Switching Sides

This is chapter one of a six-chapter completed novella that will post by the end of the first week in May, 2021.

“What is it?” I asked as Mario came close to me after we’d been shown to the table on the terrace of the Ciro’ Restaurant overlooking the Marina Piccola—the little harbor—on the Italian island of Capri. Then, confused, I tensed, as he reached around me and pulled the tail of my sports shirt out of the waistband of my khakis. When he’d pulled it out all around, he proceeded to unbutton my shirt and let it flare out from my chest. I didn’t have an undershirt under it. I just stood there, transfixed, with my mouth open, and let him do it.

“There. I’ve been wanting to do that ever since I picked you up at your hotel in Rome,” he said. “You are supposed to be on vacation here, and you are a beautiful man. You should flaunt yourself. Has anyone ever told you you look like . . . like a slightly younger version of that American movie star . . . what’s his name . . . ?”

“Yes, I’ve been told that a time or two,” I said, not wanting to be told for the hundredth time that I looked like my father did when he was twenty years older than I was now.

That aside, I had wanted him to be this close to me ever since I’d seen what a hunk he was in the lobby of the small, yet elegant, hotel Peter had arranged for me in Rome, the Palazzo Manfredi, near the Coliseum. He had arranged the hotel just as he had arranged for Mario Farro to be my personal guide for the four days I was stopping here in transit to the Turkish coast. And yet I also was afraid to have him close to me. For a couple of years now I’d established that I wanted something radically different from my life in Cape May, back in the States, but I had done nothing about changing my lifestyle. I was getting an inkling now that Peter had convinced me to make this stop in Rome and had made all of the arrangements, including Mario, to push me across that line.

“Sorry, this is all new to me,” I muttered, giving him an embarrassed, shy smile as he backed off from me and sat in a chair across from me at the small table. We both sat sideways to the view of the small harbor and rock outcroppings rising from the Mediterranean. The harbor had been the playground, so Mario had told me as we walked up the stone stairs to the restaurant terrace, of the Roman emperors Augustus and Tiberius. The views from the terrace were stunning. If I had been less nervous, I’m sure I would have thoroughly enjoyed the view—and the day trip from Rome that so far had included the ruins of Pompeii in the morning and Naples, across the bay from where we now were on the island of Capri, in the early afternoon.

“I want to show you where there is a spectacular view of the sunset,” Mario had said, and we’d taken the ferry over from Naples to Capri.

Mario wasn’t dressed “uptight” as he had admonished me for doing. He wore worn jeans and sandals, without socks, and his gauzy white cotton shirt hung out of his jeans and was open to show a tanned and perfectly cut torso. A gold chain hung around his neck. That easily could be an Italian gigolo cliché, but it wasn’t so with him. He was a beautiful young man, a good ten years younger than my thirty-seven, and in peak physical condition. He was neither skinny nor muscle bound. He had the look of a male model, including the curly black hair that also lightly patterned his chest, and a ruggedly handsome facial structure, with pale blue eyes and a sensual smile.

He had said more than once that I looked like a movie star. He had that look no less than I did, and we’d got appreciative stares from women and a certain kind of man throughout the day.

His English, although not perfect, was quite good enough. I knew absolutely no Italian. I’d been studying Turkish for the past four months, which didn’t allow time for any other language study. Peter hadn’t had a bit of trouble convincing me that I’d need a guide dedicated totally to me for the stop in Italy. Of course, that hadn’t come up until Peter had convinced me that I needed a break between the States and Turkey and that the break might as well be in Rome.

So, I now thought, Peter had been scheming about this from the beginning. I didn’t know whether to curse him or send him a thank-you telegram. I suppose that depended on just how far Mario’s services went and if I could convince myself to go that far. He’d strongly hinted to me that he was gay when he’d first picked me up at the airport and had been effusive in saying how attractive I was. He hadn’t asked about me, but he seemed to assume I was. I don’t know if Peter had said I was farther down the road to that possibility than I was yet convinced I was. I dreamt about possibilities once I’d relocated to Turkey. I don’t know what I would have thought if something was planned to happen before then.

