A Sissy Super Senior Pt. 01

A Sissy Super Senior

All characters are over the age of 18!

Hi everyone! This is just the prologue, but I'm so excited to be diving deep into Sebastian's transformation into Sophie in later chapters. The next chapter is almost ready, but for now I hope you enjoy chapter 1!

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Sebastian Berns was a nice, well meaning guy. Growing up, from pre-k to 8th grade, he was a star student. Without trying, he was the top of his class in every subject. That is, until Sebastian started high school and the amount of work needed to succeed dramatically increased. Sebastian- having never needed to try in his life to get an A+, suddenly found himself lacking the study skills or mindset needed to do well in high school. And unfortunately, he put his focus on hanging out with friends and... other things. For reasons Sebastian couldn't articulate, he was immensely fascinated in crossdressing. Even at a young age. Sebastian doesn't remember when exactly he became fascinated with crossdressing, but it was a huge, albeit secret part of who he was. Even now, as a senior at Lincoln High School, Sebastian would spend every night reading and masturbating to gender bending fiction stories. He read on his phone, on his gaming pc, and late at night he'd open up a private browser on his school-issued take-home laptop, and read there- imaging himself in the scenarios. But this obsession never fully consumed him. "It was just a fetish" he rationalized to himself. "Eventually I'll grow out of it and be a regular dude." It's a shame- if Sebastian spent half as much time learning proper study habits as he did fantasizing about crossdressing at nights, maybe he wouldn't' have failed his fall semester Calculus class.

"FUCK!" Sebastian thought to himself when he checked his online grade portal on his school laptop. For core/mandatory classes, Lincoln High required at least a C- for it to count towards graduation. With only a 30% this quarter, Sebastian would need a 110% next quarter to get a C-. He immediately emailed his Calc teacher, Mrs. Lopez, to see if there was a chance for extra credit next semester. The following Sunday night, Mrs. Lopez responded with a brief rejection to his extra credit appeal. Not that it would've helped- there was no way he would have enough regular credit to reach an A, let alone an A++.

Realizing there was no salvaging his Calculus grade, Sebastian accepted his fate that he would need to take summer school. "Well, if I'm failing Calculus anyways, might as well stop showing up." Sebastian said- in an attempt to console himself. So Alex kept his Calculus grade a secret from his Mother, a single mom raising him. Sebastian's mom knew he was struggling in school- well struggling implies you at least were putting effort in. Sebastian's mom knew he wasn't doing well in school, but she knew her son was still the smart young man he was before high school. And she had figured he was doing fine enough to get into a respectable state school- Sebastian, while not really caring about high school, did talk eagerly about going to college and studying Journalism to become a healthcare journalist. So at the very least, Mrs. Berns was happy that her son had career interests.

The following quarter, Sebastian would just cruise through his classes, and put absolutely zero effort in listening in whatever was happening in Calculus. Sometimes he'd try and formulate how he'd break the news to his mom that he'd need to take summer school before college. Not wanting to dwell on it too much, Sebastian decided to focus on watching anime in the back of class on his laptop, on mute. One time, he was so bored he started reading crossdressing fiction on his laptop, with the screen brightness low enough so nobody would see. When it came to the homework, Sebastian used chatGPT to answer it. When it came to quizzes and tests, he just guessed his way to a solid 25-45% on them. On his the 3rd test of the quarter, Sebastian surprised himself with a semester-high score of a 58%. With the words "F." "SEE ME AFTER CLASS."

Sebastian, while not in the mood to talk to Mrs. Lopez, figured he'd tell her about his plans to take the class in summer school. As soon as the class had left and it was just him and her, Sebastian was ready to open his mouth before Mrs. Lopez angrily cut him off.

"I do NOT want to hear a word from you Sebastian. Move your ass to the principals office. NOW!"

Sebastian immediately became red in the face, and followed Mrs. Lopez (who was walking far too fast for him to keep up) to the principal's office. It was clear in her face that Mrs. Lopez was furious. Students who were in the hallway, laughed as they figured Sebastian was in some sort of trouble. "I wonder what the fuck Seb did?" Sebastian heard some guy he was friendly with in P.E snicker to his friend.

When they arrived to the principal's office, Sebastian saw the principal, Mrs. Kyle sitting at her desk with a stern face. Alongside Mrs. Kyle was Sebastian's mom, who looked angry. And pale.

"Oh fuck." Sebastian thought to himself. "They definitely told her about me failing Calculus. DAMMIT! I just needed some more time to let her know I'm going to retake the class in summer school."

