Aunt Emmaline

My Aunt Emmaline practiced petticoat discipline on me from the time I was eleven years old, which meant at age 13 I was quite used to being dropped off at her house by my mother on a Saturday morning to spend what we called a punishment weekend. That meant I had to take off my boy’s clothes the moment I arrived, stand completely naked before my aunt, and let her dress me as a girl. My dress for the entire weekend was nothing more than a light cotton little girl’s frock, pink or white lace panties, and some shiny Mary Jane shoes, all of which my aunt insisted on putting on me herself.

Aunt Emmaline was a rather handsome woman in her fifties who always wore her hair in a tight bun and dressed in severe tweeds and “sensible” shoes. She had been married and divorced within just a few weeks when she was in her early twenties and had an abiding dislike for the male sex. She seemed to especially enjoy hurting and humiliating young boys and I was the regular recipient of her attentions in this direction.

I was fortunate in that, because she lived at the other end of town, none of my school friends knew about my punishment. This did not mean, however, that my “little girl” attire and the bare bottomed spankings to which I was regularly subjected on my weekends with my aunt were entirely unknown to the rest of the world. Aunt Emmaline had a circle of lady friends who were regularly invited over to witness and, often participate, in my discipline. And because these sessions were often photographed by my aunt or by her friends with me either curtseying in little girl attire, or holding up my dress with my panties around my ankles, or bent over naked with my bruised bottom exposed after a paddling, there was always the threat that even more people would find out about my predicament.

These “blackmail” photos served as a powerful argument against my objecting to any additional humiliations that my Aunt wished me to undergo. And there were more than a few. Quite often on these afternoons when the ladies were visiting I would be passed from lap to lap. I would be cooed at in baby talk and even occasionally made to suck on a baby bottle. Some of the women liked to put their hands under my dress while they were holding me and grab and squeeze my penis and my testicles. Sometimes they even masturbated me. Then when I came I was forced to strip naked for a spanking before putting on a fresh set of little girl’s clothes.

Often these friends of Aunt Emmaline were many years younger than she, which meant that if they had children of their own, they would be too young to be brought along to witness my humiliation, but this was not always to be the case. By the time I was 13, a number of her friends had little boys and girls who could, if my aunt and their parents so wished, play a role in my degradation and might even be in for some chastisement themselves. It never occurred to me that such things were actually under discussion when I wasn’t around. I later learned that even my mother had been called in, and had not only laughingly offered her approval, but let my aunt know she wanted to be personally on hand for the particular new revelries at my expense that were planned.



And so it happened that one Saturday, while I was engaged in serving tea and cookies to Aunt Emmaline and her friends, and, for some reason I did not know, my mother was present as well, the doorbell rang and who should appear but a neighbor named Mabel Crofton, accompanied by her daughter, Jessica, a freckle faced somewhat skinny little girl with bright red hair tied in pigtails.

“How old are you Jessica?” asked Mrs.