Sam slid his hands around to my ass and began kneading my cheeks. As one of his fingers meandered toward my needy hole, I again asked, “What did you have in mind?”
Sam finally spoke, “How about we head below and see what develops?”
I leaned into his ear and whispered, “I need you inside me now.”
As I backed away, I pulled him toward the steps, and we headed down below. Once we were inside, I tore off his clothes and pushed him down onto the bed. With him watching intently, I did a slow strip-tease removing my thong. After stepping out of it, I crawled up on the bed and kissed him on the lips. I then slowly turned away from him and mounted his rigid cock in a reverse cowboy position. Sliding down his stiff cock, I kept going until it bottomed out in my warm, slick ass. I began a slow pumping action, taking him out until the tip was just inside and then back down until he was fully buried. Sam slowly moved his hands to my hips and grabbed ahold, as I kept up a slow full stroke.
Sam began to whimper, and the begged, “Please go faster, I’m so close.”
I turned my head back toward him and smiled while saying, “This is your reward, do you want it to end too fast?”
“No, but I was hoping for a two-part reward, ” Sam grunted as he was close to cumming.
I came to a stop with him balls-deep inside me, and inquired, “What else did you have in mind, lover?”
Sam pleaded, “Please keep moving!”
I asked again, “Tell me what else you want, and I’ll get started again.”
Sam quickly responded, “I was hoping that you’d fuck me like you did Matt.”
I started moving again, and Sam sighed as his cock swelled, and he pushed up into me hard. His hot cum filled my worn ass, and I nearly came myself from his firm intrusion.
I sat still, resting on his pelvis as his cock continued to pulse those last few times. As I felt his hard-on soften, I stayed in place, as his cum started to leak from my stretched anal ring. When Sam felt himself slipping from me, he asked, “Will you fuck me now, Steve?”
“Sure,” I replied, as I lifted off his depleted penis and coated him with his own semen. I turned and pushed his legs back, to find a medium-sized plug occupying his wanton anus. I eased it out and then used his own cum to lubricate him. I slipped in first two, then three fingers to get him ready for a good fucking. Sam seemed to be enjoying the penetration from my digits, so I kept it up until he began to shudder.
As a few small squirts released from his soft cock, he begged, “Fuck me hard now!”
I rubbed my own cock in his cum for extra lubrication, before sliding inside for a ride. Starting off slow brought about several shouts of, “Faster, faster!”
I picked up the pace and pinned his legs back onto his chest as my pelvis smashed into his ass repeatedly. Sam was now babbling incoherently with his eyes closed with drool running from his lips. I felt contractions in his rectum from yet another orgasm and noticed another couple of small squirts emanating from his flaccid penis. His ongoing climax had me seriously close to my own, so I started pounding his rump with abandon. Up until now, his noises were few and gurgled, but as I hammered away, he began to yelp like a dog.
My climax was now imminent, as my cock-head began to swell in those pre-orgasm seconds. Sam came again while screaming at the top of his lungs. My peak was right behind his as I pushed a sizeable load of my spunk into his sloppy ass. His screaming stopped as I withdrew from him and dropped onto the bed by his side. We both lie there recovering from our animalistic session, as I panted like I’d just run a marathon. Still on my belly and breathing hard, Sam turned to me, and asked, “May I kiss you?”
I rolled onto my side and faced him, then leaned into him for a soft kiss. Sam’s reaction was to wrap his arms around me and pull me close for some tonsil diving. I let him lead so that I didn’t come across too strong. I sometimes get a little over-zealous when kissing, and it leads my partner to believe there is more to it than just sex. The kissing slowly ebbed, and as we separated, Sam asked, “Could we do this again next Thursday?”
I smiled before replying, “Of course, as long as you make the first catch.” We both laughed at the comment, and he moved in for some more dueling tongues. After a few more minutes, Sam stopped and commented, “I’d better let you get back topside. I’m sure everyone thinks that I’m hogging your sweet ass.”
We rolled apart, and I walked to the head, where I cleaned up a little before donning a new white thong. Sam was waiting patiently outside as I opened the door to head up to the deck. He leaned in for one more wet kiss and a quick squeeze of my cock before we passed.
Topside, the other guys were busy fishing as I mingled and took drink orders. I dropped off their requests and let them play with my goodies before heading back to see Grandpa. He was doing a little fishing of his own and showed me a few pictures of the catches they made while I was below. Flipping through the pics on his phone, I said amazed, “You really do more fishing on the Thursday cruises.”
