The 5-Day Plan

CONTENT WARNING: This story contains the following: abuse of power; the use of drugs to make someone more compliant; bdsm; genderbending. These themes may be triggering to some readers so please heed the warning if you are upset by this sort of content.

This story also has some elements that are a bit fantastical and not 100% based in reality. I realize some of my themes may be getting repetitive, so if you're bored of hearing similar descriptions I'm sorry about that (I just write what turns me on). This one is sort of long but I jerked off at least 20 times while creating it so I hope you enjoy reading as much as I enjoyed writing. :)

All characters are above 18 years old.

***

Day 1

From the moment he walked into my office I knew he would be mine. The boy who had just entered was taken straight from my fantasies. He was the prototypical waif; a nymph. This perfect creature, who was just placed directly into my lap, was soon to be mine, and mine alone forever. But he didn't know that yet.

This particular pupil, just 18 years old, is a charity case. His mother is a cook at the peculiar higher learning establishment that I head and she begged me to allow her son entry. When she first asked, I scoffed, wanting her to think her son didn't have a chance. This would be true under normal circumstances, but lucky for him I had more sinister motives.

I told the boy's mother that, 'yes, he can join our peculiar school, but I will be watching over him carefully to ensure his proper deportment'. She thanked me profusely for giving her child this otherwise unattainable opportunity and I knew my trap was set.

Before diving into this story that takes place at our higher learning establishment I must first inform you of how this institution functions.

Our school is an adult 'finishing school', so to speak. A school at which members of each gender can attain the skills and mindset needed to properly excel in their defined role. The school is split into two sections:

Girls learn the craft of homemaking, child rearing, and submission; Men are trained in maths and sciences, sport, business, and dominance. The two sides rarely mingle except at school-sanctioned, formal events. Ultimately, we hope for our students to meet their life partner at our institution, and for the two to live together in marital harmony as we believe it should be. This of course means the strict and devout submission of a wife to her Husband.

When the poor boy's mother pleaded for his acceptance I knew he would not be the correct fit. At our first meeting, when I fell in love, I deduced that his lithe, graceful features and feminine mannerisms did not fit the mold of our male student body. But my perverted, sadistic mind was working overtime and I was going to allow whatever necessary in order to spend more time with him. To understand him. To mold him. To plant my seed within him and watch it grow. And ultimately to love him.

When the boy walked into my office for a quick meeting before his first day of school he looked anxious. He was swimming in the ill-fitted suit that had been sent as his uniform. The men of our institution boast admirable frames and we run our sizes only in larges. Of course I knew this when I sent the boy his uniform, but this was all part of my plan. I wanted the boy to feel uneasy in typical men's garb. I wanted him to recognize his discomfort as a man.

"Hello, boy. I see the uniform came in. Doesn't quite fit you, does it boy?"

He shuffled nervously and looked down. "Um no, sir. It's a bit big, I guess..."

"That it is, boy. I should have known when I sent it that little waif like you can't fit into a man's suit." I needed to reinforce his masculine deficiency.

"I guess not sir..." he trailed off.

"Today is going to be a trial period, boy, do you understand? I'm still not sure this school is the correct fit for a boy like you," - I made sure to emphasize 'boy' - "but we can't be sure until we try. Here is your schedule. You are to report to all of your classes on time; you are not to be a minute late. You are to pay attention and do your work, and you are to perform with exceptional marks if you expect to remain at our establishment. Do you understand, boy?"

I was still seated at my desk and he was standing a few feet to my side, shifting nervously from one foot to the other like a ballerina. I wanted to whisk my little pixie away and lock him in my house right then, but I knew this process had to be executed in fastidious fashion to ensure I claimed a willing prize. I could take the boy now if I desired, but I wanted him to like me, too. And I had an inkling this one was a little light in his loafers.

"Yes, sir, I understand. I'll do my best, sir, I promise." He could still barely meet my eyes. He instead gazed at the floor like a virgin angel.

Finally I stood. Though I had set a precedence as a firm and authoritarian leader, I also wanted to woo my little flower. It's true, I'm a romantic at heart. Sometimes I just show it a little differently.

I walked behind the boy and placed my hands on his slim shoulders. We were located near a mirror and could see each other, my 6'6" frame towering over my little waif. I massaged him.

