The 1990 Sydney to Hobart yacht race was memorable for a number of reasons. Rothmans took line honours only to be stripped for breaching advertising rules and I got to experience my first orgy aged only 19.
A mate of mine from university knew people connected with one of the boats in the race. He’d grown up around boats, was a few years older than me, and had gotten himself a gig crewing one of the yachts on its return to home port following the race. He got to choose his crew for the homeward voyage.
We decided we wanted to be in Hobart for the end of the race to take part in the post race festivities and after the resupply repair and refuel set off for home port on or just after New Years Day.
My mate, Mitch, had plenty of ocean sailing experience and the boat could be crewed by 5 fairly readily. The boat would accommodate 10 comfortably and had safety gear enough for 14 so with the crew of 5 decided (including me; I had no deep water sailing but plenty of time inshore) Mitch decided that it would be good to spend our time in Hobart looking for appropriate ancillary crew to accompany us back up the coast.
We arrived in Hobart on the morning of 28 December and checked in to a hostel near the Salamanca Markets not far from Constitution Dock. We had about 2 days to find 5-7 additional crew wanting to sail to the Gold Coast. The brief was simple. Crew members had to be good looking, single, and prepared to both work and party hard (sailing experience not essential but an advantage).
The boat owners were paying us a fixed rate for getting the boat back to home port and paying for provisioning which we were to get on board. Being young guys provisions were basic to say the least and consisted of some food and plenty of booze. Our return voyage was expected to take 12 days purposeful sailing. We figured that if we sailed with great purpose we could have some time at anchor for a bit of recreation along the way and if we extended our voyage to a planned 14 days we wouldn’t have to push too hard and still get some rec time at anchor in so our passage plan was amended accordingly.
During our discussions concerning ancillary crew we decided that it was just and proper that a small fee be charged for the privilege of crewing the boat mostly to offset the additional provisioning required.
Finding suitable, willing candidates did not prove difficult.
In the interim and between finding crew we took part in the festivities that the end of the yacht race afforded. The maxi yachts began to sail up the Derwent river in the small hours of 29 December and the Pubs around constitution dock were in overdrive as the crews disembarked and were out to celebrate.
We were in one pub where the only drink available was rum and Coke served by the jug which was being scooped out of canvas baths behind the bar. There was a constant pour of post mix Coke going into the baths and catering sized 20 litre drums of rum and bags of ice being dumped into the baths in an almost continuous resupply. It was mayhem. It was awesome.
The our boat finished late on 29 December and we went and had a drink with the skipper to take possession of the boat. The boat was in good order and we spent 30 December resupplying her and refitting some creature comforts like beds, below deck furnishings and so on.
New Years Eve and the crew for the return voyage assembled and we completed paperwork and so on. We were 12 for the return voyage. The 5 of us with sailing experience.
Our sailing tourists were:
* Marie and Freya – Swiss girls both 19 on a working holiday in Australia;
* Gemma – a 20 year old Kiwi backpacker;
* Clodagh – an 18 year old Irish girl on a gap year;
* Camilla – a 22 year old backpacker from Argentina;
* Kate from Florida who was in her early 20s; and
* Trinity – a 21 year old from Vancouver who was in Australia to attend University in Sydney.
All girls were quite different and all seemed excited about their trip.
After safety briefings and familiarisation with the boat the 12 of us went off to find a party and to see in the new year, not a hard ask in Hobart during race week.
We all got better acquainted seeing in the New Year and spent the night on board in anticipation of an early departure on New Years Day. There was a bit of kissing and fondling before we retired for the night but no real shenanigans.
We sailed by day and made our planned anchorages each afternoon. It was pretty chilled on board. The weather wasn’t bad and neither were the seas. On our second night at sea we anchored at Flinders Island and enjoyed some time swimming and relaxing after dropping anchor and again before heading into Bass Strait.
The Bass Strait crossing was choppy but not horrendous and the mood on board was good. A Bass Strait crossing does not lend itself to canoodling but after we got back to the calmer inshore waters of the mainland the atmosphere on board was starting to heat up and the sexual tension beginning to assert its presence.
