“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 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 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 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.
“Thanks, man. Great ride,” he said, as he got in the car. Another frosted blond with rings in his nipples and right ear. But this one was athletic in body build. He was admiring the red ’66 T-bird convertible, even after he got in, running his hands over the top of the door frame and the dash on his side, and turning around to look at the back. “A convertible with a backseat. Neat. Bet you get a lot of use out of that.”
“Sometimes I forget it’s back there,” I answered, not sure what to say. The car was mine. When I was in it I was behind the wheel, not in the backseat.
“I’m Tag,” he said, as I got started down the road.
“Tag?”
“Yeah, as in ‘Tag, you’re it.’” He laughed. I smiled, not getting it. “Tag is a word down here for being fucked,” he added.
“Where you going, Tag?” I asked, ignoring his last explanation.
“Wherever you take me,” he answered. But then, when I turned my head and gave him a quizzical look, he added, “You picked me up to fuck me, didn’t you?”
“No, what gave you that idea?” I asked, shocked. “I picked you up because it was a long walk from where you were to anywhere.”
“You are a top, aren’t you? I saw you the other night–in the Wave bar. You left with Cory. So, you’re a top, aren’t you? And a real stud of one even if you don’t dress Key West. Not long here, are you?”
“No, I haven’t been here long,” I answered. I glanced over at him and almost drove the car off the road. He had the waistband of his Speedo pulled down under his balls and was stroking his cock. “Where did you say you wanted to be dropped off?” I asked again, pretending I couldn’t see what he was doing.
“The backseat of this car would be nice,” he answered. “I asked if you were a top. I think you are. You’re a real stud. If you went with Cory, you must be a top. If you’re a top you could tag me. Get it now? And you wouldn’t have to pay for it like Cory made you do, I’m sure. You’re too stud looking to have to pay for it in Key West.”
“Yes, I’m a top,” I said, wearily.
“You get a lot of tail here in Key West? You look like you do.”
“Not so much,” I answered.
“You need to signal it.”
“What do you mean, signal it?”
“See, I’ve got a ring in my right ear. That means I take cock. You need to put one in your left ear–and maybe dress down more, to show the goods better. Then you’d get all the tail you could handle. I bet you’ve got a nice package. Yes, you do.”
He had his hand on my crotch.
“Don’t do that. I’m driving.”
“Then pull over somewhere. Holy, Jesus, you got a whopper!” He’d unzipped me and pulled my cock out. I hardened in his hand.
“Hey, you’ll run me off the road. Oh, shit, oh fuck!” He had his mouth on it. I pulled over into one of the parking strips by a beach and leaned back in the seat, groaning, as he gave me head.
“There’s a beach a mile down the road with off-road parking, under some palm trees. That’s where I want you to take me,” he said when he came up for air. “I want to see if I can take this honking big cock–in the backseat.”
I had to push the passenger side of the front seat up as far as it could go for me to fit in the rounded corner of the backseat with Tag sitting on my cock. I positioned him facing me, and kissing me as he fucked himself. Guys were coming up from the beach–all cut, blond hunks–and gathering around to watch us fuck and to run their hands over the finish of the T-Bird. I think the interest was divided between watching Tag, crouched over my hips, rising and falling on my cock, while we kissed, his arms around my neck, while I grasped his waist and helped guide the fuck and the attraction of the red T-Bird. The interest seemed to shift to me, though, when Tag came all of the way off my cock a couple of times to show how long and thick it was. Then several were muttering that they wanted to get in on the action. By the time I shot my load, three guys had sat in my lap and risen and fallen on the cock and a couple had begged me to take them home and bang them properly.
Looking around afterward, I wasn’t able to pick out which one was Tag–they all were blond, cut, athletic hunks.
Welcome to the Key West lifestyle. For the first time I thought of the groceries in the trunk, many of which would be ruined now. I’d have to go back to the store.
But first–a couple of the cut blonds wouldn’t leave. They said they wanted me to do them on the beach. So, what the hell, I went down on the beach with them and banged them properly, one after the other. I wasn’t sure, but one of them could have been Tag. It suddenly occurred to me what he’d meant about being tagged.
