Giuliana's Desires Pt. 02

Sunbathing on Giuliana's yacht while moored in Syracuse's harbor – quite sexy, indeed. Giuliana had gifted me a tight-fitting, one-piece swim suit, very modern in cut. And what was surprising was that in addition to the artificial breast forms within, it also incorporated the most ingeniously designed hip padding. Other than the yacht crew, which learned early on about my cross-identity, visitors to the boat and boats passing by never suspected that the curvaceous woman was once Silvio.

I could also swim, since my hair (now down to my shoulders) was now long enough to do away with my never-liked wigs. Funny, but in my role, I felt rather liberated. I loved men looking at and desiring me, while I was still attracted to women, and enjoying eyeing them from heels to earrings, with all the curves in between.

And I still really enjoyed dressing and preparing myself, from basic lingerie to makeup and revealing dresses. You could say that, yes, I continued to turn myself on too. Was I as attracted to myself as I was to others? Maybe.

Giuliana had a new raft of friends for me to meet around Sicily. When the meetings were brief, the acquaintances saw me as a woman, introduced as Giuliana's personal assistant. However, when we visited someone's home for lunch or dinner, or stayed overnight, it didn't take them long to detect something offbeat – which aroused their curiosity and sometimes their sense of humor – and they deduced that Giuliana and I were lovers.

At one modest home, where a well-known woman sculptor named Serafina lived by herself, we had a wonderful lunch, and then stayed on until dinner (at 9 p.m. – I was starving!). She worked mostly with natural wood – driftwood she picked up on the beach – with beautiful brass fittings connecting the pieces. She herself seemed to be gender neutral – with short hair and nice earrings, but with loose jeans and a taciturn personality. Very matter of fact, but still friendly enough.

I was attracted to her work, which seemed virile and sinewy. Giuliana was one of her customers, so Serafina valued the friendship. Her work had also appeared in the festival I ran in Portofino.

That night, we were drinking wine and smoking weed, feeling very pleasant toward each other – the three of us. Funny, but I was feeling more attracted to Serafina than Giuliana at that moment. In her own way, Serafina incorporated both male and female attributes, while I suppose I was coming across the same way.

Surprisingly, Giuliana excused herself to go to bed, saying, "Silvia, I know you two still have art to talk about, so don't let me take you away from that."

So there I was, inebriated, with a light breeze wafting my hair about my face, and my thin dress about my thighs. I was wondering how Serafina saw me. I certainly felt quite womanlike and comfortable, though I knew my voice still had male remnants.

Serafina insisted upon showing me, in the warm night air, some sketches she hadn't shown us before, in a studio I hadn't seen yet. Walking there, our hands found each other and I felt such a wonderful combination of closeness and intimacy, and yes, sex.

Her drawings were exceptional and I told her so.

I wanted her to make a move on me. But I realized that she wasn't very forward, and that holding hands was maybe something everyone did on Sicily! So at one point we were face to face, talking, when impulsively I first put my finger on my lipsticked lips, and then moved it to her lips. She looked a little bewildered. I then pushed a strand of her hair aside, smiled, and then kissed her forehead (she was shorter than me).

"Silvia," she said haltingly.

"I like you ... a lot," I said.

"But Giuliana ... ," she whispered.

"Can't you see she gave us permission?"

I kissed her, then, lightly on her soft lips. At first she almost pulled away, then she passively accepted the kiss. And then she returned it, with more urgency.

We went to her bedroom, which was decorated a little like a hippy bedroom in California. She absented herself, and returned in a thin, plain nightgown, through which her small breasts and nipples pushed a little. She had subtly perfumed herself.

I was still fully dressed, a little embarrassed at having to strip and expose my cock. Only the lights from the nearby village illuminated her room now. She helped me undress, down to removing my pantyhose and dress. Considerately, she left my bra and panties on.

"So," she said, "da quanto temp vivi come donna (how long have you been living as a woman)?"

"About a year."

"Did Giuliana meet you in that role?"

"Oh, well, I shouldn't be telling you our secrets."

"Knowing Giuliana, and her penchant for the satisfying her desires, she molded you. ... It's hard to put a label on you. I guess I'd say you're a very nice, sexy man who also makes a very nice, sexy woman."

