Stripping Humiliation Stories
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A collection of sissy humiliation stories I've read and liked, with strong emphasis on dominant males and submissive boys or sissies.
Christian’s School of Humility 2: The Awakening
June 5, 2016
Janice swallows hard and then kneels down in front of her teacher. She makes sure she doesn’t bend over too far. The last thing she wants is for the back of her skirt to raise up too high. She has white cotton panties on under her short tartan skirt, so they would probably only notice her plug. That would still be horrifying.
Her hands tremble as she reaches up and pulls her teacher’s cock out.
This story takes over where “Christian School of Humility” left off.
In that first story a 13-year-old boy named Jack gets a job at the school as a janitor. The private school’s curriculum involves a lot of sexual activities with the students. Needless to say, Jack loves his new job.
Unfortunately, he makes the mistake of sneaking in to an off limits area. There he discovers that not all the students at the school are actual girls. Some are boys dressed like girls. They catch Jack spying and as punishment they decide to make him a student as well. Or was this their plan all along?
Bill, Jack’s father and the headmaster at the school, not only gives them permission to turn his son into a sissy but participates in the training as well.
By the end of Christian School of Humility Jack is well on his way to becoming a very obedient and well trained sissy.
Eight months. Had I known they were going to keep me locked up in here this long I probably would have killed myself the first week. Okay, I guess it isn’t so bad here now. However, I remember how bad it seemed back then.
Being turned into a sissy seemed horrible back then. Granted, I was barely 13 at the time. Not that I’m 14 yet. The really strange thing is that now I almost welcome the transformation. I barely even remember my old name, ‘Jack’. Now I just think of myself as ‘Janice’.
Sure, there are moments here and there where I miss being Jack. There are also many times when I still feel ashamed and embarrassed when having sex with men. I don’t feel I’m gay… not really. Yet, I’ve had gay sex so many times that it kind of seems natural now. Just like dressing up like a girl seems natural.
All of that said, if I had a choice I would probably choose to be Jack again. Provided of course that I would no longer have to have sex with men. While having sex with men doesn’t bother me as much as it used too, I very seldom actually enjoy it. It is normally just a task that needs to be performed… kind of like brushing your teeth.
Having sex with girls, however, is still very enjoyable for me. Not that I really get to do any of that. Casey, one of my trainers, is female. However, I never get to actually fuck her. If I’m a good girl then sometimes she will let me use my tongue on her as a reward. It isn’t much but it still reminds me sometimes of what it was like to be a real boy. It is supposed to be a reward but normally I end up crying for an hour or two afterward.
The closest thing I actually get to fucking a girl is when they have me play with other sissies. For a few months I even had a sissy ‘girlfriend’ named Danielle. I guess technically she is still my girlfriend. However, for the past five months I have only gotten to see her a few times.
They say that absence makes the heart grow fonder. That was true with Danielle for the first few weeks we were separated. However, during that time I started thinking about her role in my training. I want to believe that she really loves me but deep down I know her only role was to kick start my training as a sissy. Well, that and to help convince me to pick her father, the dean, as my ‘mentor’.
They take the student/mentor relationship very seriously in this school. The mentor not only keeps track of your progress but performs a ton of your ‘specialty’ training both during and often outside the school environment. Of course, right now all the time I spend with my mentor is in my little prison here in the ‘secret’ secure area of the school.
Picking your mentor is about the only choice they give students around here. Not that I was given much of a choice. They only gave me a choice between four people: my father, Victor, Dr. Stanford or the Dean.
My father was out of the question. First off, there is no way I would want to live with my mentor. And second, he’s my father! Sure, as part of my training they have made me do things with my father. Plus, I’m sure they will make me do even more down the road. However, I’m not about to volunteer for it.
Victor is an instructor at the school and also a very long time close friend of our family. Despite him being Mexican and obviously not a blood relative, I grew up calling him Uncle Victor. For a long while I thought about picking him as my mentor. However, I feared it would mean additional sex with my father since my father and Victor spend so much time together. Plus, as the days went by during my training I quickly realized that Uncle Victor isn’t the type of person I thought he was. Let’s just say he hasn’t taken it easy on me during my training.
