Becoming Key West

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“Are you lookin’ for company, Doll?”

I riled at being called a “doll.” I turned and looked at the bartender who was leaning over the bar and smiling at me. He was a real swisher—wouldn’t have gone out on the street up in Baltimore. But, of course, no one else in this dive would have, except me, I guess. I definitely was out of place in my pressed khakis and sports shirt. Key West was a long way from Baltimore in 1970, and that wasn’t just in miles. I almost wondered how I had gotten here—and why I’d come. Still, behind those black-painted lips, he was good looking. Much too young for what I was looking for, though.

And what was I looking for? Hell if I knew. I just knew that something called me to a place like Key West, suddenly becoming known as a place for a certain kind of person to be, after Karen died. Ten years married to my boss, who insisted that I change my aspect for the allowance to keep coming. Which I did. Ten years straight.

“No, no, thanks,” I said. “I’m meeting someone here.” I almost said “hooking up with someone.” I should have said that. I needed to learn the lingo if I was going to stay here. That “if” was up in the air, though. Maybe Key West was too much, too out there. Maybe after ten years I couldn’t get back on the wagon—or would find I didn’t want to anymore. Good thing I had the bungalow on a six-month rent to purchase.

“You’ve been sittin’ there for a half hour and nursin’ two beers,” the bartender said. “A big, handsome, strappin’ stud like you shouldn’t have to be alone that long in here. that isn’t Key West.”

I smiled wanly at him, and said, “I was early.” And I was, and nervous as hell. And if I’d known I could just walk in here and get it, I wouldn’t have, out of frustration at being here a month and nothing happening, responded to the escort service ad in the underground newspaper. I’d never had to pay for it before in my life. But there are a lot of changes in ten years.

The bartender was probably just jiving me on. I was pushing forty hard. Nearly everyone else in here was half my age. Sure, I’d gotten the eye more than once. But I probably looked like a sugar daddy to them. When I parked the red ’66 T-Bird convertible up on Duval, the car had gotten more notice than I had.

“I take you for a power top, Stud,” the bartender continued. “You don’t see anything else you want to spike in here the next hour, I get off then. I’ll show you a real good time.”

“Umm, thanks, but I think he’s here.” A young guy was at the door, looking around. And he appallingly fit the description. I was hoping not.

“You mean Cory? Yeah, he’ll suck it out of your balls good.” With that and a wave at the young man at the door and a finger point at me, the bartender moved down the bar.

“John?” the young man—maybe too young, I thought, certainly not the twenty-four I’d been told—said as he came up to me.

I wasn’t John, of course, but I had told the escort service I was. Oh, God, why was I paying for this humiliation? He wasn’t anything like I would want to fuck. Not that he wasn’t good looking and trim. He was—but in a cute way. When I was going with men, I was going with men men. And he too couldn’t have walked the streets of Baltimore in 1970. He was small, short, and thin, showily dressed as the whore he was—tight micro shorts, a mesh T-shirt—a sleeve tattoo covering his right arm, rampant in color. And the piercings. An eyebrow, the right ear—and I’d been told what that meant—and, I could see through the mesh of his shirt, both nipples and his belly button. Who knows where else? His hair was spiked and frosted. He screamed bent-wrist homo. He looked a lot like many of the young guys on the dance floor in this bar. The Key West lifestyle, apparently.

And surely he wasn’t legal. I needed to end this. This was a terrible idea. I needed to bow out, get back to the bungalow, pack up my artist supplies, and run back to Baltimore. I owned the advertising agency now—by way of Karen’s death; she’d been twenty-five years older than I was; bought as her boy toy—I wasn’t just one of its commercial artists anymore. Why had I felt I could be freer now, could get back on the wagon?

He came in close to me, between my knees as I swiveled the bar stool toward him. His eyes were a rich, chocolate brown and drew me in. Without saying anything he unbuttoned the top two buttons of my shirt and ran a hand in to palm a pec. “My, you’re a big handsome one, aren’t you? Hard pecs. Spend most of your day in a gym?”

“Listen, maybe this wasn’t . . .” I gave a little jerk. His other hand was cupping my package, rubbing. I immediately responded.

“Big and handsome, with an emphasis on big,” he said in a low, sexy voice. The hand came off my chest and he took a swig of my beer.

“Listen,” I said again. “This might have been a mistake. I haven’t . . . in ten years.”

