from Ruth

Dear Helga,

I just love your web site! About 4 years ago I was charged with taking care of my little step-brother while my (widowed) mother was away for several months. Michael is Caucasian, brought into their marriage by my white step father and grew up with my mother, sister and I who are black. At the time Michael was 16, my sister was 18 and I was 21. Mother wanted me to take charge of him while she was away; fearing that he'd get into some serious trouble is left unsupervised. Though it was not convenient for me, I agreed as long she would give all the necessary authority.

Less than a week later I caught him in my room, naked and masturbating while holding some of my under things. I was so angry that I instinctively pulled my naked brother over my lap and spanked him for all I was worth. I noticed an immediate change in his attitude whenever I was around but he still managed to get himself into trouble at school.

After a couple of weeks I devised a plan to insure his behavior, at all times. First deciding to incorporate a Chastity device, I purchased one on the internet. And knowing that I might need some help, I asked my sister if she would come home for a weekend from school to help me. She was so amused when I told her of my plan and quickly agreed to help. On the appointed day, I slipped a sedative into his dinner time drink and he got so tired that he went to bed at 8pm. At 9:30 my sister and I crept into his room and tied him spread eagled to his bed. He was quite groggy and didn't have much fight in him so I was able to fit his genitals with the chastity device without much trouble. We left him tied to the bed until morning.

At 6am we were awakened by his yelling. I just knocked on his door and told him to be quiet and if he wanted to be let go he'd be patient and wait for us. My sister and I smiled at each other while we went downstairs to have coffee and breakfast. More than an hour later we returned to his room. I pulled back the covers and discovered he had wet himself during this night. Michael was mortified at his condition of being naked in front of his sisters with wet sheets. I told him, in no uncertain terms that he could shower and get dressed but that he was never to attempt to escape the chastity device and that I would be inspecting it daily to make sure he was not tampering with it. I held up one of my old bras and panties and told him that these were his clothes for the day. He had 30 minutes to shower and present himself to us in the living room.

It was over an hour before he sheepishly came down the stairs. My sister Jan and I both snapped a couple of photos as he ran back up the stairs into his room. I followed and told him, through the door, that he'd better cooperate or there would be a much higher price to pay. I slipped a sheet of paper under the door which had the names of his friends and teachers on it and told him that I would inform everyone on that list of his perverted behavior and send them one of the pictures we had just taken. 'You've got one more minute mister.' And I went back to my seat in the living room. Several minutes later he once again descended the stairs. 'I am done fighting with you young man. You will do as you are told, with no questions asked, or everyone will know what a filthy pervert you are. I want my orders carried out, to the letter, understand? You were late at every turn this morning and that is not acceptable. Another spanking is in order so you can just march yourself over to the dining room table and lay across it, now!' I said very sternly. Michael meekly lay across the table and Jan and I secured him there at both wrists and ankles. I proceeded to spank his bottom for several minutes until he was nice and red. 'Are you going to cooperate now young man?' When he started to protest I gave him another 20 on his sore bottom and he finally agreed. 'You are going to start doing chores around here Michael. In fact, you are going to do all the chores.' I first had him put his wet sheets in the washer then clean up the kitchen. He tearfully complied with all the shame and embarrassment I had intended.

Jan had continued to take more photos of him, getting spanked and washing dishes and now went to my room to print some of them on my computer. She made some nice 8 x 10's which we framed and placed around the house as a reminder of his naughty behavior and to the threat of his dirty little secrets being exposed to others.

About 3 o'clock that afternoon I had him take another shower. Jan and I then dressed him an old pink ballet outfit. We used a curling iron to do his hair and put a thick coat on makeup on him. We finished him off with a pair of tights and 4 inch heels. Then we spent the rest of that evening and the next day having him practice becoming more feminine. We walked him with a book on his head, taught him how to speak softly in a little higher pitched voice, curtsy and on and on.

It may surprise you to know that I had no problems with Mother when I informed her on the phone. I first told her that I was spanking him because I caught him playing with my underwear while masturbating. Then I told her that I was going to, 'fight fire with fire' by making him dress up in girls clothing. 'He's a changed boy Mother.' I told her. At first her attitude was that she didn't really care what I was doing because she didn't have to worry about him getting into trouble anymore. But once she got home and saw his transformation she was delighted and only encouraged me to continue.

Anyway, that was four years ago and since then I have escalated his punishment and training and he now serves us, full time, in a lovely PVC maids uniform. I inspect him and give him a discipline spanking daily. He has been transformed into our lovely little maid we now call, Penelope. He has been in his chastity for all four years and for the last two, has not worn any male clothing whatsoever. He serves, not only the 3 of us, but a group of our close friends as well. We lend him out on occasion to clean or serve at our friends homes for special occasions. I continue to look for more ways to further feminize Penelope and do not have any plans to allow him another orgasm.


Thank you for your letter Ruth. I'm sure your mother must be very proud of how you took charge of your step brother, a good dose os strict petticoating can turn even the most troublesome boys into good girls, or even maids.


Return to Index
Letter 5