A Sissy Super Senior Pt. 02

All characters are over 18!

(Make sure to read part 1 first!)

Chapter 2:

After that nightmare of a meeting, Sebastian meekly sat through the rest of his classes, keeping to himself as he avoided talking to his friends. He couldn't bare feign happiness as he just found out he was going to be held back his senior year- becoming a "super senior." How would he tell his friends? Should he? These thoughts were racing through his head, along with dread of what would await him at home.

Finally the school day had ended, and it was time for Sebastian to head home. During the bus ride, his friends all sat around him, and to his dismay talked about their future college plans. Sebastian realized to himself he'd need to withdraw all pending applications to local city-college and state schools, as well as cancel any SATs he was signed up to take. "So Seb, you think you'll rush any fraternities?" His friend Connor asked.

"Uh.. y-yeah, maybe?"

"Sebastian, if we both get accepted into SUNY, that would be so cool! I have a sister who rents a place there, so we can get her to get us booze!" One of his close friends, Sarah- who he would've asked out if she didn't have a boyfriend, earnestly said to him.

This one definitely hurt Sebastian the most. He always thought Sarah was cute, but since she was taken he was just happy to be her friend. Sebastian always figured he'd have a good shot at getting into SUNY. It was affordable, and he did particularly well on his practice SAT. So that, alongside the personal statement he had drafted up (which even his mom was blown away by) made him pretty confident he would get in.

"I would love that!" Sebastian responded, masking his pain.

When he finally reached his stop, Sebastian made his way home. As he opened his door, he was surprised to see his mother, who he figured he wouldn't see again until later in the evening. "H-" "After our meeting, I went back to work, but told my boss I needed the rest of the day off to take care of some family things." Mrs. Berns said, cutting her son off.

"Mom I'm so so-" "CAN IT!" His mother snapped, once again cutting him off. "ARE YOU SICK IN THE HEAD? SLACKING OFF TO SUCH A DEGREE YOU'D FAIL MISERABLY IN CALC, AND NOT EVEN TELL ME? YOU'D THINK AFTER THE FIRST F, YOU'D FINALLY START FUCKING TRYING? OR WAS YOUR PORN RIDDEN BRAIN TOO HYPER-FIXATED ON WANTING TO BE A FUCKING GIRL?"

Sebastian burst into tears. "Momimsorry! Im so so-!"

"I SAID CAN IT!" Mrs. Berns shouted, slapping her son in the face.

Sebastian fell to the floor, not because of the slap, but because of the emotional exhaustion and shame today brought all finally took its toll on the 18 year old. While yes, Sebastian was a kindhearted young man, he was a slacker when it came to academics. And now his mom, his teacher, and principal knew his most shameful secret. On top of it all, he had to face the the looming embarrassment of being a super senior, and postpone his excitement of going away to college. Poor Sebastian was sobbing hysterically.

"Now..." This time, his mom's voice was much quieter and colder, compared to the shouting from before. "I don't give a fucking shit if you want to take hormones, or transition, or maybe you don't want to do any of that? I Maybe you're just a stupid fucking sissy?" Either way, I would've supported you. You know I raised you to be open-minded. What I didn't raise you to be, was a fucking IDIOT! WHO USES HIS SCHOOL COMPUTER TO READ UP ON THIS TYPE OF SHIT!" Now, shouting again.

"Mooooom! Ple-" Sebastian whimpered, before once again being cut off. "I SAID DON'T TALK!" "Now I'm guessing since you kept the fact that you failed your first quarter of Calculus, and that you panned on taking summer school, a secret from me that it's because you were too afraid to tell me. Is that correct?" "yes." Sebastian whimpered.

"Well, I'm assuming you're going to want to do the same to your friends and classmates. I can't imagine how rough the bylining would be if they found out Sebastian Berns will be held back a year!"

"...yes." Sebastian again said.

"Good! Because starting today you are to have ZERO. Zero fucking content with ANY of them!" "No texting. No hanging out after school. NOTHING! Every day, you are to report back straight from home, and you are to give me a detailed list of what homework you were assigned, and when your next upcoming test and quizzes are. Does that make sense?"

"Yes ma'am." Sebastian meekly responded. Just like that, he realized.. All his friendships were gone.

"Finally! The first smart thing you've said or done seemingly all school year!" Mrs. Berns spat.

"Second matter: About this gender or crossdressing material you were STUPIDLY reading on your school computer.. You know, the computer they gave you for NOTE TAKING AND HOMEWORK???" "Are you trans? Answer truthfully, there's no wrong answer."

