The Sissy Academy's Valedictorian

I knelt there, my face and body glazed with cum, as a martini glass filled with the combined cum cocktail of ten studs was raised above my eager, waiting mouth. At the same time, a fresh group of ten men surrounded me, stroking themselves as they plotted what they wanted to do with me.

One of the studs from the previous group gripped my throat while slowly tipping the martini glass toward my lips. I gagged as the first pour overwhelmed every one of my senses. The thick, salty cocktail filled my mouth, and I struggled to keep every last drop inside.

"Hold it, sissy," he commanded as my eyes began to water. "I want you to savor it."

I nodded and smiled, swirling my tongue through my mouth to show my appreciation for their cocktail. I gargled it playfully, blowing bubble after bubble as he watched me with a look of complete dominance.

"Now swallow, slut."

I nodded again, closing my mouth and savoring the taste one final time before feeling the combined release of ten men slide down my throat. I opened my mouth, stuck out my tongue for inspection, and smiled.

"Thank you for your cum, Master," I whispered.

He smirked and reaponded "No problem, sissy." He gave my cheek a playful slap and walked away.

Before I had a chance to process the martini, the next group of ten closed in around me. I felt both of my hands guided toward two fresh cocks. My soft hands, coated with glossy milky-pink nail polish, delicately wrapped around each one as I began stroking them. Another cock positioned itself in front of my mouth, and I wrapped my glossy burgundy lips around its thick, veiny shaft while continuing to stroke the other two.

I felt another pair of hands slide across my hips as someone pulled me to my feet and positioned himself behind me. "I want her pussy," he shouted as I felt him push into my already gaping cum filled boy pussy.

There I was, servicing four men at once, with six more patiently waiting for their turn. My flat chastity cage rested against my body while my 500 cc breasts bounced with every thrust.

Total submission.

Total acceptance.

This was my happy place.

My destiny.

My purpose.

But I wasn't always this feminized, cock-hungry sissy.

What now felt like a distant dream. I recalled I was once an ordinary guy named Matt. I had girlfriends, friends, a career in construction, took care of my body, and by all appearances seemed content with my life.

At least... that was true until I joined the Sissy Academy.

Four years earlier, I was a 24 old guy fresh out of college and focused entirely on myself. My life revolved around work, fitness, girls, and an afternoon soccer league I played in.

One of the last truly straight things I remember doing was hooking up with a random brunette I met on a dating app. Whose name I've long since forgotten. We met after one of my soccer matches, grabbed drinks at a bar, hit it off, and ended up back at my place. When I woke up the next morning, she was gone. She must have left in a hurry because she'd forgotten her red seamless cotton thong.

Not knowing what to do with them, I gave them a quick sniff before tossing them beside my laundry hamper and going on with my life. A few days later, I found myself lying in bed, bored and horny, scrolling through porn.

Unable to find anything that really caught my attention in the usual categories, I drifted into the shemale section. There was always something about the taboo that got me rock hard. I had always imagined myself being with women like them, never becoming one.

After a few minutes of scrolling, I stumbled across a video titled Straight Test. At the time, I thought it was just another porn video. Looking back, it was the beginning of the end for Matt.

Curious, I clicked play.

A hypnotic spiral immediately filled the screen. A sultry female voice, reminiscent of Scarlett Johansson, drifted through my speakers.

"Take a deep breath."

"As I count down from ten, your eyes will become unable to look away from the dot in the center of the screen."

10.

A beautiful brunette wrapped her lips around a thick cock.

"You want to be her."

"Seriously?" I thought at the time as I rolled my eyes with sarcasm.

Looking back, I can admit what old Matt couldn't... I did want to be her.

9.

A blonde was being spit-roasted.

"You want to look like her."

Fuck her? Sure. Look like her? I almost laughed.

8.

Another brunette lay spread-eagle, pleasuring herself.

"Aspire to be her."

She looked completely overcome with pleasure. I caught myself wondering what it felt like.

7.

A shemale rode a cock, her own bouncing freely with every thrust.

"Becoming her is your only goal."

By this point, I was already getting hard.

I told myself it was because of the woman.

Not because I was imagining being her.

6.

A shemale wearing a chastity cage eagerly sucked two cocks.

"Chastity can help you become like her."

I'd seen porn featuring chastity cages before, but I never concidered wearing one myself. What would it feel like? Would it hurt? Would I be able to get out? Why was I thinking about wearing one now?

5.

A man slowly stroked his cock.

"Submit to alpha cock."

I'd never watched gay porn before. Shemale videos were one thing... But just a guy? I felt a strange flutter in my stomach. Not fear, desire.

4.

A man was bent over on all fours, taking another man's cock.

"You are a beta male."

I never once considered myself a beta male. I slept with chicks, worked out, I had a masculine job, but I doubted real alpha males even knew that kind of content existed.

3.

A man knelt surrounded by cocks being covered in cum.

"Cum is your only reward."

Girls in porn always made it seem like it was the greatest reward imaginable. I wondered what it might taste like.

2.

A man was being spit-roasted.

"Use all of your holes to pleasure cock."

I'd never been so hard in my life. I began to fantasize how it would feel to have a cock filling every hole.

