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Chapter 5
by
Demi_Blazen
What's next?
Tasks
I closed my eyes and whimpered. My mouth was so dry and my teeth were clattering. The fluorescent lights buzzed overhead, making sure every detail of my nudity was visible in case anyone passed by.
I wanted so badly to run. To cover myself and squeeze into the doorframe, hiding as much of my modesty as I could.
But my feet wouldn't let me. They were planted to the ground as if rooted there. I couldn't disobey no matter how hard I tried.
Hands behind my back. Chin up. Legs spread. I waited in that position as if inviting the world to look at my tiny caged cock.
The worst part was that I couldn't see the time anywhere. There was no clock in the hallway. I didn't have a watch on and if I did, my hands were tucked behind my back anyway.
I heard a door open at the far end of the hall. My heart beat skyrocketed. I squirmed. My hands fidgeted like crazy behind my back.
Please don't look this way. Please don't look this way. Please don't see me.
My cock throbbed. It's cage was squeezing it, a little pink prison drawing attention to itself in the most embarrassing way.
I heard talking from down the hallway. A group of male voices.
"Please mistresses. Please... I'll be good. Please mistresses..." I muttered under my breath, half-crying.
It felt like so long. Eternity. How many hours had I been out there? The conversation continued.
Every second I knew they would see me. I felt deep down that I was screwed. My life was over. I would be seen. Everyone would know how pathetic I was.
They got closer. I swear they did. Their voices boomed. It was like they were right on top of me. Looking at me. Seeing me.
Finally, I moved. My body turned and opened the door. I fell to my knees the moment I was back inside and felt tears roll down my cheeks as the door slammed shut behind me. That had been so close. Unbelievably close. If one of those guys had looked in my direction...
"Oh my god, are you crying!" Nicole burst out laughing. "You are such a pussy!"
But Miss Bennett took me by the hand and lifted me to my feet. "Aw, there, there, sissy. Did you learn your lesson? Will you be a good, obedient boy for your mistresses?" She clutched my head to her chest, squeezing it against her breasts.
I felt the cups and lining of her bra. The squish of her supple breasts. The warmth of her skin and beat of her heart. She stroked my hair with one hand.
"Y-yes Mistr-"
"Shhh... " she muffled my voice by squeezing me tighter, my mouth plunged into her cleavage along with the rest of my face. "Just cry, sissy. Let it out. There, there. Absorb this lesson. That was only a small taste of what happens when you disobey, understand? I don't ever want to punish you again, Barry. But I will if you test me."
I could hear the eye-roll in Nicole's voice. "What a little crybaby. You're lucky I didn't pick your punishment. I would have walked you up and down the hallway on all fours. Made you bark like the little bitch that you are!"
I whimpered and cried harder into Miss Bennett's breasts. So grateful that I was able to feel them, to hide in them. She let me stay there for a while, then pulled me back by the hair to look up at her.
"We don't have much time left, Barry, dear. I have classes to teach and you and Miss Nicole have classes to attend. So before we depart, it's time to receive your first tasks."
I gulped. I had been dreading this since she'd first mentioned tasks.
"Before we go, we will be confiscating all of your masculine underwear and replacing them with panties and bras. Starting tomorrow, you will choose your own feminine underthings to wear under your clothes along with your cage. Panties and bra. Not one or the other. In addition, you will be expected to go shopping for more panties and bras as needed or wanted. You will not be allowed to wear dirty clothes so it is in your best interest to maintain what you have or be ready to purchase more. You may go commando today. Understand?"
They both looked at me. All I could think to do was whimper out a "Yes ma'am..."
Miss Bennett nodded as if this was acceptable.
"Finally, you will report to one of us for inspection every morning. I will be in my office before classes. Nicole will be in her dorm room. If you pass inspection, you will be allowed to go about your day. If you fail, you will be punished. We may also give you additional tasks based on what we think is best for your continued education. Remember; you will not be hypnotically induced into following these orders. You must follow them of your own free will or face the consequences. Is this all clear, sissy?"
I nodded. "Yes ma'ams..."
"Good boy!" Nicole slapped me hard on my butt. "I bet you won't be brave enough to come to my room for inspections, sissy. Your little virgin ass wouldn't be able to handle setting foot in the girls' dorm!"
I gulped and nodded. She was probably right, though it pained me to admit.
Miss Bennett then bade Nicole to help her search my room for masculine underwear. They took every pair of boxers I owned and left me three panties and three bras. Pink, white, and baby blue.
Then they left.
I spent the rest of the morning getting rid of all the packaging from my new sex toys, and hiding them in my night stand.
After that it was time for classes.
What's next?
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Sissy Diary
A Beta's Story
Hypnotized by Alphas, Feminized and Sissified.
Updated on Feb 19, 2026
by Demi_Blazen
Created on Feb 17, 2026
by Demi_Blazen
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