He was young; cute; Hispanic; had a very nice smile; had a small, perfectly formed body; and moved like a dancer. Any three of those were good enough to make me hard. I immediately went hard for him. His name was Manuel. I guessed Brazilian from his bronze skin color. But then we were only ninety miles from Cuba.
I was on a punishment assignment from the Agency. We had a listening post in Key West, at the very tip of the key, on the small naval base, and I’d been sent to head up the operation–and maybe to close it. The ice around U.S.-Cuban relations was thawing and Fidel was dead. The unit was on Key West to monitor every breath a Communist country just off our shore took and, historically, to cover Fidel’s three-hour diatribes on the radio. Times were changing. We could squeeze more juice out of Cuba off the Internet than we could off the radio, and a shitload of Cuban refugees were sitting in Miami who were more than happy to squeeze data on Cuba off the Net every day and to make sure the U.S. government knew what was happening there.
The Key West bureau was a dying office, and that’s how my boss, Sam Winterberry, had pitched a hand-slap assignment for me to the guys and girls–increasingly girls these days–on the seventh floor. I’d been caught fucking the college-age son of the Agency’s comptroller, Jerry Ortez, and Ortez wanted me sent to Hades. What could I do? The lad–who was well of age, mind you–was young; cute; Hispanic; had a very nice smile; had a small, perfectly formed body; and moved like a dancer. Just looking at him made me go hard. He also was quite willing and made very nice compliments about the size of my cock and about what I could do with it. He had that “take me like a virgin” act that got to me every time–and I’d taken him like he was a virgin every time.
They couldn’t spear me for spiking a man, even though that still was a separation offence in the Agency, because that was my job–I worked for Sam Winterberry’s Candy Store unit, which put into play the truism that the world’s two oldest professions–spying and prostitution–worked well together as an intelligence-gathering activity. So, I fucked women and men and, on occasion, got fucked, all in obtaining valuable intelligence for the Agency. Being a switch hitter, as I was–Sam Winterberry was fucking me–I was actually quite an asset for the Candy Store unit operations.
So, what officially was a crime in the Agency was, unofficially, premium good business, and the worst Ortez could subject me to was a dead-end assignment until my Candy Store services were vitally needed by Uncle Sam again. So, Sam had emphasized the “business is dead, it’s at the end of the world, and it probably is closing” aspects of the Key West bureau to the brass and the seventh floor and failed to mention that Key West is the gay male mecca of the United States. And the seventh floor bought it. That there was male pussy romping from shore to shore down in Key West was a plus for Sam. He wanted to get my mind off Ortez’s cute son. It took thinking of the honey pots down there to do it. As it was, I was still banging young Ortez, taking him like he was a virgin, on the night before I pointed the headlights of my Camaro toward Florida. And Sam banged me the morning I left. Both Sam and I well knew I wasn’t a virgin.
So, I was sitting at a crowded outdoor café on DuVal Street two weeks after taking up residence in Key West, and he appeared before me on the other side of the café table I was at–one with two chairs at it and I only occupied one. He was holding a coffee mug and a croissant. I was folding up my New York Times and had an empty cup and a small plate with croissant crumbs in front of me. It was quite natural to get the idea that I was about ready to vacate the table.
“Excuse me. Were you about to leave? There don’t appear to be any other open chairs.”
I looked up at the young man. He was young, cute, Hispanic, and had a great smile and a small body to die for. His hair was black and curly, with a curl dipping down to an eyebrow. He was minimally dressed, with tight shorts, sandals–without socks, naturally–and a mesh shirt showing a nicely muscled, bronzed torso. There wasn’t anything unusual about that; all men dressed gay in Key West, and most were gay. What was really nice about Key West was that you could assume a guy was gay unless you found otherwise; you didn’t have to wonder if he might be gay. The interesting thing here, though, which caught my attention immediately–other than that he wore the uniform very well–was that the tight mesh T-shirt revealed to me that he had a ring in his left nipple. The signal wasn’t universal, by any means, but years ago a ring in the left nipple had replaced an earring in the right ear as a declaration of a seeking submissive bottom–my favorite brand of young gay men.
I did a fast look around the café. He hadn’t been shitting me. The only available chair was the one at my table, the one he was standing behind while looking oh so fuckable.
“Sure, no problem,” I answered breezily, “as long as you don’t mind sharing the table long enough for me to have a second cup.” I lifted my mug and looked for a waiter, there fortuitously being one almost at my elbow, and signaled that I wanted another hit of caffeine. It would be my third, not my second, cup of java, but who was counting?
With a smile and a, “Hi, my name is Manuel,” he sat down across from me.
“Chaz here,” I said. “It should be Charles, but this is Key West. We like to go very casual down here.”
“Yes, we do,” he answered with a repeat glorious smile.
That led into a discussion of where we each came from, how old we were. I was relieved to hear him claim he was nineteen. He smiled when I said I was thirty-one and told me I looked a lot younger–and in great shape–but that he liked older men. I, of course, didn’t mention that I didn’t think thirty-one was an old man. We weren’t yet at the point where I could indignantly say that I could keep it up for hours, reload fast, and achieve three ejaculations in an hour–with pretty impressive wads of cum too. He gave me an “I didn’t mean to get into comparative ages” look and then we moved to what we were doing in Key West. I told him I worked for a news agency, which, in loose terms, was true. He told me he was a college student.