The crew (that is the crew with sailing experience) were working during the day either under sail or under power and whilst not hugely strenuous a day of sailing tends to be tiring.
By night at anchor we’d have a few drinks and share a meal, play some music or card games before hitting the hay.
By about day 4 the assigned sleeping arrangements were out of the window and there was a significant amount of bed hopping going on.
Night 4 saw Clodagh find her way into my bed and we fooled around a little kissing and fondling eachother before she rode me smooshing her lovely pale C Cups into my face.
She had dark brown hair and fair skin which was dappled with freckles where it had seen sun. She had obviously worn a bikini under her life jacket in the last coupe of days as the pattern of emerging freckles on her shoulders, arms and chest painted the voids in her life jacket against the pale skin which had escaped the sun.
We could hear the sounds of sex coming from elsewhere on board which was pretty hot and Clodagh giggled as she listened and rode me. We looked at each other as we fucked and then Clodagh began to moan as her hips began to make circles and her rhythm quickened.
Behind Clodagh’s moans could be heard several muffled sighs and whispered uttering punctuated by louder moans and sounds of fucking.
As Clodagh came she let out a series of “*Oh My Gods*” in her unmistakable Irish lilt.
That seemed to signal permission to the others similarly engaged to disregard any kind of vocal restraint and the boat burst into a chorus of moans and ecstatic cries. The crescendo passed and silence descended followed by giggling and whispering and eventually silence followed by light snoring here and there.
Sleeping on board a boat can be challenging for many but throw in the sounds of fucking and it can be nigh on impossible until you’ve had a dose of sexual sleeping potion yourself.
The morning of day 5 brought bleary eyes and sheepish grins which quickly descended into gales of laughter as the soundscape of the previous evening was recreated in jest.
That night and the nights that followed were basically a repeat of night five except that bed partners changed or were supplemented. On night 8 I was showing Kate my brand of Australian hospitality when Freya slid open the partition behind which my bed was set up.
Kate was in the middle of sucking my cock and was doing a magnificent job of bringing me oh so close and then backing me off cumming. I had my hands on Kate’s shoulders stroking them and trailing my fingernails down her sides making her flinch as I tickled her lightly across the shoulders, down sides and around her breasts.
Freya said “*Fuck all I can hear is fucking and moaning and it’s making me hornier than I can handle.*”
Freya was taller. About 5’10” slim with nice shapely legs and pert little B Cups which were crowned by pink nipples which were currently pointing to the ceiling and looked as painfully erect as my cock which was spending quality time in Kate’s throat.
Kate was short at 5’1″ and and apparently was a hockey player she had great tits and a great arse.
I cupped Kates face as she withdrew my cock from her throat and kissed her deeply as I motioned for Freya to join us. I said to Kate “*Do you think we could relieve our friend of her burden?*”
The girls smiled and Kate said “*Sure, but she’s overdressed for this party.*” and reached over and pulled Freya’s bikini bottoms down.
Freya reached down and planted a deep kiss on Kate’s spit covered lips and licked the drool on her chin and then sat down by me and kissed me while Kate wrpped her hand around my twitching cock.
Freya let out a moan as she stroked my spit covered shaft.
Kate pulled Freya away and pushed me back onto the bed and mounted my throbbing cock. She reached out for Freya and her hand found her pussy. Freya grabbed my hand as my other hand grabbed Freya’s arse and slid between her cheeks from behind to find Kate’s fingers playing in the folds of Freya’s wet pussy.
I wriggled down the bed and Freya squatted over my face and lowered her soft, wet, hot pussy down on my waiting mouth as Kate began to ride me in earnest. I couldn’t see much from my vantage point nestled between Freya’s cheeks but the girls seemed to be enjoying themselves immensely. The girls came one after the other, I came hard, we swapped positions a couple of times the girls each loved to be fucked doggy so at one stage I was behind Freya fucking her beautiful hot, tight cunt as Kate lapped at her clit and my balls from beneath and Freya ate Kate’s pussy it was a blur and tangle of arms, legs and genitals.
