Key West Boy - Cover

Key West Boy

by ChrisCross

Copyright© 2022 by ChrisCross

Erotica Sex Story: What could beat, in risk avoidance, if you have a fetish for fourteen-year-old boys, a scheme of arranging a hookup on Key West in the shore time of a Caribbean cruise port call—arranging a hookup on board, making the hookup after getting off the ship, and getting back on the ship and sailing away after humping the boy in a seedy motel? What possibly could spoil that?

Caution: This Erotica Sex Story contains strong sexual content, including Ma/mt   Consensual   Reluctant   Gay   Fiction   Crime   Rough   Anal Sex   Analingus   Cream Pie   First   Fisting   Oral Sex   Petting   Safe Sex   Prostitution   .

“I’m lost. Where are we?”

Alan didn’t answer.

In the bowels of the cruise ship steaming toward Key West in the Caribbean, Alan placed a hand on the sixteen-year-old boy’s shoulder, psychologically holding him in place while the man fumbled in his shirt pocket for the key card to his interior cabin. This was no time to lose the kid. They’d been flirting with each other for three days across the Caribbean and had finally met at the pool without the boy’s parents around. The boy was a sweet little brown guy with light brown hair. His father was a big black bruiser and his mother a tiny blond. Both had gone everywhere with a drink in their hand, giving the boy, who had a roving eye, little attention.

The boy had been craving attention and Alan had given that to him. Now he was going to give him more intense attention.

It was easy pickings for Alan, in his late thirties, a bodybuilder with a movie star’s face and able to get a smile out of a fence post.

They’d descended five levels in the ship from the pool area in flip-flops, the boy wearing just a skimpy Speedo with a towel over his shoulder and Alan in a Speedo, with a plain blue cotton button-down shirt over it. He usually wore flamboyant Hawaiian-patterned shirts on board to gain attention, but that was exactly why he hadn’t worn one to the pool. He’d seen the parents separate from the boy and had come back to his cabin to dress more “not memorable” for the final move of cutting the boy out from the crowd and getting him alone somewhere quite privately. Alan could afford better shipboard accommodations, but he liked the thought of using a dimly lit interior cabin in the bowels of the ship.

“You sure your parents won’t miss you?” he asked as the door to the dark cabin opened, he palmed the nice little piece’s ass, and gently propelled him into the darkness.

“The casino’s open. They’ll be in there for hours. They’re both already drunk anyway. My mom said she’d burn if she came anywhere close to the ship’s pool. No, I don’t think they’ll miss me for some time.”

“And you won’t mention this to anyone, no matter what?”

“Of course not. My dad’s violent. He’d kill me—literally. He doesn’t understand where I’m at—what my urges are. It’s dark in here.”

“Do you want to do it in the dark, or do you want all lights? And there’s a mirror I can pull off the back of the closet door. I can set it so you can watch me doing you. What do you want?”

Alan had pulled the boy into him, both standing, at the foot of the bed, which took up much of the interior, single-passenger cabin. He was embracing the boy, who was a good half-foot shorter than he was with one arm around his shoulders and the hand of the other one buried down the back of the boy’s Speedo. He had an index finger already digging for—and finding—the boy’s hole. The boy was trembling and rising on his tip toes, the finger invading his ass coaxing him to rise to the man. He could feel Alan’s hard shaft pressing into his belly.

Alan kissed him in the throat. He felt reluctance—and reality—setting in. Maybe the little fucker had been all flirt and no go. “Maybe you’d like mostly dark. I could just turn the nightlight on in the bathroom.”

“Yes ... that would be good ... thanks.”

“Here. Sit here on the bed.”

There was an audible sigh from the kid when Alan released him. He sank down on the foot of the bed, while Alan, unbuttoning and taking his shirt off, went into the bathroom and turned on the nightlight. Leaving the door open to let some light in, he walked around the bed to the nightstand, took a couple of condom packets and a small tube of lube out, and put them on the nightstand. His wallet was in there too and he extracted two fifty-dollar bills and placed them on the nightstand as well.

