Sissy Baby Chastity

When I was fourteen, during my first year at boarding school, was when my life changed forever. It wasn’t what I was planning on, but I guess I deserved what ended up happening to me. The school was divided into two campuses, one for males and one for females. I stole away to a broom closet on the far side of the boys’ half of the school, right next to the girls side, with a boy a year older than me, because he’d said he wanted to fuck me in the ass. I liked the feeling of being wanted and decided it was probably safe, so I let him.
The physical rush of being fucked ranged from exhilirating to almost sickening, like a bumpy car ride where you have to brace yourself against the roof. My semihard member flopped back and forth, drizzling precum from my prostate being rubbed.

Suddenly, something happened that made my heart stop. From behind us came the powerful, imperious drone of the voice of the headmistress of the girls’ school. “Enjoying yourself, young man?” she inquired acidically.

She’d only said young man, I thought, could she not see that there were two of us? “Climb down off that girl immediately and report to the headmaster of the boys’ school immediately!” she snapped, yanking the other boy by the arm and fairly catapulting him out the door.

She then returned her attention to me. “And as for you,” she paused for a moment in bemusement, now able to fully view my form, then continued, “YOUNG LADY, it would seem that you have been getting fucked like a little whore, and you will therefore report to my office for discipline this instant!”

“B-but I’m a boy!” I began to stutter, at which she cut me short with the command, “NOT ONE MORE WORD!” and began to drag me by the collar down the hallway into the girls’ school. I hardened as she spanked my bottom to hurry me along and tried cover myself which caused her to swat my hands away, which increased my arousal. Being dragged into the headmistress’ office, I saw it was occupied by of the female teaching staff. “Oh, is this a sissy baby?” asked one of them. I gulped, not sure what she meant by that. T

he headmistress concurred that it was and the teacher smiled, remarking she’d not seen in one a while. I began to ask what they meant, which prompted two of the women to pin my hands to the headmistress’ desk, while she stood behind me and began to flog my bottom mercilessly with a paddle. She spanked me over and over again until my butt was trembling and tears came out of my eyes. She walked around and placed her finger on my lips. “You are not to speak unless spoken to. Nod if you understand.” She instructed, and I replied in the affirmative by nodding. She then continued speaking.

“Ladies, I’m happy to report I found the source of the banging noise that previously interrupted our faculty meeting. It was coming from the boys side of the school so I expected to find some young men roughhousing, and instead what should I happen upon but this little girl, actually allowing herself to be fucked! As you can see, she is not only out of uniform but has messed herself.

Young lady, for acting like a little whore over in the boy’s school you will now be subjected to the strictest punishment that can be meted out while still allowing you to continue your education. I’ve caught you acting like a whore, and I could have you ejected from school and you could be remembered forever by the name whore. Instead, I’ve decided to keep a close eye on you.

You’re hereby restricted to the girls’ school where you belong, where an eye can be kept on your dirty little sex habit. Instead of a whore, I’ve decided to make sure you will be remembered as the opposite of a whore. Instead of a juvenile offender, you are going to be my sissy baby, and your new name is going to be Chastity. Would you ladies please take off those nasty clothes and remove her body hair?”

The other female staff went to work quickly snatching away my shirt, blazer, and bunched up pants, then held me by the shoulders, rubbing a cream all over my body that quickly removed my hair as they wiped it off.

“Now then, I believe we have an extra uniform which will be more appropriate for you. As a student in my school you will be expected to wear a proper uniform. Every day until you graduate you will be expected to wear a bra, panties, knee socks, a blouse, and a skirt, just like all the other girls.

Furthermore, in light of your little infraction, you will clearly need to be monitored at all times to prevent you from being sexually irresponsible. You will wear locking anti-masturbation mittens to prevent you from fiddling with yourself, and you are not allowed to go into the restroom as you might use the privacy to touch yourself.

