by James Lear
Healey stood up and was suddenly businesslike.
“I think, given the circumstances, we can bypass the formalities. I have the information I need right here.” He patted the pile of papers—among which I saw the discharge notice from St. Albans prison. He consulted a list, running his fingers down the entries. “Yup, yup, that’s all fine, mmm-hmm… Oh, well, I guess the only thing we really need to do before we stick you in a uniform is the medical examination.”
I gulped. “Sir?”
“Don’t worry. It won’t take long. And you’re in luck—I’m qualified to do it. And I’ve got nice warm hands.” He grinned.
Perhaps I had misread the situation; so long in a world without moral signposts had led me to some pretty foolish conclusions, and this might just be another one of them. But I could not ignore the fact that Captain Healey had a big, wolfish grin on his face as he took off his jacket and rolled up his sleeves. His forearms were thick and tanned, and much hairier than his head.
“Open your mouth, Edgerton.” He angled my head toward the window and took a good look at my tongue, teeth, and throat. “Mmm-hmmm…a little wider. Thank you. That all looks nice and fresh.”
He ticked something off a list, then started feeling my neck. “Good, good. No swollen glands. Do you feel in good health, generally speaking?”
“Yes, sir.”
“Do you get much exercise?”
Most of my exercise had been on my back or on my knees, but I just said, “Yes.”
“Can you touch your toes?”
I bent over and placed the palms of my hands on the floor.
“Hmmm, good flexibility.” He ticked something else off, and I started to rise. “No, stay there. Let’s just feel your spine while you’re in that position.” He prodded and poked my vertebrae, seemed content, and made another note. “You may now stand up and remove your boots and socks.”
I wondered, briefly, if this was standard army procedure, but one look at Healey’s face told me not to ask any foolish questions. I squatted and untied my bootlaces, bared my feet.
“Sit down.” He gestured to a wooden chair. “Gimme your foot.”
He sat once more on the edge of the desk and grabbed my ankle, pulling me toward him. My heel rested on his hard thigh, and he diligently inspected between each toe.
“You’ve not had a bath in a while, I guess.”
I was ashamed of the state of my feet, and it was true, it was some days since I was last able to wash as thoroughly as I would have liked.
“No matter. Nothing wrong down here.” He inspected the other foot, and seemed satisfied with that one as well, massaging it, flexing the toes with his fingers, turning the ankle, and cradling the heel. I was starting to relax as the familiar feelings reasserted themselves in my body. My good resolutions were slipping away, I could see that—but this was not my fault. I was only taking orders. If this was a necessary step to my redemption through military service, so be it.
“Now, strip.”
I was only taking orders… I pulled off my jacket and shirt.
“Hold it there.”
Captain Healey placed a hand over my chest, feeling my heartbeat.
“Hmmm…”
He took my hand, and felt for a pulse at my wrist.
“You’re running fast.”
“Yes, sir.”
“Are you feverish?”
“No, sir.”
“Frightened?”
“No, sir.”
He dropped my hand. “Raise your arms above your head and hold them there.” He felt my armpits, which were slightly damp with sweat. “Good strong muscle tone, Jack.” He ran his hands down my sides, allowing them to rise and fall over the ribs, until they rested on my waist. He was standing before me, and I could feel his breath on my throat. I dared not look up into his face.
“Drop your pants.”
I knew that if I did so, my erection would be even more obvious than it already was, and I was nervous about Healey’s reaction. Had I misread the situation? Would he take this as some kind of unwanted advance and have me thrown back into prison? My hands hesitated at my belt.
“You heard what I said!” he shouted, straight in my face, a vein standing out on his forehead. “Drop your pants right now!”
I did as I was told. I was wearing underwear, but it was loose and stretched through much wearing and washing, and stuck straight out in front where it covered my hard prick.
“That’s better,” Healey said, still standing so close that the tip of my cock almost brushed his pants. He didn’t move. “You’d better learn to take orders, Edgerton. “Now lose the underpants.”