“Well, not what you would call a real college, I guess,” Manuel said. “I go to the Key West Yoga College of India, over on Southard Street. But I also do some part-time work with a caterer–serving at parties and such.”
“An Indian yoga college?” I asked, making my voice sound like I was intrigued. And of course I was.
“Yes. It’s a school of yoga. It helps with flexibility. I do some dancing, but I wanted to qualify as a yoga instructor, so–”
“Dancing?” I asked, fascinated.
“Yes. I dance a pole on weekend nights at the Bourbon Street Pub. Right up the street here, on . . .” He was blushing, as if he’d said too much. He hadn’t said too much for me.
“Yes, on DuVal,” I supplied.
“You know it?” he asked. It was a key question. It was one of the premier gay cruising and strip clubs on a premier gay island.
“Yes. I go there,” I said. “I haven’t been there on a weekend, though. Too crowded for an old man like me. But I’ll have to make a point now of taking it in on the weekend.”
“You’re not an old man,” he said. “You’re in great shape. And you’re a real hunk, if it’s OK for me to say.” He had a forearm resting on the table and I reached over and stroked it with the tips of my fingers while giving him “that” look with my eyes. He gave me a submissive’s look back–a slight dipping of the head and looking up into my eyes under fluttering eyelashes. I could feel the tremble in his forearm as I took up a stronger grip of that with my hand.
“And, yes, Manuel, I’m gay. I’m a power top. And you? You’re a submissive bottom, aren’t you?” I didn’t mention that, for the right man, I could be a submissive bottom too–and that, on occasion, I wore a ring in my left nipple too. That revelation wasn’t needed in this transaction.
He managed a deeper shade of blush. “How do you know that?”
“The nipple ring. Unless, of course, you aren’t following the convention, such as it is. Is it not true that you are a seeking submissive?”
“No, yes. Shit, I’m not good with sentences like that with the screwy negative words. Yes, I’m a bottom. But I didn’t mean . . . I didn’t sit here to . . .”
“Were you shitting me, Manuel, about not thinking I was too old? You said you liked older men. I heard that. Maybe you didn’t think I’d heard you say that, but I did.”
“Yes, I like older men. I had an older guy who took care of me, but . . .”
“But no one owns you at the moment? You don’t have a master right now? Someone to control you and take care of you and use you right?”
I could see that my calculated use of the word “master” had not gone unnoticed–and, I think, unappreciated. “No . . . no I don’t,” he murmured.
“Someone to contain you and give you direction? Someone to use you hard–to take advantage of that flexibility that’s important for you to maintain?”
“No. I don’t have anyone like that at the moment.” His eyes were downcast, his trembling had increased a bit. The café was still busy–busy enough that no one was paying attention to us. The world was swirling around us, but we were isolated in a bubble, an island in the ocean of people pursuing their own interests, not ours. I had his full attention. I already was seducing him, fucking his mind. It was something we learned to do in my business. I was an expert in it, assessing each mark and doing it a tailored way for each. With some, like this honey, the direct “I want to fuck you” approach worked best. I could talk to him as dirty as I wanted to here at the table, and he would be focused on it, seduced by it. If I wove a web of dirty talk and images around him here well enough, he’d let me do all of that to him when we were alone. I’d been taught how to do this.
What I didn’t take into account, and probably should have, is that this was entirely too easy. He obviously wanted me to fuck him. I didn’t go over all of the “whys?” in my mind. I had been trained to do that too.
There would be a barrier between us and everyone else at the café. I pulled my right foot out of my sandal and rubbed my toes against his lower calf. He widened the stance of his legs. He maybe didn’t even notice he was doing it. It happened involuntarily. He was opening to me. I could, if I wanted, fuck him right here at the table–on the table, under the table, in his chair. He’d take me here and now if I told him he would.
“This man of yours–your sugar daddy, Manuel, was he a big man?”
“Yes.”
“I mean where it counted.”
“Yes.”
“At least ten thick inches?”
“Almost that.” At least he took that seriously enough to draw in his breath when I defined the inches.
“I mean all of that. No stopping half way.”
“Yes . . . almost.”
“So, you like men who are big–hunky–you can take it thick and long.”
“Yes, that’s the way I like it.”
“Good. That will be good then. You know what I’m saying?”
“Yes.”
“Long, thick, vigorous. And you want your man to be a little cruel, don’t you?”
I felt his shudder through my grip on his forearm. “Yes,” he whispered.
“Here, Manuel. Here’s a card with my home address on it. An apartment house over by the Truman Annex, near the gate into the naval station. In case you are free this afternoon . . . now, and in case you lose sight of me as I walk home from here. You’re going to follow me back to my apartment. Now. Do you understand?”
“Yes,” he said meekly.
“Good. I’m leaving money here, enough for both of us. I’m finished my coffee. I see you have a bit more to drink–and a few more bites of your croissant. That should take long enough that you can walk behind me but not lose sight of me, right? The master always walks ahead of the submissive, right?”
“Yes . . . sir,” he said, still looking down at his unfinished croissant, as I stood, left money on the table, and slowly sauntered out of the café and toward the Truman Annex. I didn’t look back as I strolled back to my apartment house. I was that sure that he was back there somewhere, following me.
