Dylan Thomas Merriweather III Ch. 04

Dylan Thomas Merriweather III Ch 04

Dylan and Greg: a developing relationship

Originally, the DTM series was conceived as a three part story. However, there have been requests for more, particularly because there were unresolved relationships--so here is a sequel. It is told from Greg's POV, the young Greek pilot-captain that Dylan had brought home from Greece. Readers might want to consider the first three chapters for deeper characterization and motivation--although this is a stand-alone story. All characters engaged in sexual activity are over 18. The story is entirely fiction. No AI was used in the composition of this story. © 2023, all rights reserved. Brunosden

[Recap: Dylan, a wealthy young power bottom, regularly seduces young men from the Naval Academy and St John's. After an Eastern Med summer cruise, where Dylan hired Greg as a "pilot" for his yacht (and top-fuck-buddy), Dylan has invited Greg back to Annapolis. Greg is not sure of his status although he spends most nights inside Dylan or tightly spooning Dylan in Dylan's bed. Dylan continues to cruise and seduce attractive young hung men. Many have told Greg that he is very special to Dylan, but.....]

Dylan has just offered me a four week (at least) extension on my agreement to be his cruiser-captain and FWB in Annapolis. We had met almost two months before when he was cruising in the Eastern Med. He needed a pilot to assist the captain in the deep, uncharted waters--and he wanted one who would play a second, unique role--at least in my experience--a live-in top who would anchor deep in him. Then, as his captain needed a few weeks for Coast Guard re-certification and vacation, he asked me to come back to Annapolis with him as pro-tem captain of his Evermay II.

He is a complex young guy. I'm still trying to understand him. He's in his thirties and, thanks to the untimely death of his father and grandfather, with significant inherited wealth--which he has vastly increased as a metals trader. He's a fearless risk-taker and a very hungry power bottom. He's eye candy--medium height, tanned, lightly muscled, blond and blue, with a long uncut dick. He turns heads with his handsome masculine appearance. Everything about him screams top and dom (voice, wealth, body language, aggressive business persona, even the size of his cock), but he really isn't either. He's a confirmed bottom, but a power bottom who orchestrates every sexual encounter. He loves to feel he's being handled and roughly, but in fact, that too is something he controls. He occasionally tops, but only to teach what he wants or to make a point. Thus, for someone like me, he's a dream come true in bed: a ready and willing bottom that I can manhandle all I want while I drink in his beauty and enjoy our comfortable day to day life.

I've been with him (and in him) virtually every day since he first interviewed me on the island of Simi. He is a terrific lay. Of course, we do it on his terms--he calls me, day or night, when he feels he needs to be filled, emptied or spooned. He's tight, responsive, and inventive. I've never had better--man or woman. He seems to be very afraid of commitment--although he is definitely out. He's alluded to a past relationship which broke badly, but I don't have all the gory details. I've seen him with a half dozen guys since he hired me--in addition to me--and he currently is dangling two new guys on sexual puppet-ropes: a muscular Russian immigrant upperclassman at St John's (Sandy, who is also a skilled masseur) and a brand new cadet at the Academy (Billy, who projects innocence and tenderness and is blessed with incredible beauty, innocent vulnerability and the biggest cock I've ever seen--which apparently he uses to Dylan's satisfaction). Actually, I'm not sure about Billy. Billy is a first year cadet on a short Academy leash. He can't respond as Dylan might want, but he's a beauty, a lover, and Dylan might be willing to make some sacrifices to keep this guy--although his past bad experience with a guy married to the U.S. Navy might suggest this is not wise.

Incidentally, I'm really not so hard on the eyes. I'm a little over six foot, taller than Dylan, with dark curly hair (longer than when I originally met him) and dark brown eyes. I've got really nice muscle definition and a long thick uncut cock. I graduated from the Polytechnic in Athens. Papa had intended that I would follow him into his commercial contracting business--but the sea called as it has so often to us Greeks, and my brother and I bought a charter boat with a big loan. I think I'm a disappointment. I'm sure Papa is assuming that I will get the sea out of my blood or that the boat will bankrupt me and I will return to home and his business. I'll be 30 in a week--time to think about the future, he keeps saying. Meanwhile, I've really enjoyed captaining and bedding charter customers, men and women. Sex is always better on the water. And my "captain's" uniform is typically a tight tee (with a giant logo: "Aye, Aye, Captain"), a white and blue bikini (the Greek flag colors), and a Greek fisherman's cap.

