A gay sex stories: Dylan Thomas Merriweather III Ch. 03 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. Final chapter of three. Copyright 2023, all rights reserved. BD
Meetings in Washington and Time with Greg
Early the next day, a car and driver were parked at the gates waiting to take Dylan to his first meeting at the State Department. He met his advisor/lobbyist at the Fairmont for coffee and together they continued on to State. It turned out that several had been arranged and the meetings were unnecessarily long—bureaucrats are always anxious to join in on a meeting (and provide comment, even if off-point, redundant, or downright erroneous)—to prove their worth, particularly with a person like Dylan with money and influence. So, over the course of the morning, Dylan met with over a dozen, heard the same platitudes and non-committal non-promises over and over. He left, convinced that State was not going to do anything about the Chinese actions in Tanzania, except maybe fire off a few requests for field reports—assuming there was anything they could do. The availability of Tanzanian cobalt to US industry was not a high property at State—where commercial interests always fell to political or humanitarian issues. If the Chinese were demanding Tanzanian slave labor to pay down the debt, State would be all over it. But, not for a commercial threat.
Dylan had a quick lunch at one of his favorite Tex-Mex spots, accompanied by a his highly-paid lobbyist, and then called on his good friend (and one-time fuck-buddy), the junior Senator from Maryland. He explained everything again. The Senator promised “letters of inquiry” to both the FTC (over the proposed merger) and State (over the cobalt issue). He also agreed to put the issue of cobalt supply on the agenda of next week’s Commerce Committee meeting—of which he was vice-chair. Then, he asked when Dylan’s Saturday parties were starting and he was invited to join in “about” a week. “We’ll be saying farewell to Greg Andropolis, the guy I brought home from Greece. If you’re good, I’ll let you alone with him for an hour or so. He’ll give you a ride you won’t forget.”
Satisfied that he had done all he could—and more than ever confident that these issues would not be resolved politically, Dylan returned home. He scheduled another top level Zoom meeting at which he redoubled Weather’s future trading position authorizations in these commodities. Perhaps, no probably, these would be long term strategic issues, but in the short run, they presented terrific opportunities for trading profits. The next days would be a wild ride—in the trading market. He was going “all in” with Weather’s assets and planned to make another fortune.
But, he wanted to be really all in, that is, he wanted Greg’s “assets” pounding all-in him. He was aching for physical stimulation and release. So he buzzed Greg, “Meet me at Evermay, owners’ bedroom, asap. I need an infusion after all the blood I gave in DC today.” He walked out of his office and headed for the yacht where Greg met him with a mile-wide smile, a gin and tonic, and open arms. Greg embraced him and pulled him in for a long hug, pressing his lips to Dylan’s and his hard dick to Dylan’s gut.
“Looks like you could use a little lovin’, Dylan—or maybe a big lover.”
“Nothing little about it. I want it big and hard and fast. And now,” as he led Greg quickly to the suite. “Strip. I’m going to suck you first so you can last long enough to take me to some distant sensory paradise.”
“Yes, sir,” whispered Greg as he quickly shed his tee and shorts and stood, legs akimbo, arms across his hard pecs, pointing his massive erection right at Dylan’s gut—the pose he knew was that of the Colossus of Rhodes, (although he knew his priapic show was not “authentic” for the giant statue, only the private studies that preceded its construction). He truly was a Greek god. Dylan pushed him to the bed, knelt between his legs, swallowed, and began to suck as his thumbs and index fingers clamped hard on Greg’s nipples. Greg was near pain; no, he was in pain, but the best kind. Tonight, Dylan needed to dominate before he gave himself up. He was disgusted with the humble, beggar act that the government always demanded. And he was angry that he had been double-crossed in a deal. He needed to recover dignity—and dominance. So Greg endured it. In fact, he began to enjoy the pain/pleasure of Dylan’s aggressive assault on his cock and nipples. Dylan sucked and sucked and then he not so gently grabbed the base of the shaft and stroked. He reached under Greg’s balls, cupped them and pulled them away from Greg’s body. He did want Greg to feel a little pain. Then he sat back, took just the sensitive head between his lips and started to massage it with his tongue. It didn’t take long. “Dylan stop. You’ve got me. I’m cumming.”
“Do it. I want it all.” Dylan squeezed the balls and pushed on his taint.
And so Greg blasted into Dylan, down his throat, filling his mouth, and overflowing his lips. All of this while Dylan’s blazing eyes and rock hard cock told Greg that Dylan was in charge tonight. Dylan held the dick in his mouth for a long time, but realized that Greg was not going to go soft. What an incredible talent this boy had!
Dylan then finished stripping and positioned himself chest down on the bed. He stretched his legs to the side and moved the bolster under his gut. Then he gripped the headboard—in total surrender. Greg knew exactly what was expected. He reached over and grabbed the lube dispenser and placed it strategically on the bed. Then he bent over and began to lick Dylan’s crevice, then his rim, as Dylan began to climb the hillside of pleasure, opening and closing his fists on the sheet. Greg curled his long, talented tongue and penetrated the anus. Dylan began to rotate his hips, pushing up into Greg’s tongue and taking him deeper inside. “Use your fingers. I need it deeper. Now.”
So Greg lubed and began to penetrate, reaching for the p-button. Dylan felt the electric shock of prostate stimulation immediately. “Yes, right there. Harder. Keep it up.”
“With your permission, sir, I’m going to use something a little larger and longer.” With that, Greg pushed his steely cock into Dylan’s hole and began to scrape the prostate with each stroke. Dylan rose from the bolster, pushed his cheeks into Greg’s gut, seeking maximum penetration.
“Ahh. I can feel the monster. He’s really stretching me tonight. Pound me. Now, Greg. Cum with me. Take me home.”
“As you wish, sir.” Greg knew this game: act the dom, play the sub.