I lived on the fourth floor. There was an elevator, but I was a fitness nut. I had to keep my body toned when I was in Sam Winterberry’s unit. But I had time to make it upstairs and get packets of condoms and a bottle of lube out and placed on the nightstand in the bedroom before I heard the buzzer sound down at the street door. I buzzed him in without looking to see whether it was Manuel or not. I was sure it was. And I went out into the hallway and looked down into the well, following glimpses of him as he wound around and around stairs and landings, rising up to me.
I pushed him down to his knees in front of me inside the foyer after I’d closed the door, unzipped myself, and made him service me for a few minutes. This was the mark on whether he was going to be coy or not–or even back out–whether he’d deep-throat me, on his knees, just inside the apartment door. No preliminaries; right to business. After exclaiming how big it was–“Well, I did tell you,” I said–and gagging at his initial efforts to deep throat it, he handled it like a pro.
When I knew that we were going to have smooth sailing this afternoon, I lifted him up on his feet. He was a good foot shorter than I was, and his body was small, but it was perfectly formed–just the way I liked it.
“I want you cleaned out, and I want to be clean,” I said. “The bathroom is through the bedroom over there. You first in the shower. Then me.”
When I came out of the shower into the bedroom, he was leaning in a provocative pose, naked, in the frame of the floor-to-ceiling window of my bedroom, with the golden light of the sun glistening on his beautiful, small bronze body. He hadn’t bothered to dry himself off, and I was excited enough to take a fast shower, so beads of water were still taking their long, slow journey down the curves of his glorious body. The pose was studied, but I could tell that he was nervous and a bit scared at what was to come. That was the way I wanted him to be.
I fucked him there, at the window, from behind, as he leaned his chest into the frame of the window, rose on his toes and grabbed the brace for the curtain rod above his head, rested his cheek against the frame when we weren’t kissing, and jutted his bulbous little buttock out to me to take the thrusts of my cock up into him. I’ll give it to him. He could take ten full inches like a trooper.
And I fucked him a second time standing on the floor half way to the bed, with his little body plastered on my front, his legs hooked on my hips, his fists locked behind my neck, me clutching and spreading his buttocks with the palms of my hands, while he bucked vigorously against me, riding my cock hard, fucking himself. He was a firecracker, a regular hot pepper below the surface of his cute sugar coating.
And I fucked him a third time on the bed in inventive positions that emphasized his flexibility and aided my ability to ram him hard again and again and to mine his ass deep. He exhausted me, but after that afternoon, I had to rephrase my pitch of being able to shoot three times in an hour. I made it four with him before the first hour was up.
He was so sweet that, despite obviously being a professional at whoring, he also could take me in a way that made me feel I was taking a luscious young man for the first time. It was by no means the first position on the bed, but when we went into a missionary position, him on his back, legs spread and raised, back arched, and his hands clutching my shoulder blades, he cried out as I entered him and tightened up his channel to make me force my way in. He writhed and cried out a passionate, “Yes, yes, god, you’re a monster. You’re splitting me. Yes, take me hard, daddy!” And I did, giving it to him hard and deep, both of us crying out as he allowed his channel walls to open for me and his muscles to ripple over my cock and to draw me deep inside.
He was docile then for several minutes, lying still, his head turned to the side, sobbing quietly, the undone virgin. I gave it all to him, holding steady, ramrod straight stretched out over him, buried to the hilt, listening to him sighing and murmuring, “Yes, yes, yes,” until slowly coming to life, he started moving under me, setting his pelvis in motion, moving to slow writhing and then, crying out, “Finish me. Give it to me! Cum me!” he bucked against me, with me deep inside him, where I tensed, jerked, and gave him my seed, with him moaning and clutching my buttocks in his hands to hold me inside until he’d gotten every drop out of me. God, he knew out to milk me dry. He had to be a seasoned pro.
I zonked off on my back on the bed, with Manuel doing a writhing cowboy on my still-hard dick. When I woke, he was gone. He hadn’t left me a contact number, but I had a line on him. I should be able to catch him at the Bourbon Street Pub on the weekends, where I could watch him shake the cute little butt that I had split with my throbbing cock again and again.
I dozed off again, trying not to smile at the hardship tour to this backwater that Jerry Ortez had demanded and Sam Winterberry had slyly acceded to with a sigh of sympathy for me.
The sugar-coated hot pepper that was Manuel had gotten it good. And he knew he had. He was a mouthy little thing and boy did he know some dirty ways of telling me he had been fucked so hard his eyeballs were swimming in cum. He hadn’t wanted to use the condoms and I hadn’t been in the mood to insist. He’d declared his was checked weekly, and I knew I had a standing appointment to get checked after every fuck and, unbeknownst to the rest of the world, the Agency had its own miracle pills for such problems–both before anticipated sex and after unanticipated sex. One thing we didn’t want to do to marks we were trying to compromise and blackmail was to give them something that would kill them before we’d squeezed all of the value out of them.
“When you got it, you got it,” I murmured to myself as I drifted off into an exhausted sleep.
I fretted through the rest of the week, counting the hours before I could make a weekend appearance at the Bourbon Street Pub. I didn’t want to admit it to myself, but I was smitten with the sweet sugar-coated hot pepper Manuel–enough that I was questioning who was master and who was slave. My mind kept going to that moment in the missionary fuck when he went docile, completely open and vulnerable, laying there, sobbing quietly, his passage walls pulsating over my cock as I held it ramrod hard, deep inside him, sinking in an inch deeper than I’d managed ever before, the master subduing the virgin, waiting for him to come alive on the cock, which he did. He knew how to do undone virgin magnificently.
