The Descent

It had to be too good to be true, I thought. No woman had ever come on to me like that before. She was pushy and for all intents and purposes, demanded that I escort her to this dinner date in the city. Sure, it was Valentine's Day, and she did admit earlier in the night that being mid-50s and single on this day agitated her; hence, she demanded my presence. I had smiled softly and assured her that I understood, and understood as well that this was the only apology I was going to get.

I did not mind. She was a gorgeous woman, I thought. She was British, and was working on a visa for two years in the city. We lived in the same building, me, new to my job, my career, and this city. She, older, experienced, wiser, an international expert in banking, and she had taken an interest in me. It made no sense. None.

Yet, as curious as her interest in me was, we had found some good conversational rhythm over supper. It was one of those places that catered to couples, and on Valentine's Day the place was packed. But she had secured a reservation, and we were at a distant and relatively isolated table. Eating our meal slowly while the two candles provided the light and romantic atmosphere was simply the most outstanding meal I'd ever eaten. The food was delicious, the setting something out of a fantasy, and the company beautiful and interesting. What more could a guy ask?

The dessert arrived, plated gently and precisely by the well-trained staff. My date, Catherine, thanked the server in her usual courtly manner. She looked at the chocolate cake, and then up at me with a wry grin. "An extra hour at the gym tomorrow, but it's worth is now!" With that, she forked up a slice and put it into her mouth. Her eyes closed as she chewed, with the luxurious chocolate flavors filling her mouth. She swallowed and grinned at me. "Delicious."

I had opted for an apple pie. Mine was as good as hers. Sugary and delicious, and warm mixing with the cool of the cinnamon ice cream. I assured her that mine was as delightful to me as hers was to her. She smiled. Her simple glasses reflected the dancing light of the candles, and framed her face perfectly. Her dark hair fell around her face in a manner that must have taken quite a while to get just right, but the effect was worth it. Dark red, maybe ruby-colored, lip gloss highlighted her face, and each time she smiled I found my eyes drawn to her lips. I wondered what those lips would taste like, or feel like upon mine.

"Do you have further plans for us this evening?" I asked.

Her smile was confident, but revealed little. "Oh, yes," she assured me softly. "I do."

I felt my smile falter a little. It was how she said it, so confident, yet demure in a way that made my penis jump and not just a little. "Are you going to share?"

She lifted her wine glass and took a sip before making steady eye contact with me, smiling again in that mysterious way, and slowly shaking her head side to side: no. She set it down and put her hands atop the table, palms up. Clearly indicating I should put mine into hers, which I did without hesitation. They were warm and soft, clearly feminine. "You would regret saying no to me," she promised.

"You make it sound so..."

A little squeeze with her hands cut me off. "Trust me, darling," she said quietly. Her hands squeezed mine again as she spoke, leading me to simply remain quiet and nod slowly.

We left the restaurant, her arm crooked into my offered elbow. We looked like a fancy couple, to be honest. I was dressed well, in a sweater with a jacket over top of it, and she in a dress that was one step below evening gown, and several steps above office attire. We hailed our Uber, and rode back to the apartment complex in silence, but the entire time her hand held mine tightly. We exited and I was steered to her place. Whatever plans she had in mind, they were going to start now.

She guided me inside. She patted my arm, an act I took to mean stay put, and went inside her darkened apartment. Shortly thereafter I heard the click of a lighter, and then the wall reflected the dim lighting of a candle one at a time. "Okay, darling, come to me," she said softly.

I walked in, to see eight candles lit, placed strategically around her living room. She was seated on her sofa, her legs crossed, the dress opened at the slid to show those lovely legs encased in hosiery. I paused at seeing her, sitting so demurely and sexy, and then resumed, walking slowly towards her. She patted the sofa, and I took a seat next to her.

"Nervous?" she asked.

Exhaling slowly to control myself, I agreed with her.

"Don't be overly nervous," she said. "I won't do anything to you that you cannot handle," she quipped.

"How do I know that?" I said as my voice shook a little. "You don't know me at all!"

Her demeanor remained passive, if the smile softened a little. "True. But all my boys love being with me, and I with them, and so I fully expect that it will work out."

"All...your boys?"

"Yes, darling. I have many boys that adore me, and want to pamper me and they're so sweet, they do exactly what I want them to do. Always. You want that, too."

"Wait - what?"

