Cassandra Ch. 01

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Matt's love changed him forever.
10.8k words
144.9k
45
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Part 1 of the 2 part series

Updated 09/22/2022
Created 02/13/2004
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Cassandra is a tease, a flirt, a slut, a girl who lives very much for the moment. Unconcerned with propriety or fashion trends, she dresses in clothes that go right for the jugular of a fetishist's libido. Spandex, leather, latex, spike heels, corsets, overdone hair, make-up and fingernails - these are her stock-in-trade. Cassandra flaunts her outrageous body with wanton abandon. She is soft, sinuous, seductive, an open invitation to sample her treasures. Many have. She craves cock and has had more boys that she can possibly remember - or ever care to. "I can have cock anytime," she muses. "I don't need a boy to make me feel complete." Some might regard her as bizarre, perverse, obscene. Cassandra doesn't. She loves her life, and herself, more now than she ever has before.

Girls like Cassandra are made, not born. Bit by bit, Cassandra was guided, shaped, molded, transformed into everything she is today. It took time, patience, dedication, perseverance, and lots of love. It took Melissa. She is Cassandra's roommate, friend, confidant, fashion advisor, counselor, personal physician - and Mistress. Melissa is also the one, true love of Cassandra's life, forever and ever. Who would know better than I? As I said, she made me everything I am today - and so much more than I ever dreamed I could be. I had been 'dressing up' as long as I could remember. My early attempts were crude, to be sure. I 'borrowed' things from my mother and sisters and kept practicing, experimenting. I hadn't really developed a feminine persona yet; I just had an 'urge'.

My hobby was a solitary one. In my hometown, such a thing "just wasn't done". I didn't dare reveal myself to anyone. The boys' vulgar jokes and derision of "Faggots" and "Drag Queens" scared me off. I wanted the girls to like me, to accept me, and they did - but only as a friend. They perceived me as "too small", "too thin", "too pretty", and "too swishy" to be boyfriend material. They used to talk around me as though I was one of them, gossiping about hair, makeup, which boys were "real studs" and which girls had "made it" with them. The girls were only teasing me, but I was living for it.

I went to college, studied Computer Science, and played at being "One of the Guys". I went to football games, out to the bars, rode my motorcycle, and dressed very 'butch' - though with stylishly-long hair. It was more difficult to pursue my desires at school. There really wasn't much privacy in the dorms, so dressing was out. I moved off-campus to more private accommodations as soon as university regulations permitted, but even then I had roommates, homework and projects to contend with. I picked up scene magazines; "Cosmopolitan", "Elle", "Vogue", and specialty hairstyle and make-up magazines. I bought makeup, styling gel, hairspray and a set of hot rollers and spent whatever private time I had painting my face and styling my hair, then dressing in some cute little outfit I had pieced together. I spent my precious stolen hours in feminine bliss and dreamed of a day I could dress up without fear of being discovered.

During the spring of my senior year, I saw a promotional flyer for a seminar on 'Alternative Sexual Lifestyles'. I awaited the event with anticipation. At last, I would meet 'kindred spirits', people who saw sexuality as more than "Me Tarzan, you Jane", or "Paradise by the Dashboard Light". The seminar was a complete waste of time. It was an amateurish forum by campus gay and lesbian activists to vent their spleens against social injustice - at least, where it was unjust towards them. Nothing at all was said about the other variations on the 'Alternatives' theme. But there WAS Melissa.

I sat next to her (on purpose) and we began chatting between speakers. I was 'traveling incognito' in jeans and black leather biker jacket and carrying my helmet. She was spectacularly beautiful; long, thick, streaked hair a la Cindy Crawford, big, wide-set blue eyes, full, pouty lips. Melissa was not particularly well-built, but so what? She was engaging, effervescent, smart, sassy, sexy and self-assured. And, she was HERE! That had to mean SOMETHING. She was the kind of woman I could lose myself in - and did.

We became lovers almost immediately. I couldn't believe it; she wanted me passionately! I was new to these things, but I sensed something developing, something deep that neither was willing to discuss. There was so much I wanted to tell her, so much I wanted to share, but I was afraid to open up to her. I think she felt the same way; we didn't even discuss why each of us had been at the seminar. In addition, I could sense almost from the start she was involved with someone else. Don't ask me how; call it 'female intuition'.