When I finally arrived at the pub that Friday night–and then returned on Saturday–he didn’t appear. For solace, I settled on another small, cute, young, Hispanic honey named Emilio, who perched on my lap as I sat on a stool at one of the bars, with my arms wrapped around his bare chest, while we watched the dancers on the poles and then the male strippers, and who gave no objection when, after stuffing a wad of compensating five-dollar bills in his waistband, I slit the tight nylon bikini briefs he was wearing along the line of his crack while he moved to the music on my lap and then unzipped and exposed my erection. After I rolled on a rubber handed to me by the bartender, who kept returning to watch us, Emilio slid down my pole a good seven inches and fucked himself on me as we sat on the stool and watched the world dance around us. No one seemed to mind that we were fucking. The bartender certainly didn’t seem to mind.
God, I loved this hardship assignment in Key West.
* * * *
The next Tuesday I was back at the open-air café on DuVal at the same rush hour time I’d been there when I hooked up with Manuel. I hoped he’d show up. I didn’t have any way of contacting him other than through the yoga place he said he attended or the Bourbon Street Pub, and, not wanting to leave tracks, I’d try those as a last resort. He didn’t show, but I ended up having a good time anyway.
He was older, perhaps late forties or early fifties, Hispanic, built like a tank, very capable and distinguished looking, and he had a nice smile. I was dressed in the casual office style of Key West–white shorts, white Polo shirt, and sandals, without socks–and thought that I might, if I didn’t strike it lucky, actually check in with the office after my coffee and croissant. The office didn’t need me. There were too many people and too little work already.
Even though he looked like a Fortune 500 executive, he was dressed in Key West casual: red gym shorts, sandals, and a black mesh athletic T that showed the musculature of a Zeus. Although he had been similarly dressed, Manuel exhibited as a David. This man’s torso was that of a mature man–but a well-toned mature man, and looking closer, I took in my breath. He didn’t have the nipple ring that Manuel had; he had a sleeve and pec tattoo–a colorful one that depicted a Japanese Samurai warrior flowing up the arm and around to where the warrior’s war-like grimace of a face was staring through the captive mesh of the shirt on the man’s bulging left pec.
He was standing across the table from me. The café was crowded, and once again it appeared my table had the only open chair. He was holding a coffee cup in one hand and a black leather bag in the other.
“Sorry, you look like you’re about to leave,” he said, looking apologetic. He also was looking Hispanically handsome. Argentina, I wondered. But then Cuba was only ninety miles away for Key West. “Do you mind if I take this chair?” he asked in a deep, rich voice.
“As long as you don’t break my heart and take it to some other table,” I said, giving him my version of a radiant smile. “Please, pull it up and sit with me. I was about to ask for a second cup of coffee.” He smiled and sat, as I flagged down a waiter wading around the room with a coffee pot and received another hit.
“You don’t have to be anywhere?” he asked, as he took a black case out of his black bag and placed it on the surface of the table. Once again I sucked air in as I looked at the case and recognized the logo of a gray G entwined with a lower-hanging yellow S embossed on a bronze medallion embedded in the case’s top. I looked up into the man’s eyes and found him watching me closely. I knew what the logo represented–G. S. Instrument’s Van Buren sounding wand set. From the way he looked at me, I knew he knew I recognized the emblem.
He cast an obvious look at the logo on the case and then at me. I did the same.
“You are still fine with me sitting here?” he asked.
“Yes, certainly,” I answered. Especially since we were here in free and open Key West, that was shorthand for him saying, “Will you go with me and let me sound you?” and me answering, “Yes.” We could have gone to wherever he would fuck my cock with those metal wands then, but I guess I was being too easy for him. He wanted to savor the buildup to seducing me to it.
That was fine. But knowing I would say yes cut out a lot of preliminary fencing for both of us. “No, I’m on my own,” I answered. “I have whatever time free that I want.” Even though I was here as the chief of one of the Agency’s listening posts, as the bureau chief, I pretty much was free to come and go as I wanted as long as I got the administrative work done. So I wasn’t lying to him. I had planned to go into the office from here, yes, but that little black case of his just might change my plans.
“Hector here. Hector Lopez,” he said, giving me an expectant look.
“I’m Chaz Findley,” I answered.
“Are you a tourist here in Key West, Chaz?” he asked.
“Not really. I’ve recently arrived, but I’m working for a news agency down here.” It was the same job I’d given Manuel, and it still technically was true. “And you?”
“I’m a doctor,” he said, with a smile, lifting the black bag that he’d taken the black case from. The black bag did look very much like a doctor’s bag, I thought, now that he’d mentioned it. I gave a little shudder at the thought of what the doctor could have in that little black bag of his. “And I own various other businesses in the keys,” he added. “Pity that you aren’t a tourist.”
“Why so?” I asked.
“Handsome, well-built men like you who come down here as tourists are usually looking for one of two things. I’ll have to admit that I like to help these men get what they want, assuming they want something very, very special. Exotic drugs, for instance. And other exotic experiences.” One of his fingers went to the edge of the black leather case and he nudged it an inch toward me. He wanted me to look at the case, which I did. I don’t know what more he wanted me to do, but I stole a march by moving my hand and extending a finger that touched both the case and his finger.
He smiled and said, “That’s why I asked you if I could join you–in case you might be interested in joining me. I did mention that I was a doctor, didn’t I? I have some special skills and some specialized interests.”