"I can tell, darling. You have been waiting, to be told what to do, all night. To obey me."

Did I gulp? Maybe. "O-obey you?"

"Yes, darling," her silken voice confirmed. "Tell me," she said, tilting her head a little to one side, "if not the thought of obeying me does not leave your..." and here she tilted her head, angling down, towards my crotch, "...organs in, shall we say, a rather provocative state?"

Damn the woman! How did she know that my cock had stirred in my pants. Then again, it had been stirring most of the night.

"And," she continued softly, "I do say that obedience has its rewards."

I felt like I was a fish, seeing the bait, recognizing the bait for what it was and knowing its danger, and yet unable to stop from nibbling at it. "What rewards?"

She smiled. "Only good, obedient boys get to learn about their rewards," she said. She put her wineglass down. "Stand up darling."

Before I had a thought to question why such a command was issued, I was rising. She smiled, triumphant. "See?" she said. "Now I have three types of boys," she said. As she spoke, she ticked them off of her fingers. "I have fuckboys. I have enough of them right now." Tick went the second finger. "I have two panty-boys at the moment. Neither of whom seem to be capable of graduating, so to speak, to my third, and favorite boy." Tick went the finger. "Of which I have none right now," she said in a voice so soft that I had to lean forward to hear. "My third and favorite boy is a sissy boy. And I think you, darling, are well qualified to be my sissy boy."

"S-sissy b-boy?" I stammered it; there was no question. Why was my heart racing so? My mouth completely dry. A huge ball of heavy heat erupted into life in my belly. My vision wavered, just a little.

"Yes. A sissy boy. Different from a pantyboy in that my pantyboys are not permitted to get close to me. They want to remain apart from me, and lack the intimacy of my best sissy boys. A pantyboy will wear panties for me. Will cum in his panties for me. And will do other things for me. But that's it. A pantyboy is afraid of his own soul, and refuses to admit that he's merely a single step from his true calling - a sissy boy." She blinked once at me. "I see you, however, as a fully sissy boy. Yes, the panties. The little clitty and wanting to always shoot your cummies. But the shaving. The wearing of full intimates. Of touching me, and satisfying me, fully and completely, that is a right that only my sissy boys get. When I want fucked, I call a fuckboy. When I want to make love, I call a sissy boy. And truth be told, I much prefer to make love than fuck."

"But..."

"Judging from the tent in your slacks, sissy boy, I already have my answer. So tell me, was it your sister's or your mother's panties from whom you stole and wore the first time?"

"N-neither, she was my...um...a college girlfriend."

She nodded slowly. "And did your paramour ever learn of your treachery? Of stealing her intimates so that you could wear them, masturbate with them, ejaculate into them?"

"No!" I replied in a strangled voice. That leaden ball of heat in my belly moved north, and it cause my face to inflame. I felt that I was glowing red in the darkness of her apartment.

"Have you ever admitted this to anyone?"

"No," I gasp-whispered.

"Address me as Madam."

I quickly licked my lips and nodded several times. "No, Madam."

"Was that hard to do?"

"No, Madam."

"When your clitty is hard, how long is it?" she asked me next.

Once more my face brightened, but in the darkness I suppose it was hard to see that. "A-about five inches, Madam. A little over, actually," I amended hastily.

"You have measured?"

"Yes, Madam."

"Tsk." She shook her head, clearly disapproving. "Such a boy thing to do. To measure up. When all a boy really wants is to please, and be pleased." She lifted a hand and took mine in hers. Felt my racing heartbeat when she placed a finger over the inside of my wrist. "There is nothing to be frightened of. This," she said waving her other hand widely, extravagantly, "is merely awakening your true inner nature."

"Ho-how did you know? Madam?"

"I suspected. Some boys are boys, masculine, ignorant, bull-headed, selfish, lacking a touch into their own emotions. Some are beyond hope and beyond help. I have no wish to consort with such boys. Other boys are mesmerized by the feminine. You have been immersed in me all night long. You are drawn to my elegance. I have seen in it the delicate treatment you have of me. I will not break," she said breaking into a sudden smile.

I found myself nodding. "All of that you said is true...Madam," I added again.

"And as I said earlier, some boys are afraid of their own nature. They will wear panties and cum in them, because it's their fantasy. But to truly live that role? To immerse one's self in the feminine? Let me ask you this: have you ever wondered what it would be like to make love, as a woman?"

