Pirate's Tail

I am fairly certain my father knew there was more to my being apprenticed to the Dutch munitions broker Fons Hertzog when I arrived in Cape Town from London then learning a merchant's trade. He was being protective of me, I'm sure, the Great War having broken out the previous summer in Europe with the assassination of the archduke.

With the war only enlarging by the day as 1914 turned into 1915, both of my parents, I'm sure, worried about a son just becoming of age to enter service in the military. It seemed natural enough for George Merriman, the deputy governor-general of the British dominion in the Union of South Africa, to bring a young son following his studies under his wing to learn the functions of statecraft. And there was little more important in statecraft in this season of war than learning how to acquire and sell military arms.

It was yet a different matter of life that my father had in mind, though, I believe—knowing, from observing me, of the interests that were dawning in me and, as I observed when I came out to Cape Town myself, being thus inclined himself. This observation had gone a long way to explain how my parents could be so content with my mother in London and my father forever moving around in British administrations across the globe.

No, though I do think my father truly believed I had a lot of useful tradecraft to learn from the Dutch munitions broker Fons Hertzog, I also believe that my father reasoned that I could be enlightened and unburdened of worry and guilt in other ways while under Hertzog's wing. I'm sure that we wanted to guide my initiation so that I would give myself only to men who could advantage me in life.

Hertzog made his interests quite plain from the time I entered his realm—his business and his household. His was a household completely of men. He was neither married nor did he court women. He was a large, florid man of reddish-blond coloring. I was a reddish blond myself, but, of alabaster skin that rarely tanned even in the southern exposure of the tip of Africa. My coloring was not as ruddy as his. He was tall, but heavy set, given to stifling dress in layers of black suiting. To offset the inevitable odor of this, he doused himself heavily in perfumes and often bathed, perhaps several times a day. But I found that he didn't bathe alone, which is likely what made the habit so appealing to him. He was an active man, as muscular as he was rotund. He had a temper and was pugilistic.

He also stood close to a man he favored and touched him while speaking to him, more often than not burdening the man with his spittle. That's how I knew he favored me. He was always smiling indulgently at me while giving instruction in his trade—the trade I was meant to take up, although I was much more interested in this new science of wireless telegraphy and was learning as much about that as about munitions—and he would stand very close to me with his hand on my arm. He spoke affectionately of my father and of how I should honor my father's intentions in apprenticing me to Hertzog.

I understood my father's intentions all too well, I believe, and, in many respects, I was relieved that he had correctly gauged my interests, but I was naïve and frightened and had no idea how to enter such a world, if indeed I wanted to risk the dangers of doing so at all. I also, if I ever was to go with and be covered by a man, would hope to do so with a more arousing man than Hertzog was.

Hertzog must have seen in me my inclinations, however, as he did little to hide his from me. I was assigned a bed chamber between his and the washroom, and he made no attempt to hide himself from me as he went to his bath—always with one of the young house serving men in attendance—and in nearly the same state of undress. Hertzog was a big man in all ways and he seemed to flaunt his gifts. He did not swing low in repose, but he was extremely thick, and, in erection, was sufficiently long to do an uninitiated young man damage, if he hadn't been somewhat tentative at the cocking.

In turning me over to Hertzog, I believe my father wanted me to be fully initiated but by someone who would consider my standing in life and be careful in developing a young man's desires.

I was still an uninitiated young man, even though that accorded me a good bit of frustration. I was a willing young man, just not initiated.

He as good as spoke his intent to me—one day even coming close to me in the corridor of the bed chamber level of his townhouse and running his fingers into my hair, telling me that there was hair out of place, but then telling me how much he liked the burnish blond curls and my other features as well—how well formed I was and how I would be a prize for any woman—or any man so inclined. I managed to move out of his embrace without too much embarrassment, but his fat lips brushed my cheek as I turned away and he laughed.

He called out as I moved down the corridor, "I am a man so inclined."

As if I didn't know already.

Later he expressed interest in my prowess with women—or men—saying I was of the age to have experience, but I confessed that I had no such experience. I also admitted that I was confused about my interests. He offered me money to let him end that confusion and I feigned being confused about that as well. That, of course, didn't work with him.

