The Descent Ch. 03 - The Show

She jarred me awake, destroying arguably the best slumber I had ever had. "Wh-what?" I managed.

"Darling, you must get up, it's five AM and I have no wish for you to see me like this, yet," she softened her words.

I blinked and rubbed my face with the palm of my hands. Sitting up still wearing incredibly sexy lingerie nearly made my clitty rise, but her words had been pressing, her manner impatient. "As you wish, Madam."

She walked me to the door, and even peeked out. "You have everything?" she asked.

"Yes, Madam."

She looked around in the empty building corridor. "The coast is clear. But," she giggled, "watching you will certainly set my day right!" I turned, once I got to my apartment, and looked back. She saw, and looked to be expecting my turn. We waved, blew kisses, and then returned to the safety of our own place. I knew that getting back to sleep would be a waste of time, and having nothing better or more sane to do, I carefully got out of my feminine night wear and donned running gear.

That morning I ran hard, harder than I usually did. Maybe it was getting up that early. But I ended the run breathing heavily, and sweating through the layers of garments protecting me from the otherwise cold but blessedly dry air. I got into the car before the cooling sweat chilled me to the core, and drove to my apartment. Madam's 7-Series was gone, and I went into my place and took a lengthy, albeit disappointingly regular shower, and then dressed as I normally would for work, save for the sexy underwear.

I looked down at my burgundy-painted toes, and wiggled them. They looked cute, to my eyes, although clearly they looked cuter whilst encased in stockings. But such things were mere whims alone, and before long I was fed, watered and on my way to work.

I had anticipated a day of wasting time, being unable to separate an increasingly intense personal life from my professional one. But there I was surprised; despite a few moments where pleasant thoughts lingered and tingled, most of my day was spent dedicated to the job.

When Shana wandered by to ask how my mani-pedi went, I told her all about it. I held nothing back, including the fast-talk in the foreign language between the various workers. Shana laughed along with me on that, smiling as she let me know they often did the same thing for her. We talked for maybe twenty minutes, fifteen or so of it dedicated to figuring out a way for her to get her boyfriend to join her. No decisions were reached, but she had some good ideas, I thought.

Around quarter to five my phone dinged and I saw it was Madam. Her text was brief and to the point: I need your personal email please. I replied with it, and then opened my email app. Not long after I saw an invitation to a new shared folder at a commonly-used media-sharing site. I clicked the link and joined with an appropriate password.

At the moment there was a single file that had the day's date, with the title TASK.

My sweet sissy boy, this is to be our shared site where we can track our pleasures together. Unfortunately, I am writing this with my laptop perched in my lap, awaiting an evening flight due to circumstances beyond my control. Thus I will not be seeing you until this weekend. I am quite saddened by this.

So I will leave you with tasks to perform for me - for us, darling. My sweet sissy boy should go to a sex toy store, and purchase a set of three anal plugs, smallest to largest. Choosing pink here would be a bonus!

Then, this evening, and each day for the rest of the week, until I call for you on Saturday, you are to wear your plug. You will masturbate for me, once daily only, and never before 9PM, in the style I have instructed, and you will of course eat your sweet sissy cream.

If you truly wish to exhilarate Madam, you will take photos of your session, at the start, and of course at the end with your sweet sissy cream puddled all over your body. Upload them as this site is for the two of us only and forever.

But if you choose not to, you will not face any recriminations.

I am already missing you, my darling sweet sissy boy.

Madam

PS - further extra credit may be earned by describing for me in vivid detail your masturbation moments for me!

Well...fuck. Or maybe not. I pored through that email multiple times. I was amazed how reading "sweet sissy boy" was "heard" in my brain spoken by her, and how that thought sent a signal right to my clitty to wake up.

I knew where there was such a store, and upon leaving work drove immediately there. I had never perused those toys before. There were many to choose from, and the female clerk who did come over to assist - whether I liked it or not - saw what I was looking at and firmly told me that lube was not optional. "Trust me," she told me, her grin suggesting that she had practice with such devices, "you do not want to try it otherwise."

I could not resist asking, even though it was deeply personal and really, none of my business. "You sound like you speak from experience."

She winked. "Maybe I do, maybe I don't. But ask yourself if you really want one of those, like the biggest one, shoved up your butt without lube, or not?"

