I would be delighted to establish personal contact with any females or couple who find this story of particular interest...
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. Crofton as she introduced her daughter to the group.
“I’m nine,” said the little girl, who for reasons I also did not know, was no happier to be present under these circumstances than I was.
“Now Bernard,” said my Aunt, who never adopted the conceit of giving me a feminine name---she thought it was more humiliating to make certain that everyone knew I was a boy, “Bernard put those tea things away and come over here and say hello properly to little Jessica.”
I knew better than to disobey to even the slightest degree. So blushing terribly because of my attire, I went up to Jessica, who was standing in the center of the room, and curtsied nicely to her.
“That was very pretty Bernard,” said my aunt, “But you know we need to make sure that Jessica fully understands that you are really a boy and not a girl, and that you are dressed as a little girl as punishment because you’ve been bad. So pull down your panties to below your knees and pull up your dress so Jessica can see the proof that you’re a boy.”
Jessica looked startled. My face turned to even a deeper red. I couldn’t help myself. I knew there was nothing I could do. I must obey. I began to cry.
There was a momentary hush among the other half dozen women present, but then there were a few giggles. “Oh yes,” said one of the older women, “Come on Bernard, show us all that you’re really a boy!” And then everyone began to laugh out loud.
With tears streaming down my face, I reached under my dress, hooked my fingers into the elastic top of my lacy pink panties, and pulled them all the way down. I stood up again. Then still facing the little girl Jessica, I lifted my skirt and pulled it up to my neck. There I was in all my nakedness for everyone to see. And to make matters even worse, I had a huge erection sticking straight out and up a little bit.
“Well, look at that,” said one of the women, and everyone started laughing again. Everyone, that is, except Jessica. I think she knew what was coming next.
“Now Jessie,” her mother said. “You know full well that Bernard here is not the only naughty child in this room, don’t you?”
“Yes, Mummie,” the little girl said.
“And you know that you are being punished too, don’t you?”
At this, the little girl began to cry.
“So suppose you do what we’ve been practicing at home,” said her mother, “You turn around and bend over, and pull up your dress so Bernard can have a good look at you just as you’ve been having a good look at him.”
Tearfully, the little girl did just as her mother told her, and what a surprise there was for me. Because when Jessica pulled up her dress, it turned out she wasn’t wearing any panties at all! It also turned out that she had a very red bare behind to expose to me and to everyone else in the room! It was obvious that her fanny had been thoroughly spanked!
“Now grab your cheeks and pull them apart so that Bernard can have a really good look at all your private parts.” There was more whimpering, but little Jessica did as her mother said. There was another hushed silence in the room. Then my Aunt Emmaline took over.
“Bernard,” she said, “Stick out your tongue!”
“You heard me,” said Aunt Emmaline. “Stick out your tongue. And next I am going to clap my hands. And when I clap, I want you to grab onto Jessica’s legs and shove your tongue up into her hiney hole. Shove you tongue up there as far as you can and lick it! Lick it! Do you understand? And keep licking until I clap my hands again!”
Well Jessica and I were both crying now but we were also both doing just as we were told, and I have to tell you, I don’t think it was the most terrible thing in the world for either of us. I got a good look at some female parts I’d never seen before, and Jessica was getting hot even though she was only nine. Her mother came over and took hold of one of her hands and put it up against her cunny and made her rub it while I was licking her hiney hole. I don’t know how long we were like that but it was a good long time before my aunt clapped her hands again.
“There’s just one little thing wrong with this scene,” said my Aunt. “Bernard, you need to have a bottom that’s just as red as Jessica’s. And I believe your Mom is ready to do the honors!”
My mother grinned, reached into her purse and pulled out a big leather strap.
“Alright,” said my aunt, “both of you children strip naked now! Take off everything. Even your shoes!” Jessica you go stand against the wall over there and spread your bottom cheeks so everyone can see everything. Bernard, go over and lie across your mother’s knees.”
My mother started off my spanking with a resounding Whap!” There were two dozen more strokes before I was allowed to join Jessica against the wall. I also had to pull my cheeks apart to put everything on view for all of the ladies present.
We stayed like that for the rest of the afternoon while the tea party proceeded as if we weren’t there. The party broke up about 5 p-m. Jessica was allowed to put her dress and her shoes back on and went home with her mother. I was sent upstairs to don my nightie and sent to bed horribly early and without any dinner. In case you are wondering whether I played with myself after all that had transpired, I did. All night long until I couldn’t any more.
This turned out to be more than an isolated incident. In fact, this was very much the way things went on my punishment weekends for the rest of my 13th year. Jessica was far from being the only little girl involved. Sometimes there were three or four of them in one afternoon, pulling up their dresses and sticking their bottoms into my upturned face for a proper hiney hole licking. Jessica was the youngest but they ranged in age all the way up to 15. Not all of them were there for discipline. After a while it became clear that some of the girls actually liked it, and I can’t say that I totally disliked the procedure myself.
Except for one time with the 15-year-old, a buxom blonde named Mary Ann, that I will not forget. Mary Ann had said on a number of occasions that as much as she enjoyed having my tongue up her hiney, she would like it better if she wasn’t absolutely clean back there. I didn’t think about this much because, to tell the truth, I couldn’t stand to think about it. But one day she matched actions to her words.
When Mary Ann bent over and pulled up her dress on that one afternoon, it was obvious that she had just gone to the toilet and made pooh pooh before coming over, and that she had deliberately not cleaned herself off. Her behind was a brown mess and combined with the smell it was clear to everyone just what was going on. I turned to my Aunt with a look of appeal on my face but it was quickly obvious that I was not only not getting off the hook, it was going to be made even worse.
“Bernard!” said my Aunt, “Don’t bother to crouch. Just lie down on your back. But make sure you keep your tongue out and when I clap my hands, start licking the best you can until I let you to stop.”
I did as I was told and Mary Ann stooped down over me, shoving her fat naked poo-poo covered behind right in my face. I licked and I licked but I wasn’t allowed to stop until everything, and I mean everything, was licked clean. When she finally got up, my dress was badly stained. I had to take off everything and with everyone following, including a couple of younger girls, I was made to go completely naked into the laundry room and put my dress in the washing machine. Then I had to go back into the living room and even though there were no signs of any pooh pooh stains on the rug I had to lick the entire area with my tongue until my Aunt was satisfied. Was I then allowed to go upstairs for my early bedtime?
“Not quite yet,” said my Aunt. “We all know what you do up there when you are by yourself,” she said, “so today you can just do it right here in front of all of us before going beddy by.”
So I had to stand there naked in front of everyone and grab my penis and masturbate while they all cheered me on. When I finished I had to get down on all fours and lick up my own cum before I was finally allowed to go upstairs.
So how did all this end? Well I’m in my thirties now, and I’ve never married. But Mary Ann comes over every weekend, and you can imagine what happens. Some times she brings my Aunt Emmaline with her. Emmaline is old now and confined to a wheelchair. But even from that position, she can still wield a nasty leather thong.