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To Die in Madeira

Category: Gay Male
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I closed my lips over Sir Guy’s cock and pushed his foreskin down with them, my tongue going to opening and flicking down into his piss slit as my mouth slowly took more and more of him inside the moist warmth of my mouth cavity. He sighed contentedly and ran his fingers through my hair. He reached up and pulled my cock down to his lips and started returning the compliment.

We were half way through his massage, and I was on my knees and elbows straddled above him on the massage table in the sixty-nine position, careful not to burden his frail, tortured body with the weight of my hard-muscled 190 pounds. He was moaning softly and making feeble attempts to slowly pump his engorging cock up into the warmth of my mouth. I moved my forearms so that I could palm the flaps of his withered buttocks in my hands and both cushion his brittle skin from rubbing against the vinyl of the massage table top and help strengthen his attempts to pump up into me. I was careful not to thrust with my own cock, letting him do whatever he could with it with his teeth and lips. This wasn’t for me; it was for him. I was just here to serve.

We continued in this position until he gave a little jerk and semen dribbled out of his cock at the back of my throat as he gave a little sigh and then settled down.

He thanked me in a faraway voice from some fantasy land or poignant remembrance of his past as I climbed back off the table and carefully turned him on his belly and resumed the regular part of the massage on his backside, ever so gently working what was left of his muscles and exercising his creaking joints.

“The ass, work the ass,” he murmured. “And don’t neglect the inside, please. Fuck me, please.”

“Are you sure, Sir Guy?” I asked. “I fear I’m too big and heavy for you. I don’t want to hurt you.”

“You always say that,” Sir Guy responded. “And you’re always wrong. You’re never too big for me. You’re big, of course. But just right. Indulge me, please.” And then he laughed. “I think my ass canal is the last youthful part of me. Still flexible after all these years. Still able to take the big boys.”

“I don’t know, Sir Guy. I don’t know if it’s wise.” But I had already placed the pillow under his hips, raising his withered flanks, and I was gently massaging his buttocks in circles, ever widening circles that increasingly opened his crease, revealing a puckered hole. I let a thumb strum across the hole and leaned down and blew on it, and Sir Guy gave a little gasp and then a long sigh.

“What’s wise?” Sir Guy asked “You afraid I’ll die on your table? That you’ll fuck me to death?”

“Umm, Something like that, I guess,” I replied. It had taken several months for my massage appointments with Sir Guy to reach this point. He was living in one of England’s most exclusive rest homes, tucked away riverside at Henley-on-Thames. I had signed on as a physical therapist there. I really fancied myself as a writer, but I couldn’t see enough money in that for years to come, and the middle-aged men who picked me up in the men’s bars for my main source of income and who I had gotten into a routine of massaging as foreplay remarked so favorably on the massages I gave—even what went before the massaging of their cocks—that I took a course of study in massage to add some legitimate income to my upkeep.

I had taken to the old folks homes, as the clients were of the gentle sort. But Sir Guy—I had no idea if he was really a knight, only that everyone called him Sir Guy, and I knew he must be loaded to be living where he was—had recognized what I was immediately. And he had slowly cajoled me into helping him be what he was. But I remained skittish of giving him what he always wanted, as he was so fragile and seemed close to a wasting-away death from the moment I met him.

“I’m not afraid of death,” Sir guy continued, as I continued massaging his buttocks in circles and running my thumbs over his opening hole as they passed by. I thumped the hole with the pad of a finger, and it blinked at me and puckered up. Sir Guy groaned a “Yes, like that,” and I pressed a thumb into the opening, which yielded to me and clutched at the invading digit. “And there is a certain kind of death I welcome and that there’s no use living without.”

“Oh, what’s that?” I asked. I extracted the thumb and thumped it against the hole again, rubbed it across the hole three, four times, and then pushed it back in. His rim grabbed my thumb and pulled it in to the knuckle, and he moved his ass in little circles and moaned deeply.

“Le petite mort,” he murmured through his sighs.

“What was that?” I asked.

“Le petite mort, the little death. Did you not read John Rhy’s Wide Sargasso Sea?” He asked in a little gaspy voice. Paraphrasing poets, he presented each ejaculation, each orgasm as the point of a little death. “A death to be welcomed, wouldn’t you say, Keith? And did you not know that the word for ‘orgasm’ and ‘death’ is the same in Olde English? I prefer that form of death. And when I no longer can die in that way, I welcome the death of the other kind; the final death. And you are helping me in maintaining the edge of life in these little deaths, Keith. Never forget that. Never think you are bringing harm to me in our massage sessions.”

“Yes, sir,” I answered. For indeed there seemed nothing else I could answer. I had grown fond of Sir Guy—to the point of becoming detached when I was wedged between the spread thighs of those middle-aged men from the bars and listening to them grunting and groaning as I split them with my thick cock and wondering if Sir Guy would still be there for our next massage session, if he had survived the week. But so far he always had been there.

