After curling in winter, I decided I needed something to do during the summer to fill not only the evenings but the days as well as high school was out. To kill my summer of isolation in Nova Scotia [Canada] I joined the local sailing club. Well, more accurately, my mother signed me up as, unlike me, she made friends hand over first and she wanted to keep me busy and in NS sailing is popular summer sport.
I had taken sailing lessons every summer, as we would go to Nova Scotia where my mother was from and I would be enrolled in a program in Halifax. The cool thing about sailing is that when you are a kid taking lessons (which your parents pay for) you sail on small one and two person boats. But on Wednesdays and Sundays there was always a regatta and adults with hundred thousand dollar boats would be looking for crew, so you could sail on a big yacht (that your parents could never afford) and, with the right boat and crew, share in being a victor in some races.
The town I was in was much smaller than Halifax, so the yachts were smaller and there were no courses to learn how to sail, but the game was the same and as someone who could sail I quickly, with my mom's help, found a yacht to crew on. I was quickly part of the club and accepted by all.
With no junior sailing program, the only kids at the club were the children of people who owned yachts, plus me. Being a small town there were few children of members of the sailing club and all were younger than me. But I soon bonded with all of them and we began to hang out not only at the yacht club but also in the town.
As they were all 12 and 13 years old, they were keenly interested in each other's crotches and admittedly I was the one who introduced them to the wrestling game that I had played with my friends when I was that age. It involved wrestling on the grass, but everything was fair game, so soon we were all grabbing each other's cocks presumably to force the person who had pinned us to let us up (but we never grabbed hard, it was more about checking out what the other boy had in terms of cock and balls size).
It never proceeded beyond crotch grabbing. I thought about it with one or two of the boys who was very hot (well hot for a 12/13 year old) but I was worried that if I tried anything more it would get back to their parents and, at 16 now, I would get in serious trouble as the parents would assume (rightly so) that I was the instigator and it was not about youthful horsing around (which for me it wasn't).
With one of the kids, who wasn't from our town and lived on a schooner with his parents, I let things go a little further, though I instantly regretted it and felt ashamed. He and his family arrived mid-summer and, after docking at the club and getting fuel and supplies, they made arrangements with someone further down the river to let them dock their boat on a private pier (that way they didn't have to pay for mooring fees, as the family seem to be spending the year sailing around and had a limited budget). During one weekend I biked down to where his boat was tied up at the dock, about five minutes away from the yacht club which was 30 minutes away from my town. We had agreed to go swimming.
When it came time to change, his mom told us to go into the galley, which is a nautical name for kitchen and theirs was at the back of the boat behind a door so was one of the few places that afforded privacy on their boat. I suspect his mom only suggested that as a courtesy to me, cause when they first arrived at the club I had seen them all change and shower in the open with no modesty, which is something I guess you sacrifice when you live 24/7 on a boat and travel together.
We changed into our bathing suits in the galley. He was too young to cum so I had no interest in his cock so I largely ignored him as I changed (as I had when he showered at the club under the outside nozzle), but he clearly had an interest in mine as when I finally looked over he was, with no embarrassment, watching me change
Knowing he was watching me, I initially wanted to hide myself. I had pubes and a bigger cock and balls. I wasn't sure what he would think but then I realized he lived on this boat with his parents and went from yacht club to camp ground where he showered in public areas with other people living on their boats and probably had seen lots of people naked. He was probably aware of much more than I was giving him credit (or had probably seen myself) and I had no need to hide myself.
So once I was fully naked I stayed that way, making myself busy with stuff I would never have done at home or in a locker-room, like folding my clothes neatly as I took them off. Not only did he unabashedly stare at me, as he undressed it became obvious he had a hard-on. Even though his boy cock in his yellow briefs had no appeal to me, being looked at sexually by him was a turn-on for me and soon my cock had gone rock solid. As I said, I was struggling with the thought of hiding it by turning away or putting on my swim trunks but he was not hiding his erection that was tenting his briefs so I didn't.
He was only 12, but he was clearly not shy, I guess from living on a boat with parents who were probably what my parents would call 'hippies'. He walked over to me and reached out and wrapped his little hand around my cock.
He looked into my eyes and all I could think to do was smile so he knew I was non-threatening. I reached down and wrapped my hand around his hand and moved it up and down on my cock. When I let go he continued. I was totally enjoying being wanked even if it was by the small hands of a pre-pubescent boy four years younger than me.
