I guess this story is crossgenerational. Troy is 17 and John is late 30's at the bginning, and this is their story. Complete in two parts. I have pictures of both characters if you would like to see them.
Troy
Part 1
My first day on the job and I felt very apprehensive. I had been recruited to take over as Director of Sailing for a National Sailing Academy. My experience was, on paper, excellent, but I had been away from this kind of work for years. I stood back for this first day watching how the senior instructor handled everything with the cadets. The official age range had to be 8 to 18 for insurance purposes. The group I could see today consisted of one girl at the lower end of the limit and about a dozen boys no older than ten. A small gap and then two more boys about 12 to 14. The final one looked as though he was some kind of supervising cadet helping the senior instructor. He was I guessed close to the upper limit. I watched him for a while as he helped the little ones rig their dinghies.
He was medium height, a few inches shorter than my 6 foot , broad shoulders, the body was quite soft to look at, I thought he could do with some gym time to get his muscles showing more, all the sit ups he would do sailing would help the abs look good though. He was also incredibly attractive to me with wonderful soft brown eyes. He had the usual black nap of hair common to the Afro-Caribbean male. Colour I would say was medium coffee. My guess was that the bottom half would be just as stunning, he had good calves but then it got horrible, the modern fashion idea, baggy shorts that only just remained up, but at half mast across his butt, underneath them he had another pair of shorts/boxers that I could see about foure inches of, and below them another pair of what I assumed were his underwear, dark blue of unrevealed style. When I got to speak to him he had a wonderful soft voice that even talking about sailing almost seduced you. I realised that I was staring at him almost all the time that he was on the beach, and did the same when the boats all came in again at the end of the session. I got a chance to talk to him again when I started taking details. The previous director had done virtually no administration so I needed to get the cadets records up to date first. His name was Troy and by the time the youngsters were all finished and away with their parents, or off on their bikes, I was in love, well more in lust at this stage. He was, to me unbelievably gorgeous.
I spent much of the next week quizzing the instructors about the students, particularly Troy. He came from a poor home and was on a sailing scholarship, that is, he didn't have to pay fees. He was the best cadet in the school with a terrific attitude, he never answered back and was very respectful towards the instructors. He was also the best sailor amongst them, I found that out the next week when I had them racing Laser's. He won by quite a large margin.
The next week I got to talk to him a lot more as I quizzed the better cadets on their ambitions as far as the sailing went. He wanted to make his career in the Marine Industry so I took that as the reason to give him more of my time and see what we could achieve. Not altogether altruistic of me. I wanted to be near him, and if there was ever a possibility of seeing him naked, I knew I would jump at it. I was too old to ever think about a sexual relationship with him, but it would be nice to have a complete picture of this beautiful boy to fuel my fantasies.
The next step was to get him into the keel boat programme. For me that was a retrograde step because the keelboats ran from a satellite base so I would see very little of him. I would have to make excuses to go there occasionally when I knew he would be doing land based work.
I did get to see more of him than I could have expected, and he realised I was taking a particular interest in him personally. He became very friendly and quite relaxed in my company. I told him that he had been approved as a cadet supervisor in the dinghy programme and anytime he wanted to earn a little money I could employ him at the main base, but it wasn't to interfere with his keelboat programme. I started to see more of him then, I let him sit in on instructor meetings and briefings, sat with him to talk about all the different opportunities there were for him on the island, and how far I could go in helping him.
We talked easily together and when he found out I was gay, I think it all clicked into place. He blushed profusely as he spoke again.
"Is that why you are helping me so much?"
I laughed to try to break the tension that had sprung up between us.
"No Troy, I'm helping you because you are good, you are eager, and you are respectful to my instructors. Yes I think you are an incredibly handsome young man and if I were 20 years younger I might be trying very hard to get you into my bed, but I'm a realist, so be assured you are getting the benefit of my support because you are worth it."
He nodded but didn't reply. For the next few weeks I wondered if I had damaged our relationship by admitting my sexuality because he was very distant with me. The easy relationship we had was gone, I was once again the Director of Sailing and he a cadet. It made me sad, but I still monitored him carefully, employed him as often as I could to put money in his pocket, and continued with the personal tuition. It wasn't really enough for me but it had to do.
Nothing changed very much over the next few months except that he was accepted as a helmsman in the keelboat programme. That was a real boost for him and gave him huge kudos among his peers and other cadets. The next big step was to get him up to speed on all the international racing rules so that he could race in the regular weekly yacht racing at the local club. I took on that task as my instructors were now all working flat out to keep up with the new intakes from the schools.
His first race and he fully realised how important the rules were to keep the more aggressive sailors in check. New boy on the block, they tried to force a passage on marks without the required overlap, they tried intimidation when he was on the Starboard tack even though that gave him the right of way, and other less obvious rule infringements. I had put myself in the crew disguised as best I could so that other skippers wouldn't realise I was on board. At the end of the race, in which he didn't disgrace himself, he gave me a hug to thank me. I melted, God, this boy did things to my emotions that completely unbalanced me.
"Thank you so much for your help John, I would have been eaten out there without your guidance."
I smiled, so tempted to say that he would be eaten in here if he would let me.
Another morning during which we finessed his knowledge of the rules and then I took him to lunch. I was taking the afternoon off so I was able to take him away from the marina. An enjoyable lunch followed and then I asked him if he wasn't busy would he like to go sailing with me in my yacht, it was quite a bit bigger than the keel boat he sailed, but I had it rigged for single handed. An enthusiastic `yes' and we were off. A pleasant couple of hours sailing before I anchored us in a bay to let us relax and have a drink while I explained the differences that size made, not much to worry him as we proved with him at the wheel.
