The Substitute Travel Companion

by Habu

29 Dec 2023 1439 readers Score 9.3 (18 votes) PDF Mobi ePub Txt


I was lying on my back, my rump at the footboard edge of the mattress, my legs spread and raised, me holding them out and trembling, with Fed kneeling between my thighs, his tongue lapping at my hole, and me panting and moaning when my cellphone, lying on the nightstand in the bedroom of our 37th-Street Manhattan Garment District apartment, started buzzing. Fed rose up from me and reached for the phone.

“Leave it,” I said. “If it’s important, they’ll leave a message.”

“I forgot. I may know about the call. You need to take it.”

“OK, shit,” I growled, turning onto my belly and crawling up onto the bed to where I could reach the still-buzzing phone. “Who the fuck is Lorenzo Carbone? . . . oh, right, the Italian shoe manufacturer who I met in Federico’s office this afternoon.”

“Yes, that’s it. Take the call, and, as a favor to me, say ‘yes.’ I’ll explain later, Kirk.”

I took the call.

“Hello, is this Kirk Reynolds? I’m Lorenzo Carbone. We met this afternoon at Federico Amato’s office. He gave me your number and said I could call.”

“Oh, yes, I remember you.” And, indeed, I did—one slick dude. He was pushing fifty, but he was a real hunk—elegantly turned out, handsome as a movie star, tall and trim, graying at the temples, expressive hands, with long, slender fingers and manicured nails. Did any men get their nails manicured anymore? I guess maybe Italian men did—maybe high-end shoe manufacturers from Milan did.

Anyway, the late forties looked very good on him, as did fifty-three on Fed. That I was only twenty-five didn’t need to be relevant in terms of physical attraction. Both of those men were beautiful Italians and I was a submissive. I was trying to be submissive only for Fed, though, which wasn’t easy. I was a high-fashion model on the runway and in clothes commercials. I got propositioned a lot.

“I hope I haven’t caught you at a bad time.” Yes and no, I thought. Bad timing but I was having a good time. Fed had come up on the bed behind me, was encasing my thighs in his arms, with his hands squeezing and separating my butt cheeks. He had gone back to tonguing my asshole, opening me up, preparing me.

“No, not at all,” I answered. I wasn’t about to tell him what he would be interrupting if Fed wasn’t just getting on with it.

“I called because I’m in New York and I can’t live on all business. I thought Federico could lunch with me tomorrow—I have reservations at the Casa Nonna on 38th Street, off 8th Avenue—but he says he’s too busy. I’m staying at the Staypinapple Hotel near there, on 36th. He said you might go to lunch with me. He knows I am asking you and said it was fine. I enjoyed meeting and talking with you briefly. I find you attractive and would like to talk with you more—over lunch tomorrow?”

He was maybe being a little forward, but we were all gay here and he knew that Federico, a retail clothes buyer for major department stores, was my partner. I didn’t think he was really making a pass at me—just staying in form. And Fed apparently didn’t see him as a threat either. He’d obviously offered me up as a substitute for a little social time with the man. I knew the Fed was having a very busy time of it and that he knew I didn’t have any gigs for the next two weeks after tomorrow night—at least that I didn’t have any yet. And I also knew that Fed wanted to land this Italian’s shoe production account and thought he had the inside track because he’d been born in Milan, where Carbone’s primary plant was located.

“Why, yes, I can meet you for lunch,” I answered. I needed to get off the phone fast. Fed’s tongue was putting me in high heat. Fed might be fifty-three but he was a great lover and was big enough to fill and stretch me like no man before him had done.

I clicked off. “OK, how much shepherding does this man need in New York?” I asked as Fed moved up my body, hovering over me.

“I said later. We have business to concentrate on now,” he murmured in my ear. “He’s just passing through New York. His family’s bought a shoe plant out in Michigan and he’ll go out there to look at it. He asked me to go with him, but I, of course, can’t.”

“So, what’s the . . .Oh, shit, Fed. FUCK! You’re so huge!”

“Yes, yes, I am,” he answered, but that was the last thing he said for a while. He was penetrating and stretching me, working his thick shaft inside me from behind and above. He was an athletic man and liked showing off his physical prowess. He went into a push-up stance stretched over me, taking his weight on his hands planted beside my shoulders and on his toes between my spread legs. He was sheathed inside me, covered with a Trojan Magnum, and, elevating my hips a bit so I could get a hand under my belly, stroking myself off, I panted and moaned for what seemed to be forever as he pumped me thick and deep in an ever-quacking rhythm in his push-up stance.

* * * *

Lorenzo Carbone and I arrived at the Casa Nanna restaurant nearly simultaneously the next afternoon. He was as god-like on this day as he’d been in Fed’s office the previous day. His smile was dazzling, his accent was enchanting. I wasn’t the only one enchanted. We were waited on by a young, quite-good-looking blonde woman, and the interaction between Carbone and the waitress gave me pause and put me off guard. He flirted with her and she was so impressed by and drawn to him that she melted. I think that if he’d propositioned her right there, she would have lain down on the table and spread her legs for him.

