The Descent Ch. 02 - A Slow Glide

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She had me strip and show off the nails for me. After a passing judgment of the job done, she had me kneel on the floor while she stood and left the room. She came back with three bottles of nail polish. She set them down and showed them to me, flicking the lights on briefly to show me the colors. "Now, darling, choose your color." My options were a hot, bright pink, a sultry deep red, and a brighter, fire-engine red. I opted for the deeper red.

"Tell me why," she said.

"It looks seductive to me. Bright pink - that doesn't seem to be...the style you are creating, Madam," I said, getting a single nod in reply. "And the bright red, maybe for a special occasion."

"I like how you are thinking, my sweet sissy boy," she praised me. "This adds a touch of elegance, of class, and certainly does not scream trashy, as a hot pink might." She put the other two aside. "Both may have their places, in time, but not now." She smiled, and uncapped the bottle. "And will you allow me to do the honors?" she asked.

I blinked. "Of course, Madam," I said. She painted my toenails slowly, and as I looked at them I felt awash in pleasure. I felt...satisfied. This act, this little kindness, her to me, left me feeling wonderfully thankful to have met her. I said as much as well, which brought a big, genuine smile to her face.

"I am most thankful to have met you as well, darling," she said with a soft coo. "Might I suggest, however, that you let me concentrate lest you want polish all over your big toe?"

"Yes, Madam," I said and remained silent. Once done she put those little toe spreader things in and then had me sit next to her. Of course my clitty was aroused, but not fully stiff.

"Now then, darling, please tell me about your mastubation last night. Was it rewarding?"

"Oh! Oh yes, it was, Madam," I said quickly.

"Do go on." She smiled.

"I slipped on the stockings, and it felt so good, so soft and slippery in bed. When my legs were up and spread, I felt...vulnerable," I related. She patted my leg. "And I felt such erotic pleasures. To touch and touch and touch, and have it just on that one concentrated spot." I actually shuddered, recalling it. "I suppose it was a little like making love to one's self," I said as an aside. "But it took a long time, to climax, and when I did, well, there was quite a lot of sissy cream."

"And?" she asked, smiling, eyes twinkling.

"I enjoyed it all," I assured her, matching the smile.

"Oh my love!" she said and reached out, and pulled me into a hug. "You're doing such a good job, I'm thrilled with your progress!" she assured me. "And to work?"

"I wore the panties, Madam."

"How did that feel?"

"All day, like my bum was being caressed by something soft, feminine, sexy. My clitty felt a little stirred all day long," I assured her.

"That's wonderful, my sweet sissy boy. So feminine and soft. And now, a moment to indulge in what we both want," she said. She gathered me close, and slowly began to shrug out of her clothes. I helped her with that, until she was fully nude. She then asked me to kneel, with my eyes closed. I heard her leave, and it was five minutes or maybe longer before she returned. She sat down in front of me, and suggested that I could open my eyes.

Her lingerie set was once again glorious. Her stockings, again black, looked sleeker than her others, shiny almost. I wanted to touch her legs, and looked at her face, my eyes showing my desire. "Can...can I feel your legs, Madam?" I whispered.

She paused, and whatever thoughts she had in mind, she set aside. "Yes, darling, you may." She watched, as my fingers reached out, and stroked the material so softly, my fingers trembling. After a sharp inhale, there was a catch as I breathed out, such was my arousal and pleasure at touching her. "Your opinion?" she asked.

"Magnificent, Madam," came my reply in a wondrous whispery tone.

"I have a second pair, darling. Would you be enticed?"

I could not believe how wide my grin felt, like my jaw was going to crack. "Oh yes please, Madam, yes please!"

"You are such a feminine sissy," she said, adopting a little of that lecture tone, while she withdrew the stockings for me. "But I do so love it," she added to make sure I understood. She watched as I slowly drew the stockings up my bare legs. "Tell me about it, my sweet sissy boy."

"Oh Madam, the material is so soft and clingy, it makes my legs instantly feel so warm and sexy."

"It makes your clitty throb, putting those stockings on?" she prompted.

"Oh yes, Madam. Throbbing, and leaking," I added.

"Good sissy boy," she said softly. The second was added in silence, and then I stood before her, a hard clitty pointing out towards her, my legs encased in the best stockings I'd ever felt.

She reached into the bag she brought with her. "And now these," she said. They were a pair of satin panties, a deep, deep red. Darker than blood, and they were amazing on my body as I slid them on. I tucked my clitty into the panties, leaving a clear outline of the organ through the front of the garment, and Madam lightly put a fingertip over the wet spot that appeared almost instantly.

"You are leaking, my sweet sissy," she chuckled.

"Yes, Madam," I said, rather uselessly.

"And now, for the finishing touch." She withdrew a satin nightie. It had spaghetti straps, and lace outlining the bra. She slipped it over my body, which elicited a ragged exhale from me, as I was ensconced in the sheer and slippery garment.

