The Law Department Wants to Date
Tuesday, October 21st. 10:58 AM.
I flipped through the exam paper and let my pen glide across the page without hesitation.
From every corner of the lecture hall turned exam room came the sound of pens pressing against paper, the pressure varying with each stroke.
Scratch, scratch. Scrape, scrape.
Nearly fifty students were all rolling their pens across their answer sheets at once, filling the room with a strange white noise that I was also contributing to.
An hour had passed since the exam began, yet not a single student had finished and left.
Who would claim the gold medal this time?
I had barely managed to solve up to question eight, but my hand froze at question nine.
[Question 9] Predict the product of the following reaction and describe the reaction mechanism step by step. (10 points)
When an anisole derivative with an -OCH₃ substituent at the para position on the benzene ring undergoes bromination under Br₂/FeBr₃ conditions, (1) draw the structure of the major product, and (2) explain which factor determines regioselectivity when the directing effects of electron-withdrawing and electron-donating groups conflict, using resonance structures.
I really had no idea.
It wasn’t even that difficult. It was standard material we had definitely covered, but because it wasn’t in the past exam papers, I hadn’t memorized it.
I had somehow managed to answer questions one through eight.
I had written out the basic nucleophilic substitution reactions and the E1/E2 mechanism comparisons exactly as I had memorized them, and the aldol condensation product predictions were similar enough to the lecture notes that they hadn’t been too hard.
But this one? I had no clue.
I knew the methoxy group was an ortho-para director, but if something was already attached at the para position, where would the new substituent go? Ortho? What about steric hindrance?
My head started throbbing.
I stared at the question while twirling my pen for a long time, but no answer came to mind.
Frustrated, I glanced around the room.
Fortunately, I wasn’t the only one struggling. Other students were also groaning and spinning their pens.
The guy in front of me was clutching his head, and the girl next to me let out a heavy sigh while staring at the ceiling.
At least I wasn’t the only idiot. That gave me a small bit of comfort.
Applied Organic Chemistry
The subject was written on the blackboard at the front.
It was in the professor’s illegible, squiggly handwriting.
The characters were so messy I could barely tell if it said “organic” or something else entirely, and the reaction schemes he wrote during lectures were always like that, forcing me to struggle just to decipher them.
The exam time was also written in small letters beside it.
10:00–12:00. There was still a full hour left until the end.
I stared at question nine again. “Explain using resonance structures…”
The methoxy group’s lone pairs resonate into the benzene ring, increasing electron density, which makes the positions favorable for electrophilic attack…
Ah, I don’t know. I’ll just write whatever I can remember. I need at least some partial credit.
After scribbling down what little I knew, I raised my right hand and called over the teaching assistant who had been assigned to proctor the exam.
She was a senior I recognized, though I didn’t know her name.
I had seen her a few times during lab sessions, but she always wore glasses and had a blank expression, making it hard to strike up a conversation.
“If you need the restroom, flip your answer sheet over and…”
“No, I’d like to submit it.”
“Ah, alright.”
The assistant took my answer sheet, checked my student ID number, and nodded.
I stood up, grabbed my bag, and slipped out through the back door of the lecture hall.
As soon as I submitted my poorly written answers, other students began raising their hands one after another, calling the assistant over.
These bastards had been watching me. They were waiting to see who would leave first.
Applied Organic Chemistry—the final midterm exam.
The gold medal. And a miserable defeat.
I entered the club room and collapsed into an old chair.
I pulled my laptop out of my bag, turned it on, and opened the lecture notes PDF the professor had uploaded.
Comparing the uploaded notes with the exam scope one by one, I tried to recall the answers I had written earlier.
The key terms the professor had probably wanted us to include seemed to have completely missed the mark, but my overall direction hadn’t been completely off either.
Since the general context and logic didn’t stray too far from what we had covered in class, I figured that with a bit of luck I might still manage at least a B+.
But that was all.
This midterm had been disastrous.
My GPA, which had been hovering in the high 3.0s, was now guaranteed to drop into the mid-3.0s.
The grades I had maintained steadily before my military leave had collapsed in a single semester.
It was all because of my little sister and Jang Eunbi. That wasn’t an excuse—it was the truth.
After the power struggle with my sister began, I had caved within a week and gone to her room.
I told her I couldn’t take it anymore, that I would do anything, and begged her to show me some mercy.
But she had simply said, “Try holding out for just one more week,” and that had already happened six times, meaning over six weeks had passed.
Our positions had completely reversed from when she used to sneak into my room to torment me. Now I was the one going to her room every evening, begging her to unlock the chastity cage.