Dylan could feel Greg’s shaft inflate and heat, filling his cavity and sending pleasure waves deep into his guts. Dylan began to spasm, contracting his anal muscles, which pulled Greg over the edge. Dylan felt the hot, massive spurts deep inside and experienced an almost out-of-body experience—(actually an in-the-body-experience)–he felt that Greg’s cum was mingling with his own inside his bowels and spurting from the swollen head of his own cock. Simultaneous hard anal orgasms can sometimes feel like that—but it takes a pro with an enormous tool and stamina like Greg to orchestrate–and a seasoned bottom like Dylan to appreciate the feeling. Greg collapsed onto Dylan and enveloped him in his strong arms and legs, squeezing him into his chest, stroking him slowly. Greg was now the dom and Dylan his willing (and very empty) sub. And, his tension was gone. With moments like these, Greg was beginning to fall for Dylan as he caressed the smaller guy into submission and protection, but he quickly swallowed the thought. He was just a toy, hired help—and he had a life back home. Dylan was good, the best he had ever had, but there would be others.
Curiously, Dylan was also beginning to feel that as the time for Greg’s departure approached, their fucks were becoming acts of love. And he recognized that each time Greg took him powerfully, he finished protectively and gently.
A few minutes later, Greg got up and found the warm towels. But Dylan stopped him, “I’m going to need a shower. I don’t need to wash you away, but I do need to wash away the sycophantic slime that I waded in most of today.”
“I guess I need to join you—you probably have gotten that slime all over me as well,” Greg laughed.
“Well, tomorrow will be better. Sandy confirmed he would be here at 4 for your work-out. And Billy Carpenter will be here at 6 on Saturday. He can sail on Sunday, but reminded that he has to be in his bunk by taps Saturday night—so can’t spend Saturday night. So, lover boy, you’ve got about five hours to feed and seduce him Saturday before he vanishes. The fact that he even mentioned his bunk means he knows he’s gonna be dessert, if not the main course. I guess you made that clear to him at the Pelican—or he’s been doing research.” Greg paused for a moment, obviously trying to decide whether to speak. “Do you think it might be too weird if I asked Sandy to join us on Saturday and Sunday?”
“I think I’d like to end up with one of them as a regular fuck buddy or perhaps something more after you leave next week. I don’t think either of them can compare to you. But, as of now, nothing is exclusive—and I really haven’t even taken Billy’s temperature. I know you’re already match-making for me—or at least recruiting my next top. If you decide to do it, make sure Sandy knows he will be your date, not mine. I don’t want Billy to be confused. By the way, Sandy was a virgin until I took his cherry Sunday. So go easy. I don’t want him going all soft and “bottomy” on me. He’s a power top and I want to keep him that way for me. And I do want him tight. Make sure he understands that bottoming for you is not part of his deal with me. It will be interesting to see how two hunky tops manage to spend time together—particularly when both are into me, and one is interviewing his replacement.”
“Yes, boss. I think I’ll ask him to be my assistant on the bridge. And we’ll see how it goes. I’m ready to bottom for him if that is what he wants. Or if that is what you want. He’s big, but I’ve taken bigger. A little jealousy, assuming you get it on with Billy, can’t hurt. If you decide on him, you want him to be ripe and ready. But, I think he’s already hooked. You’re not so hard to take, Dylan.”
“God, you give me the greatest straight lines. Of course, I’m hard when you take me—and you know it. Good thing I’m addicted to your cock. Greg, your deviousness never ceases to amaze me. You’d make a good commodities trader. You’re a good reader of people. Most don’t understand that trading takes more than research and reading market trends; it’s also about reading people and anticipating their needs—and desires, then seeming to give it to them, while keeping it all for yourself. They walk away thinking they screwed you—and then they realize who did the screwing—and they are okay with that. Because you want them coming back for more. Trading is like screwing—except neither of the partners knows who is the top and who is the bottom until the money is counted.”
“No I wouldn’t. I can’t sit at a desk and watch a set of screens all day. I’d quickly go mad and lose all your money. I did the University routine in Greece. Papa demanded it of all his sons. But, it wasn’t for me. I like the sea, boats, and people too much to do something that takes me away from that love. I’m perfectly happy steering your boat, anchoring in your depths, and keeping you satisfied. I have simple tastes.”
“Well, we can see. I think we could accommodate your needs and benefit from your talents in some ways.”
********
Workout and Full Service Massage
Promptly at 4, Sandy rang the bell at the gates which swung open before him. He rode his bike to the portico, left it and climbed to the door. Greg opened the door before he even reached it. “Dylan is in the gym. I’ll take you there.”
Dylan found the next 75 minutes to be exhausting. Sandy was a good trainer. He quickly adapted to Dylan’s current condition, added a few exercises that would enhance the overall workout and pushed Dylan hard, but not so hard that he would feel more than a pleasant burn for the next day or so. All the while, he was careful to stroke Dylan’s ego and much of the rest of Dylan’s lithe muscular body. He was definitely a hands-on trainer “with benefits.” He knew how to tease Dylan into total-body arousal. Both sported periodic erections throughout the workout.
Then it was time for the massage. Dylan stripped, showered quickly, dried and stretched out on the table. Sandy had prepared the ointments and oils, and he himself had stripped. He was well-aware that Dylan expected more than a rubdown, but he was going to do his best to provide a professional massage first. He began with careful manipulation of arms, legs, feet, hands, fingers: pressing, stroking, pulling, healing knots. Then he moved to the larger muscle groups, using his full-body strength, often by mounting Dylan’s nude body.
Sandy motioned for Dylan to flip. Sandy repeated his stroking on the chest, pecs, front of thighs—avoiding any contact with the genitals. But, Dylan whose sighs became more and more sensual as the massage progressed was rampant. Finally, Sandy reached over, stroked the penis and bent over to take the cap into his mouth—using his lips to massage the shaft as his tongue stimulated the head and his hands fondled the balls. He was good; he was a professional. Dylan whispered a warning of imminent cum, but Sandy continued to suck and moved an oily finger to Dylan’s anus. He reached in, tapped the prostate, and Dylan blasted. Sandy hungrily swallowed all. “That’s the sweetest cum I’ve ever tasted.”
“I don’t think it’s the result of my good living! I know you need release, but give me a few minutes and I’ll help with that.”
