When I first started crewing with the two dentists, I had proposed we should sail down to Chester for race week. My motivation was I had hoped to see Taylor again. The previous year I had met Taylor shortly into the week and, while he was only 14, he was so hot in his speedos I couldn't resist propositioning him which led to my sucking him off twice a day (right before every one of his races) and him fucking me on a beach the final day.
Even at that young age he had a swimmers body, with thin hips and broad shoulders. And while I had always had a thing for speedos, he had made it a fetish for me - so much so that if I walk through a department store and see a manikin wearing speedos I get hard (and I would get hard wearing my own speedos if I didn't jack off before I put them on).
But I was 16 back then, and he was 14, and as we lived in different provinces we had not stayed in touch. I knew little about him aside from he went to a private school in Halifax, and now, a year later, I had started to fool around regularly with this 15 year old boy Reese in my sailing school so I hadn't really thought about Taylor since the beginning of the summer.
I know this new boy Reese liked me. He had been watching me from early in the summer and he had manoeuvered to be near me and, more recently, he had me sleep over and had sucked me, 69ed with me and even given me his virginity. Given how he was getting more aggressive sexually, I figured I was an experiment, but part of me knew deep down he liked me a lot. For my part, I liked him, loved hanging with his family and found him increasingly sexually attractive the more we experimented.
The boat we crewed on with the dentists was small by yacht standards. It was 24 feet. My previous boat, which I had sailed in Chester race week, was 26 feet and while 2 feet might not seem like a lot in a boat it is major. A 26 foot boat needs a crew of between 4 and 6, and the previous year we had 6 (me being the youngest at 16, the rest being adults). The cockpit fit six nicely so we could alternate between leeward and helm and no one got in each other's way. As for sleeping, the boat had six separate padded surfaces so everyone could sleep comfortably.
When it came to a 24 foot boat, the cockpit could barely fit four, which is why Reese and I were usually on opposite sides in the cockpit as were the two skippers (the two dentists) unless it was windy in which case we would all be on the windward side trying to level the boat.
In the early days that gave me lots of opportunity, once Reese had joined our crew, to check out his crotch, as the mainsail blocked his view of my head (and thus my eyes) and I could try to picture what was filling those shorts/pants.
I never expected Reese to be part of Chester race week. I had lobbied for us going to it early when I first started crewing. And I had dropped the idea when I got no reaction. Little did I know that other people at the club were playing up the idea.
Taking us aside, the Wednesday after Reese (at least in his mind) game me is virginity the Saturday before, the doctors announced that they had decided to go to Chester. As the boat was only 24 feet, they could take it themselves. I immediately offered to go. I hoped like hell Reese would not get permission to join us.
I didn't hear anything else, and Reese didn't invite me over that Saturday, so I was confident we were on our own until I showed-up on Sunday for the overnight sail between Halifax and Chester. There was Reese with his bag, wearing sweatpants and, frankly, looking sexy, ready for the trip.
Unlike a 26 foot boat, space is a premium. There is a space in the bow where two people can fit and then the main body which has instruments, a small galley (little more than a propane stove) and two padded seats (which can be used as beds). With four of us, and two of us being kids, we were told that the bow we would share and the dentists would take the benches (and if it got too hot they could sleep on deck).
The two skippers took turns through the night guiding the boat, and between motor and limited sails, it wasn't much to navigate down the coast and between the islands.
Reese and I were sent to bed in the bow (there was small curtain which Reese closed, claiming he wanted to block out the light), and while we both got into bed fully dressed, before long Reese had slid in behind me and had undone my pants and had his hand in my briefs playing with my cock.
I don't know if I didn't stop him because I liked it or because I didn't want to make noise or because I didn't want make a scene. But I do know I fell asleep happy with him behind me and his hand in my underwear playing with my hard cock under the blankets.
We eventually got to Chester, and in spite of Reese sleeping next to me and fondling my cock, no one seemed to be the wiser.