I was starting to get used to the Key West lifestyle. I’d have to get me one of those earrings in my left ear.
* * * *
“Will you have any more soon?”
“I don’t have any; not for a while,” I answered, my mind on how I was going to have to ratchet back on these paintings because my stepson Billie was visiting on spring break from the University of Maryland and was bringing a friend. I’d gone wild in recent weeks, picked up the Key West spirit in spades. Too wild. I probably needed to ratchet back even if Billie and friend weren’t visiting. The paintings and charcoal sketches I’d brought to the gallery today were more because I needed to get them out of the house.
“They sell really well,” the gallery owner said.
“That could only happen in Key West,” I said, with a laugh.
“No, there’s a market for explicit gay art many other places,” the gallery owner answered. “Perhaps it’s just kept in a back, back room rather than here, where it’s only in the back room, and the door to the back room is open. Your paintings are scintillating. So realistic. Just like you were there.”
Real, not realistic, I thought. Some of it, I had to believe, thanks to the quick recognition my new earring in the left ear had brought me. No more speculation in bars.
I turned to look at what I had brought today. A dance scene at the bar. Young men gyrating and flirting. The spotlight on one young Jamaican, with his dreadlocks thrashing about his head, down on the small of his back on the dance floor boards, holding his ankles, obviously doing a spin, his face joyous, the other dancers swirling around him. Very sexy, the gallery owner had said. Even though it wasn’t the usual sort of the art I was selling through the gallery, he said he knew who would snap it up. I knew too. It was the same man who had bought the companion piece a couple of weeks before–of the same Jamaican, on his back, holding his ankles, his legs spread, his dreadlocks fanned out over the floor, perhaps on the same dance floor. But naked, his long, black cock laying up on his belly, a dribble of cum at the head. His hole exposed, reamed wide, cum flowing from the opening.
That painting had lodged itself in my mind, right after I had pulled away from dropping my load in the Jamaican, who was lying on the small of his back on a cube in a back room of the bar and holding his legs open for me.
And the second painting, of a young, dark-haired man, with black lipstick, on his back, lengthwise, on the top of a bar–the very bar where he was a bartender–his legs spread and bent, his back arched, a dreamy, but slightly pained expression on his face, his hole gaping wide and bubbling over with cum. The expression of totally, over-the-top fucked.
“All three will go fast,” the gallery owner said, reaching for the third one I was still gripping in my hand. “That one’s unusual, but very nice.”
“I’ve decided I’ll keep this one for a while,” I said, looking down at the painting of a man’s muscular torso–Roman style, in that the arms are raised, but stop at the biceps, and the meaty thighs end at midpoint. The torso is twisted a bit to one side. It’s not the torso of a young man. A man in his late thirties or forties–although I knew it to be precisely thirty-nine. Very well muscled. And if it weren’t for the tattooing across his chest, the viewer’s eye would inevitably go to–and remain at–the long, thick, uncut cock and drooping ball sac with the two large, distinct balls weighing it down. The tattooing was distinctive enough to arrest the attention, though. Red roses, backed by green leaves, in a V, the long upper edge extending along the top of the bulge of the pecs, and then coming down between the pecs in a V. One isolated rose teased the side of the belly button. A startling feature was that the roses surrounded, but didn’t come within a half inch of the taut nipples and nickel-sized aureoles.
“Sexy, very sexy indeed,” the gallery owner said.
“Thanks,” I said. “I’ve got to go now, though. I have an appointment.”
Carefully covering and returning the painting to the trunk of the T-Bird, I drove three blocks and parked in front of the tattoo parlor.
“There, one last rose to fill in,” the tattoo artists said. “Hold still.”
“You hold still,” I said.
“It’s hard to. You’re in deep and throbbing,” he answered, with a moan.
I was reclined back in something like a barber’s chair, naked. Tony, the tattoo artist, also naked, was saddled on my cock and leaning over my chest, filling in the last of the roses on my chest tattoo.
“Oh, Christ, you are so huge,” he whined. “I can’t . . . I’ll have to finish this later. Now. NOW!”