"How will you know, if you don't try it out?" he asked. "I can help you with that."

"I don't know," I answered. "I'm afraid and confused." I hadn't said no, though, and it was that omission that he had focused on.

"You know your father has apprenticed you to me for a reason," he said. This I could not argue with.

One night at the end of an arduous work week, he told me that he had earned a trip to a tavern and that so had I. He took me on foot deep into the dock area of Cape Town. He was a merchant dealing in other goods than military arms and had a small fleet of freighter schooners—most three- or four-masters—at his command. So, the docks of the city were no stranger to him.

Immediately upon entering, I discerned that the tavern he took me to was one frequently almost entirely of Indians, that South Asian caste providing the backbone of seaman and dock laborers in the colony at the moment, black natives not being trusted to learn skilled labor. The tavern was reached down a cobble stoned alley leading off the docks. The atmosphere was smoky and noisy with the drunken boisterousness of hard-working men at the end of a hard week of work. The smoke in the air was of a sweet, cloying aroma.

Besides Hertzog and me, who were dressed in European style, in tweed suits with waistcoats, me in a billowy white cotton shirt and Hertzog in stiff linen, those in the tavern were in Indian dress of the colony—collarless shirts of many hues over white, black, or gray dhoti's, the Indian dress of loose cotton trousers created out of one long length of material, intricately woven through a man's legs, and finished with a material tail covering the scrotum. That tail, of course, could be quickly undone to allow for convenient urination.

There was strange music coming from strange instruments—most likely from the South Asian continent—and a small, thin dancing girl, swathed in a gauzy sari, twirled on a table in the middle of a crowd of men with their tongues hanging out. Besides the single woman, though, there only were men in the room, and it seemed that the men around us were more interested in each other than in the dancer. It didn't take much for me to understand that Hertzog had brought me to a tavern like this with a purpose in mind, that purpose being to instill desire in me and to melt my fears and inhibitions. I felt fearful and exhilarated in equal proportions. Would this be what would coax me across the barrier? All of the men were muscular and several of them were pleasant of face as well as of body.

The music, noise, heat, and fog in the room picked up in intensity, as did the sway of the dance of the small woman on the table top. She was shedding veils and stirring up interest. Liquor was flowing. I'd had drink before but probably not as much as Hertzog was cajoling me to take on this night. The smoke was sweet-smelling, opium rather than tobacco, as I was to learn. There were opium pipes scattered here and there, in full use. There was one beside us where we stood at the bar, and I let Hertzog introduce me to that. It made my head seem to float above the activity in the room. It was heightening my arousal and lowering any defenses I might have had. Hertzog kissed me on the lips and I just smiled at him. The second kiss included some tongue, and I smiled at that too. He placed a hand on the small of my back and worked in under the hem of the cotton shirt, his hand on my bare back. I smiled at him and didn't draw away.

"Meld yourself to the mood here," he whispered In my ear. "Your father apprenticed you to me to ease you into what you know you desire. Just give yourself to it this evening."

I gave him no answer, but I remained where I was, which was answer enough for him.

Shirts were slowly disappearing around the room, leaving the men in just their dhotis, and some were even down to their loincloths. They were beginning to embrace and fondle each other even more intimately than they were when we arrived—or I was only now beginning to notice that, finding my senses heightened rather than dulled by the liquor and the smoking. The Indian nature of the atmosphere was exotic, enticing. I had heard that the South Asians were more loose in their attitudes and habits than were Europeans, and I could not avoid falling into the sensual mood.

"We mustn't stand out too much," Hertzog said, as he pulled my jacket and waistcoat off, unbuttoned my shirt, and pulled it out from underneath my suspenders. I just smiled a silly smile and let him. He was already down to his trousers and suspenders. He was fat, with a protruding belly, but his hairy chest was also heavily muscled and he had bulging biceps.

He kissed me again and whispered in my ear, "They have rooms for hire in the back."

"Do they?" I asked, but I must have been dopey enough about what he was proposing that he just sighed and called for another round of drinks.