“It’s like riding a bicycle, Stud. Where are you fucking me? Here, in back? They’ve got rooms. On the beach? Backseat of a car.” He later told me he’d rushed me bahis siteleri for fear I didn’t have to pay for it—that half the guys in the bar would have gone with someone looking like me for free.

“Oh, God, not here,” I exclaimed, looking around at all of the gyrating bodies, with the loud noise. No room in back could get away from this. This wouldn’t happen in Baltimore in 1970. “I booked a room in a motel around the corner, but . . .” He dragged me off the barstool.

“Let’s go then.”

* * * *

He was right. It was like riding a bicycle.

He was as light as air, and pliable, and flexible. I was up on my knees on the bed, with him draped on my front, one of my hands cupping his chin, holding the back of his head into my chest, nestled between my pecs. My other hand was on his lower belly, pressing in with each thrust up his ass to give it to him deep. His legs were streaming back from us, against my calves. One of his arms was thrown up and back, his hand gripping the back of my neck. He was jacking himself off with his other hand.

“Shit, you’re gigantic. You’re killing me!” he cried out.

“Slow down? Stop?” I queried, still nervous, not believing I actually was doing this.

“No man, I was just giving you the Good Housekeeping seal of approval. Give it to me deep. Biggest I’ve had. Fuck me hard.”

I’m sure he said this to all the johns—I almost choked when it reminded me of the name I’d given him—but I was big and knew I was. In my earlier life I’d reamed many a young man a wider channel. I was surprised I wasn’t doing it for Cory. He was so small and thin. And his cock was small. It was like fucking him was a sin. But other than the initial difficulty of penetration, he’d opened right up, sucked my cock right in, saying he wanted it, wanted it bad.

“Shit, man. Harder! Deeper! Faster!”

I lost all control and began to pump him hard, with him flopping around on my torso, held in check only by my strong embrace, I turned my face down toward his to find he was looking up at me with wild, needy eyes. We went into a deep kiss, he shot his load across the sheets, and I unloaded mine deep in his ass.

When I’d parked in front of the motel room, he’d said he didn’t want to get out of the T-Bird yet. He’d bent over me, unzipped me, marveled at the size of my dick as he uncoiled it. The first thing he did with it was to pull the foreskin down to the bottom rim of the bulb, which got a groan and my attention real fast. I groaned again when he thumbed the now-exposed piss slit. And then it was like he was worshipping it, as he fondled and stroked it until it was hard and throbbing. Nervous and naïve about relating to a rent-boy, not to mention having my cock worked in the front seat of a top-down convertible in front of a line of motel rooms, I just dumbly looked down at the hand manipulating my cock. I gave a little jerk as he tried to work the tip of his index finger into my piss slit and his efforts were rewarded with a dab of precum, which he slathered around on the bulb of my cock.

Afraid that I’d fire off too fast, I had to arch my head back on the top of the seat, stretch my arms down the back of my seat, and think other thoughts—about the art spread I should be home painting even now, with a deadline looming. I groaned as his moist lips opened over my hard dick and he sucked on the head. My cock was hard, hard, hard and throbbing, and he tried valiantly to deep throat it, not being able to but coming close. I grunted my need and set my hips in motion, at first tentative rises, moving to strong upward thrusts, as he made a big, stationary O of his mouth and let me face fuck him. My hands went to the back of his head, pushing the head down as I thrust up. He was gagging, but going with it, and now he was deep-throating, his lips reaching into my pubes. Now . . . when . . . with a jerk and another and another and a deep sigh, I creamed his tonsils.

He sat up in the seat, wiping his mouth off with the back of his hand, and said simply, “God, it’s big. They should mold a dildo off that.”

Overwhelmed, I reached for him, pulling his face to mine with a hand cupping the back of his neck, and took him into a long, deep kiss, a kiss tasting salty—of my cum. This is something I most certainly would not have done in Baltimore. I was almost taken aback that I was doing this here, but then I reasoned that he was a rent-boy. I was paying good money for this. Ten years earlier I’d never have thought of paying for it. But payment deserved good service. It should put me in control.

My other hand fiddled around with the buttons on his shorts fly, flared the sides open, found his cock, and, as we continued in one, long, drawn-out kiss, I jacked him off. His cock was small but filled out pretty well when stroked.

When he’d shot off, I pulled away from him, still cupping the back of his head. His eyes had a dreamy expression. I didn’t know if that was something he’d trained himself to do for a john or not. Probably so. Still, it was sexy canlı bahis siteleri as hell. All of his paint and hardware were evaporating in my mind. I was seeing through to a desirable young man I very much wanted to fuck.