Rising out of the chair as he set the drill aside, I pushed him down on the floor in front of the chair, taking up a nearby chair cushion as I did so, and putting it under the small of his back. The young man was covered in a riot of tattoos, nearly every inch of him covered, other than the tops of his inner thighs, his shaved groin, and a few inches surrounding his puckered hole. Using the unshaved area as a target, I thrust inside him and started to pump as he arched his back, and cried out to the ceiling of the small, cluttered tattoo shop. His tattoos rippled, his own body undulating, as I fucked him.
“Oh, God, you’re splitting me.” And I almost did, taking him hard and deep, but pulling out to the surface to blast his hole with cum.
I already was posing my next painting–when I could get around to doing it. The first one with an external hint of a partner, I thought. The tattoo artist, sprawled out on the floor, his body rampant with color, his arms stretched out in a cruciform pose of surrender, of execution even, one leg bent, the gaping hole, slathered in cum, prominent, raised on the chair cushion, the other leg coming up and toward the viewer of the canvas. And the new touch–a hand, my hand, gripping the man’s ankle, holding the leg raised and spread.
* * * *
I was padding nervously around the patio. I’d already done twelve laps of the pool so I wouldn’t hear them, but they were still at it when I came out of the pool. I had been determined to cool it when Bill and his friend were here. I’d thought they’d be at the beach most of the time–and they were, I guess–but not all of the time. I’d looked forward to the time to catch up on my commercial art, but all I wanted to do was go into the studio and do the painting of the tattoo artist. No, that was a lie. I wanted to do a painting of Bill’s friend, Danny.
The young man was so luscious–and such a flirt. And a screamer. Bill was fucking him in the guest bedroom now, and Danny was giving a running commentary of how good he was getting it.
They both were athletic hunks. On the lacrosse team at Maryland. Bill was from Karen’s first marriage, and knowing how I would be if she hadn’t bought me and could boss me around, Karen kept Bill off at school during our entire marriage. He had never appealed to me anyway. Too arrogant, too self-confident. And, as I now figured out, another power top. We could never have done it. Well, maybe we could have jacked each other off in frustration of nothing else being appropriate.
But I had never really gotten to know Bill. Karen had kept us apart. From photos, I knew he was a hunk, but no more. So, I didn’t know that when he said he was bringing a friend to take advantage of my living in Florida for their spring break, that he was bringing someone to lie under him. A guy, not a girl.
From the moment, they’d entered the house, though, Danny had flirted with me. A really nice piece he was, too. Greek. Mediterranean dark and sultry.
“Oh, you have an earring,” he said as they entered, “In the left ear.” He said it like he knew that was a raging signal for a top at the time. And, of course it was, which is why, in my going wild, I’d had the piercing done.
“Already gone Key West, Gene?” Bill asked, as he passed me, obviously not caring about my orientation–and quickly, since it wasn’t long before he had Danny on the guest bed, screaming his lungs out–establishing his orientation with me. The arrogant little prick.
I’d already gotten a painting off them, though, cracking the door and seeing them, in my mind’s eye, in a Yin-Yang ball of fuck. I’d done an abstract sketch of them with the dueling cocks being hard to miss by anyone looking for them–and possibly not seen by anyone not looking for them.
I’d done everything I could in the two days they’d been here to lower key myself. I covered the rose tattoo with dark T-shirts, and I wore baggy, knee-length gym shorts. There wasn’t much I could do now about the earring. I just hoped that the meaning of the signaling was local to Key West and not the same up in Maryland. None of that deterred Danny from touching me when and as he could.
Today, I was on my last nerve. I was aroused by their sexing, hard, and frustrated. I dove into the pool again. When I was on my return sixth lap, I came up for air to find Bill standing there.
“I’m going out for smokes and beer. You’re out of beer. I’ll be gone for a while. I think Danny would like to have company.”
Shuddering, I came up out of the water and slowly toweled myself off. I wouldn’t do it. I’d dry off and go to the studio. There were so many commercial art projects that needed attention.
I stood in the guest room doorway, looking at Danny on the bed. He obviously was expecting me. He was on his back, two pillows under the small of his back, his legs spread and bent, his hand stroking his cock, his hole open and glistening with Bill’s cum, pointed at me. His head was propped up on more pillows so that he could clearly see me in the doorway. What was going through my mind was knowing that I could open the hole more for him–that I wanted to.