“I’m getting some water. Can I get you some?”
“How about a beer? The fridge is over there.”
“First water, sir. Then, beer.”
Both guys relaxed, nude, on the towel-covered glider on the gym balcony which overlooked the river while they sipped from the icy Fiji bottles. “This is a view that never tires me.” After a few minutes of silence, Sandy reached over and began to stroke Dylan’s neck. Dylan dropped his head back into the caress and smiled at Sandy. “For a hunk, you sure have soft, talented hands.”
Sandy reached over and pulled Dylan into his lap and embraced him. His mouth went to Dylan’s and their tongues dueled as their lips locked. Their erect cocks were side by side and Dylan reached down to stroke the two together.
“How about a ride?”
“Sure.”
So Sandy reached over for a condom and rolled it on. Then he lubed himself and repositioned Dylan’s legs on either side of his hips and lifted him to his chest. Sandy’s hands reached under and began to open Dylan with lube as Dylan squirmed on Sandy’s hard muscled chest. Finally, he lowered Dylan onto his shaft, bottoming quickly. His arms went around Dylan’s back, then fell to the ass cheeks as he began to lift and pump. Dylan wanted p-contact and so he locked his hands behind Sandy’s neck and stretched out backward. Yes, perfect. Sandy’s big dickhead made direct contact with the prostate. Sandy’s strokes became intensely stimulating, sending shocks through Dylan’s gut—and dick as they rocked gently on the glider.
Then Sandy stood, holding Dylan in place so when Dylan bounced he got both maximum penetration and prostate stimulation. Soon Dylan shouted, “Now, do me. Do me now. I want to feel your heat.” And of course, Sandy performed on demand. He shot several times, filling the bulb of the condom with his hot essence and then pulled Dylan into a total body contact embrace with Dylan’s legs locked around Sandy’s waist. Dylan’s dick spouted between them, covering Sandy’s chest with spunk. Sandy fell to the settee as both guys began to relax in the wonderful afterglow of good sex.
“I’ve got several video conference calls tonight, so I can’t join you for dinner. But, Greg would like to have dinner with you on Evermay if you would like. He’s only got 10 more days in the States.”
“I think you must know that you’ve got the trainer-masseur job if you want it. The standard fees around here are $75 for a home gym trainer visit and $150 for a home massage, usually more when it’s full servicea and with tip. I’d like to see you twice a week. So, shall we say $2000 a month?”
“Dylan, you don’t have to pay me.”
“Oh, absolutely, yes I do. If you won’t take payment, then I’ll find another professional.”
“Okay, but we’ll talk about the monthly. It does seem high to me. And I’ll be pleased to have dinner with Greg. He seems like a really nice guy—and obviously he is in love with you. Shall we do this again on Thursday?”
“Yes, unless I have a corporate emergency—then I’ll call. And believe me, Greg is not in love, at least not with me. He is itching to get back to his friends in Greece. He’s very much a free spirit and likes challenge and variety. He no longer has either with me. I wasn’t born yesterday. It’s now purely transactional. He gives me what I want—and I’m usually available to him when he needs to get off.”
“For a successful young entrepreneur, you sure can delude yourself concerning the feelings of the people around you. Believe me, Greg is hooked. I can see it in his eyes. By the way, is that why you need to pay me? Are we now transactional?”
“No, I need a pro trainer and masseur. And I’d like a regular fuck-buddy with whom I can go bare—and I definitely enjoy being with you. Can we try to keep the two separate?”
“We can try. But, I can read Greg. If you asked him to stay, he definitely would. He’s like a puppy who’s imprinted his new master. He’s definitely fallen for you. You’ve turned a free-spirit, natural top into someone who would do anything to gain and keep your approval.”
Dylan showered, pondering a bit Sandy’s words about Greg, and prepared for his calls. Sandy showered and walked over to the yacht to find Greg. After dinner Greg invited Sandy for the sail on Sunday (deciding to let Dylan have his privacy with Billy on Saturday). As Sandy was leaving, Greg pulled him into a bro-embrace and planted his hands on Sandy’s cheeks, inside the shorts. “I’m looking forward to having some fun on Sunday. Don’t worry, Dylan won’t mind. In fact, he gave me permission—and he did tell me you were a preferred top. At least for Sunday, you’re going to be my assistant—and date. We’ll decide then where that might lead. You can say no anytime. He may stake a claim on you in the coming weeks, but right now, he’s still at the get-to-know-you stage.”
“Good to know. I like Dylan, but I can’t read him yet. I assumed you guys had something special going on. I certainly see it in your face when you think he isn’t looking at you.”
“I’ve been with him for about six weeks now—and I still don’t know what makes him tick. He’s a very complicated man with very specific tastes—that change from minute to minute—often depending on how the business is going. But, I do know he makes a lot of money and that he treats his friends—and lovers–very well. He’ll never lie to you. He won’t cheat on you if you get it on. And he’s the best lay I’ve ever had in my life. What’s not to like?”
“Since I’m obviously one of his potential choices for the coming months, does that mean I can expect you to give me a rough time on Sunday? If so, I think, I should pass for now. I don’t need to be hazed.”
“Please come. I’m not into punishing potential competitors. I think it’s more like I’m measuring those that Dylan might want. We won’t do anything you don’t want. I’m not a monster—jealous or otherwise. I would do anything for Dylan—including keeping my hands off you and my dick out of your ass if that is what he—or you–wants.”
“Okay, it’s a date. I guess I should learn something about this boat since it’s Dylan’s passion. Don’t sell yourself short, Greg. You’re a neat guy, street smart, and a prize specimen of young manhood. Dylan could definitely fall for you.”