“And, so, what do you think?” Mario asked after our drinks and a compartmented bowl with nuts, chips, and Greek olives had been plunked down on the table and the waitress had gone off to contend with a large party at the other end of the terrace. We were very much alone where we sat, watching the sun sink toward the horizon over the Mediterranean behind an outcropping of rocks rising out of the sea beyond the mouth of the ancient harbor. He pulled his chair around closer to beside me, “to get a better view of the sunset,” he said rather loudly. I don’t know if that was for my benefit or to be heard by the members of the group at the other end of the dining terrace. In any case the other group’s attention was riveted on a small TV set featuring a soccer match.

“Naples is playing Palermo,” Mario said, in way of an explanation. “That’s why the restaurant isn’t more crowded than it is,” he added.

“Would you rather be watching the football match?” I asked.

“I’d rather be watching you,” he said, with a smile. “So, what do you think of the view from here,” he repeated, looking away from me now as if his other comment at been too forward.

“I think it’s a sight to remember forever,” I answered. “I’m glad you thought to bring me here.”

“Ah, yes, ancient Marina Piccola,” he said in a soft voice. “Quite the place to bring someone you are wooing—a real mood creator. Did you know that legend has this—this very spot—was where Ulysses was tempted by the sirens? And that men only slightly less god-like than Ulysses came here to couple? This is where the Roman emperor Tiberius brought his Sejanus and Emperor Augustus cavorted with his Marcus Agrippa. That isn’t myth. That is recorded.”

“The emperor’s lovers? To couple, you said.”

“Yes, their male lovers—and not just young boys, which was the accepted rage then, but mature men. Coming here to fuck.” He paused there, and when he spoke again, he surprised me by backing away and going to another topic. “So, what are you thinking about today?”

“Today has been great. You are an excellent tour guide. I feel like I’ve really experienced Pompeii and Naples. I’m looking forward to seeing Rome with you.”

“You haven’t really experienced Naples yet, Cliff,” Mario said in a low voice. “We haven’t established yet how extensively you want to make use of my services. This is not a simple sightseeing contract that was made with my service. I am available to you for very extensive personal services, as you wish.”

I turned my eyes away from the sinking sun to look into Mario’s eyes. My arm was resting on the top of the table and he moved a hand to the back of my forearm, touching me lightly there, brushing his fingers across my downy hair, making chills run up my spine. I had “gotten it” some time ago—in Pompeii, when he’d stayed so close to me, excusing it on the uneven cobble-stoned paving of the ancient streets, and I’d let my mind process what Peter was setting up for me here.

“I’ve never been with a man before,” I said.

“I was told that probably was the case—but that you were here because you wanted to make major changes in your life—that you were going to Turkey to be a new man . . . a man’s man. I was told you may need help switching sides in life. You are a very desirable man, Cliff. I have no qualms whatsoever in helping you across that threshold. But it’s up to you to want it—to be open to the change now.”

“Is this really all part of the services my friend engaged for my Italian stopover?”

“Yes. Do you mind? Do you want to avail yourself of all that’s covered in the fees? I assure you, it would be a pleasure, not a chore for me.”

“I don’t know. It’s something to think about. It will be quite late when we get back to Rome tonight. I doubt that we’ll be . . . I just don’t know.”

“We don’t have to go back to Rome tonight,” Mario said. “I have booked a room at the Romeo Hotel in Naples. It’s just across the road from the ferry port there. It’s a very understanding hotel. The name of the hotel should make that clear.” He laughed then, and I chuckled as well—nervously on my part, more easily on his. He certainly wasn’t uncomfortable talking about possibilities. We were talking about him fucking me, and I’d never been with a man before, although I certainly had thought about it. Maybe it was because of this setting—the male-on-male playground of ancient Roman emperors—that made me think seriously about it now. Then again maybe it was because I’d been thinking about doing it for some time now, indeed, it had been at the foundation for me relocating to Turkey.

“It’s completely up to you, of course,” Mario continued, lifting his hand to brush a lock of my hair into place, “but I am available to you if you want to ease the way into why you are making these drastic changes in your life. The ferries will be running all evening. It’s early yet in Italian time. We can be in Naples, in a room at the Romeo, within the hour.” And then, almost as an afterthought, he said, “I can be as gentle or as forceful as you want. We can move from one to the other, as you please. The night is ours alone.”

