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Strange encounter, but very enjoyable

"Helping a frustrated couple on holiday"

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Author's Notes

"Not your usual encounter, more voyeuristic than anything else, but what fun. I'd have loved a repeat performance."

Lying asleep in the cockpit of my small yacht anchored a couple of hundred yards or metres off New Quay beach, the long one, not the short one, is not where or how you’d expect the oddest sexual encounter to occur, but it did.

Allow me to explain. The summer of 2025 was, and as I type, still is incredibly hot, and I was making the most of it. I’d sailed overnight to get there and was exhausted but as I’d planned to stay a couple of days I knew I was going to get some rest.

The nice thing about sailing solo is you can wear whatever you like, or nothing at all. I was asleep in the cockpit, working on my all over tan. The shape of the cockpit (how appropriately named) and the coamings hid me from passing boats and paddle boards, even if I sat up all anyone could see was my bare tummy and chest, and would be unaware I was wearing just sunglasses and a hat.

It’s thirsty work being asleep and I woke needing a drink. I sat up for a while to watch the world go by and to ensure there were no children on paddle boards or canoes before picking the right moment, standing to go down to the galley. I consider myself quite friendly and have often held conversations with swimmers going by, nice boat, where are you from, how long did it take to get here, do you handle the boat alone, what’s involved in owning a boat and many more questions. I have invited the occasional person and couples aboard, but have been very selective and careful.

As I sat there a couple sharing a big stand up paddle board went past, about 20 feet away. Both were standing and she, wearing a white coloured bikini which accentuated her tan. We all smiled and I said, somewhat clumsily “It’s good to see a man taking a rest for a change”, and quickly followed it with “Oops, was the politically incorrect and sexist?” “Sort of” she replied, “But not the worst I’ve ever heard, he’s much worse” nodding in his direction. Then the conversation started, “It must be ace with your own private sunbathing area, facilities for food and drink only feet away and no sand to get in those places that sand always seems to get.”

As we spoke the paddleboard was slowly getting closer with the risk of embarrassing a woman clearly younger than me I said “I don’t want to embarrass you, but you are drifting closer and I was working on my all over tan, I have a pair of shorts here, let me slip them on.” She laughed and replied “Whatever you are more comfortable with, I’m old enough and mature enough not to be embarrassed. Besides which we’re on a rented board and need to do some more paddling”, and with that off they went.

20 minutes later, I’d got myself a can of Coke out of the refrigerator, had returned to my tanning position and they came by again, a bit closer this time. “Sorry to disturb you again, we’ve been talking about your boat, do you mind if we ask a few questions? We’ve done flotilla sailing holidays around Greece and the Bahamas over the last few years and were wondering about the practicalities of owning a boat based in the UK.” By this time they were alongside, holding onto my boat with me on full display. After a few words had been exchanged I said “It’ll be easier if you come onboard, have a drink and I’ll put my shorts on.”

Soon we were sitting in the cockpit, a drink in hand, a bowl of peanuts between us and the conversation had moved on. They were in their mid 40’s, their 2 daughters had moved out to go to university, he was Welsh and she was originally from one of the Mediterranean islands (I can’t recall which one, sorry). She was very slim, a gym junkie, with a washboard flat tummy, very small breasts and toned muscles (not to everyone’s liking I’ll admit). They were on holiday with her mother and one of the daughters, sharing a small lodge just off the beach. The daughter had decided at the last minute to join them and it was a bit cramped, little privacy and thin walls, they heard every little noise and guessed the other 2 occupants did too. He had muttered that he would be glad to be home again for some “intimacy”, and said they had considered renting a hotel room for one night but using it for just a couple of hours. During this part of the conversation I’d looked carefully at her, her tiny bikini material was quite thin, it was obvious she had prominent nipples and the bumps around them could just about be made out. The bikini top was rather small, small enough that the edge of one nipple areola had escaped, she had well tanned dark Mediterranean skin and from what I saw her nipples would have been even darker. In the conversation she had said that she couldn’t sunbathe topless either.

I had discretely looked down at her bikini bottoms, she had a very clear camel toe and my guess was that it was clean shaven.  At the suggestion of renting a hotel room she had told him to be patient, it was only another week until they went home. Not long after that they said they needed to go, I’d enjoyed their company and more than enjoyed the view. I hadn’t realised at the time that we’d been talking and drinking for over 2 hours.