"Oh my," she said wonderingly, looking at me. "We have a ways to go with you, yet," she commented as her head tilted from side to side during this inspection, which ended with a satisfied smile, "but you will do nicely for now. As you may have already guessed, you will be sleeping in this tonight."

I could not stop my grin. "I had hoped you might say that, Madam," was my soft reply.

She adjusted herself on the couch, sitting primly in the center, crossing one leg atop the other. After a few more clothing adjustments, untucking caught things, she patted her lap. "Kneel over me, right here," she said. She watched as I put one knee on the couch before throwing my body over her. I slid forward, a little, until I was comfortably atop her lap, my knees pressing down into the soft cushions of the couch.

"Now then," she said softly, in that dim candle-lit room, "have you ever gone to a strip club and watched the girls dance?"

"Once or twice, Madam," I admitted.

"Did you ever purchase a lap dance?"

"No, Madam."

"You are going to dance for me, now. To give me a lap dance. Because it pleases me, and because it is an erotic show, just between us." She put her hand lightly on my chest, seeing my reaction of my eyes opening wide and enough of a shudder to let her know that this thought frightened me. "Easy, sweet sissy boy. All you need to do to start is rock you hips forward, not quite a thrust with your clitty into a woman's sex, but the concept is fundamentally similar. So let's see you move your hips."

Her eyes dropped and she put her fingers on my hips, on either side. I inhaled to steady a sudden burst of nerves, and then rocked forward.

"No, darling," she said right away. "That was with your legs. Just your hips."

"Like...like this?" I asked, and sort of thrust them forward and up.

"Better. Now back," she advised.

Her fingers guided me. Pressure here, or there, until I was in a bit of a slow, smooth motion, rocking over her body.

"Put your hands to your neck, as if you had a whole head of thick, glorious hair, and you were toulsing it for me, teasing me with your sexiness," she said.

I did, feeling my chest become exposed. I realized that as I moved, slowly, but steadily, and now played with my hair, that my arousal back back to the forefront of my mind, and that it was strong, perhaps as strong as it had ever been while in her company.

I felt my clitty surge again, as I rocked, and when Madam's fingers caressed my thighs, a soft moan escaped me.

"Aroused, my sweet sissy boy?"

"Yes, Madam," I returned, my voice remaining whispery.

"You look stunning, and your movements are improving," she said. "Imagine that your boipussy is rising and falling over a cock. That it slips so deliciously inside of you, filling you. Rock that way," she changed.

I closed my eyes for a minute, envisioning it. It was not all that hard to envision, to be honest, and with my legs spread so widely, it felt deeply erotic to me to imagine taking something in my anus. I'd never done that, not even touched myself there, but ensnared by her wiles, the thought was not repulsive but erotic.

"I can feel how your hips changed, are you envisioning it, my dear sweet sissy?"

I exhaled slowly. "Yes, Madam, rather easily."

"It excites you?"

"Strangely enough, yes."

She patted my thighs, and began to run her hands up and down my legs in rhythm with my movements. Each time she got closer and closer to my shaved crotch. My clitty jumped with excitement each time her fingers grew near.

"Oh...oh Madam," I gasped at one point, feeling my lower body clench so hard. I was envisioning that I was all the way down on that cock, and with her fingers dancing so closely to my clitty, I felt I might explode in passion.

"Are you fully aroused, my sweet sissy boy?"

"Yesssss Madam." I moaned it. My upper-body activities, my hands running through my hair, grew busier as I fell deeper into this passionate moment.

"Lean forward, run your hands through my hair. Give me a show, my sweet sissy," she suggested very softly.

I leaned forward, the angle changing on my hips, and ran my fingers slowly through her hair, teasing it and stroking her shoulders. I was able to look into her eyes, and saw the shine of her own arousal there. I was beyond turned on; to say I was a prisoner of this passion was not an understatement. These soft little moans, and gasps of pleasure, kept coming from my mouth.

"Oh yes my sweet sissy," she replied. Her head tilted back as I ran my fingers along her scalp, her mouth opened as she inhaled faster yet shallower. "Yes, darling, show me how much you adore me."

"Oh I do Madam I do!" I moaned it. Hips rocked faster now. Never in my life had I wished to be fucking a cock and not a woman, but right now that's what I was wishing. Not to bury my clitty within Madam's sex, but to bury myself on a turgid cock.

"You are such a wonderful sissy," she moaned it. "Giving in to your feminine passions. You want to be taken right now, don't you? Imagine being so aroused that all you can do is look behind you, and beg!"

"I would, Madam," came my soft, almost high-pitched moan. "Oh I so would right now!"

"And if I touched your clitty right now, it might explode?"

"Oh yes!" I moaned. "I could not hold it back, not for long," came a reply punctuated with pauses and desperate inhalations.

"That's my good sissy." Her fingers stroked my clitty, over the panties.

"Aaaahhhh," I moaned it. "Oh it feels so good!"

"Mmmm usually I would demand to orgasm first..." she mused.

"Oh I would love to worship you, Madam," I said quickly. "It would be an honor for me!"