"Sebastian, thank you for coming. Please, have a seat next to your mom." Sebastian nodded, still red, and sat down meekly next to his mom, whose anger was radiating from her.

"Mrs. Berns, thank you for taking the time to come. As we explained on the phone, Mrs. Lopez has reported to me that your son is abusing his school resources. For starters, Sebastian failed his first quarter of Calculus- obtaining only a 30%. The lowest grade amongst his entire class.

"SEBASTIAN?" His mom spat. "HOW DO YOU ONLY GET A 30%? AND WHY DIDN'T YOU TELL ME?" "Mrs. Lopez, is there any extra credit opportunity, or chances to redo some failed homework or tests to get his grade back up?"

"Unfortunately, Mrs. Lopez, if Sebastian received that opportunity, other students would need to be given that same opportunity as well, for the sake of fairness- And that simply isn't possible. Under normal circumstances, Sebastian's only solution would be to either score high enough this current quarter to compensate his first quarter- as semester grades are decided as the average between the two quarters. But your son would need a 110% this quarter to pass the semester a whole- which is an impossible grade to achieve. Even if I were to offer him extra credit, which would be unfair to the students who actually worked hard but came short of receiving an A, Sebastian has failed every test and quiz of this quarter so far. I suspect Sebastian just merely assumed he could take summer school after his senior year to make up this classes credit. But.."

"But?" Sebastian's mom asked worryingly.

"But." Mrs. Kyle interjected. "But unfortunately your son has severely breached Lincoln High School's code of conduct."

"What??" Sebastian asked shocked. While he had planned on speaking as little as possible in this meeting due to the shame he felt. He hadn't had a clue as to what she meant by "breached the code of conduct." And impulsively joined in the conversation.

"Sebastian. When Mrs. Lopez first came to me to disclose your abysmal Calculus performance. We wanted to give you the benefit of the doubt. I took a look at your file, and there were no extracurriculars. I spoke to your other teachers and they said while you were a friendly, respectful classmate to your peers- you also had a 'C's get degrees' mindset. We asked other staff members, including the lunch staff if you were being bullied by other students, and they all had nothing to say except that you're a well liked member of Lincoln High. A well meaning, but lazy member."


Sebastian turned to his mom to see if hearing Mrs. Lopez talk about how everyone in the school loves him would make her feel better about the situation he's in would make her feel better. She was still stone cold and focused on the "lazy" description.

"But how did my son break code of conduct?" Mrs. Berns asked.

"Well.. when we became fully confident that your son had no scholastic factors impacting him from actually putting in effort into his classes. I requested the technology department run a search on Sebastian's laptop, to see if there was anything more we should know about him. Per the technology agreement that all students signed, faculty has the right to freely check what students browse, as these laptops are for schoolwork only. So even websites accessed on private browsing are accessible for the school administration to view."


"FUCK!FUCK!FUCK!FUCK!" Sebastian said as he became redder and redder. His body was burning in shame. His heart was beating too fast. He knew his life was over at this exact point. Well, little did he was right. His life, as he knew it at least was over. And today was the prologue of a new chapter in her life.

"Okay? And? Sebastian. What did you do on your laptop?" His mom asked coldly.

Tears were beginning to form in Sebastian's eyes. "I uh- uh. I- I- I"

"Mrs. Berns. Not only has your son been using chat websites to message other classmates during class. Not only has your son been streaming tv shows during class hours. Your son, both in class and in your home as been consuming transgender pornography on his school computer.


"WHAT?SEBASTIAN, WHAT??????" Mrs. Berns yelled.

"Now hold on! Hold on!" Mrs. Lopez suddenly chimed in, worried she would see Sebastian get his ass kicked in front of his own mother.

Tears were strolling aggressively down Sebastian's eyes. He's never felt more humiliated in his life. He felt like a freak in front of the 3 women before him. And there was no way his mom wouldn't beat his butt when they got home now. His mom would never look at him again, he thought. Before he could start praying that the floor would open up and suck him through it, Mrs. Lopez surprisingly came to his defense?

"Now yes. What your son was accessing consuming was wildly inappropriate for a school device. ESPECIALLY during class hours when I'm taking the time to teach. But the material your so- Sebastian was consuming seemed to tackle themes of gender expression and gender fluidity, albeit in crass manners."

"Oh god, did Mrs. Lopez actually read his search history? Did Mrs. Kyle?? Are they going to share them with mom?" Sebastian painfully thought.

