Topsy-Turvy

Story Info
Everything not what it seems on a day cruise off Florida.
2.6k words
3.76
30.6k
1
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
sr71plt
sr71plt
3,009 Followers

I'd been working on my Chris Craft on the dock down in the keys for several hours, often looking over to admire the size and lines of a sleek, humongous yacht on the other side of the dock, before I realized that two men were sitting in the covered fantail of that craft and watching me too. I almost regretted that I'd stripped down to the Speedo to do my washdown.

Suddenly embarrassed by their close attention, I went over to the other side of my boat to work. But I took occasional peeks at the other craft, which had the name Topsy-Turvy painted on the stern, and couldn't help but notice that both men had binoculars pointed in my direction. From here they looked like Mutt and Jeff. The large guy was a little hard to miss—a bruising muscle-bound hulk in white shorts and a fluorescent-colored Hawaiian sports shirt. The little guy seemed no more than a boy, as spied from down here. He was in gray gym shorts and a T.

The day was hot and I'd been slaving for some time and, having raised my eyes to the boat to see if I was still under surveillance—which I was—I tuned into the fact that I had developed a deep thirst. I came around to the dock side of the boat to fish a beer out of the cooler I had sitting on the dock.

"Care to come aboard for a beer?"

I looked around and up at the main deck of the Topsy-Turvy. The big guy was standing at the rail, a beefy hand shading his eyes. He repeated, "I say, you look thirsty; care to come aboard for a beer?"

I was already opening the lid to the cooler, but someone else's beer was always a better idea to me than one I'd bought. "Maybe," I called over to him. "Does the offer come with a tour of the boat? That's some yacht you have there."

"Certainly can, yes," the big guy answered jovially. "We can even take it out for spin, if you like. We were going to cruise for an hour of two this afternoon anyway."

"Sounds good to me," I called back. "Just give me a minute or two to batten down the hatches over here." I'd done all I wanted to do on my Chris Craft that afternoon anyway. And I'd been arguing with myself over whether to take the boat out. It was a gorgeous day, but if I took it out, I'd have all of the scrubbing to do again when I got back to the dock. Now I could have it both ways—a short cruise in a real ship and my own scrubbed down nicely.

A couple of burly crewmen in spiffy whites appeared and started casting off on the Topsy-Turvy almost as soon as I got aboard and was moving to the fantail.

"Hello, there," the big guy said as I walked up to him. He was still standing by the rail. The grip of his handshake had power and authority in it. "I'm Tom, and this is Jerry. You tired us out just watching you clean your boat down over there. Come sit and select your poison."

Tom and Jerry. I almost laughed. But then that was better than Mutt and Jeff, I supposed.

I went past Tom as he turned to introduce me to the little guy. The little guy—Jerry—didn't stand up. He looked like he'd fallen down a flight of stairs, rather bruised and battered, and I thought immediately that maybe he couldn't stand. I leaned down, extended my hand, and introduced myself. His hand was trembling and was slightly moist. As I leaned down, I couldn't help but notice red welts on his inner thighs, and I wondered how the hell they'd gotten there. That would be hard to do in a fall down the stairs.

"Hello, Jerry," I said. "I'm Raymond. Call me Ray."

Jerry looked at me wanly. His eyes were glittering and much more expressive than any other part of his face. He responded his pleasure in meeting me in a rather weak voice. His eyes were boring into me, though, and I got the impression that he wanted to convey something to me, almost plead for something. But then Tom spoke again, naming beer brands they had on hand so I could take my pick, And Jerry's gaze snapped away from me and looked beyond me to where Tom was standing. I saw the little guy's eyes blaze up and then dim. Then Jerry looked down in his lap at his hands and said no more for the time we sat in the fantail, Tom and I drank beer and talked about boat maintenance and the Miami Dolphins as the yacht steamed out into the Atlantic.

I had worked hard, and there was a lull in the conversation, and both the sun I'd already taken and the beer I was drinking too much of got to me. My head went back into the cushions as the yacht steamed along and I dozed off.

My dreams were disturbed. I heard noises, disturbing noises, groans and moanings and sharp little cries. I jerked awake at the sound of a louder, muffled scream, my mouth sour from the beer, my head throbbing a bit from having had too much sun while scrubbing down the Chris Craft, and the sensation of not knowing whether the cry had been in my dream or was part of my sudden wakefulness.