I turned my face toward the sun that was just now sinking below the horizon, creating a display of red, yellow, and purple streaks across the background of dark blue sky. The sinking of the sun. A glittering transition from one reality to another. The sensual toying of his fingers in the downy hair of my forearm was driving to me to distraction, and to combat that, I concentrated on the shifting scene before me with its changing patterns and intensity of light.

I must have been absorbed in the scene for some time because Mario finally spoke. “I’ve lost you, Cliff. What has taken you away from me?”

“Sorry,” I answered, turning my head to look at him. The waning light from the sea, combined with the soft lights of the lanterns overhead on the framing of the terrace roof, composed of grape vines stretched across latticework, had brought a new beauty to Mario as well. Naples must have scored a goal, because the group across the terrace had erupted into a cheer. Their exuberance jolted me into a decision.

“I can’t help myself,” I responded to his remark on my reverie. “I was organizing what I see out there into a commercial photo shoot.” I didn’t want to baldly say yes to him—that, yes, I wanted him to fuck me. I’d have to make him understand without being blatant about it. I didn’t want to be pathetic in my need for him.

“You are a photographer? That is your profession?” Mario asked.

“That’s what I was before I married and opened a bed and breakfast with my wife—she was the decorator and chef—and I continued working on commercial photography on the side. Some fashion photography, some commercial layouts.” I didn’t want to admit that work wasn’t a necessity for me. I had had the luxury of going for art for art’s sake. My parents had been mainstays in Hollywood. I’d inherited a bundle and could pretty much live life where and as I liked—doing what I wanted. That was the issue that was taking me to Turkey, with this stopover. I wanted to be something radically different from what I had been to now.

“And what do you see out there?” he asked. He was leaning his head toward me, and it would be only a journey of a few inches for us to kiss. If he expected me to initiate that, though, he thought I was a much braver man than I was. “What’s the focus of the photography out there? The rock formations outside the harbor entrance?”

“No,” I said, and smiled. “The rocks and sunset provide an arresting background, but the focus is that small sailing boat coming into the harbor and the young man hiking the sail to pull the boat into the safety of the port. The young man and the boat, working together to one end they both need.”

“Ah, yes, I see him now. He’s a beautiful young man. I can see why a discerning eye would focus on him in this setting. Do you find him sexy . . . sensual?”

“Yes,” I answered honestly. “I see both the young man and the boat as sexy—the two of them moving together, working together toward a fulfillment. I get the sensation of opening to them as they move into the cove.”

“Spreading your legs for them? Letting them penetrate—move inside you?”

“Yes,” I answered, only now thinking of it that way, while realizing it had been in my mind that way. I wanted Mario to understand that I was giving him a yes. We didn’t speak for a few minutes as we watched the young man, outfitted only in a skimpy bathing suit bring the small sailboat onto the sand below the terrace, pull it up above the tide line, give it a hug that almost screamed what I was trying to say to Mario, and pad up a stone staircase, taking him away from us and into what now had become a mere hint of display of color on the horizon.

“And you see him—and his interaction with the boat—as an attractive subject of a photograph?”

“Yes,” I said, and followed up with a revealing honesty that I had no idea I would admit. “It’s what much of my photography is now. Young men—and their interactions.”

“Nudes?” Mario asked, probing.

“Yes,” I admitted. “I have a subscription service of a select clientele interested in such photos.”

“You’ve complimented me. Would you desire to photograph me nude?”

“Yes,” I said, in a breathy voice.

“Alone, or with another man?”

“Both.”

“That could be arranged,” he whispered and then leaned farther into me and took my lips with his. He tasted of the rich and heady Tuscan Cabernet Franc he’d ordered for us. His kiss was light at first, then a few brief seconds of promised fire, his tongue pressing between my lips, before receding again into a lingering brushing of lips. I gave him no resistance. I was hard, wanting him. But he pulled away from me and we both turned our eyes to the dying sunset.

It was Mario who broke the silence. “Cliff? What do you want from me? I am yours to command; you can have whatever you prefer. I’m told you will probably be a top, but we can explore that. I am versatile; I can help guide you to be whatever you want to be. It’s already been paid for. The hotel has been booked.”