"Why thank you."

And with that, we lay down. Never having made love with such a mixed-gender woman before, I wanted to see where she would go.

"Do you like sex with men?" I probed.

"I did for a while. But tell the truth, I've been asexual for years now."

"You haven't had coitus for years?"

"No."

"Would you like me to fuck you?"

"Maybe, if we take it nice and slow."

And so, we cuddled and caressed and kissed and moved our bodies together. She wasn't the type to French kiss. And she didn't touch my cock. She just liked to kiss my neck and hold my butt. To be honest, she was too skinny for my taste with not enough fat in the right places.

Eventually, I began to kiss her small nipples, which enlivened her. Then I moved my hand between her thighs, and she opened them for me.

"Silvia, Silvia, I love you," she half-whispered.

This caught me off guard, and I didn't know how to respond. Here we were in the throes of sex and she opened herself up completely.

"I want to make you happy," I honestly admitted.

"You are, so much more than you realize."

With that, I continued to bring my hand up to her cunt, with her little bush of hair there. She took several deep breaths. I halted when my finger was barely within her cleft. There was wetness there, not the abundant wetness of Giuliana, but wetness.

"You're making me wet too, Serafina."

"It's been a long time."

I kissed her neck and ears and nipples again, with my finger remaining. And then I inserted it deeper into her cunt, slowly, and found her inner lips wetter, and then I went north to find her clit. Surprisingly, it was rather large, and swollen. I moved down to suck on it a little.

She laughed half hysterically, and pushed my head away.

"Silvia, it's almost too much! And you were bringing me close. But please, put yourself in me. I want to do it right, if you know what I mean."

With that, I removed my panties, found my prick to be nicely erect after that tender exchange, and obeyed her request to put some offered lube on my member. Then I lay her on her back, and she put her legs over my shoulders (a sexual position new to me), while I gently entered her. Her eyes were closed. Now my attraction to her mounted and I felt so close to her as I slid inside. She seemed to be slightly gasping, and I was so glad I could bring her to this place.

"I am you," I said inexplicably.

"Yes, indeterminate sex to indeterminate sex!" she said, smiling, as various emotions passed through her face.

As my cock became fully engulfed by her vagina, I felt her warmth and juiciness. I thought her little tits were the most erotic thing and her hair and lips too. And looking at my own bra and tits turned me on too.

I wanted like hell to fuck her really hard and fast, but thought I should throttle down a little. I would pull out a little, and rub my dick around her large clit, which is the largest one I'd ever met. And then I'd enter her again. She seemed so happy and pleased when I was fully inside her.

Finally I couldn't hold back any longer, and sped up. Now her eyes opened fully and she seemed either distressed or close to coming. Like something was threatening her.

So I pulled out again, and was touching my dick to her clit again, when something completely overtook her. She seized up, like all her muscles clamped down completely, and then it looked like she would yell, but no sound came out. And then she shook from side to side, and let a big gasp of air out.

This display shocked me for a moment, but it also fed my drive, and I entered her again, fucked furiously for a few seconds, and came mightily.

We were both exhausted, laying there. After some tender words and a promise to do it again sometime, I kissed her goodbye and left.

Giuliana was asleep, or pretending to be, when I entered our room and took a shower. As I guiltily entered our bed wearing bra and panties, she spooned and hugged me. And we were happy once again. She never asked me if Serafina and I made it, and I never brought up the subject.

What was to be a weeklong trip to Sicily went on and on more toward a month. Giuliana could conduct most of her business on the phone or Internet, and only had to fly out once, for two days. One of her vineyards had developed an unusual fungus, so she had to go see for herself. As for my job at the fashion house, I too was able to conduct it remotely, with lots of Skype sessions, and one quick fly-back and return using Giuliana's jet.

After we were on the island for only two weeks, she and I were at a cozy, tiny, out-of-the-way, restaurant enjoying seafood, local wine and marvelous cannoli for dessert. At a table across the restaurant was her loyal bodyguard, the well-muscled Carlos from Spain. I always tried to put him out of my mind as we enjoyed our travels.

Over our petite table, I learned that Giuliana had further desires regarding me.

