On Boss' Yacht
At age 18 I landed the best job that a teenager could hope for. The job was at an auto plant and I was thrilled. My mother worked at the plant in the offices and pulled some strings to get me in. At 18 I was making great money and I loved my job and co-workers. I even liked my bosses.
Since my mother knew all the upper management I got a job in an easy area doing light labor. My mother's management buddies would stop out occasionally and shoot the shit with me, and I like that. I especially liked it when her friend Rich would come visit me. Rich was the highest ranking manager in my department. For some reason he took a liking to me, I assumed that it was because he knew my mom. I was aware that I was gay at the time and I was comfortable with that. I was not an obvious gay kid, but I was very stylish in the way I dressed (most workers wore dirty clothes but I wore nicer clothes and was always coordinated). I was hired in the summer and I wore tight tank tops and shorts. I loved showing off my chest which is covered with thick hair. I guess that Rich liked the way I looked because he visited at least 3 times a week.
Rich was a very masculine man and about 50 years old. He had broad shoulders and looked like a guy that played football as a kid. Rich's hair was brown and he was bald on top but combed the side over to cover the top of his head. He had a cute, round face and a sexy smile. His body was slightly overweight but he was firm, even his belly was firm. The nicest thing about Rich was his chest, it was covered in dark hair speckled with grey. You could see the hair peeking out from the top of his shirt.
Anytime Rich would stop and visit we would talk for at least ten minutes. While he was there we would talk about various things. He would often ask if I had a girl friend yet, to this I would always answer "no." I never knew why he asked me this. One day I found out when he said "you should meet my daughter, you guys would get along great." To that I said "that might be nice" just to be polite. After I said that he invited me out on his boat for that weekend. I didn't want to meet his daughter but I did want to see him with less clothes on so I said "sure, I'd love it." Plans were made and that weekend I went to the marina to meet his daughter and go out on the boat.
I arrived at his boat promptly at noon. I smiled when I saw Rich and waved hello. His boat was huge, it looked like it was brand new. After getting onto the boat I looked around discreetly. I was looking for his daughter because I wanted to know what I was getting into. Rich could tell what I was doing, he said "I have some bad news, my daughter had plans for today and couldn't break them. Its just going to be the two of us today, if that's okay with you?" I could tell from that moment that the day was going to be more than fishing and talking. To his question I answered "great" and we then prepared to depart.
We hadn't been 50 yards out when I was asked if I'd like a beer. I took the beer and drank it as I enjoyed the view of the cape and of Rich's crotch. His swim trunks were just long enough to conceal his package. I stared at the area every chance I got. Rich seemed oblivious to my deep stare as he manned the captain's controls. After about 45 minutes of travel and light conversation we stopped and dropped anchor. I couldn't see another boat in any direction. Once the anchor was dropped Rich removed his shirt exposing his tan torso thick with long dark hairs. He reached for the sunscreen and began applying it to his arms and face. "Can you put this shit on my back" he asked. "Sure" I eagerly responded. I filled my hand with white lotion and I began rubbing his back slowly. As I applied the sunscreen I started getting aroused. I didn't know what to do, I figured that I would just slow down and maybe it would go down soon. I was wrong! Rich thanked me and turned around to give me the sunscreen to apply onto myself. He noticed my half-erect cock, but he didn't say anything. He just said "turn around and I'll get your back now." I removed my shirt and turned around. He began massaging my back with his hands. The manner in which he did this seemed like more than applying sunscreen lotion. His movements were slow and tender. He rubbed in the lotion for a long time, he even got the back of my legs. By the time he was finished I was totally erect! Again he didn't say a word about it.
The two of us began fishing off the back of the boat clothed only in swim trunks. I could feel his eyes on me and when he wasn't staring at me I was staring at him. Conversation was light but pleasant. After Rich had finished his 3rd beer he stood up to get another one for us. Before he got the beers I heard something. I turned around and I saw Rich pissing off the boat in the front. I could only see his back and a stream of piss but I was again aroused by the thought of him holding his meat. He packed up his cock and returned with two fresh beers. When he sat down his shorts no longer covered his whole package. His balls were almost completely exposed. The huge, hairy sacks caught my eye and I couldn't remove my eyes from them. My cock stood at complete attention now and I knew that I would not be able to hide this. My cock was over 7" and in the loose swim trunks I formed a sizeable tent. I grew concerned about this. To get away from the situation I excused myself and went to the front of the boat and tried to piss. I couldn't, I was too hard. And when I returned my secret was over. As a walked back to my chair Rich asked "what's the matter, too hard?" I was shocked! I walked up and saw that I wasn't the only one with a hard on.
