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Status: In Progress  |  Genre: General Erotica  |  House: The Humiliation Board

Poor jenny suffers even more at the hands of her legal guardian. He points out her reluctance to participate in his "education process," and considers her punishment.






(This story is a fantasy. The author does not condone any of the behavior described herein. It is terribly politically incorrect and meant for fantasy pleasure only.)



Jenny, this is the first of your progress reports.  I hope you have thus far enjoyed your stay with us. By now of course, you realize that we have only your welfare at heart, and although we may seem somewhat strict at times, it is for your own good. I do wish that this progress report could be more glowing, but we feel that you have taken to some of the new rules in your life with less enthusiasm than necessary. So, before we move on to new rules and practices, we need to review the old ones and your lack of accomplishment.


A word about punishments. Thus far, you have had to experience spanking on your tits and cuntal pad.  I assure you, we do not enjoy doing this, and are forced to such extreme behavior by your lack of mastery of the rules. For example, although I know you are not used to being naked at all times at home, especially with four men in the house, but that is no excuse for keeping your hands covering what you call your private parts. For good girls, there are no such thing as private parts. You must realize that a girl’s parts belong to which man she serves. In this case, it is to me, your legal guardian, my two associates, my manservant, and your wonderful new boyfriend. Also of course, to any of your boyfriend’s buddies.

You are never ever to cover yourself with your hands, or by keeping your body bent over or collapsed in any way. Good girls are proud of their bodies. You have been instructed to keep your legs spread and your tits thrust out at all times. You have also been instructed to keep your nipples hard. In this instance, you have continually disappointed us, maintain that it is painful and too difficult to keep your nipples hard at all times.


To rectify this defiance on your part, we are going to institute nipple whipping. If we ever find your nipples not erect, your nipples will be whipped quite harshly with a leather riding crop.  Again, this is for your own good. We want you to be a perfect young lady in every way.  If you do not sit or crawl with your legs properly spread to show you pretty, young cunt, You will have your cunt lips whipped in the same way. We were all delighted to discover during your physical exam, that you do not yet have any hair on your pudenda. When some starts to grow there, it must be removed at once. A good girl’s body is totally hairless for her man or men.


Speaking of your breasts. Another error in your performance was that you have been instructed to swing your tits when crawling, walking or dancing for us. Men like nice big round titties that wobble.  I must say, your boyfriend was particularly disappointed in your tits. He says they are hardly a handful and almost impossible to titty-fuck. On your behalf, I explained to him that you are still young and growing. Also, that you are quite petite of body. But he insists that he deserves a girlfriend with nice big tits, and I am afraid we agree.


Therefore, next week, we are taking you in for breast enhancement surgery. Don’t worry my dear, the whole thing takes only a day or so, and they go in through the belly button, so there are no unsightly scars. After considering the size and shape of breasts on offer, and talking about how a size D might look on your tiny young body, we decided instead on a double D, so you can actually grow into your tits. They may be difficult to handle and quite heavy at first, but we are sure you will adjust, and it will certainly help you with sticking them out for your gentlemen. There is some pain involved as the skin has to stretch considerably. Fortunately you already have nice big nipples, although some shots in them, might also make them larger and more sensitive.


Now on to more serious matters. We have all been seriously disappointed with your cocksucking. I understand you come from a totally isolated background where you never even heard of such activities, but you are no longer a child. You are a big girl now and must learn to behave like a young lady. First, you don’t show nearly enough enthusiasm when presented with a dick. Your new boyfriend says you don’t kiss or lick his cock with nearly enough affection when he presents it to you. I have noticed the same thing, especially when the penis and balls are a bit sweaty. I spent four hours patiently teaching you how to lick a man’s testicles, how to lift the nuts on your tongue, suck the ball hairs and bathe the scrotal sack with your spit. And yet when you perform the task, your licking is lackluster, almost as if you are not enjoying it. As a good girl, this is one of our primary tasks in life. You will sometimes be licking up to twenty cocks and balls in a single day, young lady, and you need to learn how to accomplish this simple task. You must learn how to love the taste of pre-fuck and cum. I know it takes a bit of time to get used to the flavor, but I have been patient with you. Just as, when you are young, certain salad dressings may taste too strong, cum may at first seem a bit slimy or pasty. It is an acquired taste for a girl. We have given you at least five loads of cum every day, trying to get you used to the taste. We have mixed it with your food and drink. Now, the rest of the work is up to you.