“We agreed on a hundred,” he said, gesturing to it, and making sure the kid saw the rubbers and lube too. No surprises. He wanted the kid to be fully aware of what he was selling to Alan and what was involved in Alan getting what he wanted.

The boy just nodded.

“How old did you say you were?” If the boy didn’t want to do this, this was the time for them to break off.

“Sixteen.”

“Sweet.” It wasn’t optimum. Alan liked them more like fourteen, young and impressionable, fresh and yielding. Supple and smooth, just now starting to develop into men. Ripe.

“And of course you’ve done it before.”

There was a pause while the boy contemplated whether to lie or not. “No. No, I haven’t. Don’t’ be rough with me. Please, go slow. Fuck you’re big. I don’t think I can—”

The boy had just noticed in the dimness of the light that Alan had pulled off his Speedo and was in full erection. He was fisting his cock and slowly stroking it. “Yes, yes, I’m big. You can. You will. We’ll do this.”

Shit. Fuck. At the same time hallelujah. His first time. Pulling down a virgin. Popping a male cherry. No way the kid was going to get out of here unfucked now.

“Well, sure. I’ll treat you right. You’ll love it. The first time will hurt a little, I’m sure you know that. As you said, I’m big. But the second time. The second time will be heaven. After me, your boyfriends will be a piece of cake.”

“The second time?” the kid squeaked.

Alan could hear the fear and hesitation in his voice. Better get on with it. Picking up one of the condom packets and the tube of lube, he came around to the end of the bed, dropped the items on the bed next to the kid’s hip and leaned down. He cupped the boy’s head with one hand, bringing their lips together, and glided the other one down the boy’s shuddering chest and under the waistband of the boy’s Speedo, quickly taking possession of the boy’s cock and balls and fondling them.

“Lay back and enjoy,” he murmured, briefly pulling away from the controlling kiss. “I’ll take good care of you.”

Returning to the lip lock and gripping the boy’s privates loosely but with control, Alan reclined the boy onto the bed and slowly worked him, waiting for the boy to relax and collapse under him. The sustained deep kiss prevented any further “should we?” or “will we?” discussion.

The boy was overwhelmed, not resisting, completely numb to any defensive motions—just the way Alan wanted him. He extracted his hand from the boy’s package and turned him over, belly down on the bed. As he did so, the boy gave him a panicked look with his eyes, but he didn’t resist. Alan pulled the boy’s Speedo down and off his legs, running his hands, slowly, back up his legs and spreading his legs a bit. The boy was panting and whimpering a bit. He let out a little yelp when, going down on his knees on the floor behind the boy, Alan grasped the kid’s buttocks, spread and separated them, and buried his face in his crack.

The boy moaned, his body shimmering and undulating under the man as Alan held his hips between his hands and ate his ass out.

He was trembling and panting and whispering “please, please,” over and over again as Alan stood behind him, smoothed on the condom, and lubed it up—and then lubed up the boy’s puckering hole with his fingers as well. The fingers did more than lube the boy. Alan pressed the fist of the other hand into the small of the boy’s back and worked the hole open with his fingers.

“Shit, you’re tight,” he muttered, adding in his own mind that it was just the way he liked his boys.

The boy let out a sob and babbled something incomprehensible in response.

But Alan didn’t need anything from the boy now except for a passage that would stretch to his need and lying there, docile, taking it. He was no longer a boy. He was a virginal hole to be breached, a passage to be stretched and filled, the vessel for Alan’s seed, a notch to be carved on the bedpost of Alan’s sexual experiences.

He put himself in position, mounted the boy’s ass, and as the boy writhed and panted and cried out underneath him, did what needed to be done. The saddling took time and effort, but once buried, Alan leaned over the boy’s smooth-skinned shimmering body, pressed his fists into where the boy’s arms meant his shoulder blades to keep him in place, and set up the initially slow and shallow rhythm to increasingly vigorous deep thrusts of the boy’s first fuck.

After he’d shot his load into the bulb of the condom, Alan lowered his body on the back of the boy and kissed him on the back of the neck. He let his hands roam the boy’s supple body. The boy didn’t respond. He was somewhere else altogether, realizing that he now never could come back.

