Once I came back from Chester race week, having won the week in a 24 foot boat (the smallest yacht you can enter race week with) I was a star.
While one week made me a star (well, one week and the heaps of attention that the first and second students had given me cause of my popularity which led to my being elected Chief Petty Officer) I was not a serious star when it came to sailing.
Gordie was the club's real star. He was only 12, but he had qualified for the Olympics in the Lazer and, for our two-person sailing training he had chosen me to be his crew after my win in Chester.
Gordie was small, about 5'5", blond and wiry. At 17 I was 5'9 ?" and had some heft, so when we were racing along at top speeds I could hike out or even use a trapeze to compensate for Gordie's lack of weight, giving our boat the advantage to take high speeds close to the wind.
All the strategy was Gordie's. He was the skipper and he planned the race before hand and, in the moment, decided when to tack and when to deviate from the plan. If I was being honest, I was pretty much ballast, but he called us an unbeatable team and we did win every race that summer.
Gordie's older brother, Chris, was one of the sailing instructors. Like Gordie he was blond, but he was 19 and handsome. He had a girlfriend who was his equal, a gorgeous blond with flowing hair who would meet up with him and the other instructors after lessons and they all would head off for a night on the town. Drinking age in Nova Scotia was 19, so while I was only two years younger than Chris and had been drunk, I couldn't socialize with these adults and, besides, my friends were his younger brother and the junior sailors so I simply thought of him and the other instructors as outside of my league.
One Friday afternoon after a week of very successful racing, Gordie suggested I stop at his place on the way home. By this point I was biking to and from the yacht club and Gordie's house was on the way out to the point so it was on my way.
At Gordie's house he showed me around and we ended up in his room. His brother Chris came in to his room to see what we were up to and I immediately got embarrassed. Now Chris was an instructor and knew we sailed together as a (rather successful) team and that we were friends, but suddenly being in the room of his younger 12 year old brother made me feel guilty. It was like Chris knew I had sexual thoughts about his brother (which I didn't even know that I did have) and when he spoke to me he wasn't making small talk but his very look accused me of wanting to have sex with his kid brother.
I prayed for Chris to leave. He had a girlfriend and it was Friday and didn't he and all the other sailing instructors have an exciting evening planned in front of them. After all, every Monday morning they all had stories from their weekend of partying that reminded me I was underage and they were adults.
To make matters worse, Gordie announced he was going to change out of his dirty clothes from sailing and began to strip down to his underwear.
I stared at the floor and out the window and any place but towards Gordie. Maybe my uneasiness is what intrigued Chris because once Gordie was in his briefs, Chris asked me what I thought of Gordie's stylish briefs. I glanced over and they were psychedelic. They were white but with lines of many different colours running in different directions and around in circles. Chris said again "what do you think."
I stammered "they are cool," trying not to look at them too long, though my refusal to look at them directly probably (with hindsight) confirmed what he suspected, I had become gay for his brother - if not just outright gay.
"They used to be mine," Chris added, though I couldn't imagine how that could be as there was a seven year age difference between the two. When I looked at Gordie he nodded to confirm and, obviously liking the attention, was making no move to put on clothes.
In my mind I was begging Chis to leave and begging Gordie to put some pants on, but neither was making a move to do either. Gordie seemed content to hang out just in his colourful briefs and Chris seemed to be enjoying my discomfort.
"They are really soft," Chris ventured, "why don't you feel."
I looked at him shocked. Was he really suggesting I touch Gordie's underwear while he had them on? I had already concluded that he suspected I was sexually attracted to his younger brother (even though in my mind I was convinced that this wasn't the case), but this went beyond teasing me. Was he testing me? What should I do, should I bolt?
I was too scared to do anything so I continued to just stand there, looking at my shoes in embarrassment.
"Gordie," his brother continued, "let Bruce feel the fabric," to which Gordie came over so he was standing only inches from me and he pulled his briefs out towards me, presumably so I could feel the fabric but in doing so he pulled the front out and I could see down in the front to his cock and balls, which were bigger than I thought they would be, already with a few hairs emerging where the pubes would grow in.
I couldn't help but look.
"See," said Chris, "I told you he liked you."
"Yea," said Gordie, not so much laughing at me as giggling pleased with what had just been confirmed.
"I'll leave you at it," said Chris, who left the room.
"What the fuck was that about," I asked Gordie, who was still standing there in his briefs holding the front out for me to either feel the soft cotton or look in the front where I could see his cock had now fully hardened.
"My brother knew I liked you but I didn't think you liked me back, but he was sure and it seems he was right," said Gordie, who took one of my hands and placed it into his briefs, where it instinctively closed around his hard cock.
"And your brother is fine with this," I asked incredulously.
"Of course, he is my brother, he wants me to be happy," Gordie responded.