Rich was sitting just as he was when I had left, only now his cock was out and he was playing with it. Rich's thick meat was swaying with the waves. He had about 8 1/2" and the cock was thick from base to tip. The head was like a perfect mushroom. Rich stood up with his great big meat out and removed his swim trucks completely. He said "it's always nicer to fish in the nude, why don't you get naked." I didn't argue, I did as he asked as quickly as I could. "Nice cock" replied Rich. "Thanks, you too." No sooner than I finished my sentence Rich lowered himself to my crotch and began sucking me. I moaned as my inches were being serviced. He took my cock down his throat with ease. He pumped his face on my cock hard and fast. As he sucked he jacked his own meat.
There I was in the middle of nowhere on a $500,000 boat getting head from my boss. I enjoyed the great head and I enjoyed my surroundings. I'd never had sex in such a open area.
"I want to suck you" I said, and without Rich missing a stroke I was lying on the floor of the boat 69ing with him. As his cock entered my mouth I could taste his precum, I swallowed that as well as the rest of his cock immediately. Sucking went on for at least ten minutes until Rich stopped and stood up so he could rest briefly. Rich rested, I did not. He was facing away from me so I licked what was nearest to me. My tongue attacked his ass crack like a blitzkrieg. I pushed him over the side of the boat so I could get in deeper. I licked his sweet, hairy asshole until I made him scream in ecstasy. Every so often I would reach around him and collect his precum for savoring. Rich loved me to eat his asshole. After only five minutes of sucking his ass he warned me that he was going to shoot. I turned him around and said "I want it!" I stroked his cock off rapidly. He shot his enormous load onto my face and into my mouth. He then descended on me and sucked my lips with his. We savored the hot load together for many minutes in the hot sun.
"What now?" I asked after a few moments of panting for breath. Rich replied "Don't worry, kid, we'll figure something out" with a sly grin on his gorgeous face. After that hopeful response he put his swim trunks on and resumed the activities of fishing. As we fished I noticed two other yachts nearing. The nautical treasures that approached were manned by treasures of their own. On first yacht that came into close view was two stunning men in their late 50's. The other was manned by a guy about 40. The owners of these yachts, including Rich, spoke kind words back and forth. Soon this private spot on the water became a party hangout.
The guys from the other boats tied up to Rich's and came aboard after we all finished fishing and getting showered down below the deck of the yacht. I had to shower alone, much to my disappointment, because Rich had to stay and talk to his new buddies. The sun had set by this point and I was sure that we would have to stay on the water all night. I was right! The five of us drank beer and partied well into the night. Rich became intoxicated first and he "spilled the beans" about what we had done earlier that afternoon. Upon hearing this Jon, Dave, and Joe spoke simultaneously, "REALLY!" Jon was 55, 5'10" tall, heavy, hairy (even on the back). Dave was 60 and in good shape, 6' tall, slightly hairy, and very business-like. Joe was 40 years old and the charming one of the three. Joe had the cutest round face and a sexy, chunky frame.
After the "REALLY" was spoken the questions began firing a me from three different angles. "How do you know anything about that sort of thing" asked Jon. I fielded his question and prepared for others. After the other questions came I began to explain my position as best as I could without saying that I was wrong (because I am not ashamed of anything I do). The guys reacted to me very differently than I thought they would. Dave spoke out "that sounds interesting." Then Jon said "even fun!" Joe didn't say a word, but when I looked over at him I knew that he didn't have a problem with a guy sucking another guy's cock. How I knew was that he had his cock out and was playing with it. My eyes bulged out of their sockets, and the others surprised me even further by following Joe's lead and exposing their lovely cocks. How did I get so lucky I asked myself.
I surmised that I didn't need to ask permission, so I got on my knees and was a good boy. First I opened my mouth wide for Dave, whose cock stood fully erect and measuring 9" or more (and he was uncut, with lots of foreskin). I received his meat willingly, I was able to get most of it down on the first stroke. I sucked him hard and fast, almost like I was trying to get him off quickly. I wasn't though, I wanted this dream to last all night. As I serviced Dave the other guys watched and played with their tools. The heat of the moment got to Joe soon and he joined me on the deck of the yacht and began sucking off Jon. "Looks like fun guys" said Dave while he watched me suck him and Joe suck Jon. "I'd like ta try it too!" Dave too knelt down after he removed his long cock from my mouth. Rich promptly filled up his wanting mouth. That left me alone to watch, and watch I did. I didn't even want to blink in fear that I might miss a blow. I wandered over against side of the boat and sat with my eyes fixated on the action being performed in front of me. I focused on the exchange of passion between Dave and Rich. I assumed that this cock sucking was something new to these men but Dave had apparently participated in gay sex before (or at least fantasized about it). Dave was experienced in the field of sucking cock. He worked Rich's cock like a pro, and his treat to Rich was being appreciated deeply. Rich moaned loudly, and begged Dave for deeper head. His request was honored and the cock disappeared even further. I wanted to share the feeling of Dave's mouth but I wasn't about to upset the situation, plus I figured that my time would come.