He had understood my “yes.” Still I was hesitant. “I don’t know.”

“Is it because I’m a prostitute?”

“No, of course . . . well, that may have something to do with it. That you doing it because you’re being paid to do it.”

“Would it help to know that I’ve been paid the same whether we do it or not—and that I want to do it with you?”

“Yes, that helps.”

* * * *

I will be eternally grateful to Mario—and to Peter, who undoubtedly paid a fortune on my behalf—for initiating me as gently but also as fully as he was being paid to do—and did so as if he wanted to do it, that he wasn’t being paid to do it.

He started on the ferry, finding a secluded spot on the upper deck for us, where we could pretend we were watching the departing Isle of Capri and waning light of the sunset and then the approaching waterfront of Naples in its northern curve or, over the south curve of the bay the still-active volcano, Vesuvius. We sat on a wooden-backed bench, with empty benches all around us, huddled close together for all intents and purposes for protection from the wind whipping across the ferry as it steamed to the distant ferry port. In fact, though, we stole kisses when we thought we weren’t being observed and Mario’s hands were busy in under my open sports shirt, along the surface of my khaki slacks, which somehow became unbuckled and unzipped in the enclosed space between our bench and the one in front of us.

There were one or two other sets of couples on the upper deck, but since they were up here to be at least as intimate as we were being, we were accorded enough privacy for kisses and more. I was aware that we weren’t fooling anyone, but it also became clear to me why Peter had suggested this stop in Italy. No one appeared to be outraged that two men were making out on the ferry. Most of them were making out as well and not concerned with passing judgments. Italy seemed to be a paradise that valued sexual expression over gender identification, which caught me by surprise coming from a heavily Catholic country.

I received my first hand job from a man on that ferry, coming embarrassingly quickly and being overwhelmed in the momentous event—certainly for me, if not for Mario. He had coaxed me to do the same for him, but I’d not gone farther than running my hand tentatively through his chest hair a couple of times and, once he took my hand and placed it there, cupping his genitals through the material of his shorts as he was jacking me off, before I came and, in embarrassment, turned from him, folded myself back into my fly, zipped myself up, and pretended to be engrossed in examining the outline of Mount Vesuvius.

“Sorry,” I muttered in embarrassment. “I should have been willing to do for you what you did for me.”

“No matter,” he’d answered smoothly. “I know it’s all knew to you. You will be able to be freer in private.”

In truth, he had put my senses into as much turmoil as the cauldron of any volcano. I’d done it—taken the first step. The first time I’d kissed a man—or let a man kiss me, rather, and hadn’t pulled away from that. And the first time I’d let a man wrap his hand around my cock, me becoming hard under his touch, and stroke me off and made me come for him. I’d never been sure before—whether I really could harden for a man and come for him. Now I knew.

And now I knew I wanted him to do it again—that I wanted to do it for Mario too. And more, maybe more. But he was right about privacy being a need for me to be that intimate—at least for now.

Mario was great with my nervousness and my turning away. He put his arm around me, whispered how everything was fine and we’d go step by step—and that it was natural that I would have come so quickly but still be reluctant about other matters.

I was a basket case before we’d gotten to the Romeo Hotel, and it’s a good thing it was just across a promenade street from the ferry port. And it was even better that the man—thank god it was a man—at the reception desk acted like nothing was more natural than two men checking into one room at the hotel with nothing more than small backpacks. Mario had told me to bring a clean shirt and underwear as we would be going on the water and I might need dry clothes. The reception clerk even smoothly came up with two toiletry kits as if these went to everyone checking in. Mario had told me that the hotel would be no problem—that we were in the middle of the Chiaia gay district of the city—and he had been right. Mario was taking care of everything.

It wasn’t lost on me that the toiletry kits included packets of condoms.

Mario even at just the right moment turned into the submissive, maneuvering me to fuck him first before he, in turn, fucked me, saying I should experience both options before determining my natural nature and that if I preferred top, which he assumed I would, I would enjoy it more by having some idea of what my partner was experiencing.