“Now the ultimate kiss, if you please, Keith, with plenty of tongue. I grow weary but I must finish. I must have my little death again and pull one from you as well.”

I lowered my face to his crease and blew on his hole again, which puckered nicely for me again. I brushed his rim with my lips and he sighed and trembled for me. As I invaded him with my tongue, he gasped and cried out weakly in passion. His hole spread wide. He started to squirm and his knees scrabbled against the surface of the massage table, but I held him firm with my hands on his hips, not wanting him to rub his thin-skinned knees raw.

“Deeper, deeper,” he cried out, and then “Ahh, yes, yes, yes,” as I pushed my tongue far inside him and moved it about. I could feel him opening up more. I feared what came next, but he seemed to be opening enough to take me.

“Now, now,” He cried out. “Fuck me.”

We’d been here before. There was no talking him out of it. I mounted the table and then crouched down over him from behind on the balls of my feet, suspended my pelvis over his hips. He was scrabbling back at my dick with his long, thin, age-mottled fingers, managing only to grab onto my ball sack and squeezing, which brought forth a long, low moan of my own.

I placed the bulb of my cock at his hole and let his rim muscles pull that inside.

Weak as he was, he was able to arch his back and gasp his appreciation of being invaded. I fisted the root of my cock and moved the bulb around in circles just inside his hole, which opened even more. His fingernails were now scrabbling at my thighs, and he was yipping his little “yes, yes, yeses” and begging me to get on with the fuck.

I let my cock sinking in about four inches, and I started a shallow, slow pumping, which I hoped would satisfy him. But, as always, it didn’t. He urged me on.

I got a hand under his belly and fisted his cock, putting a thumb over his piss slit, so I’d know when he came again. He’d never let me stop until he came again.

And then, as slowly and gently as I possibly could, I sank my thick seven-and-a-half inches inside him, being as careful as I could not to put any weight on his body. When I bottomed, he jerked, and I felt the wetness of his ejaculation burbling around my thumb.

“Now you,” he murmured through a gasp and a groan, and he took my balls his fingers and squeezed and pulled on them, as I started a pumping action in as slow and controlled a manner as I could. Again, he insisted on long, deep strokes. I lost control, as I always did, however, much to his delight, and he cried out for me to ride him hard and deep, as I started doing just that, ejaculating strongly up into him in three spoutings just before my leg muscles gave out and I had to roll off of the table and onto the floor.

“Thank you,” he murmured. “I live yet again.”

I returned to gently messaging his muscles and working his joints, which had now become knotted again at the limited, but unusual exercise they had gotten during the fuck.

“It wouldn’t bother me, of course, to die on this table with your cock churning inside me,” Sir guy murmured as I worked his muscles. His eyes were closing, and I could feel his thin body relaxing, and I knew he was close to the restful sleep that concluded all of our sessions and that, alone, justified what we had done.

“But where I would really like to die would be to die in Madeira. Ah, to die in Madeira,” he whispered, nearly gone now. “Would you like to see Madeira, Keith? You know, that lovely island in the Atlantic off Portugal?” he asked in his last waking breath. He was asleep and didn’t hear my “yes.”

* * *

I had assumed it was just the ruminations of an old and wasting-away man, but, much to my surprise, Sir Guy actually did own a villa high on a hill overlooking a yacht harbor in Madeira, just to the west of Funchal. And when he asked me if I would take him there and stay with him and massage and otherwise service him until the end came, I didn’t think very long and hard before saying yes.

I’d grown weary of making a living of fucking middle-aged businessmen sneaking down from London, Sir Guy had offered me more than that and the sporadic physical therapy appointments combined, and I could do my writing in Madeira as well as anywhere else—perhaps better, as new experiences would be all around me. Who wanted to read about pounding between the thighs of middle-aged men in the rooms above a Reading gay bar anyway? In any event, I didn’t think Sir Guy would be long for this world now, and I was fond of him and thought he deserved to go where he wanted to go to die. It wouldn’t be much of a demand on my time.

It turned out to be a bit more demanding of my time and of my hard cock than I had thought it would be. The breezes wafting through Sir Guy’s open-walled villa hovering above the Atlantic restored his stamina considerably. I did think in the first week or two that this was just one of those fake flame-ups of vitality that often happened just before someone died, but it went on for months rather than weeks.

We were isolated up in the villa, just Sir Guy and me, other than the servants, who were not often seen and who spoke little English even when I encountered them. They all seem to glance down and away toward the marble-tiled floors whenever we passed in the hall. They surely knew why I was there and what I was to Sir Guy, but they chose to act as if I wasn’t present at all. I began to feel stifled and trapped, but Sir Guy, sensing that I had become tense, alleviated my fears by giving me a tidy enough sum to return to England on my own any time I wished and to reestablish myself.