This time I did not hesitate, and I kicked the last remaining items of clothing away from me. I stood completely naked, and fully erect, in front of Captain Healey.
“Good boy. You’re learning. Now, what’s this?” He tapped the end of my dick with his pen, which got smeared with precum.
“That’s my cock, sir.”
“It’s your penis, Edgerton. You’re going to have to learn the right names for things if you’re going to be working for me. Your penis.” He gently took hold of it for emphasis. “And these are not your balls.” He moved his hand down and cupped me. “What are they?”
“My testicles, sir.”
“Well done.” He rolled them around in his fingers. “They feel healthy, Edgerton. When did you last ejaculate?”
“About four days ago, sir.”
“Four days? At your age I was shooting twice a day. You have a problem in that department?”
“No, sir. But I’ve been feeling very low.”
“You don’t look low now, Edgerton. You look pretty… up in the air.” My cock was throbbing as he “examined” my balls, and a drop of sticky fluid gathered at the head. “You should try to empty them more regularly than that, Edgerton, it’s not healthy to keep it all stored up. I always ensure that I ejaculate at least once a day.”
“Thank you, sir. I will, sir.”
“Now bend over the desk.”
“Sir?”
“I need to examine your anus.”
I leaned my elbows on the desk. Healey strode around to the rear.
“Not like that! You look like a schoolgirl at a church picnic!” His boot pushed my right foot to the right, my left foot to the left until they were a yard apart, and he pushed me forward. “That’s better. Let the dog see the rabbit.”
It was a position to which I was well accustomed, as any reader who has bothered to travel this far with me will know all too well. I rested my head on my forearms and waited for whatever Healey wanted to do to me.
A hand (warm, as he had promised) was placed on either buttock, and they were pried apart to expose my hole. Despite the lack of bathing opportunities, I had been sure to keep my ass clean with cold water and rough paper. Despite my good resolutions, I was keeping myself “nice” just in case of—well, situations like this, I suppose.
Healey was taking his time examining my asshole, and I could hear that he was breathing rather more heavily than before. Well, if he wanted to look at it, I was happy enough to show it. I pushed it out a little bit.
“Good. That all seems to be…in order…” For the first time he sounded less certain of himself. “Have you ever had any trouble with hemorrhoids?”
“Not as far as I’m aware, sir.”
“I’d better check. They’re a big problem for so many of our soldiers.”
“Yes, sir.”
A finger started rubbing and poking my ass; I relaxed my muscles, as I knew well how to do, and it popped in to the first knuckle.
“Seems healthy… Let’s see…” The finger delved deeper, and I pushed back against it. Even without a drop of lubrication, not even spit, I could take a good deal without pain. Healey’s finger entered me to a depth of maybe two inches, and moved gently in and out.
“Good, all clean and clear,” he said, slipping the finger out; I let it go reluctantly. My hard cock was pressing
against the edge of the desk, which pushed it back down between my legs; Captain Healey could see that I was even more turned on by his anal prodding.
“Of course, I really ought to check your…er…prostate gland,” he said, referring quite pointlessly to his paperwork. “Usually we use a piece of specialized equipment for that, called a proctoscope, a big metal dingus that goes up there and enables us to see if it’s swollen or inflamed. But I don’t have one here.”
“No, sir.”
“I can find out everything I need to know by feeling it, of course.”
“Then go ahead, sir.”
“That will require me to insert at least two fingers quite a long way into your rectum.”
“Yes, sir.”
“Do you think you can take that, Edgerton?”
“I’ll do as I’m told, sir.”
“Good. Good boy. Now, in order to do that, I need to lubricate your rectum with some special cream, otherwise it will be painful for you and there will be too much resistance for me. Do you understand?”
“Yes, sir.”