And then there is the matter of gagging on your boyfriend’s cock.

We intentionally picked a boyfriend for you with a huge cock, to please you. AND THIS IS THE THANKS WE GET?’ Do you know what an insult it is to a boy to have a girl gag on his dick?  Of course, he wants to fuck it down your throat, but instead of being proud and happy, you cry and make a fuss. How do you think that makes him feel?  No wonder he slapped you with his dick. You have not made a very good impression on your boyfriend. The same is true for when he wanted to spit on your face and in your mouth. He says you made a disgusted face and cried. This is a loving gesture than most boys want to do with their girlfriends. A nice special spit wash facial.  Perhaps it was a mistake to keep you isolated from boys for so long. Most normal girls know how to please a boy before they even reach their teen years. They have at least read about it on the internet.


In the last four days, you have sucked your boyfriend ten times, and you have sucked the dicks of eight of his best friends.  Plus, sucking my dick and the dicks of my associates. You should have learned something, not continued to act like some stupid ignorant cunt!


And we have not even broached the subject of fucking yet. Your boyfriend is getting impatient. Most boys demand that their gf’s allow them to fuck them by the third date. It is just the way things are done. Date, one, she masturbates the boy, date two, she sucks him off, date three he fucks her and date four he fucks her in the ass. And then, if he deems her worthy, he might start to date her regularly or even go steady. This is how it is done in America.


Tell me, Jenny, how can we move on to fucking, when you don’t even suck worth shit. The only answer we can think of is to have you suck a whole lot more dick. So from now on, you will be sucking twenty-five dicks a day for at least the next two weeks. And we will only move on when you have conquered that.


Another strike against you. You boyfriend told us that he wanted to watch you shit and piss, and you refused, saying you were too shy! Just because six of his buddies were with him, what in God’s name were you thinking?  You are not allowed to question your boyfriend’s requests. That is not a girl’s right. We make you shit and piss with us watching you, why should your boyfriend be any different? Or his buddies for that matter?  Yes, they wanted to take pictures and send them to their friends. Why shouldn’t they?  We are so disappointed in you.

To correct that, we have asked your new boyfriend to invite twenty or thirty of his friends from his former stay in prison, to watch a performance of you shitting and pissing on a clear plastic toilet set on a stage. You will also be required to masturbate for them.  And you will suck your boyfriend’s dick in front of them to show your love for him. I hate these extreme measures, but they are necessary to help you.


We have also examined your dress for public, and find that your crop top tee shirts first of all are not cropped high enough. Two inches of tit swell should show

At the bottom. This will improve with your tit implants. Then, the material of the tee shirts has proven to be too thick. That is not your fault, but ours. We apologize for that. The new material will be much thinner and translucent, so that your pretty and we hope erect nipples will clearly show through. Also your skirt will be adjusted to that the lower hem in front hangs one half inch from the bottom of your cunt. In the rear, the hem will be adjusted so that six inches of  your ass swell shows  beneath. This is what you will wear to malls, sporting events, restaurants, and all public places.


We have to begin to think about getting you fucked. You boyfriend has a dick that is not only very very long but enormously thick, as you realize from trying to suck him. It will take some work to get that fucker in your holes. We will therefore begin daily sessions with cuntal and anal dildos.  To help us with these exercises, we have invited a group of teenage boys who, in an on-line survey, said they are interested in medical careers.  Therefore, any shyness you still have about  being naked, will simply have to be gotten rid of, as these boys will have total access to both your pussy and asshole.


Lastly, you are not getting wet down there nearly enough to please us. We have asked you to play with yourself every spare moment you have. You seem reluctant to masturbate in front of us. We hope your public performance helps solve that. Also to help, from now on, whenever myself or one of my associates or my manservant is in the room, you will vigorously finger your cunt. If you do not do it with enough vigor, you will be punished. To help you learn about your pleasure zones, you will at these times, also finger your asshole, inserting at least two fingers in to the second knuckle. You will keep this up until told to stop.


After lunch, we will talk more about your enemas. Your boyfriend and some of his friends have asked if they might watch these, and I see no reason they should not. I expect to see cocksucking improvement starting with your boyfriend tonight. To prepare you, you may practice on me now.

Submitted: July 22, 2021

© Copyright 2021 dale10. All rights reserved.

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