I awoke early the next morning to the painful sensation of my cock straining against its cage in yet another futile attempt at morning wood. Aside from the single hard-on I achieved in the mere seconds of freedom you allowed me the day before, the plastic prison encasing my manhood had prevented me from forming any kind of erection since you locked me up 31 days ago. And even that one was a false promise; a denial that left my balls aching and my spirit broken.

A wave of mixed emotions washed over me as I reflected on my predicament. The anger and frustration I felt towards you for making me play your protracted, sadistic game was met by an unexpected sense of calm and security. The absolute control you wielded over me somehow created a safe space for me to rest my mind. I didn’t have to worry about the daily concerns of life like what I would eat or what I would wear. You decided those things for me now. I didn’t have to fret over my future. You already had that planned out for me, and you would distribute the plan with me one step at a time. I now had a singular purpose to order my life around: pleasing and obeying you, my Madam.

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Still groggy from sleep, I reached down to adjust my cage and felt the soft fabric of the backless panties you picked out for me to wear last night. White silk with red polka dots and a little white bow concealed my cage in the front, while a few thin strips of elastic framed my ass in the back, leaving me fully exposed and vulnerable from behind. I smiled knowingly as I imagined what you might have in store for me today; spanking, caning, pegging… Whatever it was, a few things were certain: you would push me to my limits, I would beg for release, and you would reject my pleas.

A month ago, I couldn’t imagine going more than a few days without an orgasm. And now, after serving my time, approaching the precipice of release, and being denied once again, I faced the daunting reality of enduring the 30 additional days of chastity that you so fiendishly added to my sentence. 60 days without an orgasm? Was that even feasible? I had no choice but to figure out.

I was partially to blame, though. When you let me out of my cage the day before, I wasn’t listening to you closely enough. My mind was in a haze. If I had paid better attention to your commands – better comprehended my tasks – I would have had more time; I would have had my release. I resolved in that moment to be more vigilant – to hang on to your every word. I would be ready next time. All that stood between me and that ecstasy were 3 tasks.

You already gave me my first task: Wait 30 days. But of course it wasn’t just waiting that you had in store for me, was it? No, this would be an active sort of waiting; one where the pace of my training was about to accelerate exponentially.

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“Strip,” you demanded.

I had just returned home from dinner with friends from work. You met me at the door with your sudden order, and I knew better than to protest or to keep you waiting. “Delayed obedience is still disobedience,” you would all the time say, and my ass was still sore from the last time I hesitated to follow your instructions.

“Yes, Madam.”

I quickly removed my jeans, polo, and tennis shoes, revealing the backless panties you chose for me earlier in the day. You grabbed the clothes from me and promptly cut them up with scissors and tossed them in the trash.

“Madam, what in the world are you-“

“HUSH,” you interrupted. “Unlock your phone and give it to me.”

I handed you my unlocked phone, and you scrolled and typed away at it for a few minutes, before powering it off and locking it securely away in the safe we kept in our hall closet – a safe I didn’t know the combination to.

“Did you enjoy saying your goodbyes to your work friends tonight?” you asked.

We had decided two weeks ago that I would quit my job and devote myself to your service 24/7. I worked an entry level marketing job with long hours and low pay, and you felt it was distracting me from serving you properly. You earned three times what I brought home anyway, and I had no real expenses living with you now, so I readily agreed to give up my dead-end job. Some friends threw a small going-away party for me, and I was feeling relaxed and happy after a few drinks and a few more laughs.

“I did, Madam. I’ll miss them, but I’m glad to be done with that job. We made plans to get together every 6 months and to keep in contact.”

“Good,” you said. “The next time you see them, they won’t even recognize you, though.”

A puzzled and worried look flashed across my face as you continued.

“Don’t worry, pet. This will be good for you. Follow me.”

You led me into the bedroom, pausing by the closet door.

“Do you remember why I put you in chastity in the first place?” you asked.

“Because I came without permission, Madam.”

“Yes, but why did I delay your orgasms to start with?”

“Because you enjoy watching me squirm?” I said with a smirk.

“I do,” you chuckled, “but that’s not why. I delay your orgasms because your thinking is clouded by your teenager-like horniness and your constant need to cum. That tiny little dick of yours is becoming a huge problem. We’ve got to stop you from thinking with it, and the only way to do that is to subjugate your desire to cum to your higher-level reasoning. In other words, you need to start thinking like a woman.”

With that, you opened the closet door and motioned for me to enter. Inside, I found all of my clothes were missing, and in their place were miniskirts, dresses, high heels, blouses, and all the normal trappings of a woman’s closet.

“What happened to my all of my clothes, Madam?”