A distinctively large Indian was rising up out of the milling crowd around the table where the dancer was whirling about. His was a handsome brute—not fat, just thick-bodied and heavily muscled. He was down to a loincloth, his thighs big as tree trunks, his torso smooth, with veins standing out because there was no fat to run through. His eyes were black and piercing, and he had a mustache that was so long that the ends of it descended toward his chest.

Hertzog saw that I reacted to seeing the god of a man by involuntarily moving a hand to my crotch.

"Do you fancy him?" Hertzog asked.

"He's magnificent," I said, not really answering the question in my mind—but undoubtedly answering it in Hertzog's mind.

"Would you lie under me if you lay under him first?"

I didn't respond, not really having a response formed in my mind, and then didn't have to do so, because the massive Indian was making a move across the room. The proposal didn't come as a shock—at least the part about being covered by Hertzog—I had long since realized that it was what had been intended for me. The idea of lying under a muscular, sensual Indian, though, was new and intriguing—and set my juices going.

When the Indian giant stood, he grasped the dancer by the waist. The men around him were chanting, egging him on to take some action. The action he took was to unwrap the sari on the dancer, with her raising her arms and gracefully and slowly twirling out of the cloth wrapping. The divesting of the silky material left her naked other than the tinkling gold chains around her neck, arms, belly, and ankles. Her body was laced with henna work in intricate patterns, her black, curly bush was trimmed to a V. Her labia were swollen and rouged. She was as delicate and perfectly formed, albeit painfully thin, as a porcelain doll.

I watched, in fascination, as the big brute laid her on her back on the table, jerked off his loincloth to expose a hard, thick, long staff that took my breath away, and moved between her legs. There was no way, I knew, that he could get that into her, but it did manage to breach her folds to the base of the glans. She didn't seem to think full possession was going to happen, either, and writhed under him. She shrieked, the sound being met by raucous laughter around the table, scratched at him, and beat his chest with her fists as he moved an inch deeper between the labia. Another inch and she suddenly collapsed and surrendered to him. He placed his mouth beside her ear and whispered to her. I saw her visibly relax. Whatever he was whispering obviously was opening her up, as her swollen labia spread wider and more of his shaft sank in her slit. He relentlessly moved deeper inside her as she moaned and panted and the men surrounding them chanted.

"Deeper, deeper, deeper," they chanted, and he complied until he was in to the hint. She had spread and bent her legs in the effort to accommodate his invading shaft. Her tormentor then began to pump her as the chanting of those around him became rhythmic, matching the rhythm of his thrusts.

"Fuck her, fuck her, fuck her."

The small woman was comatose, all resistance abandoned, just lying there, eyes slitted and moaning deeply. But he was fully inside her and she was smiling. She raised her arms to grasp his biceps, which I took as a sign of acceptance. But it was the smile more than anything else that caused me to ache for him.

She began to writhe again under him, putting her hips into motion, going with the taking. She cried out and collapsed in his arms. Not long afterward, he jerked, and, as he pulled out of her, his seed burbled out of her and down her legs.

When he pulled out of her, cheers went up and he sank back down to a chair at the table next to where she lay, being replaced between her legs by another man, who took up fucking her, no doubt her channel now open enough to accommodate all comers. And then another after him. She lay there, in a daze, head turned to the side and saliva dribbling out of her mouth, as man after man saddled up to her and spilt his seed inside her.

"Isn't he a god on earth?" Hertzog asked, leaning into me. He'd had his hand on my back and it had moved lower while I watched the spectacle in fascination. The hand was now gripping my buttocks and Hertzog's other hand felt my crotch. "He has aroused you. That's Captain Rao. He lays men too. I'm sure he would love to cover you. Is that what will lower your barrier to me?—for a man like that to take your virginity first?"

"No, Mr. Hertzog. I don't—"

But he had already pushed off and was wading into the crowd, going to Rao's table, whispering in his ear, and taking his purse out of his pocket.

I saw Rao look at me, grin, and place his hand on Hertzog's purse, pushing it back, unopened, into Hertzog's pocket. Hertzog insisted, and the man relented and took what was offered to him.