“Tourists are looking for two things, you say?” I asked, knowing what his answer would be.
“Tourists with the roving eye such as I saw you have, and magnificent bodies such as I see you have come to Key West to lay or be laid–and with added benefits they normally couldn’t get where they came from.”
“And residents down here can’t have the same interests as tourists have?” I asked.
“Of course they can,” Hector said, with a smile. “Men who come to live in Key West can be connoisseurs in the art of personal pleasure and satisfaction fulfillment. I think perhaps that you can. You had that look of refined tastes about you when I looked over those at the café. Have I thought incorrectly?”
“No, not at all,” I answered. It must have been the answer he desired, but he then slipped a foot out of its sandal and raised it, pressing it between my thighs from across the table. I spread my legs enough so that he could place the heel of his foot against my crotch. He pressed it into my crotch hard, and I grimaced for him, but I reached down with my right hand and held the foot in place.
He smiled again. “Which kind of tourist are you available to be, Chaz. Do you lay or get laid?”
“Yes,” I answered and he laughed.
“Used or abused?” he asked.
“Yes,” I again answered. His eyebrows went up.
“You recognized the logo on this box, didn’t you?” he asked. He opened the box to reveal graduated sounding rods–which were used to invade and stimulate men’s urethra channels. There were eight of them, slim silver rods with curved tops, arrayed on a red velvet lining.
“Yes.”
“You have observed these in use before?”
“Yes.”
“These have been used with you before?” He closed the case almost as quickly as he had opened it, presumably not to attract too much attention.
“Yes.” I was giving him a level stare, and he was returning the same, gauging me, looking for any sign of withdrawal. I gave him no such sign.
“All eight?”
“I believe only six.”
“But you would have liked to have taken all eight?”
“Yes.”
He gave me another small, cruel smile and then he dug the heel of his foot into my crotch, and I held him there with my hands under the table, taking the pressure and the pain on my genitals.
“I keep a motel room not far from here, over near Lands End beach. If you will go with me there now, I will pay you $200 if you let me fuck you–$200 more if you let me fuck your cock with the sounding wands.”
“But you don’t want me to go with you just for a fuck, do you?” I asked. “It’s not really worth your while unless I let you sound me, is it?”
“No, it’s not,” he conceded, with a smile. “I want to sound you.”
I rose from the table and dug into my pocket for money to pay for my coffee and croissant. The man retained a nearby motel room for these trysts. He obviously was a serious player. I felt myself trembling, my cock going hard.
“No, I will pay for us both,” Hector said in a commanding voice as he too stood. “And let us be straight. You will be bound. I will use you cruelly.”
“Yes, it’s what I want,” I murmured, lowering my eyes. For him. For men like him and Sam Winterberry, I would be submissive. The money was immaterial, but the feeling of being a totally used whore was, in itself, arousing.
“You will walk at least ten paces behind me to the motel,” he said.
“Yes . . . master,” I answered. I had tried, but never been successful, in explaining the psychology of a switch hitter in this business. All I can say is that I found it supremely arousing to dominate a younger man while at the same time found it equally arousing to be dominated myself by an older man.
I panted heavily as I lay, curled up into myself, on the small of my back at the foot of the bed in the motel room. We were both naked. His body was beautiful for a man his age, solid, muscular. My legs were painfully bent and angled to the side, one restraint gripping my legs below the knees and linking them with a strap running around the back of my neck and other restraints on either side binding my wrists to my ankles. I was drooling and biting into a rubber ball mouth gag. I jerked each time one of the balls in a string of balls surfaced from my ass as he gently pulled on it. I’d watched at least six graduated balls, the string having come out of that black bag of his, being pressed inside my channel, which struggled to open to take them–but which had opened and taken them.
The third larger sounding rod was buried in the piss slit of my cock. Hector was holding the cock steady and erect with one hand while tugging the balls out of my ass with the other. He was crouched over me, staring down into my face, savoring every subtle change in my reaction to his playing with me with his toys.
Two balls still in my channel, he left those with his right hand now free brought his fingers to the tip of the sounding rod still outside my cock bulb. I moaned deeply as he twirled the rod slowly in my urethra channel, and then I screamed through the gag as he withdrew the rod and my ejaculation came with it.
We held there for several minutes. He was waiting for something. He was cupping my cock, so I presumed he was waiting for me to recover from having ejaculated and my cock having lost its ram-rod hard state. I was still half hard, though. But he was waiting for me to harden again. He had the seventh rod out of the case and I knew he intended to use them all before he was done. I moaned as he started to slow stroke my cock and I felt myself going hard again. And then I was groaning and biting on the ball gag and he was twirling the next-to-largest wand inside my urethra, deep. As he had promised, I was going to get all eight of them. And when he did me with the eighth one, I ejaculated again.
The last of the balls came out of my ass, to be replaced with the slide of his hard cock up inside my channel. He grasped my hips and started a serious, building pumping of my ass. His eyes went large and he laughed when he realized that I was using every leverage I could get, despite being trussed up as I was, to move my pelvis with his–to be an active partner in the fuck and not just his prey.
God, the hedonist life in Key West was good.