I thought that Fed had told me the man was gay. But maybe he hadn’t. Maybe I’d just assumed that—maybe because he seemed just too sexy, even for his age, to be wasted on women. It was only after we’d eaten and were having coffee and had had a wonderful chat in comparing the fashion industry in Milan as opposed to New York when I became straightened out about him again. He was at least bisexual, I discovered—because he did proposition me.

“Federico thought you might be free to show me a bit of the city this afternoon,” he said. “I would love to walk it, and I have been instructed by la mamma that I must go to the top of the Empire State building, and as cliché as that is, one does not deny an Italian mother.”

“I suppose I can show you around a bit, but I have a show to do this evening, so it couldn’t be for too long.”

“I don’t like to look around alone—and I particularly don’t like to travel alone. And that’s why I asked you to lunch. Fed can’t go with me, but he suggested that you might—that you had some time off.”

“Oh?” I said, not being able to think of much of anything else to say, as surprised as I was. Fed never did get around to telling me there was a reason to go to lunch with this man that was larger than just going to lunch with this man. But Fed obviously wanted me to say “yes” to whatever this shoe manufacturer was going to ask of me.

“Thinking that Federico could travel with me,” he continued, “I bought two sleeper rooms on the train out to Chicago the day after tomorrow. From there we were going up to a town in Michigan called South Haven, which is on the shore of Lake Michigan, I’ve been told. We were going to spend several days there inspecting a shoe plant my family has bought before flying back to New York. Since Federico can’t go, I was hoping that perhaps you can. It would be refreshing to be traveling with a beautiful young man like you and I hate to travel alone. And the train tickets are not refundable. You’d be my guest for everything, of course.”

His hand had extended to my forearm and he was playing with my downy blond hair there with those long, sensuous fingers of his.

“You just need someone to travel with you?” I asked.

“I’m hoping for more,” he answered. “I have needs.”

I didn’t give that much of a pause. I was hooked. “Yes, I suppose I could—go to Chicago with you,” I answered. “I do seem to have a couple of weeks off before my next photo shoot.” I knew Federico wanted me to say yes. I knew this was a very important account for him.

Carbone had the idea that I was saying yes to so much more. I wasn’t quite there yet, but I didn’t disabuse him of his understanding. “I am happy you are so amenable. Perhaps I am not too old of a man for you to want to be seen traveling with then.”

“No, of course not. You are a very handsome man.” And very sexy, but I knew if I said that, it would be like lighting a firecracker and I wasn’t totally sure yet that he wanted to fuck me. He hadn’t been explicit yet and he was Italian. I had to allow for some language differences.

But he did want to fuck me.

“That’s wonderful. I find you to be a very sexy young man too.” I guess it didn’t matter that I had avoided using the volatile word “sexy.” He had responded as if I had anyway. “As much as I should go to the top of the Empire State Building, I think my time—our time—could be utilized more pleasurably if you came back to my hotel room with me now. I ache to be inside you. I want to make love to you—no, I can see that you are young and that young men now are straightforward with their language. I want to fuck you—repeatedly. I assure you that I am very good at it. You will pant and moan.” He had reached down and was stroking my hip with those sensuous fingers of his. “Such a narrow waist and hips,” he murmured. “I love a young man with a narrow waist and hips—perhaps the tips of my fingers will meet as I hold your hips steady and I enter you strongly and deeply.”

We had been getting there, but this flood of desire and want was too much too fast. “Uh, no, sorry, I don’t think that’s possible,” I blustered. “Federico and I are partners. I don’t really . . . and I just remembered that I have to go for fittings this afternoon for what I’m to wear in the fashion show tonight.” I had stood up from the table. “But really . . .”

He looked more amused than embarrassed. “I’m sorry. Have I been too forward too fast? Federico told me you were an exceptional lay. He is older than I am. You take his cock, so I am sure you can take mine. And I am Italian. Federico must have told you how open we Italians can be with our desires. And you are highly desirable.”

He did, did he? He told you I was a great lay? I was close to hyperventilating. Maybe I shouldn’t be as sensitive to partnering with Federico. “No, no, it’s OK. You are a beautiful man. If I wasn’t trying it with Fed . . . I really do have to go do those fittings, though.”

“Perhaps tonight then, after your fashion show. I will take you to dinner and then you will writhe with pleasure under me.”

“No, sorry. I will be home with Federico this evening.”

“Writhing under Federico? You think he can fuck you as well as I could?”

“It’s . . . we are partnered.”

“I hope this doesn’t mean you won’t travel to Chicago and Michigan with me. I can try to be good—as tempting as you are. I really do hate traveling alone and I haven’t done much of it in America. I really do need a travel companion to help smooth the way.”

“No, no, that’s fine. I’ll travel with you,” I said. I couldn’t drop my loyalty to Federico and he needed this account. He probably didn’t even say anything to Carbone about me being a good lay.

“But I do have to go now. Thanks for the lunch. Telephone me about the when and where of getting the train to Chicago.”