We were both wearing shorts with no tops, I wasn't ashamed of my body up against one nearly a quarter of a century younger than mine. He had discarded his trousers which he had worn for the morning and was left with just a pair of boxers on. I had on my beach shorts which were quite tight and showed the outline of my cock, as did his boxers. We had both scoped each other out, me noting a soft cock about four or five inches long that looked a good thickness. Him, noting about six inches of cock that was only just maintaining a decent shape. If he did or said anything in the least provocative I knew I would end up with a full blown hard on and he would know that there was about 8-1/2 inches of man meat waiting for him anytime he wanted it.
Sat in the cockpit with our drinks he got a little bold.
"You look really sexy John, for a man your age. Do you have a boyfriend?"
"No, I don't at the moment, would you like the job?"
I was smiling as I said it, but his reply soon wiped the smile off my face.
In something only a couple of decibels louder than a whisper he dropped his eyes before saying, "Yes please."
I was completely dumbstruck, he couldn't mean it, he had to be kidding me, but it was such a serious comment, made with so much reticence. I reached across the cockpit table and lifted his face so that I could see his eyes. When I could speak again I asked him.
"Are you serious Troy?"
He nodded.
"I know you are gay and I would really like you to make love to me," then he dropped his eyes again and blushed a deep colour that his own colour couldn't hide.
"You know I would love to do that more than anything in the world, but are you sure?"
No rejection, in fact quite the reverse, he looked up at me again and almost gushed out, "Oh yes John, I admire you so much and you look after me as often as you can. Please make love to me."
I could no sooner have said no than fly to the moon. I was going to take this boy below, and with the gentle rocking of the boat I was going to make love to him like I hadn't done to another male in years. I took his hand at the bottom of the companionway and led him through to the master cabin. Stood alongside the double bunk I dropped his boxers and stood back. My eyes watered, he was so beautiful to me and the bits I had not seen before were perfect. My erection was so hard it hurt, being pushed down in my shorts, so I quickly shed them. When Troy saw my monster he gulped and then looked at me with a pleading expression.
"We don't have to indulge in anal intercourse Baby. I can, and will make love to you without penetrating you. Shall we go for a shower first?"
He nodded and then whispered to me.
"If you fuck me, you will be gentle with me won't you?"
"I'll be gentle with you always, and you can stop worrying, I'm not going to fuck you today."
Right decision, he visibly relaxed and enjoyed me washing him in the shower, well, pampering him really, taking an awfully long time on his genitals and his gorgeous, tight little bottom. His erect cock was all I could have asked for, uncircumcised, and quite thick, about seven or eight inches long I guessed. I knew that if our relationship developed I would one day feel it reaming out my insides, but today I was going to let my tongue and lips give me, and him all the pleasure.
"Can I wash you now John?"
After I had finished rinsing him I was more than ready for him to pamper me. I disgraced myself by cumming a huge wad of sperm when he touched my cock, I was so turned on by this boy.
"I'm sorry Baby but you are such a total turn on for me."
I think he was more embarrassed than I was so I took him in my arms and gave him a soft kiss on the lips.
"Don't worry about it, I will now be able to concentrate on making love to you. Let's get this over with and see how comfortable my bed is."
I was smiling as I said it and he joined me. It was such a shy little smile though, I wanted to eat him. Instead I planted another kiss on his lips, only this time it conveyed all my pent up feelings of love and lust for this man child.
On my bed with him on his back and me propped up on one elbow I told him how beautiful and sexy I thought he was as I stroked all of his upper body. I leant forwards occasionally to give him a kiss and continued stroking until he started to pant, then I swivelled round so that I could use my mouth on his cock and balls. That was definitely a no contest. My mouth had taken his glans in and my tongue had just started licking it when he had his first orgasm. I gulped his jism down, greedily, I wouldn't waste one gram of his love juice. When I was sure I had it all I swivelled again and rolled him into my arms, continuing to stroke him. He had reverted to a little boy. I felt that he was ten years old again instead of nearly eighteen.
"Oh John, that was awesome. I'm sorry I came so quickly."
I kissed him again.
"It doesn't matter how quickly you cum, as long as you enjoy it. I'm going to do it again in a few minutes and I'm sure you will last longer and your orgasm will be more intense."
He looked in awe at that comment, I suppose the orgasm from your first blowjob is so much more intense than anything before that you can't imagine it getting better. Well, it was for Troy. He blacked out on his second one. I took a long time to bring him to orgasm, delaying it several times before I eventually let him cum. The volume was incredible and the scream would have woken the whole neighbourhood if we had been in my villa. When he came to he was wrapped in my arms being gently stroked. When his eyes opened they looked into mine with wonder and my smile showed him my pleasure.
"How do you feel Lover?"
"I don't know John, that was too wonderful for words."
Then he burst into tears and sobbed his way through, "I think I love you, is that alright."
That was definitely more than alright.
"Mmm., I think I can live with that. I've loved you for months."
That stopped the tears, he pulled away from me enough to see my eyes.
"Really John?"
I was laughing as I spoke.
"Yes, really Troy. I think I started to love you the first time I saw you and by the end of the month I would have sawn my arm off to be able to do this."
I could finish this story here because both of us were in love. It was going to be purely a matter of time before we went anal, and before I worked things so that he would be with me forever, well, almost.
++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ A few more adventures for our two love birds in part 2.