I didn't know what to say. But while my mind struggled to come up with an answer my hand explored his hard cock and balls.
"Have you done this before," I asked, continuing to play with him with one hand and the other, as if drawn to a magnet, moving to his bare chest where it began to explore his smooth body.
"No, you are my first love," he said.
LOVE???
He was 12 and I was 17. We were friends and good teammates sailing but we barely knew each other and had nothing in common outside of sailing. How could he have any feelings?
Of course as my hand explored his body and my other hand played with his cock and balls I couldn't deny I felt something powerful towards him. But it had to be lust. It couldn't be love.
And what did his brother think? He seemed to be giving us his blessing, in fact he seemed to have set this all up, but he must think that a 17 year old and his brother were wrong on so many different levels. He was the epitome of straight, with a gorgeous girlfriend his own age who matched his attractiveness and a social life that involved people his age going to clubs and dating people of the opposite sex. How could he be fine with this?
As all these thoughts were running through my head my hands kept playing with Gordie's body.
Standing next to me wearing only his briefs with my hand in the front of them, Gordie began to undo my belt and push down my shorts and my blue briefs, so before I knew it I had my pants around my ankles and his small hands were exploring my cock and balls.
I resigned myself that this was happening - no, to be honest I hoped it was happening - though part of me worried it might be a trap and this would go terribly wrong at any moment.
Slowly Gordie got the rest of my clothes off me and I took off his briefs and we made the way to his bed. We were such a contrast, Gordie this tiny blond boy who barely looked like he had reached puberty, though his cock confirmed he had, and me who was well past puberty with a patch of hair on my chest, hair under my arms and on my legs and a full growth of public hairs beneath my navel. I was even starting to get hairs running from the patch on my chest down to my navel, though these were pretty sparse. My cock and balls had to be double Gordie's.
"Do you want me to suck you," asked Gordie.
Cognizant that this boy was eager to please but was doing so out of some probably misplaced emotion that he thought was love, I said no, but told him I would suck him.
I suppose if my brain realized he was trying to figure out his feelings and sex would only murky the waters I should have said we should do nothing, but having played with his cock and balls and smooth body for a while now I really wanted to suck him off.
So, while we moved into a 69 position, it was only me who took his cock into my mouth and as I sucked on him he played and examined my cock and balls. Before long he was no longer moving his hands on my genitals as he gave himself over to the pleasure I was giving him.
As he moaned in pleasure I worked his cock and coaxed his load of cum out of his balls, up the shaft and into my eager mouth. I kept sucking him until he went soft in my mouth and then lifted my head off his crotch, and when I looked down at him I saw he was watching me with a big smile on his face.
He scurried up and put his head on my shoulder, wriggling in under my arm, which naturally closed around his shoulder, and we lay like that, with his naked body next to mine, his leg over my thigh and his head on my chest.
After a while I said "I have to go, and you must have supper", and he scooted up a bit on the bed and kissed me on the lips. I was going to open my mouth to French kiss him, but it dawned on me he probably had never kissed, so I waited to see where he took this. Sure enough, he just kept giving me little pecks on the lips and smiling and looking in me eyes and kissing me again.
Lifting him off me I got out of bed and began dressing.
"Can we do this again sometime," he said eagerly.
"I guess so," I responded, not sure on how I felt or on what we had just done or should do, given our age differenced and the emotions he was so clearly feeling. Then again, I was only in Nova Scotia for the summer so what was the worst that could happen? And didn't his brother approve.
I biked home conflicted between the feelings I had for him, yes lust for his horny young body but also I was feeling something emotional. Having him under my arms felt so right. The fact that on the ocean he was in charge of us as the skipper and award winning sailor and tactician and in bed he had been a young boy protected under my arm was clearly touching me on a number of different levels.
For the rest of the summer, every Friday (which was the only week day his family didn't have a sit-down dinner and so no one was usually home), I would bike to Gordie's and we would get naked. Over time I came to explore his body and know every inch of it. It would always lead to me sucking him off and then us lying together with him under my arm. But on the way to that climax I got to know his body intimately, exploring him with my tongue from head to toe, from between his butt cheeks to under his balls to under each armpit. I taught him to French kiss, so our kissing went from his excited little pecks of pleasure on my lips after I had sucked him off (which he still insisted on doing) to intense making out before I went down on him.
He never did more than explore my cock and balls with his fingers and hands, nor did I encourage him to. First I thought my cock would be way too big for his 12 year old mouth but, second, I figured he should do what he felt like on his own time and I had no right to rush him.
At the end of the sailing season we had our last Friday together and we spent it not having sex but just lying in each other's arms in his bed. When we parted it was tearful on both our parts.
That Sunday the club had its season closing party and I went with my mother. Gordie's brother Chris was there and was quite drunk by the end of the evening. He went to corner me to talk to me and I, not wanting to make a scene, went outside to the yard where all the sailing boats were now pulled up and battened down for winter.