“These ARE your clothes, princess. I donated all of your old clothes to charity. These new ones are much nicer and much more appropriate for a good girl like you. They’ll help you get into the right headspace to overcome your insatiable sexual appetites.”

“But- but what will I wear in public?”

“Think, princess. You’re a bright girl.” You paused to let my new reality sink in.

I stood buck naked in the closet aside from my cage and panties, distraught. You had disposed of all of my men’s clothes, and destroyed the final set I wore earlier today. You controlled our finances, so I couldn’t order any new ones online. You locked my phone away in a safe, so I couldn’t call anyone – not that I wanted to admit to anyone the type of kinks I was into anyway. I slowly realized that I only had two options: I could remain naked, or I could wear the clothes you had bought for me.

“Blocking access to your dick clearly wasn’t enough to get you thinking clearly,” you said. “To get you thinking like a woman, you’re going to have to FEEL like a woman, and that starts with looking the part. Besides, I think you look so hot all dolled up for me. I can’t stop watching that video you made fucking yourself in your bimbo costume with my big black dildo,” you said with a wink. “It made me cum three times this evening while you were out.”

You loved rubbing in the fact that you were free to cum as much as you wanted, while I was totally deprived. It reasserted your dominance and my helplessness at the same time. Plus, you simply enjoyed taunting me for the fun of it. You really did like watching me squirm.

“Now I know this will take some getting used to, but I also know what’s best for you, and I expect total obedience,” you said. “You’ll develop your own style over time, but let’s cover some basic ground rules.

“First, no more men’s clothes for you. Ever. And no women’s pants either. Skirts and dresses only. I want easy access to your ass all the time.

“Second, you will keep your face clean-shaven and apply full makeup every morning. Don’t worry – I’ll teach you how. I left some basics that I think will be good for your skin tone in your vanity.

“Third, you are to maintain a completely hairless body below the neck all the time. You shave everything, every day. No exceptions.

“Finally, you’ll need long hair to round out your look. Your natural hair will grow out eventually, but you’ll wear this wig in the meantime.”

You placed a dark brown wig with bangs over my hair and adjusted it, fluffing it and smoothing it out to look more natural.

“Now, go put on the outfit I laid out for you in the bedroom”

I walked into the bedroom to discover a schoolgirl outfit similar to the one I wore in the video I sent you just a day ago: a red plaid miniskirt, white knee-high stockings, black stilettos, a white tie-up crop top, and a pink collar.

“You’ll notice that I’ll be dressing you according to the maturity and sophistication you exhibit in our training sessions and in our daily interactions. Today, you asked me to release you from chastity and to be allowed to cum no less than 5 times, so you’ve shown yourself to be nothing but a brainless nymphomaniac bimbo. And that’s how you’ll dress tonight.

Now hurry up and get ready – we’re going out! I haven’t eaten yet, and I’m craving a nice steak dinner. Let’s go to that place you introduced me to downtown – the one where the staff all know you by name. I think we’ll need to re-introduce you though,” you said with an evil giggle.

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The following month was a crash course on living life as a woman. My feet ached and my calves burned as I learned to walk confidently in stilettos. The daily rituals of primping and preening were time-consuming and exhausting. The quest to remain hairless led me through myriad products that over-promised and under-delivered. The harassment from random men passing by was vulgar and shocking. Life certainly looked different living as the opposite sex, and it gave me a new sort of empathy for what you dealt with all these years.

Learning to apply makeup was perhaps the most difficult task of all, though. Initially, it looked very unnatural on me, and it was painfully obvious that I was a man wearing makeup – not a natural woman. However, after hours of YouTube tutorials on contouring and hundreds of dollars spent on products, I had achieved a consistent and pretty convincing look. Instead of looking like a Domme and her sissy slut sub when we went out in public, we just looked like two girlfriends enjoying time together. I even passed people who knew me on the street multiple times, and no one recognized me. I felt almost like a secret agent, disguising myself to gain access to some top secret information.

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With each passing day, it grew more and more difficult to keep my painful attempts at an erection under control. I woke up multiple times each night to painful semi’s. Pre-cum was constantly oozing out of my confined cock and leaking through my panties. It got so bad at one point that you started making me wear panty liners to catch my juices and keep me clean.

I was learning to hold my tongue and defer my bodily needs without complaining, which obviously didn’t come naturally. I comported myself so well one week that you dressed me in a sharp-looking pencil skirt and silk blouse as a reward, praising me for my sophistication and excellent behavior. That didn’t last long, of course, and I was quickly demoted to “bimbo slut” and then “five-dollar whore” the next two days for leveraging my good behavior into an opportunity to ask you to let me cum. My desperation grew every day, yes, but so did my devotion to you and my desire to make you proud. I was determined that the latter side of me would win out.