The sex chorus was in full voice on the boat again that night and when day 9 dawned again the boat was full of bleary eyes, bed hair and sheepish grins. By this stage pretty much everyone had given up on wearing clothes whilst we were at anchor and we’d just jump into the clear waters of our anchorage to swim and refresh ourselves before getting under way again The boys would wear life jackets and board shorts and the girls would wear life jackets and occasionally bikini briefs when not at anchor. We were sticklers for safety.
After day 9 the boat pretty much turned into a free use zone whilst at anchor and the bed hopping was in full swing.
Day 11 we had a rec day at Coffs Harbour after mooring at the Marina on the late afternoon of day 10. Mooring meant hot showers, cleaning up the boat, disposing of the trash and resupplying. That night we decided to go out in Coffs and after hitting the showers and cleaning ourselves up we all got dressed up (as dressed up as a bunch of young yachties could given our circumstances) and went out for a meal and then on to find whatever passed for nightlife in Coffs Harbour. We had a bit of a dance and a few drinks and the onboard familiarity was hard to keep in check in public so after a fun night we all decided to head back to the boat.
That night was more subdued than recent evenings. Perhaps it was being near other people, perhaps it was the appreciation that our little cruise was fast drawing to an end and whilst there were shenanigans that night they were far less uninhibited those of previous nights. I spent the night with Camilla practicing my best Spannish as i demonstrated my cunning linguist skills (sorry, not sorry about that joke).
The morning of day 11 we had breakfast ashore and did a couple of touristy things in Coffs Harbour such as the Pet Porpoise Pool and the Big Banana (many many *double entendres* arising from that visit.)
We got aboard again about 2pm and decided to spend the night at anchor. We struck north and anchored off Angourie Point near Yamba on the New South Wales North Coast.
Before we had even left the Harbour at coffs the girls were stripped down wearing only life jackets so the boys followed suit and we sailed north in the afternoon sunshine all but naked.
We were watching the moon appear in the sky over the horizon as the sun set behind us as Gemma grabbed my hand and backed up to me pressing her body against me as she admired the deepening colours of night and emerging stars above the horizon taking in the view. “*I fucking love this.*” she said pointing out to the horizon and reaching back with her otehr hand to stroke my already semi erect cock stroking it to full attention. I returned the favour by trailing my hands down her toned belly and teasing her thighs, mound and outer lips with light touches. Gemma lent forward and grabbed the starboard rail and pushed her arse into my groin pushing me back so that she could put the head of my cock at the entrance of her dripping cunt. I pushed in purposefully and she shuddered, “*Oh Jesus!*” she cried out “*that’s a first*” as her legs began to tremble.
It was a first for me too, I’d never had a girl cum on first penetration.
“*Come on, fuck me*” she said.
“*I’m pretty sure that’s what I was doing.*” I laughed as I started to thrust and tried to establish a rhythm.
The gentle sea breeze and the rise and fall of the boat on the swell and the twilight made for a beautiful environment to indulge every desire and everyone was on deck fucking.
Before long towels and swags and cushions appeared from below deck and the deck turned into a mass of bodies engaged in various sexual acts changing and reconfiguring throughout the evening.
Maria had wanted to be spit roasted so a couple of the guys indulged her fantasy as teh rest of us fucked and looked on. Part way through she said she wanted to be made air tight and another of the guys joined in to fulfil that wish. Pretty soon Maria was the centre of the action as the girls took various roles in holding and stroking her or suckjng on her tits as they spilled from between the guys fucking her holes.
Gemma was playing with herself as she watched Maria and the scrum around and inside her, a ferocity in her eyes. She dropped to her knees and started sucking my cock and pumping hard as though desperate to make me cum as quickly as possible as my balls tightened she pulled me out of her mouth and aimed my cock at her chin and tits. I obliged by spraying a hot load all over her *decolletage*. She got up having received her load from me and went insearch of another contribution from one of the other boys.