* * * *
I was surprised when I went to the mail slot of my apartment house on Thursday to find an invitation to a swim party on Saturday afternoon from Hector Lopez. It gave an address on a street of exclusive houses above a beach on the water in the northwestern sector of the key. The invitation was written on stiff vellum in fancy calligraphy. A less fancy note, in a scratchy hand, was enclosed in which Lopez asked me to come to the party to service a client he was trying to strike a deal with. I would be paid $500 for giving the client whatever he wanted. A subscript to that said that Hector would pay more if it wasn’t evident that I’d enjoy it so much.
Cheeky devil, I thought, but it made me laugh. It also made me want to go to the swim party.
That explained the invitation. What it didn’t explain was how Lopez had gotten my address. I suppose, given my name, which I’d told him–at least the name I was publicly giving down here in Key West, would have allowed him to find me. But I hadn’t really been in Key West long enough to establish connections. That he could have found me so quickly spoke to the power of the man here on the key. I put in a call to Sam Winterberry back in Langley.
The house was in one of those rare enclaves on Key West where private residences had beach access to the sea. The house itself was a rambling, two-story stucco and glass modern building with a huge swimming pool and an even more expansive terrace behind it, all sitting on a rock outcropping overlooking a beach. It was an all-male party, which didn’t surprise me, but on the surface it appeared to be coed as many of those in attendance were transvestites, some very convincing in their skimpy bikinis.
Lopez took me almost immediately from the front door–with a stop in a guest bathroom, where I stripped down to a blue silky Speedo–to the pool area and, as he took drinks off a tray, he handed one to me and another to a large, bulky man, in the nude, as many of the party guests already were, and introduced the man to me.
“Chaz, this is Daniel Cruz, a business friend of mine I have told you about. And I’ve told you about Chaz, Dan. I’ll have to mingle for a while, but I will speak to you both later. I’ll want to know how you are enjoying the party–and each other.”
With that, he was off, and I was standing there, talking to a naked Hispanic man who probably was in his mid fifties. He was about a zillion feet tall and broad and thick of body. He’d almost certainly been an athlete at one time but age had been getting to him. He had a beer belly–not a gross one, but a noticeable one–and his pecs were beginning to be better described as breasts. He was covered in black and blue tattoos, most of which seemed to be crudely inked, and none of it telling a greater story. Still, he was a muscular man, with good bicep definition. and he had what was definitely a redeeming feature. He was hung like a bull. His balls hung low, the testicles plump and distinctive in the drooping ball sac, and his thick cock was making an effort to reach for his knees. At least it was until I was brought forward to meet him. The cock was already at half attention now, thickening, lengthening, and rising up the longer we stood there, looking at each other, neither fast on bringing up chit chat.
Daniel Cruz was clearly pleased about being introduced to me.
We both knew what I was there to provide for him. With each passing second of awkward silence, his cock increasingly told the story of where we were headed. I didn’t particularly mind. He was a huge bear, but he wasn’t exactly gross. And, boy, was he hung. I appreciated a challenge in that department.
I’d only drunk half of the drink Lopez had handed me–I didn’t even know what it was–when the man–Dan–was reaching out with a thick-fingered mitt, taking the glass out of my hand, setting it down on a table at my elbow, and saying, “Hector has such a nice swimming pool. I think we should try it out.”
“Yes, it is a nice pool,” I said. There weren’t many in the pool. The party was already well under way. There was loud music and dancing, and I could already see that there was humping going on on the chaise lounges and even down on towels on the beach. Whatever Cruz and I did wouldn’t surprise anyone or get much attention.
“I want to take you to the pool,” he said, and then, before I could tell him that was just fine with me–that I was on board with the plan–he clarified. “I want to take you in the pool.” In case I didn’t understand, he reached out and cupped my balls and cock through the thin material of the Speedo. “Nice, very nice,” he muttered.
“Yes, let’s get into the pool,” I said, making my voice sound breathy, like I couldn’t wait to be riding that cock of his. And, indeed, I was looking forward to the challenge.
We dove in and swam around in our own patterns for a few minutes. He was a strong swimmer–strong swimming strokes that I assumed he could match with the thrusting power of his cock. He finally surfaced in front of me as I had my feet down in a section of the pool where the water came up to my nipples. His long, strong, beefy arms went around me and he took my mouth in a kiss. He was a good, possessive kisser.
“Take your swim suit off and give it to me,” he commanded as we came out of the kiss.
“You want me to take it off?” I asked. “You don’t want to take it off me?”
“It is your statement that you will let me fuck you,” he said. “You take it off and give it to me and you are confirming I can fuck you.”
I think the whole reason I’ve been invited here is for you to fuck me, I told myself, but It didn’t’ say that to him. As I pulled the Speedo down and off my legs and handed it to him under the surface of the water, what I said was, “You can have the suit. You can have anything you want from me.”
He gave me a grin and then swam over to the side of the pool and deposited the Speedo on the lip of the pool. Turning then, he motioned to me. “Come here. Come to me.”
I swam over to him and he wasted no time in taking me. He turned me belly to wall, my elbows on the lip of the pool either side of my Speedo and pulled in close behind me. I could feel the insistence of his hard-on on my thigh and then his fingers at my hole. I cried out in surprise, my cry being covered by the loud music and largely unnoticed by those getting their own desires on, although a few turned their faces to me briefly and smiled in recognition of what I was getting. What I was getting was having my ass channel brutalized by thick, invading fingers, which were working on opening me up and not caring what I thought about it.