And, with that, I fled the restaurant. I paused outside of the restaurant and took another look at Carbone through the front window. He was, in fact, a very, very sexy and charismatic man. I laughed, though. He was flirting with the waitress again, and I had visions of her taking her apron off and going straight to his hotel room with him and being the great lay for him that I wasn’t able to be. I had no trouble managing more than a bit of regret that it wouldn’t be me.

* * * *

The travel time from New York’s Penn Station to Chicago’s Union Station on Amtrak’s Lake Shore Limited was a just-shy-of-a-twenty-four-hours overnight ride from nearly 11:00 in the morning to just after 10:00 the next morning. Carbone had ticketed us for two adjacent roomettes, with miniscule baths, each with two key cards that gave each of us full access to each other’s cabins. Each roomette was an approximately eight-by-eight-foot space, one fourth of which was the bath, and into the rest was crammed a sofa that opened up into two bunk beds at night and a chair, with the outer wall being almost completely a glass window. There was a dining car for the first-class passengers, with a skydome lounge above that.

The accommodations were conducive to intimacy and before we reached Chicago, we had attained total intimacy.

Lunch was convivial, with Carbone having much useful information to convey about the fashion industry—both in Italy and the United States. He was an expert in that as in, it seemed, everything else. He couldn’t help from being a sexy man, but through lunch and the afternoon in the skydome lounge, broken up by each of us returning to our individual roomette for a nap, and into dinner, the conversation did not move to the sexual.

It easily could have, as he was dressed to allure—all in black, a black silk long-sleeve shirt over tight black trousers and boots, with the shirt unbuttoned nearly down to the navel, showing an interesting swirl of salt-and-pepper chest hair around his pecs, with a line of hair descending to where the shirt was buttoned. Nobody can dress sexy like an Italian can. When he leaned forward over the table to press home a point with me, the shirt opened enough to show that his left pec was covered in a swirly black tattoo pattern. A gold medallion on a gold chain nestled between his bulging pecs. He had the deep tan one would expect of an active man living in the Mediterranean.

His sexiness certainly was observed by the young man—Sean, his nameplate claimed—who waited on us at lunch and then managed to do so at supper as well. Sean was obviously gay and equally obviously a submissive—and one who would die to go under a mature Italian god like Lorenzo Carbone. He was young—younger than I was, I think—and small, lithe, willowy, and quite openly effeminate. He fawned over Carbone and was reserved with me, who he obviously saw as competition. In turn, Lorenzo surprised me by hardly noticing the young man and his attempts at flirting. It was the second time that a restaurant server—Lorenzo’s reaction to them—had made me second guess the Italian’s preferred sexuality. Here he was being offered a good-looking, if limp-wristed young man on a platter, and he wasn’t showing interest.

Equally, he had backed off on showing sexual interest in me. It was all welcome lecturing on a business I was in my early years of entering into.

After dinner, as it was getting dark, we went back up to the skydome to watch the sun set and the world chug by us. We drank brandy and he had a cigar. He flirted with the young woman who was tending the bar until Sean came up to lean on the bar and to stare worshippingly at Carbone under the guise of also flirting with the bargirl. The young man was determined. When I said I would retire with a book to my own roomette and, without Carbone demurring, moved toward the staircase down to the train’s first level, I couldn’t help but noticing that Sean moved into the seat across from Carbone that I’d vacated and was trying to engage the Italian in conversation.

I was on edge and confused, which, in hindsight, is probably how Carbone wanted me to be. I certainly didn’t want him to be as forward in his propositioning as he had been when he took me to lunch and yet that had aroused me and I didn’t really want him to just drop it—not to keep trying in some fashion. Of course I had no intention of letting him fuck me—or at least I was going to make him work for it—but I was disappointed that he seemed to have given up all forms of the choice.

But then, he hadn’t. He was conditioning me.

I went back to my roomette, stripped down to sleeping shorts, sat in the chair for a while, watching the lights of the countryside slide by, took a book into the lower bunk the porter had converted from the sofa while we were at dinner, and eventually, with a sigh turned out the lights, and let the clackety clack of the train wheels over the rails lull me to a quick sleep.

Later, in the dark, I was half awake while getting the sensation of someone having entered the roomette, wearing a silken robe, and standing momentarily by the bunk, looking down at my prone body. I caught glimpses of a lean, hard body, a swirl of tattooing on his left pec in the flashing of lights in the passing countryside beyond the window as the robe slipped off his body. I was aware he was in magnificent erection. I was aware he had the body of a god.

And then the scene moved ever so quickly. Carbone was on top of me in the bunk. In a drunken stupor, I wrestled with him for a brief time, huffing and puffing, but not resorting to crying out until that was too late. He’d brought restraints and a ball gag and he was too powerful for me. In no time, he had me incapacitated, stretched out on my belly on the bed. My wrists were restrained and hooked on something above my head at the top of the bunk. My legs were strained both at the ankles and around the thighs, holding my legs together, and anything I might have screamed out was muffled by a ball gag in my mouth and the incessant chugging of the train’s engine and the squeal and gnashing of its wheels along the rails.

