My story is a story of sexual change of pace. One that didn't change my life, but altered my perspective.
I was looking at the classifieds in the local paper. What I was looking for was something to do. I had just been dumped by my girlfriend of the past year. Not that I didn't see it coming, but what I never expected was many of my friends, had become her friends. The breakup left me more alone that I would expected.
So I was looking for something to do. My regular summer routine of playing in a volleyball league was out. In any breakup, someone will get the record collection and someone will get the cat. Sharon, my ex, got the volleyball league.
The toughest thing about such a split was living in the small Upstate New York town that I lived in. There weren't many options available to a single guy. I knew had to find something, because I was masturbating at least once a day and I needed something to take myself away from constantly pleasuring myself.
I was looking at the boat listings. When I was in my early 20's I had a sailboat and thought it might be a fun thing to begin again. At the very least it would give me something I could do alone, which seemed to be what my future presented.
Listed with the boats was an ad for a 'first mate.' The whole ad read: "Sailing grandpa, looking for first mate on my little dingy. Seasoned salt will gladly educate a willing sailor. Call: 555-2625, if interested"
Now before you get ahead of me, yes it is easy to see there are a few innuendos in that ad, but my interest to find something to do. The fact that it was a grandpa writing the ad gave me no reason for concern. In hindsight, I may have even purposely disregarded the thought because I saw it as a way to spend the summer sailing without having to buy a boat.
I called the number and over the telephone introduced myself to Jack. I gave Jack a run down on my experience and lack of knowledge. That when I sailed, it was on a small Rebel sailboat and because I was mostly self-taught I never learned much of the terminology.
Jack told me that he would be glad to school me.
My first inkling of what was to come was when he told me I wasn't "the first virgin he had to train on board his 30 foot boat."
He gave me directions to the Westport Marina and the slip that he kept his boat at. We arranged to meet that Saturday for a shake down cruise.
I arrived on time, 8 a.m. As I walked down the dock to Jack's slip, I noticed his boat was the only one that was facing bow out. The name 'Jack's Salty Dog' was toward the dock. Coming out of the hatch of the Salty Dog with two mugs was a man that was two parts Ernest Hemingway and one part Santa Claus. I was a little surprised. Here was a robust silver bearded 70 year old. Jack had told me his age and I had pictured a frail slight man.
"Andy?" he asked as I stood at the stern of the boat and I nodded. "Come aboard. Your right on time, I have a cup of coffee for you."
I stepped onto the Dog and the boat moved a little. I took the coffee and knew it was going to be a fun summer. I had forgotten how comfortable I felt on a sailboat. Some people instantly feel nauseous or uncomfortable on a vessel that shifts underneath them, but for me it is paradise.
Jack said he had everything ready and we could enjoy a cup of coffee before heading out.
Jack told me a little about himself. He had never married, though he had had a couple serious relationships. He was a retired 'paper shuffler' from Albany, but now he split his time between NY and Florida.
By 8:30 he had me laughing at some of is stories and ready to sail. Before we pushed off, he took off his shirt. He was very hairy with a round belly and all of the hair was grey. Though he was quite spry, he looked like he could be twice my age.
My family has a history of smoking and early death, so it was natural for me to think of him as the grandpa I never had.
It was a great day for sailing. A consistent breeze and not many boats out. Most people were probably still mowing their lawn for the first time and putting a fresh coat of anti-algae on their boats..
Even so after a couple hours I was surprised to see Jack take a leak off the back of the boat. I just assumed he would use the small head in the cabin. He called me back to hold the tiller while pushed the elastic band of his shorts down and took a whiz.
Jack had a beautiful cock, smooth as it was big. I was captivated by the size and the fact it looked about half Jack's age. It made me wonder if being single might have preserved it. Distracted I had let the boat drift off course. I pushed the tiller, to right the boat and the jolt caused Jack to stumble onto me. He let go over is member and grabbed my shoulder with his firm grip, at the same time penis rubbed against my leg.
"Sorry," I said a little embarrassed.
"It's okay, not the first time I fell for a man," he said pushing himself up. It then occurred to me that Jack was gay. All the previous signs lit up like neon.
