My Professor's Sissy

I squirmed in my seat, eagerly awaiting the return of our assignments. Intro to English Grammar 101 wasn't exactly the most exciting or captivating class, but it was an unfortunate requirement. Coming back to college after flunking out had been a difficult choice for me, knowing how easily I lost concentration and fell behind in my studies. But, a few years older (and hopefully wiser!), more determined in what I wanted, I felt I was ready to try all this again.

And I had a secret weapon, Rory.

While I had always enjoyed being feminine, crossdressing in secret while I was younger, I hadn't felt as at ease with it as I did now. Finding and accepting that part of me, Rory, had been a world of a difference. Going out to clubs, meeting similar people and friends, it was no longer a shameful part of me, but a joyous and celebrated one. Few things made me happier than nights as Rory.

But my secret weapon, the thing that had helped me through boring classes and lapses in motivation, was my cage. Tiny and pink, soft and fitting perfectly, I had bought many over the years until I found the one I loved. Turning my cock into a cute little clit, eager and straining away, I had the perfect solution to my waning attention.

A simple game, with simple rules. At the start of an assignment, essay, project, or test, I would lock away my clit. The key, safely hanging up in my room, would stay there until I received my grade. Sometimes it was just a day, a little assignment that was completed in an afternoon, the ache barely starting inside of me. Others, like projects or preparing for tests, had been longer, one even keeping me caged for a week. I was in quite the state when I received the final grade, practically running home to my toys.

Professor Sylvia Amber, in her perfectly formed tight skirts, beautiful professional blouses, and constant array of tights and stockings, did not help this little game of mine in any shape or form. Other classes were still frustrating, but none made me whimper quite as much as hers. How could someone so ridiculously beautiful teach such a boring class! How was I suppose to focus when she kept wearing outfits that perfectly rode the line of tantalising and professional?

A part of me wanted to be under her desk, worshipping those legs, spending days doing whatever she willed. A part of me simply wanted to be her, feeling so confident in those clothes, teaching about a topic I knew like the back of my hand. And a small part of me, the more dominant masculine part, wanted to bend her over that desk in the middle of a lecture, fucking all the frustration I had accrued at her hands back into her. But mostly the first one...

While I typically only came to class in a masculine perspective, Rory sometimes bled through the cracks. Polish, mascara, make-up, as well as hidden lingerie I was too scared to show. Each time, Professor Amber quietly complimented these feminine attributes, a sly smile on her face as she walked by, enjoying the hard blush it always brought to my face. Evil woman.

Handing in a simple assignment we had gotten yesterday, I felt my clit strain being so close to Professor Amber. I couldn't shake the crush I had on her, so much about her just screamed out at me, taunted me. I quietly asked when we'd be receiving the mark for them, assuming it would be no longer than a few days. After all, it was an easy one.

"Unfortunately one of your classmates can't complete the assignment right now due to personal reasons, so I've extended the due date to two weeks from now." Smiling, Professor Amber delivered the 'good news' to me, after all who wouldn't want to hear about an extension? My eyes, however, widened in fear.

"T-two weeks?" I stammered, praying I didn't hear her correctly.

"Mmmhmmm" she casually exclaimed, looking down at some notes, missing the terror spread across my face. Two weeks!? Maybe more since that is when the assignment was due, not when it would be handed in. Two weeks...I had never gone two weeks in my cage. Never. One week had nearly broken me, barely able to focus in class, my poor clit a constant straining mess. How was I going to do this? Surely this didn't count, and I had handed in my assignment. But I made a pact coming back to college, knowing I needed something to help me focus. If I broke this one now, would I stay committed later on? What if-

"Are you okay, sweetie?" Professor Amber's hand reached out to mine, tearing me out of the mental spiral I was in. I looked around, seeing everyone else had left, just me at her desk, internally freaking out. Embarrassed, I nodded, thanking her and quickly shuffling out of the room. Her curious expression followed me out of the door. I didn't blame her, the redness in my face deepening at the thought of trying to explain what was going through my head.

