The Descent Ch. 03 - The Show

Margaret explained the outfits, there were five. I also saw that for the first time I would be wearing heels. Most looked to be in the three inch variety, although the last two were much higher.

"It's really too bad my niece couldn't see this," Margaret said. "Although I understand your position Cath, she would have been head over heels."

"Maybe a picture. Maybe," Madam hedged.

Finally, I was left alone and donned the first outfit. This was more of a traditional women's lingerie set. It was all white, with a soft, lacy bra that fit me. The ladies had given me an insert to tuck into the bra so that there was at least some form of bust line. The panties were white, and went high up my hips, and then the lacy garter belt that held up the white stockings. White heels finished off the look. My prop, for each of the outfits included a prop, was a small parasol.

I walked back and forth in the back, trying to adjust to heels. I had a sudden insight into why women's feet were always sore. I tottered at first, but with each step gained confidence.

"Are you ready?" I heard Madam call.

"Yes, Madam!" I returned.

I saw the curtains open, and bright lights shone down. I was still in the shadows. I put a hand to my chest, and closed my eyes, and breathed steadily. I was actually thankful for the chastity device, because my clitty was filling it now, and occasionally leaked a little I was so excited. I put the parasol on my shoulder, and began to walk, exaggerating my hip swing.

Into the lights I went, out onto the edge of the walk, and there I stood. I posed (listening to directions), popping hips, and spinning. Bending over and teasing, blowing kisses to my audience of two. My nerves were forgotten; this was fun for me. But then it was time for the next outfit, and I tottered back into the shadows. .

I quick-changed from one to the next, this a sexy black bikini panty with a see-through negligee. My prop for this one was a furry stole to wrap around my neck. I called that I was ready, and performed my routine again.

The third and fourth outfits were more elegant lingerie sets. The fourth was this lacy bustier that I loved from the moment I donned it. It made me wish I had a woman's hips, it was so sexy. That garment, if Madam did not buy, I might buy myself! I came out, and turned, and got claps and whistles, and Madam in particular had eyes as shiny as mine. I think she liked it as much as I did.

And the fifth, and final one, was a show-stopper for sure. More than just a lingerie set, this was like a sexy woman on the make set - going to the club in five-inch stipper heels, and looking like a walking, talking slut. The latex was a bitch to get on, but I finally managed, and walked out to them both standing and applauding me.

I felt incredibly sexy in a decidedly slutty way. Although all night my chastity device kept my clitty in check, at the moment as I sashayed out on that stage, it had never felt more full. I knew I was dripping precummis, and the rapt expressions both Madam and Margaret wore filled me with a delicious pleasure. I bent over, blowing them kisses, turning around and wiggling my bum at them, in general acting coquettishly silly. Yet my heart raced from this pleasure, no matter what descriptor was used.

Both women stood, then, giving me a standing ovation. "Now *that*," Margaret called out, "was truly a show-stopping sissy show!" I grinned, in the limelight of two older, dominant women. Their compulsion to swaddle me in femininity stirred many emotions within me, and I realized that if I were not careful I might burst into tears of happiness.

"Cath, will you let me see his clitty?" Margaret asked, almost breathless. Her eyes shone and cheeks bloomed into a rosy red.

"Oh, well, why not," my Madam said with a grin. "My sweet sissy?" She held out her hand, and I took it to carefully lower myself down to the main floor. Margaret assisted me out of the tight skirt and Madam eased my panties down.

She leaned forward, looking me directly into my eyes. "Do not spill your cummies," she warned me so softly I assumed she did not want Margaret to hear. "Show me that you've built up some control, darling."

Suddenly scared, I nodded while steeling myself for this test. Madam slipped the key into the lock, and undid it, and then withdrew the cage encasing my clitty. Of course it jumped straight up and out, obviously leaking, and throbbing to some extent.

"Oh. Oh...my," Margaret admired me, her tone soft. "Now that is a nicely-sized clitty, not too large and not too small."

"I know, it's a delightful clitty," Madam agreed. She took her hands, and lightly stroked me using just the fingertips. It took all of my self-control to neither moan nor sharply inhale, such was the pleasure of her touch.

"And leaking," Margaret said. "May I?"

"Briefly," Madam allowed, stepping to the side. Margaret stepped before me, smiling as she made eye contact, and then used both hands to cradle and caress my clitty. This time I was unable to hold back a moan of pleasure. "Oh...oh!" I gasped as her fingers caressed and toyed with my body.