Because you need constant monitoring like a baby, it only makes sense that you wear diapers like one. Diaper her.” The female teachers quickly responded to this, all three of them guiding my nervous form to the carpet. I tried to give some resistance to see if they were just kidding and would let me go, at which they twisted my arm and pinned me to the ground in a way that made it impossible for me to move.

I got really hard as they slid a huge diaper under my bottom and they cooed mockingly, “Sissy Baby Chastity’s going to remember this for a looooong time!” then quickly pinned the diaper shut. After this they slid a pair of locking panties, which looked like normal girl’s panties on the outside but were rubber on the inside, up over the diaper and locked them. I was held as they forced me into the bra and the rest of the schoolgirl uniform.

As they did this the full consequences of everything they’d said began to sink in. They weren’t going to let me cum? I grew desperate at the thought, and my hands shot down to the locked diaper. I began to beg as I tried to masturbate myself through the thick diaper and panties, managing to yelp the word “please” before the headmistress clamped her hand over my mouth. “The mittens… and a pacifier.” she said coolly. The women locked mittens over my hands and connected them with chains to a collar they locked around my neck.

The chains were long enough to let me reach the area around my torso, but prevented me from reaching my crotch. They then brought into my line of sight a huge pink pacifier attached to a locking strap and forced it into my mouth, locking it behind my head. “That should prevent any further outbursts.” said the headmistress. “I was going to allow you speaking privileges, little girl, but since it’s obvious you’d misuse them you’re now down to crying privileges.

You may cry if you need a diaper change, and only then. If you are not both wet and messy you do not need to be changed, and if you abuse your crying privileges by crying for a diaper change without being wet and messy you will only be changed once a day regardless of how much you cry, and we will be sure to feed you enough that you’ll have a diaper rash all the time. Nod if you understand, baby girl.”, I replied with a nod.

“Let’s let Sissy Baby Chastity get a look at herself for just a moment. I want her to know what everybody’s about to see.” said the headmistress, and the teachers took me by the shoulders over to the full length mirror the office contained. I was mortified at what I saw. They made me look like a girl! The huge diaper could easily be seen protruding from underneath the short skirt I’d been forced to wear, and in the direct indoor light it was obvious that I had a bra on. I didn’t want anybody to see me like this, but I wasn’t being given a choice about it.

To complete the outfit, black patent leather mary jane shoes were buckled onto my feet. “Alright, I’d say Sissy Baby Chastity’s ready to go back to class.” announced the headmistress. I wanted to scream as I was walked down the hallway but couldn’t due to the gag in my mouth. The only sounds were the clicking of the girls shoes on my feet in time with the rhythmic swatting of the teacher’s hand against my diapered bottom, and the sounds of girl’s voices emanating from the classroom we were headed to as they wondered aloud who was on the way.

For the next month, I got no relief, and no privacy. All the females at the school obviously knew I was a boy being punished but loved to tease me by calling me a girl, which increased my sexual frustration horribly as did the feminine trappings I was surrounded with. The girls could tell I was aroused by things like dresses and lingerie and they made use of this fact to worsen my torture, doing things like rubbing my legs sensuously during forced shavings and saying how “pretty” they were and discussing in agonizing detail the styles of bras and panties they were going to make me wear under my schoolgirl outfit.

They quickly figured out what turned me on the most and progressively got to the point of forcing me to wear lingerie that made my chaste state particularly unbearable all the time. At night I was locked hand and foot to the bed I slept in to prevent me from touching myself, and I more than once awoke to find myself being force fed from a huge baby bottle. After they fed me this way the girls would usually rub my tummy and tickle my feet to force me to use my diaper.

Even more embarrassing than being forced to use my diaper at times like that was the fact that it was tiring my bladder and bowels out and I began to have accidents. Much was made of “sissy’s diaper change”, at time at which I after blubbering sufficiently to be released from my wet, messy diaper was physically forced by three or more women onto the surface that made the most convenient changing table and changed into a fresh diaper after slowly being cleaned with baby wipes in a way that titillated me incredibly but didn’t let me cum.