After a while, she just stopped seeing me, stopped returning my calls. I was hurt. I didn't understand. I wished we had had more time together, time for me to summon the courage to say the things I wanted to tell her. I resigned myself to the loss, but she haunted the corridors of my mind for a long time.

I earned my degree, moved to the city, and landed a good job at Barnes and Bidwell. I hit it off well enough with my co-workers, especially Gwen. She worked in Human Resources (they don't call it "Personnel" anymore) and helped me fill out the myriad of forms that goes with a new job. We had lunch together and she introduced me to her girlfriends: Peggy from Human Resources, Beth, and Lisa from Word Processing, Melanie from Payroll, Suzie from Administration, Nancy and Gayle from Accounting. They made me feel so at ease.

Before I knew it, I had friends - and girlfriends at that! I found an apartment (my own place at last!), started shopping for my 'special things', hung or put them away in their own places in my closets and dressers, and settled in to practice my own version of The Good Life.

I kind of drifted into the Drag Queen/Transsexual scene. There were some substantial differences between me and them; I had a job, paid my own bills without selling drugs or hooking, wasn't all that interested in the latest music by Des'ree, Pebbles, or Salt n' Peppa, didn't want to compete in any pageants, and wasn't looking for a 'husband'. I didn't even dress at first (after all this time 'in the closet', I was too afraid of looking silly), while most of them were living 24/7. Still, I felt comfortable there. I had finally found others like me who enjoyed being as feminine as they could be.

I was fascinated by the fact they all had femme names and personalities, even if it was all illusion. Well, why not? I had been living the same illusion all my life. It just made sense; it was an entirely different 'me', who deserved her own identity. I certainly didn't want to get all dressed up, go to a club, and introduce myself as "Matt". I spent the rest of the week thinking up a name, thinking up the right SOUND of a name, to compliment the woman within me. I literally woke up in the middle of the night with the answer - and the resolve to make it happen.

That Friday night, I took a long, luxuriant bath and shaved my smooth, supple body. I then carefully, exquisitely painted my pretty face. Next, I dressed in red lace waist cincher, bra, bikini panties and garter belt, sheer black stockings, red spandex tank dress, red patent belt and red patent five-inch spikes. My bra cups were filled out with very realistic (and hideously expensive) silicone breast forms that jiggled as I walked. I donned my flashiest hair and pinned it tightly to my scalp. "If I only have one life, let me live it as a blonde," I mused. I added equally-flashy necklace, earrings, bangles and ankle chain. I added long, crimson press-on nails for drama, then spritzed on a liberal amount of "Obsession". Thus, "Cassandra Santee" was ready to make her debut.

The city had a number of clubs that welcomed girls like me, not to mention those who admire us. I vowed I would experience every one I could find. That first time, I would have been satisfied with a smile or two; perhaps even an appreciative "nice". I never expected to be as well-received as I was. I don't know how many times someone (usually another cross-dresser or a 'straight' guy who liked "chicks with dicks") stopped me and told me I was beautiful or sexy. Even some of the queens said I looked good - for a "rock" (whatever that meant). It was faint praise, but better than none at all. All in all, my first time was a lot of fun.

In time, I became known around the scene and was welcomed warmly wherever I went. I made some friends, including cross-dressers, Queens, gay boys, even bouncers (always nice to have around when you want to get in without waiting in line or to get rid of some abusive Yuppie jerk). I found out I had more in common with the Queens than I had previously thought. Once they got to know you, they were a lot more fun to be around than the "weekend warriors" who wore opaque pantyhose and long sleeves to hide their hairy legs and arms. We hung out, danced, got a little drunk, and just had a good time. We even ventured to some of the straight clubs when they had special events. The management loved us; we were exotic and controversial, which made us "cool", and their club the "cool place to be".

I learned the local idiom and grew comfortable in conversing in it. For instance, I finally found out a 'rock' is a (usually new) girl who has not undergone any kind of physical transformation (hormones, implants, or other cosmetic procedure). This is not to be confused with a "rock star", who is a girl on Crack. My new friends gave me tips on dressing, 'tucking', makeup and hair and other tricks of the trade. They told me they got their curvy bodies through a combination of hormones and "pumping" - silicone injections - and recommended I get myself "done". "We know this great doctor," my friend Naomi told me. "She's fish (genetic female), but she's really into us 'girls'. She gives us all the 'mones we want. Just say the word, Sugar, and I'll fix you up with her. Girlfriend, you would be sen-SA-tional!" I was a bit awed by the fact that a physician - genetically-female at that - would take an active interest in the scene. I made a mental note to inquire about that later.