It wasn't a friendly massage. It was a sensual rub; a naughty rub. It was brief but by the end I watched the boy squirm and shudder while he tried to hold in moans. I saw him pitching a small tent, a mere teepee, in his oversized pants. I, too, felt my length rising, though the tent it would pitch at full mast could accommodate a small village.

The preliminary bell rang signaling 5 minutes until first period which saved me from opening my little flower right there. With one last squeeze I sent the boy on his way and told him to report to my office immediately after classes to debrief and evaluate his future.

I set the boy up with a brutal course load that he would surely fail. I had him in advanced economics and physics, as well as football and basketball. He would undoubtedly come back from the day exhausted and defeated; exactly how I wanted him.

He trudged in a few minutes after the final bell looking beaten and worn out: his hair out of order, his papers strewn about his book bag, his large overcoat slipping off his delicate shoulders. I wanted to comfort and protect him, to tell him that it would be ok, but this wasn't the time. He needed to endure a bit more humiliation to drive home the point.

"Boy, you look a mess! I take it the first day wasn't easy?" I cocked a knowing but stern brow at him.

He looked close to tears.

"No, sir, it was ok... some of the classes were kind of hard, though..."

"Your professors told me you were late to almost every class and that your marks were abysmal." His shoulders dropped even lower.

"How will you ever succeed at this university if you cannot even complete basic calculus!" I was faking anger so he understood the severity.

"Sir it's just so hard," he was quietly crying now. "I don't understand any of the classes, and during sports I was so afraid to play. The men were so much bigger than me and none of them wanted to pick me for their team." He looked ashamed. I savored every second.

"Well, boy, is it surprising that someone like you, someone as soft and sweet," - I emphasized 'sweet' to make him feel a little better - "as you wouldn't do well in those hard classes?"

"No I guess it's not, sir..." he replied sheepishly. He must have known he wasn't quite like the other boys.

"I'm very disappointed in you, boy. I had high expectations of you and you let me down. You've been a very bad boy. As your counselor at this university it's my job to keep you on the right path, but it seems like you aren't even trying!"

"I promise, sir, I am trying!" he cried.

"Well the results speak for themselves. I'm not sure what I'm to do with you, boy. You've been so naughty, it doesn't seem right to let you go without punishment."

"But, sir!"

"Silence! You accepted my offer to attend the university with the understanding that I was to watch over you during your stay. Now if you want to remain here you are going to obey me without hesitation, always! Do you understand, boy?" I was close in his face now, standing over him to show off my size.

"Yes, sir, I understand," my angel squealed out.

"Now, boy, the ways we punish here may be different from what you're used to."

This was somewhat true. When the girls needed to be corrected we used corporal punishment. This was maintained by a team of men's school prefects who would monitor the girls at all times for dress code, deportment, courtesy, and other various metrics to measure feminine virtue. The men simply got detention.

But this boy was about to have a special punishment session with me that was not going on the books.

"Boy, if you want to stay at this establishment you will have to accept my punishments with gratitude and submission, whatever they may be. Do you understand me?"

"Yes, sir..." he was trembling. He didn't actually understand, but he knew he couldn't say no. He couldn't ruin this opportunity. I relished in my power.

"Good. Then the first step is for you to get out of that silly clown costume and down to your little briefs. It's a shame to see you covering such beautiful legs in that baggy frock."

He looked petrified but also blushed coyly at my smooth compliment.

"Boy, I will not ask you again. Did you already forget what I told you about obedience?"

"I'm sorry sir, I'm so sorry..." he scrambled to disrobe.

Once in his socks and briefs I soaked in the view. The golden skin painted on his slight musculature radiated a luminous aura. His tiny bulge was barely making a dent in the oversized pouch of his briefs, but his pert behind filled the back snuggly. The perfect pussyboy proportions.

I took a seat on the large leather chair in my office and beckoned the boy to my lap. "Come little one, it's time for your punishment."

He shuffled over quietly. I could tell by his virginal reservedness that this was his first time being naked with a man. God, he was so bashful and cute. Does it get better than this?

I would soon find out that it does, in fact, get better than this. Much better.