Cruz wrapped a beefy arm around my neck, pulling the back of my head into the hollow of his neck, and dug and dug with his fingers, as I writhed under his control and cried out–as much in passion as in pain–at the cruelty of his penetration. I cried out again when the fingers were replaced by the forced entry of the thick cock. He pumped me slowly for a few minutes, gaining a bit more in depth with each push, until I was able to accommodate the size of him and quieted down to deep moans and groans.
Again, only occasionally did eyes focus on us, and the faces showed nothing more than admiration for the facial expressions and moaning that the big bear of a man could pull out of me. Lopez drifted by once, stopped, looked at us and smiled, and then walked on.
When he had completely cowed me, Cruz pulled out of my ass without coming and turned me so that his back was to the wall and I was facing him. “Feet on the wall, grab the lip of the pool with your hands, ass on cock, and fuck yourself,” he commanded. I understood what he wanted, and it was quite OK with me. I grabbed the lip of the wall on either side of his shoulders, raised and spread my legs, placed my feet on the wall tiles on either side of his waist, and waited as he moved his cock into position at my hole. Then, at his muttered command, I thrust my pelvis forward, taking him deep inside me in one long slide. He worked my cock with one hand, palming one of my buttocks cheeks with the other, as I rode his cock.
He held there, rock hard, for a good ten minutes, urging me to take him deep and then deeper, while I huffed and puffed to do what he demanded. Eventually, though, he lost the patience of essentially just being a gigantic dildo, grasped my buttocks and started pounding hard, both pulling me to him and thrusting forward with his hips into me. I screamed for a while, with few noticing other than smiling and nodding their heads and agreeing with each other that I was having the hell fucked out of me. At length, I lost my hold on the lip of the pool, arced my back into the water behind me. I floated in semiconscious silence while he continued slamming me on and off his cock to what was an almost simultaneous ejaculation.
* * * *
I roamed the party on my own for a while, returning smiles and touches and gently pushing away grasping hands. Lopez had told me that my duties weren’t over, that Cruz was resting, and not to leave the party yet. I didn’t know what else they had in mind, but I didn’t particularly care. Cruz might have had the biggest cock I’d ever taken. I didn’t mind having another crack at it. Even with all that preliminary digging and opening up with his fingers, it had been a challenge to sheath the cock. But he’d made me take him to the hilt. It was an accomplishment to crow about. And it deserved an encore.
I was walking aimlessly about, reversing when it looked like I was entering the orbit of a big bruiser who was giving me the eye or when I saw a sweet young honey pot I wouldn’t mind spiking myself when I saw him. Manuel was coming out of house, hefting a tray of drinks. He was in a skimpy Speedo, but it hit me that he was there as a waiter. He had told me he worked part time with a party caterer. Still, I was trained not to believe in coincidences.
I caught his eye. He gave me a look of surprise and then a sensual little smile. We both paused, not knowing what to do next. He recovered before I did and nodded with his head toward the interior of the house. He put his tray of drinks down on a table just outside the glass doors into the house, turned, and was gone.
I followed him into the house. I saw him at the foot of stairs leading up to the second story. When he saw that I’d come into the house, he mounted the stairs to the second story and my eyes followed his cute, rolling buttocks. When I reached the top of the stairs, he was standing down a hallway, in front of a door. When he saw me reach the landing, he turned and went into the room.
The room he went into was a bedroom. He was lying on his back on the bed when I entered. He’d stripped his Speedo off and was lying with his legs spread and bent and his hand on his hard cock. I came down on top of him on the bed, slapped his legs even more open, thrust inside him, and fucked the shit out of him.
It was a while before we got to my favorite part–him playing the role of the undone virgin. He was flat on his stomach, angled on the bed, one arm drooping off the side of the bed, an expression on his face that managed both grimace and walking on the clouds. I was riding his ass, stretched on top of him in pushup position and doing pushups on his ass. His moans and groans egged me on to take him harder, deeper–to pop his man cherry. It was all very arousing.
We parted with his promise to come out to my car after he’d finished helping with party cleanup and to come back to my apartment with me. I didn’t have long to think about what I’d do with–to–him that night in my own bed, because Lopez and Cruz found me and hustled me to yet another bedroom, one outfitted more in keeping with Lopez’s kinky sexual interests.
I was bound to the bed, my arms stretched wide above me and restrained at the corners of the headboard, and my legs spread and raised, manacled by restraints at the ankles on straps suspended from the ceiling.
As if his cock wasn’t big enough, Cruz fucked my ass with the biggest dildo I’d ever seen, while Lopez crouched over my chest and fed his cock into my mouth.
“Hold steady. You’ll want to hold steady, Chaz,” Lopez whispered to him as he crouched beside the bed, feeding a sounding rod into my cock. At the same time Cruz was feeding his monster cock into my ass channel. While, yes, holding as steady as I could, I let my mouth scream the pain-passion of their attention to my body.
The finale was a double, with Lopez under me, my spread-eagled and restrained body stretched on his, my chest pointed up and with Lopez’s hands on my waist and his cock in my ass. Cruz knelt between my spread thighs, his knees on either side of Lopez’s thighs, forced his cock inside me above Lopez’s buried staff and pumped me to a three-way creaming.
“Attend us downstairs in the Library after you’ve cleaned up,” Lopez said, as he unbound me. He’d already gone off and showered while Cruz was still fucking me. Cruz was gone as Lopez freed me, though. “The library is on the front of the house, down the stairs, to the right of the door into the front foyer,” Lopez told me in a quite calm voice as he left. No “Good job” or “You were great.” I’d done his work, and that was that.