I did find more time to write than I had in Reading, but Sir Guy’s sexual demands on me increased. As frail as he was, he always wanted me to take him hard and deep at the finish. Each time we enacted that little death he increasingly sought. And he always managed to maneuver me so that I gave him what he wanted. We normally had two massage and suck and fuck sessions a day on the terrace overlooking the small yacht basin, and after the first couple of nights, he also insisted on taking me into his bed at night and wouldn’t release me until I had side-split him deep until he had achieved that little rejuvenating ejaculation of his and had felt me cream his insides. Then he would sleep the sleep of the dead. But, miraculously, each morning he would be alive—feeble and thin and living the on-the-edge life of translucent skin and bruising wherever I had gripped him harder than I should in the depths of our passionate fucking—but very much alive.

And each morning over breakfast on the terrace, I would suggest that perhaps we should take a day of abstinence, that the rest would do him good, and each morning he would demur and point to the massage table and say, “That . . . that and your magnificent hard cock, of course . . . are what keep me alive. When you deny me that, I will surely shrivel and die.”

It took no more than that to hold me there with him, as the weeks turned into months and approached three-quarters of a year. Surely, I thought, it can’t go on longer than this. And then I’d always reproach myself. I didn’t want Sir Guy to die—not really. He was a good conversationalist and had a sharp, quick wit. And he had been very good to me. My cock was for sale. If not him, it would be someone else—at least until I started to grow old as well and dry out and wither and blow away as it seemed Sir Guy would do on any given afternoon.

Still, I felt isolated and trapped, and after six months of waiting for what surely would happen before the next dawn—but that never did—I started to take long walks by myself. And in search of company, I started to walk down to the harbor village at the foot of the cliff. There was a small open-air café there on the harbor wall that I began to frequent. And I was not the only one frequenting it.

One such regular was another Englishman by the name of Reginald. He was perhaps five years older than I was, close to thirty surely. A fine figure of a man, his muscle tone enhanced, I’m sure, because he was a part-time fisherman. I understood that he also was an artist and had come here a few years earlier. He’d just appeared in the village, looking for work, and an old fisherman had taken him on. One of the café’s patrons had whispered between his fingers to me of a probable relationship between the young Englishman and the old fisherman and had given as proof positive the fact that Reginald had inherited the old man’s boat, preferred fishing spot, and two-room flat above the small sundries shop across the cobble-stoned alley from the café.

Some afternoons I could hear the Englishman humming and singing softly to himself in his rooms above my head. One of his rooms was all windows, and I could tell that he was using it as his artist’s studio. And I could tell by his humming that he was in his element when he was painting. I knew exactly how that felt. That’s how I felt about my writing as well.

After I had been coming to the café for a month or more, he took notice of me, and if I was there when he came in from his brief fishing excursion of that day, he would come sit at the café. In time, there was a day when the café tables were all occupied and he asked if he could sit at mine.

We talked briefly of England and were both surprised that we had come from essentially the same area. I was from Reading and he had come down from London to a cottage outside of Caversham Park to paint. And for extra money, he’d worked a stint as an orderly in the same expensive rest home in Henley-on-Thames where I had done my physical therapy.

Then one day, abruptly, while we were drinking glasses of amber ale, he said, “I suppose the locals have told you how I came to have that fishing boat out there and the flat above.”

“Ummm, yes,” I said, “There was something about an old fisherman who had befriended you and who you assisted.”

“They put it that way, did they?” He had a little sort of grin on his face.

“Well, no, not exactly that way,” I answered, a bit nonplused.

“I’m sure they told you that I fucked my way to my small inheritance. Isn’t that the exact way they put it?” The grin held on his face but was a little tighter now.

“Well, ummm, yes, that’s what they said. But, you know . . .”

“They have that right. Exactly right. I’ve been watching you, you know,” he interjected. “Could it be that you fancy me too?”

I paused, wondering where to take this, deciding that honesty was the best route. I hadn’t had any variety in my sex life for months, and as generous as Sir Guy was, he wasn’t exactly fully satisfying for a young, vigorous, highly sexed lad like me.

“Yes, I guess I could say that I fancy you,” I answered.

* * *

We fucked in the sun-drenched studio room looking down onto the canvas umbrella tops of the harbor side café. I gasped when I entered the room. A single, narrow, cot-like bed occupied the center of the room, and facing that, in a great circle all around the bed, were oil paintings. All were of young, well-hung naked men. Some of single men in erotic poses. Others of couples or threesomes in various sexual positions. The paintings were very well done and very arousing, highly erotic.

