This is an original work of fiction. Any resemblance between the places and persons described below to actual places or persons is coincidental. All individuals who engage in sexual activity (male to male) are over 18—as should be any reader. Copyright 2023, all rights reserved. BD
This is the second of a three chapter story about Dylan's "coming of age"—at age 34. Dylan is an entrepreneur—and heir to a a mining fortune due to the death of a grandfather and a father. He loves sailing—and sailors. Chapter 01 describes his most recent hooks with a midshipman and a Russian émigré student in Annapolis. I recommend you read Chapter 01 before this.
Dylan and Sandy have a different kind of cruise
During their next few hours in the sun, Dylan had probed Sandy about his background. His mother and father were both Russian, sponsored by a sister for immigration after Glasnost fell apart and their small entrepreneuring venture also collapsed. If you were connected and bribing the Politburo, the end of Glasnost was a non-event. In fact, it accelerated the takeover of state wealth by the oligarchs—with not much impact on the "proletariat." But if you were small time and had used Glasnost to "go private enterprise," it was time to leave.
His father had been a dentist with a small elite private practice and was destined to become a low-paid employee of the state, assuming he wasn't accused of raping the proletariat by charging for dentistry. Even with a dentistry degree and more than ten years of practice, he couldn't get licensed in the US—the monopolistic ADS saw to that. So he and his wife both became dental assistants. They soon had saved enough to purchase a small house (with a large mortgage), a decent car, then a second, and finally an RV. Sandy had one sister, much younger. Both he and his sister had been born in the US and attended Pennsylvania public schools in a suburb of Pittsburgh where many Slavic families had settled.
Sandy played football (not a surprise given his physique), but didn't qualify for an athletic scholarship so he had decided to live at home and attend a community college. His only athletic activities now (in addition to very physical sex) were at the gym. In fact, he was a part time trainer. He hadn't decided on a career path, but at St John's that was easy—it was strictly liberal arts with a wide open curriculum, designed to prepare students for graduate study. It was very different from the community college (technical and job oriented) and Sandy loved the academic challenge. He thought that perhaps a gym/therapy franchise might be a possibility, but wasn't yet career-committed. He was not out to his family, but many of his clients expected (and got) full service. He was still wandering and wondering as so many his age at that time.
Lunch had been served by a steward on the aft deck. He had then buzzed Dylan's phone with a text since he assumed they were nude on the sun loungers on the prow, perhaps still playing, not wanting to be disturbed. Then he disappeared. Evermay was by then in the middle of the Bay, well-south of Bloody Point on Kent Island. Traffic had eased and there was little wind, so they were mostly drifting with minimum turbo power to maintain control. No sails had been deployed.
The others (Greg and his twinks, picked up at the Pink Pelican the previous night) weren't joining them—although the auto-controls would have permitted—and the "real" first mate was aboard. Dylan thought Greg might be a little embarrassed that he had brought two toys on board, and that neither was an adult in any reasonable meaning of that word! They were so into gaming that they spoke of little else. Dylan was beginning to wonder about Greg as the time for his departure to return to Greece approached. Why had he chosen two toys?
Dylan had checked at the bridge before joining Sandy on the loungers late in the morning. He found all three guys naked—no surprise. He spotted Greg's skimpy red posing strap linked over the handle of the wheel. Apparently that was the most he intended to wear for the cruise. Clearly he had fucked both Tom and Jerry (again, probably more than once, and recently). The two little nude guys, who looked like limp marionettes were perched, one on his massive thighs, hanging on to the wheel—and fortunately not steering because Evermay was on auto-pilot and the other on his monstrous cock. Greg seemed to be pleasuring each simultaneously—Tom (?) was on one thigh while Greg fondled his dick and balls with his large left hand as Tim whimpered his pleasure, and Jerry (?) was bouncing loudly on Greg's dick guided by Greg's other large hand. Greg turned around, winked at Dylan (it came off more as an apologetic grimace), and said, "I'm teaching these two young boys how to handle a loaded torpedo. They're quick learners."