The struggling wasn’t continuous, there was a sporadic nature about it, my efforts coming in waves of ineffectual struggle and moments of exhausted surrender. This no doubt told the man that I was with him in this—that I was enjoying the game. But at this point, it was no game. He was taking me regardless of what I wanted. He forced me. I struggled against the restraints but then reduced my reaction to exhausted whimpering when he had me bound. I moved against him again when his tongue went between the crease in my buttocks, but I couldn’t manage this for long. The arousal was just too much and I was reduced to low moaning, my clutching with the sphincter muscle relaxing to the rubbing of the tongue. I opened the channel to him; we both knew I had. And then again when he mounted and penetrated me, I struggled against him as he forced himself inside me.

But eventually there seemed no reason to continue attempting a resistance. I didn’t even want to resist him anymore. He was inside me, moving in and out, with something about him causing the muscles of my passage walls to ripple and undulate over the moving hard shaft, and I gave in to him and my sensations went to how exhilarating, arousing, and satisfying this was.

He may have taken my reaction as a game, but I was being forced. And it may have been force against my expressed will, but my giving into it at last and going with him in the motions of the coupling were a genuine surrender to the mastery of him. The kicker was that he may have been justified into thinking I was in to it—that I was roleplaying. I couldn’t deny that half way through the assault, when he was inside me and I was fucked one way or the other, the exoticness of being bound and helpless to the lust of another man swept over me and I wanted it. I wanted him inside me. And I wanted him to want me so much that he just bound and conquered me.

I writhed under him as he leaned over, spread my butt cheeks with his hand, and tongued my ass open. He did not spend much time doing this before he was on top of me, stretched out on my captive body, forcing himself inside me, fucking me. I arched my back, panting hard, doing everything I could to cry out at the penetration, one like I’d never felt before, aware that it was more than that he was just thick and long. Later I was to discover that he had line of gold beads pierced into the underside of his cock and a larger bead in his glans. With these he stretched and punished and worked my passage as no man had done before.

I endured riding under his mastery until I was nearly exhausted, as he gripped my hips between his hands, trying his best to make the tips of his fingers meet over the small of my back, and thrust, thrust, thrust. He kept whispering in my ear to relax and give myself to him, and when he felt that I had surrendered, he pulled out of me, released the restraints on my ankles and thighs, and turned me onto my back. He raised my legs, one after the other, and used the restraints he’d released me from to bind me at my spread ankles at the top opposite corners at the underframe of the upper bunk. He then moved between my spread thighs, grasped and squeezed my buttocks cheeks spread them open to dilate my anus, raised my pelvis to him, mounted and penetrated me again in the missionary position, and resumed fucking me.

Again I bucked against him for a while in useless defense, but he was stroking my cock with one hand as he rode me, and after I’d come, I just collapsed under him and took the churning of his bead-pierced cock. He barebacked me in this first taking, which afforded me the full effect of the piercings. After several moments of fucking me in this position, he surmised—correctly—that any of the fight or opposition that might have been in me was gone. He owned me now, and we both knew it. He unbound my ankles and wrists and freed me of the ball gag. His lips went to mine and my body melded with his as he knelt between my thighs. My knees hugged his hips and my fingernails buried themselves in his biceps, and I locked my pelvis with his, his cock churning deep inside me, and I moved with him.

He owned me and I was committed to the fuck as much as he was. I focused on the unusual and overwhelming sensation of those beads pierced into his cock working the muscles of my passage walls, and, as a result, I gave him a wild and vigorous ride and danced on the clouds I’d never gone to with another man, including Fed. For his part, Lorenzo was what I called a “Boléro” cocksman after the cadence of the famous song by that title. He started slow and picked up speed and intensity as he marched inevitably to his release, leaving me totally wiped out and babbling at the finish. I had come twice while he was forcing me. When he ejaculated at last, I cried out my “Yes, yes! Breed me!” as he did just that with a sharp cry of his own, tensing and jerking and releasing, tensing and jerking and releasing, flooding me deep in my core with his cum.

He left me then, without apology or words of consolation, to drift off into a panting, humming sleep, fully satiated, totally conquered—but, nonetheless, forced.

I woke to the alarm I’d set. We were due into Chicago’s Union Station at 10:00. We had to breakfast and prepare for departure before that. At supper, we had agreed that, since I had an alarm clock and Carbone didn’t, I would come to his roomette at 7:00 to ensure he was up and dressed and we’d go to the dining car together.

I had the key to his roomette and entered to find he wasn’t anywhere close to being ready to go to breakfast. He was stretched out on his lower bunk, naked, and he was holding the effeminate waiter, Sean, into his body, embracing him with one hand stroking off Sean’s cock. The young man’s buttocks were nestled into Carbone’s crotch and the older man’s hips were moving in the rhythm of the deep fuck. Both men looked at me, standing in the doorway of the roomette. Carbone’s expression was one of “so what?” and amusement. Sean’s face showed an expression of victory, as if he was getting something that had been denied me when, of course, he wasn’t.