********
Saturday with Billy
On Saturday, Greg drove over to pick up Billy who was dressed entirely in white—a white button up “official” shirt (sans epaulets and name tag!), loose white Bermuda shorts (which nevertheless bulged provocatively at the front), and white boat shoes. All of which contrasted with his dark glasses, dark tan, dark blue eyes, and curly black hair (which was just beginning to grow back from the head-shave of six weeks prior). He had a small duffel with Academy insignia. He hopped into the Range Rover and was driven to the mansion—only about ten minutes away, even in Saturday traffic. On the way, Greg described how he had met Dylan and why he was in Annapolis–and noted that he would be returning to Greece in less than two weeks. As they approached, around 6, Greg used the remote to open the gates. Billy’s eyes popped at the size of the Victorian pile in front of them. “Is this a movie set for a vampire movie? Does anyone actually live here?”
“Actually, the interior is completely up to date and modern—and wait until you see the yacht. It’s straight out of science fiction. Dylan is thoroughly modern and completely familiar with the high tech world. He keeps the house exterior as-is to honor his grand-dad and probably out of deference to his more conservative neighbors.”
They pulled up to the front. “Let’s go around back. There is a pool house if you need to put on a swim suit. And I am sure Dylan is either in the pool or on the phone next to it. You are the only guest tonight.”
“I knew this was a small party—but I’m the only guest? So I guess I committed when I agreed to come last Saturday at the Pelican. Of course, I knew that. I’m definitely on the menu—or maybe the entertainment.”
“You won’t regret it. I’m off tonight, so I won’t be around. But, I’ll be right here at the Rover to drive you back to the Academy at 11:15 to be sure you don’t miss curfew. Then, I’ll fetch you again for the sail tomorrow at noon. Go on through that arched-gate over there.”
Billy walked over, through the gate and down the steps, marveling at the size of the pool, the modern pool house and the yacht moored to a dock just beyond. He realized immediately that everything had been arranged for total privacy. He spotted Dylan on a chaise with buds in, listening to music—or perhaps on a business call. Dylan was nude. Billy walked to the pool house, dropped his kit and his duffel and emerged a few seconds later, totally comfortable with his own nudity. Dylan looked up and smiled. Billy was framed in overhead sunlight and already with the program. He was about six foot, with very defined muscles and a large, long, uncut, low-hanging dick. He was definitely horse-hung, one of the largest Dylan had ever seen. If he was also a grower, Dylan was going to be in for a world class ride. Billy had dark blond hair, dark eyebrows and lashes, a trimmed pubic bush, but was otherwise clean-shaven. He looked really young, clean and ripe. Walking toward the pool, Dylan had a flashback to that incredible debut of Brad Pitt in A River Runs Through It—probably the most beautiful and desirable man on the planet when he exploded on the screen. Dylan was pleased. He had not been wrong. Billy was model, porn star material. They were definitely going to have some nice “clean” fun.
“Welcome, Billy. I was just going to swim some laps before dinner. Will you join me?”
“Of course.”
“Dylan walked to the board and performed a nice sharp dive, rising to shake the droplets from his face and blond hair. Billy followed with a dive which absolutely denied his muscular bulk—it was clean and perfect. Billy was clearly a top athlete in great shape and in control of his body. They swam laps for a half hour; then Billy rested against the tile at the edge with the water to his chest. Dylan followed and trapped him. Billy knew it was now interview time. He was ready. He was already nearly hard.
Billy was the first in his family to “go military” and in fact the first to go to college. He had just celebrated his 20th birthday—so he was a babe. He had been All-State in Colorado, his home, but he wasn’t at the Academy to play football—although he had tried out for the freshman team and made it. Being a quarterback at a Colorado high school—even an All-State player—was not like the same status from Texas, the South or even the Midwest. Besides, the Navy might be reluctantly accepting of gay midshipmen, but a gay quarterback was probably beyond the pale. The military alums would howl.
He was in Annapolis to get a good engineering degree, put in his time in the Navy, and then move into the world of commerce where he could make some real money. He was one of two, with a younger sister. His Dad worked for a large ski resort—grooming trails in winter, landscaping in summer—and doing general go-fer stuff when asked. Mother was a housewife. He was gay. Most of his high school friends didn’t know—but the Navy did. So long as he was discrete, they would leave him alone. “Dylan, I know you’re a legend in this town. At least a dozen guys gave me advice about tonight and tomorrow. For me, this is just a couple of dates. I’m looking to have some fun. I’ve had almost no experience. I came out last summer after fooling around with a long-time bud. We tried some stuff—in fact, I think just about everything, but I’m just an amateur. He’s been my only partner. I really like the way you look—and what I’ve heard about you. I’m expecting to have some fun and learn some things from you. And what’s not to like about this place and that warship! But, I’m a little tense. You’re out of my league.”
“Incidentally, it’s not a warship, it’s a love boat. And you may be inexperienced, but you’ve got a world class body and a huge dick. That goes a long way.” Dylan reached down and stroked—it took both hands.
“Well, it looks a little like a naval version of a stealth bomber.”
“Are you talking about my boat or your dick?”
“Let’s go see the yacht while they set up dinner in the pool house. That basket has some tees and stretch French terry pool shorts. Feel free to put them on if that makes you more comfortable. They are mostly what I wear when relaxing and moving around. We might encounter some crew on the yacht.”
Both guys quickly pulled on white tees and shorts and walked over to the yacht. The interior was even more impressive than the sleek navy and grey Italian exterior (the pontoons were navy, rimmed in stainless; the superstructure was dark grey)—everything was leather, marble, shiny stainless with touches of exotic wood “bright-work” to warm it. Dylan made drinks at the bar in the large top deck lounge, showed Billy the bridge with its banks of electronic controls, and then they went down to the owner’s cabin. It was large and everything was dark, save the white marble floor. Billy looked up and noted the full-mirrored ceiling. There was nothing subtle about this space. It was for pleasure, a very high class room for seduction and fucking.
Billy placed his drink carefully on a glass-topped table and stripped. He reached over to Dylan and removed Dylan’s shirt and shorts. Then he pulled Dylan into an embrace and reached down to cup his ass cheeks, allowing his long fingers to stray to the crevice. “I was told you liked aggressive partners. I hope this is okay.”
“You don’t have to ask. Take what you want, anytime. You’re a good looking guy with a nice fat long snake. I’m always ready to play.”
