I agreed to crew on a yacht and I ended up
Sailing Into The Unknown
It was not what I signed up for or expected.
I had just finished college and was trying to find a full time summer job in the interim I had agreed to crew for someone on a large cruising yacht over a holiday weekend. Plan was the owner with three crew members would sail the yacht on a four day Cruising Club sail.
It was one of those warm sunny days when I arrived at the marina with a weekend kit bag in hand I had been given a pass code for the gate into where the yachts were berthed and its berth number.
Took me about 15 minutes to find ‘Temptress’, I knew it was large but it must have been over 45 feet with a 50 foot mast and 10 foot beam, it was the largest boat on the pontoon.
The owner was on deck he was in his mid to late fifties wearing white shorts and matching deck shoes no top as I walked towards him he recognised me from the photograph the crewing agency had sent him and waved, then came down onto the pontoon and introduced himself.
“Shane my name is Sir Richard Roper but call me Dickie everyone else does.”
We exchanged first time greeting as you would expect his yacht got the highest reviews from both of us. Niceties done he invited me on-board to stow my gear and offered me a coffee which I accepted; suggesting.
“As it is such a nice day why don’t you dress down?”
“Okay great where can I get changed?”
He pointed in the direction of a large forward cabin.
“Just in their, that’s also where we will all be bunking.”
I was about halfway through getting changed when he came in with a mug of black coffee, at that point all I had on was my black G-string. As I glanced round I noticed out of the corner of my eye he was eyeing me up, I felt a little uncomfortable as he suggested.
“Let’s enjoy coffee on deck in the sun.”
Bit lost at to what I should do quickly pulled on my shorts after retrieving them from the bottom of my kitbag and followed him up on deck. We sat down together at the large 6 foot diameter old world type wooden spiked wheel which was very impressive; as he said.
“I have just had word from the crewing company that the two other crew members have had to pull out due to unforeseen reasons.
Although I prefer to be over crewed this yacht is geared for single handed sailing which I have sailed single handed many times. If you are up for it I propose the two of us take it out for the weekend as the weather forecast is light winds, smooth sea, sunny and hot.
It will be a challenge leaving the marina given our size and our 9 foot draft which means we need to leave on the early morning high tide to clear the harbour bar.
What do you think?”
“Okay I am happy to do that if you tell me what you want me to do.”
“Great finish your coffee and I will give you a tour of the Temptress and her workings.”
We headed up onto deck both wearing only shorts and deck shoes which are a must for working on deck given the number of hidden deck fittings, I had completed my induction on the engines, deck workings and sail layout.
Being fitted out for single handed sailing everything had its place and was simple to work.
Finished with the induction we returned to where we had our coffee this time we settled on cold beer and sandwiches out of a packet which was very welcome as I had been traveling all morning to get here.
Dickie explained he was the outgoing CEO of an Oil and Gas company and that he was ousted in a recent Board Room debacle over selling off re-drilling rights. He sounded very unhappy about it.
However he managed to retain his position as Chairman of the Oil and Gas consortium, a political pressure group that wielded a lot of pressure both in industrial and governmental circles.
Inherent in this position he was also the Chairman of a charities commission who managed charitable funding from the Oil and Gas industry. This weekend’s bash was for a blue water cruising club’s first flotilla meeting of the year.
Originally plan was the crew would have a get to know each other meal in a local pub, although we had already done the get to know each other, we were still going to have a meal in the pub.
After we cleared everything away including checking everything on deck and below was securely stowed and the alarm set which is quite sophisticated given the value of the equipment on board.
We chatted as we walked over to the pub still only wearing our shorts and deck shoes but had taken our shirts with us for when we went into the pub to eat.
Dickie explained he knew the bar owner from their days together in the Royal Navy, he was a Commander responsible for Fleet fuel logistics on a large fleet replenishment ship and Colin the Senior Steward Chief Petty Officer. The ship was old and surplus to requirements and was being paid off as were the crew.
Dickie joined an oil company in West Africa with its head office in London, Colin took a tenancy of a bar in London near Dickie’s office. Later Dickie managed to get him backing to buy a pub and they meet up when they can.