"N- NO! I swear mom, I'm not trans!" Sebastian cried out.

"Then why did you spend so much time on those sites?" His mother retorted. "I- I- uh... I don't know.. I just.. I thought they were inter-" Once again, Mrs. Berns cut her son off. "It doesn't sound like you know yourself, or maybe you do? Maybe it's another secret you're keeping from me, like your Calculus grade? Which is it?"

"Mom I swear, I don't know know why I did it! I'm sorry!"

"Sebastian... apologizing isn't going to fix the embarrassed you caused the both of us today. Apologizing isn't going to send you off to college in the fall. Apologizing isn't going to make you magically walk across the stage at the end of the school year. You showed to me today that you, clearly have issues. Both academically, and... personal." Mrs. Berns said.

Sebastian was tempted to respond, but he really had nothing he could say. He knew he messed up, and all he could do is silently regret he he had let his schoolwork slip so terribly.

"So, now that all's said and done.more can Sebastian's ego handle today? "And There's no changing the past. All we can do now is come up with a game plan for how you'll succeed the rest of this school year. AND next school year too. And since you lack the academic rigor or common sense to come up with your own game plan, I've come up with one for you, and you better follow it."

"Yes ma'am." Sebastian responded.

"To put it frankly, if you can't be a studious young man. I want you to try senior year... as a girl."

Chapter 3:

Sebastian was shell shocked. He heard ringing in his ears and it certainly wasn't because of the slap. He was dumbfounded.

"Huh?"

"I want you. To do your repeat of senior year. As a girl." His mom responded. Enunciating so the message would come across with more of an oomph.

"Mom, I can't. Please, I know what Mrs. Kyle told you, but please. I can't go to Lincoln as a girl!!?!?" Sebastian exasperated.

"And why not, missy? You heard, Mrs. Kyle! You're free to express yourself any way you'd like at Lincoln- and you'd have tons of support!." His mom said. He wasn't sure if she was mocking him. He felt sick and queasy hearing his once hidden fetishes be talked about so openly. And missy?

Sebastian's heart, ego, and pride finally had enough. He got up and yelled: "I can't, MOM I DON'T WANT THAT! WHY WOULD YOU EVEN SUGGEST I-"

SLAP! Sebastian had once again fallen to the floor, shellshocked as ever. Tears once again flowing furiously as he couldn't believe this nightmare he was in was reality.

"DON'T RAISE YOUR VOICE AT ME!" His mother spat as he sobbed. "You want to waste your time in class reading about being the opposite gender? Then GO to class as the opposite gender!" "Mo--om, pl-pleaase!!" Sebastian said, trying to beg his mom from being unreasonable.

"It's not up for discussion or debate, MISSY. Starting next school year, Sebastian Berns won't be attending Lincoln High. You'll be going, as the girl you've spent too much time daydreaming about. So why are you crying? You should be thanking me! Unless of course you're crying euphoric tears?" Mrs. Berns said, now with a more noticeable mocking tone.

"Mom, what will people say???? I can't! You can't make me! I don't want this, I can't just call myself a girl and go to Lincoln!" Sebastian said, risking another slap.

This time however, his mom didn't slap him. "Sebastian.. I can make you. And you won't just be calling yourself a girl. You'll be wearing girls attire. You'll be enrolled formally as a girl. And you'll sit your pretty ass down in every class, take notes. Ask questions. Participate fully. And earn all As! And again, I CAN make you. I don't care if you want it or not. Best case for you, this gives you the gender expression you so badly seemingly yearned for. Worst case scenario, it's a constant in-school reminder of how you better be focused!"

"..." Sebastian sat there silently. He wanted to think of a response, but he was too stunned to speak. These fantasies he liked to imagine and read about... they were meant to stay just as fantasies. He never wanted them to be his reality!

"And besides missy, enrolling next year as a girl will give you the perfect hiding excuse, so that none of those regular, non-repeating seniors and underclassmen mock you for being held back a grade! Oh I can't imagine how cruel those boys and girls will be when they find you've been held back at senior year! And then surely word will get out to your FORMER friends!"