Without skipping a beat he put his arm around me so he could hold the tiller.
"What you need to do is to push your leg out," he said and I felt his firm grip grab my calf and move it. "It is only common to want to look around when you are out sailing, but you need to find a stable position. Later in the summer I will install the automatic tiller."
I felt an urge to push him away, or to tell him I wasn't gay, but he wasn't really groping me, just touching me. He was flirting with the line of what is acceptable and what isn't. Had we been in an office it would have been sexual harassment. Here it was instruction. Well except for the fact that his penis was still out, grazing my leg as he talked. I was afraid to look, but it seemed like his cock was getting hard.
"So you find spot on your leg to hold the tiller. It might not keep you right on course, but it will allow you to steal a few ganders at things you maybe should be looking at," Jack said and chuckled. I laughed nervously. The spot on my leg I was thinking about wasn't where the tiller was, but where is penis felt like it was burning a hole in my leg.
"I wasn't really, I mean that isn't what I was looking at," realizing even with a gold shovel I wasn't going to dig myself out of the hole I was in.
"What where you looking at?" he asked laughing and stood up, moving his cock level with my head. "Don't worry, you aren't the first person to stare at Jack's Salty Dog."
"I'm not like that," I refuted. "I am not saying what is right for you, but..."
He had told me several stories of debauchery but I just assumed there had been a woman involved. Jack had joked about a couple 'quick fucks on slow boats,' before, now different images danced in my head. Worse of all, I was horny, but not ready to be one of Jack's 'quick fucks' on any speed boat.
"I know, you have a girlfriend...or had a girlfriend," he was still joking, but that comment stung and I looked at him, only to be face to cock with is penis.
"Sorry," Jack said and tucked his penis into his shorts. "I didn't mean that."
After a pause he held out his hand, "Friends."
Several thoughts bounced through my head, his comment about me having a girlfriend was related to the fact that I had mentioned Sharon no less than five times in our conversations. Clearly it was time for me to move on. I also was thinking that I really didn't want to go back, I was having too much fun sailing.
"I'm not sure if I should shake that hand," I said smirking.. "I'm not sure where it's been."
"I guess you have a point. Over the years this hand has been quite a few places." still holding out his hand he added, "Then again, I am not so sure I know were your hand has been."
"Well if it makes you feel any better, I usually wash it off afterwards," I joked and shook hands. "Friends."
In mock seriousness he stopped shaking my head and said, "Usually...?" Then let out a big belly laugh.
That seemed to break the ice. Knowing that Jack was gay and not really knowing much about the gay lifestyle I asked him about all the things I had wondered about. Things like if he always had anal sex with his mates (his word, since 'boyfriend' wasn't very macho).
I was learning a lot about things that I had casually fantasized about. When you masturbate like I do, you have a lot off different scenarios in your head. You also figure that in a certain situation you would know how to make a man cum. Between girlfriends, I thought about having a man suck me off and if I could reciprocate.
The conversation was mixed with educating me about sailing terminology. Around 2 p.m. we moored near the Burlington Marina and took his raft into the city for lunch. We walked to a brew pub and had sandwiches and a couple beers. The beers, the sailing and all the sun wilted me.
"You don't have any plans tomorrow, do you?" Jack asked as we were paddling back to the Salty Dog.
"Aside from maybe sailing again? Not really," I answered, when we talked on the phone we had broached the idea of sailing both Saturday and Sunday. "I guess I will need to mow the grass sometime. Why?"
"Well I thought maybe we could sail over to a little cove I know, and moor for the night. We could get an early start tomorrow, by being on the lake. I have a couple steaks in the cooler that would...."
"Steaks you say...why didn't you say that back in Burlington," I joked. "I would have bought some beer."
"Because I have a fifth of Glenlivet," he replied.
"I would have bought some ice," I said paddling a letter harder. "Guess I can drink it straight."
"Straight? Does that mean you going to bring up Sharon again," Jack laughed and matched my paddling pace.
"If I didn't think you would think it was an open invitation I would tell you to 'kiss my ass,' " I taunted.
