Tranny Tales Ch. 09: My Dreams

Wherein Lie My Dreams

When I was a student at the Belle Arte Academy in Florence Italy, I first encountered what the locals call Tranvestiti or Madonna della Strada; what today we refer to as Transsexual Prostitutes, sometimes including the rarer Sex-changes. Some of the Transsexuals I'd encounter were obviously men masquerading as women, sometimes sporting an embarrassing 5 o'clock shadow, while others were so well cured that they could easily pass as women, especially in the dark coffee bars where they congregated or under the dim street lamps where they stood in the shadows waiting for their customers or the cars full of boisterous boys who would ridicule them asking them "ti faccia nel cullo" (I want to fuck you in the ass) to which the trannies would shout back "go fuck your Mama in her ass".

Although there is little doubt anal forays took place, most of the trafficked sex or should I say, the sex on the side roads away from traffic, consisted of oral blow jobs or "buccino's." If you wanted normal intercourse, there were plenty female pros to give your pecker a fast workout, in the car with the seat reclined or on a blanket on the ground a few blocks outside the city --or in their homes where you might fuck them on a couch or bed a few feet from where their babies slept peacefully. If it was a busy night the pro would stop first at her refrigerator and squeeze a dab of some medicated lube into her finger, lift her miniskirt and apply it to her vagina, then fit you with a condom and invite you to complete your task. Then offer you a glass of cold water as you left.

I had come to Florence following in the footsteps of my father who was a fine artist. Perhaps you've heard of him. Mordecai DelAmora. He was a young artist of great merit, in fact one of his small futuristic oil paintings still hangs in the Galleria Nazionale d'Arte Moderna (National Museum of Art) in Rome, but other than that he is only a small footnote to the artistic community of war torn Italy.

Papa (my father) was summoned to Il Duci (Mussolini), weeks before the Partisan revolt that ended with Mussolini and his mistress hung upside from a lamppost in the city square. At that time, Papa was working on preparatory sketches for a large mural to decorate the House of Parliament in Rome. When the members of the Partisan revolt broke into Mussolini's study they confiscated my father's work and in a trial that lasted all of 16 minutes my father was condemned to be executed as a traitor to the Republic.

My mother was staying in the country with her parents, I was only a child of 7 years but I still recall how they broke into our little apartment on Via Giotto and dragged him out after beating him almost to death with their rifle butts, without even allowing him time to put on his shoes. He grabbed for them with his bloody hands as they dragged him away, after slamming a rifle butt into his groin, those same bloody shoes that I have saved sit today on the mantel under one of his few surviving works, a large self portrait of Papa peering into a mirror and not seeing just his reflection but also seeing into the cloud shrouded future with flying cars and dirigibles. It's a remarkable work, and in the corner of the quadro, under a wooden chair he had painted those same brown shoes streaked with blood. How could he have known?

But one must abandon tragedy, you must leave it behind if you wish to find any pleasure in this brief stay we are permitted on the planet Earth that we call our home. Let me leave my family history behind and recall those happy days years back when I was a starving student living on bread and coffee that due to my inexperience with the ancient coffee pot, always had a large portion of coffee grounds waiting for me as I swallowed the last gulp of espresso from the small ceramic cup.

First off, I must confess, I never had my father's talent at painting. Try as I might I was always a mediocre artist. My beloved professor Ermanno Fingestino, a great teacher and philosopher would pull me aside with his pipe in hand and say, "Julio, you are searching inside you for something you will never find."

I recall coming back into class one afternoon and seeing his abandoned pipe on his desk, that black ruvid textured wooden pipe, that he help perpetually clenched in his mouth. I could see it was lined with yellowed meerschaum and its bowl still filled with the charred tobacco; and as if I were a child, I picked up the pipe and put it in my mouth hoping to draw some inspiration and instead all I got was a strong taste of garlic attached to the stem from what must have come from his lunch at the trattoria across the street, and of course, I felt very stupid.

