Giuliana's Desires Pt. 01

(All names and individuals are fictional)

First of all, let me lay out the landscape. Giuliana Castelluccio is the heiress to an Italian maritime shipping fortune. Her grandfather and father built the Aegis Line from a few rusty transport vessels after World War II to the mammoth oil-carrying and container ships of today, and later launched the very successful Athena cruise line in the 1970s. Their ships circle the world and make lots of money.

Giuliana was the second oldest. Her older sister behaved badly as a teen and young adult, especially with drugs, and when their parents died, their will left her with only enough to comfortably live on. They didn't want to encourage her profligate ways. Giuliana's brother died in a terrible diving accident before reaching the age of 21. That left Giuliana, whom her parents saw as practically a saint. As control of Aegis and Athena passed to the board of directors and outsiders, Giuliana was sitting on an inheritance in the tens of billions of dollars, plus stock and a token seat on the board.

She attended two board meetings, loved the attention she received there, but found them ultimately boring, and never returned. Out of respect, the board continued to leave an empty chair for her.

But as you will see, Giuliana Castelluccio was not quite the perfect angel that her parents and the public thought her to be. She managed to guard her privacy extremely well. So only through my telling my story will you, the reader, better understand her complex, earthy and Quixotic personality.

I met Giuliana because of our love of classic sports cars. Basically, I owned a rare and pristine Bugatti Veyron she felt she had to have. Along with her bodyguard, we took a test drive down the coast from my home in Naples to a villa she owned in Sorrento. In the end, she got more than the car out of the deal.

It's not that I have a pedigree like hers. My parents own a small textile-manufacturing company where I worked for them in the design department. We were a happy family. I was unmarried but had a girlfriend who worked alongside me. We often slept together.

And then Giuliana came along. Of course I'd heard of her, who hadn't? I wasn't awed by her money, but was quite curious about her family and lifestyle.

Giuliana usually gets what she wants, I soon learned. One way or another. She paid me much more than the car was worth, which I didn't mind at all, and then she invited my girlfriend and I to stay with her for a few days in Sorrento. We were quite impressed with her expansive villa. She wasn't very subtle about taking an interest in me. We all lounged around her large pool, and I could see she kept her tanned body in great shape. Under her bikini, her nicely curved hips and boobs drew my gaze. My girlfriend was justifiably uneasy about the treatment I was getting.

I learned later that Giuliana's last boyfriend only lasted six months. She found him disappointing and he apparently preened excessively, but I didn't hear all the details. Giuliana told me later that what attracted her to me was my combination of manliness and gentleness - and my soft looks. She liked my easy-going nature and my ability to make good conversation with just about everyone. And, she said, she liked my skimpy Speedo and what was under it. Along with smooth skin without a lot of body hair.

But, before you think I'm about to walk into a relationship many men only dream about, think again. Maybe you could call it, in a funny way, a Cinderella relationship.

One thing led to another, and I was soon spending a lot more time with Giuliana than my girlfriend. Giuliana soon hired me away from my parents' company in order to begin an art and music festival at another city where she had a home - Portofino. That meant moving away from Naples.

My life was accelerating to Giuliana's speed. My male friends back in Naples speculated - and speculated some more - about this interest she had in me. I began living in her seaside summer villa, she was paying me way more than I was worth, and she bought me the sports car of my dreams: a 1965 Jaguar E-series in nearly new condition. I was in heaven.

There came the evening when she arrived back in Portofino and we had dinner together at her place, served by her staff, to talk about my progress with the festival. With her money behind it, and no spending limits, I was having no trouble making it a success.

Afterwards, we smoked some potent weed, then retired, for the very first time, to her palatial bedroom and had some quite enjoyable sex. For the first time, I was able to see a pensive, quiet side to her - and enjoyed seeing her totally in the nude, including her cute little cunt. She let her blond hair down and was less formal. It was like seeing a new person. I liked her and felt close to her; I trusted her.

"Silvio," she said the next morning in bed, "thank you for a such a wonderful night. Thanks for sharing my bed. You are truly a find for me. I mean, I haven't been out shopping for a man! It's just that I was so lucky to have met you."

"The same for me."