"Smart move," he said as we pulled up to the Salty Dog. "By the way, I thought of the ice too."
As we sailed to the cove, Jack told me about the last time he had had sex, five years ago. Part of the reason for the five years of celibacy was he was in a no sex relation for a couple years. He couched the story with how nervous the guy was, that Jake was seducing.
"A year ago, we had gone to a really nice lodge," he laughed as he told the story. "Expensive dinner, wine, the who shebang. That was going to be the night. We had gone to the doctors and been tested for AIDs, I still have the form tacked to my bed.
"Then he backed out," Jack said shaking his head. He added that it was the end and joke that when you date someone that anal retentive you should at least be getting a blow job.
We got into a conversation about disease. It was interesting, because Sharon had been just as nervous. Even though we had been tested and she was on the pill, she insisted on using condoms, 'as a pre-caution.'
The cove was on the Vermont side of the Lake Champlain, which was the place to watch the sun set. Dinner was cooked on a little grill, complete with a couple baked potatoes and a salad. For desert we had cheesecake. I could see how Jack had gained his shape.
With the dishes done we sat on the deck watching the sun dip into the Adirondack mountains.
Splashing some more scotch into my glass and dropping a couple more ice cubes in Jack said, "This scotch has been waiting 12 years for a night like this."
"Red sky at night, sailors delight," I said holding up my glass in a toast. It was at this point in the evening I first thought to myself, 'I'd like to suck this guy's cock.' During the day I had a couple passing thoughts of what it would be like, but now there was some desire keeping it afloat.
After taking a drink, "I have always found a sailor's delight to be a hard cock." Jack laugh his booming laugh and drank again. His occasional references to sex was garnish to my appetite of physical craving.
Every once in a while a breeze would slip by, swaying the boat. The temperature was beginning to drop. The sun was down and clouds had filled the sky.
I asked him what made a man in bed good. I could feel the question increased a little sexual tension, but I was, as the boating term goes, three sheets to the wind.
"Are you just being curious or are you going to ask me to kiss your ass?" We both chuckled.
"I can't believe a guy your age is still getting it on," I was drunk and not able stop talking.
"Not only do I get it on, I also get it in...any way I can," Jack said, then, "though not much any more. Most of the guys my age are dead and the younger guys don't really think about making it with someone my age."
The scotch pushed another question out of my mouth before I knew I was asking it, "Earlier, were you getting a hardon."
I could tell the question made Jack a little nervous, I wasn't sure why. My only guess was he had a hardon right then. With the darkness, I couldn't tell. I was hoping he couldn't tell, because I felt a swelling in my trunks that I didn't want him to see.
"You mean in my 50's, that earlier?" he said brushing the joke aside.
I didn't respond, all I could think of was his smooth cock. It taken on an aura of grandeur in my mind. I was drunk and horny. In addition to the fact that I was alone on a boat with a man who had a beautiful cock and used to his cock being sucked.
I would be content to a life of only oral sex, in fact the only pleasant thing Sharon said when she told me she had had enough of me related to that. In a back-handed compliment she said, 'if you didn't give such good head I would have ended this months ago.'
"Let's just say, my first thought when you stepped aboard this morning was, 'he too hot to be gay.'
I felt a couple rain drops.
"So I am appealing to you?" I asked, holding back a giggle. I found the thought amusing. It was also ironic that even thought I was asking about my attractiveness, I was thinking about Jack's cock. My oral fixations were boiling over in a haze of alcohol and lust.
"It' looks like it is going to rain," Jack said, "I guess we won't be sleeping on the deck tonight."
"I never thought about that," I said. During the course of the day I had been down below, it was cramped. Then all of the sudden it started to pour.
Jack shouted a few orders, telling me what could be left out and what needed to be brought below. Regardless of of quickly we moved we were getting drenched and the rain was freezing. Fortunately it was warm down in the cabin. It was actually almost stuffy down there and had we not just come from a cold drenching rain it would have seemed a tad unbearable.
It was dark in the cabin and I leaned against the table to steady myself and to wait for my eyes to adjust. Jack came down the stairs and sat down what he was carrying. Then he walked right into me.