“Shit, a roses tattoo,” he murmured. “Gorgeous. Sexy. Don’t make me wait. Screw me.”
I pushed my bathing suit down and stepped out of it.
“Oh, holy shit, man. I don’t know. Billie is big. But you’re huge. I don’t know, man. Maybe . . .”
But by then I was on the bed, rising up between his legs, covering him, and lowering my lips to his. I took him into a deep kiss and we rocked back and forth, my cock rubbing up and down his heaving belly. His was moaning and groaning at the decibel rate of a diesel engine, as we rolled around the bed. He locked his arms around my back and his ankles around the small of my back and moved his pelvis hard against mine. Arching his back and crying out, I felt his cum shoot out over my belly. He relaxed his grip and went slack, letting his legs and arms stretch out.
“Sorry,” he whispered. “Did Billie tell you I was a fast shooter.”
“No, he didn’t,” I answered.
“So he didn’t tell you I was a fast reloader too.”
“No, he didn’t. Did he tell you that I could split you apart and that I could fuck you all night? We’re going to make you a bigger hole, Danny.”
“Ulp! Oh, God, Oh holy shit,” he cried out, as I positioned my cock head and started the thick invasion.
“Oh holy shit, oh holy shit. You’re enormous,” Danny screamed, as he grabbed for his ankles and spread and raised his legs wide.
I fucked the shit out of him for a good twenty minutes. By the end he no longer was screaming, he was babbling and moaning softly. He no longer was holding his ankles either. He was a rag doll. I held his ankles while I missionary fucked him. And I held him up with an arm under his waist while I doggy fucked him.
All along I was wondering what painting this would make. When it came to me I hauled him off the bed and over to a straight chair with arms. I hooked one of his legs chair back and let him put the other foot on the floor, with his leg bent. I pushed his head down in front of the chair seat so that he could be looking back at me.
The resulting painting got across how exhausted and fully surrendered he was, his eyes showed how total the fuck had been. And only I knew it, but the cum streaming out of the gaping hole that was the focal point of the painting was from two men.
* * * *
The sun on my body felt good as I lay out on the beach near the airport and luxuriated over my full recovery. I was the only one on this section of the beach between two rock outcroppings that went nearly down to the water. I had been laid up for several weeks. I probably shouldn’t have done it, but I wanted my transformation to Key West style to be complete. This was the life I wanted. I wanted the proper, straight life of Baltimore irrevocably rubbed from my soul.
I’d sent most of the commercial art work projects I had back to the agency in Baltimore to be reassigned. As I owned the agency now, I could do that. I was concentrating on my “after sex” paintings of young men now–not on the collecting of images for a while now, but my mind was spinning more.
I had been dozing–sleeping really–with my arms stretched over my head, when I woke to a rough hand blindfolding me. I tried to pull my arms down, but they had been handcuff over my head and staked. I started to cry out, but a ball gag went into my mouth. My bathing suit was pulled down my legs, and I heard the intake of breath and the word “huge.”
He was sitting on my chest. I knew it was a he, because his cock was thumping against my belly. He was heavy, probably large. The cock rubbing against my belly certainly seemed long and thick.
He grabbed my ankles and jackknifed them up and over my shoulders, rolling my pelvis up. And then for an eternity he was sucking my cock and balls and eating out my asshole. I then was writhing and screaming through the ball gag as he worked his cock inside me–I’d never had a cock, but he certainly seemed huge. I was lying there, panting hard, when it seemed like he was inside me to the root; he was panting too, and I think I heard him mutter, “Tight as a virgin. Love it.” I wanted to scream that I was a virgin to this, but I knew it wouldn’t make any difference to him.
It had hurt like hell. But now that he was in, I could feel my walls stretching to accommodate him. His cock was throbbing, and a certain pleasure mixed in with my pain to realize that I had a man inside me and I’d managed to take him. I always had topped, but I’d often wondered what the bottom felt. Pain, of course, although that was becoming manageable. Something else–the knowledge that I was possessed, that another man was throbbing inside me, had wanted to be inside me, that I was part of an intimate connection–a different part of it than I’d ever been before. In its own way the feeling was exhilarating–arousing.