"Point taken. I'll take the lube."

She grinned. "Anything else?"

"I might as well browse around a little."

"Sure, whenever you're ready, I'll get you set up," she said and left me. I browsed racks of toys for maybe fifteen or twenty minutes. I felt not a little lost; was it really necessary to have seventy different models of vibrators? Maybe; there were like twenty or twenty-five masturbators. But in the end, the only thing I left with was the box containing the three bright-pink butt plugs and a big bottle of lube.

I drove home, and felt oddly lost. The past few days had been so intense, and filled with new experiences and wonders and sexual pleasures the likes of which I'd only imagined. Stuck without anything to do, I made a light supper and ended up going for a walk in a different yet still close-by park. It was cold, and my walk was shortened by the lack of light and cold feet. Besides, it was finally time to perhaps move into my evening's pleasures.

I got into my apartment, and went into my bedroom, stripping down. I looked at my legs, and saw a bit of stubble beginning to peek through. My apartment had a really small bathtub, so I ran it as hot as I could, and managed to get inside it - mostly. But I added a drop of essential oil to waft the most relaxing aroma possible into the bath, and included a few drops of a nice bubble bath. I sat in the tub, easing away the day, and then using a razor touched up my legs and body. I was again relatively satisfied with the results.

At one point, I lifted my red-painted toes out of the water and stared at them. In winter, this was fine, but in the summer? Not so much. Or, did I no longer care? Maybe I did not care. After the bath, I dried off and used a moisturizer before heading into my bedroom. I unboxed the plugs, and checked the clock. I was not permitted to masturbate for another hour or so, but she said nothing about the plugs. I got out the lube, and lubed up my ass and the plug, and inhaled deeply.

Feeling the narrow tip press against my opening was a bit of a revelation. It was not the uncomfortable, strange sensation I had anticipated. It was strange, but not in a bad way, in an erotic way. I felt my muscles relax as the slippery properties of the lube did its work. I winced in some pain as the thickest part of the bulb passed by the tight muscular ring, but then it was seated. It felt...good. It was no surprise to me at all, once the plug was snugly set, that my clitty grew.

But, it was not yet time. What could I do? Hmmm. I did draw the sexy panties up my legs, and carefully slid smooth-skinned legs into the luxurious hosiery. Feeling significantly better, I reclined on the bed, and opened the shared website my Madam had set up, while also browsing one of the largest stores on the internet. My searches took quite a while, as much because there were thousands of options for satin panties, and there was no reason for me to hurry. My clitty remained hard as I browsed, dreaming about wearing such wonderful panties, and my bum clenched around the intruder that now felt warm and pleasant. I finally made some selections, and made my payments.

Only then did I walk to my bed, and get it all set up. My clitty was erect, but tucked inside the panties, and only once I was set up in place, did I take the picture. Or two. Maybe three. Each little clicking noise caused me to have a little twitch.

Only then did I take my clitty out and begin to pleasure myself. As I had done previously, I went slowly and steadily, focusing on that one spot generating intense waves of pleasure. Each time I clenched, my bum constricted around the plug, which then triggered more intense pleasure. I was again moaning and cooing as the intensity grew, and my hips kept lifting up off of the bed.

Once again, I could not help but to wonder what it would feel like to accept a cock in a penis, how mind-blowingly pleasurable it would be to feel that. Or to be turned over, face down, ass up maybe, as he held his cock and pushed forward. How many years had I wondered about that. I had always presumed that it was natural, since I was a man - feeling sex as a woman would certainly let a man know what he was doing wrong. Maybe it wasn't so natural, I thought as I panted a little harder; maybe I no longer cared.

Stroke. Gasp. Stroke. Oh fuck I'm close. My eyes squeezed shut. Oh let it come, let it come soon, I almost begged my body. But the grip my Madam held upon me was firm; I never once wrapped my fingers around my clitty; I could not even think of it as a shaft or cock any longer. Especially now...so close...god...oh please...

The cummies erupted, sending the cream spraying up my belly. My hips jerked and rocked, and I pushed my legs further apart, opening my lower body to its widest, and most vulnerable point. The clitty kept spewing its cream. But like all orgasms, this one came to its usual sudden end. The large dollop of cream at the tip was wiped up, and put onto my tongue. While I got my camera ready, I held the cream in my mouth, almost sucking on it. I snapped a few pictures, and then proceeded to lick it up. It was so good; I was beginning to look forward to it. Was I supposed to do that?

