The Descent Ch. 02 - A Slow Glide

I sat up, the dried remnants of last night's orgasm sticking uncomfortably to my body. I looked down at my...clitty, I reminded myself. My clitty. To something akin to horror I felt the familiar lurch in the organ, and the equally familiar sensation of tightening in my balls. My clitty rose, slowly at first, but soon to its fullest extent. It began to pulse, throbbing almost, as I sat there gazing at it with dawning realization. I had to drag my eyes away from my own organ, and looked down at my legs, at how hairless they were. In the daylight, it looked sexy as hell.

But orders were orders, and determination was one of my better strengths. So I ignored the throb in my organ, and took my shower. I hesitated before dressing, recalling how my bottom had felt warmly caressed by the luxurious fabric. I dallied, but in the end chose the standard underwear for myself. Tucked into my boring cotton boxer briefs brought with it a sense of disappointment.

Luckily all hell broke loose at work within minutes after my arrival, which denied me any time to dwell on my situation. I was in a big bank's cyber-security arm, a very junior tech, but I had some important duties. Overnight there had been several attempted hacks, and at least one branch was downed by a crypto-locker. We scurried about all day trying to determine the depth and width of the breach. By four-thirty our team heaved a collective deep breath, realizing that the extent of the damage was to a couple of older computers driven by semi-incompetent assistant managers. No real harm done, although the two assistant managers were read the riot act.

On my drive home was the first time that my thoughts returned to the night prior. My god, I had gone on a Valentine's Day date with an older woman who had so easily pried herself into my deepest sexual secrets. It defied belief, and yet the growing warmth I felt on my cheeks and in my privates reminded me that this fantasy-turned-reality was far more exciting and enticing than the reality itself. I pulled into the drive way, scanning for the big 7-series BMW that I knew my Madam drove. It was not there.

I decided to get in a run. I had run track and field all through high school and college, and had placed third my senior year at my division's national championships in the 10,000 meters. I loved the way my heart raced and body responded while running, and the cold, sloppy conditions did not bother me one bit. I had a headlamp to shine the way on my usual run, and did it in my usual thirty-five minutes. As the endorphins flooded my body, my night with my new Madam was pushed aside. The exercise euphoria lasted until I pulled into the parking lot and spied the 7-series. To my surprise, I put my hand lightly on my chest - a pure reaction - at the excitement of what this night might bring.

I walked up the steps, and Madam's door swung open. "Please, darling, please come in," she said softly. Her head peeked out from behind the door.

"Thank you, Madam," I said in a soft, courteous tone as I breezed past her. She closed the door, and turned to face me. I understood why only her face had been visible to me. Her stockings ended up on creamy thighs, with a black lacy pattern on the ring holding it tightly in place. The small underwear clung tightly to her body, and her black bra cradled and supported lovely breasts. All of this was visible through a gauzy ankle-length housecoat that was tied loosely at her lower abdomen.

"Please, come in." She paused, and sniffed. "Darling, why are you sweaty?"

"I went for a run, Madam," I explained. "It's how I remain in shape, and I love the exercise. I crave it, actually."

"Well, it simply will not do, darling, not at all. You run along now, and draw yourself a steaming hot bath. I'll be in shortly."

"Yes, Madam," I said obediently, and headed off to her bathroom. I stood naked, bent over her big tub, drawing the hot bath. I had removed my male clothing, and folded the wet, sweaty garments before setting them in a corner. Between my legs my clitty once more stood at rigid attention. As I sank into the water, I found myself breathing slowly out, almost a soft sigh of pleasure.

She walked in, carrying two big candles. One, she set on the toilet cover, and the second on the sink countertop. Both were lit, and then she flicked the lights off. The candlelight danced in the room. "And how is my sweet sissy boy today?" she asked smoothly. She had a champagne flute, filled nearly three-quarters full with a golden, bubbly liquid. She sipped from one, and handed me the other. I sipped it - delicious.

"Glad to be home, Madam," I said, then snapped my jaw shut.

"Home?" She smiled. "Darling, that thrills me so that you would think of this as your home. Do not fret," she patted my arm.

"Yes, Madam," I said with relief noticeable even to my own ears. "It was a rough day at work," I said. "I survived," I said after a very brief synopsis. "How was yours?" I asked then.

"Mine? Very routine, darling, very routine," she said. "Not quite boring, but certainly not exciting." She sipped her drink. "And tell me, my sweet sissy boy, about your night last night after you returned to your apartment. Did you spill your sweet sissy cream?"