Grandpa replied, “I told you so. You have had them more active today than I’ve seen in the last couple of months. I think that they’ve been in a funk since they lost their friend Evan.”
“He was the fifth of this group?” I inquired.
“Yes,” Grandpa responded. “Evan was not only a longtime friend, but he was sort of the sexual leader of this group. He initiated most of the sex and was the most daring in his choice of attire.”
“So all four of them are basically shy and need a fifth that will push them where they really want to go,” I implied.
Grandpa answered, “You hit the nail on the head, Stevie. That was very observant of you to pick up on that.”
“I may be majoring in business, but that psychology minor does wonders for reading people. Have you suggested Mike from the Tuesday group?” I queried.
“Mike was one of the guy’s on the list, but I’d rather not move people from one day to another if I can help it,” Grandpa explained.
“So why haven’t you made Saturday a permanent group like the other days?” I asked.
“Since you asked,” Grandpa started, “Saturday is my test day for new candidates. It gives people who’ve heard about the cruise, through friends, a chance to try it out. Of course, all of them are tested before they’re allowed to come aboard. It takes a lot of time to get into these groups. No one knows this yet, but I’m seriously considering a Sunday cruise also, which would be another fixed group. Now with you here, my problem will be keeping the regulars away from the Saturday cruise.”
“Well, isn’t that a tough problem to have,” I said as we both cracked up.
Looking at his watch, Grandpa announced, “It’s time to stow the gear and get headed back. Go tell everyone, and help them get everything stowed before we get going.”
I headed toward the guys and told each of them that it was time to pack up as Grandpa fired up the engines. As I helped them gather their gear, there was plenty of ass and cock petting. Even Sam, who couldn’t blow anything more than dust from his floating sack, enjoyed feeling me all over.
The one that I might still have a little semen left to share was Cesar because all he got was a blow-job so far. I flirted a little harder with him, and he did enjoy the attention, but finally said, “I appreciate the offer for some more of your sexy body, but once is plenty for me. Maybe next week I delve into that ass that everyone has been raving about. Although I’m more interested in how you fucked Matt and Sam into multiple orgasmic submission,” as he traced the outline of my hardening cock.
“Next week, you show up a little early, and we’ll explore each other’s back doors intently,” I whispered as I leaned into his ear and cupped his scrotum.
As I groped him, he mumbled, “Okay, that sounds great,” before kissing me and backing away. With a forty-minute ride ahead, I was hoping to get a little more sex time to bump up my tips. However, the guys seemed happy just talking and having a beer. We all sat around with me still in just my thong and legs spread. It was Joe that felt my thigh and asked, “How do you keep your legs so smooth?”
“I guess I’m just lucky because I’ve never had much body hair. I do shave myself the morning of the cruises and coat myself liberally in baby oil,” I offered.
Joe continued to caress my thigh while Sam did the same to the other. My erection had grown noticeably from their efforts as Matt moved behind me and began pinching my nipples. As the head of my penis popped out from under the edge of my thong, Matt whispered, “just relax and enjoy.
Joe and Sam slowly removed my thong as Cesar slid down in front of me and took my cock in his mouth. Matt released my nipples as Joe and Sam took them into their mouths. With Cesar sucking my rigid cock down his throat and my nipples getting sucked and nibbled, I was in heaven. With my head reeling back, Matt took the opportunity to stick his tongue in my mouth. All the attention was fantastic, but since I had just cum, it wasn’t going to be that easy for my admirers.
I was getting into it though, as my right hand went to the back of Matt’s head to get deeper in his mouth. The left hand went to Joe’s head and pressed him harder into my left breast. Cesar was pushing my pole down his throat like a master, and I was right in the zone. As I moaned softly into Matt’s mouth, I felt my chair tilt back until I was horizontal. Matt stayed with me as I was lowered, as well as Joe and Sam.
Cesar released my hard-on and pushed my legs back while pulling my ass past the edge of the chair. WIth Joe and Sam holding my legs out of the way, Cesar pressed his tongue between my cheeks. He was another one with a snake-like oral appendage, that knew how to use it properly. He was clearly aware that my anal entrance was raw and swollen from overuse, so he was quite gentle. Even with light licks, he was pushing me ever closer to my final climax of the day. As his oral ministrations continued, Cesar’s hand was tenuously polishing the head of my penis.
