Dear Auntie Helga,
I have been a closet transvestite for many years. I am retired now and married to a wonderful lady called Frances and we enjoyed a very happy sex life until a couple of years ago when her disability made it impossible. My wife's best friend - let's call her Joyce - is a divorcee and lives nearby. We keep each others' keys in case of emergency. Joyce is a very attractive lady and always dresses very smartly in some beautiful dresses and skirts.
Okay, you've guessed it. I started going round to her house in the daytime while she was at work, wearing all her lovely clothes including her undies. I discovered we were the same size - 16.
Inevitably, disaster happened. She came home early one day while I was prancing around in one of her pretty dresses. There was nowhere to hide! I ran upstairs to her bedroom hoping she would just pop in downstairs and then leave again. But she came upstairs and found me sitting and cringing on her bed. Oh dear, Joyce went berserk. She laid into me, shouting at me, hitting me with a coat hanger and calling me a disgusting pervert. She seemed to be getting a lot more enjoyment than she should have from thrashing me. Then she told me to get out of her clothes and went downstairs to wait for me there.
Eventually, I crept downstairs and tried to apologise but she was having none of it. She ordered me out of her house and said she would be telling my wife what I had done.
True to her word, she did tell Frances who was shocked and not too pleased about my 'perversion' and unknown to me, they got together to discuss how I should be punished. The upshot was that I was to be called Sylvia from then on and they bought me a French Maids dress and knickers to wear. Joyce would come round once a week and I would have to wait on them. She insisted that I call her Madam in future. If I got something wrong or spoke out of turn, Joyce would make me kneel in the corner or cane me for more serious offences. Frances would never cane me but she did nothing to stop Joyce.
Even worse, I had to spend two evenings a week and most weekends at Joyce's house, cleaning, scrubbing floors, and washing her smalls and any other chores she could think up for me. There was always something I would be punished for and I was caned regularly, to her great delight. Sometimes she would invite friends in and I would always be abused and belittled by them as they teased me relentlessly.
One day, Joyce said I had to go back to basics to learn how to behave properly. This meant having to wear a nappy and baby's bonnet and have a dummy stuck in my mouth. Joyce would sit me on her lap while she sang baby songs to me while her hands wandered in places they shouldn't have. I didn't mind the French Maid's outfit so much but I hated the baby clothes. Joyce was well aware of this and gloated over my misery while dressed as a baby.
But recently, she has become more forward. For instance, when she dresses me in baby clothes, she keeps kissing me on the lips and telling me what a beautiful baby girl I am. Another recent change is that sometimes, she allows me to wear proper dresses which at first, I was very happy about, but then she started calling me her lesbian friend.
Now, Joyce has given me an ultimatum. She wants me to become her lover or she will tell all our neighbours about my 'perversion.' Even worse, Frances knows nothing of this. Joyce has gone behind her back.
Oh Auntie Helga, help!! Joyce wants to have total domination over me. If I don't do what she wants, all my friends and neighbours will find out about me. I just couldn't stand the shame. But on the other hand, I'm terrified of becoming her sex slave and having to obey her every command.
What can I do? Please help me Auntie Helga.
Thank you for your letter Sylvia. So sorry to hear about your situation, a situation I might add brought on by your own lust and disgusting behaviour. Your dear wife had to suffer the humiliation of this discovery and was, in my opinion, quite generous in allowing you to remain as her maid.
Now you want out and are afraid to serve Joyce sexually, please, this is an opportunity to make amends and bring some pleasure to a friend. I just don't see a problem here and feel you should do as your told and get on with it.