"Sebastian..." Mrs. Lopez spoke to him softly- for the first time in this entire situation. "Do you, and pardon my forwardness, have issues with your gender identity?"

Sebastian looked around the whole room quickly. Mrs. Lopez and now even Mrs. Kyle looked at him more empathetically. His mom however, looked at him like she wanted to maul him.

"What the hell? I don't know if I have gender dysphoria. I don't think so? I just thought crossdressing seemed kinda hot. Definitely not anymore though- at least I'm finally fixed thanks this damn trauma" Sebastian thought to himself. He didn't want to directly answer Mrs. Lopez. But he saw based on everyone's look they expected a response. "Maybe I should just

"...sometimesyeah." Sebastian mumbled.

"Sebastian!" His mom said. This time sounding genuinely shocked, almost guilty sounding.

Crap! Maybe if he actually plays into it, he'll get out of this mess, A'okay.

"Sebastian, Im sorry. That must be hard for you. At Lincoln, you're free to express yourself any way you'd like. We have counselors and resources you could have spoken to. Especially if it was affecting your school work.

That wasn't the case at all. Crossdressing had nothing to do with Sebastian's lack of academic rigor. But it seems like Mrs. Kyle was making assumptions- that the other ladies in the room bought into.

"Oh Sebastian..." His mom said, sympathetically.

"I'm sorry... I swear I didn't mean any malice with my laptop usage. I didn't know my search history was being stored. I'm sorry for letting myself go in Calculus, I really will try in summer school."

"Well that's the thing, Sebastian.. I don't know how to tell you both this- Mrs. Kyle started.

Mrs. Berns tensed up, as did her son.

"But due to your failing grade in calculus, your lack of diligence in your other classes, and misuse of scholastic technology both in and out of the classroom- you do not meet the standards we hold the academic or behavioral standards we expect of Lincoln seniors. After a review with my higher ups at the school board, I truly think letting you cruise through the rest of Senior year with little effort, then putting in the bare minimum effort to get a C- in summer school will set you up for failure in the real world...

...

"So unfortunately, we believe the best course of action is to hold you back a year."

The sinking feeling Sebastian had just a few minutes prior magnified itself. He thought he was going to puke. He turned to his mom, and while he was drenched in panicked cold sweats, she seemed much more relaxed- determined almost.

"Mrs. Kyle, Mrs. Lopez, I'm so sorry for my son's actions. Is there anything he can do

"We appreciate that Mrs. Berns, but unfortunately this decision, per discussion with the school board is final. We can't in good conscience let Sebastian off that easy. It's not for to himself, or the students who are working hard to graduate." Said Mrs. Kyle

*sigh* "I understand... I'll see to it Sebastian finished the rest of this year on good standing... as next as... as well as next year."

"And don't think because you'll be staying for another year, that means you continue to not try, starting Monday, Lincoln High expects you to be putting in maximum effort in your studies." Mrs. Kyle sternly warned.

"yesmaam" Sebastian glumly whispered.

The meeting wrapped up and Sebastian and his mom got up to leave. Sebastian's legs felt weak. He'd have to repeat a whole year of school? What would his friends say? What would his brother? What will his mom do to him at home? "FUCK! FUCK!" He thought.

Right before they walked out, Mrs. Lopez called out for them to wait.

"Sorry! I just... I just wanted to say, Sebastian I know this may be hard to take in. And while you have nobody to blame but yourself, I do want you to take see this as an opportunity. Not everyone gets a second chance in life... And you know what? I'll be here for the rest of this year. And next! To support you."

"That's very kind of you to say Mrs. Lopez. All the staff here will be available for your support Sebastian. And remember- if it makes you more comfortable to succeed here at Lincoln, maybe you should consider expressing yourself the way you truly see yourself? We're accepting of all gender identities at this school." Said Mrs. Kyle.

Sebastian was uncomfortable at that notion. But his sense of shame and humiliation had reached its peak (or so he thought...) Unbeknownst to him however, his mom held on closely to Mrs. Kyle's words.

"Thank you ladies both so much for your support of my s- my child." Mrs. Berns responded. Mrs. Berns had to return back to work, and luckily for her, and maybe Sebastian too, her anger had subsided. "Maybe this is for the best?" She thought to herself. She knew her son wasn't a stellar student academically, but she never expected him to fail a class, considering how socially adept he was, and how he had career aspirations. "Maybe Sebastian does have gender identity issues?" She thought empathetically. "...Or maybe he's just a damn perv?!" Was her counter thought. "Regardless... if my son can't be a star student, maybe my *daughter* will?"

...To be continued...