The Sissy Academy: Module 1

I nervously clicked open on my first email labeled Module 1: Foundations. My heart sank as I saw in big pink bold letters.

"Melissa, I know you did not acquire required the garments you were instructed to obtain before opening this module.

You have failed to follow a simple instruction.

Foundations determine the strength of everything built upon them. A weak foundation cannot support meaningful progress. I do not advance my students until they have demonstrated discipline."

How could it possibly know I didn't own a bra yet? As if the email was reading my mind the email continued on.

"Your first lesson will now include a corrective assignment.

I expect better from you.

Disappointedly,

Head Mistress Alyssa."

Internally panicking I quickly shut the email and went back to work. I finished out the day consumed with the fear of Head Mistress's upcoming punishment, simultaneously trying to figure out how could it possibly know I didn't own a bra yet. Once at home I got online and looked for a bra. I'd never shopped for a bra before, and I didn't even know where to begin with sizing. I knew one thing for certain though I would never go into a lingerie store to have a worker measure me. (or so I thought at the time) I scrolled very aroused through the online catalog and decided to get a matching red lace bra to match my red thong. I saw on the site that they had a buy one get one sale and just couldn't pass up the opportunity. I added another matching set this time in pink and checked out.

Aroused at just the thought of wearing the lingerie I slipped on the red thong and immediately began masturbating. After cumming I quickly came to my senses and felt a little disgusted with myself in the moment. I slipped them off showered and forgot about it all till the next day when my package arrived at my door.

Holy shit! I hope my neighbors didn't see the black VS labeled package sitting outside of my front door all day while at work. I rushed into my house, and checked to see if the coast was clear. My neighbors were nice people but they knew I was single, and the wife would've definitely recognized the packaging. I peeped out of my window to see if their car was in the lot thankfully I didn't see it. Relieved, I turned my attention back to the package. Immediately I felt that same arousal from yesterday creep back in. I rushed into the shower, cleaned myself up, ripped open the package, and stood there in disbelief. In front of me lay two bras and a brand new pink thong all neatly packaged... for myself.

My mind was swirling, why did I waste money on this, why was I so aroused? why was I curious how it felt on my body? I slipped into my red thong, clasped on my brand new bra which fit perfectly aside from the missing breasts. And stood there in awe as I stared at myself in my mirror. A million things are processing at once, but all I can think of is how amazing this feels. I look for the Academy's email and find a new Module 1 foundations email waiting for me. I clicked it open and read.

"Hello sissy, attached is a link and instructions for your first lessons and punishment. Per my previous email disobedience will not be tolerated and I expect my sissies to follow my every instructions. Click on the link and begin your training."

I clicked on the link and opened it to find a metronome and 10 videos all titled to play them. At the top of the email gave the instructions.

"Melissa, attached are 10 videos you must watch in succession 1 for each day. While watching the videos you are required to wear your bra and panty. You must follow the instructions of every video and stroke your clitty to the beat of the metronome. As your punishment you are not allowed to cum while watching these videos and will not be allowed to cum for the next 10 days. Any break in the rules will result in higher penalties and punishment. Mistress Alyssa will know if you break any rules, and discipline you accordingly. Click on the first video and begin your new life.

With love and dominance,

Head Mistress Alyssa."

I couldn't wait, I clicked open the first video and heard the metronome begin to tick. The screen started with a spiral counting down from 10. That same sultry voice began to speak.

"Hello sissy, relax and listen to my voice. As I count down I want you to feel more and more relaxed. Inhale, listening to my commands and exhale any lingering thoughts. When I reach zero you will be totally under my command."

As I started to stroke to the beat of the metronome, which was too slow to make me cum quickly I looked at the video and listened to that soothing voice. As if a spell had been cast over me when she reached zero I was mentally frozen in place. Images began flashing. Women getting ready, putting on makeup, doing their hair, and all sorts of other daily girly activities. The voice spoke over the images repeating herself.

You want to be like her.

You want to feel like her.

You want to look like her.

You want to please men like her.

Over and over again till the video ended. I wanted to cum so badly, but I was terrified of the thought that somehow Head Mistress Alyssa would know. Wanting not to get punished worse I closed the video and tried distracting myself the rest of the day.