"Silvia, you've made such amazing progress in becoming a woman. It's been nothing but wonderful since you walked into your role. ... Well, let's not call it a role – but something you were willing to try. It has been OK hasn't it?"

"Oh, yes. To make a really awful pun, my life seems so much more pregnant with possibilities now. My world has opened up in ways I never thought possible. And I confess I enjoy you leading me. I enjoy your sense of feminine power."

"Oh, thank you, really. Now Silvia, I have something further to propose along your path. I think when we first agreed upon things, you said you didn't want to have breast implants. And I honored that. But when we're in bed and I reach for titties and feel only your filled-out bra, I am, well, a bit disappointed."

"I detected that."

"I'd like to encourage you to go that route!"

It's true that as I had grown more into my role, putting breast forms in my bra every day seemed contrived. But on the other hand, having implants put in was crossing over into the land of no return, it seemed. Like, I would be giving up more of the maleness that still resided in me. Still, the idea now seemed sexy to me, and that's what counts, right?

She saw I hadn't rejected the idea out of hand, so she continued: "I have an acquaintance here on the island, Dr. Fallaci, who's a plastic surgeon to the affluent crowd, and whose customers are very happy with him. No, I know what you're thinking! – that he's done me, but no. Just some of my older friends. He also has done breast implants. The nice thing is, you get to pick the size titties you want! I wish I could do that!

"Now, I was talking with him the other day at a party. He was telling me that commonly, surgeons use implants with saline solution or silicone inside. He says those aren't the absolute best, and if you're willing to spend more, a lot more, you can have the very latest, and safest, and most natural-feeling implants."

"I hate operations," I admitted. "Actually, the only time I've been in a hospital was when I broke my wrist as a kid."

But somehow, the idea of having wonderful breasts had already been planted and was growing inside me. Just as long as she wanted to keep my cock!

I finally assented, went to meet the doc, chose my size (halfway between a B and C cup), and he explained the procedure. He reassured me that he had successfully given lifelike breasts to a number of trans people. Recovery and healing would take about a month and a half. We set the date for the initial visit.

Giuliana was overjoyed, and we continued our Sicilian vacation. She drove me all over the island in her convertible, followed of course, by Carlos. She had this habit, which bothered me to no end, of steering with one hand, while the other hand was laid over my dress or pants, over my cock, like it was a security blanket or something.

One night when Giuliana and I were enjoying some wine out on her patio, and the air was pleasantly warm and humid, she invited Carlos, who stayed in a separate apartment elsewhere on the estate, to join us. Despite being built like an American football player, with bald head and thin beard, he was the epitome of politeness. He spoke four languages and was well-read. We talked politics, and cinema, and food.

I was surprised when she went over to him and gave his shoulders a little rub – wasn't it his place to be giving HER a rub? Then she kissed his neck and shoulders, saying, "Why don't you join us for a while tonight, you know, in the bedroom?"

He didn't seem in the least surprised and acted as though it were just another part of his job. As the Americans say, he had an "aw shucks" attitude. However, I was mortified and felt she was betraying me and cuckolding me.

Another part of me was saying, "So that's how the rich behave. They make their own rules."

Like a dog with his tail between his legs, I followed them to the bedroom. There, for the first time ever (with me), Giuliana pulled out a small silver box and we all swallowed little blue pills. I felt I had to trust her; it was like I was her submissive. I was both fearful and curious as to where this was going.

First, she teasingly undressed Carlos, down to his tight underwear, which revealed the shape of his big erect prick underneath. And then Carlos undressed her, with a familiarity that said he'd done it before.

The drug was making everything seem serene, happy, and very sensual. I was soon very attracted to them both, and they soon undressed me, too, down again to my bra and panties, against which my own cock was straining.

She then reached into both of our undies to grasp our dicks, exclaiming, "I love this!"

Carlos merely grunted and closed his eyes, while my body stiffened a little with pleasure. And then Carlos, without any prompting, took some slender ropes that Giuliana proffered and tied her wrists to the bedposts. I sat down in a chair. Carlos stepped out of his brief.