He rummaged around in a desk drawer and produced a small white ceramic pot with a screw lid. It looked and smelled like hair pomade, a product for which Healey could have absolutely no use whatsoever, so I assume that he kept it in his office for just such “medical” purposes. Whatever it was, a large gob of the white, greasy substance on the end of his index and middle finger was soon applied to my asshole, and allowed him to glide in without inconvenience. I sighed, and opened up to him. My cock was oozing, and I made no attempt to hide my pleasure, clenching and loosening my ass around his invading fingers. He enjoyed the ride for a while, and forgot himself enough to fingerfuck me a few times, but then he remembered that he was meant to be examining my prostate and continued his inward passage.
When he reached his goal, and pressed it, I groaned with pleasure.
“Does that hurt, Edgerton?”
“No, sir.”
“How does it feel when I press it like this?”
“It feels fine, sir.”
“Can you explain how it makes you feel?”
“It makes me want you to do it more, sir.”
“I see. Like this?” He pressed more, harder, letting his two fingers slip and slide over the sensitive spot.
“Oh, yes…”
“What would happen if I stuck another finger up there?”
“I…don’t know, sir…”
“Think you could take it?”
I knew damn well I could, and a whole lot more, but I thought it was best to give Healey the impression that I was learning obedience. “Try it, sir.”
A third finger joined the other two, and my ass was well and truly stretched. Healey was obviously enjoying it as much as I was, and allowed himself to fuck me that way for much longer.
“You need to ejaculate, Edgerton.” He was telling me, rather than asking me. “Do you think you could do it if I keep doing this to you?”
“Yes, sir.”
“I need to ejaculate too, Edgerton. I haven’t done it yet today.”
“Yes, sir…”
“Can you see any solution to the problem?”
“Perhaps…”
“Yes?”
“Perhaps if you stuck your co—your penis up my rectum, sir, we could both ejaculate together.”
“You’re a smart boy, Edgerton. That’s an excellent idea.” I looked over my shoulder, and saw him lowering his pants. He placed another gob of grease on the end of his big, hard dick and started slicking it up.
“Let me, sir.”
I reached back and smeared the grease all over his dick, enjoying the heat and the girth of it, running my finger along the huge vein that ran from his bush down to the head, bifurcating just before it disappeared. Healey stood with his hands on his hips and let me take my time.
“I’m ready for you now, sir.” I guided his prick toward my hungry hole. With so much lubrication, this was going to be a very smooth ride. I leaned over the desk again and prepared to be entered.
He was in me and up me in seconds, the head of his hard cock pressing against my prostate just as his fingers had done. I felt his bush against my buttocks and knew I had taken all he had to give.
“Am I doing well, sir?”
“You’re doing fine, boy. If I do this”—he fucked me slowly—“I’ll be ready to shoot pretty soon.” He was starting, to my great relief, to drop the medical jargon and use the words of the bar and the barracks.
“If it helps, sir, you can fuck me as hard as you like. I can take it.”
“Good boy. I’m going to fuck that ass as hard as it’s ever been fucked.” This I doubted very much, thinking back to some of the use my ass had suffered, but I said nothing. And indeed, the captain had a lot of energy. He pumped in and out of my ass like a piston, and even without touching my cock I knew that I couldn’t hold out much longer. Fortunately, the captain wasn’t far behind me.
“Oh, fuck, you have a sweet ass,” he said, drops of sweat falling from his forehead onto my naked back. “My dick feels so good up there. Oh fuck.” He pushed right inside me, and fell onto me, pressing his chest against my shoulder blades. I felt his lips on my neck, his tongue, his teeth.
“Fuck, I’m gonna come inside you, boy. You ready for me?”
“Yes sir.”
He pumped harder, faster, and started spewing a great load up into my guts. It felt so good. And, just as he was shuddering into the last few spasms, I managed to squeeze a hand down between my hips and the desk, and grabbed my prick.
“Hold it, boy.” He pulled me back, stopped me from touching myself—and kept his prick firmly lodged inside me. “We’ve got to do this properly.”
He withdrew, spun me around and sat me back on the desk, pulling my legs up by the knees. Then he plunged his still hard cock into my wet ass and proceeded to gently fuck me. “This way I can see what you’re doing.”