"Forgive me for my forwardness," she said. "It's my nature. ... I'm such a lucky woman to be able to follow my desires without fear. And as for you, I like you so much because you exhibit such a fine balance between your male and female sides - and you don't seem blinded by my money."

"No one ever mentioned male and female sides before ... "

Giuliana brightened. "I think the most attractive and sexy men, whether they're movie stars or not, show both sides. They've got balls, but also can flirt and behave in sensuous ways that remind me of women."

"Interesting; I hadn't thought much about it. But now that you mention it ... "

"Forgive me for being so upfront, but that's the way I am ... So ... after my last boyfriend, I resolved to look for a different type of relationship. And what I'm going to propose may really upset you, or you may see the possibilities; you may be open to trying something quite new."

"Hmmmm."

"Ecco cosa desidero. To be blunt, what I seek and want is a woman companion who still has that wonderful male equipment underneath. Let me explain: When I was in my second year of Catholic college, I had a brief, torrid relationship with another girl. And I've never forgotten it. But somehow, due to my religious upbringing, I felt guilty, too. Maybe that made it even hotter. But now, when I can usually get pretty much what I want - forgive me! - what I often fantasize about is making love with a woman, who's still half a man - does that make any sense?"

"I'm very surprised by your line of thought."

"Look, Silvio, I know your masculine identity is very important to you. And yet, now that money is no longer a concern for you, or it shouldn't be - wouldn't you be intrigued to live the life of a woman for a time? I mean, haven't you ever looked at a beautiful woman, and wished for a moment that you could walk in her shoes and know that men were lusting after you? To be able to wear her sexy lingerie and clothing?"

"Yes, it has happened several times. I'll admit I'm a little jealous of how sexy women can look. But it never went any further than that."

"So your girlfriend never asked you to wear any of her things as part of sex?"

"Only her panties one time when we were joking around. She told me she thought I should wear panties all the time because I looked so cute in them, but I was rather embarrassed and turned her down."

"Silvio. I am bluntly inviting you to become, well, a Silvia, and be my female companion and my lover! Here's what I've thought: Because you have a slim figure and aren't muscular and deep-voiced, and your hands and feet aren't large, and your facial features are rounded and soft - I can bring in some really expert consultants to give you an amazing makeover. Meglio di quanto tu possa immaginare!"

"You're asking me to give up my identity."

She reached over, flicked on a convenient iPad, and showed me some before-and-after videos. I was astounded. Regular guys were turned into truly sexy women that I found very alluring and desirable. They were given just the right curves; were attired in revealing, tight-fitting dresses; and their makeup was sexy and impeccable. I must admit that I was impressed, and despite myself, could see the possibilities.

"Giuliana, it sounds like it would be fun for a one-time, crazy experience, but as a lifestyle, it would be so disruptive, and such a total change, and to tell the truth, I'd feel like a kept man, or woman. What would I tell my family, my friends? And that's all I would do, just be your companion? I can't go along with this."

"Yes, I understand totally. Really do. And no, I wouldn't want you to be my kept Silvia. No concubina. I have it all figured out. I would find you a position in a fashion house. You already have experience in the textile trade. There, you'd find people of all persuasions - gay, straight, bi, even crossdressers. You wouldn't stand out at all ... "

"I'm very flattered that you're interested in me. You make this sound so attractive and natural."

We were still sitting on her bed. I was wearing a thin brief. Giuliana suddenly noticed with a laugh that there was a spot of wetness on it. "Aha, your penis and libido are giving you away, you bad boy!"

"OK, OK, so the possibility does turn me on as little. Just a little, mind you." I laughed a little nervously. "But I don't want to be your lap dog, and I don't want any changes to my body such as breast implants and hormones, and so on."

"Agreed!" she exclaimed. "Giuliana and Silvia, girlfriends. Silvia, with added benefits! Come on, let's go out and celebrate!"

We went to a secluded nightclub where only the richest A+ list people hung out. I went in rather intimidated by all the beautiful, important people, but after we got drunk, we danced up a storm. One thing I noticed: Giuliana didn't introduce me to anyone.