I turned and left. I went to the dining car and had finished my breakfast when Carbone arrived, looking as elegant, relaxed, and sexy as always. I sat there, across from him, at a table, watching him eat his own breakfast. He used this time to indicate what he’d like to see in Chicago, a city he’d never been to, but that he’d studied the classic architecture of. The conversation was completely devoid of any references to him having bound and forced me in the night or having given the waiter Sean what he so obviously had wanted later in the morning. For my part, I didn’t bring it up either. I was both embarrassed and confused by the realization that, no matter how forced the sex had been, I had found that the sensation of being controlled and forced had sent me higher into the clouds of satiation than any other sex act I had tried.

* * * *

Lorenzo had booked us into the Radisson Blue Aqua Hotel, on North Columbus, an easy—for an athletic type like Lorenzo—walk north to the Navy Pier and south to the large park area on the shore of Lake Michigan that had been the location of the World’s Columbian Exposition of 1893 and that now consisted of a series of parks and cultural museums. The Italian had expressed an interest in Chicago’s world-acclaimed urban architecture and in its art galleries.

The hotel was gay friendly enough that none of the desk clerks raised an eyebrow or hesitated when we were checking into one room, with one king-sized bed. The pretense could be that we were father and son—which still would have raised the question of the one bed—maybe more so than if we were an unrelated couple—but Carbone was a dark, sultry, middle-aged Italian and I was a lithe, blond fashion model. There was no pretending that I wasn’t his boy toy for this visit. I was quite pleased to have it thought that he was my daddy. I suffered a slight gripe to find he’d only booked the one room. He’d told me there would be two. He’d known that by the time we got to Chicago, I would not balk about being in his bed.

I’d been stewing about that all morning as we moved from train station to the hotel. He had taken me by force. I hadn’t said or signaled that he could do so. But by the time the bound assault was over I was accepting—no, welcoming—the fuck. He conditioned me well. Having made clear in New York what he wanted from me, he’d remained aloof, waiting for me to want him—or at least to accept his domination. And I had wanted him. I did want him. Even now, as we were checking in, I couldn’t wait to get to the room with the hope that the first activity he had in mind was to fuck me again in quarters not as confining as the lower bunk in the train roomette had been. I wanted to enjoy more of his exotic moves.

We did fuck when we got to the hotel room. Looking back on it, I thought of this as the lover phase of our short relationship, and it reminded me of having thought of that first time, struggling and then surrendering, on the lower bunk of the train roomette that Lorenzo was a “Boléro” lover, starting slow and sensual and building to a wild ride at release. That afternoon and later that night were slow and sensual in the hotel room. Lorenzo was my attentive lover and I was open and vulnerable to him. He was a master of the exotic and arousing positions, and he took me in several, all of them designed for close embrace, deep penetration, and my full enjoyment of those beads pierced along the underside of his cock and the bigger bead in the cock head, working my channel and coaxing out of me the rippling of the muscles of my passage walls.

As the previous night, he barebacked me, and I accepted that both because the rawness of the contact enhanced the feel of that beaded cock inside me and because he had and dispensed pills that he said would negate any negative effect. He said the Italians were way ahead of the rest of the world in aiding sexual pleasure, and I had no argument to give on that. He assured me he was clean, and had a document he obtained upon leaving Italy that claimed that, and I knew, because we were periodically required to test in the fashion house, that I was clean as well. That beaded cock, though, wiped away the last element of caring for me. No other man—not even Fed—had taken me to such heights of completion as that beaded cock did.

We stayed in Chicago for two days and nights. After fucking upon arrival at the Radisson, Lorenzo wanted to take a walk. He wanted to see the classic skyscrapers of Chicago and the gallery of art first hand, so we walked all over the downtown area. He was like a little boy with what we observed and he proved to be an expert in both architecture and art. He made me enjoy Chicago in depth as much as his beaded cock worked me at my deepest core when he bedded me. We ate dinner at Harry Caray’s Italian Steakhouse on West Kinzie, near the Chicago River. Lorenzo insisted on trying out someplace claiming to be Italian. He declared the food at the restaurant named for a renowned sports caster of the past as authentic enough. Then we went to a few hole-in-the wall, small-venue gay nightclubs, starting with a somewhat sedate jazz bar and moving toward the raunchier and leather, following his “Boléro” pattern, and ending in the hotel room with him on top of me, banging me furiously, and me enjoying every thrust of it.

One of Lorenzo’s fetishes was carried through from the first time he forced me to the last time he beat and whipped me—well, two fetishes. There was always his obsession with how thin my waist and narrow my hips were, and each time we fucked he had a ritual of encasing my hips in his spread hands to hold me steady as he penetrated. This wasn’t much of a fetish, though. The other one was more suggestive of what I should have combined with his “Boléro” pattern to register more concern about where this was going. He always wanted to use restraints with me—at least in binding my wrists together. He always wanted me captive and vulnerable. He always wanted and got off on the illusion of a forced taking.

He always wanted the illusion that it was by unaccepted force—and it was, in the first time and then again in the last.