The scene with Jon and Joe was just as hot and erotic. They had progressed into a nice 69 position sucking and fingering each other's asshole. The two men writhed in passion as the fingers disappeared into the rumps. I jacked my own meat while I watched this and became unable to resist entering the mix. Without asking I approached Jon and Joe; I joined them on the floor of the boat and began sucking on Jon's ass. He rocked his hips and spread his cheeks with his hands as I serviced his gorgeous pump pot. He wanted it! I wanted to give it to him. So I did! I got up on my knees and entered Jon without any assistance from lube of any kind. I slid into him easily even though the hole was utterly the tightest ass I'd ever had the pleasure of filling. He took my 7" like a man. Jon wanted to take my cock in different positions so he got up on his hands and knees. Joe crawled over near Jon's behind to watch this fuck show, which left an opening that Jon wanted filled. "Give me your cocks" Jon demanded of Rich and Dave. They both eagerly walked over to Jon's face. Then they stood there in front of him giving Jon the choice of who to do first. He grabbed both cocks and sucked Rich's for a few strokes then to Dave's for a few. When he wasn't sucking the one man he would jerk their dick hard and fast. Jon wanted to filled with cum.
I'd say that Jon got his wish of being filled with cum. I blew my load right up his tight ass after I had been fucking him hard for over 15 minutes. I shook like a madman when I blew it and Jon rammed his ass closer to me as I was shooting my cum in him. One fuck wasn't enough for Jon though. He threw Rich to the ground and sat on his rod. While he was atop the boner he rode up and down fast. I watched Rich's 8 1/2" enter Jon and then totally disappear over and over. The sight made me hot again (even after just cumming a few minutes prior). I found myself massaging my own asshole with my finger. As I warmed my asshole up I sucked Dave to an erect state once again. The hung man shivered at every movement of my tongue on his long rod. It kept on growing and growing; I assume he knew what he was going to get from me. Dave descended to meet me on the boat deck. He softly sucked me before raising my legs up for easier entry. Dave was like a God as he kneeled between my legs. So big and strong and about to take whatever he wanted. He did just that! He aimed his glorious 9 uncut inches at my point of entry and busted into me. Without a warm up he began banging the hell out of me. There at my ass he jammed all 9 plus inches into my young, almost virgin, hole. Balls deep he was and the sheer size of him was splitting me apart. The pain was immense, but the pleasure was also. I adjusted to the feeling after a few minutes of relentless fucking. He boned me until the inevitable happened. When it was time for him to blow his cum he removed the rod from my ass and fed it to my mouth. I sucked it a few seconds and I then tasted him for the first time that night. His load was tasty as I ever remember a load ever tasting. I felt him get soft in my mouth and I enjoyed sucking his limp meat. The foreskin began to return over the head and I had my tongue inside it. Dave was finished after that and he went across the boat to a lounge chair.
I wasn't done being dominated yet however. Joe gathered me in his arms and then bent me over for more ass abuse. He fucked me for over 10 minutes. He stuck me deep. Joe's cock wasn't as long as Dave's but he certainly was thick! The thickness of his rod stretched me out in another way from the way Dave had. After Joe blew his load in me Jon found my hole with his old man meat. He violated me like I was a dirty whore (I guess I was at this point). While Jon banged my ass Rich filled my mouth with his huge manhood. Rich just fucked my face with all his might. He lasted over 5 minutes and then he sank his cock all the way down my gagging throat and shot his hot jiz. I couldn't even taste it because his piss hole was so far inside me. He sight of Rich losing his cum to my mouth got Jon hot as well. I could tell that I was going to be taking his cum soon. I braced myself and jabbed my ass into him as he did when I was fucking him. That took him over the edge. The cum spilled out of his cock at a staggering pace. The milky cum oozed out of my ass an ran down my leg. My ass now had two loads in it and I had swallowed two.
I spent that night in the arms of four hot men. We all slept in the same bed in the living quarters under Rich's deck. The bed was large but we still had to stay close. The gentle movement of all those mature bodies was a thrill. I wanted to sit on all their cocks as they slept but I was not going to put my ass through any more. I found that fingering them satisfied me very well. I fingered until I needed more. I rolled them over and ate each of their asses as they slept off their drunkenness. Dave was the last one I serviced anally that night, and after I ate him out I placed his enormous cock in my mouth and went to sleep with him in my mouth.
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