Without telling him to, he moved his other hand to my balls and played with them before running it over my chest and stomach and legs, feeling the hair that was growing in these places. He ran his fingers through my pubes, which he didn't have, and along the treasure trail that had just that summer emerged between my belly button and my pubes.
Now that he had both hands on me, I couldn't help but touch him. I don't know if it was me being reciprocal or I wanted to touch him, but soon both my hands were all over his briefs, feeling his ass, his hips, his small cock and balls and even up between his legs. It was like having a play toy that was anatomically correct and, it I am being honest, I was turned on feeling him through his briefs.
I knew I was about to cum and while I was not sure how he would react I didn't want him to stop. I left one hand on his cock and balls, which fit neatly into the palm of my hand, and I took my other hand and cupped it under the head of my cock. As he continued his steady stroking my hard cock I unloaded my cum into my own hand. Being inexperienced, as soon as I started to cum he stopped moving his hand so I took my hand off his cock and balls and placed it around his hand to make him keep moving (I was afraid to speak cause his parents would hear as being on a boat it was not large and sound travelled - in fact I made no noise when he wanked me even when I came).
Once I was finished I let go of his hand. I was surprised when he didn't let go of my cock. I was more surprised when he leant forward and stuck his tongue into the cum load I had in my hand to taste it.
After that he let go of my cock and went and put on his bathing suit, I went to the sink and washed the cum down the drain. I then put on my swimming suit and we had a great day swimming and dinner with his parents before biking home. He never mentioned what we had done.
We were friendly at the club but I turned down all his suggestions I come over to swim again. I recognized myself in this boy, he was curious and eager to please, but I couldn't bring myself to help him with his desires as he was only 12 and I felt guilty about what we had done this one time.
Maybe it was selfishness, because he couldn't cum and by then I wanted cum in my mouth or a cock in my ass; maybe it was a new sense of maturity as I considered that someone with 'grown-up' experience like me would rush someone like him along too quickly; or maybe I was becoming a prude, I was 16 and anyone under 13 I thought of as a kid and immature so part of me thought he had no clue what he was doing (even though at his age I never had any doubts).
But we remained friends until his family pulled up anchor and set off for their next port on their tour. I was envious of that carefree lifestyle and all the experiences that it would give him at such a young age (realizing I was just one of those experiences).
Any thoughts I had about the kids from the sailing club in my small town quickly disappeared when I went to sailing week at Chester. Chester is an equally small town but it is on the coast of Nova Scotia and very affluent and very picturesque. The homes there cost a small fortune as Canadians and Americans have made it a favoured destination for the summer. Being waterfront, it has a great marina and the islands that shelter it and ocean beyond make it ideal for sailing races.
The owner of the yacht I crewed on had decided we should go up for the week and we sailed the boat up the coast line arriving in Chester the night before the first race, which was on a Monday. There were tons of races for each class of boat. We had a 26 foot boat so we were in the evening races and then the big weekend two-day regatta, but there were junior races during the week in the mornings and afternoons.
In the morning of the second day I saw Taylor for the first time as he piloted his Lazer into the dock (a Lazer is a one man boat that mostly teens use at sailing clubs, though it is raced in the Olympics). He was in speedos, something I had never seen before on a boy at a sailing club (obviously I had seen speedos, many in my school wore them for swimming including me, but more people wear sailing gear that is waterproof for racing, though given the hot weather his choice maybe made sense). As he pulled up to the dock he took off his life vest so as he docked he was only in his blue speedos.
He was younger than me, but not by much. Maybe he was 14 or fifteen. Sitting in the boat in his speedos with his legs up on the transom he was the picture of both innocence and sexuality. He probably was 5'8", though it was hard to tell with him sitting, he had light brown hair but none on his body except for a few hairs under his arms. He was slim but not skinning. I wouldn't say he had any baby fat, he was clearly naturally thin, but he wasn't boney - his body was sleek with curves and what looked like soft soft skin, which was nicely tanned. His body cried out to be touched. He didn't even have a treasure trail running from his navel to into his speedos so I began to think he might be only 14. His speedos showed the outline of a nice cock and balls under the thin nylon, which had to be about 2" cut when soft.
I was hooked.