The second day, we left town. We took the El down to Oak Park, which has the largest collection of Frank Llyod Wright-designed houses simply because that’s where the famous architect got his start and had his first design studio. We spent the full day finding and examining the Wright-designed houses and church in that town. Lorenzo exhibited that he knew quite a bit about Wright and his design era before we walked the town, but we certainly both knew a lot more when we’d left.

Lorenzo was exuberant with the activities of the day, and he let loose in sex—or started to do so—that night. We were wild in bed—or he was, at least. I was bound and gagged, and he took me hard and rough, slapping me around on the face and buttocks and taking me totally. It was a step up from the previous night, but not so much as to warn me of what was to come.

I had asked him at dinner that night—a rare occurrence, as we almost religiously separated the activities for our day from the bed play at night—what he had planned for this trip if Fed had agreed to come with him.

“Fed is a top too,” I said. “I don’t think you would have had the same trip with him rather than me.”

“Federico shares my passion for art and architecture—and for Frank Lloyed Wright, in particular,” Lorenzo said. “We would have enjoyed the same activities by day that I have with you—I just would not have had to be the guide and teacher with Federico that I have been with you. And I’ll have to admit I’ve enjoyed teaching you.”

“But night time. The other element of this trip,” I persisted.

“I’ve enjoyed being your teacher in bed too. And I don’t think I’m flattering myself in thinking you’ve enjoyed it too—and have learned.”

This far I had enjoyed what I’d learned under him in bed, yes. But that was to change. I didn’t know that at this point, however. “You know what I mean. You are both tops. You would not come together in bed as we do.”

“Ah, but in our younger days, Federico and I did come together in bed. But we brought one or more young men into bed with us. We worked well together, Frederico and I did. I did rather look forward to doing this again with him. We would have shared on this trip. Perhaps we’d have brought you with us and we would have taught you what two men can do with another.”

I shuddered at the thought, but I didn’t pursue the point further. He had answered the question. And the two hadn’t been together for twenty years. They would have been young men, just a bit older than I now was when they’d done that. And, more important, I would have been a toddler then. Fed and I hadn’t met then. I wasn’t a sexual being then. He had no obligations to me then. He didn’t, in fact, have any obligations to me now. And my obligation to him had been dimmed when he pressed me to go on this trip. I’m sure he knew what Lorenzo would want to do with me. This shoe supply contract must be that important to him.

I did subsequently dream of how it would be with both Fed and Lorenzo in bed with me, perhaps with both of them inside me at once, and I had to admit that the thought of it made me go hard.

No matter what, he was the masterful lover, and I let him take liberties, trading a bit more pain in the taking for the high-passion pleasure it gave me. I reasoned that it was only that night and only because he had been so exhilarated by being steeped in the work of his revered Frank Lloyd Wright. But it wasn’t that. I have come to realize that it was a progression—that he was testing my boundaries and finding me yielding at each challenge. We were moving toward his true interests—what got him off the best.

* * * *

I lay spread-eagled on the bed, arms raised, wrists restrained at the opposite corners of the headboard, and legs spread, with ankles likewise bound at the corners of the footboard. I had been biting into the rubber ball gag and screaming in muffled tones that didn’t make it beyond the bedroom walls. A bolster was shoved under the small of my back, lifting and tilting my pelvis up. Lorenzo, naked, in erection, and sitting beside me on the bed pulled the dildo out of my ass and raised it so that I could see that it was the mold of a horse’s cock—longer and thicker than that of any man. He had fucked me with it until I had come for him.

As much of a horror at seeing what he had been opening me up with, my eyes went huge and I whimpered through the ball gag as I watched him set the dildo aside, pull a surgical glove on his right hand, slather it and my hole with lotion, and then, leaning over me to catch every nuance of reaction on my face, the hand was lowered from my sight, between my spread thighs, I felt the coldness of the lotioned glove on my inner thighs, and then I was writhing and screaming into the ball gag and digging my teeth into the rubber ball—and took it and took it and took it until I couldn’t take it anymore and relaxed, allowing him to go in up to the wrist, and whimpered and babbled my surrender.

It was the first time I had been fist fucked.

This was our first night in the lakeside house in South Haven, Michigan, that we were being lent while Carbone finished up the paperwork in his family acquiring a small high-fashion shoe manufacturing plant in the town to expand their Stateside business.

Showing not only his administrative talent, but also the depth of his wealth, Lorenzo had mustered up a sleek late-model Jaguar F-Type sports coup rental that was delivered to our hotel in Chicago and could be dropped off at the South Haven Regional Airport whenever he wanted. It was a two-hour drive east and then north on I-94 along the shore of Lake Michigan, during which I was thinking of how rough he’d been with me in sex the previous night and he, no doubt, was thinking of closing out the sale on the shoe factory and whether there were any Michelan-rated restaurants in South Haven. It turned out there weren’t, but Lorenzo found an Italian restaurant, Maria’s on Center Street, that satisfied his palette that evening.