That night my clit held me hostage from sleep, aching desperately with the knowledge of what was to come. I groaned, whimpered, curled into a ball, but nothing helped, the image of Professor Amber saying,two weeks endlessly playing over and over in my mind. I put on a pair of silky pink panties, one of my favourites, and simply pouted in bed, praying my excitement waned, and I could get some sleep.

My next grammar class was after the weekend, so far my days locked had moved to five. Certainly difficult, but nothing I hadn't dealt with before. I was constantly aware of my clit, the ache and pressure between my legs never quite leaving me alone. Today I wore some tights under my jeans, Rory's grip over me strengthening the longer I was locked. Outwardly I was just a shy, tall, muscular man. It always made me giggle just how much of a juxtaposition Rory was from that.

Only half listening to Professor Amber go on about verb tenses, still hearingtwo weeks every time she lectured. I couldn't even meet her gaze today, my imagination screaming at me, fueled by my caged clit. Watching her walk back and forth, that confident and commanding tone, captivating all of us for many different reasons. She really was a good teacher, I just was unable to focus on anything but the pulsing between my legs at that very moment.

After class she called me to her desk, saying she needed help carrying things to her office. Internally I groaned, wanting nothing more than to lie down at home surrounded by anything I didn't find exciting. But soon I had a few boxes in my arms, following Professor Amber through the halls, trying so very hard to be respectful, keeping my eyes diverted from the perfect ass swaying back and forth in her black pencil skirt.

Setting them down, I asked if she needed anything else, to which she answered by closing the door. Pointing at an open seat, the office suddenly seeming far smaller with just the two of us in it, Professor Amber sat opposite to me, ensuring she had my full attention.

"I noticed something was bothering you after last class, and then all of this one. Not focused, not joining discussions, very unlike you. What's wrong?" I tried to brush it off, exclaiming I was simply tired. But she was an intelligent and determined woman, and was having none of it. I tried to blame it on the assignment, worried it would affect my grade. But again that was shot down, those piercing eyes holding me captive.

I sighed, knowing I wasn't getting out of here with lies. "I can't tell you," barely a whisper as it left my lips.

"Why not?"

"It's...private."

"Just the two of us in here, I won't tell anyone. Let me help you." Professor Amber's eyes showed nothing but concern and compassion. I did trust her, but this was not exactly 'trouble at home'.

I groaned. "Maybe I'm just a bad student." But that was met with a snort, knowing she was close to breaking me. A tiny whimper escaped my lips as she comfortingly took my hands in hers, waiting. With an exasperated sigh, I relented.

"UGH, Fiiiine! To help with motivation coming back to college, not wanting to flunk out again, I have an...incentive I give myself to finish assignments. And when you pushed the last one back two weeks, it is making that incenvite...difficult." I looked down, blushing harder than I thought possible, praying she left it at that. But Professor Amber was inquisitive by nature, worried about a favourite student of hers, and pressed on.

"Hmmmmmmm. And what is this incentive that would cause you to lose focus in my class?" Those eyes of hers danced, knowing she was close to the truth from the blushing blubbering student in front of her. See the problem with being a sassy brat all the time, masculine or feminine, is when someone can get the upper hand on you, they very much enjoy it. Glaring at my professor, met only with a smile, I could only sigh as it all fell out of me.

I told her about Rory, all the things that came with her, including my cage. Professor Amber asked for the occasional clarification, but mostly listened intently, a slight smirk on her face. I talked about the outfits I'd wear, the nights out downtown, the constant feminine pull after being caged for a while, and the aching need I felt to earn my release. Huffing, pouting at the end of my story, I couldn't look her in the eye as I blushed hard, clitty straining under my jeans.

Squeezing my hands, a subtle sign of support, the smile on Professor Amber's face only grew. While my revelation wasn't much of a shock to her, Rory had often peeked her head up during class after all, the cage and the rules of which certainly wasn't what she had been expecting.

"Well, Rory," that name rolling off her tongue melted me in my chair. "I think it is wonderful that you've found a way to keep yourself engaged in your studies. BUT, if you are going to commit to this plan of action, then you need to find a way to stay engaged during longer periods." Those piercing eyes bore into me, even looking away I could feel them on my skin.

"I know, I'm sorry."