He must have won or done well because his friends and family flocked to him. I watched from the margins and immediately began to think about how I might meet him.
The next evening the opportunity presented itself. The Commodore of the Chester Yacht Club had his welcoming ball on the Wednesday of race week (he didn't have it on the Monday in case people arrived late, as the big regatta was on the weekend) and everyone would be there. I figured Taylor, who I now had concluded was 14, could be seduced with alcohol. I was only 16 and not old enough to buy alcohol but sailing people (and Maritime Canadians especially) love their booze so our boat was packed with liquor (I wondered whether all the booze on board was why we hadn't won a race yet that week but, then again, all the other boats were equally laden down with beer and spirits).
Stealing a half finished bottle of Vodka from the boat, I took the additional step of going to the general store and buying a bottle of orange juice. I poured half out and the vodka in.
Once at the club house I watched Taylor from across the room. He was popular so every one was around him. He was in blue trousers and a white shirt with his Halifax yacht club logo on the breast, looking every bit the young nautical sailor. Hard to believe but he looked just as sexy dressed in club house attire as he did in only a speedo. This boy naturally had the look that Ralph Lauren and Tommy Hillfinger were trying to create with their clothing lines and were selling to Americans in their magazines and ads.
I had to wait until Taylor was alone, which came when he went to pee. The club's bathroom, which was small, was full and had a wait line (heavy drinking like yacht people do will cause that) so he headed outside and I followed.
Waiting in the shadows I listened for when he was done and then I positioned myself so I was sitting on the handrail of the walkway he would return on to intercept him on the way back to the club house.
"Hey," I said, trying to sound nonchalant, as though he had stumbled across me, and I was not planning to see anyone and having been discovered was just trying to sound friendly.
"What's up," he responded.
"Snuck out to drink some booze," I said in a whisper, trying to sound conspiratorial so that he would feel he wanted to be in on my little unauthorized escapade.
"Cool," he said, nodding approvingly.
"Want some," I asked.
"Definitely," he said.
He then he took over and started walking down to the dock. I figured he would head some place hidden, since technically what we were doing was illegal, but he went towards the water and sat down on the end of a pier. I sat next to him and handed him the bottle and it was passed back and forth, each of us taking swigs until it was finished.
We made small talk. He introduced himself as Taylor (which I didn't admit I already knew because the second I saw him pulling up in his speedos I had asked because I had to know who this gorgeous boy was). I told him I was Bruce (and that seemed to be news to him, which was kinda disappointing, but not entirely surprising since it was not like out paths had ever crossed).
I discovered he was in Chester from Halifax where he went to a private school. I told him I had gone to private school but I was now in NS while my parents finalized their divorce (what I referred to as my unfortunate incarceration in the nearby town).
Once the booze was gone he went to get up and I decided I had to be bold.
"Can I suck you off?" I said brazenly.
He laughed and said "wish you had offered that before you gave me booze. How about in the morning?"
"Oh, sure," I responded in a bizarrely non-committal and casual way.
I wasn't sure if he was very polite and this was a way to get out of an awkward situation or he was serious about me meeting him in the morning. Either way, I wasn't going to push it because this could go seriously wrong and I had already been way too bold in outright offering to suck his cock.
After standing and looking at me for a few minutes, swaying a bit from the effects of alcohol, he then said with determination: "I race every day at 11, behind the boathouse is a tool shed, meet you there at 9". With that he was off.
The next morning, with a mild hangover, I was up early (around 6) and put on a pair of jeans over my white briefs and a polo shirt and dockers and, climbing out of the boat so as not to disturb my fellow crew (we were all sleeping on the boat, which was cramped, but since everyone else, who were all adults, went to bed every night drunk after partying on each other's boats they were pretty sound sleepers). I made my way along the dock. In the club house there was already breakfast available and I downed tons of juice.
By 9am I was not only in the tool shed but had cleared my head (some was the juice but most want anticipation of sucking off Taylor if actually showed).
Taylor came into the tool shed wearing only his blue speedos.
"You are dressed for the race already," I said, trying to make light of the fact that he was in speedos in case he had never done this before and found being scantily clothed disconcerting.
"Nah, I find that guys like me in speedos," he said. "I put them on for you, don't you like?"
Taken aback, I said with surprise "definitely, have you have done this before?"