"I did, Madam," I said, thankful that some of the bubbles from the bath I'd drawn covered my lower body. She would have seen my clitty throb hard at hearing her speak that way.

"Tell me, darling, and as usual, I expect details."

"Yes, Madam." I gathered my thoughts. "It was not hard to edge, Madam. My clitty, it was ready to explode from the first second I touched it. It only took a few strokes, and then I was there, right there on the edge. I wanted to cum, and forced my hand away, forced myself to relax. I focused on my breathing, slow and steady, until that hard need receded some. But then the second I touched myself again, that need returned. The second edge was a close thing, to be honest, Madam," I admitted, and saw her nod, storing it away, and indicating that I should continue. "Then the third, oh my, I was leaking such precum."

"Precummies," she corrected.

I nodded. "Precummies. Yes. I leaked, and leaked."

"Did you taste?"

I felt a flush hit my cheeks. "Yes, Madam."

"Good sissy," she said with another light pat to my arm.

"Then I was ready, allowed, to cum. I looked down at my clitty, watching. I don't know how many strokes it took. Ten, fifteen? Thirty? Not many, and not long. The climax was amazing. My...sissy cream exploded, shooting in long, thick ropes up my chest. Covering my body and abdomen. I know I cried out or moaned, or maybe both. I watched as my balls emptied my cream, all over me, and it was hot and sticky and slippery. I dipped a finger into it," and as I related that part, saw her eyes flash with excitement. "I tasted it. It felt sexy. Good. So I scooped up most of the biggest drops, and licked it all up," I reported. "What was left, stayed on me, because after that orgasm, I passed out. When I woke up this morning, still in the panties and stockings, at first I thought it had been a wonderful dream. When I realized what I was still wearing...well, my clitty got hard right away."

"Did you touch your clitty this morning, my sweet sissy boy?"

"No, Madam," I said with firm head-shakes for emphasis. "I remembered your orders."

"Orders. An unpleasant word. Try to search for another," she suggested.

I ran through the dictionary and thesaurus of my mind. "Your directions, then," I tried.

"Better, darling." She set her glass down. "And your clitty, now? Is it hard?"

A blush, again. "Yes, Madam."

She smiled, something I took as a positive sign. "Are you quite finished with your bath, darling?"

"Yes, Madam, I am clean and refreshed."

"Wonderful." She stood, and closed the bathroom door and pointed at a large, thick, terry cloth robe. "Once you are dried off, slip into that, and then come out to see me."

"Right away, Madam," I assured her. I was true to my word, wondering what pleasures this second evening together might hold. I wrapped myself in the robe, and it felt warm and snuggly against my freshly-bathed skin. I returned to her.

She saw me coming, as I glanced around to once more see that she had lit the room only by candles. Her glasses shone little dancing reflective points of light. I came close, and stood there.

"What underwear did you wear to work today?"

"My usual underwear," I replied honestly. "I gave thought to wearing the panties, Madam, I really did, but..."

"I see," she said and I felt a deeper pang of disappointment in myself for letting her down. "Why did you opt for your boy undies?"

"I..." My hesitation was obvious. Why did I? "I wasn't sure what to do this morning."

"Ah, I see. A moment of indecision. Such moments are to be expected. I do hope that you will not let me down further? Tomorrow?"

I gulped, as my mind tried to come to grips with wearing satin panties all day while at work. "I will not disappoint you, Madam," I affirmed.

"Well, it's not really an act that is worthy of punishment, but I do wonder my sweet sissy boy, if you will indulge me this evening?"

I nodded. "Of course, Madam."

"Disrobe, my sweet sissy," she said. As she spoke, she shifted forward on her couch, and opened the gauzy housecoat, to expose her legs. She crossed her right leg over her left, and then looked up at me. "Now then, my indulgence is that this evening I wish to spank you. Not to punish, but because I feel I must."

"Of-of course, Madam," I lurched a little.

She pointed, and I bent over. She adjusted me, until my soft abdomen was directly over her upper leg. Her hand fell to my bottom, and began sliding around slowly. Each movement sent tingles - of excitement and foreboding - through me. All of which sped directly to my clitty, which remained fully erect and growing demanding for touch.