I left my younger brother in charge of our charter boat when I took Dylan's offer. We had one employee at that time--a beautiful young French woman who cooked and did guest cabins. Connie had bedded her almost immediately after we hired her at the beginning of the charter season, and they regularly occupy one cabin now. Connie was okay to let me go for a time--it gave him freedom of the boat with Sophia, and our charter season was just about over until next spring. My earnings from Dylan would easily carry us through the winter--so he could relax with Sophia and do the minor repairs that might be required before the next charter season begins.

Dylan's captain had yesterday notified him of a serious hiking injury (he had taken a family hiking vacation after the Coast Guard recertification course) that resulted in hospitalization. He would probably be out for the rest of the autumn season--thus Dylan's offer to keep me on as his replacement.

I'm theoretically "thinking" about the offer, but there is little doubt that I will take it. I'm falling for Dylan--and a few more weeks together will give me a chance to convince myself (and maybe him) that we belong together--or that we've had a good solid ride (at least I have) and it's time to move on. But "being together" may mean something different to him: a regular bedfellow, but with an open relationship understanding.

He's made the offer a little more complex however. He wants me to "read into" a position with his company. He seems to be suggesting that I need to join the business if I want to stay. I'm not at all sure that I'm ready for a suit--even if that is the price for a long term relationship. Besides, Dylan hasn't given any indication that he is considering exclusivity, let alone monogamy--with me or anyone else. All his hooks have told me that I'm very special to Dylan, but Dylan himself hasn't really given me that signal.

We are living in a large (inherited) Victorian pile of a house on a creek tributary to the Severn. It's totally remodeled and modern inside. Dylan runs his various businesses from a "control room" near his sleeping quarters and from an office-apartment over the newly-constructed pool house. Evermay II is docked on the river and is also equipped with a state of the art control room.

In the last few days, we've learned of several potential major disruptions in the metals business--an unexpected, announced uranium merger of rivals and a potential Chinese takeover of a rare earth metals producer in Africa. Dylan has been orchestrating responses--and so far, based on his smiles, comments and attitude, he's been making a good deal of money because of these disruptions, despite his inability to influence the outcomes.

Dylan has asked that a young trader, Tommy Wu, currently in the Singapore office, be temporarily reassigned to Annapolis as the liaison in the fast-paced trading business. Dylan intends to house him in the apartment over the pool house. I'm to pick him up at Dulles International later tomorrow. Based on a few stray comments, I guess that he's got a good body and that Dylan has had a sex with him. He's supposed to be our cobalt/rare earth metals expert trader. And I'm to study with him and begin to learn the trading business.

I've just taken Billy home--he and Dylan spent the afternoon together on the yacht, intertwined in each other. Dylan is glowing--but I continue to think that Billy will be just candy--he's good and sweet, but very young, inexperienced, saddled with hazing rules for this his first year--so he won't be readily available to Dylan. He'll be around again, but I doubt there is a long term future for him and Dylan. Billy is apparently a novice, but natural lover, extremely well-endowed and really handsome. But his unavailability has captured Dylan's imagination and ambition. It's the old story of the sweeter forbidden fruit particularly when offered by an angel with a colossal dick.

I'd almost finished putting the yacht to bed after a weekend sail on the Chesapeake, when Dylan called me to his room. That's when he dropped the offer to stay on and changed my immediate expectations. (He had just given me a going-away celebration.) I started to contemplate my response as I shut down the yacht electronics, when he called me to his room again. He wanted a joint shower, then probably more from me, and a night of tight spooning.

He was ready when I arrived, wrapped only in a towel. He looked good, really good. How could he have spent the day on the water with Billy loving him and look like this--hungry, open, and inviting? I stripped, pulled the towel from his waist, and gripped him into a tight squeeze. "Where did that come from, Greg?"