"Sure," he said, "last year at Chester I was sucked off by five different guys. I look forward to it every summer because back in school girls don't even talk to me" (his private school was co-ed).
I only half believed him. He was hot so I couldn't imagine any girl not wanting to do him. He was a star when it came to sailing, because he was good, so that would get him lots of attention (certainly got mine) and sailing in speedos is definitely an attention grabber (it is what made me so brazen as to offer to suck him, something I had never done before). So it made sense that in Chester, where he was winning races and looking hot on his boat in his speedos, guys would be flocking to him like I did. But while he may not be as much the centre of attention back at school, he was gorgeous and I couldn't understand why any girl in his high school wouldn't want him no matter what he was doing or wearing, but I was not going to deep think it, I was about to have him and that was all that mattered.
"So did I make the right choice on wearing speedos," he asked, with a twinkle in his eye. This boy knew he was hot and he knew he had me hooked.
In silent answer I went over to him, dropped to my knees and began to lick and sniff him through the nylon. These were a pair he had worn before, not just based on the pattern which I recognized, but once I got around his balls the sweat he had generated while sailing in the hot sun was so musky. I couldn't help myself but I paused to breath in his odors and bask in his sexuality while his soft balls and the smooth nylon rubbed against my face.
"Don't want to rush you boy but I have a race to get to", he said with a little laugh.
He was two years younger than me and he was calling me boy. Then again, it was clear who was in charge.
I didn't pull down his speedos but only took his cock and balls out of them. His cock was about 6" cut, big for his age (about the same size as mine even though I was two years older, though it looked bigger on him cause he was smaller than me) and I devoured it. It fit in my mouth so I didn't need to deep throat. I just sucked him and he stood there and let me.
After a while of my head moving up and down on his hard cock, my hands running over his body (one only running over his speedo encased ass and hips and playing with his balls and the other working on his chest and stomach, he said "I am going to cum." I guess he was giving me a warning in case I wanted to take his cock out of my mouth, but I just kept going because there was never a question in my head about swallowing his cum.
He didn't overly tense, but I could tell the second he was about to cum, and I worked harder at sucking and made sure every drop would end up in my mouth. His cock was forceful in shooting its cum, with five solid volleys that hit the top of my mouth and back of my throat. This boy was virile and, given how hot he was, I was not surprised by the size of the load which I had to swallow as he shot to make room for more.
When he had finished cumming, he tapped me on the shoulder and said "have races to win".
Not only did I release his cock from my mouth, I put it back in his speedos myself, grateful he had let me suck him and feeling I should in return be a full service cock sucker.
I thought about jacking off, as I wouldn't be able to later (sleeping on a boat with my crewmates), but something about the moment was too perfect and I adjusted my hard-on in my jeans so it was less noticeable and went down to the dock to watch him get ready for the race.
To my surprise, when I got to the dock, he was not in speedos, but was wearing jeans and a t-shirt (guess he put the jeans on over his speedos) and he had a one piece sailing suit on that was rolled down to his waist. I watched him put his Lazer in the water, put the mast up and feed and raise sail. Once he had it tightened as he liked it, based, I guess (he was clearly a better sailor than me), on the wind conditions, he rolled up his one-piece and got on the boat.
Watching him was pure pleasure. His young muscles you could see moving under his t-shirt as he readied the boat. And when he had the one-piece on it made his body look like it was in one of the those one-piece swimsuits Olympic athletes today use, it was tight and accentuated that, even at 14, his shoulders were broader than what was clearly a slim waist and hips.
There was no contest during the race. He took an early lead out of the start and was rounding the first buoy a good two boat lengths ahead of the next closest boat. By the finish he was a solid leg away from his nearest rival.
When he docked, after that day's first race that morning, he came over to me in the club house and leaned in to whisper in my ear, "you are a good luck charm, want to do that before every race?" I nodded. He looked at his watch and it was 12:30. "Guess we will be skipping lunch," he said. The next race was 2:30 so I made my way to the tool shed and was waiting when he arrived a few minutes later, after he secured his boat.
He was still wearing his racing clothes. I stood patiently while he removed his sneakers and socks and then watched keenly as he peeled off his one-piece and removed his jeans (sure enough, he was wearing his speedos underneath).
I dropped to my knees and started to sniff and lick him through the speedos as he took off his shirt. The boy clearly liked to be in his speedos and nothing else when being blown. And I liked it too.