Billy scooped Dylan up, swiveled and dropped onto the edge of the bed. Dylan ended on Billy’s lap, Rodin’s “Lovers” pose. Billy pulled him in and deep-kissed him, tightening the embrace as his lips trailed down Dylan’s neck and shoulders to his nipples. Billy’s hands seemed to be everywhere, caressing, squeezing, hugging—and in a very nice maneuver, Billy swiveled and ended up with Dylan stretched out on the bed with Billy covering him completely. Billy squirmed around, poking his long erect cock in various places as his hands continued their caresses and his lips captured Dylan’s. So Billy was a lover! In his inexperienced introduction to man-on-man sexuality, Billy had developed an intimate and loving foreplay. He was everywhere—taking Dylan’s dick between his lips, poking his long fingers into Dylan’s crevice, licking Dylan’s rim, mouthing his balls, stroking his pecs, and nibbling on his nipples. He knew how to arouse and he had the quarterback’s hands and fingers to do so. He had strength, but also finesse. Each time Dylan thought that Billy was moving to the main event, Billy surprised him with another position, another caress, another kiss. Dylan’s arousal was getting intense.
“Now, lover-boy, I want you to take me. You can decide how and where.”
Billy immediately pushed Dylan onto his back and lifted his legs into a wide V, placing his calves on Billy’s powerful shoulders. He wrapped, lubed and prepped Dylan with lube. Then he started the entry process. By this point Dylan was nearly frantic with desire. Billy’s dick had grown—he definitely was a grower—to well over 10 inches—with a large rounded helmet which had darkened to a deep purple. And his balls were large and low enough that they could provide some interesting pressure on his taint when Billy bottomed with his impressive battering ram. “Just push it in. I can take it.”
And so, Billy used his powerful thighs to drive, scraping the prostate repeatedly, until he finally bottomed deeply in Dylan.
“I feel like I’ve got a baseball bat in there.”
“My bud used to tell me that I had a sleeping giant anaconda in my briefs.”
“He was right. You’ve got one of the longest and largest dicks that has ever been in me. Now show me what you can do with it.”
Billy started pumping, watching Dylan’s eyes carefully as he repeatedly rammed the prostate. And for an amateur he was able to hold out—of course, he had jerked off twice already that day—until Dylan’s cock began to leak. Billy reached under and stroked Dylan’s taint and cock-base. He brought Dylan’s pre-cum to his lips and sucked loudly on his fingers. Dylan’s face darkened. He was cumming. So Billy drove deeper, tensed his legs, folded Dylan in two, and exploded over and over into Dylan’s gut. Dylan could feel the spasms and responded by tightening his anal muscles around Billy’s shaft. Billy smiled a thank you. Then, Billy released the calves and fell onto Dylan’s chest, both men panting with the exertion of a very physical fuck after long erotic foreplay. Billy reached around, rolled over and began to pull Dylan into his body, stroking his back and thighs as he did so. Dylan’s head fell into the hollow of Billy’s shoulder—so Billy reached up and began a gentle massage of Dylan’s tense neck muscles and then on down his back. Soon Dylan’s breathing began to slow and Billy relaxed, content to hold his partner in a close post-coital embrace as their breaths and heartbeats synchronized.
“Billy, you may be an amateur. But your moves are professional—and athletic. Let me rest for a minute. I’m an old man compared to you. Then we’ll shower and go get some dinner.”
Nearly an hour later, the two guys, dressed again in white terry, went to the pool house where a delicious meal had been set: oysters on the half shell and large prawns on large platters of ice, Chesapeake Bay crab meat cakes, and fresh corn on the cob and hush puppies. Billy noted the dessert in the glass-fronted frig cabinet—a pie. “What’s the pie?”
“My favorite. Chef makes it for me every few weeks. He starts with Edy’s mint chip ice cream which he remakes with extra heavy cream, liquid marshmallow and chocolate bits. That’s the filling for the rich chocolate crust which is Ghirardelli bittersweet chocolate brownies—slightly overcooked, broken up, buttered, and reformed into a crust. Then it’s all re-chilled. The perfect summer dessert—actually, it may become my second favorite dessert. I have a feeling that you may become my favorite.”
Both guys ate heartily. It had been a strenuous first meeting. Dylan was surprisingly touched by Billy’s obvious tactile sense of tender love—there was really no other word for it. For Billy, sex was obviously love, not mechanics. What a refreshing experience!
“Normally, I’d expect an encore at this point. But I’m really tired, very full, and still a little sated by your athletic performance in the first round. Shall we recess until tomorrow afternoon?”
“Sure. It’s almost time to get back anyway. And, I’m not really into quickie release type sex—except when I do myself. I’ve enjoyed meeting you Dylan. I hope I passed the audition.”
“You are definitely in the finals of America’s ‘Top’ Talent. I’ll buzz Greg and tell him you are on your way. See you tomorrow. You’re definitely on the party list.” Billy embraced Dylan, pulled him into a deep kiss and stroked his back. “I look forward to it.”
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Sunday Sail on Evermay
Around mid-day on Sunday, Greg pulled into the estate with both Sandy and Billy in the Rover. As they all approached the pool, having stripped in the pool house, Dylan was confronted with a trinitarian apparition—three different, but equally magnificent men, all about the same height, one dark and two light, all tanned, all muscled and all very well-endowed. Flashes of an impending orgy whipped through Dylan’s mind. But, of course, he remembered Sandy was there with Greg for the afternoon. Dylan knew he would be in an arousal state for the rest of the day. Maybe he could change the script—and get thoroughly fucked three times by three different guys—it wouldn’t be the first time. He’d wait and see how it played out.
“Hey, guys, welcome. I presume you have had an opportunity to get acquainted. Let me suggest our schedule. Lunch is set up on board. But, September on the Chesapeake means warm water and jelly fish—so it’s not likely we will be able to swim from the yacht, although there is a hot tub on the lower deck. We’ve got about 30 minutes to swim here first if you want. Then we’ll board, have lunch and enjoy a short cruise on the Bay. We can swim here again when we return if anyone wants.”