"I know darling," she patted my legs, and stroked my clitty again, making me shudder and groan aloud. "Yes, I do wish for you to worship me." She patted my leg. "And I have a reward in mind for you, for that most erotic and pleasing lap dance."

I followed her into bed, and watched her climb onto the bed, propping up her back, and pulling her legs up with bent knees, and opening widely for me. I gazed at her bare sex, and saw her lips swollen and glistening with need. "Make love to me, as a sweet sissy should," she offered softly. "I know you will perform admirably!"

This was not a slow, tender worship of her sex. While I savored every tasty drop and let the musky scent intoxicate me further, I simply could not take it slow and easy. I was fast, hard, almost frenzied in my worship, and my reward were her screeches, cries, and her hand on my head that all culminated in a very fast and hugely powerful orgasm.

I knew, because her breath came out all at once, in a huge whomp, and she went stiff. One hand grasped desperately on my scalp, the other pulling wildly on bed covers. Her back arched and then when she finally found her voice, her only option was a long, loud "OoooOOoooOoOOOooooOOOoooooooooooo..." that trailed off. Her chest heaved, breasts rising and falling fast, as she continued panting. "Stop - you must stop," she said weakly, pushing me away and curling up in a fetal position.

After resting, her vision found its focus upon me. She patted the bed next to her, "Kneel here as a good sissy boy should," she said. She adjusted my stance until my knees were widely separated. When her fingers nimbly extracted my fleshy, rock-hard clitty from the panties I shuddered and moaned passionately.

"Oh that feels so good, yes, my sweet sissy?"

"Amazing, Madam, yes!" I agreed.

She waited until my focus was upon her. "Just wait a second," she said. Her hand moved slowly over her abdomen, and then between her legs. I saw her dip two, then three fingers into her sex, and when she withdrew them I saw the fine strand of fluid running from fingers to sex. She then used that hand to stroke my cock, and the hot, slippery fluid created such pleasure I cried out very loudly.

"That's it, my sweet sissy boy. You can shoot your cummies now, you make your sissy cream for Madam!" she urged me.

I did not need support. My back arched, and my hands went to the back of my neck as I strained my hips forward...her fingers sliding so easily along my clitty...I was lost...gasping...oh god...it's coming...so fast...oh oh oh...d-d-d..."MADDDAAAMMMMM!" I screamed as my body gave into the physical sexual sensation.

My clitty simply exploded, sending long, thick ropes of cream in a high arc, landing all the way across her body to her body, with the lesser blasts landing and splattering all over her belly. I could not believe it, how many hard pulses of sweet sissy cream erupted from my clitty. Finally, when it was all done and my balls were emptied, and the only thing happening was that slow, final dribble of cream coming out, she wiped it up with her fingers.

There was a lot. It was a mixture of whitish and clear fluids. She held it up.

"May I, Madam?" I asked her.

"Please." I gently clasped her wrist, thumb and forefinger, and brought the cream-covered digits into my mouth. This was no dabble; this was the real thing. The taste was stronger and at once both a little off-putting and arousing. I was not surprised when I was then made to lick the remnants of my explosion from her body.

She had me lie with her, and we snuggled, our bodies facing one another, looking into each other's eyes. "I am too happy to send you to your apartment tonight," she said. "You'll stay here with me," she decided.

"I am honored, Madam," I assured her in a sleepy tone. The pull of sleep was quite strong, and evidently hers was as well. Between rich, satin sheets we slipped, and each of us fell to slumber quickly, still lying on our sides, still looking at each other.

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5 Comments
SissyCrissy6245SissyCrissy6245over 3 years ago
Erotic Thread

Ohhh PantyWriter, what an incredibly descriptive thread you've created with an attentive Sissy following his Mistress' instructions. Turning his psyche and body into the more feminine Gurl he was meant to becumm. Stimulating his clittycock in the "feminine manner" that is so exhilarating for this long time PantyBoi. You've described my SissyGasms in Christine's pretty....feminine lingerie.....purrfectly. Thanks for all of your wonderful "tails"....Mmmm!!! .....xoxoxo ;-)

TheDrunkenNebbishTheDrunkenNebbishover 3 years ago

Anyone who administers punishment of that level, especially when done not to correct errant behavior but for the sheer pleasure of inflicting pain, who does not immediately offer aftercare, hasno right to be called Mistress. That is the mark of a bullying an abuser.

AnonymousAnonymousover 3 years ago
Thank you

i so loved reading the last two stories. The way you have slowly built up the story line and tension is just lovely. i think many of us could only wish to find a situation like this so we could become more of what we would like to be.

Thanks again and i cant wait till the next chapter, not to rush you.

So classy!

AllenJamesAllenJamesover 3 years ago
Lovely luxurious long - and hot story!

Loving her instructions on how a sissy pleases herself, I've been teasing myself all day since I read those instructions - and just can't wait for some alone time to follow them fully and really try this out!!

AnonymousAnonymousover 3 years ago

Heaven what a lovely story being slowly transformed into a perfect sissy by Madam I'm really looking forward to the next episode x sissy Lucy

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