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My first time at Sea

Tags: gay, anal, stranger
I wanted adventure and I found it!

When we were first married, my wife and I had landed a sweet deal as the caretakers of a historic property on the coast of Maine .   We were newlyweds without a lot of money, but we lived in a small cottage over looking the harbor in one of those quintessential towns that the modern world had passed by.   Lobster boats still worked during the day and in the evenings pleasure boats plied the waters.   It was a short walk along the river to a cliff encircled harbor beach that hosted a resort hotel and a myriad of mansions that the owners called their “summer camps.”    We both worked at the hotel- I was a prep cook in the kitchen and Paula was the dining room manager.   It was a perfect summer of making new friends, living in a new environment and enjoying our deepening romance.


One of the highlights of the summer was our neighbor Chris.   We first noticed his boat, it was hard not to notice.   One morning the previously empty mooring off our property was suddenly occupied by a graceful 40’ sailboat.   I would later learn that it was a Hinkley Bermuda custom built in 1961.   It wasn’t the biggest boat in the harbor, but it had the best lines, a true classic that was lovingly maintained and had served it’s owner well.   Chris was from old money.   His last name was on everything in town and he was the last of the family line.   Along with this incredible boat, he also had an estate further up river and a lifetime membership at the club where we both worked.  


He was a curious character from a world we had only observed as hired staff.   We would see him rowing his dingy during the day making trips from dock to boat where he’d spend hours polishing some imperfection that only he could see.   We’d also exchange greetings in the evening when he strolling along the river to and from the resort where he took almost every meal.   Sometimes at work Paula would come into the kitchen and mention that he was dining alone, again.   None of the other staff knew much more about him then we did, but it was obvious that the other club members knew who he was and were polite, but not friendly.   He was ruggedly handsome with a weathered complexion, maybe 20 years our senior, impeccably dressed and it seemed odd that he’d be alone so much.   One evening as he was returning home from the club,   Paula invited him onto our porch for a nightcap.   To our delight he accepted.


As the summer progressed and our friendship grew.   I enjoyed Chris’ stories of the sea- he and his boat “Steadfast” had cruised the world and Chris was a master story teller.   Paula enjoyed the tales from his adventures in port and we both enjoyed a glimpse into the life of this ultra rich playboy.   It wasn’t long before we’d have the occasional dinner together at our house or as his guest at area restaurants that we could never afford.   Chris was very generous and made it clear that he enjoyed having friends on which to share his wealth.


One night after a bit too much wine, Chris confessed that he was gay.   He was relieved that it didn’t shock us and he told a very sad story about how his family and community had shunned him as a young man.     “It’s the reason I took to the sea,” he said.   “I couldn’t stand the way people here looked at me and I needed to get away… After my parents died, I thought about selling the house, but it’s been in the family so long I can’t part with it.   Besides this is a nice harbor to make repairs and re-supply.”    It must be a generational thing- in the early 1960’s when Chris came out there was still so much shame attached to homo sexuality.   Twenty years later when I was in college the Gay movement was going strong.   Almost everyone I knew was “Bi” and I had lots of offers to give it a try….it was just something that never interested me.


As fall approached the resort was closed for the season and Chris was almost ready to set sail for Florida .   We invited him over for a farewell dinner and he made me an offer that was hard to refuse.   “Brad, why don’t you come along…all expenses paid?”   I was surprised by the offer, I didn’t have much experience on the sea, but Chris explained that he could sail the boat all alone, what he couldn’t do was cook a decent meal.   I turned to Paula with my best “can I go out to play” eyes- it seemed like an opportunity for an adventure that I’d never get again.   She laughed as she gave her permission and we spent the rest of the meal working out logistics.   To sweeten the deal, Chris had thrown in a   generous salary, a flight home for me and a round trip flight for Paula to meet us in Miami .    “I’ve heard about you sailors,” she teased Chris “don’t go taking advantage of my husband at sea!”   “I like Brad,” he said, “but he’s really not my type….you have nothing to worry about.”   I think just to make sure I wouldn’t be tempted, Paula   used every opportunity during the days before our departure to remind me what I liked about the female anatomy.


On a slack tide in early October, we eased out off the mooring, waved goodbye to Paula on the shore and headed to the Atlantic .   Our first tack took us far out to sea, Chris wanted to “shake down” the boat in open water and teach me something about sailing before we hit any bad weather.   The plan was to head ESE past Cape Cod , then change to a SW tack and enter Long Island Sound.   Chris wanted to bring “Steadfast” through Hell’s Gate and make our first port of call lower Manhattan .    It was going to take a few days, depending on the wind, and I thoroughly enjoyed being at sea.  


Chris and I had decided that we would sail round the clock-   I had the last shift from 8pm until midnight.   Chris would check the charts, tell me about any waypoints and give me a compass setting.   Then he’d get into the forward berth for some shut eye.     Sailing on the open ocean in the dark is amazing.   My senses all became more acute- the smell of   sea, the sound of the waves, the stars above all seem more intense when you are alone in the night.   All at once I felt unbelievably insignificant under the expansive ceiling of the universe and immensely powerful as I harnessed the wind to propel “Steadfast” through the waves.   I imagined a symbiotic relationship as my hands felt the power of the sea through the tiller.   I now understood why old salts “ must go down to the sea again, to the roaring sea and sky.”


