Lessons: First Time

I found her name in the back of a local swingers newspaper, in small print, at the bottom of a column. "Mistress Jade, Private training sessions, Become the man I want you to be." I clipped the ad and carried it around in my wallet for almost a month before I got the courage to call. A formal sounding older woman, who told me that the Mistress was busy with a client, answered it promptly. But she told me that the Mistress was still accepting clients, and scheduled me an appointment for the next Tuesday evening. I worried for the next week if I was doing the right thing, but I was still there on time.

The house was located in an older but distinguished part of town. It was classy but demure, and I felt my throat tighten as I rang the bell. An older woman, who introduced herself as the woman I talked to earlier, opened the door Mistress' Jade Secretary. She showed me into the house, took my coat, and showed me into a room to one side, a library. I spent about half an hour nervously wandering, absently reading the book titles before I heard the door open behind me. I turned and was stunned by the sight I saw.

The doorway framed her for a second; in an entrance Hollywood could not have choreographed better. My eyes started low, slowly climbing the laces of her black knee-high stiletto-heel boots, up her black stockinged legs, past her black leather mini-skirted hips, admiring the white silk shirt that encased her torso, pausing at the black velvet choker, and coming to rest on her face. Her long straight black hair was perfect, and slung behind her shoulders. Her skin was like porcelain, her features exotic, and what little makeup she wore was perfect. I found I couldn't look her directly in the eyes, just darting glimpses. She walked across the hardwood floor, her heels clicking with each step. She sat down in a comfortable chair set on the edge of the area rug, beside the fireplace. I stood there, not knowing what else to do.

"So you wish to serve me do you?" she asked, her voice soft yet crisp, with just the faint hint of an oriental accent. I approached her and began to say yes when she stopped me with a raised hand. "If you wish to serve me you must follow my every command promptly and without hesitation. You are mine to do with as I will; do you understand this?" I nodded assent. "Then stand in the center of the carpet slave," she commanded. I did so, feeling uneasy, but aroused too.

"Strip naked, let me see if you are worth having." I hesitated, and she reached beside the chair and pulled up a leather-riding crop, smacking it against her palm repeatedly. "Do NOT make me repeat myself," she hissed. I slowly, and with as much dignity as I could muster, undressed, throwing my clothes in a heap where she pointed, until I stood before her exposed. She smiled wickedly and bid me to approach her. When I did she used the tip of the crop to examine my penis, still flaccid but beginning to respond to her attention. She then indicated for me to slowly pirouette, and to continue doing so until she said otherwise. I did so, and every time my exposed bum was towards her she would smack it with the crop, lightly at first, but increasing in force each time, until I could almost not stand it. But my cock was also responding now, growing to a fully erect size.

I was embarrassed, my ass cheeks felt on fire, and I was sure that I would soon break into tears. She must have sensed I was going to break because she stopped, and ordered me to my knees in front of her.

"Not bad for a beginner dear," she said as she stroked my flushed face with the now hot riding crop, "not bad at all." She absent-mindedly fondled my genitalia with her boot, and I the few times I managed to look her in the face I saw a thoughtful look there. "I've been trying to decide how you should serve me," she began. "Your very manly normally aren't you? You spend a lot of time being tough?" I nodded assent silently, wondering where she was going with this.

"I need a new sissy maid, do you know what that is?" she asked. I shook my head no as I was unfamiliar with the term; she smiled. "A sissy maid is someone who dresses up as a girl and serves me, privately and at parties as a servant girl. Your duties will include household tasks, and anything else I assign you. At all times you must strive to make sure I am pleased, because if I am not I will take you over my knee and spank you no matter where we are or who may be present. Are you willing to serve me this way?" I felt sick, because this was not what I had bargained for, but I was afraid to make her lose interest in me, so I nodded assent.

A snap of her fingers brought in two naked young women adorned with leather collars carefully carrying a large metal tub filled with water. They placed it in the middle of the rug, and then quietly left. Mistress Jade indicated that I was to get into the tub, which I did. The water was warm, and felt good as I stood in it up to my knees. The young women returned at this point, each carrying a small bag. Each opened their pouch and withdrew a bar of soap, and after lathering them up in the water they began to soap me down. When I was completely lathered they stopped and put their soaps down and reached into their pouches again and withdrew a pair of razors. I must have appeared nervous, because Mistress told me that a sissy maid must be smooth and hair-free, and that I should relax. The women shaved my body quickly and efficiently, removing all my body hair, except for my head hair. It was strangely erotic, feeling them remove my hair, the razor sliding across my flesh. The only time I got nervous and embarrassed is when they had me spread my legs wide, and then shaved my crotch, then had me bend over and shaved my ass crack. When they were done I was completely smooth.

Mistress Jade indicated for me to step out of the tub, and I did so happily since the water was now cooling. She bid me to approach her, and when I did she ran her hands over my body, examining the shaver's work; she seemed pleased and dismissed the women, who took the tub with them. Her gentle stroking of my flesh caused my cock to again rise, which she noticed immediately. She indicated for me to kneel before her, and then spread my knees apart and slipped her boot between them, nestling its pointy toe under my sack.

