.
When he came down into the kitchen gran's sister and her two cross dressing clients were waiting for him with a maids dress and apron. After much protesting and tears he ended up wearing the uniform and was allowed to eat while the others watched and explained that he would would be fully trained as a maid. He would be dressed this way at all times and he would earn meagre wages which would be paid into an account which he would have no access to until he was deemed to be a responsible adult. I must admit that the more I heard the more I was getting turned on and I soon cottoned on to the fact that whenever I asked a question Sam was summoned to explain. I couldn't resist asking about Sam's undergarments and he was called and had to lift his dress and petticoat to show us the frilly nickers he wore. I asked whether he had to wear a wig but was told that Gran's sister insisted that he remained what was obviously a boy in girl's clothes.
I have made regular visits to stay at the guest house and have Sam wait on me hand and foot. I am now dating one of the cross dressers that helped in Sam's training whose name is Robert. I sometimes have him come to stay with me and Gran and dress him similar to Sam so that he can serve us. Life is finally good for me but no one can say how long Sam will be in training although I get the impression this could be his life for the long term.
Sorry if this has gone on too long but I felt it needed to be explained in detail.
Thank you so much for writing with your delightful story Jenny, of course Sam, like so many bad boys, deserved everything thing that has and is happening to him. Congratulations on finding a suitable male yourself, I have no doubt you know how to handle him.