“Shit, man. No one’s done that for me before. That was good.” He sounded genuine, but who knows?

“Is this it, then?” I ask. “I give you your money now, and you split?” If it was, it was worth it—after ten years of pretending straight.

“You haven’t fucked me. You’re paying to fuck me. You said you had a room. I’ll go in with you . . . if you want. If you really do have a room.”

He dozed after I fucked him, draped on the front of me. When we’d ejaculated, I’d released him and let him fall to the bed, and he’d propelled himself up to where he was stretched out on his belly. He turned his face up to me, whispered, “God, you’re built big. I took a big one,” and closed his eyes.

I leaned over and ran my hand down the crevice between his butt cheeks. I followed with the other hand and spread the cheeks apart. For some reason I wanted to see my cum dribbling out of his hole—some sort of affirmation that I’d put it there. The hole hadn’t closed; it was wide open in a big O shape, a couple of inches of pink, still rippling passage wall visible, leading down into the depths of him. And the cum was more than a dribble and glistened, caught in the beam of the light over the bed. Cory sighed and stirred, but he didn’t wake. I resisted the urge to mount him again, but I wasn’t ready yet. I wasn’t hard enough.

Ten years without, and there, see, I reamed that hole. I put that cum in that hole. Just like riding a bike. Back in the saddle again. Even if I had to pay for it.

Taking my hands away, I sat there at the end of the bed, cross-legged, and watched him snooze. I’d done it. When I was hard, maybe I’d do it again. After ten years I’d fallen off the “straight” wagon. Of course I’d had to pay for it, and he wasn’t anything I would have picked. I’d always gone for the college preppy or athletic types. Clean cut. And bigger. Someone closer to my own size. A football or basketball player. Someone who could hold his own. Not like Cory, who I’d manipulated at will. I had trapped his small, thin body in my arms, stuffed his ass, and fucked the shit out of him.

Why was it I felt so satisfied, so powerful, so aroused . . . still? What had I paid for? I thought, as I felt myself going hard again. How many times? Could I remember? I padded out of the bed and over to my trousers. Taking two more twenties out of my wallet, I dropped them on top of what I’d put on the dresser, for him to see, before we’d undressed—me nervously so.

While I was up, I looked around frantically for something to sketch on. That’s what I did. I was an artist. Nothing like I wanted to sketch now, but this was now, here. I found a couple of pieces of motel stationary and a pencil by the telephone. A Gideon’s Bible in the nightstand.

After fifteen minutes I had captured him, stretched out on his belly, in repose. But as I finished the sketch, my hands were shaky. Having him in a sketch wasn’t enough. I had to have him again, totally.

His eyes shot open and he grunted and groaned, as, stiff-armed above and stretched out over him in a pushup position, I penetrated his ass and slid in deep before starting to pump.

Murmuring, “Shit, it’s big. Gigantic,” he sleepily spread his legs, rose on his knees, reached under to grasp his cock, and began to meet the rhythm of my thrusts with counterthrusts of his own. “Fuck, it’s big. Yes, Yes, like that. Harder. Deeper. FUCK ME!”

The headboard began to rock against the wall, the springs of the bed were squeaking. After ten years I was doing a second—fucking a sweet little honey hard.

I lay on my back on the bed, propped up against the headboard, my legs crossed, and my uncut cock in “big slab of meat” repose across one of my thighs. I was smoking a cigarette and watching Cory move around the room, fidgeting with his hair in the bathroom mirror, finding and pulling on his clothes.

I looked down the line of my body. It was still half hard, despite my age. And well muscled. My dick, serviced and satisfied, but laying, docilely across my thigh—not so docile, though, as the more Cory flitted around in the altogether, the more the “big guy” was stirring. My balls, heavy and drained—also satisfied and aching a bit streamed out from under the root of my cock. My bush, strawberry blond, redder than what was on my head, chest, and arms would have to be trimmed now, I thought, if I was getting back on this wagon. My dick looked even bigger with a trimmed bush, and I’d let mine go unruly.

I was fairly purring my satisfaction.

“What’s this then?” Cory asked, picking up the sketch. “This is me.”

“Yes, yes, it is. That’s what I do. I’m an artist.”

“This is good, man.”

“You can keep it. I have you in my brain now. I don’t need it. And speaking of that, if I call the escort service, can I have canlı bahis you again?”