Dr. Stanford was my number one choice for about two seconds. He apparently can’t get hard so at first I figured he would be perfect considering I’m not gay. However, I quickly discovered that Dr. Stanford enjoys causing as much pain to his patients as possible. Picking him as my mentor would have meant years of physical torture in one fashion or another. No way did I want any part of that.
That left me with the Dean. I had various reasons why I picked him. However, looking back I now realize almost all of them are bullshit. When it comes down to it I picked him because I was blinded by love for Danielle, his son/daughter.
I still don’t fully understand what came over me in regards to Danielle. She is really a boy after all. And like I’ve already said, I’m not gay. So, how could I fall in love with her? I can only guess it is because I already had a crush on her from when I thought she was really a girl. That and the fact that she clearly took advantage of my time of weakness during those first few weeks and tricked me into falling for her. I now see this of course. I know I should hate her now that I can see this, but strangely a part of me still loves her… in a non gay kind of way of course.
Janice sits in front of her mirror putting on her makeup and fancying up her black shoulder length hair. She is so happy that she can’t help but giggle from time to time. Today marks a milestone in her training.
She is going to finally get to leave the confines of the secure area she has lived in for the past eight months. She is so excited. Yet, a small part of her is also a little scared. She has come to feel safe in her little prison. There are lots of dangers out there.
These dangers aren’t just from others, but from herself as well. In her secure little habitat there is only so many things she can mess up and get punished for. Out there is a whole world of random permutations that could result in her messing up.
Yes, it is scary as hell out there. However, it pales to the excitement of finally tasting freedom.
Not that it will truly be freedom. The non removable wrist watch she wears has a gps tracker built into it. They will also ensure they have a pair of eyes on her at all times. Sometimes it will be via hidden cameras and other times it will be a physical presence. Still, it is a ton more freedom than she has experienced since they locked her in here so many months ago.
“Hurry up, Nancy,” Janice growls at her soon to be ex roommate.
Nancy is actually Janice’s second roommate since her imprisonment started. Her first roommate was an eight year old redhead named Emily. It pisses Janice off that Emily only had to stay in the secure area for training for two months. It ticks her off even more that the same will probably be true for 9 year old, Nancy.
The reason for their short stay is obvious even to Janice. They are younger and it takes less effort to get them brainwashed. Plus, both of the little boys had some home training prior to being enrolled at the school. Janice had no prior training and was 14. She is old enough to know they are trying to brainwash her into becoming a proper little sissy. Therefore, it has taken them considerably longer to accomplish the task.
Even now Janice doesn’t feel they were successful. She doesn’t really feel any different. She still doesn’t feel gay or anything like that. Not really. Sure, she will quickly obey about any sexual demand put on her, but that doesn’t necessarily mean she is brainwashed… does it?
Janice also no longer wants to escape this place. Well, deep down she kind of does. However, she has come to accept that there is no easy escape. Sure, she could run away from home and the school but she will never be able to escape what they have turned her into.
Her transformation is more than just mental. For the past eight months they have been drugging her with their own special cocktail of estrogen and who knows what other drugs. Her body no longer looks like a boy’s. Her body is very soft and curvy now. Her breasts are also growing at an alarming rate. She is almost to a B cup already. Her breasts are almost as big as Danielle’s. And Danielle has been taking estrogen for years now.
Janice sometimes still cries when she thinks about her new body. However, most often she is proud of it. She is proud of how sexy she looks. Especially once she paints her nails and does her makeup and hair. She might not want to have sex with men but she enjoys the power her body has over them. Even the Dean sometimes drools over her. With a little more seduction training she is sure she will have her mentor eating out of her hand.
Janice isn’t stupid. She knows that she is really still a boy. However, that is what gives her the real power trip. The idea that with her looks and enough training she could probably seduce about any man. Even the heterosexual ones that know she is really a guy. She knows it is possible because that is exactly what Danielle did to her.