I was moving over the top and heading toward a massive peak, as my entire body began to flutter. The vibrations steadily increased until they became tremors, and I was physically flopping on the chair. Joe and Sam had my nipples harder, and more sensitive than I ever remember them getting. They had been gnawing on them earlier, but with the increased sensitivity, they were simply flicking them with their tongues now. Matt had been doing the same thing with my lips and had them so tender that simple kissing was dialing up my oncoming climax.
It was as if Cesar could sense the contractions of my pelvis seconds before they started. He suddenly moved his mouth to my pulsing pecker, while continuing to rub my anus with a moist finger. I would never have known if it wasn’t for feeling his lips on my scrotum as he pushed me into his gullet. Just as he made that move, I convulsed hard into him and shot whatever semen I had left into his waiting belly. The glorious strain of those last few thrusts rendered me unconscious for the next few minutes.
I awoke to the guys all sitting around me. As they were drinking their beers, and sharing their stories of our debauchery with each other. When they saw that I was awake, they tilted my chair up slowly and handed me a beer. They continued their tales, and I listened intently as if I hadn’t been there myself. As the stories continued, Joe handed me my clothes since we were closing in on the land. Once I was dressed, Grandpa called down to say that we need to prep for docking. We all took our places as Grandpa eased the boat into the slip. Once it was tied off, I brought everyone’s belongings topside as we all said our goodbyes.
I went back to closing things up after they all left. About thirty minutes later, Grandpa and I were sitting on the deck enjoying one more beer. Always looking for his input, I asked, “So how do you think I did on this one?”
Grandpa leaned forward and handed me two envelopes. The first was my pay from him and the second had ‘Stevie’s Tips’ written across it in red. I opened the envelope to find twelve hundred dollars. I stuttered, “What the… hell,”
Grandpa asked me, “How do you think you did?” I just shook my head in disbelief as he continued, “You did more for those guys in one afternoon than anyone has since Evan died.” As tears formed in my eyes, he lifted my head up and proclaimed, “You and your friendly, loving nature, brought four men out of their funk and they will be forever grateful. In fact, they spoke to me about paying off your college tuition in full. So I ask you again, how do you think you did?”
Unable to form any intelligible words through the lump in my throat, I simply shook my head. Grandpa took that as a ‘yes, I did good’ and patted me on the back as I thought about their inconceivable gift. We sat for a long time, and after a while, I was able to form words again. The first thing from my mouth was, “How, and why would they do such a thing for a near stranger?”
Grandpa leaned back in his chair as if bracing himself for the telling of a long story. “It all goes back to their own struggles as gay men trying to hide their proclivities in an unaccepting world. They all were married at some point and dealt with all the conflicts that brought. So they are all keenly aware of the encounters that you will face even with a more accepting society. As for the ‘how,’ all of my patrons are incredibly wealthy and quite generous. That is one of the main reasons that I chose you for this job over anyone else. I knew that you could be discrete.”
I watched Grandpa intently as he spoke. When he was finished, I managed, “How do I begin to thank them for this amazing gift?”
“You owe them nothing. This is their gift to you for brightening their lives. Even if it’s only for a handful of days through the summer,” Grandpa reiterated. When he finished talking, he got up and started to close up the boat. I automatically followed his lead, and in less than five minutes, we were walking down the dock toward our cars.
As we continued down the dock, I inquired, “So how does Saturday work? Is it a first-come, first-served thing?”
“Basically that’s the way it works,” Grandpa answered, but added, “It’s usually the same five guys as always. Sometimes one can’t come so we get another, but they’ve all been tested and referred by another member. The problem is that word of your popularity has spread through our members, and there’s no telling who will show now.”
“So I guess there’s no use in asking you about any of them since we don’t know exactly who’s coming,” I theorized.
Grandpa got a twinkle in his eye before stating, “There is one that you should know about. Ian is about six feet two inches and is an easy-going, but popular guy for one reason. You see, Ian has an eleven-inch cock that is nearly as big around as a coke can. So, if Ian shows up, make sure you go easy on the anal that day. Also, make sure he’s your last of the day.”
I replied, “I completely understand. We have a guy at school like that, and he can ruin you for days if he takes too long to cum.”
“So other than that, enjoy the hardware store tomorrow, and I’ll see you Saturday at the same time,” Grandpa said, as he got in his car and took off.
During my drive home, I went from wondering whether I genuinely deserved these gifts to utter joy at having received them. One thing was sure, I’d have to do my best for these guys throughout the rest of the summer. I felt that I hadn’t really earned them yet, but I would make sure that I did before it was over.