"I do so love to spank," she said, her hand roaming in slow, large circles, passing back and forth from cheek to cheek. "I find nothing brings me closer to my sweet sissy boys that a slow, intimate spanking over my knee," she continued. Her hand lifted away, and she brought it down with a solid slap. There was a brief hit of a sharp sting, which quickly dulled and not long after, died off completely. "My sissy boys love to be over my knees. Some have been known to misbehave, simply because they want it so badly." The second slap came, this one a trifle louder, and on the same spot. I felt the pain bloom grow a little more intense, spread a little wider, and last a little longer. And it resulted in more throbbing.

"You see, it brings us together," she said. *slap* "You are held by me, entangled over me, quite unable to escape." *slap* "It's it lovely to be so entangled?" she asked, moments before delivering another *slap*.

I winced, as I stared at the carpet, wondering why the spanking felt so deliciously naughty. Painful, yes, but naughty, and it aroused me more. *slap* As her hands resumed roaming, my skin pricked uncomfortably. *slap* That one, delivered with precision to the same spot, brought more than a wince - this one came with a slight whooshing exhale. *slap*

"I can see you squirming, my sweet sissy boy. Are they hurting you now?"

"Yes, Madam," I said, and as I replied she hit the same spot once more. My "Madam" became something more like "Madammmmmmmm" from the strike.

"Squirming, yet you have no thought of escape, do you, my sweet sissy?" *slap*

"No Madam!" I yelped this a little.

"Of course you do not." *slap* "I find that carefully delivered spankings carry a great deal of pleasure, for us both." *slap* "As I can feel your hard little clitty bouncing against my leg, would it interest you to learn that between my legs I am feeling quite hot, and decidedly moist?"

My groan of pleasure morphed into a mewl of discomfort as another *slap* was rendered. "Yes, Madam!"

"Oh so feel such wetness, such arousal, for us both," she whispered, just before *slap*. "Your hard clitty..."

"Yes, Madam, my clitty is hard!" I moaned this. *slap* "Owwww," I finally blurted.

"Shhhh, my sweet sissy. It's quite all right to have your cute little bum spanked," she added. *slap* "You do have a most adorable bum, I must say," she continued.

"Thank-" *slap* "...YOU...Madam," I managed. My breathing was coming a little faster.

"You're quite welcome, darling." *slap* "And your bum, so wonderfully red right now!" she whispered. *slap*

"Th-thank you, Madam," I gasped. Each slap brought with it an intensified blast of sharp pain, and each time the return to that more distant, tolerable ache felt delayed.

*slap* "You are most welcome." She rubbed my bum slowly several times. "And now, for the end."

*slap* *slap* *slap* *slap* "Oowwwweee!" *slap* *slap* "Please Madam!?" *slap* *slap* *slap* "Mmmm ohh it hurts-" * slap* *slap*

"Shhh, sissy, shhhh," she comforted me. Her hand glided smoothly over my bottom once more. "It's all right my sweet sissy."

"Th-thank you Madam," I managed to stammer in a near-normal tone.

"Let's stand you up now, my lovely sissy," she said, and eased me out of my position, until I was once more standing in front of her. She looked at my hard clitty, and smiled as she tilted her head back at me. "You have quite the stiff clitty," she praised me.

"Thank you, Madam."

"Turn around. You see that coffee table?" I turned, and saw it, and told her I did. "Take a seat on it. I wish to inspect your feet." I sat, wincing as my weight settled upon that spot that was still flaming red and itchy/tingly. I did my best to remain still, and offered her a foot. "Tsk tsk. There's no use," she said softly and heavily. "I have a new task for you, darling."

"Yes, Madam?"

"You will get a mani-pedi. Many men do it. And I must say this, too." She paused, her eyes boring into mine, making her point very clear indeed. "You will not be invited to return until you have had your mani-pedi."

"Yes, Madam." Naturally, I resolved to do it tomorrow.

"Excellent." She stood, and invited me to stand. She tapped my bum, indicating that I was to follow her to the bedroom. Once in the bedroom, she once more laid atop her covers, propping her back up against her headrest with multiple pillows. She guided me to her sex, and bade me to worship.

I was once more thrilled to be able to provide this luxurious, erotic service to her. She achieved her orgasm, a quiet, fast one, and then had me lie on the bed, next to her.

"Tonight's task," she said, "will be conducted at your own apartment again."

"Yes, Madam?"

"Tonight you learn to masturbate like a sissy," she proclaimed. "How do you usually do it, with a full-handed grip?"