For the first few days, I'd wake up slip into my lingerie and begin my assignment. The first few days the videos were very similar encouraging me to become like the beautiful women it displayed in all aspects from physical to emotional, sexual and spiritual. I'd have to stop several times throughout the videos to refrain from climaxing and get punished even more severely.

The next videos days four through eight began to focus more on the sexual aspirations I should desire for myself. Showing slow intimate scenes of women making love to men and worshipping their superiority over them. My sexual frustration at this point was really starting to build up. Around the fifth or sixth day I noticed I wasn't rushing to remove my lingerie after completing my assignments and continued wearing them. Something about the feeling of the fabric pressed against my skin filled me with excitement.

The final few videos focused on obedience to the academy and Head Mistress Alyssa. I considered at this point stopping this training and deleting all notions of The Sissy Academy. But that initial shock of being disciplined for something as simple as opening my email too early and not having all of my required educational material had me reconsidering how much freedom I really had. Then again, nobody was physically forcing me to continue. Some part of me was genuinely curious about what came next.

At least that's what I kept telling myself.

By day 10 I'd grown accustomed to the idea of giving myself up to the desires of a higher being having control over my decisions. I surprised myself that I was able to make it the full 10 days without cumming. I don't think I've ever gone that long before. I never felt my balls so swollen before with all the built up pressure, and was dying for release at this point. Anxious for Mistress's next instructions I kept refreshing my emails hoping for any notification. Finally, hours after completing my tenth lesson did I receive my next email. I couldn't open it quickly enough to see what it said.

"Hello Sissy, I hope you've had time to reflect on your punishment, and that was enough to teach you obedience. I'm proud of you for completing your first lesson without any further issues. I must say you looked rather cute in your red bra and panty. Extra credit for getting an additional pink set you eager little sissy."

I panicked, how in the hell did they know I bought two sets and what color they were? Were they watching me through my computer? Did a virus implant itself onto my devices?

I scrolled down the email and felt my life cave in.

A video of myself sitting at the edge of my couch in my red bra and panty stroking myself like a bitch in heat. Repeating the video's mantra. "I want to be like her, I want to feel like her, I want to look like her, I want to please men like her."

What have I done? I thought to myself I'd be ruined if this video ever got out. I continued reading the email.

"By now I'm sure you realized that the academy takes its sissy's training very seriously. The foundation of a relationship is built on trust. Trust that you haven't yet earned sissy. We expect you to trust us with this process, and transformation just as much as you'd expect us not to release this video of you. We won't, we promise as long as you continue to be a good little sissy like you've been these past ten days your secret is safe with us. Although... most sissies end up posting it themselves cheerfully to showcase their growth later on. Until then, nobody but Head Mistress Alyssa will know. As a reward for 10 days of obedience I'll allow you to cum with one exception. You must spin this roulette wheel (link provided) and see what your fate awaits for how, where, and what you must do with your cum. Look for your next lessons in foundations before taking a final exam and moving onto the next module."

With love and dominance,

Head Mistress Alyssa.

Frozen with fear I clicked on the link to see how mistress is allowing me to cum. An image

popped up with different categories and tasks under each category a sign above the image blinking click to spin flashed overhead. I browsed the categories.

Will you be allowed to cum.

Will you wear anything.

What will you cum to.

Where will you cum.

What will you do with your cum.

I clicked on the spin button and awaited my fate.

Will you be allowed to cum?

Yes. (whew that was close.)

Will you wear anything?

Panties bras, and stockings.

(thankful it wasn't any higher I didn't have any of the higher listed items. i didn't own any actual stockings but I had some very long socks from soccer that could count as stockings)

What will you cum to?

cock sucking POV.

(Imagining the POV from the cock sucker and not the guy getting his cock sucked never crossed my mind but the idea sounded so hot)

Where will you cum?

I needed to lay down with my legs and cock up over my face like a yoga plow pose with my mouth open.

(in that position I'd have no way of avoiding getting cum on my face and in my mouth)

What will you do with your cum?

(This is where my heart sank).

I had to catch all of my cum into my mouth and play with it. Scooping any cum that missed my mouth before swallowing it.