Trinity then came over to me and brought me over to where Maria was fulfilling her air tight fantasy and pulled Brad, who was occupying Maria’s mouth, away replacing his hard cock with my spent one so that it could be revived by a flailing Maria.I then watched Trinity take Brad over to where Gemma was blowing another of the guys and suck him until he was ready to blow and aimed his cum all over Gemma’s back and shoulders. She and Clodagh then rubbed their tits in Brad’s cum and smeared it across Gemma’s back.
That sort of thing went on for God only knows how long. Everyone fucked Maria in one hole or another, Gemma was covered fro head to toe in cum. Girls and guys were smeared in cum and eventually everyone calmed down and lay around on deck spent and happy.
That was the first lull in activities. As we regained our breath and everyone took a hydration break the making out started out afresh and it all became another writhing mass of body parts. The energy seemed to be rising and falling with the swell.
We all slept on deck that night. Well *slept* is an overstatement. It seemed at any given time between twilight and dawn someone was fucking someone.
What I learned about orgies that day was:
* they can be awesome with people you know and trust and with whom you have already been intimate;
* they are awesome when they aren’t planned and *happen* spontaneously;
* it is better if the ratio of cocks to pussies is about 1:1 as no one feels left out;
* they’re best when booze and drugs are kept to a minimum; and
* when they’re good you don’t want them to end.
The breaking dawn saw us all rousing and untangling ourselves from those with whome me had entangled the night before. Nobody could wipe the grin off their face Gemma and Maria in particular.
We all took an early morning swim and washed the sex off us and made sail for points North.
We were all happy being basically naked but for our life jackets and deck shoes and the boat returned to its floating free use status and the nights were still as hot and as sexually charged as previously.
We reached Southport on the late morning of day 14 and handed the boat over after we disembarked.
We’d spent a fortnight basically fulfilling each other’s fantasies and had made memories that would last a lifetime.
I never saw any of the girls that helped us sail from Hobart to Southport but I often think about them.
As always I hope you enjoyed my ramblings and if you have any I am happy to receive your constructive feedback.
If you are moved to up vote please leave a comment as to why.
If you are moved to down vote please leave a comment as to why.
If you would like me to share more stories of my youthful escapades please ask in comments.
Source: reddit.com/r/gonewildstories/comments/sgtbyz/fucking_awesome_cruise_mf_mff_fmmm_orgy
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I’d read more 😏 I love a good sex story, especially with multiple people.
Yet another reason to get a sailboat
Cracking story. One of the best I’ve read.
Great experience, thank you for sharing…
I grew up on the beach, more power boats than sailing, but did a lot of sailing in college. Block Island race week is INSANE!!!
Dude this is a A fucking classic story. Your luck man who knows if these chicks were actual down with this. This a strong best to tell man
Fucking bastard, living out the fantasies I never will. Fantastic story, I am so very jealous.
Great story and very well written.
Great job. More please
What is give to be on that boat 😏 you’re a wonderful storyteller
Great story! Sounds like an amazing time! Love to hear more.
!subscribeme
Great story and shows how the owners seldom have more fun than the crew
Great story! Super sexy! Definitely living out a fantasy.
Can I ask a stupid non-Australian questions? Is this super common? Like, the idea of five random guys going around a harbor and asking random girls onto a boat for two weeks has me curious. Was there more “no’s” than “yes”? How long did it take you to find all of them? Were the chances greater because everyone in that town was there for the regatta, so they were looking for random cruises? Is boat race just a party where the expectation of these types of trips exist? (like in America, there is Mardi Gras where the expectation is for people to get drunk and flash their boobs in exchange for beads)
Thanks in advance. I look forward to more of your stories.
Orgies are the best, spent many a day and night doing the same. Awesome mate!
What a great well written story! I barely made it to the threesome
Sounds amazing not only the sex itself but experience and having such a cool memory to share with those people.
Kinda imagine it wouldn’t be the same nowadays especially with smartphones around.
I always wanted to spend a month in OZ.
Awesome take and one to remember always. Glad you shared it here for posterity and you inspire me to share some of mine some time.
Updateme!
Did you ever sail one of the Sydney to Hobart boats back again? And was it a similar experience?
Good on ya cunt!
(Sorry that’s the only Australian I know)
What a great story, thanks for sharing!