This Jeckyll/Hyde existence went on for a couple of years. 'Matt' went to work at Barnes and Bidwell five days a week. He worked hard, made a good living, had fun with his friends at work, and went home. From time to time, he went out shopping "for his girlfriend", buying new clothes, shoes, jewelry and makeup. He frequented a wig shop owned by a gay hairdresser who was only too happy to help out. Then 'Cassandra', a creature of the night, prowled the dark, forbidden places where good girls and proper people didn't go.

Gwen and the other girls at work took an almost-motherly interest in my personal life. I think the dears were actually worried I went home and watched television every night. They casually inquired if I was seeing anyone. I just smiled. "No one in particular," I replied.

"Why don't you come out shopping with us sometime, or for Girls' Night Out? You can be an honorary 'girl' for the evening. It's almost like you are one of us as it is."

If you only knew.

"Thanks. I just might take you up on that some time."

Halloween is always a special occasion in the scene. Everyone turns out - and really turns it on. All the straight bars were featuring costume contests with cash prizes for the best or most original costume. There was even a contest at work. Gwen chided me for not wearing a costume. "It's only once a year. C'mon, loosen up!" I managed to keep a straight face.

"I have one, but I'm saving it for tonight. It's kind of involved and I don't want to ruin it."

I would have loved to show everyone my 'costume', but thought better of it.

I was at the bars and had just danced a set up on one of the risers. My sleek, shiny, form-fitting latex dress hugged a nipped-in waist and realistic-looking silicone boobies. I danced expertly in five-inch black patent stilettos. One of my bouncer friends had helped me down and I was headed for the Ladies Room to freshen my makeup.

"You looked really HOT up there, Girlfriend. How about a drink?"

I turned around to see the source of the sexy, feline voice that authored the invitation. MELISSA! My heart shot into my throat. After all this time, and now to see her again...LIKE THIS!

And this wasn't the Melissa I remembered. This Melissa had BODY! It was all I could do to not stare at her magnificent breasts, tiny waist, and full, flaring hips, all poured into a figure-hugging black calfskin bustier sheath with matching thigh-high, spike-heeled, lace-up boots and armpit-length black kid gloves. A black-and-red Heartwood flogger dangled casually from a clip on her multi-stranded chain-link belt. Her hair and makeup were as severe as her Dominatrix garb - almost as dramatic as my own. And something else - the gleam in her eyes and slight twitch to her broadly-smiling lips told me she was tripping on Ecstasy. If she recognized me, she didn't show it. Finally, I gathered my wits.

"Thanks, but I, uh, was just on my way to the Little Girls' Room to freshen up."

"Sounds like a great idea. I need to take the shine off my nose, too. Mind if I join you,...?"

"Cassandra. Cassandra Santee."

"So YOU are Cassandra! I was hoping we would meet someday. I'm Melissa Monet. I have heard SO MUCH about you from my friends. They told me you were breath-taking. Even that doesn't do you justice. You are GORGEOUS! Come on, Girlfriend. I'm not going to share you with ANYONE tonight!"

She took my arm in hers and led me towards the bathrooms. Her strong, confident mien and the tone in her voice advised she was not one to take "no" for an answer. Dazed, I could but follow her lead.

There is a small, dark alcove just off the main hallway leading to the bathrooms. Anyone standing there, in the shadows, cannot be seen by people passing by. Melissa thrust me into the alcove forcefully, slamming my back against the rear wall with a "thump". She pinned my hands flat against the wall by the wrists, ground her body into mine and kissed me ravenously, burying her tongue deeply into my mouth. I felt the swell of her magnificent breasts, the thrust of her erect nipples and the heat of her body as it pressed against mine. I smelled the muskiness of her exotic perfume. I heard the ripple of her leather dress and boots and the husky rasp of her ragged breathing. I could see nothing. The throbbing bulge she felt pressing against her mound was unmistakable.

"My now, what have we HERE? Tsk, tsk, Little Girl; that's NOT very ladylike."

My captor forced both of my hands behind my back, then pinned them against the wall by thrusting her body hard against mine. I could have escaped, of course - but why on earth would I want to? She reached down to my hem and slowly, tortuously, unzipped my dress's full-length front zipper to the waist. Then, she deftly freed my raging cock from its pantied prison.