Greg answered for all. “Let’s dive in.” And so they did and swam laps for about a half hour. (Except for Sandy who paddled around quietly in the shallower end.) Then, they got out, walked over to the bin of terry tees and shorts and dressed in “whites” for the cruise. Before 1, they had sailed the brief distance down the Severn and were on the Bay. The first mate took the bridge as the four sat down to seafood salads, cheese and charcuterie. A nice light chilled Chablis Grand Cru was served with the meal. “I think this may be Greg’s next-to-last official cruise. My regular captain has been away for a month—two weeks of Coast Guard re-certification classes and two weeks holiday with his family. He plans to be back in Annapolis next Friday and starts here again the following Monday. I’m going to miss having Greg as a captain and companion. Let’s toast, Greg. The most exciting Greek boy I’ve ever met. If only he’d accept my offer of employment with Weather.”
“I had not expected a formal farewell a whole week before I plan to leave. Are your throwing me out already? And we really haven’t talked about an ‘offer.'”
“Not at all. But who knows when I’ll get a chance to praise your skill and attributes with others around before you leave.”
“This has been one of the best experiences of my life. Dylan, you are an absolute prince. I look forward to meeting up next year in Greece.”
“That’s a deal. But maybe we can arrange something before then.”
“I’m definitely up for that. Now, Sandy, come with me. I promised to show you how this ship handles itself—particularly in the light breeze we have right now.” So Sandy, perhaps a bit reluctantly, got up and followed Greg to the bridge, leaving Dylan and Billy in the lounge.
“Let’s head up to the sundeck on the prow. It’s sunny, but cool up there with the apparent breeze created by our forward motion.”
“Sure you don’t want to show me the owner’s cabin, again?”
“The sundeck is totally private. And it’s not visible from the bridge which is under it. Let’s go, tiger. I’m ready to play.”
The sun deck consisted of a railed wooden-floored space at the very top—a slightly recessed deck shared only by a small bar and the top of the staircase at the rear. The mainsail mast stood high above this small bar structure, while the furled jib created a strong diagonal to the lower prow. There were a half-dozen chaises, some in shade, one of which was a double. All had thick mattresses and multiple throw pillows. The space was reached by a spiral staircase from just behind the bridge and could be locked from above if desired.
As they walked past the bridge, they realized that Greg had left the access pocket door open. So, Billy was treated to the arousing sight of a naked Sandy bent over the wheel, holding on to the spokes and arching his ass up and back toward Greg. Sandy’s arms were outstretched in front, showing tensed enormous guns and thighs over spread-eagled legs, thus creating a perfect target for a plundering cock. Greg was also naked, his arms holding Sandy hard to his body as he rode Sandy’s ass from a standing position. Sandy was moaning loudly in apparent satisfaction while Greg’s own glute muscles moved with each thrust. Greg’s ass was obviously a work of art, particularly when tensed and in motion. Greg was getting a going away present from Sandy. (Dylan’s could wait.) Billy paused, enjoying the live porn show until Dylan motioned him up the stairs. Watching two muscular tops going at it was an incredibly erotic turn-on.
By the time they reached the deck, Billy’s terry shorts were tenting so badly that Dylan feared he would tear the soft terry with his massive pole. Both guys stripped and Dylan pointed to the double chaise. “Shall we? You can pick up where you left off last evening.”
Billy approached Dylan, and picked him up easily in a fireman’s carry, threw his chest over his shoulders, placed his large hands firmly on Dylan’s cheeks, and insinuated his fingers carefully into the cleft—and then in an amazing feat, turned his head to the side and sucked on Dylan’s ass cheeks, creating a dark brand. Billy was strong and knew how to assert his dominant strength, despite his young age. He stepped to the chaise and carefully laid Dylan on the towel-covered mattress and placed himself beside him, facing him. He reached over, pulled Dylan into a tight embrace and once again began the deep kissing, the fondling, the caressing, but this time with some urgency. “With your permission, I’d like to make this first one fairly quick. My balls are aching and I need release. Then I can give you the attention you deserve with an encore. I can recover pretty quickly.”
“You don’t have to ask. I understand. Let me take care of you, Billy.” Dylan pushed Billy back onto the chaise and went to work with his talented lips and hands on Billy’s shaft and balls. Billy spread his legs, placed his feet on the chaise and lifted his hips. Dylan knew how to do this. He reveled in Billy’s musky aroma, taking deep breaths. He licked the pre-cum and pushed his tongue down into the tight hood covering the head. He stroked the shaft lightly, then more roughly—realizing that deep-throating was completely out of the question. He brought Billy to the brink several times as Billy grasped his hair and then his ears, nearly pulling them from his head; each time, Dylan suddenly stopped and squeezed the base of Billy’s penis. He waited as Billy’s cock continued to throb and darken, then quiet. Then he would start again.
“Please Dylan. This is not fair play. I’m going to explode from this stimulus—and I don’t mean ejaculate, I mean literally explode. You’re going to have body parts littering your entire deck. My blood pressure must be over 200. When someone as good as you does me, I feel it over my entire body, not just my dick and my balls. I’m tingling from my toes to my lips.”
“Well, I’m going to drain you Billy. I know how fast young men like you recover and I want a long slow fuck from you this afternoon. I want you inside me, stroking for an hour.” With those words, Dylan took Billy’s head in his mouth and using his tongue pushed the hood down as his cheeks created the moist, hot vacuum. Hands cupped Billy’s balls and the heel of Dylan’s hand pressed hard on Billy’s taint. Dylan released the taint and squeezed the balls. Billy blasted, the first hitting the back of Dylan’s throat, the second and third filling Dylan’s mouth to overflowing. Then Billy fell back onto the chaise, totally drained. Dylan climbed over him and kissed him deeply sharing some of the spunk that was still in his mouth. Billy’s arms came up and held Dylan’s head to his as his tongue deeply invaded Dylan’s mouth.