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30 painstaking days later, I had completed my first task. It was now 60 days since my last orgasm, and I started my day full of hope and optimism that I would finally be permitted to cum.

“Good morning, Madam!” I said in a far-too-chipper tone for 6 AM.

“Good morning, slut,” you quipped back. “Your first number is 2. I think. Hmmm… I seem to have forgotten it actually. Oh well. Now leave me alone.”

It was 2. You were just kidding around. Surely.

I remained standing silently in the kitchen while you poured your coffee, expectantly waiting for my next task.

“Can I help you with something?”

You were toying with me. You knew what I wanted. What I NEEDED. “Ohhhh yes, your next task,” you teased.

I smiled brightly, listening intently to detect any sly tricks or short timelines like I fell victim to last time.

“It’s time you started contributing some money to this household again,” you said stoically. “I was racking my brain last night thinking of something you could do that would earn us a good income while not interfering with your service to me. And I came up with just the thing! Can you guess what it is?”

Annoyed, I shrugged and waited for you to continue.

“What do all useless bimbos like you turn to when they need some cash these days?” you asked.

I could guess where this was headed, but I just shrugged again.

“That’s right, you’re going to start an OnlyFans,” you announced matter-of-factly. “Your second task is to earn your first $1000 on OnlyFans. Bring me your statement with $1000 in earnings, and you’ll have completed your second task.”

I stood incredulous with my mouth gaping open trying to formulate a response as you walked confidently out of the room. It had been 60 days since my last orgasm. 30 days since my last infinitesimally brief release from my cage. And now, who knows how long it will take to earn $1000 as a new performer on OnlyFans?

“Here, you’ll need this,” you said as you walked back into the kitchen and handed me the phone that you had locked away a month ago. “The good news is that you’ve built up some good content to share – the videos you’ve created for me will be real crowd-pleasers. The bad news is that you’ll still need to drum up some business. Better get busy posting those thirst traps to Instagram and Tinder!”

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I setup my new OnlyFans user account and uploaded a set of my best videos. Videos of you fucking my ass and my throat, videos of you whipping me, videos of me fucking myself with your dildos. I set my price at $5/month and published my page.

I guess I really was a five-dollar whore after all.

Next, I went searching for paying customers. I would need 200 of them to hit my $1000 goal. I downloaded Instagram and created a new user account. I followed a few female celebrities, as well as a number of men who commented with fire emojis on their photos. My target audience made themselves incredibly easy to identify. I added a link to my OnlyFans in my user account and uploaded a cute selfie giving a sexy, sultry look. The caption read, “Want to see more? Link in bio”. That need to do it, right?

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6 hours later, no likes, no subscribers.

I uploaded another photo, this time showing my full body in a cute skirt and blouse combo, bending over and blowing a kiss. “I’ve been a bad girl. Punish me. Link in bio.” I followed and messaged more horny-looking middle-aged men.

6 more hours later, one like, no subscribers. Shit.

Desperate for some traction, I put on my schoolgirl outfit, lifted up the back of my skirt, and posted a pic of my ass in a thong while looking coyly over my shoulder. Frustrated, I locked my phone and called it a night.

The next morning, I woke up and immediately checked IG. 30 likes! I logged into OnlyFans. 2 subscribers! Now we were getting somewhere! After my initial wave of excitement wore off, however, reality set in and I realized that I was still only 1% of the way to my goal. It would take me forever finish my second task at this rate.

Reluctantly, I became the very thing I hated when I was using the dating applications years ago: an OnlyFans slut fishing for subscribers on Tinder. But desperate times called for desperate measures. I downloaded the app and used my most recent IG post as my photo. I added the cringiest Swipebait user account text I could think of: “I won’t bite… unless you ask me too ;)” I swiped for a bit then set my phone down.

10 minutes later, the matches were rolling in. Was it really this easy for girls to get laid? I had experienced many of the hard things women have to endure this month, so it was nice when something actually came easily for once.

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Seven days and three private video sessions later, I had earned my first $1000 on OF. I couldn’t believe it! I could easily make more doing this than I made at my old marketing job. I finally understood the allure of the platform for attractive young girls. I also felt that I had anonymity because of my carefully crafted disguise. I was elated.

Triumphantly, I announced the completion of my second task to you the moment you returned from work later that day.

“Good girl. But that’s no way to greet your Madam when she gets home from a long day. I’m adding 3 more days to your sentence. I’ll give you your number and your final task on Saturday.”