"Come, boy, lay across my lap. It's time I correct you, isn't it? Offer yourself to me for your punishment, little one."

"Yes sir," he said in defeat.

Touching his silky skin as he laid across my lap made me turgid. He nestled into my lap and I took his slim wrists in one hand. Both fit perfectly in my grip, just as they should.

"Boy, I'm going to administer a spanking now to correct your behavior. This will help you understand why the men's school wasn't the right fit for you today." He probably didn't quite get what I meant but that didn't matter to me.

I gave him some warm up swats before really beating the boy into submission. I administered a dozen or so smacks over his covered rump and the boy still hadn't cried. That wasn't going to work.

"Sir!" He squealed when I pulled down his briefs in one swipe.

"Quiet, boy! This is for your own good!" I was trying to hold back my hunger but seeing my handiwork on his glorious globes made my cock throb.

I continued raining down a shower of palms onto his bouncy bum. After another few dozen I knew he finally broke when I heard a small cry and watched a single tear fall from his aquamarine eyes.

"Shhhh," I soothed. "It's ok to cry. That's why it's punishment, boy, it's ok."

Do not misconstrue my above kindness for acquiescence. His tears did not stop me. In fact, they reinvigorated my lust and confirmed that the punishment was working.

He kept crying and even pleaded with me to stop but I remained stoic. This was the most important punishment of all. The punishment that would break him beyond self-repair. He would need me to put him back together.

After another 5 minutes his cheeks were as red as I needed them to be (I don't like to mark my boys too hard) so I slowed down and rested my hands on his bum. He reached his hands back to grab his smarting tush but I returned them to their place.

"Shhhhh, boy, no touching. Just let me make you feel better. It's okay, boy. You did so well. You're such a good boy."

I needed to soothe my boy now. Boys need comfort in times like this, not humiliation. I needed to let him know I wasn't mad. That I didn't do this out of anger, but out of love. I did it because he needs it. And because I can.

"It's ok, boy. You're okay, baby." Shit. I didn't mean to let 'baby' slip out already but he's just so damned cute it's hard not to!

His tears seemed to be slowing and he actually started to look content in my arms. "Shhhh. See, boy, I'm not mad at you. It's ok... You're ok... I needed to do that, baby. It's for you're own good. It's ok, boy. Shhhhhhh..."

He nuzzled into me as I continued to knead his soft ass. Upon pulling apart his cheeks I saw the most darling little hole I'd ever laid eyes on and decided I needed a touch. I slowly grazed my index finger up and down his crevice, feeling every wrinkle and fold on his tight pucker.

"Ooooooh," he let out. He blushed at his own exclamation but it didn't stop him from sticking his butt up higher when I started to pull my finger away. Oh yeah, this boy was mine.

I went back and gave him what he needed: more light strokes across his entrance, tracing lines around my freshly claimed orifice. I felt his small cock stiffen as I caressed my boy's hole. Now sated, it was time to explain his new role at our institution.

"Boy," I rubbed him softly, "We need to talk about your staying here." After the brutal spanking I'm sure he was in no mood to speak but I didn't care.

"I'm not sure how you can attend our university if you can't succeed in these courses," I continued gently. "I'm afraid I'm going to have to revoke your admission, boy."

"Nooo sir, please, sir please,..." he cried quietly. "Please, I need this opportunity. It's the only thing I have and I won't be able to face my mother if I lose this. I'll have nothing left!" Exactly what I want.

"Boy, I'm just not sure I can do it. You aren't the right fit for these men's courses. You're just too delicate. Look at how you cried over my lap just now. And from just a few light spanks. No man would cry like that."

The spanks were actually quite hard and could probably have broken a few good men but I needed to gaslight him further.

"It's not right to have you in those classes, sweetheart, I couldn't do it. I wouldn't want to see you suffering." I stroked his body to comfort him.

"Please, sir, there must be something I can do. anything, please, anything..."

"Well..." I paused. "There is one thing..."

The boy's ears perked up. "Really? What is it, sir? Please tell me, please!"

"Well, I'm not sure if you will like it. And I'm not even sure the rules allow it..." - Bullshit. I make the rules - "but, there may be one solution. We may be able to change your course load, to make it more appropriate for a boy like you. Do you understand?"

