Letter 7
DEBBIE'S NAUGHTY BOY BECOMES A DARLING LITTLE SISSY
From Debbie
See 'Advice from Nanny Susan' September 2000

Dear Susan,

I want to thank you for my sought-after advice, which you gave me in this month's 'Advice' page concerning my brattish son. We talked at length  (my husband and I) and decided to go for it. When he came home from school that Friday, we had everything ready. We decided to go all the way at first, and then use lesser degrees of petticoating as a bargaining chip. We put him, after a good spanking, in a little gingham dress, with cotton pettis, and a pinafore over the top, with little lace anklets, black Mary Janes, nylon panties and a camisole top.

He was almost ill with fright, but we explained this was for his own good, and that he was going to be dressed like this, or in similar things, for a long time to come - at least until he learned to act like a gentelman, and not run around and worry us to death. We told him he had to wear the dress the rest of the day, and if he was very good tomorrow he could wear girls' shorts or pants instead of a dress. This seemed to ease some of the shock. I also told him he would wear girls' panties under his school clothes and if he didn't act 100 percent like a gentleman we would add sissy things to his school outfit (lace anklets, shoes etc).

Susan, in the first week we saw quite a change! We have him change into girls' clothes when he gets home, and he stays in then until bed time, where he also wears a  nightie.  We went to my brother's the next weekend, and he begged me not to make him wear his girls' things. I told him I would decide, but he would definitely be wearing something sweet and pretty. He was beside himself with worry, whilst I was leaning towards little bibbed overalls with a white cotton blouse, plain nylon anklets and white girls' tennis shoes. His cousins, especially the ballet dancer, were going to be quite amused.

When the day came, the visIt went terrifically well, I don't think our little darling will ever be able to tease his cousin again. I dressed him in a pink bib shortall with a white girls' oxford blouse with little pink flowers around the collar, and cuffs, white nylon anklets with one row of lace on the roll down, and pink little girl Keds tennis sneakers.

Susan he was so mortified at being seen like this he cried all the way there, which added to his embarrassment, having red eyes like a cry baby. I made him paint his nails a clear coat, and put on clear lip gloss to give him a girlish glow. I didn't get a teddy bear, but did have him carry a little lion, one he used to love when he was a toddler. When we walked in you could have heard a pin drop. My brother could hardly contain himself, and my sister in law just giggled like a schoolgirl. He started to cry again and I slapped his hands, which reduced the tears to little sobs.

When his cousins came downstairs they had no mercy on him, giggling and pointing at him, my little nephew (the dancer) said he looks so sweet dressed that way, and sooo much nicer, then he asked me if he liked to dress like a girl now, and how did he change? This brought on another fit of tears, to the joy of my niece and nephew. He spent the entire afternoon sitting beside me with his head bowed, and being as quiet as a little doll. His cousins left him alone after about an hour of teasing, and bringing him to tears several more times.
When it came time to leave I made him kiss his cousins goodbye on the cheeks (in little girl fashion) like I remembered his sister doing when she would say goodbye. This of course brought on more laughter from his cousins, and my brother and sister in law. As we turned to leave my little niece asked me (this is precious!) if he was going to be a girl now; this was more than he could stand and he ran crying from the house to our car. I told her no, but he would be sweeter and nicer from now on.

He cried and sobbed all the way home. I started to feel sorry for him, but I remembered his old self and immediately had second thoughts. When we got home at around 6.30 I had him change and put his flannel night gown on, eat a bowl of soup and go straight to bed.

My husband and I are so pleased at the change this has made. Thank you so much. I'll keep you posted on his development, and please continue to write me with suggestions.
Love sincerely,

Debbie

He must have looked very sweet, and a very different boy from his former rude and difficult self. It looks like 'Petticoat Discipline Monthly' has made another conquest, and I am sure that Debbie is brimming with ideas after reading all the back issues of the magazine. Perhaps when he meets his cousins in the future, wearing a pretty dress with a snow-white cloud of petticoats underneath, he can be taught to curtsey by Debbie's little niece.
Susan

Return to Main Page