We stripped and wrestled on the bed for some minutes, both tops, both fighting for control. But fishing was hard, muscle-building work, and Reginald eventually wore me down and got behind me, trapping my arms over my head in a strong arm lock, and working his knees between my thighs. When he had worked his hard cock four inches inside me, I gave up the fight and started working with him. I’d been fucked before, mostly when I was younger and was being introduced to the life by my father’s best friend. But it had been a couple of years since I’d last been taken, and so it took Reginald some effort and considerable groaning and grunting on both of our parts for him to bottom inside me, and then to hold while my panting and heaving subsided. And then he ran a strong arm around under my belly and raised my buttocks to where he could rise to his knees and get firm leverage. That accomplished, he began stroke me hard and fast. His thumb came up over my chin, and I took it inside my mouth and sucked hard on it to keep myself from crying out at the mixed pain and pleasure of his throbbing plumbing deep in my channel.

He came quickly in a flood of semen inside me, giving me the impression that it had been some time since he’d had a man. I thought that this might be so—that he walked a thin edge in this small village, considering how he had come to be one of the village residents himself. I supposed that the villagers kept a close eye on all of their young men, even without having ever said anything to each other about it. He must have been looking for someone such as me to come along for some time. All of his sexual energy must have been projected into these paintings of his. But now, for this moment, all of the sexual strength of him was concentrated on that hard cock working inside my ass canal.

After coming in several jerks, Reginald let me free of his tight hold and rolled me over onto my back, He sank down on the floor at the foot of the bed and pulled me down to him, his hands gripping my thighs. And I felt the warmth of his mouth come down over my cock, and he sucked me expertly to ejaculation, with his tongue fucking my piss slit as deeply as he could penetrate me there.

When I had released my seed, he came back up on his feet and pulled my body back up the bed, turning me on my side, and stretching down along my back, the two of us plastered close together on the narrow bed. He lifted my leg, and I groaned and grunted as he ran his cock back up inside me, the entry this time more of a glide, aided by the cream of his earlier coming inside me.

The urgency and lusting of our first fuck behind us now, Reginald took me again with more care and more deference, asking me what I liked and what I liked better. My cries of passion and the involuntary churning of my hips told him what I liked best. I arched my back and turned my face to him and we kissed, his tongue caressing the insides of my mouth and flicking back toward my tonsils, while he kneaded and pinched at my nipples.

Spent, at least momentarily, his dick softening but still inside me, he asked me what had brought me to Madeira. I told him of Sir Guy and my service to him and that I was only here until Sir Guy passed on.

Reginald suddenly laughed and raised up on an elbow and looked down into my face.

“Why that old fucker. He bamboozled you too?”

“Excuse me?” I answered. Studying his face, looking for clues of what he might be talking about.

“Sir Guy is why I’m here too. He brought me out here five years ago. He said he wanted to die in Madeira. He had sweet talked me to be fucking him in that old geezer’s home of his in Henley. Said he wanted to die in Madeira and would I bring him here to do so? Made it sound like death was imminent. I’ll bet the old fucker will survive us all.”

I started to say something, but Reginald stopped tweaking my nipple and raised a finger to my mouth, silencing me. I sucked the finger and then another two into my mouth. I felt his cock stirring again, rising again inside me. I reached back and palmed one of his bulbous buttocks cheeks and held him close against me.

“Five years ago,” and he laughed again. “Well, we got out here and he came to life again and wanted to be fucked hard three and four times a day. I did that for months, waiting for him to die. But all he’d talk about were these little deaths of his—le petite mort he called it—and how they brought him life. And then I started coming down here and found this guy who appeared to be in a lot better shape than Sir Guy was and who was satisfied with a weekly fuck. One day I just didn’t climb the hill again and I heard that Sir Guy had flown back to England. So, he’s still alive, is he? And still getting away with this trick of his. I guess now you’ll leave him too.”

Reginald was fully hard again now. He plopped his cock out of me, though, and stood up behind my butt beside the narrow bed. I didn’t quite know what he was doing—at least until I looked out at his paintings and saw in one a couple in a position that Reginald was maneuvering me into. My left leg was stretched out flat on the bed, and Reginald grabbed under my hip with his left hand and lifted my pelvis, while his right hand pulled up my right leg and propped it up along his chest. Then he swung his right leg over through my spread legs and to the other side the bed, where he dug in his heel where the mattress met the box springs. As he was swinging, I was crying out and grunting, because this maneuver brought his hard, long cock to my entrance at a side angle, and he thrust inside me and started caressing my channel walls with his cock bulb in places and ways it had never been made love to before.

He was stroking me hard and fast, and I was letting him know that I loved what he was doing to me. But at the same time my mind was processing what he had said.

No, I didn’t think I’d be abandoning Sir Guy any time soon. I was fond of him, and I didn’t begrudge him his little subterfuge in his clutching at whatever life and loving that was left to him. No, as long as I could occasionally break away to be mastered like this by Reginald, I believed I would be happy and content on Madeira—and in Sir Guy’s bed—for some time to come.

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