In retrospect, as I still ponder his advise, I suppose he was right. In fact, I did abandon my art and ended up going into business with my cousin, an engineer who had invented a dry cleaning machine whose control panel I designed in a most artistic manner. Our machine soon became the rage and over the last 30 years we have sold what at last count was over 8,000 machine throughout Europe. The industrial machines sell today for close to 65,000 US Dollars, so yes, I am comfortable now. I live with my family on Via Rophe in a Renaissance styled villa that is divided into two, my cousin and his family occupy the other half. We have peach trees in the garden and apricots in abundance and even a mirabelle tree that fruits every year with luck. Sometimes the birds steal most of the fruit but I don't mind.

Under the villa, we have converted what were originally horse stables, into a large parking garage where I still keep my beloved vintage GTO Ferrari that I call "Silvia," after my first and only true love, back when I was a student at the Belle Arte Academy. Silvia, how often I dream of her at night, how frequently I think of her even during the days, even now, after so many years have passed.

Who was Silvia? Let me tell you first what she looked like. She tall, 178 centimeters (5'8") , long silky hair, black as a raven, cupid lips that parted to show beautiful teeth, one of her lower teeth , third from center was slightly tilted to the left, as if God was saying, "no one can be permitted to be so perfect." Her incisors were long and white, the true sign of youth. She seemed to always wear red, a Raphael red like the color of the blouse of Jesus's Mother, as in the painting Madonna del Prato. A red unlike those you find today in the cheap Hong Kong fabrics that fill our negozi (stores), a red that represented the life force of her struggle and adhered tightly to her breasts.

Oh yes, her breasts were not to be believed, full and round yet rising from her chest wall at a 90 degree angle as if some invisible Angel was holding them up by her thick nipples and silver dollar sized areola. I could never get enough of them. Her waist was slender and yet her ass was well formed with a sort of bubble, but but not extreme and when she squeezed her thighs together, her well shaved pubic area, nude as a grape, seemed to hide the most perfect vagina there, until she turned around and you could see she must have tucked her cock because only the shiny red head peeping out of her alabaster foreskin was visible in the heart shaped upturn the ass makes at its lowest point before returning its upward path.

Yes, she was a Transsexual, but one you could take home to mama and no one would suspect. "One of these days I'm going to up to Sweden and get "mio cazzo" (my cock) mounted on a wooden plaque," she would say, and pointing at her sizable member, "this has got to go and be replaced by the prettiest cunt you ever did see." Of course she said all this in Italian with that telltale distinctive Florentine accent I so adored. The weakening of the "c and g," the "ts" substituted for the "s," the occasional substitution of "te for tu." Those were the same sounds the the great Leonardo, who was very gay, contrary to encyclopedia biographies who for some reason try to maintain a Victorian myth that he was straight, must have intoned to his Florentine lovers as they mounted him and whispered in his ear.

Sometimes Silvia would express herself more slowly, with some hesitation, in her practiced English that I had spent months teaching her. Sometimes she'd voice a fantasy she had about marrying a rich American medical student and going to live in the US, maybe in California where the sun would tan her cheeks to the color of desert sand. That same sand that the strong winter sorocco winds would carry from the Moroccan desert at night and sprinkle on the paving stones of Florence. Of course I would just laugh and say "tu se pazo" (you are crazy) before throwing her on the bed and ravishing her gorgeous body. The last thing I wanted to see was her in the arms of another.

I asked her to pose for a series of pencil sketches that evolved into charcoal and culminated in her image surrounded by heavy swatches of thick oil paint that took months to dry. Fingestino, when he visited my tiny student apartment spent a long time looking at my painting, and I expected him to say, "Now you are showing some talent." But instead he asked, "when can I meet her?" He always had a roving eye.

I still have my masterpiece, a little dusty for wear and tear, hanging from a rusty construction nail that stuck out of the blank grey cement wall of the garage right next to where I park my vintage Ferrari. But Silvia is long gone and not to be found again.

