Literotic asexstories – 30 Days of Denial Pt. 02 by switch8888,switch8888
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 share 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 possible? I had no choice but to find 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 kind 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 always 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 typical 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 apart 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 at all times.
“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 at all times. 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 find 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 kind 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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