"You seem to be enjoying yourself so far slave, but I can't have you being erect for the next while" she told me. "Masturbate for me, and close your eyes and fantasize about all the things you want to have happen to you as my slave." My cock jumped at her command, and I quickly began stroking myself, already feeling the pressure building inside. The feel of her boot under my sack was intense, and she began massaging the flesh between my sack and my butt hole; the feeling was incredible. Between that, the scent of leather and the wild and kinky thoughts running through my head it took only a few minutes for me to cum, sending several strands of fluid out to land on Mistress' polished boots. I tried to relax, but she pushed her boot toe up higher, until I couldn't relax. I looked up at her, and saw she was displeased.

"Look at the mess you've made on my boots" she said through clenched teeth. "Clean it up now." My eyes darted around for a cloth or something to wipe it up with, but found nothing. "With your mouth slave" she commanded, "lick and suck your cum of my boots NOW." I wasn't quick enough I guess because she backhanded me across the face, her beautiful features distorted as she again yelled "NOW." I lent over and tentatively licked a small area, at first revolted, but soon found the taste not bad, if not appealing. I began lick and suck my cum up with a fervor only slightly prompted by Mistress' boot toe. I felt so dirty, licking her boots clean, and the comments she made almost continuously did little to help that. "Oh yes bitch, lick my boots, taste your cum as it rolls down your throat, you like it don't you, the taste of cum you dirty girl." When I finished my task she raise the leg to inspect the job, she smiled and then pushed me back on my ass with her foot.

"Stand up slave," she commanded, "are you ready for the next phase?" I was unsure of what she meant, but nodded eagerly. She snapped her fingers, and the same two women returned, this time carrying bundles over their arms. Without a word they began their task, pushing me down to sit on an ottoman that had appeared behind me. They each rolled a black stocking up a leg, and then teamed up to put a garter belt around my waist and connect the straps. The feel of the silky material against my shaved legs felt wonderful, and as they worked on the straps I discreetly rubbed my legs together. They then stood me up and spread my legs apart.

One of them reached between my legs from behind and manipulated my genitalia into the smallest possible package and tucked it down and between my thighs, while the other secured it there with flesh colored tape. It was uncomfortable, but did not hurt. As I stood there trying to get comfortable one of them reached down and grabbed a pair of thong silk panties from the bundle, and the other one lifted first one leg and then the other, and slide them up. As they were put into place, the thong back slipping between my ass checks, the silk front encasing my bare crotch it felt wonderful. Every nerve was ultra-sensitive, and I found myself becoming lost in the sensations. They slipped my arms through a bra's straps, securing it behind me, and tucked a pair of b-cup falsies in to mold them out. I felt odd with the bra on, my breathing constricted, and my chest heavy with the weight of the breasts.

My arms were raised and a one-piece black satin party dress was pulled over my head. It was basic, with a slight flair at the bottom and thin straps over the shoulders. One of the women put a small leather choker around my neck, while the other fitted me into 4" high heels and secured their ankle straps. I sat there, unsure of what to do as the women worked in a whirlwind, finally fitting me with a long wavy brown wig and putting makeup on my face. I felt as if a female mask had been applied, with the foundation and all, and my lips felt weird with lipstick encasing them. The women stepped back and helped me to my feet. The whole process had taken about an hour, but to me it seemed like an instant. On command I pirouetted for Mistress Jade, and I blushed when she clapped quietly the women retrieved their things and were dismissed from the room.

Mistress Jade pointed to a full-length mirror on one wall, and when I saw myself in it I was shocked; it didn't look anything like me! Instead I was a pretty brunette girl, demure, but undeniably sexy. I turned proud towards Mistress Jade, and she beckoned me to her. I couldn't walk worth a damn in the heels though, and after a few steps she told me to stop. "I don't want you damaged dear, so crawl to me instead," she said soothingly. I knelt down and got on my hands and knees and began crawling towards her, careful not to snag my nylons. I felt so wanton and slutty, my ass wiggling as I moved slowly, and my heart raced and my cheeks flushed. When I got to her she had me curl up at her feet and cuddle one leg. It felt so right, like that was where I belonged, that I smiled when she began stroking my face and telling me what a pretty girl I was.

"You have promise dear," she commented, "but first let me explain some rules. Your name is now…. Samantha. You are a sissy girl, and no longer a man. You will not be allowed to act like a man, sexually or otherwise, while you are in my service. The more feminine you become the happier I will be, and the happier you will be in return. Follow my commands and you will be rewarded, disobey me and you will be severely punished. Sometimes you will be punished just for my enjoyment, and you will strive to put on a good show for me. Do you understand?" I nodded assent, happy to be wanted. "Now, for being such a good girl," she smiled at me as she raised her skirt and spread her legs, "I will let you satisfy me orally." As I buried my face into her, determined to make her as happy as I now felt, I heard her content sigh and knew this was what I had always wanted...