Tom and Jerry were gone, but one of the white-clad crew members was standing at the door into whatever lay inside the ship's main cabin beyond the fantail porch. He was looking at me, and when I was fully awake, he pushed the door into the salon open with a hand and pronounced in a low, gravely voice, "They are in here."

I stood and walked over and through the door and then stood there, immobilized for the moment in shock. Then I turned, wanting to get out of there—and off the ship, not giving a thought to the fact that we were a good two miles off the strand of Florida keys now.

But the crewman, who was nearly as big as Tom, was blocking the door and staring at me in a way that I knew would not permit exit.

Tom turned around and gruffly told me to take a seat and watch. I collapsed into a tub chair near the door.

Then Tom turned back and flicked Jerry's naked buttocks with a leather whip, raising a little cry tapering off into a gurgled whimper. He then thrust his engorged cock inside Jerry's ass and began pumping hard in long strokes.

It was a regular S&M movie set. Jerry was naked and bent over a padded, brown-leather-covered gym pommel horse type apparatus that was closer to the ground than usual and didn't have the handles of a regular gymnastic pommel horse. He was barely in contact with the floor on his stretched toes. His wrists were cuffed to the legs of the horse on either side and his legs, straining back from the apparatus as he reached for the floor, were separated by a steel extender rod cuffed to his legs underneath the knees. This was holding his thighs wide in involuntary spread. His cries were muffled, because his head was covered by a leather harnessing that held a plug in his mouth. His buttocks and back and the backs of his thighs were red with welting from where Tom was whipping him.

I sat there aghast, unable to take my eyes away from the tableau. Tom, decked out in only black leather pants missing a crotch and black storm trooper boots, was fucking Jerry hard while flicking his legs and torso with the whip. With each upper thrust of his cock, Tom was lifting Jerry's scrabbling toes off the floor. The action stopped long enough for Tom to pull his cock out and strap a ribbed silicon extender over his already-huge member that increased its width and length appreciably, and then he reared his hips back and slammed the pole into the channel of the much smaller man. Jerry writhed under the augmented attention and turned his head back and looked at me—his eyes full of his pain and pleading.

I started to rise, to try to go to his aid, but the crewman at the door leaned over and pushed me back into the chair with a meaty fist to my sternum. The look in his eyes told me I'd better not move again.

As the fucking continued, Jerry began to writhe under the attention and to moan ever louder. I was embarrassed, but I had to admit to myself that something was stirring inside me—that I found this arousing. I turned and looked at the crewman at the door, and that didn't help a bit. He had his cock out and was beating it. My hand went involuntarily to my own cock, which was hard and throbbing inside the restricting pouch of my Speedo.

Jerry was moving his hips in a frenzy now, and he arched his back and bellowed under his mouth restraint as he jetted out cream under the powerful, relentless thrusts and whipping of Tom. I didn't know how the little guy managed it. He looked far too fragile and vulnerable against the brutish hulk of his oppressor.

After Jerry had come, Tom pulled out of him and just let the small guy collapse against the apparatus in muffled moans.

Tom turned to me and said, "You now. You fuck him now."

"Me?" I croaked in shock.

"Yes, you."

"I . . . I can't do that," I managed to blurt out. Possibly the severe tenting of the crotch of my Speedo and the spot of precum there somewhat belied that statement, however.

"We're not going back to land until you do," Tom declared ominously with glowering eyes. "Stavos," he bellowed, and the crewman at the door, who was busy stuffing himself back through his fly, came to attention. "Supplies for our guest."

I looked around as the guy at the door dug in his pocket. He came up with two condom packets and flipped them over to me. I let them fall at my feet and looked down dumbly at where they lay. A big hand—Tom's—reached down and picked them up and tucked them under the rim of my Speedo and then he stormed out of the door. The crewman shut the door behind Tom and then turned again, crossed his arms, and resumed his guard stance inside the door.

Jerry was whimpering and moaning. I rose and went over, and, as gently as I could, freed him from the collection of restraints, and half dragged, half carried him over to a bed at the side of the room.

"Thank you," he whispered. I turned to leave, but he clutched at me. "Please don't leave. Hold me. Please."