We arrived and docked, had our board handicapped. In yacht racing where people have different size yachts, there is a mathematical way of determining the optimum speed of a boat so that a 24 foot yacht can race against a 30 foot yacht and the comparative advantage is adjusted for. I have no idea how it works.
When it comes to Lazers (like Taylor raced) it was not necessary to handicap the boat because the small variation was inconsequential so it was racing apples against apples. In yachts it is apples against coconuts.
I walked around the yard, with Reese conspicuously in tow, but I didn't see Taylor. So I relaxed. While I came looking for Taylor, it was best he was not there. Reese clearly was not going to let me out of his sight.
The first two nights we did pretty well racing, given we were the smallest 'yacht' in the adult races. 24 feet was pretty much as small as you can go with a fixed keel boat (which was a prerequisite for the race).
Each night as expected the adults would party and drink. I didn't propose Reese and I drink as he was already clingy enough. We would go to bed when our skippers did and when they were snoring soundly from the booze, Reese would jack me off in my briefs. I didn't stop him. I guess I liked it, but what was I going to do, we were on a boat together sharing a bed within feet of adults who knew our parents and had promised to look after us for the week. I had no choice. Well, I may have had a choice but I chose not to make it.
If fate has a sense of irony, which I am sure she does, on the third day - a Wednesday and thus one year from when I saw him the first time - I was down at the water with Reese in tow and who should pull up in a Lazer but Taylor.
Taylor was even more gorgeous than a year ago. He had grown at least two inches. He had broader shoulders and slimmer hips (if that is possible). And, he pulled up wearing speedos (this time red, which was much more noticeable than last year's blue) and a life vest which he whipped off as he docked so he was only in his speedos as he pulled up.
His body was as lean and smooth as I remembered and his legs even longer, as he threw his bow line to the dock and boys and girls scrambled to tie up his boat.
I thought he saw me but he made no obvious look in my direction as he got out of his boat. Where he used to be close to my height, even though two or three years younger, he was now taller than me. And that cock which I estimated to be 2" cut in his speedos, had to be around 4" now when soft.
Taylor ignored me and worked his way through his friends and fans. Turning to Reese he nodded and then looked at me quizzically.
Having now spotted Taylor, and having seen him to be even more of a hot specimen than before, I couldn't not track his movements. Of course I was being watched by Reese even more intently.
As the week went by, I watched Taylor race morning and afternoon and rack up win after win. Clearly I wasn't his lucky charm like he told me the year before.
I also watched him sail every day in his speedos and while I never saw him go off into the tool shed with anyone (Reese wouldn't leave me along enough to follow him), I did see older guys fawn all over him in the clubhouse and after races.
It drove me crazy.
I hated the idea of older guys touching him. Hell, I hated the idea of anyone touching him. Where a year ago I thought I would like to watch him sailing again in his speedos, seeing him only in his speedos made me want to cover him up so no one could look at him.
And each night, after watching Taylor being the life of the party, I would climb into bed and, after our dentist skippers passed out drunk from partying, Reese would undo my pants and play with my cock and, yes, make me cum quicker each evening as I would think of Taylor in his speedos that day and even imagine him with the old guys I saw him with.
I was getting seriously fucked up. But on the flip side, the more confused I got the more I focussed on our sailing and we quickly became a contender for the title. Our only 24 foot boat, once allowances had been made for the design (i.e. handicap), was within reach of at least a pennant if not the trophy.
It would all come down to the regatta.
The two day regatta started well, as there was no more junior sailing competition so no more seeing Taylor in his speedos. But then, just when I thought it was safe to go back in the water, I saw Taylor on the lead boat crewing.
There were no rules on who could crew. And Taylor was a good sailor. But I couldn't help but see it personally.
On day one we were quick at the start and, even though Taylor's boat was bigger and quicker, once the adjustments had been made for handicap we were tied for first place.