When we returned to her seaside place, she led me into her bedroom again, where a slinky nightgown with spaghetti straps awaited. I slipped into it. She applied lipstick to herself and me, off went the lights and we piled into bed. Soon she was probing my lips with hers, sexy lipstick to lipstick, and then her tongue was engaging mine, and my wet dick soon began to push healthily against the gown. She grasped it through the slick material, and I pushed it further into her hand.

"Silvia! You don't know how happy this makes me! Just wait until you go further down the path ... "

I impulsively interjected: "This is a funny thing to ask, but have you ever wanted to be a man?"

"Oh, dear, don't ruin the moment. No is the answer. I love being a girl. A girl with power, in all sorts of ways, but mostly due to my money. Money is a little bit of an aphrodisiac, don't you think?"

"Well, I suppose, but for me, just your being a powerful woman, with or without money, is a big turn-on."

With that, I began to tongue and suck the nipples of her ample breasts, while she pulled me to her, pulled up my nightgown and played my dick around in her luscious cunt. Then she inserted me into her warm and inviting wetness. Laying on our sides, she put one somewhat muscular leg over mine, enabling me to pump away with increasing abandon. I now felt her breasts against my chest as we kissed again. Her hand migrated down to her clit, and as I bit her earlobe we both came simultaneously.

We lay there, and she whispered huskily, "That was so fine, Silvio. I had to use my imagination a little, there, imagining that you were a woman. But next time I return to Portofino, you will probably have progressed a lot toward becoming my Silvia. Do you look forward to this? Does it excite you?"

I remained in Portofino while she was off on her travels, checking on her investments in real estate and wine. I could see she had a good business sense - she just didn't throw money away recklessly and she was a good judge of people.

In Portofino, I spent half my time organizing the festival, which was to take place in six months, in the fall. The remaining time was at her place, where her house staff was bemused by the female consultants Giuliana brought in to variously clothe me and teach me the womanly arts - to help me pass and look, well, sexy. I was a good, avid student, because every day I spent with these experts, I saw myself looking and acting better and better. Becoming Silvia.

I didn't tell my family or friends what Giuliana and I were up to, relationship-wise, although I recognized that her curious house staff wouldn't keep it a secret forever, and with Giuliana being so high-profile, eventually the gossip magazines would get hold of the story.

My lover returned after a month and a half. I had missed her, but to be honest, sometimes I had gotten so turned on by trying on sexy lingerie and clothing and wigs and jewelry that sometimes I just looked in a mirror and pleasured myself.

I had learned to love wearing hose, and sexy strapped shoes, and a bra. Yes, I did enjoy displaying breasts! I had learned to walk and behave more like a woman.

I was allowing my hair to grow, but because that was so slow, I had had the opportunity to sample different hairstyles by trying on the various wigs I bought. It was nice to have had an unlimited budget for buying whatever I wished. So, in addition to ten wigs, all sitting nicely on their forms, I had fifteen pairs of shoes and five shades of lipstick. I had really gone wild with earrings after getting my ears pierced, having accumulated 50 or so pairs. And bras! Don't even ask.

With the encouragement of the friendly house staff, I had begun to go out solo to restaurants and movies, and even to a bar or two. I had drawn the glances and approaches of many men, but I wasn't about to encourage them. I'll admit I did want to attract their (and women's) attention. But I was saving herself for my mistress.

So when Giuliana returned, finally, after 40 days away, and I picked her up at the airport (yes, she did have a private jet, which she sometimes helped pilot) she was tired but oh, so favorably impressed with the woman who met her (of course I had messaged her photos and videos earlier, so I wasn't a complete surprise).

"Sei una volpe!," she exclaimed. We hugged and kissed, and on the way home, picked up a bottle of champagne to celebrate the transformation.

"Oh Silvia, you don't know how I've been waiting for this moment," she said as we entered her compound, lit up with tiny lights strung across the courtyard. We were holding hands. "You are a fantasy come true, dear. I am so looking forward to mingling with you."

"I've been waiting, too," I offered, giving her a peck on her cheek. "Two girls."

After a nightcap of the celebratory champagne, we didn't waste any time heading for her bedroom. The staff had meticulously and tastefully prepared for her visit, leaving just a tiny candle lit, leaving the room nearly dark. I carefully undressed her, ending with letting her long blond hair (which had been in a bun) fall free over her shoulders and breasts. Last to go was her panties.