And then he was there, still magnificently naked, by me. One of the other men, an older, taller Indian even than Rao, followed him.

I was petrified. I couldn't bring myself to react or defend myself against the man standing there, beside me, naked and towering over me, noticeably regaining his erection, while he prodded and fondled me and took my mouth in a kiss.

"Follow me," he said, and I did, the other tall Indian following me. Hertzog returned to the bar and stood there, watching me be drawn to the back wall of the room and following Rao through a doorway covered by a beaded curtain. We were in a dark corridor with doors on either side. Moans and groans could be heard from the rooms beyond. The room Rao took me to was small. The other man entered as well, and stood by the door with his arms crossed. He was in a white dhoti, his muscular bare chest tattooed. The only piece of furniture was a low table, a sleeping platform, really, which was common of Indian residences in South Africa. The platform was covered with a dirty quilt and a few colorful pillows—a weak stab at a seraglio setting perhaps.

Regardless, the men who came into this room obviously weren't interested in artistic surroundings.

Whispering encouragements to me in smooth English, and me frightened but high on opium and drink and aching with need, Rao tried to fuck me. He didn't ask me if he could, and I would not have been able to fight him off if I'd tried. I just let him manipulate me at will, and when he brushed my thighs open, I left them spread for him to split with his hard cock at will.

He took my virginity away from me, certainly, but he was too large by far for me on that first entry. He seemed surprised at my entreaties that I indeed was a virgin to sex, but he told me he would take care of that and would do so with the least inconvenience he could. I'd seen him cruelly fully possess the dancer on the table, stretching her to the very limit, and I nearly sobbed, knowing he intended to do that to me as well—both fearing it, and in my long-held "getting on with it" frustration, yearning for it.

He had me sitting on the side of the platform, with him crouched over me, my right leg trapped behind him, his left arm laced under my knee and his hand pressed up into my left shoulder blade. He was fondling my chest, thighs, belly, cock, and balls with his right hand, enflaming me and driving me wild, while he covered my face and nipples with kisses. Almost imperceptibly, he had moved his left hand to my buttocks and was pressing my pelvis forward toward the edge of the platform. The fingers of his right hand were playing my anus now. He was using some form of cream to push inside me, his fingers coaxing me to open to him. I knew I'd never open enough for him, and I began to pant and groan.

His body twisted, and I felt the huge bulb of his hard staff at my anus, pressing there. I tried to break away from his embrace, but he wouldn't let me. I cried out as he entered me with great effort. He only managed to get the rim of his glans past my sphincter muscle, though, a penetration that I felt as a surrender to him when the sphincter suddenly had given way.

Not forcing himself any further, he was content with moving his cock there in little pushing and circular motions. I wanted to give way to him. I thought that I'd be able to, but I just wasn't letting him in.

"Relax, open to me, little one," he murmured. "You are beautiful. I won't ruin you as I will want you again."

But it wasn't working.

He was determined to be the first with me, though, to be the first to seed me, so he continued moving there just inside me, until I felt him come, his seed sliding down his unburied cock and my inner thighs.

"In time," He murmured. "There are secrets I can share with you. I believe it's worth you knowing them for me to have you fully. Come to us, Ajit," he said, motioning over the other man to come forward. "You will be able to open him," Rao said.

The man at the door untied his dhoti and then his loincloth and when they hit the floor, I saw what Rao was getting at. His cock was a long one, but it was thin.

I started to object, as the experience thus far had been more taxing and painful than I had imagined it could be, and I moved to shrink away, but Rao held me tight in his embrace, giving way to Ajit, who approached me, grasped, raised, and spread my thighs, and quickly was in farther with his shaft than Rao had reached. He worked me in a series of slides, obtaining a bit deeper purchase and then sliding back. When he then moved in again it was a bit deeper.

All the time Rao was kissing me and giving me reassurances and admonishing me to relax. He whispered instructions for accommodating the cock in my ear as he had done for the dancer, and, making the effort to follow his guidance, I felt my channel walls expanding and giving in to the less thick penetration of the older Indian man, until I heard him mutter, "I am inside far enough. Let's lay him on the platform and I will open him further for you."