Professor Amber continued her smile, quite enjoying the mindset all of this put me in. Leaning back, she asked a bit more after Rory, what she liked, wished for, and enjoyed. We talked for hours it seemed, feeling more comfortable and relaxed with her. I learned about her wife, how she got into teaching, but mostly the topic of conversation was me, which I was all for. After all, for girls like me, talking about our feminine side comes up oh so rarely.

Needing to get some work done, she walked me to the door, thanking me for being so open with her. Still blushing, but happy to have shared, I told Professor Amber it had been fun talking so freely. She grabbed my hand, saying I was welcome any time in her office.

"And Rory," her grip firm, eyes holding me in place. "Next class I want you front and center, where I can keep my eye on you. After all, you have at least a week until I mark that assignment." I tried to protest, the front of the class was not where I wanted to be, but she shot them down. With a sigh, I nodded, promising to follow her new seating arrangement. Smiling, she sent me on my way, still blushing slightly as I walked home.

True to my word, next class I sat in the front row, right in front of her desk. Professor Amber gave me a knowing nod, mostly ignoring me for the lesson. Being so close to her, watching the nylons of her legs rub together as she walked back and forth, heels enhancing and gorgeous, the tightness of her skirt...how was this suppose to help me focus!? It took everything I had to tear my attention from her outfit, and the aching strain in my clit.

Getting ready to leave with everyone, Professor Amber shot me a look that simply said,stay. I waited begrudgingly as other people filled out, suddenly alone with her sitting on my desk, legs crossed and staring down at me, frozen by the situation. The slightest smile on her face, she asked if I had paid attention.

"Mostly..." I said, slightly giggling. Tutting, Professor Amber quizzed me on the lesson. Quizzed me! Rude. She dramatically sighed at my answers, tutting back and forth, as if nothing I said was right.

"Clearly your mind was elsewhere today, Rory. Ah ah! Hush. Now, since you're struggling with the material, I'm going to have to ask you to come see me this weekend for extra help. I will send you an email with the details. Do you understand, young lady?" I gulped, staring up at her. Picture the hottest professor you've ever seen, wearing the type of outfit you both want to wear yourself, and can't get enough seeing on others, sitting on your desk, holding you captive with her intense, dominating stare.

You show me the person who would refuse that!

Saturday I found myself in front of the address Professor Amber had sent, my poor clit straining away in its tiny, pink prison. The email she had sent had been short, but the final line kept playing in my mind. Three words that had stole sleep from me, my imagination spiraling out of control over the implication of them.

Bring your key.

Nervously, I knocked on the door, greeted by an adorable, tiny woman. I was at least a head taller than her, staring down at the cheery smile on her face.

"You must be Rory!" I blushed, realising this must be Professor Amber's wife, Felicia. She giggled at me, taking my arm and leading me inside. "Sylvia told me all about you after your talk, I'm so glad I finally get to meet you!" Ushered to the kitchen, we sat down with some coffee, feeling instantly comfortable with the bubbly and giggling woman before me. I almost forgot about the final line of that email.

Almost.

Feeling the key burning a hole in my pocket, I continued chatting with Felicia, having her own magic ways of pulling whatever information she wished out of me. I was an open book, whether I wished to be or not, unable to hide anything from those excitable wide eyes.

"I'm so excited for today, Rory! When Sylvia first talked about you, we both knew we just HAD to have you over." Giggling, she cupped my face with her hand, enjoying the effect she was having over me. "I can't wait to turn you into a pretty girl." My eyes widened, wondering if I had heard her correctly.

"Now now, Felicia. Don't spoil the surprise." Professor Amber's commanding voice drifted into the kitchen, strolling in to see my expression. "Good morning, Rory." Smirking, not explaining this 'surprise' any further. Leaving me in the hands of her excitable wife, she poured some coffee, leaning against the counter while she watched. My eyes never left her while Felicia continued her examination of my face.

Pulling up a chair, Professor Amber sat beside me, making no effort to hinder her wife. Crossing her legs, she watched my confused, blushing face.

"After discussing with Felicia, we both decided that you needed help with your studies." Those stern eyes locked onto me, tearing at any resistance I had. "You have done well on your own so far, but we feel a firm hand will be better for you, help you focus. And, as I am sure you can tell, some of us are very excited about your more feminine qualities." Felicia giggled, still holding my face hostage with her hands.

