When Anthony arrived for his appointment with the wardrobe mistress to be fitted for additional punishment clothes, he was surprised to see a girl just slightly older than he. Her presence – a teen girl seeing him in his kilted, feminized condition — made him more nervous and self-conscious than being seen by the other boys; he was getting used to the boys ragging on him! Ms. Gilbert explained as she introduced him that the girl was her daughter, a junior currently attending St. Gertrude's, the girls' school across the river. She had conferred with Hillman and they thought it was a good idea to give Anthony a taste of what it would be like if he was ever sentenced to the St. Gertrude's Academy for one or more days. She said the girls were notorious terrors when it came to dealing with sissy boys, and they were going to give him a little sample of such treatment as a deterrent to earning for himself such a punishment.

The now terrified and confused boy thought about running out of there, but before the thought barely registered in his mind, mother and daughter had his legs bound and were hoisting him up by his bound hands. Rose, was the daughter's name, and no sooner had he been trussed up when she began taunting and teasing him as she bent down low and began peeking under his kilt.

"Oh, he has a nice white slip on under there, and what's this I see? I think I see girlie pink panties! Imagine that! Pink panties on a boy! What kind of fairy boys are they raising here at St. John's,” she screeched and then followed with a deep and hearty laugh. The type of laugh girls can spurt out that can instantly kill the masculinity of any man or boy.

Of course, Rose wasn't satisfied with just peeking and staring directly into his down-turned eyes as she reached up under his skirt and felt his panties. She snapped his leg elastics and made his thighs sting. She stroked the smooth nylon over his bottom and told him even her own panties weren't that soft and smooth and Hillman must have spend a fair amount of the school's money supplying him with such expensive panties. She teased him by asking if she could borrow some of his panties sometime; she envied having such luxurious panties like he was lucky enough to wear. She then wasted no time and went directly for his penis. She expertly stroked it up into a firm erection that made him huff and puff and squirm, and once he was wild with pleasure, she introduced pain, savagely pinching his dickie. Then she switched back and tenderly stroked him to hardness again only to pinch it again. Repeatedly she did it, and as she did, she kept up a running dialogue, telling him he was a sissy, a fairy and every other faggoty name she could think up.