Her body looked incredibly svelte and curvaceous in the very dim, flickering light.

Then she unzipped my tight pants and pulled them down, revealing my deep maroon panties (with bulge). We left my bra and wig on, and I carefully removed my earrings. So, there I stood with a woman's face, but with a rather slender boy-body.

She pulled me to her, and whispered sexily in my ear, "I do need a very good fuck, girlfriend."

In bed, she inhaled my perfume, and nuzzled into my hair, which was, of course, a natural-hair wig.

"Silvia, Silvia," she whispered.

"What was the name of your college paramour?" I whispered, hoping to rekindle her past passion.

"Martina."

"What were her breasts like?"

"Oh, they were small." As she spoke, she felt my filled-out bra cups. "I wish you had the real ones, dear. But I can imagine."

"What were her nipples like?"

"Well, I can't say, exactly. Small, too." Her fingers reached under my bra to tease my own nipples.

It was a though a shock passed through me. I was beginning to feel really erotic. Next she reached down to free my cock from my panties.

"Oh, you do get wet so fast, Silvia. You are such an animal. Now, how shall we do this? Come possiamo fare questo?"

She was nuzzling my neck and I knew she was enjoying my perfume and long hair.

She ended up riding me, slowly easing her butt and cunt down on my prong, fully engulfing it. In the candlelight she was quite beautiful. She had turned quiet again, and looked searchingly into my eyes. Her breasts began to quiver a little as she began to slowly pump me. My midsection worked up and down in concert with her movements. "Concert" is just the word to use, because we were creating the most beautiful and rich music. Sometimes she would lean over so her hair was falling onto my face and chest, and other times she sat straight up. With her eyes closed, she looked like a goddamn goddess.

"Giuliana, you bitch, imagine I'm Martina."

Five seconds later, she came mightily. As I did five seconds after that, squirting everything I had, and then some, into her center.

She smiled, withdrew, and lay down alongside me. Her hand found mine and we lay there falling asleep. Giuliana had come home.

The fair was very successful. I was enjoying my Jaguar. We were moving into the cooler time of the year. We spent some time at her skiing chateau in the mountains.

I was now living full time as a woman, and had begun my role at the fashion house in Naples, where I became in charge of the photographers and publicity. This was new territory for me, both as a woman, and in the rarified world of women's fashion. I had never paid a lot of attention to haute couture before, but now I noticed every detail of what women wore, and what worked and what didn't. This knowledge, of course, fed my own personal fashion sense - as to how I should adorn myself to best advantage.

My co-workers, 80 percent of whom were women, were standoffish toward me at first, knowing I got my job because of Giuliana, but gradually became friendlier. I mean, there were lesbians of all persuasions, gay men, straights with babies, and even two other cross-dressing individuals - one male and one female. The male, Ruggero, was naturally effeminate, but still hetero - and known in his female incarnation as Regina.

We used to go out for lunch sometimes. Regina, taller and not quite as feminine looking as me, liked to dress in peasant outfits and sandals, with long, dark-brown hair. I tended toward more businesslike attire, with pencil skirts and form-fitting white shirts, but with overflowing multiple necklaces. I would top that off hoop earrings and my hair in a bun. We enjoyed the attention we created. Regina was actually married with two children, and his wife didn't mind his predilections at all.

We both enjoyed sitting there at our favorite bistro with white wine and olives, cattily commenting on the fashion prowess of various women passing by. And verbally comparing our collections of bras.

Guiliana and I happily continued our relationship, our girl-to-girl sex and friendship, and I never saw any hint of other boyfriends or girlfriends, but I figured that during her lengthy business absences she saw other people.

Spring eventually arrived, and the vineyards began turning green again. Finally, after much pestering on my part, she agreed to take me on her yacht to her southernmost home on the island of Sicily, near Syracuse. After a scenic voyage with splendid feasting (and more girl-on-girl sex!), the big boat pulled into its mooring, and we went ashore. It was my first visit to the historic island, where the pace of life was somewhat slower.

We spent half the time at her home in the countryside and half on the yacht, and that's where the second half of my story will begin.