Sebastian didn't want to admit it, but this part made a little sense to him. He was worried about his friends finding out about him being a "super senior" next year, but he didn't think about ridicule from underclassmen. Or from teachers! But still, dressing like a girl? "But if I go to school as a girl... won't people make fun of me then too???" "No silly! Because you'll be too dolled up to be recognizable! Of course, Mrs. Kyle will recognize you! And whoever amongst the teachers she decides to tell will recognize you too, but unless you say something to the students yourself, nobody should spot that deep down underneath your dresses, skirts, and pretty pretty makeup is poor old Sebastian Berns, Lincoln Highs resident super senior!" Ouch... talk about cold. But Mrs. Berns wasn't using this harsh language just to make her son feel bad. She wanted it to sink in that he was in trouble. And while she personally wasn't excited at the thought of having her son be a "super senior," she was committed to this plan of hers. Like she explained to her son: Best case for him, this gives Sebastian the gender expression he was reading about. Worst case scenario, if he truly was just a perv all along, it's a constant in-school reminder of how he'd better be putting his all in his studies.

"Do I make myself clear?" She asked.

"Y-..."

...

"Yes ma'am." Sebastian said, hanging his head in defeat and solemn. Maybe he should've fought back some more, but his spirit was too brittle after the course of this very draining day.

"Good! Because that settles NEXT year. But there's still the matter of this semester." She told him. "Now it's already been settled that you are to no longer have ANY social interaction with your friends. At least, not until you finally get your diploma next year. And while your academic career in girlhood won't start until next school year, every day after school THIS year, I expect you to be in women's wear. It'll be perfect practice for next year." Sebastian was too numb to even say anything anymore. He just sat there silently listening on, as his mother explained his unwanted wardrobe changes.

"Starting Monday, every day after school you are to immediately come home, and change into female clothes. This weekend I'll go shopping for what fits you, as well as buy you a makeup kit, and other feminine needs as you explore your girlhood. After you're done changing, you'll work with me to learn how to do your makeup, you'll do your chores, and you'll get started on your homework and studying for any upcoming quizzes or tests. After you're done, you'll get up, change into boy clothes, for this semester only and the cycle will repeat. Once summer rolls around, you'll be so female-passing, you'll spend 24/7, until you get your diploma as a girl. After graduation, you'll be free to go back to living life as a boy, or you can seek transitioning fully, or you can do a bit of both, I don't care. As long as you are college bound, whatever you do afterwards is fine with me. Do I make myself clear?" "yes ma'am." "good. Now go upstairs and don't come out for the rest of the night. And Sebastian, if at any point you give me defiance, and demand you don't want to follow through? You'll be left houseless. So good, in this economy no less, finding a job without a high school diploma to make enough to pay rent, as you study for the GED. Then good luck explaining to colleges that you not only failed your senior year, you dropped out of retaking it." Mrs. Berns said, warningly.

"Fuck..." Sebastian thought to himself. He felt too defeated to say anything today, but these last words of his mother essentially squandered any hope he'd have in the coming days to talk her out of this madness.

With nothing else to say, Sebastian once again said "yes ma'am" to his mother, and made his way upstairs- sobbing himself to sleep.

Chapter 4:

The following day was Saturday. And unfortunately for himself, Sebastian barely got any sleep. He woke up early that very Saturday and silently got himself ready. When he went downstairs he saw a note on the kitchen table. "Seb,

Went to the mall to buy you some things.

Get started on your homework.

-Mom." Sebastian's stomach dropped out of fear of what his mom would be bringing him. He tried not to dwell on it too much, and decided to quickly freshen up, eat some cereal, and obey his mother and do his homework- not just use AI chatbots to do it for him.

"Maybe if I just play along diligently for now, mom will drop the crossdressing mandate she's putting on me." He thought to himself.

Hours passed, and Sebastian made some real headway into his homework. His mother came back sometime around 6pm, with bags upon bags of things.

"Sebastian! Go into the car and pick out the rest of your items." Mrs. Berns called.

"Okay...!" Sebastian replied as he trudged to the driveway. Sebastian picked up the bags, closed the car, and went back to the living room. To his confusion, however, his mother wasn't there.

"Mo-om?" Sebastian called out.

"Mooooom!" He repeated, as he went upstairs looking for her.

"Come up to your room! Bring all YOUR new clothes with you!" His mother cried out.

"MY clothes." Sebastian thought to himself. "Surely this will just last a a week or two, and once she sees how much I DON'T want this, she'll drop the whole thing and I can do my repeat of senior year online."

...As if!

When Sebastian arrived upstairs to his room he was floored. On his bed was piles and piles of clothes. Blouses. Jeans. Skirts. Dresses. Leggings. Even bras and panties.

"Whatthe... mom what the f-"

"LANGUAGE!" His mother warned. "It's bad enough you're getting F's in school, I don't need you dropping f-bombs too, missy!"