Dickie never said why but he was very upset about how and why he was ousted from his CEO position other than it was because of something from his past in the Navy and not being prepared to sanction one of his co-directors friends of a friend receiving a re-drilling contract.
I shared with him that I recently had my life’s plans upset’s too, although I had passed all my exams something that happened in my past may block me going to University next year and possibly force me to re-sit two of my exams.
It was now with the examination board for their decision which was not due for a couple of months, either I get to go this year or take a year out and go back packing until I could re-sit my exams.
By the time we arrive at the bar we were ready for our beer and burger, we sat outside in the warm evening sun and chatting about our past’s but did not touch on our current woes.
Dickie saw his friend Colin appear behind the bar, excused himself as he went up to see him and get more beers. I was sitting there alone watching the sun go down over the marina and the remaining beer in my glass evaporate away.
I was awakened out of my beer trance when a fresh beer appeared in front of me, I looked up as a voice said.
“For you; you don’t remember me do you?
“Sorry no.”
“Possibly it’s you don’t recognise me with my clothes on.”
It came crashing back to me like a thunderbolt of guilt.
“Yes I do now; thanks for the beer.”
At that point he walked off as Dickie came back and asked.
“A friend?”
I was never very good at winging things.
“I don’t remember his name but I think he was a guest speaker at one of the business class lectures I attended.”
“His name is Jack Hargreaves, a business fixer based in Panama and as crooked as they come I wonder why he is here, he is terrified of water and boats.”
I looked up in amazement at his statement as he explained.
“He fell in off my boat quite a few years back after we had a heated argument about a business deal. However, time to head back to the Temptress as we have to be up and at em to catch the tide in six hours.”
We had another beer on deck before heading below, undressed in front of each other it was then that I noticed Dickie shared my views on erotica underwear.
The way he watched me undress sort of declared what his preferences in life possibly were.
I wasn’t so uncomfortable about it now that I understood him a bit better.
Four in the morning my phone alarm went off, Dickie was already in the galley, I could hear and smell bacon cooking and fresh coffee brewing.
I stowed my bedding and headed into the main cabin area wearing only my G-string underwear.
Dickie had his shorts on.
Don’t know maybe I was sort of sounding him out.
We sat close together hard not to in a yacht quickly devouring our breakfast, tide waits for no man our hangover from last night helped us on.
After clearing away we headed to the combine heads (toilet) and wet room shower which had a complicated array of valves.
I stripped off naked and stepped into the shower area Dickie followed my lead we were rationed to a three minute shared shower.
It was quite erotic as Dickie leaned over and pressing and rubbing our naked bodies together as he opened and shut a labyrinth of valves in front of me.
Cold then warm water cascaded out I was starting to get aroused by the body rubbing I am sure I could feel Dickie getting aroused behind me.
We faced each other then started to wash each other without prompting or gesturing, the three minute timer kicked in and the shower stopped with one last belch of cold water.
The cold water shock brought us back to reality, we had to help dry each other due to the confined space.
Towels around us we headed back to the bunking area to get dressed.
We had agreed last night over beer suds to follow a tradition where all the crew wear the same deck gear arriving or leaving harbour.
Dickie produced loud rainbow coloured speedos, white polo shirts with rainbow piping and matching rainbow coloured deck shoes.
There was now no doubt where Dickies preferences lay between the deck gear, this morning’s shower and admiring glances, which I now found quite endearing.
We dressed without comment my mitigating assumption was the marina would be empty of onlookers or photographers at four thirty in the morning as the sun was rising.
Taking a 45 foot deep fin keeled 10 ton yacht out of a crowded marina with nearly 40 feet of rigging exposed to the wind over the breakwaters was challenging.
Dickie was standing on top of the wheel box giving him better all-round visibility, spoked wheel in one hand and other on the remote engine controls.
What I didn’t anticipate was the level of noise of the big diesel pounding away waking everyone in the marina.
I was on the foredeck as look out, fender, wayward rope and line manager.
A wayward line overboard could foul the single propeller in its dead-wood, lost propulsion would mean a collision due to tight constraints of the marina channels.
