Jakes Time at the Academy (Ch. 04)

Jake slowly wakes up feeling a strong strain and slight pain from his dick as he fully remembers that he is in a chastity cage. He sits up struggling to focus.

"Go to the bathroom and pee. It will help with the strain but it won't help the horniness." Steel says from Drew's arms.

Jake nods in a thankful smile towards Steel as he heads towards the bathroom. Jake tries to use the urinal as he has always done but when he begins to release his stream, it starts going all over the place and Jake realizes he has no control of where it goes. He tried to hold it as best as he can and quickly steps to the actual toilet to sit down. Jake thinks to himself how inconvenient it is to always sit down but thinking thats probably why there are so many cutouts in the latex outfits for this exact reason. Well, maybe as one of the reasons.

Jake steps out and walks back into his room looking for his folder of information with his class schedule and other useful things.

Class 1 - Sissy Basics 101

Class 2 - Gym

Class 3 (1 day/Week) Dual Class with Domminatrix

Sissy basics 101 is the class every sissy that attends Bridgestone Division of Statutory Academy takes. They have to pass this class to be able to move on to the next year. There are many basic things that every sissy needs to learn to be both a good sissy and understand what their role in the academy is.

The outfit for the first day is a solid black latex catsuit but this catsuit has tits to make sure they understand they are no longer just a male but a good girl sissy. Jack has some challenges in getting in this catsuit. Luckily he is pretty much hairless already so he doesn't have much trouble with having enough lube on his legs and arms. Drew and Steel are watching, chuckling every time Jake looks to struggle. Jake contorts his body in ways that look like he is a monster crawling on all fours trying to get the back zipper all the way up. He finally gets it up to his neck and he was happy he didn't have to wear a mask for today according to the syllabus. He puts on some combat boots and begins to make his way to the classroom.

Making his way into the classroom, it looks like half the students are already in the class and half the ones are not. Jake was surprised more students were not already there with how strict this Academy seemed to be. Each student that made their way into the room had identical outfits on but each person had a slightly different build and face. Looking around the room he saw many different drawers and glass paned cabinet. There were different shoes and high heels of all shapes and colors along with a myriad of other accessories.

As everyone settles into their seats, a high pitched whistle going along a melody begins to hit Jake's ears. It gets closer as clicks from high heels start to echo as well. Quickly after the noise starts, a tall women steps through the doorway. She is wearing a long flowy purple dress. With the sounds she was making in the hallway she must have had on high heels but they were hidden by the dress. She had on opera length black gloves with a black latex mask that had purple accents and a high ponytail coming out of it.

"Alright students, my name is Goddess Maria. I will be your teacher for Sissy basics 101. This will be an enjoyable class if you listen and do as your told but If you step out of line, there will be consequences." She says in a surprisingly calm English accent.

Jake looks around to see if he can read any other students' reactions or thoughts but everyone was eagle eyed focused on Goddess Emily.

"Stand up and go to the drawer in the back of the classroom. Get into a single file line and each of you will have the option of picking a butt plug that you are required to wear whenever you enter this classroom. My only rule with picking these plugs is that the person with the smallest plug after everyone has theirs will be required to stay after class for punishment. You may begin getting in line and picking your plugs." Goddess Maria says with a smirk that shows she enjoys the show about to unfold.

All the students jump up to try and get in line in front of the cabinet with 20 different butt plugs. Each one was progressively bigger than the last. The biggest one was slightly smaller than a person's fist and the smallest was no wider than a pill bottle. Jake was still trying to realize what was happening before he got up from his seat and to his demise he ended up in the back of the line. He knew what this meant for his fate in this first class. Jake watched as everyone in front of him grabbed their plug and he made his way to the drawer. There was only one plug left. He looked back to the front of the class to see if anyone else was watching his movement. The only eyes he saw were Goddess Maria's bright blue eyes peering down into his soul. After picking up the smallest plug he walks back over to his seat and tries to hide it but he knows everyone saw which one he picked up.

"Good job to most of you. This should teach you that you have to be quick and precise with your duties when your Dominatrix or Master commands something of you. As we all saw this young sissy did not follow my rules and picked the smallest plug. What is your name?" Goddess Maria said while looking directly at Jake

"Ja-Ja-Jake, Goddess Maria." Jake replied, trying to seem small to disappear from the attention on him.

Goddess Maria continued to grin as she spoke. "Well, Jake, I hope you are excited for what will happen after class but lets all get started on todays class. Everyone will be expected to insert their plug first. Everyone please continue to stand and give me a show while putting in your plug."

The class stood up in unison and each one had their own method of putting in a plug. Some students went over to the wall with the lube dispenser and began massaging the tip in to their hole. They would moan as each one got it further and further in. One student began fucking themself with it because he hadn't cum in days and was longing for something to allow him to release.

Jake looking around decided to try and give Goddess Maria a good show in the hopes that he wouldn't be too roughly punished after class. He brings the plug up to his mouth. Running his tongue over the tip of it. Showing Goddess Maria that he can use his mouth like a proper sissy. He inserts it to the base in his mouth making sure that he got it as wet as possible with his spit, some of the spit dripping off the base onto his desk. He bobs his head up and down a couple of times making sure to give Goddess Maria direct eye contact while doing so. He turns around letting Goddess Maria watch as he slowly opens the back of his catsuit and exposes his hairless pink hole. He hears Goddess Maria's hand begin to move and as he looks back at her she is seated at her desk with one leg on it and her hand up her skirt. She is slowly moaning while watching and enjoying the show.

Jake moves the plug, dripping wet, down to his hole. Due to it not being that big he pretends like it is and presses the tip slowly to his hole acting like he is working hard to get it in. He uses his other hand to massage his fake latex breast and give off small moans. While Jake was trying to give Goddess Maria a good show, he was getting turned on. His tiny dick was beginning to press against the end of his chastity cage causing a discomfort that could only be solved by cumming. Pushing in his plug he felt a wave of pleasure pulsing through his body. He was fucking himself with his tiny plug, starting to wish he had something bigger. Hearing Goddess Maria's moans getting louder and more frantic, he began fucking himself quicker and quicker with his plug. He moans louder and in unison both Jake and Goddess Maria finish. Jake dribbles a small line of cum out of his cage while Goddess Maria is squirting under her desk hearing drips coming from under her. Jake unsure if he was supposed to or allowed to cum turns to Goddess Maria in the hopes of some type of approval but she only glares at him in disappointment.

Jake understands that that was a big mistake and mentally prepares himself for what will come soon after class is over. He is relieved that he came but is nervous of the consequences to his actions. After seeing the student beat and fucked during orientation, he knows he is in for a rough one.

Goddess Maria catches her breath and composes herself. "Good job to most of you. There were many good shows and as you can tell I enjoyed myself watching all of you work your plugs in. I want all of you to continue to train yourself to take your plugs or bigger plugs if you wish to impress me in the future. The goal is to be prepared for any use that your owner might have for you and being stretched and ready is one of those cases. You never know when you may be punished." Goddess Maria said the last part with a sinister tone and eyeing Jake. "I am very pleased with you all. Please take the rest of class for yourself, I have some work to do with this Sissy."