But wait... that's gay. Was I gay?

I couldn't look away as I began to realize how aroused I was. Every masculine alarm bell in my head was screaming by now. Yet I ignored every one of them.

1.

A gangbang filled the screen. The man at its center was built almost exactly like me.

"Your only purpose in life is to please cock."

I was so aroused I thought I was going to explode. I stared lustfully at the man being passed around like a cheap whore. I wanted to be him.

Then the video changed.

Image after image.

Cock after cock.

Scene after scene.

The hypnotic voice repeated the same phrases over and over.

"Becoming a sissy is your destiny."

"Pleasing cock is your destiny."

"Fulfill your destiny."

I couldn't look away not realizing my tongue was hanging out of my mouth until I climaxed with incredible intensity, shooting rope after rope across my chest and face, some of it even landing against my lips.

Almost instinctively, I licked my lips clean and swallowed my first cum load. It didn't taste nearly as bad as I'd imagined.

In fact, It was surprisingly pleasant. The moment my orgasm faded, however, guilt crashed over me. I caught my reflection in my laptop screen, a strand of cum still hanging from my chin, and immediately cleaned myself up.

When I returned to close the browser, I noticed a message waiting beneath the finished video.

Enjoyed what you saw? Join the Sissy Academy for more videos and personalized training.

I'd never had an orgasm like that before. Against my better judgment, curiosity got the best of me as I clicked the link.

The website loaded almost instantly.

Returning Student or New Enrollment?

I don't know why I didn't simply close the page but I couldn't. Whatever that video had done to me, I wanted more.

I clicked New Enrollment.

A new page appeared.

All new students must complete an entrance examination. Upon successful completion, you may be invited to enroll.

Would you like to begin?

I clicked Yes.

The first question appeared.

Have you ever fantasized about becoming a sissy?

Until a few minutes ago, I'd only fantasized about having sex with them, never becoming one.

No.

The next question loaded.

When watching a blowjob, do you prefer the cock to be small?

What kind of question is that?

Of course not.

I wanted to watch her struggle to take a huge cock, gagging and drooling all over it.

I answered No. Bigger is better.

Almost immediately, another prompt appeared.

So... you fantasize about big cocks?

I frowned.

Well...

If I preferred watching women with bigger cocks, then maybe, in some strange way, I did.

I guess so.

The next question appeared.

Do you own any panties?

"No," I thought automatically.

Then I remembered the thong the girl had left behind. That red thong sat beside my hamper for three days. If I'd thrown it away that first morning, my life probably would've been very different.

Technically...

I did.

I answered Yes.

Correct.

We knew you would.

I froze.

"How the hell did it know?"

The next prompt appeared almost instantly.

Do you like how they feel on you?

I'd never worn panties before, but as I looked over at the red thong lying beside my hamper, I felt strangely compelled to try it on. I picked it up, stepped into it, and pulled it over my hips. Standing in front of the mirror, I froze, holy shit... My ass looked incredible. My years of soccer had given me toned legs and a surprisingly toned ass.

As I admired myself, I felt myself getting hard all over again. If you'd asked me whether I'd ever consider wearing women's underwear a week ago, I'd have laughed in your face.

Three days later I was standing in front of a mirror wondering if red was really my color. I hurried back to my computer.

Yes. I like how they feel.

The response came almost immediately.

Good, sissy.

Another question appeared.

Do you want to feel this amazing all the time?

Without hesitation, I answered... Yes.

The screen faded into a congratulatory message.

Entrance examination complete.

Congratulations. You have passed and may now apply for enrollment into the Sissy Academy. I filled out the application until I reached the section asking for my new feminine name and email address.

I paused.

After thinking for a moment, I typed Melissa. She had been a girl I'd hooked up with in college. A total party girl. Beautiful, carefree, and completely uninhibited. It felt strangely fitting. I created a new email address under the name Melissa, submitted my application, and waited.

Every day I refreshed my inbox, hoping for a response. Finally, two days later... It arrived. My acceptance letter.

Covered in concrete dust with mud still caked to my boots, I opened it right there on the construction site the email began:

Dear Melissa,

Congratulations on your new life.

From this day forward, you will be known only as Melissa as we help train, guide, and transform you into the sissy you've always been, whether you knew it or not.

Our academy consists of a twelve-part curriculum:

1. Foundations

2. Fundamentals

3. Acceptance

4. Fitness

5. Social Skills

6. Lifestyle

7. Beauty

8. Behavior

9. Transformation

10. Slutification

11. Practical Examinations

12. Graduation

Each module concludes with a final examination before advancement is permitted.

Before Module One begins, you must already possess at least one pair of panties of your choosing and one bra. We look forward to guiding your transformation. Lessons will begin immediately.

Sincerely,

Head Mistress Alyssa.

I stood there, confused, aroused, and unable to stop thinking about the woman in the video. None of this made any sense. Just this morning, I'd been an ordinary guy. Now I was standing on a construction site under the name Melissa, waiting for lessons from something called the Sissy Academy.

My phone buzzed with another email. I looked around to make sure no one was watching before opening it.

The subject line read:

Module 1: Foundations.

I swallowed then I tapped it open.