As we headed for the harbour bar I saw a television film crew panning in our direction and a number of onlookers on the breakwater with cameras with long telephoto lenses on them.
Too late I was about to be filmed wearing my LGBT gear.
We were now good to go and lined up to cross the harbour bar as Dickie waived me to join him at the helm.
As I turned round something caught my eye and looked up, from the mast head about fifty feet above me was a ten foot long LGBT coloured streamer waiving widely in the wind.
We both stood there together at the wheel, dressed like manikins promoting LGBT gear.
As we crossed the bar we must have bottomed or were hit by an incoming wave, as the boat lurched momentarily I partially lost my balance, Dickie put his arm around me to steady me.
As if in harmony the telephoto lenses and the film camera looked in our direction to capture our moment of inadvertent endearment. That is what it must have looked like.
Clearly because of Dickies recent public prominence as an ousted CEO of a large Oil and Gas company and our age differential my 22 years Vs his fifties we were going to attract media attention.
As we exited the marina I spotted another film crew on a high speed launch and a second television camera crew on the breakwater.
We started to set the sails which attracted attention the way the sails rose and unfurled automatically all in harmony with each other.
Dickie was now down at the sails control out of sight of the cameras and I was standing alone on the wheel box controlling the helm with one hand on the shrouds steading me.
I could have put it on auto pilot but I was getting a thrill of helming the boat even if it was just into the wind as the sails were being hoisted and yet to catch the wind.
I was now very colourful and visible to the photographers and onlookers who seemed to appear out of nowhere, it wouldn’t take them long before they found out who I was.
All it would take was a call to the harbour Masters office, all comings and goings are recorded for security and safety purposes.
We were now 3 miles offshore not visible to anyone or telephoto lenses, engine turned off enjoying the silence of drifting effortlessly through a millpond sea under sail with helm under auto pilot.
Dickie came over handed me a mug of aromatic freshly brewed coffee, even that was done automatically by pressing a button on the control panel; sat down beside me and said.
“I am sorry if I embarrassed you by having you wear this club gear. The crewing company who put us in touch with you had assured us that you were gay and out. Also you had signed all the filming waivers.
If you feel embarrassed or uncomfortable wearing the rainbow gear, please go below and change?”
As I looked at him I could see he was truly regretful, impulsively I said.
“NO, no I am OK with it now.”
I then asked him.
“Are you gay?”
He looked directly at me as he said.
“Yes I am; bent as a 9 Bob note, you may take the man out to a drilling platform, but not from who he really is.
Are you gay or ever participated?
Does it also have anything to do with the problems you are having with your college exam results ratifications?
If it is I have had that a few times like that in my life that’s the reason why I had to leave the Royal Navy and was voted out of my CEO job?”
One of these questions you never want to answer, I now trusted him anyway I wanted someone to talk to about it and advise me what to do and gain his trust in me.
“No I am not gay although I had; still have; friends who are openly gay and closet gay.
Last Easter we were having a leaving do for one of my college lecturers Craig Docherty, it was a badminton club doubles competition named in his honour.
Don’t know why but he selected me as his partner, we played well got through to the semi-finals before being knocked out decisively by two openly Lesbians who wore incredibly short reviling white skirts and independently sprung sports bra’s; distracting.
Between games we chatted about each other’s life since the pandemic, Craig was gay and had had a number of boyfriends over the years. His teaching contract was not to be renewed this financial year, funding cut backs or something.
His plan was to fly back to Australia via Thailand in a few days to be with his partner who managed to get him a two year contract in an engineering college about 100 miles outside Perth, in the boondocks to use his wording.
We went to get a coke from the vending machine, on our way there Craig touched my hand and nodded for me to follow him; I didn’t know why; yes I did.
We ended up in the workshop locker room area as he closed the door and locked it, my heart was pounding with excitement and anticipation.
I was leaning on a sink as he pulled my polo shirt off over my head, I reciprocated with his shirt. He leaned over and kissed me on the lips it wasn’t long before we were both actively tongue wrestling with each other.
I felt his hand slide down my side and under the elastic in my shorts then he reached up and guided my hand down onto his shorts waist band invitingly.