“That was good. You were great. So tight. So nice,” Alan murmured.

The boy’s vocal response, the extent that there was a coherent one, was lost in his moans and groans.

Alan pulled off his body, and turned the boy onto his back. He stood, rolled the spent condom off his cock, tossed it toward where he knew there was a trash can, and put his hands on the boy’s body, gliding them around, fondling the boy, bringing him back to earth, able to afford to give the boy some pleasure to remember from the encounter.

The boy’s moans became more discernibly couched in pleasure and his panting decreased.

“Really? Really? I did well?”

“You were a sweetheart. Now you just lie there, like that. You’ll love the next time.”

“The next time?” The voice was weak, unsure.

“You’re OK, aren’t you? It’s all good with you, isn’t it?”

The affirmation was hesitant, but it was there. The boy had known there would be this experience at some time. He’d looked forward to it. Now he could look back on it as a hurdle managed. In any event, you couldn’t return to being a virgin.

Alan pulled away from him and walked around to the nightstand, standing there, his eyes drilling into the boy’s body, willing the boy to lie there and not to move—certainly not to make a dash for the door into the corridor—while he rolled on the second condom and lubed it up.

“So nice. You’re so nice. We’ll make such wonderful love.” He kept his voice as soothing as possible. He walked back around the bed, grabbed the boy’s ankles and spread and raised his legs. The ankles went on Alan’s shoulders as he moved inside the boy’s thighs. The boy tried to raise his torso and reach out with his hands as if to push Alan’s hovering chest away.

Alan surprised and shocked the kid by backhanding him across the face, sending the boy’s head back to the mattress. Alan clutched the boy’s throat with one hand and put his cock in position with the other.

“Fuck. Shit! FUCK!” the boy cried out as Alen entered him again, continuing to hold his head down with a grip on his throat with one hand and beating the kid’s cock off with the other while he moved into the dance of the second fuck. Access and slide was easier now for both of them.

Alan came, filling the bulb of the condom. The boy felt that he had and tried to raise his torso again. Alan punched him in the face. Not hard enough to bruise but hard enough to stun. The boy fell back, with a sob. Alan had come but he wasn’t fully satisfied. Not yet.

He pulled out of the boy and reached under the foot of the bed, coming up with a latex glove.

“What’s that? What are you ... oh, shit.”

The glove having been pulled onto Alan’s right hand, he moved the left to the boy’s face, covering his mouth and nose, starting to control the boy’s breathing to put him under control. The boy scrabbled at the hand ineffectually with his two hands but quickly had something else to worry about. Alan was moving his right hand into position, bunching it up, and slowly pushing it up into the boy’s anal passage. The boy writhed under him, again ineffectually, as he tried to get his next breath.

“Relax,” Alan directed. “You’ll open more if you relax. You’ll love it.”

The boy did manage to relax and even to start gently swaying, rocking against the flexing hand. He turned his wet cheek to the mattress and stared, almost vacantly, toward the dim light emanating from the bathroom. Alan was humming.

No, the boy most definitely would not mention this to his parents or anyone else.


It was the afternoon after a storm that came off the Atlantic and fourteen-year-old blond, blue-eyed angel, Toby, was walking the beach with an old friend of his, Jerry, an old gray-haired guy, also once a blond, still blue eyed, and in great, deeply tanned shape for a fifty-three-year-old. He was just in drooping shorts and sneakers. Toby was dressed for soccer, in shorts, an athletic T, with deep dips in front and at the arm holes, knee socks, and sneakers. He’d left a soccer ball up near where Whitehead Street ran up to the beach near the Seaside Café. The two friends, one very young and the other quite old, had found a crab trying to make its way back to the water and they were hunched over it, giving it encouragement, their foreheads almost touching.

An insistent man’s voice called out to them for Whitehead Street. The man had picked up Toby’s soccer ball. “Come away now, Toby,” he called out, “and get your ass over to Mallory Square. The cruise ship is in.”

 
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