He nodded like he did but he couldn't possibly know what I meant. "You have to understand, though, that if we change your work load and put you into courses that are better suited to you, they would be the girl's course. They'd be classes like ballet, home economics, sewing... learning submission..." I let the thought hang so he could ruminate.

"Well, those don't sound so bad, sir... I always have liked cooking... And I'm really flexible and can even do the splits!" he said proudly, not knowing just how much blood his mental image sent to my cock.

"Yeah, boy, do you think that might be something you'd like? I think the classes would be a really good fit for you. You would take to them so well and get really good marks. And once you've learned how, I might even let you cook me something! Wouldn't that be nice?"

"Oh yes, sir, yes I would love that so much!" He gasped in embarrassment at his own joyful outburst imaging our future fraternizing, but I loved it. It made me feel warm inside. The boy still wanted to see me even though I had just brutally spanked him. My plan was working flawlessly.

"Good. We'll put you in a trial period for your new courses starting first thing tomorrow. I think you are really going to love coming to understand your new role, boy."

"Yes, sir, I do, too. Thank you so much, sir! Thank you, thank you!" He looked like he was about to jump up and kiss me. I wished he had, but a man must be patient to reap the full benefits of what he has sown.

"Boy, there are a few things we need to do before you can understand your new role. First, I'm going to be changing your uniform into one more appropriate for a boy like you."

This new uniform, my dear readers, was not the girl's uniform of a short pink skirt and white blouse (although that may be for another story). No, this outfit was a hybrid, a mix of both the masculine and feminine, which is exactly how I saw my angel.

It was a pair of short light pink khaki shorts (to match the pink skirts of the girls), a tight short-sleeve cotton polo, a pair of dainty lace-trimmed ankle socks, white girls' sneakers, and to top it off, white lace panties.

I handed him the uniform in a suit bag and told him not to open it until tomorrow. I didn't want to scare him off, and by the time he saw it the next morning it would be too late to drop out. He redressed in his floppy suit, the last time I would see him in such coarse, masculine fabrics.

Once dressed I pulled him in for a hug; he'd had a long day. We hugged and I squeezed him tightly so he knew I was his protector. He sank neatly into my arms and lay his cheek on my pec.

"Boy," I started softly, "You are to go immediately to your dorm and straight to bed. No dinner." I didn't want my little waif to eat carelessly.

"You will report to my office tomorrow morning 30 minutes before classes so I can give you your schedule and evaluate your uniform. I expect you to wear everything inside this bag and to not make a fuss about it. Additionally, you will shave everything, and I mean everything, below your eyebrows. Not a hair left, boy, do you understand?"

He looked like he wanted to say something but he knew he had already given himself to me. "Yes, sir, I understand," he conceded meekly.

"Good. Now remember boy, straight to bed after this. Nothing else. Nothing!" I gave his still hard cock a squeeze through his pants which made him yelp. In his innocence I'm not sure he recognized the subtle undertone of my grope, but I was trying to make him understand he was not to touch himself. My boy was to stay pure. I assumed he got the message. Plus, a prude boy like him doesn't masturbate often.

"Run along, boy. I will see you at 8:30AM sharp! Do not be a minute late!" I patted him on the back and looked him in the eyes. "I can't wait to see you in your new uniform, my sweet boy." With that I gave him a peck on the top of his head and shooed him out the door.

I needed to jack off, ASAP.

***

Day 2

We are now entering Day 2 of my 5-Day Plan. This is a process I have been planning, crafting, honing, the past few years since I realized I needed a life partner.

I've always loved submissive, slightly feminine twinks, but many of them are whores and not wife material. That's why I created this plan; to lure in the perfect mate. And my prayers were answered when boy entered my life.

When he arrived at my office this morning he was a bundle of nerves but he looked fabulous. His slim body fit the new clothes perfectly and his smooth legs looked endless in the shorts. A hint of his plump cheeks peaked out of the bottom of the khakis and I wanted to take a bite right there.

"My boy, you look scrumptious! I hated seeing you in those drab rags yesterday. This outfit suits you much better, don't you think? You look lovely now, my little peach." Maybe I was doting on him too much but it was hard to resist.