The house we were to stay in in South Haven for as long as it took to close the plant sale was a swanky French chateau-style, four-bedroom, five-bath, brick story and a half, with a mansard roof mansion directly on the lakeshore on North Shore Drive. A four-bay garage, with an apartment above it, jutted out toward the street. A terrace, with an infinity pool, stretched along the back and four shallow, grass-covered terraces descended to a grassy lawn merging into a wide beach. The house was owned by the shoe plant’s owner, who had retreated to Florida for the sale and who was so anxious that the sale go through that he gave his South Haven house over to Carbone until it did.

The house came with a caretaker, a handsome, tall and lithe Jamaican with a rich, dark-brown skin by the name of Fontel Wallace. The man, who lived in the apartment above the garage, padded around, always nearby but never too obtrusive—or so it seemed. I’m sure he knew what was what in my relationship with Lorenzo Carbone, and the afternoon after our first night there, he revealed that he did. My ball gag had popped out while Lorenzo had his fist up my ass channel, and I’m sure I was vocal enough in response to that that Wallace could have heard us out in his apartment. That wasn’t necessary, though, I caught a glimpse of him in the doorway to the bedroom when Lorenzo was pulling his hand out of me and repositioning himself to cover, mount, penetrate, and fuck me.

That he had seen what Carbone was doing—and that I let him do—became clear the next afternoon when Carbone was off doing whatever he had to do on the closing of the plant sale and I had come out to the pool terrace to lie in the sun and continue to recover from being fisted the previous night. I had recovered physically, but I was taking an emotional hit, and not just because of how rough in sex the Italian was becoming with me. Sometime in the night, after he was done with me but before he released me from the restraints, Carbone had gathered up all of my clothes and my suitcase and hidden them somewhere. He was asserting total control over me. I could go nowhere because I was left naked in the house. He’d locked up his own clothes as well.

I was Carbone’s captive now—physically as well as sexually. I didn’t worry about him keeping me forever. He was compartmenting our relationship still, keeping the general daily chatting and sightseeing sharing on a traveling companion level separate from the dominating, increasing rough sex in bed. I was sure that when the trip was over, that he’d return me to New York and pretend that nothing more forceful had happened as long as I didn’t bring it up. What was worrying me, though, was surviving the rough sex to the end of the trip.

What worried me the most was that I might come to crave the rough sex after the exposure to it on this trip was over. I had never before even considered that I would be worked over by a horse cock-shaped and -sized dildo or a man’s fist but now I found myself thinking back on having experienced that with thoughts of how arousing a sexually satiating they had been.

As I stretched out, naked, on a lounge bed on the terrace, thinking these disturbing thoughts, the caretaker, Fontel Wallace, came out to skim the pool. He was wearing only a Speedo and his body, although not bulked up, was perfectly proportioned, hard, well-muscled, and a glowing dark chocolate brown. As he skimmed, his gaze kept going to me. I could hardly hide my nakedness and I felt too intimidated by the situation to get up and go back into the house. If I had, my nakedness would have been in even fuller view, especially the fact that watching Wallace skim the pool with graceful movements by that great, brown body of his was making me stiffen up. I could discern the line of his obviously huge cock in the fabric of his swimsuit, and It wasn’t my imagination that the shaft swelled as he worked and looked at me from time to time.

I was horny for him, and, knowing he’d see it, I ran a hand down my torso and let it rest on my own engorging cock inside the material of my Speedo. I let my fingers pick out and outline my rod inside the material.

He came over and stood next to the lounge bed. “You are with the old Italian, aren’t you?” he said.

“Yes, we’re traveling together,” I answered, almost chuckling that Lorenzo had been called old. But, of course, in relation to the two of us—Fontel, who probably was in his early thirties, and me—Lorenzo was old.

“More than that, I’ve seen,” the black man said. “I see that he fucks you. And that he is cruel when he fucks you. Why do you let him do that?”

“That’s just the way it is,” I said.

“Is it because he pays you? I think he is a rich man. He certainly is an arrogant man. Are you a rent-boy? Is he paying you enough for you to take what you do from him?”

What could I say? Carbone had been supporting me totally during this trip. I was being paid well, taking everything into consideration. “Yes, I guess you could say I am a rent-boy,” I answered, “but I’m here to help a friend of mine get a good business deal with Carbone. That just sort of evolved into this. He hasn’t been as cruel as he was last night before. It hasn’t been like that before.”

“But I think you like it a little cruel,” Fontel said. “I think you were liking it a bit last night.”

There wasn’t much I could say about that either. That I had—after I had opened enough to accommodate his hand—taken some pleasure in the fist fuck was undeniable and had been bothering me all day thus far.

“I would not be as cruel,” Fontel said. “I would be a lover.”

He went back into the house then, but he didn’t stay long. When he came back out, he was holding four fifty-dollar-bills in his hand. He also had moved the waistband of his Speedo under his balls, and the size—both the length and the thickness of his cock, the size far outstripping the proportion of the rest of his body—was projecting out in erection. He was cut. The bulb was an angry purple. The shaft was jet black, blacker than the tone of the rest of his body.

“I don’t know much about rent-boys,” he said. “Is this enough?”