The school of course provides a lot more than just seduction training. It has the best academic record in the state. Once she graduates she will not only have the pick of whatever college she wants to attend but will be able to breeze through the courses like they are child’s play.
Janice pulls herself out of her daydream and heads to the bathroom to see what is taking Nancy so long.
Janice finds the little boy kneeling in front of the sink trying to put his butt plug in.
“It’s too big,” Nancy says between sobs.
Even Janice has to admit that Nancy looks cute kneeling there trying to force the large plug up her ass. Nancy has the cutest button nose and beautiful long curly blonde hair. If it weren’t for her tiny penis you would swear she was a real little girl.
Yeah, Nancy is going to make a very good Humbled girl. Even the way she pouts has a certain seduction to it. Janice can’t let Nancy’s quivering lower lip and pouting get to her. Like Danielle was once Janice’s trainer, Janice is now Nancy’s. Or at least for another 40 minutes or so.
Janice isn’t sure what will happen after today. They told Janice she would be going home after classes let out. However, they have played cruel jokes on her in the past. It is possible they will escort her right back here.
Janice lets Nancy struggle with the plug for a minute before taking action.
Nancy is still pouting but Janice notices the hint of a grin on the little girl’s face. Janice gets a little angry at the thought that the girl might be playing her. Today is Nancy’s first day with her new number 2 plug. It is 1.75″ [4½ cm] thick at it’s widest point so it is entirely possible that it is too big for her.
When Nancy holds the plug up it becomes clear what the problem is. Nancy didn’t lubricate it first. Nancy is new here but she isn’t THAT new. The little minx is trying to get Janice to downsize her back to the smaller number 1 plug. Well, that isn’t about to happen. Not that Janice has the authority to make that decision anyway.
“Listen you little shit,” Janice growls as she stares down at Nancy. “If that fucking plug isn’t up your ass in the next minute then you will be getting a special visit from the Headmaster.”
Nancy swallows hard at both Janice’s tone and the mention of the Headmaster. Nancy has gotten a visit from the Headmaster before. It was not a pleasant experience. The Headmaster is in charge of dishing out the more severe punishments. The man didn’t even remove Nancy’s plug before administering a very severe spanking. Then the man made her… do naughty things.
Needless to say, the plug is in it’s proper place well under the one minute deadline.
Janice doesn’t like being mean to Nancy. However, she knows life will be a lot worse for Nancy if she isn’t trained properly. Not that Nancy needs much training. Nancy is just that… a nancy boy. The boy is either naturally gay or he was trained to be a sissy since birth. About the only thing Janice had to teach the boy was school procedures and rules for sissies.
Of course, Nancy’s hole needed some training as well. Apparently, Nancy’s dad has a small dick. Nancy could barely manage the 1″ [2½ cm] plug when she first arrived. That might suffice at home but not in this school. Most of the teachers and employees here have rather large cocks. Hence the ever increasing sized plugs.
Janice has to bite her lower lip to keep from giggling as Nancy rushes to get the plug into place. She has to bite her lip harder when Nancy gets it into place and slowly walks bowlegged out of the bathroom. Janice chastises herself for finding it funny. She knows from personal experience that a new size plug is always uncomfortable. Still, Nancy looks so cute doing her little duck walk. It will probably be a few days before the little girl will be walking normal again. In a couple weeks though they will just upgrade her yet again and it will start all over.
Janice is currently on a number 7 plug. It is exactly 3″ [7½ cm] at it’s widest point. It is huge, but nothing Janice can’t handle. Not after this many months of anal stretching. The truth is that she could probably handle an eight or 9 if she had too. Luckily, her trainers seem content at keeping her on a 7 plug. Either they don’t want her getting too loose or they plan to hold on to the larger plugs as potential future punishments.
As Janice helps Nancy do her makeup, she debates letting the girl know she is probably not going to see her again for some time. She decides against it. In the past few weeks Janice has evaluated Nancy’s kissing techniques, blowjobs and a few other intimate things. However, she has tried to keep it somewhat ‘professional’. She doesn’t want Nancy falling in love with her like she had with Danielle. She is sure Nancy will still miss her but her heart isn’t going to be broken. Leaving without saying goodbye will just make it even easier on Nancy to get over it.