Even though I was tired, and felt the pull of sleep, I logged onto that site and selected some pictures from my phone, and uploaded them. Then I wrote my summation.

Good evening Madam,

As I just licked up all that delicious cream from my cummies, I wanted to send you these pictures, and tell you about my day. I went right to a sex toy store tonight. The clerk helped me pick. It didn't even occur to me that selecting a 3-pack of hot pink butt plugs might say something! I only thought of it later. She was adamant that I get lube, because she asked me whether I felt putting it in dry would feel good, or not. So I got lube.

When I put it in, the first time, I felt a twinge of pain, but then it settled into place. It left me horny! My sissy clitty grew but it wasn't 9 yet so I did not touch. I did some shopping, though, and I hope when my deliveries occur, I can model them for you, and you'll find them pretty. I thought they were.

When it was 9, or a little after actually, I got all set up in bed, and I touched my clitty spot over and over. Oh, how I moaned and opened and closed my legs as I teased my clitty. It felt sooo good and it took about 30 minute before I finally spilled my cummies. The cream was so sweet and delicious. I might even be beginning to look forward to it.

I hope your night was fun, Madam, and that you will get a good night's sleep. I missed you tonight.

Hope to hear from you soon.

I saved the file, and in my nightie, and panties (I took off the stockings because I was afraid of damaging them), pulled the sheets up tight, and fell right to sleep. Perhaps I dreamed of prancing around in front of Madam, showing off my new, sexy panties.

With an early wake-up the next, I performed my usual of changing into running gear and heading out for a fast, hard run. A quick shower, and panties, and off I was to work. Of course I probably checked that site a dozen times. Once I got to the office, I fell into my normal rhythm. I smiled at Shana as we passed each other going down a corridor. She returned it.

I was hugely disappointed when I had nothing from her. I found myself at the same sex toy store that I'd visited the prior day. Why? I don't know. There were a couple of things that intrigued me. I walked in, and the same clerk was working. "Oh, hey," she said as she recognized me. "Did you try them out?"

I looked around, seeing another customer, and thanked her silently for discretion. "Worked out just fine. Your advice was heeded," I said.

"See?" She smiled. "Need more help today?"

"No, I think I know what I want."

"All righty!" she said brightly, and bounced away to the next customer, a grumpy-looking old man with rough stubble over a sunken face. He treated her in a surly manner, and she turned, shooing me a look that I interpreted as 'happens all the time.'

I got the items I wanted. The first was a set of three different-sized cock rings. They were made of thick rubber, so I hoped they would hold up. I had bought one, once, long before and had recalled at some point earlier how the restriction had made my clitty feel stronger and thicker, and it resulted in a bigger orgasm. The other item I bought was a little bullet vibrator. I thought, perhaps, that applying the vibe to my clitty spot would drive me wild. I hoped.

She smiled as she rang me up. The grumpy guy stalked out of the store behind me, empty handed. She waited until he was out of the building, and shook her head sadly as her face expressed disapproval. "That perv, he comes in here three times a week. I hate to think that he's in the back jerking off," she said. The store had private viewing booths. I would never, ever think to go into one of those. Ever.

"Sorry," I said.

"Ah, it's all right," she said. "So you wanna tell me?"

I felt a hint of shame, but controlled it. "Well, it was pleasurable."

"I love them," she told me. "I'm wearing one now, one of my smaller ones, though. Just for some low pleasure, y'know?" she said, grinning.

"Really? You wear it throughout the day?"

"Sure, why not," she said. "I like anal," she said. "Might as well keep...in shape, I guess."

I laughed. "Whatever works, right?"

"Exactly."

"See ya later," I said, gathering my stuff and heading towards the door.

"Bye!" she said brightly. I got into the car and drove to the apartment, and saw the tag on my mailbox. I walked up the street to the main office; my complex's policy was to hold all deliveries at the main office so that purchases did not "walk off" during the day. I exchanged my tag and got the two lightweight packages. My heart raced as I returned to my apartment. With this arrival, and the other items, I keenly realized how far off 9PM felt all of a sudden.

