Becoming Key West

"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.