Throwing our backpacks and new toiletry kits aside on the foot of the bed when we entered the room, we went directly to the bed ourselves. It was a king-sized bed, obviously the most important—and most used—piece of furniture in the room. Mario didn’t give me time to hyperventilate over what we were doing. He quickly had us stretched out together. As we went down he pulled his shirt off his back and then mine as well. I was in his embrace and we were kissing immediately. And he had his hands all over me. He unbuckled and unzipped me again as we were kissing. And he did that for himself as well. He probably knew I would need more build-up to doing that than he wanted to give him in his steamroll to sex that went beyond the kissing and hand job on the ferry.

He stroked me for a while and moved my hand to his cock. The first time I’d done that with a man, but he had me in the moment and in heat and he wasn’t giving me time or space to think about what we were doing. After pulling out of our kiss and running his tongue across my lips to assure himself that I would open my mouth to him if he wanted a deeper kiss, he moved his face down my throat and to my chest, working my nipples to the point of me recognizing that they were an arousal zone for me. I moaned for him and held his head to me with a hand.

He lifted his head and whispered, “I’m going to do everything to you.”

“Yes, yes,” I answered with a groan. Periodically he stopped and asserted that we were moving on to more, and each time I whispered “yes.” This was my opportunity to experience all I’d dreamed about, all I’d seen being done between men across the fence at my B&B in Cape May. A fulfillment of my fantasies. I couldn’t let this go. Mario was young and beautiful and hard bodied. And he was whispering of the pleasures we were going to experience together.

I lost my shoes and khakis and socks and he smoothly disrobed as well. My initial embarrassment and worry about being naked with him was ended by his exclamations of how toned I was for my age and how well endowed I was—that he was pleased that I was hard for him. That he couldn’t wait for me to be inside him.

Then he took me in his mouth—the first time a man had sucked my cock—and I suddenly was busy working hard not to explode as prematurely as I had down in his hand on the ferry.

He took his mouth off my cock, looked up at me, and said, “You say you photograph young men. Do you photograph them servicing your cock?”

“I’ve never had a man sucking me before,” I answered, my voice shaking.

“Your camera is just there,” he said. “Use it.”

I did, and I think having a camera to point down the line of my torso to catch what he was doing with my cock in his mouth helped me control myself. I think otherwise I would have come almost immediately.

He was professional. He could sense when I was tensing and he backed off until I had calmed down. But he didn’t give up on me, and later, when he moved his body around, hovering over mine, and his hard cock was there, the bulb pressing at my lips, I did the natural move and opened to him. He was restrained, giving me just a few inches. He took the camera from me, held it in one hand, while supporting himself over me with the other arm, and it was my turn being photographed sucking cock.

We’d been on the move all day. He tasted salty and tangy. The smooth, spongy texture of his glans contrasted with the rough, hard-as-steel of his shaft as I moved my mouth farther down the sides of his cock, taking more of him inside me. He put the camera to the side to concentrate fully on me, and then he was way ahead of me, taking nearly all of my cock with each down stroke. I pressed my tongue into his piss slit as he had done with mine, and he rewarded me with a deep moan, just as I had done when he had tongued my slit.

I warned him I couldn’t take much more, and he murmured, “That will come in time,” and turned on me, rising up on his knees, planted on either side of my thighs, as he turned me on my back, looking up at his magnificent, hard torso. He picked up the camera and took a photo of my face in deep want. The camera went to our pelvises, capturing his hand wrapped around our two cocks, frotting them.

I moaned again, as he put the camera aside and reached for one of the toiletry kits, which, as I’d already noticed, contained a small bottle of lube and a couple of condom packets along with the usual toothbrush, toothpaste, and disposable shaving supplies.

I trembled as he opened a packet and unrolled a condom on my hard and throbbing cock, applied lube to the shaft and to his ass, and then saddled himself on my pelvis, impaled himself a couple of inches to obtain purchase, palmed my pecs, looked dreamily down into my eyes, and fucked himself on my shaft.

Again, I came embarrassingly quickly and again he assured me that this was natural for the first time and that I’d gain greater control through repetition.

I had fucked my first man.