After I'd know Silvia for only a few days, I had fallen deeply in love with her.There was a quality of honesty and courage she possessed that had allowed her to live the life she had chosen or perhaps I should say, the life that fate had chosen for her. She came from a small town in the Tuscan countryside, her mother, disturbed by her femininity, would beat her thinking that beatings would turn her into a heterosexual. When she was 18 years old, while watching a Saturday morning matinee in the small local cinema where they projected mostly old black and white cartoons, and where the children shouted and screamed so loud you could hear nothing else, a boy who she thought was her boyfriend, held her down in the back of the dark upstairs balcony as three of his older friends raped her anally. Although she bled for several days she kept the assault a secret from her mother who would have blamed it on her behavior.

After that she became disinterested in school, began to skip, left home and started running with a group of "ladyboys" who pooled their money to rent a small farm house on the outskirts of the city. At night they would work the streets and back alleys earning what they could, stealing a customer's wallet while his pants were down around his ankles and his wallet within reach, part of the reason they collected the fee before starting the blow job was to know where the wallet was.

I might add that she was not forgiving and she and two of the larger "ladyboys" met up with the old boyfriend who betrayed her and afterwards he was left with the memento of a razor slash across his face that took out his left eye. And yet with me she was always as gentle as a lamb; but I knew never to betray her.

By the time I met her she was 22 years old and she had left the old life behind. A retired Italian Senator and a Count, furnished her with an apartment in exchange for occasional visiting rights, he was 74 years old--otherwise she was free. This was before the advent of viagra so most of his visits were uneventful although he was very generous to her. I met him several times at his request, evidently Sivia spoke to him of all things. He subjected me to a long interrogation to determine if I was suitable for her and then he took us both out to fashionable ristorante. I tried to pay for the meal to show my respect but he refused and threw the my money back at me.

"How would it look to the waiter if I let a young man pay for me." He then took from his finger a rose gold signet ring richly engraved with his family coat of arms, featuring a prancing unicorn, a ring that he said he'd inherited from his father and placed it on my finger. "It fits," he said, "that is good sign." (If you dear reader, could see me as I write this, you would see I am still wearing it to this day, although with the years I no longer cut the youthful figure I once did and I have had it enlarged more than once.)

Having a benefactor made it possible for the former street urchin to returned to her studies. She had enrolled in the University several years before and was making progress slowly but surely. Whereas previously a diploma in classic including Latin had made medical studies unavailable to the lower classes, as a sign of progress this requirement was lifted and the universities became more egalitarian. Thus she was studying medicine and as such we met at a shared Anatomy class that both med students and artists might attend. I had taken the seat next to her's as I was instantly struck by her beauty. She smiled her assent as I bowed to ask her permission.

I recall her saying, as we examined the various bones, "Guardi (look)," this is how we shall finish, stripped of flesh, devoid of passion, just dusty bones in a box." How right she was.

I had no preconceptions about who she was, she was no aristocrat, she was street smart and unpolished. But in compensation there was nothing phony about her, she was bright and so much fun. Within a week I was madly in love even though I hardly knew her. The sun rose and the moon set upon her every whim. I was smitten like an archery target peppered with arrows. There was a magical attraction about her, her beauty, her personality, her intelligence--her honesty and her blatant sexuality. Every time we conversed in school I was forced to hide my erection.

"Would you consider getting married, I blurted out uncontrollably after only a week had passed. She kissed me on my forehead and said, "No - no there is no need to rush. Let's just be happy together. You know of course that I am not a normal woman, that I am a transsexual."

"Yes I know."

"Do you have any problem with that"

"I've never been with someone like you before but I have no problem, none at all. I'm in love with you." And with that she smiled that confident smile of the spider about to capture its prey --and that made me love her all the more, that she wanted me.

Of course same sex marriage was not yet available in Italy, we were years ahead of ourselves, but in Italy, when you get out of the country and into the big cities there is a sophisticated milieu. "Marriages" of same sex couples of various permutations were not unknown, although they were often masked with a cover story unless one was in the artistic circle where such things were open and commonplace. My thought was that we might lived together and refer to each other as husband and wife, and no one would argued over which public bathroom we used.