"Easy, my sweet sissy," Madam warned.

I looked her way, and nodded, and concentrated on clenching every muscle in my lower body, to tighten and cut-off any chance of an accidental cummies. Margaret released me, stepping back; I took that moment to catch my breath. Madam stepped forward, and tucked my clitty back into the satin panties, and reached around to pat my bum lightly. "Excellent job, my darling," was her whisper for me alone. My heart leapt with joy and lust and pleasure.

We then busied ourselves with extracting me from the rest of the clothing. Difficult though it was to get myself back into the clothing in which I had arrived, we accomplished that. Madam bought several items, which Margaret neatly folded and put into two large bags. The two women exchanged big hugs, and air kisses once again. That act was repeated between me and Margaret, and then we returned to the cold, night air for the fast drive home.

Once inside Madam's apartment, she put her hand on my chest, pinning me to the wall. She looked into my eyes; I was grateful and relieved to see both pleasure and passion dancing in her eyes. "You were marvelous," she praised me once again. "I once had a sissy boy back out of such a show. Yet you seemed to grow into it with each passing moment."

"I do not know why, or how, Madam, but each moment gave me more and more pleasure. Showing off for the two of you - my audience."

She grinned, lifting her hand to my face, caressing my cheek softly. "You did achieve one thing this evening. You have aroused me very well," she said, inflecting into her tone that breathy need I had heard before.

"That delights me, too, Madam," I said as I felt yet another leak come from my clitty.

"Wonderful. Now, since you seemed to take particular delight in wearing that corset nightie number," she said, lifting one of the two bags up with her hand, "I hope that you will be equally delighted to wear it for me now?"

Breathlessly and fast I replied: "Oh, yes Madam, oh yes!"

As before, I felt completely submerged in feminine pleasures while wearing that outfit. The stockings, white and sleek, gave my legs a long, sexy look. The corset, with a crotch strap, hugged me tightly in every place that it could, and its lacy sexiness touched every part of my skin. A skin, I might add, that was enlivened as every nerve ending was active and transmitting. It might have overwhelmed me.

I did my twirls and private dance for Madam. She stood in the doorway of her bedroom, blocking its entrance, her hands held high on the jamb, her legs spread nearly to the width of the door. In the hallway I gyrated for her. Finally, she whispered it to me.

"Kneel and worship me, here, right here, my sweet sissy boy," she gasped. Her skirt fell to the floor, and she had at some point lost her panties. I could not stop gazing at her bared sex, and she reached out to caress my face again. "You know what to do, my sweet sissy!"

I knelt, slowly sinking to the floor, then scooting forward. I tilted my head back, my eyes looking up between her breasts, to her eyes that twinkled, and her mouth parted with need. My mouth and tongue found her sex, the delicious heat and once more fell under the intoxicating effects of her body. I lapped and teased, licked and sucked. She shuddered and gasped, moaning joyously as I gave her pleasure. At some point, it occurred to me how this would look - she, spread-eagle in a fashion, bracing herself at the wall; me, kneeling and obediently giving her pleasure, of course with my clitty rock hard though still trapped in women's undergarments. My hands held onto her thighs, giving me more purchase to dig deeper and harder, my tongue squirming around inside of her body as her walls clung tightly to my sinewy tongue.

Her orgasm hit without warming; one moment, a loud moan and the next a much hotter, steadier flow of liquids that joined with several powerful spasms of her lower body muscles. She twitched and cried out, one hand dropping to my hair, grabbing me tightly. It hurt but did not stop me; if anything, I drove in deeper, finding and drumming her clitoris harder and harder.

"AAAAAAAAAAAAAAAAa!" she screeched, and pushed me roughly away, sending me to the floor. She carefully sank herself to the floor, and curled her legs under her. Her face and chest were rosy pink, and she gasped, panting hard and fast for air. Her eyes remained unfocused for a long while, and only once they regained clarity did they move to me.

"My god I needed that," she admitted. Weakly, her legs still visibly shaky, she got to her feet and walked to the bed, pausing to open a drawer from her nightstand. She turned, and from her fingers showed me what I had coming next. My clitty leaked at the thought of it. "You'll assist me in putting this on?"