"Now, THIS (pointing to all the outfits laid out on the bed) is just the START of your new wardrobe. We'll definitely be adding more to it as we arrive closer to the next school year."

"MOm Pleaaaase! You can't make me do this!" Sebastian whined.

Unfortunately for Sebastian these whines fell on deaf ears.

"Well, MISSY. I thought you failed Senior year because you were a slacker. I didn't realize you were STUPID too! Didn't I warn you yesterday if you complain or resist you'd be put on the streets? I have no interest allowing a failure of a son living under this roof- now a studious daughter on the other hand? I'm willing to make that work."

...

"And besides! I thought a pervert like you would be thrilled?"

"IM NOT A PERVERT MOM, PLEASE!" Sebastian cried.

"Oh then are you trans, sweetie? Because why else would you stoop to reading your gender nonsense in class? Which is it?"

"I-I-i don- i don't" Sebastian was at a loss for words. He was too embarrassed- if only the floor could swallow him up and free him of this seemingly permanent embarrassment.

"Speechless, no surprise. Now let me reiterate: If you were a regular 18 year old, you wouldn't be in this mess. We'd be sitting at a nice restaurant right now talking excitedly about your plans for college.. but that's not the case. So either comply by my household rules or get out! I won't hesitate to call the police on you, if you continue to defy me you know? Legally, I have no obligation to keep a slacker like you under my roof. Do I make myself clear?"

With tears streaming down his eyes, Sebastian nodded in compliance.

"Good! Now before you get acquainted with your new wardrobe, I want you to take another shower, and I want you to shave your arms, legs, nether region, and of course face. Be completely smooth, and as you do that, I'll pick out your first outfit of girlhood! Knowing you, you must be so excited."

He wasn't. (At least not yet..) while yesterday's traumatic events led him to realizing he should expect this forced entry into girlhood sooner or later, he didn't expect it to start today. Not knowing how to answer, Sebastian started stammering again, before his mother cut him off.

"Just hurry up and get in your shower. I'll leave your outfit on the chair, and when you're ready meet me in the living room., I expect you back downstairs in say 90 minutes. And don't forget: ZERO. Defiance." Mrs. Berns said, handing Sebastian a pink razor and shaving material.

"Yes ma'am, Sebastian said, taking the items. As he got in the shower after stripping, Sebastian thought about the rest of this school year. "I just need to play along... for now. There's no freaking way she'd send me to school... as a GIRL!" These thoughts seemed to put Sebastian at somewhat for now. "Maybe when this dies down, I can look into how to register for the GRE. Then after a stint in community college, I can transfer and it'll be like nothing ever happened.

Sebastian wrapped up the shaving pretty quickly. After a few minutes, he had shaved his face (he never could really grow hair on his face anyways), his body, legs & arms were completely smooth. After washing up, Sebastian dried himself off, and braced himself for the outfit his mother left for him.

In his room, besides the heap of clothes laid out on the bed, on his chair was a white, long sleeved blouse with light ruffles with black buttons and a slight Peter Pan collar. Alongside it was a black knee-length skirt, black tights, and a matching black panties and bra set.

Sebastian's hands trembled as he ran his hand through each of the items. They felt so... soft. To the surprise of no-one, Sebastian started to feel aroused at the idea of putting the clothes on.

Carefully, Sebastian took the bra and hooked it on the halfway hooks, before actually put it on. Immediately it felt overly tight, and after much struggle, Sebastian took it off and hooked it looser, but nonetheless it still felt overly tight. "I hope the rest of my bras fit better... fuck, I can't believe I actually own some freaking bras." Sebastian thought. After leaving the bra alone, Sebastian put the cotton panties on, and immediately became hard from the feeling of his penis against the panties..

"... fuck..." Sebastian lightly whispered. He did want this. He never had the chance to fully admit it to himself, but he truly would have been enjoying all this... had it been on his own terms. Had it been in his private life. Not at the forceful hand of his mother, and to the knowledge of his math teacher and principal.

This was becoming infinitely more confusing for Sebastian. The mix of embarrassment and growing horniness was too much of an internal conflict. Heck, the past 2 days were more turmoil than he'd ever expected to face in his whole entire life. After putting the panties on, Sebastian then pulled on the tights, secretly appreciating how snug they felt, especially around his butt. This is what he always fantasized about... "But I can't... I can't live permanently as a girl!" He thought. "I'll never be able to face my friends... I'll never have a shot with Sarah... I-i-" "Sebastiaaaan! Are you ready yet? You better not be dilly dallying, or else!" His mother called from downstairs.