I needed no prompting and took hold of my cock. I was determined to give him a show, to keep him inside me for as long as possible, so I didn’t tug as hard as I could—that would have put an end to our fun. But, even lightly caressing myself, the sensation was too much. Under Healey’s hungry wolf’s eyes, I shot a huge load over my stomach. It ran down my sides and into my navel. Such was the intensity of the orgasm that my ass shot his prick out.
We stayed there without moving for a while, both our cocks softening, the spunk running out of my ass and down my body. I assumed that Captain Healey would tell me to get dressed and throw me out. Instead he helped me to my feet, put an arm around my shoulder and ruffled my hair.
“Welcome to the army, Private Edgerton. You’re going to make a very good soldier.”
XII
I MIGHT HAVE STAYED IN THE ALHAMBRA THEATER FOR THE rest of my life, I suppose, every day sinking a little deeper into a mire of heedless hedonism, had it not been for a clarion call from the very last quarter I expected.
Captain Chester had never struck me as a moral man, certainly not a patriotic one; his only interest seemed to be in keeping himself safe, getting laid, and making as much money as possible. I wouldn’t describe him exactly as a war profiteer, but he certainly recognized that, in the siege situation that beset Richmond during that nightmarish phase of the war, there were plenty of people looking for distraction and entertainment—and he did all he could to provide them. The regular business of the Alhambra was doing very well, and there were scarcely ever empty seats. Since Chester’s wife had left town to seek refuge with relatives in Tennessee, the Captain had dropped all pretense of preferring women and installed Billy in the vacated marital bed—although they were far from faithful to each other. Billy, indeed, was fast turning into the most popular attraction in town.
The Alhambra’s public shows were pretty risqué, with scarcely draped dancing girls and handsome young men showing as much flesh as the Captain deemed advisable. Under the circumstances, nobody was going to bother raiding the Alhambra for indecency;
the authorities were otherwise occupied. The private shows, of which I was a regular star, were becoming more and more popular, and I believe that Chester could have turned the Alhambra over entirely to the kind of performances I have described, had it not been for his need to keep up a respectable front. That dozen or so gentlemen who first saw me “rape” Billy soon grew to 20, 30, even 50, all of them paying top dollar for the chance to see some real cock on stage. We the performers did a healthy trade with our growing list of admirers; even Charlie, who still professed to prefer women, realized that there were far greater rewards to be had from men. The three of us were doing well for ourselves. Billy and I were saving; Charlie was spending, dressing like a gentleman, and looking around for a young girl of good family who would bring a decent dowry. Some of his gentleman admirers went so far as proposing their own daughters as prospective wives, on the basis, I suppose, that it was better to retain such “talent” as Charlie’s within the family circle. In any case, our prospects were good, and we frequently toasted our success, mindful always of the dire circumstances in which we had met. “What would that sheriff Jed Brown say if he could see us now?” Billy wondered, laughing, more than once, and we’d fall into reminiscing about how clever we were to escape from jail, how funny Jed Brown looked flailing around in a puddle of piss.
One afternoon, as Billy, Charlie, and I were drinking a pot of coffee in the dressing room and recounting our exploits of the previous evening—Billy was showing off a very elegant diamond clip that he’d been given for fucking an old man up the ass while he (Billy) wore full drag—Captain Chester walked in with more than his usual air of self-importance.
“Boys,” he said, “the time has come for all able-bodied men in this here town to do their duty and stand up and be counted.”
“Shit,” Charlie said, having been comprehensively drained by an extremely greedy married couple the night before, “I don’t think I can get it up again before tonight. It’s sore enough as it is.”
“Not that sort of standing up,” Chester said, although he did sneak a peak at Charlie’s groin, which Charlie was rubbing in an offhand sort of way. “I mean, we have an opportunity to make something glorious of ourselves by fighting for freedom and truth and the rights of the individual.”