"Yes, Madam," I whispered. She had not said to crawl on the floor towards her, but as I did so, watching her face, I saw it once more light up with intense happiness. She nodded, and dropped the strap-on harness to the floor. I got to her feet, and set it up, then held and ankle to gently and carefully put it into the right place. Once the other was done, I slid it up her body slowly. The dildo was already attached, a smallish, bright pink one. Up and up it went, until I was kneeling face-high with it, and she then busied herself strapping it tightly to her torso. She saw me looking, and once done, gave me a wink.

She had me get onto the bed, and kneel in a face down, ass-up position. I had never felt so vulnerable in my life, knowing my clitty was so hard, and my ass so opened for her. "I do hope your boipussy is ready for this," she said. "You are a virgin, are you not?"

"Yes, Madam," I admitted.

I felt hands, on the hips, digging into the material, easing it down my body. I felt the cool slipperiness of the lube fall onto my body, slide down between my cheeks and pool a little at my small, tight opening. Her fingers improved the application of the lube, a pleasure eliciting a shuddering moan from me. The bed shifted again, movement, and I assumed that she was positioning herself.

Two hands fell to my hips, a sharp crack accompanying it. The head of the dildo pressed to my boipussy. That made me moan, and I felt the urge to push back, to impale myself on it.

"No, no," she said, seeing my body's tense, and anticipating my movement. "This is for me to do. You take it, my sweet sissy boy."

Muffled: "Yes, Madam!"

She just held herself there, the head pressed to my opening. I was moaning, and felt yet more precum ooze from my clitty. One hand moved from my hip, and I braced myself a second before she delivered a crisp slap to my upturned ass. The movement thrust the head forward a little, beginning to ease its way into my virginal tunnel. She spanked me a second time, and the head eased in just a little more. A third, and now my anus began to stretch, accepting the head. "That's it, my sweet sissy boy, take this cock in your boipussy. Beg me! Beg me to fuck and fill you boipussy!" she demanded.

I turned my head, careful not to push backwards, suppressing every urge I had in my being. "Oh please fuck my boipussy, Madam! Fill it up, thrust it into me, oh I want to feel that cock in my boipussy!"

"That's good, my sweet sissy," she said and I felt her pressure me. The head moved, and began to stretch and push.

"Oh oh...oh...fffuuucckkk..." I groaned as it inched and wormed its way inside. It felt big, hard, strong, thick, and filled me. And impassioned me; my clitty throbbed under my body. She spanked my ass once more, a distraction; her hand holding my hip gripped it tightly, and she thrust roughly, slamming the cock home.

"UUUUAAAAAAAAAAAAAAAAAAAAAAAAAAAAaa!" I screamed, as what started as pleasure turned into mortal agony!

"Take it, bitch!" she yelled. "Relax," she added a second later, less harsh. "Relax, sissy, your boipussy can take it, that's it, relax darling..." she said.

The pain faded, not quite as quickly as it erupted. With the decrease of pain came an increase in pleasure. "Oh...oh Madam!" I said finally. "Oh, it feels good!" I told her.

"Oh yes?" she asked, and I felt it withdraw, my tight muscles gripping it but the lube made it easy to slide out. A pause, and then back in. With the insertion, my lower body clenched, sending my erect clitty pulsing hard against my belly. It was fully buried.

"Oh!" was about the only thing I was capable of saying. That and "Mmmmmmmmm" as her thrusts began to move in slow rhythm. Each penetration made me more deeply hers; each penetration left me in a deeper state of complete arousal. I had never known such pleasure, bent over and fucked. Oh god it was good. So good.

My moans picked up, as did the rocking of my hips. "That's it, be a good slut, fuck that cock," she growled as she saw my physical reactions. "That boipussy likes its cock?"

"YES MADAM!"

"Work it now, fuck it, sissy. Fuck that cock. Yes, that's it. Go full slut, sissy, let me hear you go full slut!" she moaned.

"MADAMmmmmm oh god it's so nice filling my boipussy oh god please!"

"Fuck you harder? Sure!" she said, and then I was treated to a new pleasure, of being held and fucked - hard. Her body slapped against me, sending my clitty and sack flying every which way. Her tight grip on my hips kept me in place, and she was skilled at fucking with her strap-on, for she did not miss a beat. I felt a deep pressure building in my body, especially as her cock began to rub me in a delicious way. It almost felt like the most insane need to pee I'd ever felt, except that it was pure sexual ecstasy.

"M-m-madam..." I stammered. "Oh...oh god...M-Madam...oh...oh..."

"Mmm take it bitch. You like it? Sissy slut!" she laughed, but not cruelly. She was enjoying herself, knowing how absolutely aroused this made me. She could see it. I pushed back into each thrust, willingly meeting it, pushing the cock in deeper, creating more pleasure.