"Sorry, I was trying to get the light," he apologize, standing inches from me in the dark.
It was the moment. I could smell the booze on his breath. My mind was skipping over various thoughts, but lost for word to express them.
"It's okay," I said slipping to my knees....grabbing at the waist band of his shorts. "Lets leave it like it like this for a bit."
The boat lurched a bit as I pulled down his shorts. To right himself, Jack put his right hand on the table. I couldn't see the cock, but I had a memory of it. I was close enough to draw in a breath of his pungent excitement.
I pushed his shorts all the way to the floor. He stepped out of his shorts and sandals. I slide my hands on long his legs on the way up to his cock. The motion of my hands along his hairy legs slowed me down. My first thought had been to gobble him up, but instead I thought I should go slow. I leaned my head forward and kissed his cock, gently as I caressed the back of his thighs and ass with my hands.
I slid my tongue from the tip to the base. He was still somewhat soft, but I could sense his rod flushing with blood. It was a good start.
My nose nuzzled in his pubic hairs above his cock for a second, then I slid my tongue up his belly. I moved my hands to the front of his thighs, my right hand I moved up and cupped his balls. I took my left hand and slid my fist around it.
I could hear Jack breathing, but he was making little other sounds. He was as quiet as he had been the whole day. I was glad, conversation would have intimidated me. I licked the tip of his penis.
The rain was beating on the deck above and the wind had picked up. It was gently rocking Jack's Salty Dog, while my hand was gently jacking Jack's cock. My lips kissing the head of his cock.
The ambiance was everything.
I seemed to be succeeding at pleasing Jack. He rotated his body and sat on the table. Repositioning myself I took his organ into my mouth...or as much of it as I could. My tickled under his balls. He was hairless at his testicles. In the dark I couldn't see, but I knew it must be an interesting contrast from the grey hair on his chest.
Jack had been semierect when I started and now he had grown in my mouth. I licked excitement around the head of his cock. He had pushed himself onto the table enough that he could put the heels of his feet onto the table. In doing so he had knocked off his flip-flop sandals. I was using them as cushions under my knees.
I couldn't tell if his moans were genuine, or just a soft guttural prompting for me to keep going. Either way I felt a sense of power in pleasing Jack. I lathered up his cock with saliva and using my spit as lube I began to jerk him off with my thumb, while I licked his balls. One testicle at a time I would gently suck into my mouth.
"O....oooo, Andrew," he whispered in the darkness of the cabin. He used a completely different tone of voice. It was a soothing sound. On deck I was 'Andy' but with his balls in my mouth and his dick being whipped into a frothy orgasm, I was 'Andrew.'
"Mr. Andrew," I instructed after releasing his left testicle.
It was kind of an interesting play with role reversal.
While sailing I was the deckhand and he was the captain. 'Down below' I was directing the course. I put his cock in my mouth and as I slid my head away, I grazed the shaft with my teeth tenderly, against his skin.
"yes yes yes yes," his whisper sounded like the hissing of an air compressor. Then I flatten my tongue against his hotspot under his head. The boat was swaying against its moorings and Jack was lifting is ass off the table, twisting with delight. Wen he lifted I took the thumb of my left hand and pressed it against his sphincter.
'oooo yes Mr. Andrew,' came is approval. And after applying pressure with my tongue Jack came. I felt him tense up, ready to release and to be sure I knew, he whispered, "I'm gonna blow."
I took my fist and jacked him off as he squirted around my knuckles. Jack slide his feet forward, draping his legs over my shoulders.
"Mr. Andrew, that was quite nice," he said with slow breaths. "I definitely owe you one."
I started laughing.
"What?" Jack asked a little nervous, wondering what I was laughing at.
Our situation had struck me as silly. I could now see in the dark, with light driving through the round windows.
"You are quite a buffet, there on the table," I blurt out and we laughed together.
"Feel free to take seconds, but I will have to take a piss first," he said propping himself up on his elbows. I wondered if I should watch...knowing I would soon enjoy a beautiful cock again.