"Mmm, not ladylike at ALL. Whatever am I going to do with THIS?"

In answer to her own question, the beautiful Dominatrix lifted one booted leg and impaled her drenched pussy on my cock in one fluid motion. She thrust against me as if her life depended on it. The pretense of captivity was forgotten for the moment. I freed one hand to support her raised leg, then the other to aid her thrusting attack.

Her scream began as a low, guttural moan deep in her belly, rising in pitch and crescendo until it rang in my ears and jarred me right to my soul. I don't think anyone but us could have heard it above the pounding din of the heavy industrial music, but that was enough. She thrashed against me again and again, like some demon machine gone berserk. I came with her, shooting torrents of jism into her with the force of a firehose. Years of pent-up frustration, of desire denied, came gushing out in those few exquisite seconds of tortured bliss.

We stood there, trembling in the dark. Neither made any attempt to disengage from the other. I flexed my cock at irregular intervals, causing it to swell and extend inside her. Each time, she whimpered and spasmed. The music pounded around us. People walked back and forth, laughing and talking, not six feet away. We were as oblivious to their presence as they were to ours. As ludicrous as it seemed, given the situation, it was the first time in my life I really felt like a man. It was also to be the only time.

I don't know how, but Gwen and the others could tell. Perhaps it was a glazed expression on my face when I walked in on Monday morning. Perhaps I was staring dreamily out into space at my desk. Perhaps it really WAS female intuition. They cornered me at lunch.

"Admit it; you got LAID this weekend, didn't you?"

I blushed, looked at the floor and smiled sheepishly.

"I KNEW it! Who IS she? Where did you meet her? TELL US!"

I told them about meeting Melissa in college, how we parted too soon, and that I hadn't seen her in all that time until Friday night. I graphically described our "zipless fuck" in the crowded dance club, leaving out the details of which club it was and how we were attired. Their jaws dropped and their eyes bugged out as I related the story. "My GAWD," Beth intoned. "I thought that only happened in the movies." "You STUD you," Gwen gushed in mock disbelief. "And to think I was worried you were gay or something."

Melissa called me every night that week. We talked dirty for hours, as new lovers do - or, at least, as I have heard they do. I was amazed at how easily I fell into the role of the sexy slut who has just been 'conquered', considering I had no previous experience. But then, I have my soft, breathy, sexy voice to work with, a voice that has been described as anything but masculine. I was also aided by Melissa's own somewhat-imperfect recollection of that night. She had a napkin, on which had been hastily scribbled:

Cassandra 555-2739 CALL ME!

She also had a hazy vision of a latex-clad, blue-eyed, blonde bombshell and an apparently-unencumbered memory of a magnificent, mind-blowing fuck that had launched her into orbit. She invited me to an intimate dinner for two at her place on Saturday night. She promised candlelight, classical guitar, lobster, champagne, and a reprise of the previous weekend. "Wear something glamorous," she purred. "And sexy."

I pulled out all the stops. I wore a floor-length, black crepe evening gown with spaghetti straps, gathered bodice, and long, long front slit. My slim, stocking-clad legs were revealed in all their glory as I crossed one leg delicately over the other. My dainty feet were shod in spike-heeled, ankle-strap, black kidskin sandals. My makeup was smoldering, yet tasteful. My lips, fingertips and toes were the same shade of blood red, and my golden hair cascaded softly around my shoulder blades. Long crystal chandelier earrings swayed from my earlobes, while a matching multiple-tiered necklace encircled my throat. A wide crystal bracelet adorned my left wrist, while its more diminutive cousin graced my ankle.

Mere words cannot describe the look on Melissa's face when she finally realized who I was. It happened near the end of dinner, after the lobster but before the champagne was completely gone. I had brought Taittinger, my favorite, and we were both a little giddy. Andres Segovia on the stereo had only heightened the mood. Melissa had not been able to tear her eyes away from me all evening.

I had seen it coming; that slightly-puzzled, quizzical expression that declares: "I know you from somewhere. Where was it?" When it hit, it truly was a "Kodak Moment". A chain-association image flashed before her eyes in an instant: from a leather-and-denim-clad college boy to the latex-clad slut she had shamelessly humped in the dance club the week before, to the sleek, sophisticated blonde arrayed before her at that moment.... Her eyes were like saucers. She slipped one delicate hand to her lips.