"I've been watching you all weekend with Billy. Sandy was okay, but he's not you." I threw him over my shoulder, caveman style, gripped one cheek in my left hand to stabilize him, and walked into the large glass-enclosed shower, doing my best imitation of a dom. I adjusted the water temp and spray pattern with my right as my left arm balanced him above me. He was squirming ineffectively. So I tapped him a few times on the ass to remind him who was in charge. Then I deposited him on his feet, spun him against the wall, and pulled his arms up and out and kicked his legs apart, using my hands on his cut to pull his ass into my gut. He was exactly where I wanted him.

I could tell he wanted aggression, and this time I was ready to deliver. I reached around, soaped his pecs and pinched his nips. They darkened and hardened. I teased them until he cried out in pleasure. Then it was down to his dick. I fisted it with soapy hands, stroked it and rubbed fingers over the sensitive head under the hood. He hissed and pushed back. So I reached for his balls and pulled them down and squeezed. He began to quiet. But, I held him still and squirted conditioner into his butt. My rigid cock followed and buried itself deeply within him with one long hard stroke, crowding and brushing the prostate as it plunged. I poked it hard, over and over. He gasped and backed into me, wiggling his ass muscles into my groin. My cock was so big that his wiggling was useless--I was in hard and tight. He was nailed good and proper. And my cock was rubbing his prostate, sending shock waves up his spine. My balls were so full they ached. Then he shot, covering the marble wall with cum. Hadn't he already had an afternoon of pleasure? How many times had Billy taken him? What the hell is his secret?

I pulled out, still rigid and moved us out of the shower. I toweled him roughly and again picked him up and carried him to the bed. I placed him belly down at the edge and stood behind him. Then I lubed and dove in again. Now I was pumped. My hips drove and drove as he slowly deepened into the mattress. My long hair fell into my eyes. I breathed him in--a combination of pine forest shower gel and the particular musk of an aroused male. It was heady stuff. Then I stretched out above him, pinning him with arms--and of course my hard-as-stone cock. He squeezed his glutes again, massaging me hard, pulling the spunk from my swollen balls. I shot hard, filled him with my cream, until it dripped down his inner thighs. I paused, reveling in the utter taking. Then, I dropped to my knees, spread his thighs, and licked up the spent cum, some even from inside his still open hole. When he was whistle-clean, I lifted him to the bed, shared my spunk with him in a deep kiss, before he fell into my spoon. I pulled him tight, nesting my cock in his cleft while my fingers cradled his balls. I was the dom he so desired. He was mine for the night. He even purred in contentment. Soon we were both asleep.

After breakfast the next morning, I left Dylan to his zoom calls and took the Rover to the airport. Before I left, he reminded me that he wanted me to learn everything I could from Tommy while he was here. The drive would give me time to think--about me, about him, about the possible us. Traffic was heavy. So it took almost two hours. I had plenty of time so wasn't concerned. By the time I parked in the VIP pickup section, I had reached some tentative conclusions. Of course, I would stay. I would try to see whether there might be a role for me in the company. And I would make it clear that I wanted Dylan on a long term basis--first by making him physically dependent and then towards the end of the four weeks with a verbal declaration of my desire. If at that time his response was not what I wanted, I was ready to return home. I had concluded that if Connie wanted to handle the boat alone (or with Sophia), I would back off and agree to work with Papa. All of this in a two hour drive!! Meanwhile, Dylan was going to be in for a wild ride on my cock for the next four weeks. I wasn't giving him up easily.

Tommy's flight was on time, and he emerged from arrivals a half hour later, carrying a soft duffel over his shoulder and, of course, a laptop. He was a tall lanky guy. He was at least 6-6 with a lightly developed chest and a very narrow waist, accented by his tight-fitting jeans and pale pink polo. He had dark black hair, styled but long and straight, dark eyes, and a deeply tanned complexion. His smile was wide and his teeth were gleaming white. He had large manicured hands and bulging guns and forearms. I was beginning to realize that the Singaporean Chinese community was growing big powerful young men, denying the ancestry of southern parts of China where men were smaller and much shorter. He was definitely a chick (or faggot) magnet. I understood already why Dylan had hired him.

I watched him as he walked down the departure ramp. I was dressed in captain's whites--a button up short sleeve shirt (with epaulets of rank), white shorts with a white webbed belt, and white boating shoes. My deep tan contrasted nicely. I held a sign with his name--but there was no doubt who my passenger was.