From our health lectures this was a classic way of inviting and accepting the offer of consensual sex.
I instigated it all by sliding down his shorts first, he quickly followed, not long after we both stepped out shorts tangle I could feel both our hard-ons rub together, it was erotic ecstasy, then I felt him hold my shaft and gently caress it.
It only took a moment before I started to feel a build-up start, after he got me going kneeled down and started to give me a slow oral massage, my hands were on his shoulders steading me as he started.
I was so excited I couldn’t hold back for any length of time, I was purring like a cat as it left me and erupted over us.
I stood their drained but still in an erotic euphoria I turned and was looking at him in the mirror above the sinks I could see he was about to apply lube.
When he did he reached in, what a turn on I could feel my hard-on return as he copiously applied lube.
Slowly he eased in I could feel him press until he started to travel, I felt I was holding him back, then bang he was in and started a slow, slow, quick, quick, slow rhythm, he quickly found my spot and started to exploit it.
My ecstasy went into overdrive, I could feel myself start to drip just as his rhythm became erratic, his pace quickens, his breathing approached a vocal climax as I readied myself.
It happened as a warm fulfilling rush which was intoxicating, we stood there coupled as his load abated away onto the floor.
I turned and we were now facing each other both still deep breathing when he said with a slow deep breath.
“Your turn.”
He reached over and retrieved lube from the sink soap holder, I later found out this was a popular sink and had enhancements made.
I felt it on my shaft as he rubbed it on then he leaned on the sink invitingly, I accepted his invitation.
I pressed it went in without hesitation, obviously I wasn’t his first visitor that didn’t deter or hinder me.
Off I went impatiently and enthusiastically like a slow steam piston gaining momentum with ever deeper exploring strokes.
I felt the phantom squirt and eased to a more sedate slow, slow, quick, quick slow rhythm.
The pressure within me raised, my ecstasy pulsed eyes closed in concentration as it reached the got to let go or burst point.
The discharge seemed to go on and on, Craig moaned or whatever as I withdrew could feel the warm blowback.
My breathing was now deep and exhaustive, Craig’s too, we were now facing each other as we heard in the distance the flop, flop sound of trainers on the concrete stone tiles heralding someone’s impending arrival.
Well choreographed we lifted our kit and headed into two well separated cubicles, I quickly dressed before anyone came in and left the cubicle with a flushing encore just as they arrived.
They quickly disappeared into a cubicle without comment.
Outside the door someone walked pass me and into the toilets Craig emerged immediately afterwards smiled knowingly that our sink and its dispenser were about to have fun.
We headed back to the games hall they were about to finish our lesbian friends were now the undisputed champions.
The inevitable farewell speeches made and gift presentation to Craig, photographs with the winners of the Craig Docherty Farewell Cup and my first kiss from two lesbian’s which appeared in the front page of the college paper and its LGBT newsletter.
What was said about the kiss was what legends were made off; at least for a few days.”
Dickie kicked in. “Don’t stop there you have my full attention and admiration.”
“I have to take a step back to when we had the Pandemic and we were locked up in our Halls of Residence for almost four months.
Craig organised online classes for us, 14 out of 20 students joined in but he had to pay the Zoom fees at commercial rates the college administration staff were all sent home on full pay as Craig was a contractor not staff he wasn’t getting paid.
Classes were 9.30 to 15.30, Craig couldn’t continue financing it, however one of our class students found someone who would provide a free conference service for us if we provided online services for their clients.
Including Craig we all agreed.
My assignment was to promote manikin sales for G-string underwear, potential buyers would be able to see me wearing mine on line at any time including during our daily on line lecture.
It didn’t seem so bad, as it was boring being locked up and being vanilla all day.
This is how I developed a fetish for kinky underwear.
We did our classes by day we all had different apparel to model.
One night I received a request from client 972358, which I would get paid extra for. They wanted me to pose with rather provocative underwear on for a sales poster.
The next night a request came in for an all-nighter life modelling for ‘online art student classes’ I was to wear a Greek style white skirt and red knickers, that’s all.
Client 972358 came back again they were looking for me to wander naked about my room all night and were willing to pay me well for it; I declined.