When I entered the library, dressed in the clothes I’d come to the party in, sure now that the fucking was over and I’d earned the $500 Lopez had agreed to pay me, I’ll have to say I wasn’t surprised at what I found. The two men were sitting in chairs pulled up at two sides to a mahogany desk with miles of surface. A third chair was pulled up to a third side. All of the chairs were facing a laptop monitor. Lopez motioned me to sit in the third chair and focus on the laptop. I noticed that Cruz was now in some sort of khaki army uniform, his shoulders bursting with gold stars.
We watched the scenes being shown on the laptop for several minutes without anyone saying anything: Cruz fucking me in the pool; me fucking Manuel on a bed; Lopez and Cruz fucking me on another bed.
After the show had gotten into the third scene, I said, “So?”
“So, Chaz,” Lopez said, “Daniel here isn’t really Daniel. He’s a general in the Cuban intelligence service. What do you think about that?”
“I’m flattered,” I said. “I didn’t think I’d rate more than a colonel.”
“You seem awfully cool, Chaz–if that’s your name,” Lopez said, with some irritation in his voice. “Do you understand what sort of bind you’re in now? We know you are CIA. The CIA doesn’t exactly approve of their employees engaging in activities like these videos show. Look at that poor young man, Manuel. Why it looks like you’re raping the young man. He may not even be a young man to someone watching the tape and being told he isn’t. He may be just a boy.”
“So, all of this is about blackmail?” I asked.
“It would seem so,” Lopez answered. The general gave a snort. “What we would like for you to do is to work for us–for Cuba. That doesn’t seem to be asking for much to not share these tapes with your employers.”
“Is that it?” I asked, standing. “Tell me, how much does Manuel know about his part in this?”
“What do you think?” the general responded and gave another snort.
So, Lopez, who I thought might be an Argentine, was Cuban, and Manuel, who I thought might be Brazilian, might be Cuban. And the Cuban general I never gave a thought to in origin definitely was Cuban. Wonderful.
I got to the door to the foyer, and they both started to rise to, I don’t know, follow me? Restrain me? Shoot me? Fuck me again? I didn’t wait to hear. I stopped them momentarily by saying, “I suppose I’m not going to get the $500 you promised me either.”
They looked at each other and laughed. “No, Chaz, you aren’t getting the $500 I promised you,” Lopez said and then he turned his head to me, but I was already gone, making a dash for the door.
I had the front door open before they came out of the library. The general was unbuckling the gun holster under his arm.
“Before you think of doing that, general, you might take a look out front. It’s just a guess, but I’ll bet you didn’t enter the country legally. That thing that looks like a derelict barge off the coast? Is that your yacht by any chance?”
Men in black were coming in as I was leaving. “I was a bit ahead of you, Hector,” I said before I turned and left. “I called my guys on Thursday, and they hightailed it down here to join the party.” I didn’t bother to tell the Cubans that Langley wouldn’t give a shit about any sex tapes they saw on me. That was my job at Langley–creating sex that looked good on tape. I’d let the two Cuban spies contemplate that one while they sat in a U.S. prison cell.
The next night, I heard the buzzer to my apartment go off down in the street and took a few minutes to prepare as I saw Manuel’s mug in the street door camera shot.
I watched from the landing as he wound around on the stairs and landing up to the fourth floor. We’d done this before–in more happy circumstances. They certainly were more innocent circumstances on my part.
He was trembling when he entered the apartment and went directly on his knees in front of me. What could I do? I let him suck me hard and then I took him into my bedroom and fucked the stuffing out of him. It seemed to be what he wanted. It certainly felt good to me.
As we lay there afterward, he gave me an innocent little look with his eyes and said, “You’ll have to help me. The Cubans will be after me. They’ll say I informed you. They used me, and I didn’t know what they were doing.”
He’d just done the innocent, open and vulnerable virgin performance for me again that he was so good at. I enjoyed it immensely.
I called out that we were ready, and two agents dressed in black entered the bedroom. I’d ushered them in there when I’d seen that it was Manuel who had buzzed from the street.
“These men will give you protection,” Manuel. “They’ll take you somewhere. They’ll ask you questions. You’ll be safe with them one way or the other. What eventually happens with you is probably up to how good and convincing you are with your answers.”
He was still bombarding me with innocent sheep eyes when the two agents were taking him downstairs. I sort of regretted seeing him go. You don’t often come up against a sugar-coated hot pepper like him. I, in fact, liked him so much and wanted to believe him so much that I’d go check out the next day if he really was enrolled at the Key West College of Yoga in India. If so, I’d continue to check from there. If not, well . . .
That left Sam Winterberry who then entered the living room from the spare bedroom.
“I think you’re safe enough here, Clint,” he said–Clint being my name of the post-Cuban general caper operations. “But if you want, I could pull you back to Washington now.”
“No, thank you,” I said. “I rather like it here in Key West.” I was already thinking about the café on DuVal Street and how I was going to snarf up a table for two the next time I was there when the café was otherwise jammed. “And you,” I said. “You starting back to Washington now?”
“No, I think I’ll stay here for at least the night. In your bed . . . with you.” He gave me a pointed look.
“Yeah, I think I’d like that,” I answered. And I certainly did.
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