*slap* She cracked her hand on my ass, hard. *slap* Another to the other side, and then a third for good measure. Then, she pulled it out, and leaned back.

"How does my sissy boy feel?" she asked.

"G-good, so good Madammmmmm," I moaned.

"Close to spilling your cummies?"

"Yes."

"Good. Because the only way you're spilling your cream is with this cock in your boipussy. If you can't come, then you can't come," she warned me.

"Y-yes Madam!" I moaned.

"And I want to see you fuck me, I want to watch," she intoned. I felt movement again, and after maybe twenty seconds of commotion on the bed, was directed to turn, then kneel. She was flat on her back, her breasts pulled down and to the side via gravity, her slickened dildo pointing up in the air. She pointed, and I climbed atop her, positioning the cock against my boipussy, and then sinking down atop it.

She had had me do this during that lapdance, and I found it so much easier to break into rhythm now. Each rock of my hips, each time I drove her toy into my boipussy sent my clitty swaying and moving in big, fast circles. She held my hips, occasionally reaching out to caress my sack, but for the most part remaining silent, merely watching me fuck her dildo. The orgasm sensation grew and grew, and then I sat back, fully impaling myself on her cock.

I arched my back backwards as the dam burst. "OH MADAM!!" I screeched. With the cock buried in my boipussy, my hips pushing down on it, my back arched backwards, and my clitty pointed out and up, it released. I had never felt such a powerful orgasm, and Madam yelped herself. I could not look, my eyes shut tightly, feeling the spasm as shot after shot of my sissy creams spewed out of my clitty. I breathed wildly through my mouth and nose, all through a deep moan of mind-blowing pleasure.

When it ended I could barely catch my breath, and then moved forward and opened my eyes. Madam's face was covered in my cream, with droplets on her forehead already running down to her eyes, and droplets on her nose, lips and chin. Droplets covered her chest, sprayed wide, covering breasts. The last blasts, lacking the same pressure as the first, formed large puddles on her abdomen.

Without missing a beat, I leaned forward as the dildo-cock slipped from my no-longer-virginal boipussy. I licked her face, and her lips, carefully getting all of the cream onto my tongue. Her chin, then her breasts. Slowly cleaning her with my tongue. Lapping it all up from her belly, and now it was my belly warmed with the ingestion of my own cream. I did not stop until I was certain it was all cleaned up. "You are clean, Madam," I told her softly.

She opened her eyes, and smiled in a mischievous way. "Wait until I tell Margaret about this!" she laughed. She patted the bed, and I fell onto it, and she spooned me, slipping the dildo between my soft thighs. She held me tightly, her warm breath at my ear, and a wave of emotion hit me. It was so hard, so sudden, and so overwhelming that I began to shake uncontrollably in her arms, and I felt tears beginning to stream from my eyes.

"M-m-m-m..." I stammered but then the torrent of emotion stole my speech. In an instant, I was drowning, in my own emotions. I clung to her arm, weeping and shaking as the sobs wracked my body. A part of me felt her cling to me, pulling me into her, wrapping me in warmth and protection. It was blissful, yet deepened the torrent. My brain registered her soothing, soft words, her warm touch, her tight embrace, and as I sank deeper into her, it broke the torrent. It receded as rapidly as it started, but in its wake I was left utterly exhausted, emotionally and physically spent. Nothing I had experienced in the past came close.

"Shhhh, darling, you're all right, I have you, I'm holding you, easy now darling, it's all right, you're safe with me," over and over she said this. Softly, gently, holding at all times. Control over my senses and emotions returned; in its wake I felt a new one - shame.

"I'm so sorry," were the first words I managed to coherently whisper.

"Never apologize for that," she said softly. "It was a gift you gave to me."

"How?"

I felt her warm lips press to my sweaty back. "It means that you were so deep, so full of your submission to me, that rising from that triggered that emotional burst. It's a sign of how deeply you went, which in of itself is a gift."

I nestled back against her. I was a mess. "Do you have tissues?"

She chuckled, and some were produced which I used. After setting things aside, I snuggled back into her. I had never felt such an emotional attachment before. The awe I felt had no apt description. "I feel so close to you right now, Madam," I whispered.

"I feel that same attachment, darling. No," she said suddenly. Using my name. Repeating it. "You have made me happy in a way I've not felt in a long time. Years."