I approached and took his hand. He started a dominant squeeze, but I quickly reciprocated--I knew that game--and he backed off immediately. Thus, I was telling him that, although I was sent (like an employee or even a servant) to fetch him, I was his equal physically and in the hierarchy of Dylan's household. He may have taken Dylan a few times in Singapore, but I had been in Dylan's bed almost every night for close to two months. I wasn't going to bottom for Tommy. Tommy smiled. "Good to meet you, Greg. Let's get out of here. Thanks for coming for me." With those words, he reached around and tapped my shoulders, pulling me into him. (Did I detect a hidden sexual challenge?) I didn't even try to help him with the duffel.

We were at the Old Vic, as I had taken to calling it, by mid-afternoon. Sandy's bike was inside the gates--so Dylan was likely enjoying a massage--and probably more. So I showed Tommy to the apartment and invited him to unpack. Then I took him into the control room. "I presume you're familiar with this stuff. Feel free."

I pointed to the yacht. "Dylan has suggested we have drinks on board at 5. He knows you're jet-lagged and tonight will be an early night." The pool is heated if you want to refresh before then. Downstairs is everything you might need. Feel free to help yourself to the pantry and fridge. The gym is near Dylan's room and I presume he's having a massage. So I'll show you that later."

"Before you go, Greg. I'm curious. What is your role here?"

"I met Dylan in Greece last summer. He needed a pilot for his Eastern Med cruise. My brother and I were double-captaining our charter, so I felt I could accommodate Dylan's request. After several weeks, he invited me back here. I've been living here with him since." I realized that I was deliberately misleading Tommy at this point. I didn't want to have to eat crow later so I added, "Dylan and I are FWBs. He still sees other guys and so do I. I captain the yacht when we go out. But, I do live here--mostly in his room and his bed, although I have another room--and the captain's quarters on the yacht. He's asked me to stay indefinitely and has asked me to shadow you while you are here to learn everything I can."

"Thanks for the honesty. I have had the pleasure of Dylan in Singapore--but I don't have any delusions that they were anything but a hook of convenience. I'll be happy to show you the ropes--and with Dylan's permission, maybe something more. I'm not your competitor, but I'd like to be your friend."

My god, he was already coming on to me. Now I understood why Dylan liked his confident, aggressive style.

"I'll check with Dylan. I'm an equal opportunity companion. And I'm always open to new adventures and new ways of doing things. See you at 5."

As I walked back toward the house, Sandy emerged and was walking toward his bike. He looked tired and spent. Several jean buttons were open and his shirt tails were hanging limply. Dylan is a demanding massage patient--and a much more demanding "full service" client. "Hi, Sandy. How is it going?"

"Oh, hello, Greg. I didn't know you were home. Dylan said you were doing airport duty."

"We just got here and I spent a few minutes getting Tommy accustomed to the place."

"Is that how we are describing it these days? I seem to remember that you showed me around a bit also."

"Tommy is a specialist trader from Singapore. I don't know much beyond that. Can I give you a ride home? It's really warm this afternoon. Your bike will fit easily on the rack behind the Rover."

"Thanks, Greg. I could use a lift. Dylan is the most demanding client I've ever had. I'm wrung out. And worn out." So I quickly drove him home.

Later we had drinks and "heavy" appetizers on board the yacht. Dylan was pumped for some reason. But, Tommy was obviously almost unconscious from the long flights and time change. So we closed up early. There was really only one substantive conversation--when Dylan made it clear to Tommy that I was to be glued to him for the next month. "I expect that when you return to Singapore, you and Greg will be able to run that part of the trades 24/7 and interchangeably. Make sure he understands everything you do and why you do it. You will make or break each other after then." Tommy rose and started out, but overheard Dylan's last comment. Dylan continued, "Somehow I think you may be breaking in each other even before then. I saw the way he looked at you." Tommy smiled at me and left for his apartment.

"Dylan, I guess I'm a little different from you. For the time being, you are enough for me. I don't need extra-curricular activities. And I don't need you to find my hooks. I'm already fighting them off."

"Well, if you change your mind, you have my permission. Just be sure to wrap. I'm not changing my expectations of you at all. I want you available, often and without protection."