“Have me again, as in fuck the wadding out of me?”

“Yes, if I call your pimp again, can I fuck you again? Screw you? Spike you? Ream you? Nail you?” Why is it that everything in Key West had to be stated so baldly?

“Yeah, I guess,” he said, already at the door, his hand on the handle. “That’s what the agency is for. But I don’t know if you’d get me. I’m thinking of leaving town.”

“Uh, OK,” I said to the door closing behind him. I guess I knew what that meant. Not as much the stud with him as he had been letting on. Well, I’d been telling myself that all along. He was just a whore. He told me what I wanted to hear.

Deflated, I punched out my cigarette in the ashtray on the nightstand, rose from the bed that didn’t seem as much the bed of roses now that it had ten minutes before, dressed, and drove back to the bungalow. Parking in the two-car carport stretching across the front of the lot, I walked back along the sidewalk running down the side of a long, narrow exercise pool, on one side, and the guest bedroom on the other. I entered the combination living room, dining room, and kitchen overlooking the end of the pool and a small terrace backed by an edge of luxuriant tropical foliage and back to the room behind the kitchen that I had set up as my art studio. The master bedroom was beside that, looking out over the terrace and the end of the pool. All in all it was a good house setup for me, I thought.

It wasn’t even midnight yet, and I worked best late. I stood in front of a blank canvas, turning my mind—or so I thought—on the ad campaign artwork that needed to be done by the next Tuesday.

So, how did it really go? I wondered. That first time after ten years. The man sex I had come to Key West to pursue—that I couldn’t have done in the world I’d lived in in Baltimore for the past ten year.

The sex had been good. Incredible—at least the part of getting my rocks off. Even ten years ago I hadn’t often fucked a guy twice, back to back—let alone with a blow job session up front. My balls were drained, my dick very pleased with itself. I relived in my mind the moaning of the little piece I’d fucked—and how often he’d told me how big I was. The blow job was the greatest. I’d rarely gotten that even before Karen’s dictum—I certainly didn’t get them from Karen. In the early days it had mainly been jacking each other off and on to the main event.

But not my type at all. All those piercings. Everywhere, even in his taint, I’d found. Of course, the response I’d gotten by teething or pulling on those was interesting. The flaming-statement hair. The small cock and balls—the small size of him altogether—other than the hole that opened for me. Well, the size had turned me on, especially when combined with the opening of his ass. Being a lot bigger than him—everywhere—and the feeling of overpowering him. Watching what I was packing penetrate him. That had been arousing. It was arousing now. I was hard again.

I looked up at the canvas, ready to start painting. But, to my shock, I’d already filled the canvas with paint. How long had I been ruminating? What had I painted?

It wasn’t anything to do with the ad agency. It was obscene, pornographic. Luscious, arousing. I set the paint brush down and cupped my hard cock. I was naked. That was no surprise, I often painted naked late at night. But I was in throbbing erection.

The painting was of Cory, but in no pose I remembered from earlier in the night. He was on a bed, on his belly, but raised on an elbow, looking directly into the viewer’s eyes, his eyes swimming in satisfaction, fulfillment, cum. The body was small and thin, but beautiful, sexy even with every piercing and the sleeve tattoo in place. His far leg was stretched out, almost straight, the near one bent, covering any sign of a dick. The buttocks were two perfect pert globes, but they were jutted a bit up and parted—parted enough that his asshole was evident—and prominent—open wide and puckered. I had painted globes of white cum dribbling down from the hole.

It was a Cory who had just been royally, satisfyingly fucked. The look in his eyes affirmed that.

I stumbled back, falling into a canvas chair. My eyes glued to the canvas—to the gaping hole with the cum dribbling down—to my cum and the hole I had reamed big. I cupped and squeezed my balls with one hand, and with the other, I pushed the foreskin of my penis to below the rim of the bulb and pressed my index finger into the piss slit, producing both precum and a groan. I then masturbated my throbbing dick to a high-arcing ejaculation.

* * * *

Key West is a small island. Still, it seemed rather a long drive along the Atlantic coast of the key from my bungalow in the historical district to a grocery store. I had rounded the curve on the northern end of the key, by the airport runways, when I came upon a cut, blond hunk in just a low-slung Speedo and flip-flops bumming a ride. Nothing strange in a cut, blond hunk sighting in Key West, but there was nothing out here but scrub and runway to the right and sand and sea to the left. It was going to be a long walk for him. So, I stopped beyond him and let him walk to me.

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