We smelled land before we saw it, especially as we got closer to New York City .   Although it had only been a few days at sea, my legs we’re unaccustomed to dry land and I laughed as I tried to shake off my “sea- legs.”    Chris had already made plans to tie up at pier near the South Street Seaport and after securing the boat we headed into town.   Chris had a hankering and we headed to Chinatown for dinner.   The place was a dump with all of the charm of a laundra-mat, but the food was fantastic!    After we stuffed ourselves, Chris said he was heading up to the Village- I was welcome to come along, but he thought the strip clubs around Time Square would be more my speed.    He hailed a taxi and handed me a wad of cash as we headed up town.    We parted ways around   Christopher Street- each of us ready to experience what the city has to offer.      “We leave on the outgoing tide,” Chris reminded me,   “be back aboard by 8!”


I wasn’t disappointed by the local talent.   Beautiful, naked women are always lovely, but my desire had been heightened at sea and these girls gave me an ache deep inside.   I wanted to be faithful to my wife- I had promised that I wouldn’t misbehave in port…I didn’t think that looking and some mutual touching violated that promise, but I came as close as my conscience would allow.   I finally stumbled out of the bars around 3am amazed that the city really never sleeps and started back downtown.   At a corner newsstand I picked up a couple of skin-mags   to keep me company on the cab ride back to the pier.    The boner that I’d had most of the evening needed some attention and I prefer to wank to photos- even if my imagination was filled with images of tits, ass and pussy from my evening of bar hopping.


Although Time Square was still alive in the wee hours, the waterfront was deserted.    As I climbed back aboard “Steadfast”   I knew Chris had returned.   I also knew from the sounds coming from his cabin that he wasn’t alone.     With porn in hand., I retired to my bunk for a little self pleasure.   The sound of skin slapping on skin and moans of delight heightened my pleasure- I didn’t really think about the fact that it was two guys going at it.   I stripped, laid open the magazines on my berth, grabbed some lube and a box of Kleenex…everything the well prepared wanker needs for a good time.   My boner demanded my full attention and I was so engrossed in bringing myself to climax that I didn’t notice a stranger enter the cabin….until I felt the hands wrap around my chest.


“Can I help you with that?” a husky voice whispered in my ear as strong, masculine hands worked their way past my abs and into my thick mat of pubic hair.   It wasn’t Chris- after enough time at sea, I knew the sound of his snoring coming from the other cabin.    Being still somewhat drunk my reactions were slow.   My brain was also numb- all the blood was already in my pulsing member and the feel of this unknown man’s lips on the back of my neck was driving me crazy! I started to protest, but I was so horny and his hands felt so much better on my throbbing cock then my own that my resistance was weak.   “Relax my friend, close your eyes while I take care of this…imagine it’s her mouth sucking you” he said looking at the open magazine.” The tips of his fingers gently teased my swollen helmet- stroking down on the head and twisting before pulling back up…. the same motion you’d use to juice oranges for breakfast.   His lips moved slowly, seductively down my spine. I felt my hips involuntarily arch towards him as his tongue explored the crack of my ass.     I spread my legs a little wider, pushed back and allowing him better access.  


The feel of his tongue pressing into my asshole sent shivers through me and made my legs tremble.   I leaned over further, opening my anus for him to explore.   He moved a finger into my wet hole as his tongue ran down the seam of my scrotum.   His lips puckered and sucked one nut into his mouth- the pressure in my scrotum and his finger pressing on my prostrate caused a delicious pain that I had never before experienced.   I had never had sex with a man, but I wanted this one to fuck me hard!   I had enough sense to reach for the tube of lube on my bunk and handed it back to him.   He knew what I waned and after giving my swollen testicle on more delicious suck he moved back, stood up and turned off the cabin light.    Before I could change my mind I felt the cold, wet, instant pressure of his cock at my puckered hole.   He pushed in and I pushed back, willing myself through the initial shock as his helmet violated my ass.   I was his bitch and would do anything to please him.   My cock ached for release as he pounded into me.   His nuts slapped against mine again and again- each time sending a renewed ripple of pleasure through me.   I couldn’t help myself, I groaned with delight and then buried my face deep in the mattress to muffle the sound of my pleasure- I didn’t want to wake up Chris when his lover was balls deep in my ass!  


Our breath was growing harsher as the pounding continued, then my mystery man pulled out.   I felt so empty as he turned me over onto my back.   In the dim cabin light, I couldn’t make out his features as he moved my hips and entered my gaping hole.    His cock felt even larger then before as he thrust and grunted.   From this angle I could stroke my cock   and felt the volcano building in my sack.   He grunted with a mighty thrust and I could feel his hot seed explode in my ass.   His spasming cock sent me over the top as my first cum shot splattered his stomach.   He pulled out of my ass, now dripping with his juice and engulfed my cock in his mouth before the second shot of cum pumped out of me.   I’d never been sucked like that before, his mouth pulling every drop from my aching testicles.    I could feel one nut, then the other being drained of seed as my cock softened in his mouth.   I lay spent and exhausted as gentle licks and kisses lulled me to sleep.


I didn’t wake up the next day until we were already leaving the harbor.   I stumbled on deck, squinting at the morning sun…..I must have looked like hell.   “late night?” Chris asked a little nervously, wondering if I had heard him and his friend.   “You were already snoring by the time I stumbled in,” I said and he relaxed.   I never confessed that we had shared a friend.   The rest of the trip was uneventful and I was glad when we arrived in Florida .    Paula was there to greet us on the dock.   We all went out to dinner and shared our sea adventure with her.   Chris skipped over our night in New York and I didn’t correct him.   I’ve never been tempted to repeat my one homosexual experience, but sometimes when my wife sucks my cock I imagine a stranger’s talented mouth and my thoughts return to the sea.

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