His speedos were even more pungent than before, having been on under his jeans and a splash suit that encased his entire body. It smelt sexy, a combination of his body odor and the sex he had sweated into the crotch when I had blown him that morning with them still on him.
This time without encouragement I had his cock (but not his balls) out of his speedos and into my mouth and was blowing him shortly after he was totally stripped down to his bathing suit. While I sucked him I played with him through his speedos. One hand worked on his balls through the nylon and the other roamed over his ass and hips and between his legs tracing and then caressing him through the damp cloth. I was developing a fetish - or should I say a greater fetish cause I already had a fetish - for boys, especially him, in speedos.
Having already sucking him off that morning, it took longer this time for him to cum. It was probably 20 minutes before he leaned down and whispered in my ear that he was about to cum. During that time, I had briefly let go of his speedos with my hand, careful not to interrupt the up and down motion of my head on his cock, and had undone my own pants and taken out my cock,. With one hand I stroked my cock and the other went back to caressing him through that soft damp nylon of his speedos.
While it might have taken longer to cum, the load he unleashed into my mouth was no less forceful or voluminous. The five or six volleys went way into the back of my throat and filled my mouth, with me swallowing frantically to make room for the next.
As soon as the first hit the back of my throat, I began to cum myself with an intensity I hadn't felt before. I guess part of my orgasm was having to do with not having cum in a few days (since we set sail for Chester) in spite of having been hard as usual at night and in the morning, but especially hard that morning while I sucked him off the first time.
When he finished cumming in my mouth, I again put his cock back in his speedos. After cleaning up the mess I had made on my pants and on the tool shed floor as best I could, I helped him dress, getting him back into his jeans and t-shirt and one-piece splash suit. I was like a one-man full service pit crew for my star racer.
For the next two days I met him in the tool shed two hours before each race (9am and 12:30). It meant me getting up before any of my crewmates so no one would ask where I was going and it meant missing lunch but, hey, I was getting my protein another way.
Interestingly, he wore only speedos when he arrived in the tool shed in the morning, but he was dressed in clothes and his one-piece waterproofing when he went out to sail. I took it that he had roped me in with the speedos and now, that he had me, he didn't feel the need to attract anyone else.
In a way I was flattered but as I watched him arrive at the tool shed in his speedos each morning and as I helped him get dressed back into his sailing gear after I sucked him off at lunch, part of me wanted to also see him sail in only his speedos. Yes he looked hot in everything he wore and that one-piece did make him look so lean and fit and professional, but there was something about him in only a pair speedos that was so damn sexy, and I guess he knew that cause he wore them intentionally when he met me in the shed in the morning and quickly stripped to them when he met me at lunch.
Certainly that first time, seeing him pull up in that Lazer in only his speedos, was forever etched in my mind. I wondered if, even if I knew other guys were checking him out (and may even offering to give him blowjobs) it might have been worth it to see him sail one more time in only his speedos, but I also couldn't imagine sharing him. He was mine.
We only spent the time in the shed together. I was crewing on my yacht in the evening races and then hanging out with my crew mates and the owners as they partied on their or others' boats. And he raced twice a day during daylight hours and hung out with the other junior racers in the evenings and at meals. But I couldn't stop watching him even when we weren't together and I knew where he was at any time, even if he was across the marina on someone else's boat.
On that Thursday and Friday morning and afternoon, I spent a good 30-45 minutes on my knees sucking him off in the tool shed, his speedos pulled down under either under his nuts or just covering his nuts (depending on how I wanted to caress his balls) and his hard cock in my mouth as I bobbed up and down on him and brought him off. My hands would roam over his smooth body, and as I had expected his skin was so smooth to the touch and I couldn't get enough of it, but most of my attention was on his speedos which were getting even more pungent each day. It got so I could smell him in my nostrils even when I wasn't nose buried in his crotch.
Each time he would warn me when he was going to cum, which I guess was just him being courteous because not once did I give any indication that I was not going to swallow every drop he shot in my mouth.
Sure enough Taylor won every race, and I like to think I helped.
Once his races were over and he had won the junior championship he found me out and thanked me profusely. I don't know if he believed I had contributed, but even if he was just thanking me for giving him head I was pleased.
"How can I make it up to you," he asked, which may have been a rhetorical question.