I was seeing a different side of my lover as Carlos proceeded to fuck her hard. She was screaming a little with pleasure. He was pumping her so energetically that her body moved with each thrust. Now he was saying something in Spanish as he pulled out and squirted all over her cunt. He then rubbed his cum all over her genital lips and clit and she came royally, magnificently, and yet profanely.

I felt exhausted just looking at them.

Now came another totally unexpected turn of events. Again, my feeling of being immersed in her power had me following Giuliana's desires to whatever end she had in mind. I had never, ever done bondage before, but she pulled an apparatus out of a closet and lay it on the floor. It consisted of rods and cuffs.

She and Carlos lay it out on the floor and, after she removed my panties, they gently inserted me into it. I was tightly secured in the doggie position with my ankles cuffed and my legs spread, and my wrists cuffed in front. There she stood in front of me, in her beautiful nudeness, admiring her handiwork. I could see her cute cunt, still a little wet from Carlos and her pert, slightly drooping breasts with their nice nipples.

"Silvia, tonight we will truly initiate you into the sorority of women," she said. "I know you've never been fucked, so dear Carlos will give you just a little taste. I'm not even asking your permission; I just know that that's what you desire. I know you're relaxed from the pill, so just open all your senses to him and his maleness and receive him like the woman you're becoming."

With that, she grasped Carlos' prick and lubricated it well, and did the same with my male vagina. When she smoothed the lotion around my sensitive hole, I was stimulated in a way I'd never experienced before. I was, despite all my upbringing and conditioning, hungering for his cock.

He was very considerate and put a finger in first, quite slowly, then pulled it in and out gently, exploring my inside.

"Please, Carlos, give it all to me," I almost begged.

Carlos and Giuliana laughed just a little.

I felt him enter, ever so slowly. A man was inside me! I was so unfamiliar with the sensations of anal penetration. He left himself in there, without pumping. I loved that full sensation.so much that I began deliberately pumping my ass against him. Yes, that was the best way to enjoy it. Back and forth, him inside, me feeling like a woman. At some point he grabbed my hips like men do with women in the doggy style, and he pumped a little in unison with me.

Giuliana came over and began to grasp and stroke my dick, and I soon came all over her carpet. And Carlos pulled out, lay down and masturbated to climax on our bed.

Not only had my man-vagina been fucked, but my mind, too. I had reached a new dimension.

After Carlos left, his services performed, Giuliana and I showered and went to bed in the dark. The effects of the drug still lingered, and I was in a comfortable, happy state. I was definitely feeling more like a Silvia than a Silvio.

"You probably wonder why I brought Carlos in," she whispered. "Well, every few months or so I need a really hard, hard fuck by a manly man. And he's so good at it. I'd swear he could fuck five times a night. And Silvia, I have to explain the bondage gear. Knowing you, and even though the pill had you feeling oh so good, I wanted to put you in the fantasy position of being captured, and made a prisoner, and being fucked without your consent. Like, being penetrated wasn't something you asked for, but was forced upon you."

"I see. You really do want to womanize me, and that's fine, Giuliana. You're right, I needed to experience being fucked. And this first time, the sensations were new to me, but I enjoyed ... being taken."

I added: "I hope you will continue to like having sex with me ... "

"Oh, of course. When we do it, it's like a glass of wine. With him, it's whiskey."

I laughed a little.

"And Silvia, if you wish, from time to time, I myself would love to fuck you."

The breast insertions went well, although there was some residual pain. While my body accommodated itself to them and the cuts and stitches healed, she couldn't play with "my girls," as she loved to call them. I had to wear a special bra to facilitate the healing. Now, suddenly, I was carrying a little weight on my chest. But such wonderful and sexy globes! They were giving me even more confidence in presenting myself as female.

When we returned to the mainland, and to her coastside place at Sorrento, my breasts became almost a natural part of me, and our lovemaking turned even better. She just loved having one hand on a breast (they felt so much like the real thing) and one on my cock. This never failed to turn her on.

One night we were in her bedroom playing in the very dim light, and she was enjoying getting me wet, kissing my neck while spooning me. I was grinding my ass against her cunt.

"I have a surprise for you, dear," she announced.

Somehow I knew what was coming, and became even more wet with anticipation. I was literally dripping as I spied her slipping into a black harness and long black dildo.