After setting things away, taking all the discipline I had not to open everything right there, I made a light supper and did a few other things. Nothing major. Only after all the dishes were cleaned up and the place tidied did I check my laptop. I got another thrill as I saw she had uploaded her own pictures, and there was a new dated task entry.

I opened her text file first.

My sweet sissy boy!

You thrilled me. Totally thrilled me. So much so I was very nearly late for this morning's meeting, because I was so busy pleasuring myself to your pictures and your words. I hope my admission gives your clitty a zing, darling!

Tonight, my darling sissy, when you read this, note the time. Insert your plug. From that moment on, the only thing on or in your body will be that plug. That's right darling, you are to be nude, fully nude, for me for the rest of the night. You are to sleep in the nude.

When you masturbate tonight, you are to do it on your hands and knees the entire time. Your face, down into the bed, your cute bum up in the air, that plug wigging as you moan. Imagine that I'm behind you, watching you. Maybe - probably - I would be unable to control myself, and would have to spank that cute bum of yours!

Go now and strip, and put in your plug, my sweet sissy.

Then I opened her pictures. They were of her, and she was nude, and the last was a close up of her wet fingers stroking her own sex. Her lips were plump and glistening. I groaned aloud, and then stood and quickly stripped naked.

First things first, I got the small plug, and lubed it up. The insertion went easy, and it crossed my mind that maybe at 9PM I should give the medium version a try. I then opened the two packages I had purchased at the store easier. I felt the thick rubber of the rings. The largest, I stretched, and slipped around the base of my clitty and balls before releasing it into place. I instantly felt a surge of hardness, as the restriction ensured that I remained fully erect. I added the second at the base of my balls, just to test, and likewise that snug fit made my sack tighten. On top of that, it seemed to increase the hardness of my clitty.

I stood there, and wondered what I looked like. I got my phone, and went into the bathroom and looked at myself. A thin young man, flat-chested and naturally hairless, with a flat abdomen and no hair in his pubic region, with a stiff clitty. I almost moaned at the sight of me. No wonder she saw me as a sissy. I had the body for it. I snapped a picture and returned to open my new arrivals.

Fingers grazed over materials. The act of simply touching the panties gave me a thrill, and I was so looking forward to wearing them. But I was not going to be doing so, not for some time, and the waiting made it all the more enticing. They were right there! But given the constraints, cheating would make me feel lousy, and so I dared not.

I had never clock-watched so avidly. And as soon as that clock read 9PM, I slipped the plug out. I lubed up the medium-sized one, and gave it a look. I then on my hands and knees, as Madam had decreed, reached behind me and eased the plug into place. It hurt! Oh, it hurt more, even stretched as I was, but I pushed it in and then had to wait out the discomfort until my body adjusted. But then the sensation of fullness was far greater. The plug filled me, and it left me a little breathless.

Suitably prepared, I reached behind me to try and stroke my clitty. But it proved very difficult, and the rings deadened the touch a little. In a moment of inspiration, I pushed my clitty and sack backwards, and then closed my legs to push things back. I then got the little vibe I purchased, and I reached back, switched it on, and applied it to the spot.

"Oh...oh my...gggaaawwwdddd..." I groaned aloud in my own bedroom. The buzzing sent its high-pitched motions throughout my clitty and sack, and seemed to fill it. I gasped as the pleasure from the toy was more intense and powerful than a stroking finger. My lower body kept clenching, as much from the anal intruder as from the vibrations. What it all did was to enliven my need and pushed it higher and higher yet.

It took forever to climax. Well, it felt that way. It probably didn't but then I lost track of time, awash in the buzzing. I was moaning and groaning, and finally when my clitty began spurting, sending rope after rope of my sweet cream over my legs I shuddered and fell forward. For the first time, I really didn't lick it up...because as soon as I switched the vibe off I went almost instantly to sleep.

The next morning, quite early, I awoke to a number of strange sensations. The plug was no longer pleasurable at all, at upon first movement all that dried cream announced itself. Oof. I went into the shower and cleaned up, and dealt with some pangs of guilt that I had not told Madam all about my evening. So after the shower, I sat to relay the night's events to her, including the shopping trip. Having satisfied my guilt, I went for a run, returned home and went to work.