I wasn’t comfortable about doing this and videoed Craig on WhatsApp, he said its okay these are Asian sites so nobody will recognise you.
To make you more comfortable about it we will strip off and do our 1 to 1 session naked this afternoon.
After that afternoon session I confirmed I would now do it that night on line.
I wandered about my room naked answering texted or verbal questions about me it was quite exciting. Later on I could tell it was maybe with just one person possibly Asian from the accent.
I suggested they join me on line naked and see what it was like.
I couldn’t pronounce her name so we agreed on Pauline which she really liked she was currently an erotic club dancer in a Thailand night club.
I think being locked up alone all day for weeks on end and finding someone to talk too clouded my judgement.
Anyway at her suggestion we ended up laying in bet watching and talking to each other as though we were both together.
Then she gave herself a finger job and I joined in and gave myself a hand job until we both climaxed.
The following night Pauline direct messaged me asking me to do it again, which I was really excited about until she told me.
We had been being streamed together around the web last night and her employer wanted us to do it again and offered us a considerable amount of money to do it.
She needed the money to help feed her family and save money as she has been accepted as a student at a dance college near me and that’s why she wanted me to do it again with her.
We ended up with a one hour slot every other night and I gave her an open invitation to come and see me when she arrived over here.
This or something erotically similar was a common request but we were all able to study and make money at the same time.
We never asked who was at the other end of the camera I think we all knew but didn’t want to know, we were in survival mode.
Quarantine ended but the request kept coming in.
By now we were able to socialise one free night I was in my friend Tom’s room. Tom and I had history in my fresher’s second week he took me to a gay club, I got bluttered.
Woke up the next morning in his bed naked, we had been banging each other.
Didn’t believe him at first until he showed me a video, from my camera phone, of us banging each other enthusiastically.
A WhatsApp message came in for Tom, who I knew now to be on the game, for a gay twosome money was astounding.
We had to wear our pandemic masks no faces so I agreed, we had quite a night all being streamed live for client 972358.
We never found out or cared who they were.
Craig left for Oz, the following week I received a WhatsApp from him with a picture of him standing in front of Sydney Harbour Bridge and the Opera House plus two videos.
One of me banging Craig at the sink and one of him banging me, only my face was visible. Message said phone the Admiral and gave me a Plymouth number.
After I got over the shock I phoned said who I was and that Craig Dockery gave me his phone number.
All he said was I was expecting your call I will send you a name and address.
Two minutes later a message arrived with a name, address and time.
I trusted Craig so I went; it was an exclusive apartment block in a high class area in the city which you rented for a day or a week at a time.
Buzzed the entry system and went up to the fourth floor, he met me at the elevator door and invited me in.
I didn’t know him but I knew from the way he looked at me what he wanted. All he said was ‘bedroom or living room’ I replied.
‘Your choice.’
‘Ok here and now.’
He had me slowly strip naked there and then in the hallway as he intently watched me. I was quite good at doing that since Tom showed me how.
He then partially stripped and started to bang me aggressively against the wall, no messing about took him about 10 minutes to climax.
I dressed and left.
I messaged the Admiral or whatever his real name was.
His reply was ‘£400 has been deposited in your bank account I will send you details of your next assignment in two days.’
Which he did, although not as brief a visit another £400 was deposited in my bank account.
This went on for the next three months at a rate of three or four a week this was in addition to my now bi-nightly show with Pauline.
A few days ago I received a letter from the Police saying Craig Docherty was being actively investigated for Soliciting did I know where he was and could I come in and see them.
I explained what happened and everything between us being consensual, they never mentioned the financing of the Zoom classes so I didn’t mention it.
They made it clear that they knew what I was currently up to, but as it was perfectly legal they had no interest in it. But still pressed ‘did I know where Craig was?’
They explained he never arrived in Australia and made it clear that they knew about the WhatsApp message I received. Apparently it had originated in Panama along with 20 other like messages enticing students. Three of these students had reported it to the college who in turn had contacted the Police.
I didn’t know anyway their was only 14 of us in his on-line class not 20 all through necessity, none of us would have shopped each other or ourselves to the police.