And it isn’t like they won’t ever see each other again. Assuming they let Janice go home today like they promised, they will probably still send her back to the secure area occasionally to give Nancy additional training. Plus, they will see each other in the halls between classes once Nancy reaches her next training phase.
Nancy looks almost like a perfect little China doll by the time they finish with her makeup. The makeup is a bit too thick for a child this young but this is what Nancy’s real daddy wants. Not that Nancy will ever be allowed to be seen in public this way. It would draw too much attention. However, most Humbled girls spend very little time outside school and home. There are several little girls at the school that wear heavy makeup like this. They get teased a little sometimes by the other students but not too badly. Of course, they do often get a little extra attention from the instructors.
“God, Nancy is going to break a lot of hearts some day,” Janice thinks to herself as she looks the pretty little girl over.
Before leaving her, Janice leans down and gives Nancy a long kiss on the lips. At first it starts out with just their rosy red lips touching. However, it isn’t long before their tongues are dancing against each other.
Janice knows Nancy hates kissing boys other than her daddy. However, Janice knows it has to be done. Kisses like this will help convince Nancy it is okay to be intimate with other boys. The sooner Nancy accepts this the easier life will become for her. It of course isn’t the first time they have kissed like this. Still, it is the best parting gift Janice can think of.
As they finally part, Janice notices that Nancy is blushing profusely. It bothers Janice that Nancy still finds the kisses so embarrassing. She feels she has failed Nancy as a trainer.
Janice is only upset for a few seconds. She is leaving today! Nothing can put a shadow on that. She grabs her books and practically skips to the secure door at the end of the hall. Shivers of excitement tingle all over her body as one of the security guards open it from the outside. She takes one last look back at her all too familiar prison. She sees a very confused and concerned Nancy peaking out of one of the doors. Janice blows her a kiss and then turns and walks away.
Janice turns in her seat to see which of her classmates made the remark but there are a half dozen girls smiling at her. When she faces front again she hears more remarks but she does her best to ignore them.
The girls don’t know it but Janice actually has the upper hand. For the past eight months Janice has been attending the classes via the rooms’ cameras. Janice not only knows everyone’s names but also which ones are the smartest and which ones are the trouble makers.
Unfortunately, the teacher sits her next to some of the trouble makers. And of course it isn’t long before they are doing just that… causing trouble. Less than five minutes into the English class lecture Janice sees a wad of paper fly over her right shoulder and toward the teacher. The teacher turns back toward the class just in time to see it. He snatches it out of the air with lightening reflexes and his eyes follow it’s trajectory right back to Janice.
“Fuck!” Janice screams in her head as he motions for her to come forward.
Janice wants to deny throwing it but she knows the teacher is probably already aware of it. She also knows the teacher is going to blame her for it anyway. It is hazing 101. Janice seen this exact scenario play out with a few other new kids in the past. Someone frames the new kid and then the teacher accepts the obvious frame up. Janice could never tell for sure but it often looked like the teacher and various students planned it all out ahead of time.
She just wishes she could wear her leather collar. Having the Dean as a mentor has some privileges. One is that you wear a special leather collar. Anyone that sees that collar knows the Dean has a special interest in the wearer. If everyone knew the Dean is her mentor then they would probably leave her alone. Unfortunately, she isn’t allowed to wear the collar or let anyone know about her mentor for another two weeks. It would look very odd if she showed up on her first day with a mentor already. All the other students would know there was something very fishy going on.
Not that some of them don’t already know about the school’s sissy program. First, there are about 17 other sissies enrolled in the school. Janice has seen most of them visit the secure area of the school a few times and they have seen her as well.
A lot of those sissies have one or more sisters that attend the school. Those sisters know about the sissy program but not necessarily who all the sissies are. Or at least Janice doesn’t think they do. Janice has three sisters of her own that attend the school. Thankfully, she has no classes with them. Not yet a
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