Could I bottom–well, could I enjoy it? Silly question now. I was bottoming for this man who was assaulting me. And in a perverse way I was giving pleasure through the screen of pain. The pain already was becoming manageable. Bottoms had told me that it could send them on an arousal high, even with a cock as big and all-consuming as mine–as this one was. Whatever, I knew I was fucked now. If he released my arms, I knew I’d grasp him to me, open myself to him as much as I could, and beg for a completion. It was no good wanting any less at this point.
I wondered how it felt to be filled with cum. I knew how I felt when I did it, but how about when another man blasted my insides with hot cum. Did I hope this man would give me that experience? Perhaps I did–if only the pain would go down to a little less.
Without withdrawing from me, he pulled my legs down and hooked my ankles on his shoulders. I felt the ball gag being removed, and I gasped deeply and then worked my jaw to loosen the tight muscles. I couldn’t talk yet. I didn’t know what to say–or to scream. He was inside me already. It’s not like I wasn’t into male-male sex. Just not this end of it. But it certainly was a new experience.
“So, how’s the fantasy so far?” the voice asked–a deep bass voice. He seemed calm, not a wild man at all. “Having a good time?”
“You’re in too deep. Too much pain. Too big,” I whimpered. I didn’t know what else I could say. I couldn’t indignantly tell him he couldn’t fuck me. He already had his cock in me. This was no fantasy; this was real.
“You’re one to talk of big,” he said, with a low chortle. “I’m not anything big like you are. So, too much pain for you? This is your fantasy. We can’t help that.”
“Yes,” I gasped, “too much pain.”
“For now, maybe. There is that better? Play the prostate a while.”
“Yes, better.” He had pulled the bulb back to the prostate. Anything was better, and I could actually feel pleasure creeping in under the pain as his glans rubbed across my prostate, and I felt the cum starting to rise.
“I’m going to fuck you now,” he muttered.
Fuck me now? What was it that he already had been doing? And then I understood. He was beginning to move in and out inside me, pumping my channel. I should know this. I did this to men. The cock was rubbing over and over my prostate, bringing forth flashes of pleasure and the need to shoot. He was stroking inside me, but no deeper than the prostate. I did this to myself sometimes–with the dildo I’d bought on the shop on Duval.
I sighed and trembled in his embrace.
“Like that?” he asked. “Can you manage it better now?”
“Yes,” I murmured. His lips came to mine for a kiss, and I liked that too. I knew he was moving the cock deeper in his stroking, but the pleasure was still slowly washing over the pain. And then a bit faster and deeper. He was pumping my ass, while he stroked my cock with a hand, and he was kissing my lips, and my throat, teething my nipples. I shuddered and felt my pelvis involuntarily going with him. I’d felt this so often with the men I fucked–the point of surrender, of going with the fuck. Of wanting the fuck. And now the pain-pleasure balance was tipping in favor of pleasure. Now is usually when the men I fucked begged for it.
“Yes, yes. please. Work me, fuck me.”
“You want it now, don’t you?”
“Yes, don’t stop. I want to come; I want you to come . . . inside me.”
“I’m in almost as deep as before,” he said. “You want it all?”
“Yes, yes, give it all to me. I can take it.”
And I could. There was pain, but there was pleasure, and I was pulling the pleasure through the wall of pain. Faster, faster came his strokes. Harder, harder he pulled on my cock. And then I ejaculated. And if anything, that made me relax, open more to his cock, and he was fucking me deep, continuing on to his ejaculation. The infusion, the spouting of his seed inside me was an incredible feeling. I wanted the fountaining to go on forever, but of course it lasted only for a few seconds.
I whimpered.
“Liked that?” he asked.
“Yes,” I whispered.
“Want it again?”
“Yes,” I answered before thinking. Wanted the pain of the first invasion again? Not on your life. The feel of his hot cum filling me? Yes.
“In a few minutes,” he whispered.
My answering whimper was probably taken by him as disappointment that he couldn’t fuck me again, right then.