Didn’t make sense.
The college contacted me a few days later telling me two of my exam results and my annual assessment, all submitted by Craig Docherty were being set aside while they were being investigated until such times provenance is established. This may take two or three months.
Meantime my application for University would be held in abeyance, I may wish to consider other options until this matter is cleared up.
That week I received your invite to join you in this long weekend cruise, now here I am confessing my sins. Do you want me to leave?”
Dickies reply in his dominating CEO authoritative voice.
“We are 15 miles offshore and I need you to help me sail Temptress?
Anyway my background is not as exciting as yours; regretfully.
I joined the Royal Navy out of University when I was 23. My first gay escapade happened during my first year when I was home on leave and at a friend’s coming out house party, I met someone we ended up back in bed at his place, we had a wonderful night.
Back at the Royal Naval College in Dartmouth it didn’t take long before I met likeminded Naval cadets, we had to be very discreet but that was half the fun.
I had over ten posing during my Naval career, my last posting was as a fleet refuelling officer onboard a replenishment tanker that was being sold off to the Malaysian Navy.
I was to be posted back to London but an urgent reposing in Bangkok came up to fill in for someone. I really enjoyed the posting however, one night at a very salubrious sex club.
I ended up in bed with one of their male host’s; honey trap.
We had a discreet affair and the time of our lives, I travelled a lot and he came with me. One day the trap was sprung they wanted some favours from me.
As I had just accepted a firm job offer through the old boys club with a major oil company in West Africa, I told my superiors and resigned my commission their and then.
I went to West Africa on an oil production platform as its fuel management Director then moved to London met up with Colin again, became very successful rose to become the CEO of the Oil and Gas exploration Company.
Recently I was asked to sign off a re-drilling contract to a very dodgy company, I refused.
My past sins in Thailand and Panama where another gay tryst’s happened went public, I had to stand down from my CEO position.
But they couldn’t do anything about my Chairmanship of Oil and Gas Consortium. I had too many contacts who owed me favours.”
We were sitting on Temptress wondering what we will do next when Dickie said.
“Let’s go below together and explore options.”
We both went below together I kicked off my deck shoes, I knew what he wanted the way he was looking at me I was feeling that way too.
He came over to me, only a couple of steps, put his hand on my hips and his fingers in the band of my speedos.
We stood there eye to eye I put my hands on his speedo’s thumbs in his band instigating proceeding as I slid them down.
They dropped to the floor we both could feel each other’s warm bodies press together.
I sat down on my bunk as he kneeled over me it didn’t take long before we were enjoying each other. It was hot, sweaty and demanding as we relentlessly enjoyed each other.
We showered together, much longer than the three minutes we did the first time, you can and we did in the confines of the shower area avoiding the labyrinth of on off valves.
We had worked out a solution to both our dilemma’s, went back up on deck and sailed that day wearing only our rainbow speedos and deck shoes, it was a fantastic day’s sailing.
Later we made a hearty meal as I was eating mine I noticed the cabin camera on light were illuminated we had inadvertently filmed ourselves together. The deck mounted cameras were on the same circuit.
We both enjoyed the concept that we were filmed, then it occurred to us they were not copying but streaming live back to the film company.
That night we anchored in a sheltered bay.
We arrived back at the marina along with the rest of the flotilla of yachts. After docking the film director came over and said.
“Do you want to see the edited film before we release it.”
Dickie in his authoritative voice said.
“No, no just release it.”
Looked at me said.
“Do you want to see it first?”
“I said.
“NO!”
That’s how it came out and we came out in public we still have the unedited version of our first night together.
I had to re-sit my two exams the following year Dickie and I both took a year out to let things settle and sailed to faraway places.
The re-drilling contract turned out to be a dry hole, friend and friend of friends lost over $100M and Dickie got his CEO position back.
Later I went to work for a large international Oil & Gas exploration company and ultimately became Dickies replacement. I now have my own 65ft yacht and a nice assistant who looks after it.
Jack Hargreaves who lost a lot of money and Craig Docherty, were never seen again, whereabouts still unknown.
Also I became an Honorary Don at my old college and University.
©oxforddon