I sat down on the edge of the bed, and he curled up to me in a fetal position and wrapped his arms around him. I encircled him with my arms. I don't know who started it, but we began to rock back and forth, and he had a hand down the front of my Speedo and was squeezing my cock. The sensations of arousal and lust welled up inside me.

"I must go," I murmured, trying to pull away from him. But he held me fast, suddenly quite strong.

"No. You have to take me. You heard him. You won't get back to land . . ."

"Hush," I said, putting a finger over his bruised lips. "Don't try to talk. I . . . can't . . . I . . ."

He was pulling my face down to his with the back of his hand, the other one still encasing me cock. "Fuck me," he whimpered. "You must fuck me. It's the only way." And then he had his lips to mine and his mouth was opening to me, and we went into a passionate kiss.

I adjusted our bodies, coming up more on the bed, moving his buttocks to presentation position for my cock. When in a natural position for fucking, I opened a condom packet and, with a sigh of resignation edged with a chill of thrill, I crowned my cock.

"No . . . no . . . Bind me," Jerry whispered when I had the bulb of my cock at his rim. "Both wrists to both ankles."

"What?" I said, loud enough for the man at the door to take notice. "I can't . . . I couldn't . . ."

"He's watching; he'll know if you don't." Jerry was whimpering, pleading with me, reaching for the leather thongs on the bed coverlet.

So, I bound him, ankle to wrist on each side and rolled him onto his back, trussed like a sheep for shearing. And I put the palms of my hands under his buttocks and presented the bulb of my cock to his Tom-stretched anal entrance. And I fucked him. And he moaned and told me how filling and manly I was and how much he loved my cock churning inside him—loud enough for the monitoring crewman to catch it all. And, sad to say, I enjoyed it immensely.

When I was lost to any qualms about what I was doing and was fucking him vigorously in long penetrating strokes, he cried out, "Slap me. Punish me, Daddy. Slap me." He had to say it a couple of times before I complied, but when I did slap him on the buttocks and on his nipples a couple of times, he became frenzied in the fuck and his cock hardened. And he ejaculated up his belly.

Ashamed at having enjoyed myself, but unable to deny that this had been one of the hottest fucks of my life, I untied him and we went back into a rocking embrace.

"The punisher," I heard him mutter after several minutes, while our breathing was returning to normal.

"What?" I responded, in shock. I'd heard him perfectly, but I didn't quite believe what I was hearing.

"The punisher, Daddy, I want you to do me on the punisher. The apparatus. Put me on the apparatus again," he was pleading. "I want you to fuck me again on the apparatus. Please, Daddy, please." Jerry was licking his lips and giving me an intense, dreamy look full of lust and determination.

I sat up and away from him, staring down at him. Seeing him for the first time since I had boarded this boat.

"Tom," I said, accusingly.

"Tom works for me," Jerry said. "This is my boat. I told him to get you aboard." His face was set in a determined, suddenly strong expression. His voice now was equally hard. "Fuck me on the apparatus. We're not going back to land until you fuck me on the punisher."

I required Salvos's help in hooking Jerry up to the apparatus correctly, during which time Jerry became increasingly docile and started to tremble in anticipation, his cock hardening as we finished. After I had fucked Jerry on the apparatus, just as Tom had, but without the whip and the mouth restraint, substituting hand slaps in response to Jerry's angry declarations that he couldn't come if I didn't punish him, and I had unhooked him from all of the restraints, Tom reentered the room. He was still in those black leather, crotchless pants, big, thick cock at full staff and flicking his whip. And he had a mean expression on his face.

"Salvos," he bellowed. "Help our guest get hooked up to the punisher."

"Nooooo," I cried out. But Salvos already had me in his grip.

sr71plt
sr71plt
3,009 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymousover 9 years ago
Continuity

Stavos, Salvos! Gotta keep the names straight.

Share this Story

Similar Stories

Pranked A few college boys and a lot of sexy pranks.in Gay Male
Fun at the Nude Beach Two middle-age men enjoy themselves at a nude beach.in Gay Male
Deep Massage 18 year old gets a very deep massage.in Gay Male
My First Time as Just a Hole Being a softie up until now, this mouthfuck is a lot.in Gay Male
Straights Back Home Straight flatmates are reunited after few years apart.in Gay Male
More Stories