I've never fantasized about eating my own, but couldn't help how horny I was. I got dressed, found the appropriate video, and got into position. I found myself staring down the barrel of my own rifle as I tried ever so awkwardly to watch the video but kept finding myself looking back at my throbbing cock. I was pretty flexible and thought maybe with enough practice I could probably lick my own cock. Between the cock in my face and the POV video of girls sucking cock I fantasized about what another man's cock would look like in front of my face.

How it would feel to suck on it.

How it would feel to pleasure it like the girls in the video.

How it would feel to swallow its cum.

I couldn't contain myself anymore. Without warning I began spewing rope after rope of cum trying my best to catch as much of it into my mouth. I was surprised just how much cum I've built up over the past ten days and gagged at the amount of cum in my mouth at first. Not wanting to disappoint mistress I scraped the remaining cum off of my face into my mouth and began swirling it around my mouth. The taste somewhat salty, not bad but definitely not good either. The texture was unmistakable and the smell was an overpowering somewhat chemically smell. Very hard to explain, but I couldn't escape it since it was all in my mouth. I tried my best to make it look appealing but honestly couldn't bear it. After a minute or so though. My initial gag reflexes subsided and oddly I wasn't minding the cum in my mouth anymore. I blew some bubbles and drooled some out before sucking it back up and happily swallowed my load.

When I was finished I looked back to close out the porn, but noticed a green light at the top of my computer indicating a video was being recorded. I closed the video and froze as I saw that faproulette was not only a task roulette, but also a webcam, and I had live-streamed that whole event. I slammed my laptop shut and stared blankly into space shocked to what I just did. How many people just saw that? Did the academy live stream this knowingly or did I unintentionally just out myself? Had the Academy infiltrated all of my devices by this point? Would I have to trash everything, and change all of my information to escape the academy? Even with my laptop closed the livestream kept running and notifications kept coming as if someone altered my settings. While processing what'd just happened, I could hear ping after ping of messages flooding the live stream. I don't want to face the reality of what I just did but I'd need to if I wanted to close the stream. As I sat there pondering I continued to hear notifications flood the chat, and by this point began to wonder just what they were all talking about.

I reluctantly reopened my laptop to a flood of compliments calling me pretty, and how hot that was, how they wanted me to suck them next, and all sorts of other vulgar things. My shame began to fade, replaced by an unexpected sense of pride. They think I'm pretty? Am I pretty? I noticed in my webcam preview that there was a drip of cum still left on the side of my mouth. I didn't want to let my newfound fans down so I seductively took my finger, rubbed my lips with the remaining cum before sucking on my finger and licking my lips clean. The chat was going crazy at this point and they were begging to see more of me.

Even though I just drained my balls I could already feel myself starting to get hard again. I stood up backed away from the camera to show my entire outfit. I twirled around and caressed my body wanting to tease all these people. My eagerness to please was taking over. I grabbed a banana off my counter and got to my knees to please these strangers that I was just terrified of a few minutes ago. I began to stroke myself while sucking on the banana. After a few minutes of stroking and sucking I could feel myself getting ready to cum again.

I got back into the same position from earlier and continued to stroke. I eagerly caught my second load of cum into my mouth. I laid there getting every last drop before sitting back up and showing the camera up close all the cum in my mouth. I played with it more and thanked the chat after swallowing my second load. I closed the livestream and fell asleep from exhaustion without cleaning myself or changing clothes.

I woke up the next morning with the smell of cum still on my breath, and my panties and bra still on. I'd never considered myself pretty so to read strangers complimenting me in such a feminine manner made something change inside of me. I pondered the idea of seeing myself as they saw me last night and imagined how pretty I could be. I checked my email and felt excited to see a new email from the Academy. I opened up foundations part 2 and read the email.

"Hello sissy, Last night was so hot watching you swallow two of your loads back to back. You really are a sissy slut."

I questioned everything again. Did Head Mistress Alyssa start the live stream, or did I just unknowingly start streaming when I rolled the roulette last night? How would she have known I was streaming? And most importantly, SHE WAS WATCHING ME?

"Treat yourself, and buy a dildo to suck on instead of a banana."

(Okay she was definitely watching)

"Also, purchase an actual pair of stockings and a French maid costume to complete the ensemble. You're progressing faster than expected, and will be treated as such. Expect a package from the academy and open it immediately upon arrival. Until then here is your next foundations lesson complete your next lesson and prepare for your final exam."

With love and dominance,

Head Mistress Alyssa.