After half of an eternity of being held close with him kissing me and tonguing my throat and chest, he pulled out of me, stood up, and reached down and lifted my legs until I was rolling up onto my shoulder blades. Scissoring my legs, he worked his cock inside my hole again. And then he brought the legs together, holding the ankles together. The cock fit was incredibly tight, but the pain wasn’t anything like it had been before. When he began to pump, I lost it and writhed under him, panting hard, and, to my disgust, my mouth, betraying me as much as my body was, was murmuring, “Yes, yes, fuck me, fuck me, fuck me.” He tensed and then jerked off his load inside me, as I was shooting off as well.
Then he let my legs down, and left me there.
The next I knew, I was being freed and a familiar face appeared above me. “Cory?” I asked, tentatively. “I haven’t seen you–”
“John? I didn’t recognize you at first with the tattoo and earring. And this. When did you get this?”
“The cock ring? The Prince Albert?” I asked. “Weeks ago.” I didn’t mention that I’d had myself circumcised too to show off the PA. It was my way of going “all Key West.”
“I love it. I want to fuck myself on it. But what sort of fix have you got yourself into here?”
“I have no idea. Some mad assaulter. Bound and gagged and fucked.”
“Fucked. You ever been fucked before?”
“No, never.”
“You sore?”
“Yes, of course.”
“A big one?”
“Felt like a baseball bat.”
“So, now you know how a big one feels.”
“Yes, I guess so. Should I be reporting it or something, though?”
“Reporting it? What, you didn’t know this is a Beach Attack hookup spot?”
“A Beach Attack? What’s that?”
“Beach Attack is a Key West sex game–for guys who want to simulate rape–as giver or taker. This is one of the spots they use. Look, you set your towel down in front of that stake up there. If you brush around in the sand there, you’ll find the cuffs that go with it. You put your towel down and laid down right in the spot one does who wants to be bound and taken in a Key West sex game.”
“Oh.” What else could I say? So much still to be learned about the Key West lifestyle.
“You never called for me at the escort service.”
“I didn’t think it would get me anywhere. I took what you said when you left the motel room to be a kiss off.”
“It wasn’t. It was that you just were so big. I couldn’t take my next appointment. It scared me.”
Nothing was said for the next few moments, as he was trying to swallow my cock. I laid back and moaned and listening for the tinkle of the PA on his teeth.
“Mmmm, I like that,” he said, coming up for air.
“But does it still scare you?”
“What do you think?” he answered, as he moved a leg over my midsection, positioned his hole on the cock, slowly sheathed himself, and started to rise and fall on the cock.
“Do you want to see my house,” I murmured later. “And my name isn’t John. It’s Gene.”
“I figured it wasn’t John. Sure, I’d like that. And the paintings. I heard you were doing sex paintings. They’re all the rage.”
* * * *
Cory had been with me for two weeks. He still went out on jobs, and I didn’t stop him–part of my developing Key West lifestyle–but he spent long enough in my bed to keep me happy. Each time in bed, he taught me a new position and I, in turn, was able to pull passion out of him that he said none of his johns did.
Truth be known, I didn’t give up cruising; I went cruising too occasionally, without him. I didn’t bring anyone but him back to my bungalow. I found places to fuck them in place–to keep them at least a heartbeat away from me. I had gone pretty far down the road of “Key Westing,” though: an earring, a big tattoo, a “dirty pictures” job, casual fucking–even my stepson’s boyfriend, circumcision, and a Prince Albert. The truth be known, I even was frosting my hair a bit to add in highlights and using skin cream to try to slow down the inevitable aging. I walked around naked in my home and with just short shorts and flip-flops in public, and I returned flirty stares–even followed them up on occasion far enough to get my dick inside another man.
I still had it–in fact was refining it, thanks to Key West. Once I got my dick inside a man, none complained, and I had more referrals than I could handle.
And I’d even, now, had another man’s dick inside me–and the more and more I thought about it, the more and more I thought I could enjoy that. Was it really all that painful, considering the eventual pleasure? Would it be that painful if I did it again–and again? Was I too chicken to find out? Surely the Key West way would be to go with the flow if the situation naturally presented itself.
So, how was that? In less than six months moving from imposed straight, to power top, to versatile.