"So. Today, we are going to show you our plan to help you, exactly what it will entail. And at the end, you can decide if you want that help or not, simple as that." I whimpered, already knowing I would, there was simply no way I could refuse these two women anything they desired. I nodded, to the delightful squeal of Felicia, and the sly smile of Professor Amber.

Taking my hand, they both led me upstairs to the bathroom, quickly losing my clothes. My heart beat in my chest as I handed over my key to Professor Amber, watching it disappear into her pocket. They both complimented my panties, almost always wearing them when caged, clit aching inside. The tiny cage keeping me snug and small, but it didn't stop the straining I felt, nor the excitement.

Sitting down in front of the mirror, Felicia and Professor Amber took their time with my make-up and hair, making me promise to bring my wig the next time I was here. In my own silent heaven, I sat there while I watched my transformation, the two excited faces hovering around me, loving every minute. Satisfied I was ready to be their good girl, they both took my hands, led to the guest room for the next piece of the puzzle.

My knees nearly buckled seeing the maids outfit on the bed, a wondrous collection of black and white, with ruffles and lace spread throughout. My final piece of resistance shattered by the dress, I stripped out of my panties, handing them over to the outstretched hand of Professor Amber, staring at my clit with a hunger in her eyes. Felicia on the other hand, giggled.

"Oh look how cute it is!" I blushed hard, moving my hands to cover myself. But that was stopped with a cleared throat from Professor Amber, whimpering as I clasped them behind my back. Feeling vulnerable being so exposed in front of them, over a week of being caged and denied, my poor clit strained from the position I found myself in, desperately trying not to leak.

Smirking, Professor Amber tilted my head towards her with a finger, capturing my attention. "Now that," her voice soft and demanding, "is a very good look for you, Rory." I blushed hard, melting under her stare, her commanding presence. Thankfully, they let me slide new lace panties up my shaved legs, followed by opaque white tights. Excitedly, Felicia playfully spanked my nylon butt, enjoying the blushes she could force to my cheeks.

The uniform fit quite well surprisingly, maybe a bit too snug around my chest. Poufy shoulder sleeves, lace trim all over, and the hem pushed out by petticoats, I felt so pretty wearing it for them, not to mention being fawned over as they fussed with every aspect. Helping me step into some reasonable black heels, both women drank in their final product, a mix of awe and excitement on both their faces.

"Oh it's perfect, Syl! Just perfect. What a cute maid you make Rory!" Felicia exclaimed, playfully lifting the hem of my dress. I couldn't stop smiling, a permanent blush on my face as I twirled for them, giggling, lost in my role for the day. Lost in being Rory.

"Perfect indeed." Professor Amber's eyes widened and danced seeing me, enjoying the shift in her student. "You look adorable, Rory." Giggling, I curtsied, thanking her. They both liked that very much, soon giving tips as I perfected my technique. Watching me in my heels, gingerly moving down the stairs, they both drank in their new toy. Those stares continued to follow me as I went about the list of chores they had planned, kept busy being their good girl.

All day I moved through chores. Cleaning the kitchen, vacuuming the hall, wiping down windows, scrubbing the bathroom, gently folding laundry; all of which with a big smile on my face. Somehow doing mundane tasks seemed far more fun in my maid uniform, wondering if they'd let me take it home to do my own too! I certainly enjoyed being girly while doing chores at home, but there was something about a maids dress that made it...different.

Throughout the day both women enjoyed teasing me in their own way. Felicia constantly played with my dress, having me curtsy or pose for her while she took pictures. Professor Amber scrutinised my work, pointing out things I missed, occasionally testing me on her lessons, simply sitting in the same room while those intense, piercing eyes followed me around. It was almost enough to make a girl cum.

Cooking dinner, my feet and legs exhausted from my heels, the two chatted at the table while I worked. Professor Amber had made me kneel beside them during lunch which Felicia simply adored, so I had an idea where my place would be during dinner. Sure enough, on my little pillow between them, I was ignored while they talked and ate, the occasional hand brushing through my hair. The effects of the day had done a number on my poor clit, knowing my panties were most certainly wet.