I led Chris to a secluded corner and sat down on some crates.
"What can I do for you," I asked.
"So I was right about you being gay," he said directly.
"I guess," I responded.
"Did you love my brother," he asked.
"I think so," I said. "I didn't hurt him and I think I made him happy."
"But you are gay," he said again.
"What are you getting at," I asked.
"I gave you my brother," he said, "you owe me."
"I don't know what you mean," I said, though I was starting to guess he was drunk and horny and figured I was gay so would be willing to get him off.
"What Gordie and I had was special and I don't want to cheapen it," I said with a note of challenge in my voice, "you wouldn't want me to betray your own brother, would you?"
"No," he said. Though after a moment of thought he added, "but you probably had sex with guys before Gordie and you will after him so what about me."
"I thought you had a girlfriend," I said.
"We broke-up," he said, looking sad and that made my heart go out to him (probably because when he looked sad in that light he looked just like his younger brother had when we parted company on Friday night).
Then his face lite up and he reached in his pocket and pulled out a small packet of lube and waved it in the air.
"I heard about you and Taylor and Reese," he said proudly.
"What did you hear," I asked as my stomach rose to my throat.
"Didn't you guess we all went to school together?" As soon as he said it I clued in. These were the rich kids of Halifax. Of course they went to school together. So when I had sex with Taylor it was one of Reese's classmates, just as for Taylor Reese was one of his. What I had taken as a summer of fun where none of these people really mattered to me, it suddenly dawned on me that they all mattered to each other.
But what about Chris and Gordie? Chris was older and Gordie was younger. I had enjoyed my time with Gordie, but I had only sucked him and I would never see him again. And this was Chris, his older brother who was grades above Taylor and Reese so who would fooling around with him hurt. I had already ruined things with Taylor and Reese, but I would never want to hurt Gordie and I couldn't imagine he would want to either, after all, he had basically set things up between the two of us.
"Gordie can never know," I said.
"Of course not," he answered, as he got to his feet and began to undo his belt and pants and to push them down around his ankles (sure enough, he was wearing white briefs with coloured lines just like Gordie wore, though in a much bigger size and with a much bigger package contained inside them).
I stood up and pushed my pants and underwear down around my ankles and took the lube from him and began to put it on my hole.
He pushed down his briefs and released what had to be an 8 ?" inch cock. If that was any indication Gordie would fill out nicely over the next few years.
Whatever the bigger picture was, I wanted his cock inside me. If we were going to do this, I wanted to feel every inch of it and to get his load deep inside me the way his brother had been doing into my mouth for the last month or so.
I leaned against a nearby boat and Chris position himself behind me and pressed his cock into my hole. Pushing up, as he was taller than me, he entered me and it didn't take long and he was all the way inside my ass.
Taking hold of my hips, Chris began to immediately start fucking my ass and that big cock felt so large in my ass - such a stark contrast to his brother's boy cock I had sucked on that summer - that I couldn't help but block everything from my mind but the raw visceral sex we were having, outside in the cold, with the wind from the ocean pelting us, our pants around our ankles.
Maybe it was because Chris was drunk or maybe he just had great stamina but he rode my ass for what seemed an hour. Our lower bodies were pretty wet from the spray that came up from the ocean, especially his ass and legs, though the outside of my ass cheeks and legs as well. As his cock rammed repeatedly against my hole, it kept my hole, crack and the inside of my ass dry and warm from the friction.
Soon the telltale signs were there, as his balls tightened against his body and stopped slapping against the back of mine, as his breathing got shallower and as his thrusting became harder and more frantic. Bracing myself harder against the boat I let him plow as hard as he could, forcing his cum out up the shaft of that large cock and deep into the ass of the boy who had been sucking his younger brother off for most of the summer.
I stayed like that, leaning against the boat, as he finished cumming and then pulled his big cock out of my ass and pulled up his pants and underwear. In fact, I stayed like that as he walked away, having just fucked his brother's supposed boyfriend, Chris clearly didn't have anything to say and skulked off into the night while I stood there in the boat yard, pants around my ankles, the ocean spray hitting my naked ass.
I stayed like that for a while. I don't know if it was penance for letting Gordie's brother fuck me or because it made me look like I felt, a whore, or because I actually was enjoying being in that position, leaning against a boat with my ass exposed being (and now having just been) fucked.
On the flight back I reflected on the summer and what I had with Gordie was special and, assuming he never learned about Chris and me, I knew it had been special for him too. And the fucking Chris gave me the last night I deserved and, what is more, I enjoyed. It was who I was too.
Even if I find romantic love and nothing makes me happier than kissing and cuddling I am probably also always going to need to get fucked and used for a one-night stand by someone new and hot. While it would never work, keeping it in the family would definitely be one way to go.
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