Then, the two basked in the sun for some time, enjoying the soft salty breezes as the yacht made its way south past Kent and Tilghman Islands. The bay widened and the breeze picked up. Silently the Kevlar mainsail rose high on its pole and a jib unfurled in front of them. Interestingly, from ship-side, the jib was transparent. The speed picked up and the yacht began to pitch. Near-silent rotors were engaged and the sails were trimmed. It was exhilarating as the speed increased, and it all seemed to be happening with a ghost crew. Not one person appeared.
Billy rose and stood in the prow, enjoying the technical marvels that Evermay sported, smiling and relishing the wind in his hair as his cock rose like an enormous bowsprit. He turned, fluffed, and moved to the base of the chaise. He pushed Dylan’s legs apart. Then he dove in and began to suckle on Dylan’s hardening dick, bringing him to his long, hard condition. He reached under Dylan’s cheeks and, using his powerful hands, raised him to a position where all of Dylan’s most erogenous spots were within reach. Billy began a relentless exercise of tonguing, fingering, caressing, and penetrating. Then, he dropped to the chaise, flipped Dylan and spooned him into his gut. He caressed, squeezed, stroked, massaged as Dylan’s arousal skyrocketed and his dick hardened like steel. “How do you want it this afternoon, lover. Your wish is my cummand.”
“Take me hard and deep like a stray bitch dog in heat.
“No, but I will take you like my favorite pet. She’s always horny. And she won’t keep her nuzzle out of my crotch.”
“So long as it’s hard and feral.”
“Oh, it’s much better when you know your pet and his e-zones. And I think I’m learning yours. Ruffff.”
Dylan fell forward and rested on his shoulders, arching his back and presenting his well-formed ass for inspection—and more. Billy stepped behind and continued to open his partner—always with one hand stroking bare skin—pecs, abs, hips, thighs. Soon Dylan felt the familiar squirt of lube deep inside and the pressure of a wrapped weapon at his gate. He pushed back and Billy slid in, stretching the tight sheath and stopping once the huge head had cleared the ring. “Keep going. I can take it.” So Billy rocked, being sure to scrape the prostate with each stroke, moving in an inch or more with each push, ultimately seating his balls on Dylan’s. He reached under, took Dylan’s manhood in hand, squeezed it hard and began to stroke. He felt Dylan’s abs contract and so he pulled hard and brought Dylan into his lap—this time with his cock planted deeply in Dylan’s gut. Dylan had never felt so full. He could feel Billy’s pulse throbbing deep inside. Billy pulled Dylan back into his chest as Dylan turned his face and Billy captured it with a deep kiss. His lips trailed down the side of Dylan’s neck until the tongue reached out and stroked the hollow. It was pretty obvious that to Billy having sex meant making love. He was a compassionate and careful lover, aware that his enormous size could hurt or pleasure. And he knew how to use his quarterback hands, his supple lips and his enormous cock in simultaneous stimulation. Dylan didn’t know anything about his previous partner “bud”, but he guessed they had enjoyed passionate intercourse from the very beginning. Billy was a talented, considerate, and wonderful lover. He gave pleasure as well as he took it. His youth and inexperience were a disguise—he was definitely an exciting natural man-lover.
Dylan was quite content to rest in this position, aroused but in control, and very full. He pushed his back into Billy’s chest and reveled in Billy’s muscularity as Billy slowly massaged Dylan’s pecs, focusing on his hard erect nipples.
Billy warned of his cumming orgasm, pushed Dylan back onto the chaise while grasping and stroking his rock hard dick, and fell on top, squirming his pole deep into Dylan’s guts. The spasms began immediately. Dylan counted ten! How much spunk did this guy manufacture? But, Billy wasn’t letting Dylan go “just for the ride.” Finally, Dylan exploded into Billy’s fist. Billy stretched out to cover Dylan and whispered into his ear, “For an old man, you’re the best lay I’ve ever had, Mr. Merriweather.”
Dylan could only laugh. “Hell, you told me I’m only your second. I’ll show you old man, some day young man. When I fuck, I can hold off for a half hour until my young bottom screams in ecstasy. And when I bottom, my top is as sore as I am when it’s over.”
With those words, Dylan tensed his ass muscles and held Billy hard inside, milking his sensitive already spent cock, until Billy shouted, “My God, enough. You’re going to break it. Or maybe me.” So Dylan relaxed and Billy slowly withdrew, removed the condom and pitched it to a nearby basket.
They dreamily relaxed in each others embrace, enjoying the late afternoon breeze. Dylan’s mind began to race. Like a lightning bolt, a realization came to him. Billy was teaching him about the possibilities of love. A twenty year old baby seemed to understand more than he did. It was possible to be taken, hard and deep, while being simultaneously and tenderly stroked in love. A bottom didn’t have to be the receptacle for a dom top—he could be the recipient of a very big man’s love, a man who knew how to use a powerful symbol of masculinity and power to give pleasure, physical pleasure and the more lasting pleasure of love. He thought again about the ability of a loving young guy to teach. Dylan was, with this realization, taking the first step toward happiness. Billy had captured his imagination—and his feelings—in just a few hours. He had had a taste of how much better loving is than fucking. And being loved by someone with trophy equipment was even better. But it was important to realize that gentle foreplay was not necessarily love—it might be habit or act. It might indicate a capacity to love, but it wasn’t always love. Was Greg giving him both?
Dylan thought back to his year with Ollie. He had come close to moving from the mechanical pleasures of friends pulling out the best and most pleasure from each other over extended time to something more. But he and Ollie had never taken that step, both understanding that an endtime loomed in June. He had held back from love, knowing it was futile. Billy had shown him that at least the outward superficialities of love could be achieved in every act—it only took a certain mindset which discarded thoughts of the future and personal satisfaction in favor of staying in the moment and giving instead of taking. The future would happen organically and inevitably. Just be open to it.