It was disconcerting to have to answer such personal questions, yet thrillingly erotic to do it. "Yes, usually Madam," I said.

"Usually? Please elaborate, dear."

"Sometimes I just go lightly, or with only a couple of fingers."

"Ah, I understand. Well, what do you think about when a woman masturbates?"

"That it is sexy. Her hands, in her panties, slowly stroking her organ, her clitoris," I replied.

"Yes! That is exactly right. A slow, gentle touch. Do you know that clitties have a little button on them, similar in fact to a woman's clitoris?"

"Yes, the spot right behind the head," I said, and pointed to my clitty.

"Touch it for me," she suggested, and watched as I pressed my index finger to that spot just below the head. "Correct," she said softly.

"So your task, this evening, will be to masturbate like a good sissy. You will use only the tip of your index finger. You will stroke your clitty, playing gently with your clitty-spot. I encourage you to wear your stockings when you do this. Your legs should be spread, and perhaps bent at the knee." She drew her body into the proscribed position, reaching down between her own legs to show me. I nodded, seeing her eyes upon me. "You will savor your time. It is your body. Get to know it, in its most intimate ways. This is not a race to simply spill your sissy cream. This is a time for indulgence. You are indulging in your own sexuality. Succumb to the pleasure of touching your clitty, and you will be rewarded with a powerful, satisfying orgasm."

"I understand, Madam," I said as my voice shook a little.

"You will, of course, continue the practice of cleaning up your sissy cream with your mouth and tongue," she added.

"Yes, Madam."

"Then you may go tonight, my sweet sissy. For I am exhausted, and it is neither fair to you nor I for either of us not to be fully engaged."

"I understand, Madam. Thank you."

She smiled sweetly. "You're welcome, darling. Please, lock the door when you leave. Oh, and one more thing?"

"Yes, Madam?"

"Take your sweaty clothing, but do not wear it to return to your apartment. Go nude."

"Y-yes, Madam," I said. As I had done the night before, I peeked out and saw on one. The keys were ready in my hand, and I ensured her door would lock after closing. I closed it, and scurried to my unit, and let myself in. I closed the door behind me, and hurried to my bedroom.

It was a very different sensation, I quickly realized. My legs, encased the silky hosiery, felt so sexy and slippery. I loved moving them around, even my feet on the bed. I laid back, with my legs spread wide, my balls dangling under my clitty, and felt a sense of vulnerability. Yet the slow, teasing touch - my god. I was moaning and making little noises of pleasure from nearly the start of just using my fingertip to complete my masturbatory task. I was there for quite a while, the build slow and steady, and towards the end, mind-numbing in its need.

Finally, I squirted my sissy cream. My hips rose from the bed and I gulped air, yelping in pleasure, as my clitty spurted its cream. Cascades of cream covered my belly, and I was more eager this time to get the dollops onto my fingers, and drop them into my mouth. At one point I found myself greedily slurping on creamy fingers. And like the night before, having achieved such a powerful orgasm, slipped easily into the needed slumber.

The next day I went to work with the panties. They were tight, and each step I took rubbed my bum in a deliciously subtle, sexy manner. I felt slightly engorged all day long, although never as much as when I quietly asked my co-worker Shana where a good place was for a man to get a mani-pedi.

"Oh?" she had asked, surprised, and curious, but pleased anyway. She asked where I lived, and after we looked at a few places, pointed a good one out. "They're great, just make sure that you have tip money," she advised.

"I do, and I will. Thanks."

"Let me know what you think," she said. "I want my boyfriend to get one with me. Maybe you telling me about it will make it easier for me to convince him!" she suggested. I brightly confirmed I would tell her all about it, and called and made an appointment.

I realized that it was a luxury, to have someone teasing and primping your nails. The lady was duly horrified with my feet, and spoke in rapid-fire native tongues to her coworkers. None at least looked at me, and then giggled in that mean-girl way. Once done, my feet felt scrubbed and simply wonderful, and my nails were cleaned and polished. I was admonished time and again not to bite my nails - a failing I'd tried a lifetime to stop. Afterwards, I felt like it had been the best seventy-five bucks I'd spent in a long time, and I was hopeful that Madam would be equally enthralled.

After I texted her to let her know that my feet were done, she sent a few big smiley face emoticons as a text reply. Then, simply: "8pm."

At 8PM I knocked on her door. It was open, and I heard her invite me in from inside. I walked in closing the door carefully behind me, and joined her, in her typically-candle lit living room.