I had an idea, but with the regatta that weekend I didn't see how it could be done, without some creative planning.
"Want to go someplace private after the regatta and before the dinner on Sunday night," I asked.
"Sure," Taylor said. "We can take my boat out to one of the islands; we just have to be back for the dinner because I have the trophy you helped me win to pick-up" (he said grinning ear to ear).
Our yacht came third in the regatta. The skipper thanked me for an exceptional performance, which probably happened because, unlike during the week when my mind was elsewhere, I had somewhere to be and wanted the race to be over as quick as possible. As soon as we docked and put all the sails and rigging away, I quickly changed into my speedos (announcing I was going to go swimming before dinner) and headed for the junior clubhouse where Taylor's Lazer was tied up. As I walked up I saw he was in his speedos too and, just as I broke into a big smile, he couldn't help but smile back when he saw what I was wearing.
After donning life jackets Taylor sailed me out to one of the islands that had a small beach that couldn't be seen from shore. We pulled the boat up on the sand and stretched out, with the sun slowly dropping in the sky.
"So what did you have in mind," Taylor asked.
"Do you want to 69," I asked nervously.
At no point had he ever offered to do anything to me, though he had seen my jack off as I sucked him during the last two days. To my surprise he didn't hesitate and said sure.
He had brought a backpack along and out of it he pulled a large towel and some orange juice already laced with vodka. Clearly he had thought this through as much if not more than I had (and clearly offering him liquor that first night was not such a bribe as he could get liquor himself in a town that was just flowing with booze during race week).
Drinking the vodka, while we watched the sun finally set on the horizon, we both got a nice buzz, lying so close on the towel that our sides were touching. Once it was finished we arranged ourselves on the towel so our heads were at each other's crotches and began to lick each other through our speedos. We were already hard, so it was about tracing the outline of our similar size hard cocks with our mouths.
I had his cock out of his speedos and into my mouth before he did likewise, but he showed no hesitation about taking my hard cock into his mouth.
We slowly moved our heads up and down on each other's cock. I had one hand under my head so it was raised up level with his crotch, but that still allowed that hand to roam over his legs and thighs and his speedo clad hips. My other hand was roaming more earnestly over his speedos and his chest and his stomach and occasionally taking hold of his shaft that was most encased by my mouth. This boy was gorgeous and his soft skin felt so electric under my touch I couldn't get enough of him.
One of his hands was also exploring me as he was sucking my cock in return, but was time went on it became a little more targeted. After exploring my legs and my chest and stomach, showing particular interest in the hair I had in each of these locations, he began to knead my ass cheeks through my speedos. Then he had his hand inside my speedos at the back, feeling my bare ass cheeks before sliding his fingers up and down my crack. Before long he had found my hole and his fingers were exploring it while we 69ed.
The boy clearly had a plan, and it wasn't about paying me back with a reciprocal blowjob, though to his credit he was giving me great head as his fingers searched out and began to penetrate my asshole.
I took my mouth off his cock and said what was now obvious to both of us, "you want to fuck me don't you?"
Taylor took his mouth off my cock, though his fingers kept at my asshole and he said "I've never done it before and, to be honest, you are the closest person to my age who had ever sucked me at race week. It's usually older guys. So if I am going to try it with anyone I want it to be you."
I guess he thought that explanation was a compliment, though I wasn't sure how I felt about older guys sucking him now that I thought of him as exclusively mine. And it is not like he needed a reason, I would have let him fuck me - hell, if we hadn't been at a yacht club all week surrounded by people, me sleeping on a boat with other crew, running the risk of being caught every time we hooked up in the tool shed, I would have begged him to fuck me before now - so the only question was what are you waiting for and how do you want to do me.
"Did you think of lube," I asked, given that he had clearly planned this out.
Taylor fetched a small tube of lube from his bag. It was actual lube, KY jelly, which he had to have bought at the general store (I would have been too embarrassed to do that in a city and here he had done it in a small town at only 14).
"How do you want me," I asked.
"On your back," he answered without hesitating.
This boy had definitely thought this all out.
I lay on my pack on the towel and removed my speedos. Taylor left his speedos on, with them still tucked under his balls as I had put them when I started to give him head, and he rubbed lube on his cock and then into my ass crack and into my hole. I placed my legs on his shoulders and, moving forward on his knees, he moved his cock against my hole.