Yet she never unlocked it. Instead, she spent an hour kissing me or fondling my balls and nipples, tormenting me.
Even that was enough to make precum leak steadily from the cage, but it was nowhere near enough.
I wanted to be touched. I wanted to come like a man.
I was certain that if someone so much as rubbed my cock for five seconds, I would gush like a faucet.
After she interrogated me about whether my cross-dressing hobby had been a lie, I had no choice but to learn how to do makeup from her.
From base makeup to drawing eyeliner and applying lipstick.
She had been surprisingly thorough in teaching me, though I couldn’t tell if it was genuine kindness or part of a plan to make me into a more perfect woman.
She seemed to have vaguely noticed that I disliked cross-dressing, but she pretended not to and kept forcing it on me with lines like, “You weren’t lying to me, were you, Oppa?”
Maybe she had simply gotten addicted to dressing her big brother up as a girl.
She had handed over all the women’s clothes she no longer wore, along with the underwear she had worn since middle school.
Along with the warning, “You must never throw them away, and you have to wear them every day,” and the comment, “They probably suit you better anyway.”
Twenty bras, thirty pairs of panties, ten pairs of stockings.
Every single one carried my sister’s scent, with loose threads or missing ribbons—old panties that made me wonder why she had kept them for so long.
She was probably using this chance to give them all to me while buying herself new ones.
Jang Eunbi was another problem.
Even during exam period, she kept coming to the club room, holding my hand or sitting right beside me.
Telling her I needed to study was useless.
She would bring women’s clothes—dresses, blouses, miniskirts—and force me to wear them, then make me buy them from her afterward.
The one saving grace was that she no longer demanded money the way she used to. Instead, she gave me the clothes in exchange for taking humiliating cross-dressing photos and getting pegged.
Of course, I didn’t want to think about where those shameful photos of me in women’s clothes ended up.
Thanks to her, my closet now contained more women’s clothes than men’s—five times as many—between the ones my sister had given me and the ones Eunbi had forced on me.
Whenever I opened the closet, rows of pink, sky-blue, and white dresses hung inside, while the drawers overflowed with stockings and lace-trimmed panties.
My room no longer smelled like a bachelor’s; it reeked of perfume and makeup, to the point where I sometimes wondered whether it belonged to a man or a woman.
The vanity was lined with foundation, eyeshadow palettes, mascara, and lip tint, and a faint feminine fragrance lingered in the air.
I needed to clean everything up before my parents returned from their overseas business trip, but I had no idea when that would be.
Under these circumstances, it was impossible to focus on studying in the first place.
Even when I sat at my desk with my major textbooks open, the words refused to sink in.
When I tried to memorize reaction mechanisms, other thoughts kept intruding. Even while studying, I would suddenly feel pain from the chastity cage.
After more than six weeks without touching my cock, I was on the verge of going insane. I had long since passed my limit.
Because the cage prevented me from coming, the longer time dragged on, the worse it became. My trapped erection throbbed painfully, and my balls and prostate churned with unbearable heat.
Whenever that happened, I had to clutch my crotch and force myself to breathe.
I took deep breaths, drank cold water, and tried desperately to clear my mind.
But no matter what I did, lewd thoughts returned immediately.
They were burned into my brain, impossible to erase no matter how many times I tried.
The faces of the two women alternated, taking over my thoughts, and my concentration hit rock bottom.
Still, there were times when Jang Eunbi pegged me in the club room and I came like a woman just from having my ass stretched, but even then it only squeezed out prostatic fluid and precum. Thick semen never came out properly.
Looking back, even the first time I was pegged, even when I came just from having my ass spanked, even when I orgasmed from nipple stimulation alone—I realized now that it had all been prostatic fluid, not real semen. At the time, I had mistaken it for the real thing.
But once the cage was locked on and I came only from anal stimulation, that unsatisfying, incomplete feeling—that nothing had actually been released—made my body understand that it hadn’t been real ejaculation.
Apparently, without touching my cock, it was difficult to actually expel real semen.
Or perhaps if they kept developing my ass, I really could learn to come from just my prostate and nipples… but I absolutely did not want that.
I couldn’t bring myself to beg Jang Eunbi or my sister to train me that way.
Still, if I kept getting my ass stimulated by Eunbi’s strap-on like this, my prostate would eventually develop on its own, and coming from anal alone would only be a matter of time.
Without the chastity cage, coming from anal would probably be easy, but because it prevented erections, it wasn’t simple at all.