"I can see that. And I know you're a quick loader. Carry on, gentlemen. I'll have lunch sent in here. You need to keep up your strength. Greg, we need to be back at the river dock by no later than 5."
"Yes, sir. Enjoy the rest of the afternoon. We'll be there on time."
After lunch, since he had had enough sun for the day, Dylan brought Sandy back to the cabin—which the staff had straightened—and left a chilling bottle of bubbly. Dylan motioned him to the bed. "On your knees, Sandy. I intend some payback for that monumental fucking you gave me this morning."
"Aye, aye, captain. But, please be gentle. I'm a virgin."
"You're kidding me. I love it. And you're going to love it. I love breaking boys in. And I particularly love breaking big muscular top boys in. I think we're going to try a few toys. You'll be begging me to let you cum soon. You're in for a first class initiation. Just say NO and I will stop."
Dylan went to the toy drawer and grabbed a medium-sized cock cage of silicon and stainless. He intended to put on his "full dom" persona for this event. "We start by putting this on. It will help you to obey me and remember your place." He obviously wasn't full-hard—yet. So Dylan lubed the shaft, pulled the cage over and locked the first ring at the base of the shaft. Then, he pushed his balls into the rounded sacs and locked the larger ring at the base of all his jewels. There was some room, but not much. The locks were electronic—and only Dylan knew the code.
Sandy got off the bed and looked down at the cage which pulled his dick and balls very low on his anatomy—obviously a first for him. "I guess I'm really trusting you now. It's pretty heavy. I've never felt so vulnerable or dependent before." Sandy was thinking that for a bottom, Dylan was almost always in total control—except when he was being pleasured to orgasm.
"That's what makes it better. You're a top, an absolute, confirmed masculine top. You've proven that. But, when I make you my bottom, you're going to have a whole new perspective—and a whole new experience. I've learned that the most dominant tops enjoy the hell out of bottoming once in a while—particularly when they are helpless to do otherwise. And that precisely describes your situation right now. It'll make you a better top. When power understands its limits, power is more powerful."
Then Dylan pushed him back onto the bed into a doggie position, lubed and inserted a cone-shaped plug with a small handle. He took it easily—too easily. So Dylan removed it and went to the next larger size, lubed it and pushed it in. This time he saw a bit of moisture in one eye—but Sandy wasn't going to give him satisfaction of showing pain. He definitely was a tough guy. Okay, have it your way. So Dylan waited a minute, pulled it out and lubed and pushed a still larger one in. This time he protested. "It feels like you just pushed your fist in."
"Quiet, babe. A big boy like you can handle it. It's only a size four, on a scale of one to ten. And, it's still smaller than my dick. And I think you actually like it. Your entrance sure sucked it in with a quivering welcome. I think you've done this before."
"Oh, fuck." Sandy dropped down to the mattress, but when he hit the cage, he popped up immediately. He wouldn't try that again. Just in case, Dylan pushed a large bolster under his gut and pushed his shoulders to the mattress. Then he got out some lotion, rested his chest on Sandy's back, molded his gut to Sandy's ass, and started massaging— pecs (including the hardening nibs), abs, inner thighs, glutes—raising Sandy's general arousal and anticipation. Dylan's dick slid over the lotioned crack and his balls kept tapping Sandy's, trapped in the cage. He was getting into the pleasurable part of the exercise. Sandy was enjoying the massage and purring like a kitten. As Dylan hit the glutes, he began to twist the plug, moving it closer to and nudging his prostate. Sandy moaned—this time in satisfaction.
"Hasn't anyone taught you the pleasures of the prostate?"
"I've had some fingers and some toys, but nothing like this. I do some of my customers, but so far, I've limited myself to blow jobs and fucking them. I don't do anal as a bottom with customers—it makes me feel too much like a whore."
"Then, you are in for a real treat—or treatment. I can make you cum with just this dildo, or better yet, my dick in your chute. We—and that includes you—won't touch your dick. And I guaranty that the orgasm will be longer and harder."
"You gotta prove that. But, I'm ready."