Then Taylor further surprised me and he leaned forward and kissed me. My mouth instinctively opened and his tongue worked its way around my mouth and as we began to kiss passionately his cock slid into my ass. His entire body weight pressed into mey, my feet pressed up against my ears as our faces met with a deep long intense kiss.
It was so incredibly hot.
I had never kissed anyone before and his kissing was intense. So intense was he a kisser that I didn't feel any discomfort as his cock went all the way into my ass to the pont where his balls were pressed against the bone of my sternum.
The more he kissed me the more I got turned on, and before long I was moaning. My hands were all over his back and shoulders, sliding down to his ass cheeks which I felt through the soft nylon of his speedos.
Pulling on his speedo clad hips, I urged Taylor to shove deeper into me.
I was in heaven. Having this boy's tongue in my mouth and his cock in my mouth meant I was being penetrated at both ends. But his kissing was such a turn-on that I found myself panting in his mouth as I became more and more horny.
Without looking I knew that my cock was leaking copious amounts of precum on my stomach.
With my legs on his shoulders, and him leaning down to kiss me, I was in a jackknife position and his hips moved up and down like a pile driver, shoving that hard cock into my ass repeatedly.
His pounding of my ass got quicker, but as he got close, he backed off, pushing my legs off his shoulders. I wrapped my legs around his hips and waist and he lowered his chest onto mine, all the while kissing me, and as his body slid up and down along mine my precum was making both our stomachs wet.
I dug my heels into his speedo clad ass, urging him on, deeper into me, willing him to cum inside me.
True to habit, Taylor briefly stopped kissing me to whisper in my ear "I am going to cum" before resuming our kissing, his steady fucking of my ass with his hard cock not missing a beat.
My hands grabbed his ass cheeks and pulled them into me hard as his hands did the same to my shoulders, forcing his cock as deep as it would go so he could deposit his seed as far into my ass as he could.
He thrust hard, holding my shoulders, again and again as his cock pulsed in my ass, spewing forth its thick semen. I know him like a book and I could imagine each spurt that had filled my mouth the last couple days doing the same deep in the recesses of my ass.
His breathing became less frantic, and his kisses became less rushed as his body noticeably relaxed, the last of his orgasm beginning to subside.
My legs which were wrapped around his waist relaxed as he collapsed on top of me. His head rested on my shoulder and his panting slowly turned into contented leisurely sighs.
While my legs wrapped loosely around his hips kept his cock in my ass for a while longer, eventually his cock softened enough it slid out of my ass. I was sad to feel it slide out, but he made no attempt to move and I lay there with him on top of me on the sand, glowing in the aftermath of the first true lovemaking I had ever experienced.
For a gorgeous 14 year old boy who clearly looked forward to his summer race week where he would wiggle his hot speedo clad ass and get blowjobs from strangers, when he put his mind to having a romantic getaway he knew what to do to please the other guy and, from the way he was breathing, himself.
Eventually he looked up and said "we have to get back". He then, as he lifted his body off of mine, reached down and ran his hand over my stomach and held it up to show me, it was glistening with cum where I had unloaded between us. He grinned as if to say "see what I made you do." It was endearing and I found myself leaning up and taking his head in my hand and kissing him lovingly in gratitude for, yes, he had made me do that and I loved it and loved having him fuck me.
We rinsed off in the ocean, which now was quite cold, and sailed back to the yacht club, just in time for the awards presentations (having missed dinner). I beamed with pride when he went to get his trophy, wearing only his speedos (as we didn't have time to change). While I knew that I had done nothing to contribute and it wasn't like he was my boyfriend, he was just a summer fling, but one that I will cherish always. And I knew there were probably men in the audience who were looking at him in his speedos and lusting after him and he, at least during that Chester race week, was all mine.
When I got home from sailing, having gone the rest of the trip without jacking off due to a lack of privacy, I spent the next few days in and out of the washroom jacking off thinking about sucking him and him fucking me and, most of all, thinking of him in his speedos. I imagined what we looked like on the beach, me buck naked with my legs on his shoulders and his speed clad ass moving up and down as he pile drove that hard cock into my ass, or how we looked a while later, him lying on top of me and me holding him, his cock still in my ass having deposited its huge load.
I wondered if I would ever see him again. I knew that come hell or high water I would find a way to get back to Chester race week the following year.
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