When he’d first come into my bungalow, Cory had been awed that so many of the sketches and paintings I had were of him. I fucked him on the floor that afternoon, despite the pain of my own very recent experience, and he reveled in looking around of the artwork featuring him well fucked as I was fucking him well. Then I painted him in the pose I’d left him in when I’d filled his passage with cum. That painting had gone for a pretty penny.
Since that day, I’d ruminated on the fucking I had received for some time, but when Cory came into the studio and looked at what I was working on one afternoon, he said, “That’s you, isn’t it? The gaping hole with the cum dribbling out is your signature, I know, but those legs raised and brought together at the ankles–those are your legs. There’s that birthmark of yours, there, on the thigh.”
“Yes, that painting is of me.”
“You thought much about that fucking you got?”
“A little, I guess.”
He caught me in the lie immediately. “Just a little? A little is enough to weeks later be painting it? Did you like it?”
“I don’t know if ‘like’ is the word I’d use.” I didn’t want to admit that, increasingly, it was the word I thought.
“But you got hard and you jacked your load when he fucked you, didn’t you?”
“Yes. A couple of times.”
“So, you liked it.”
“It was something new, I guess.”
“So, you liked it; you’d do it again.”
“Probably.” That’s as far as I was willing to go–even with myself at this point.
“You want to be fucked again, don’t you?”
“Yes,” I admitted.
“I could arrange that for you. Get any cock size you want. Rough or vanilla. You know this is Key West. You know that anything goes here. If you like it, do it.”
“I’ll keep that in mind. But I hear the doorbell.”
I opened the door to a muscular, bald hunk. A regular Mr. Clean. “Yes?”
“I’m Stan. I’m a fan of your artwork. And I’m the guy who spiked you in the Beach Attack game on the beach near the airport a couple of weeks ago. I followed your T-Bird home. I think you want me again, and I can’t get you out of my mind. Can I come in and fuck you again?”
I lay on my back on the bed, my legs spread and bent, my hands gripping Stan’s biceps as, standing on the floor, leveraging off his feet and leaning into me between my legs, Stan hammered me hard and deep. I was arching my back and crying out, “Yes, yes, fuck me hard!”
There was pain again, but not nearly the pain as before–and more pleasure. The pleasure added of knowing who was fucking me–a big-cocked muscle man. Wanting his dick inside me. Exercising hard to give us both pleasure and release. I was taking him deep. I could handle it. We were one beautiful, synchronized fucking machine.
I’d never known I wanted this too–that I could be versatile. And not just versatile, submissive, and fucked hard.
Cory nudged in between our chests, coaxing Stan to rise up more. The smaller man positioned himself on my cock, and the three of us went to town–Stan pounding me in the ass and Cory riding my cock. As Stan was pumping cum into my channel, I was thinking about how I was going to depict this in art. Probably an abstract that brought you deep into the painting before your blushed and said, “Oh, my, it’s three studs fucking.”
Later, the three of us sitting around the kitchen island, eating sandwiches and drinking beer–all of us knowing we’d soon be doing it again, the telephone rang.
It was Chris from the ad agency in Maryland–my ad agency. The man I’d left in temporary charge.
“When are you coming back, Gene?” he said. “There are decisions to be made up here. The art work is backing out.”
“I don’t think you’d recognize me if I came back, Chris.”
“What? What does that mean?”
“I’ve been fully taken over by the Key West style.” I turned my face toward Stan and winked. He winked back. “I don’t think I could even be allowed to walk the streets of Baltimore now.”
“What are you saying?”
“Send me the paperwork that makes you managing head of the agency. Hire another commercial artist or two. Just send me profit checks. I’m all Key West now.”
I turned to Stan and Cory after disconnecting with Chris and almost did a double take and laughed. The robe Stan was wearing had come open. He was perched on a bar stool and had a hand on his cock, working it up for our next workout in the bedroom. He wasn’t so big. His cock was bigger than Cory’s certainly, but he was no championship stud–not compared to me in any way. I’d felt taxed by a normal-sized cock. God, did I still have a lot to learn and prepare for in the Key West lifestyle.
Oh, well. It was a start. I had time to work my way up. I wondered if Stan had ever been fucked–and by someone as hung as I was.
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