Slowly, Dylan came to the realization that throughout his daydreaming, Billy was caressing him, reaching lower and lower until he grasped Dylan’s hardening manhood. Billy was hard again! Dylan wiggled his but into Billy and reveled in his youthful virility. Billy reached over and wrapped. He lubed and began the insistent pressure on Dylan’s ass. Then he stopped, rolled onto his back and pulled Dylan on top. Dylan reached back and began to draw him in as Billy rose to enter. He pulled Dylan down and began the deep tongue thrusting that Dylan had already come to expect. Billy pumped and Dylan fell into the delirious pleasure of being taken yet again by this beautiful lover with this massive cock. His prostate was stroked again and again as passion and heat rose. Billy could probably sustain this act forever. He was so young, so athletic—and this was his third within a few hours. But Dylan could not. His thoughtful daydreams had brought him well along the pleasure continuum even before Billy took him. Dylan shouted in ecstasy and shot between them as Bill followed. Then Dylan collapsed into Billy’s arms and closed his eyes in completion.
Soon, Dylan felt that Greg was turning Evermay. It was time to return home. An hour later, they were at the dock. Dylan was a changed person—or at least he had walked through the gates into a garden of potential change.
But he was faced with a dilemma. He had hoped to be able to choose a regular fuck buddy this afternoon. Greg would soon appear to drive Sandy and Billy home. How should he leave it? He wasn’t willing to give up either.
Sandy was a muscular, beautiful lover, a power-top—and a terrific trainer and masseur. And he was almost always available. Had Dylan already set the pattern with him so firmly (as mechanical and transactional) that their relationship could not grow? And was Sandy into Dylan or what Dylan represented in terms of opportunity and wealth?
Billy was one of the nicest and youngest partners that Dylan had ever taken on the yacht. Just thinking about his body and his equipment made Dylan shiver with want. Billy had boyish charm, innocence, and was massively hung. He was a compassionate and terrific lover. Anyone under him would feel cherished and loved. But, being only in his first year at the Academy, Billy would often be unavailable—subject to curfews, weekend training commitments, and of course, intense study demands. Overnights would only be possible rarely. And of course, Billy was very new to man on man love. He was a fast learner, and had served a terrific apprenticeship, but he was young. Was Billy ready for an exclusive? Did he even understand what that might mean at this point in his life? Dylan shuddered and wondered, “Am I too old for someone as young and innocent as Billy already?”
So the decision was made. He’d have both—and possibly others over the next few weeks. But, that meant that in a few days when Greg left for Greece, he wouldn’t have a live-in or on demand, flesh and blood partner. The fact that he couldn’t choose meant that he would be in fact still cruising—at Pelican and on Evermay. But, his expectations were changing. He really wanted another Ollie—but an Ollie who might become a life partner. Was he willing to wait for Billy and take his chances?
He’d definitely hire Sandy and see where that might develop. If it went well, he could invite Sandy to move into one of the quarters above the pool house. But, Dylan had the feeling that Sandy would always feel “kept”—and that doesn’t work in a relationship. He needed to find a way to make Sandy a partner as well as a paid trainer. Can he compartmentalize? If not, other trainers were available. He’d rather have Sandy as a partner, assuming he concluded Sandy was not a gold-digger.
And he would tell Billy that he was a “permanent” invitee to the Saturday evening parties at the mansion and Sunday sails on Evermay. That schedule would start in two weeks and continue every other week thereafter until the weather changed. He would explain to Billy that, given his age, experience, and the likelihood that he might want to experiment, the parties and sails would typically involve six to eight guys—and Billy should not consider himself attached to or exclusive with Dylan—although Dylan would be happy to be enjoying Billy anytime. Billy would find other partners easily. He would invite Billy to text when he wanted or needed some relief—or intimacy. But, he would make it clear that they were not exclusive while still convincing Billy that he was really special, because of course, he was. Actually, and uncharacteristically, he was going to tell Billy that he felt loved as well as pleasured by their experience. He wondered whether Billy’s “love-making” style of fucking would translate to the desire for one-on-one romance—or whether Billy could enjoy the variety of different partners. Only time would tell.
And, of course, there was Greg. He definitely had feelings for Greg—but Greg was leaving; he really had no reason to stay. Dylan knew that long distance relationships and “kept-man” relationships rarely were successful—particularly where the “kept man” was the top. Psychologically, it just didn’t work. Dylan was having a difficult time trying to imagine how a long term relationship could be built on a foundation where one of the two (presumably the sub) had “bought and paid for” the initial encounters and was financing the continuation. He wasn’t even sure that Grey thought in terms of money—perhaps that was a typical American response.
Greg was obviously a magnificent creature. He could be gentle and he could be a super-top. In many ways he was a grown up Billy—and perhaps a less jaded Sandy. He also had brains and entrepreneurial drive. He could have anyone he wanted. Was that his career—to be an ever-boy-man lover for hire? Dylan had no precedent, no history to look to—how do those relationships work out? But, he feared they just didn’t.
After a cooling swim, Greg left to drive the guys home. Everyone seemed content with Dylan’s spoken–and unspoken–plans. Dylan went into the office to read some of the day’s emails before he joined Greg for a light evening meal.
There was a message from his regular captain. On the previous day, when he had been hiking and climbing with his family at Maroon Bells, he had fallen, broken a hip and femur in several places, on a rocky outcropping, and was in traction at a hospital in Aspen. They wouldn’t cast for at least a few weeks after perhaps a few more surgeries. It would be at least a month, likely more, before he could return to Annapolis—and even then, he might need a cane or crutches for additional weeks. He regretted the inconvenience, suggested a friend who could handle Evermay if Dylan needed, and promised to return as soon as the medical team permitted.
Dylan then made one of his typical instant management decisions. He would ask Greg to stay on for another month or two. He was confident that Greg would stay as the Greek sailing season was typically very slow after September. Dylan was a very persuasive guy. So he was confident his bed would not be empty long. He would have time to consider how his relationship with Greg might play out. He was going to lay on the charm. And he was going to talk to Greg about the business. In the last days, Dylan had made some startling self-discoveries. He had changed. What could that mean for Greg?
(There are obviously more stories here, but they are not yet written. Let me know if and how you might like to see this develop. Incidentally, I am a sailor and have spent many years sailing from Kent Island and many nights enjoying St. Michael’s and Annapolis. I’d sure like to have an Evermay, fully equipped and manned, of course—with a Billy, a Sandy and a Greg. BD)