My voice could barely speak. "Yes, ever since I was old enough to know what sex was," I admitted. It was the first time I'd ever said *that* aloud.

"When you thought of it, what did you think of? Describe how you would want to be made love to, as a woman, to me? You can be blunt and descriptive, and use the dirty words, my darling. I must say...hearing such talk does turn me on," she added.

Hook. Line. Sinker.

I thought about it. Not for long. "I would be in a darkened room, lit by candles, like this. Wearing good lingerie. I would want to turn him on. To touch him, to stroke his cock, making him hard, so hard so want me. Knowing each stroke of his cock would make my pussy tingle. Would make me so wet. Then he would hold me, firmly, not grabbing, but firm, and lower me to the bed. His mouth would be on mine, then on my breasts, nibbling and sucking my nipples. Easing my wet panties off of my legs, easily, smoothly, and tossing them aside. His hands would run up my thighs, parting them, his fingers testing me to find me so wet. So willing. Climbing atop me, staring down at me, watching my face as he holds his cock to my opening. I would feel it, the thick cockhead, resting at my opening. And he would push, sliding it in so easily, each tiny movement sparking ecstasy in me. My eyes, still on him, my back arching, thrusting my chest up, mouth opening sucking in air, as he sank his cock into me." There, I finally stopped this recital that just popped into my head.

"How very descriptive," she said, her voice light and pleased. "You would be under him, submitting to his cock, to his will, to his strength."

"Yes, Madam," I said, paused, then continued. "But enveloped by it. Held by it. Kept...safe by it, I guess."

"Very apt. And true." She nodded. "Remove your pants and your underwear. And socks," she added.

My cock was rigid as I extracted myself from my clothes. She studied me, my thin legs, and my privates. She lifted the shirt from me, and a moment later I was fully naked. I stood with my hands clasped in front of me, opening and closing the fingers, betraying obvious nerves. She took my hand in hers, and guided me down until I was perched on her lap, atop her still-crossed legs.

"I am a demanding Madam," she began to lecture me. "Obedience is a key. I reward when you please me, and punish when you disappoint me. Failing in obedience is the number one way that you will disappoint me. I do not punish because it pleases me; I have no wish to hurt you. But I will spank you, should you fail me. You will let me guide you, not because you have no choice - you always have a choice. You can leave me at any time. Just say it. But you will not say it, because you will want me to guide you. You will find the most erotic pleasures when I guide you. Your entire life will change. But you will not be unhappy. You will glow. Being this way will become your true calling in life. I have a feeling about you."

"Yes, Madam," I said in a pause. I felt I should say something; it was a natural pause in her lecture.

Her fingers found my organ, and lightly circled it with her fingers. "This is now mine. It is your clitty. Let me hear you call it my clitty," she said.

I had dreamed about doing this, in my darkest fantasies. So it was little surprise that my lower body clenched so hard as I spoke those words aloud, and yes, I felt a leakage of precum. "It is your clitty, Madam."

She squeezed me gently. "Wonderful, darling. Simply wonderful!" She gave me a slow stroke, enough that it got a groan from me.

"How often do you masturbate your clitty?"

"Usually once a day. Sometimes twice. Rarely more than that."

"I see. Always to orgasm?"

"Yes, Madam."

"And have you ever played with your little boipussy? Your star? Your asshole?" she clarified further.

"No, Madam."

"Have you thought about it?"

"Yes, Madam."

"What about touching another man? Have you ever done it?"

"No, Madam."

"Have you thought about it? Fantasized about it? Surely you have, given your description of making love to a man."

"Yes, Madam, both thought about it and fantasized about it."

"A hard, thick cock leaking precum, and you on your knees, prepared to suckle and worship the real man's organ?"

My body spasmed again, hard. Which transmitted to her, I knew. "Yes, Madam."

"I shall give you a task. Your task will be to remove every iota of body hair on your lower body, from the waist down. Have you dreamt of having such an order?"

"Yes! Yes, Madam," I said more softly, "I have dreamt of it."

"And did it arouse you?"

"In fantasy, yes. Hearing it now, yes, Madam," I agreed.

"I have a large bath, with plenty of essential oils and fresh razors. If you want..." she trailed off.

"I would be pleased to do it for you, Madam," I assured her.

"Now, then?"

"Yes, Madam."