The following day I was down below, washing the lunch dishes and I heard a “Hello”, looking out I saw nobody, then a “We’re in the water, thought we’d swim out to say thank you for yesterday”. Again, I had nothing on, but invited them on for another cold drink. As she climbed the stern ladder I saw her bikini in a completely different manner, now wet it was virtually see through, I was right about her dark nipples and her pussy was definitely shaven smooth. I still hadn’t put my shorts on and she commented “You’re a bit more relaxed today” and nodded downwards. I casually but slowly donned my shorts, I have to admit that I’d enjoyed being naked in her presence.

We sat in the cockpit, the sun was out and it was tanning weather. She said “Look, I’ll come to the point, I can’t sunbathe topless with Mum around and it’s a shame to see this weather go to waste”, before she could continue I butted in “Of course I don’t mind.” And with that she reached behind herself, unclipped her top and removed it, revealing just as I’d imagined, two very pert tits, no sag, cute, tiny, very dark nipples with fairly small areola. I must have stared for a few seconds before looking back at her face.

The conversation went on and I started to feel that we were now friends, so cheekily enquired, “No more thoughts about renting a room? Because from what I can see I can understand his frustrations.” “Thought about it yes, doing it no, frivolous and out of the budget, but very frustrating.” I pondered for a moment and said “You came straight to the point earlier when you asked about going topless. I’ll come straight to the point with you. I feel I know you two well enough to make this offer. There’s a large bed in the bow, I’ll stay here in the cockpit to give you two some privacy, help yourself.” There was no time to discuss it, they both stood up and in a flash disappeared below.

After a few minutes I wondered how they were doing. From the cockpit and the right position, I can see through the saloon to the forepeak bed. They had both stripped off and I could see that she was on her back with his head buried between her thighs. I could hear tiny moans and saw her hips buck as he found the right spot, she was enjoying herself and he seemed to go on forever. I saw her push his head away and watched as they moved around, giving her mouth access to his cock. I carefully watched as she rolled back his foreskin and licked the end of his cock. I didn’t notice straight away that her eyes were open and she was looking directly at me. I’d been spotted and for a moment felt guilty, but she kept looking and a wink made it obvious that she didn’t mind. I watched as she looked directly at me and took the entire length of his cock in his mouth. After a moment or two, I saw him move her mouth away, pushed her hips around so that her arse was in my direction, he moved her legs apart and started to finger her pussy from underneath, he was finger deep and I’d got a ringside position. It was obvious that he also knew I was watching. There was nothing I hadn’t seen, her tits, her pussy, and now her cute arsehole.

Knowing that they knew I was watching, I moved down to the saloon for a better view, and what a view it was. He was now on his back with his head away from me, and she was sitting astride him, reverse cowgirling. She smiled at me and leaned back, that gave me a clear view of his cock sliding  in and out of her velvet smooth pussy (I had been right about it being shaven). I watched as they both tensed and realised the show was over, they’d simultaneously orgasmed. I stood up and passed them a box of tissues, “You’ll need these” I said. Laughing out loud “Thank you” he said.

A few moments later they came back to the saloon, he’d got his shorts on but she was still naked. “You’ve been a star” she said. Standing in front of me with her pussy more or less at my face height she said “He says that I need to say thank you, you can’t fuck me, but you can touch me if you wish.” With that she took my right hand, opened her legs and placed my fingers on her pussy lips. I started to rub her clit and with my other hand groped her tits, so small against what I was used to, they were firm and hard to get a handful, so I concentrated on her now very firm nipples. He watched as I finger fucked her moist pussy, she sat down beside him, almost falling over in the process. I was now in a position, kneeling in between her well splayed legs, able to get a very close up look as my fingers moved in and out of a beautiful pink pussy, one finger at first, then two with my thumb vigorously massaging her clitoris. I wondered, should I try to get three fingers in her, as she’d just been fucked I decided to try, it wasn’t easy but with a bit of gentle twisting and persuasion they went in. It was well received and it didn’t take her long to orgasm.

Afterwards she sat drinking coffee, still naked and me enjoying the view, commenting on her beautiful body. I slept well that night in the same bed they’d fucked in, dreaming about and still not believing it had happened.

I saw them just one more time the following day, I’d decided it was my day to depart anyway. They both thanked me with a bottle of whisky. Nothing happened, I think they’d relieved themselves for the time being, or at least until they arrived at home.

Published 
Written by Dougal_Too

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