“Now me. The pain will melt into pleasure, but let me know if it gets too much,” he whispered as he crowned himself with another condom, turned me on my side, with him stretched behind me, and ran an arm under my waist, palming my lower belly and jutting my buttocks back and up. I gulped as I felt his bulb inside my rim. He placed his free hand under my knee and lifted my leg.

I gasped and tried not to cry out as he slowly entered me. It was almost more than I could bear, but bear it I did, and then it wasn’t more than I could take and I was taking him as he slow stroked me. I don’t think he went deep, but it felt like he was fucking me with a telephone pole.

“Memorializing your first time,” I heard him murmur, and I looked around to see that he had the camera again and that it was trained on his cock moving in my ass. I came again before he did, with him giving a small laugh and whisper, “Good, good. Yes, you want to go with men.” And then he tensed and jerked, and it was done. I’d been fucked by my first man.

He rode my cock again after a short break, complimenting me on my fast reload. This time it was freer and he bounced more—and urged me to grab his waist and thrust more, which I did—and enjoyed it thoroughly. I held the camera this time and fired off photos of him riding me. I was finding that including the camera in the sex play helped me manage my arousal.

“In a bit we’ll clean up and go out on the town. You must be starving,” he said. He was still on top of me, me flaccid inside him, and he leaning over and kissing me on the mouth and the throat and the nipples. At that moment what I was starving for was to move him on his back and take control in fucking him. But that was to come.

We ate on the terrace beside the hotel’s pool, not being dressed for its four-star restaurant, and then we walked for a few blocks to the Ghetto Crime Bar, where we ogled and were ogled. We both were propositioned, but Mario said the pickings were better at another bar—a cruising club not far away.

“The pickings?” I asked.

“No reason just to wade. It’s all in tonight. Tonight we buy you a young lay. Tomorrow night we find someone as nice who wants to go to the hotel with you just because he wants you to lay him.”

I hyperventilated, but I didn’t say no or second guess what Mario wanted to do.

The cruising club was the Depot Napoli. There were many young men on offer. I picked a young Greek out and we took him back to the Romeo. He was amenable to being photographed for extra money. After I took some solo nude poses of him, Mario fucked him as I watched, sitting in a chair by the bed and pointing the camera. Then, still gaping open from Mario fucking him missionary style on the bed, the Italian stud gathered him up, still saddled, and carried him—Nick, he’d said—over to me. Mario put him on my cock, facing me, as I sat there, luckily having rolled a rubber on earlier at Mario’s command. Mario took a turn with the camera. Nick rode me, his arms around my neck, his lips on mine for a while, until he jerked his mouth off mine, gave a little cry, and threw his head back. Mario was behind him. I felt Mario’s cock working its way into the Greek’s passage above mine. Mario grabbed Nick’s waist and stroked his ass, rubbing along my stationary shaft inside the passage.

My first night with a man, and already I had done a DP of a man with another man.

We returned to Rome the next day, and my sex education continued to expand and deepen as Mario introduced me to the gay district of Rome near my hotel, the Palazzo Manfredi. Surmising—correctly—that I liked topping the best, Mario didn’t fuck me again, but I fucked him in a variety of positions he introduced me to. Our club crawls and experiences doing the same things each night were as exhausting as they were educational.

When I boarded a plane at the Rome airport, waving good-bye to my accommodating guide, I was tired, drained, and felt like there was electricity coursing through my body. I had been indoctrinated well. I would have to send a thank-you card to Peter, in Cape May, knowing that this was his doing—and at his considerable expense. I also had a couple of full cartridges of photos to pass on to my service subscribers.

But the one thing I didn’t feel was fully satisfied, fulfilled. I was thirty-seven. I didn’t see myself sustaining a cruising lifestyle for any length of time. Indeed, Mario’s program had almost killed me. There was something else that was missing. I couldn’t put my finger on it—something I had expected switching sides would bring to me that I’d seen in the gay community in Cape May—a community that would have welcomed me, I’m sure, if I’d been ready for it, but I wasn’t. Something else I was seeking other than this wanton orgy I’d experienced in Rome.

Still, there was no shyness left for me. There was not much I hadn’t done for the first time—and the second time—or would not understand how to do the next time. There certainly wasn’t more I could do that wasn’t memorialized in film.