"Oh, I knew you were going to be the most special sissy boy." She patted my naked bum, and I stood. She guided me into the bath, and drew a hot bath. Once it was ready, she held my hand as she eased me into the bath. I was submerged in the heated water made into a sensual moment by the essential oils, and her sitting there, smiling down at me.

We chatted easily for a while longer. After a ten minute wait was up, she had me begin to shave. Slowly and carefully I shaved my legs, front and back, and then worked carefully on my pubic region. She assisted me there, careful not to touch me overly much for I was still straining erect. Finally, though, she had me stand and inspected me critically. Satisfied, she gave me a moisturizer I used over my entire body as the water drained, and then got me out.

"Now then, my sweet sissy boy, follow me," she said and walked out. I followed her into her bedroom, which was as nicely appointed as her living space. She brought me to a closet, and opened it. There was a short chest of drawers in there, under rows of dresses. She opened it, and gestured to it. "Pick your first pair of panties to wear for me, darling," she said.

I ran my fingers over satin and silk. Colors and shapes and sizes. My co...clitty! My clitty throbbed as I envisioned sliding them up my now smooth, silky legs. Tucking myself into them. I finally found a pair. A deep burgundy. Satin. I gave them to her. "I would like these, Madam," I said.

"A very good choice, my sweet sissy boy," she breathed softly. She then opened another drawer, and looking at the panties I'd selected, then selected the intimate wear for me.

"Now then," she said, taking the items and sitting on the edge of her bed, "let's see you put these on." "These" were stockings. I took them and slipped my foot into them, and gently walked them back and forth up my legs. Without hair, they slipped on easily, until my legs were encased in the one. After the second I felt that my erection might never go down, and then she had me slide the panties up my legs. She fussed around with them until the garment fully covered my clitty.

"Nice," she said. "That will do for this evening," she said softly. She pulled me up onto the bed. "Now I wish for you to make love to me, as a sissy should do with her Madam," she said softly. She stood, and unzipped her dress, allowing it to fall shapelessly to the floor. She wore black lingerie, bra, stockings, panties and garters. She looked impossibly beautiful.

She climbed onto her bed, and laid on her side, guiding me into her arms. We lay there, looking at each other, her hands climbing all over me. Her touch was so soft that it left me breathless with lust. We kissed, lightly and gently. These too left me gasping with need for her. "My sweet sissy. You want to make love to me so badly."

"Yes, Madam."

"I want you to as well. I expect that you will satisfy me fully," she said. I took it to be a challenge. And a warning.

She rolled onto her back, and gently parted her legs. I rolled towards her, and kissed her arms. To her breast. My reward for that was a gentle exhale, and a murmur of pleasure. I began kissing down her tummy, moving slowly. She let her leg drop, and then I slipped over it, and then found myself face to face her with panty-covered sex. I bent and kissed her through the material, enough that I got a slight wiggle of pleasure from her.

"Take it aside, my sweet sissy," she whispered. "Taste your Madam," she urged. I took my fingers and carefully pulled the material to the side, and then kissed the upper part of her pink, blood-engorged lips. The scent was heavy and musky, and each breath seemed to increase my need. The taste was erotic and beyond pleasure. I nibbled and licked, and when her hands found my head to guide me closer into her, I rather lost it.

From then on it was the mashing of tongues against hot, slippery flesh, and the texture of how that flesh gave way under the pressure. How her hips rose to meet me, greedy and powerful and strong, and how her cries of pleasure filled my ears. It was rapture, to hear her pleasure. It was sublime to lap at her. Over and over my mouth serviced her, touched her, pleasured her. The growing crescendo came to its final climax, with a screech, a hard jolt of her lower body, and then several rapid gasps for air. She pushed me away, a weak "no more!"

She took several breaths, and then smiled down at me. "You look you are ready for more worship?" she suggested.

"Yes, Madam," I agreed.

"Excellent." She rolled over, throwing a leg over me, and then brought her legs together. She lay face down on the bed, her round, lovely rump up in the air a little, over the tops of her stockings. "You will worship all of me, my sweet sissy boy," she said.

I looked at the humps, and inhaled once to steady myself. I then climbed between her legs, which she opened a little, and moved up until my nose was nestled between her two cheeks. I used my hands and spread her apart, and looked at the tight, pink nether opening. One I'd never touched before. I was hesitant, that first time, but then as she moaned and I detected nothing out of the ordinary, it became just another part of her. A part to be worshipped.