Becoming Key West

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.