“Yes, Fontel,” I said, “that is enough.” I didn’t want to embarrass either one of us by dwelling on payment more or longer. He cupped my head in his hands and pulled me to him as he jutted his pelvis toward me. I opened my mouth and slid my lips down the sides of his shaft as far as I could take him in without gagging. I gave him head and he stood there, moaning, and rocking back and forth, fucking my throat.

He fucked me first there on the lounge bed, kneeling between my parted and raised thighs, holding my legs spread with his fists on my ankles. He fucked me deep, hovering over me, his face not far above me, drinking in every nuance of my pleasure at having him deep inside me, stretching me, working me hard and, eventually, breeding me, filling me, making me groan and moan—and sigh and purr.

Eventually, he picked me up from the lounge bed, and, showing me how strong he was, carried me in his arms through the house and up to the apartment above the garage, where he fucked me again . . . and again . . . and again.

No, two hundred dollars was not enough for a rent-boy to be fucked that much by a john. Yes, two hundred dollars was more than enough for pleasure of being so totally fucked by Fontel Wallace. He was just the lover I needed at that moment. I’d never been fucked by a black man before. I’d never been fucked by a cock that big—and commanding before.

* * * *

That night Lorenzo beat me while he was fucking me. He’d only tied my wrists together. We’d gone up to the second level of the house for the first time, to a glass-wall room overlooking the lake and found that the owner had installed his own sex playroom up there. There not only was a bed with restraints, but there were other sex torture apparatuses as well. It had turned Lorenzo on. He’d found another dildo the shape and size of a horse’s cock—even larger than what Fontel was swinging, and he was using it on me on the bed in preparation for trying out some of the other equipment.

I was scared and not ready for this escalation. I cried out when, hovering over me, with me on my back on the bed, he was working the horse’s cock inside me. I raised up into a sitting position to counter him, and he slapped me, hard, across the face, first one way and then the other. I fell back on the bed, but I tried rising again and he punched me in the eye. Gasping, I feel back on the bed, collapsing under him—surrendering. He mounted and fucked me hard and deep then. I gave in to him totally, having a flash of “He is forcing me” go through my brain and inexplicably being joined was a flash of pleasure at being used so. Still, though I lay open and vulnerable and giving him all, he slapped me again as he fucked me, and he took my throat in his hands and choked and released, chocked and released, controlling my breathing, my gasping. And somehow he was raising me up to the clouds. It very likely was the loss of oxygen, but I was aroused at new heights, dancing on the clouds.

Fontel appeared in the doorway, no doubt drawn by my cry. His fists were bunched and it appeared that he was ready to pounce on Lorenzo from behind the Italian. I waved him away, though, not wanting this to get any more violent than it was. He disappeared.

Lorenzo brought me to an ejaculation in the missionary position and then he pulled me up from the bed, dragged me over to a X-frame, and strung me up there, facing the frame. He found a hand whip and whipped me—not enough to break skin but enough to redden me up and to make me gasp and groan. And then he mounted me again from the rear, and finished his fuck in a doggy position.

He carried me to his bedroom and embraced me there, cooing to me the rest of the night, satiated in his “Boléro” style, mild-to-wild fuck technique, no doubt believing I had enjoyed the session as much as he did. What was worrying me as I lay there in his embrace, moaning and whimpering—and nursing a black eye—was that I, in fact, had danced on the clouds in passion from his rough fuck.

The next day Fontel came to me in the bedroom, where I was still moaning in bed and after Lorenzo had driven off in the Jaguar.

“He’s going to kill you,” he said. “You have to get out of here.”

“I can’t, I said. He’s hidden my clothes and I don’t have a ticket to get back to New York.”

“I know where your clothes are,” he said. “And I’ll bet you have some money—you have two hundred from me. I’ll give you more, if that’s what you need. I have a car here. I’ll drive you to the airport. You need to get out of here.”

So, that’s what I did—but I’m somewhat embarrassed to admit that I pointed out that if he bought my body again for another two hundred, I’d have enough for a plane ticket back to New York—and that he carried me up to his apartment and after attending to my eye and the welts on my back and buttocks, fucked me to heaven.

When Lorenzo stopped to see Fed in New York on his way back to Italy and found me in Fed’s office, he said nothing about his sexual demands of me on the trip or that I had disappeared. Somehow, I knew he wouldn’t if I didn’t make any accusations—that he compartmentalized his life in that way. I probably wasn’t even someone who was worth his concern—just someone to fuck while he was traveling. He didn’t mean to bring me near death. To my understanding, he just was one of those men who had to be more intense as a sexual relationship developed. Each session needed to be wilder, rougher than the previous one for him to reach sexual satisfaction.

What scared me was that I had reached this understanding because each more intense sexual experience with Lorenzo had heightened my sexual release and satisfaction as well.

I hadn’t said anything to Fed either about the experience. We just picked up life as we had lived it before. Ours was a reasonably open relationship, though, at least in Fed’s understanding that I was highly sexed and sometimes needed younger cock than he could give me. I kept Fontel Wallace’s contact information and we found a way to meet occasionally over the next two decades and to fuck like lovers. He still, to this date, has the biggest, most satisfying cock, I’ve ever taken.

by Habu

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Copyright 2024