And then came the first night we made love; a night that I will never forget. It was a week we'd dined together every night, and we'd talked about everything, from politics to medicine to tradition, to what life in Italy was all about. We discussed my views on homosexuality, bisexuality and she examined me in detail to see if there was even a hint of homophobia. The only thing we do not agree on was the question of the existence of God. She was an avowed atheist. I, being raised a Catholic, or "brainwashed" as she said, believed she was sent to me as a sign that there was a loving God who had purposefully brought to me someone who was my intellectual equal or perhaps my superior but one who would be my soul mate and as I was to learn that night, a mate of sexual perfection.

We had dined in the late afternoon at a trattoria, several miles outside Florence, where the painted buildings and city streets give way to tall thin Italian pine trees, like the ones in renaissance paintings and then long swathes of green vegetation. A primeval forest with wild plants and exotic porcini mushrooms growing in the shade of oak trees where the fabled tartufi grew lay behind the trattoria where a dirt road offered entrance.

When we had finished eating and Gustave, our waiter, recognizing we were young lovers, and in Italy almost every waiter is gay, asked if we might like to use one of the two available rooms upstairs to "rest" as he so kindly put it, of course the rooms were not for resting unless one was old and and had suffered an infarct at the end of dinner.

I asked Sylvia if that was agreeable and she nodded. "I'll add the room to your bill, take your time, you can pick up your check whenever you are ready," said Gustav.

He led us up the narrow shiny varnished wooden staircase to a lightly colored wooden door, he reached into his jacket pocket and took out a large metal skeleton key on a thin linked chain, inserted it into the heart shaped shield that surrounded the key slot. "Only I have the key, you will not be disturbed, enjoy."

The room smelled of dried flowers and rose petals. There was a grey light entering from the small window, sunset was only a half hour away. I Looked out the window at the rolling hills where the great Tuscan forest, undisturbed for a millennium, began. "Don't turn on the light," Silvia said, "It's quite magical here." She sat on the side of the bed. I sat on the chair next to her and leaned forward to kiss her lips.

"Would you like us to undress," I said, sensing we would finally become lovers. "No, Julio, I want you to take me just like this."

She unbuttoned her blouse and I realized she was not wearing a bra. I kissed the side of her neck, ran my tongue gently into her ear, as she was unbuckling my belt, unbuttoning my trousers. I reached for her firm warm breasts cupping them both in my hands.

"Stand up." she said and as I did my pants fell to the floor. She calmly rolled up her short skirt, pulled down her flowery pantys and reached for my full erection as she leaned backwards, arching her back as she inserted me into her. "Make love to me, amore," she said.

I was so excited that I doubted if I was giving her any pleasure I moved in and out of her slowly at first, then faster-- but from where was I, it was as if she had a vagina, I kept pumping and entering her and she began to tighten as I partially withdrew, as if she did not want me to exit and then she'd release me as I plunged forward into her,

"Harder my love, harder! she moaned, as my thighs slapped against her soft buttockss, as my balls banged against her flesh and just as I was about to cum she grasped my ass in both her hands and whispered, "Ho venuto" (I just came) and those words triggered a flood of my semen that inundated her, wetting my pubic hair as well.

We remained motionless for a long time, only the sound of our rapid breath disturbed the solitude. Finally Silvia broke the trance ,"Oh si, si, si--raggazzo mio (my big boy,) it's time to go home."

My penis was still erect, I carefully withdrew dripping semen onto the bed cover and floor. She leaned back, smoothing her short skirt, she stuffed her panties into her leather pocket book. I'm so wet, I'll dry off on the ride home, with the warm summer wind in your open topped car. I was driving an old Triumph TR-3 on its last legs but it had never left us "a piede" (on foot.)

When we walked down the narrow staircase, I paid the bill and left a generous tip for the service. We walked out to the gravel topped tiny parking lot. It was a warm night. I rolled back the car's canvas top. She seated herself in the passenger seat with her knees held high. I laughed, she really was going to dry herself.

"Well aren't you going to say if you liked it?"

"I'm still in shock, what did we just do, do you have a vagina?"

"Was it good?" She repeated her question.

"It was fantastic, the best love making in this world- I want it to never end. How did you...?"