That night, when Reese reached into my pants I came almost immediately when his hand touched my cock.
The next day we were again doing great and it came down to a question of whether or not to use the spinnaker on the downward leg. As I said in a previous story, I love the spinnaker because it is the most colourful.
The wind was gusty which was not ideal.
"Trust me." I begged. "I can make this win it for us."
To my surprise, not for any other reason than because I was thinking of Taylor, Reese said "trust him." And they did.
I stood on the bow and managed the spinnaker and low and behold we, once the differences in our boats were allowed for, had won the trophy.
Once we had tied up the boat and stowed the sails, I slipped away. I headed over to the tool shed, where Taylor and I had met before every race. I guess Taylor has the same idea because he was there.
He smiled at me at said "well done. You beat me."
"Well, it wasn't just you," I said, giving him an out, "maybe it was the other crew who lost."
He laughed.
Then he reached into his pocket and pulled out the same brand, make and size of lube we had used a year ago and held it up and wagged it at me.
I nodded.
He led me out of the tool shed and I followed him to the junior pier and got on his Lazer, putting on a life vest I found on the dock as he did.
We sailed out to the same island and pulling the boat up on the sand, he said "I don't have a towel."
"That's ok," I said.
He and I began to undress and we each laid our clothes out on the sand so we created a blanket.
Once we were both naked I lay down on my back and he, using the lube, slicked up his cock and my ass hole and began to press into me.
Without much effort he was buried deep into my ass. His cock had to be at least an inch if not two longer than the year before and, as he leaned into me each time, my cock twitched.
I had thought he had been romantic the first time, but this time he was so slow and leisurely that I figured he knew I loved him inside me. He took long slow strokes and every time his balls hit my ass I wanted him deeper inside me.
Eventually he quickened the pace and I knew he was going to cum inside me. Knowing we were alone on an island, I began to cry out, "yes, fuck me Taylor", "cum inside me" "Oh god our cock feels amazing".
Taylor cried back equally loud "oh yes, I am cumming," as he shot spasm after spasm of cum into my ass.
He collapsed on top of me and I was once again in heaven like a year before.
Then he said "do you think Reese liked that."
Panic set in. How did he know Reese? Why would Reese know about this? This was our private place, what was Taylor talking about?
As the shock took over, Taylor pulled his cock out of my ass and stood up and got dressed. I looked up in desperation.
"I am sure Reese will get you back to shore," Taylor said.
As I tried to hide my soft cock and my nakedness, Taylor put his boat in the water and sailed back to shore.
I looked around desperately and, sure enough, Reese' head was just above a rock watching, as I lay there naked.
I grabbed for my clothes, put them on and ran over to him. But as I did, Reese ran to the shoreline, got in a dingy, stared the motor and powered himself back to show.
After standing there for a while, I realized I had no choice but to swim. So I dove in and swam back to shore. I shucked my clothes as soon as I was out of the water, and got in our sail boat, putting on dry clothes and getting under the covers.
When Reese came to bed he would not sleep near me. In fact, he would not talk to me for the rest of the summer.
I was very confused. I had loved Taylor, but he seemed mad at me for being with Reese even though I was clearly willing to choose him over Reese.
Reese, clearly liked me. I get that. He wanted me to take his virginity, but when I did it was like I was a prop (a dildo?) and he didn't seem to care who he was fucking. That is why sleeping with Taylor was not like cheating, was it?
OK, I betrayed him, but I knew Taylor before him and letting Taylor fuck me (he had done it before) was that enough to leave me stranded on an island? What if the water had been colder?
The sail home with Reese next to me made me run these and other idea around and around in my head.
Was I a bad person? The only thing I knew for sure was I liked being fucked more than I like fucking. I had wanted Taylor's cock inside me more than I wanted to be inside Reese ever again.
If I knew the terminology I would have realized at that moment I was a bottom.
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