All the girls made the nature of our relationship highly physical, doing things like caressing me unexpectedly and cuddling and kissing me relentlessly after lights out, and after a month I thought my penis was going to explode.

When I was called into the headmistresses office at the end of the month I was desperate for any good news she would give me. The girls of the school had done a thorough job of steadily increasing my arousal and my schoolgirl outfit was even more embarassingly erotic than before. I was made up pink to match my pacifier, down to my fingernails and toe nails.

They’d tied my blouse off above the midriff so the silky, lace trimmed bra I had on was easily visible. The bra matched the silky white panties that covered my extra-thick diaper, which could be plainly seen due to the extremely short skirt I had on. The panties were complemented by a pair of white stockings trimmed lace that went up my thighs.

The girls had found the feeling of nylon on my legs turned me on more than leaving them bare, so they had me in thigh highs all the time. The headmistress spoke calmly from her seated position on her office’s sofa. “Sissy Baby Chastity, your punishment as of today has been going on for one month. Today, I will find out if you have learned anything from it. You are to get on your hands and knees and crawl to me for a feeding.”, she said. I did as I was told, crawling to her as a baby would. I lay across her lap, and she removed my pacifier and began to lull me into a state of relaxation, telling me I was a good baby girl and holding the bottle firmly in my mouth.

I wanted to cum so badly that tears rolled from the corners of my eyes, which caused her to become even more maternal, and she continued to coo and whisper into my ear. “Did Sissy Baby Chastity try to cum like a girl?” she asked. I nodded. “Does Sissy Baby Chastity understand she is not allowed to cum?” she asked, to which I nodded again. “Oh.” she replied with a smirk, and reached down to the front of my diaper.

She placed her hand flat on the surface and began to grind it into the padding that surrounded my aching penis. I came, filling my diaper with jets of jism for what felt like over a minute. She smirked at this.

The headmistress said because I’d orgasmed without her express permission, I was to be expelled from my grade level. She and the other female faculty explained to me that it was plain to them that I loved dressing like a baby girl and cumming in diapers, and that since I liked that so much I was to be demoted to preschool and wear only diapers and baby dresses.

She wrote a letter to my family explaining that I had been selected for a special tutoring program, by which she actually meant I was being forced to become her prisoner. I’m being taught how to beg for orgasms without the power of speech, which means crying in a way that the headmistress, now my mistress, finds especially cute or by attempting to scribble requests in crayon with my mittened hands. Half the time I only end up earning a punishment.

She always makes a huge deal about me needing diapers when she changes me and I think she’s making me incontinent, but I can’t do anything about it. I realized recently that she’s been lacing the nipples of my pacifiers and bottles with something that makes it difficult to speak, and I think it’s affecting my motor functions too.

She takes me to the girls school to force me to try to walk and talk sometimes, and she and the girls there have fun waiting for me to void my bladder and bowels so they can make a big deal about it being time for “sissy’s diaper change”. I’m physically being turned more and more into her incontinent sissy prisoner, while on a mental level all I can do is observe as this happens to me.

The other day, mistress was taking me home from another session of being humiliated in front of all the girls at school as usual. She had me locked into a stroller and wearing a frilly pink dress. I smelled like baby powder and the mess I’d just made in my diaper, and I was looking forward to being changed.

From behind a nearby door I heard a graduation march and the names of some of the other boys I’d known at school being called, and realized my former class was graduating. I was hit with a wave of humiliation at realizing what was happening, that instead of graduating I’d been transformed into a crossdressed, diaper wearing sex slave with no hope of escape, who was being escorted home to dinner from a baby bottle and a wardrobe consisting of nothing but diapers and the most revealing lingerie and dresses my mistress could find.

I tried to whine about it from behind the pacifier gag, to ask her to consider letting me back into school so I could get back what I’d lost. The desperate cry of “Mmmmmf?” came from behind my pacifier gag.

Mistress smiled, saying only “Sssssshhhhh.”, and continued to wheel me, her captive, home for a much needed diaper change.

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