When we were in our early 20s my girlfriend and I decided that it would be fun to go on a sailing holiday with some friends so we booked a holiday in Greece on a flotilla holiday. We had some sailing experience but did not feel fully confident so we arranged to have a yacht with a skipper.
The first few days were taken up learning the ropes with others who were to form the flotilla before we set off to explore the islands and little bays in the area. The general form was that we could explore during the day and would meet up in the evening usually at a small port where there were Tavernas we could try out so there was no need for anyone to cook a meal and we could have a few drinks.
During the day we would go off on our own exploring; sailing during the morning and swimming and sunbathing after lunch. In spite of the breeze it got very hot during the morning and by lunch time I was in just swimming trunks and both girls were in their bikinis. When it got really hot at mid day the only way to cool off was to go for a swim and afterwards the girls liked to sunbathe on the fore deck. My girlfriend was anxious to avoid tan lines so when she returned from her swim she would take off her bikini top and hang it to dry on the guard rail and then lie on her towel.
The skipper was a guy in his late 30s or early 40s and he remained in the cockpit reading while the girls were sunbathing so he could only see them when they were sitting up or standing although he no doubt noticed when my girlfriend took her top off before lying on her towel and would have had a brief glimpse of a small pair of firm milky white tits with neat pale brown nipples. She looked pretty good in a bikini and she knew it. She was five foot four inches tall, long legs, slim 34B 23 36 and had long fair hair usually in a pony tail. She looked even better in bikini knickers only!
As the week progressed her milky white tits lost the glaring white and began to take on the colour of the rest of her body, a light brown. I also noticed that where she previously always sat down before taking off her top she now took it off when standing up and always faced the stern of the boat so that he could see her. She obviously enjoyed teasing and flaunting her tits for him to see. About this time I also noticed that if she went for a second swim she would no longer put her top back on but would swim topless and would emerge from the sea over the stern, where he was sitting, with bare tits and pert erect nipples well within reach.
Sometimes the girls would continue to sunbathe while we were in transit leaving the men to do the sailing but it was often necessary to alter the sails which meant the girls would have to move and take care of the foresail, moving it from one side to the other. To start with it took them a little time to put their tops on before moving to adjust the ropes but now I noticed that although my friends girlfriend put her top on first, mine no longer bothered and she would move about the deck with bare tits which both my friend and I enjoyed and no doubt the skipper did too. She did I had to admit look particularly attractive wearing only a very small pair of bright blue bikini knickers, her hair in a pony tail!
Before the end of the first week she was spending most of the time on deck without her bikini top and her tits were almost the same colour as the rest of her body. The other girl still wore her top unless she was lying down, so Jan also wore her top to start with in the morning but once she went for a swim she no longer put it back on and spent the whole afternoon in just knickers with her tits in the sun. Eventually the other girl plucked up the courage to follow her example and did not put her top back on once it was wet unless she had to move to adjust the sails and eventually she decided that was too much bother too and so we had both girls acting as crew in only bikini knickers during the afternoon which was appreciated by all of us guys.
About the time that the other girl decided to go topless my girl friend decided that she didn't want a white bum either so after her swim (when she was invariably topless now) she would remove her knickers before she lay on the foredeck and sunbathe completely naked. She remained standing facing aft as before as she took off her top and then she took down her knickers giving us all, including the skipper, a very nice view of her standing completely naked, tits bare and neatly trimmed bush displayed before she lay down on her towel. She certainly seemed to be in no hurry to hide her nakedness and clearly enjoyed flaunting her body for us men to enjoy. The first afternoon of her sunbathing nude we only had to alter sail twice and I wondered what she would do when we had to but I needn't have worried because the just stood up and did what was needed completely naked! The top of her body was now quite tanned - including her previously white tits - and it contrasted with the white patch where her knickers had been as indeed did the neatly trimmed dark hair of her bush; trimmed so that it did not show around her knickers and enough so that the slit of her pussy could be seen too.
Sometimes if the weather was good we stayed in a bay overnight instead of being tied up to a jetty and we had a BBQ on the beach. We would stay at anchor overnight just checking once or twice during the night to make sure that the anchor was holding. On one of these nights when it was very hot I woke to find that my girlfriend was not beside me so I looked out of the hatch to see where she had gone. Hearing a murmuring I looked aft to the cockpit to see that she was talking to the skipper there. He was in just boxer shorts and she had slipped on a thin white cotton blouse: she had been sleeping nude.
I could not quite hear what they were saying but I could tell from the body language and the general tone that she was flirting with him and he with her. He obviously made some remark about her body as she laughed and then sat forward pushing out her chest, pulling apart the sides of her unbuttoned blouse baring her breasts and I could see her mouth form the words "do you like them?" From his reaction he clearly did, looking at them and then reaching out to run his fingers over one of them and over her now erect nipple. She did nothing to stop him so he moved a little nearer and cupped one tit in his hand to give it a squeeze and not being rebuffed he soon ran the palm of his hand over the other one too. All the while she sat still while he played with her tits looking down at his hand and into his face as he did so.
After a while he moved his hand down on to her thigh. She did not react initially but when his hand moved towards her pussy she obviously thought that was far enough and stood up. I could see now that she had not put any knickers on before going to talk with him as the blouse was quite short so her bare cheeks showed but also because she did not pull the front closed over her tits and I could see her bush and even the slit of her pussy. It was even better for him, he had a close up view! She said good night and started back in my direction smiling and holding the blouse closed over her bare breasts so I quickly slipped back into bed.
The following day there was no indication from either of them of their tete a tete the night before but I noticed that she now spent more time naked even when we were sailing and he clearly enjoyed the view. That evening I told her that I had seen her teasing the skipper the night before and she said - "Well, it must be lonely having no one especially when both of you lads have girls and it must be frustrating for him having two practically naked girls around him all day". I told her that I knew she enjoyed teasing but she should take care as looking might not be enough for him. "How do you mean?" she asked so I told her "he'll probably try to fuck you". "Yes he might but I might enjoy that" she said " I've never been fucked by an older man - would you mind if he did fuck me?". " I might be a bit jealous" I replied " but if you really wanted it and promised to tell me how it was for you afterwards I don't think I would really mind".
Over the next few days she continued to work on her tan - an all over tan - and we all enjoyed having a naked girl on board. She usually put her pants on when we all sat in the cockpit to have a drink or some lunch but not always and otherwise remained naked. Despite her example the other girl would not take her knickers off but she did now remain topless pretty much all day, even when we were sailing. She had a good pair of tits, (probably a C cup I thought) so this addition to our visual pleasure was much appreciated by all three guys aboard. Both girls looked very fetching when they came aboard after a swim with wet tits and hard nipples and the sun glinting in the hairs around my girlfriends pussy was a bonus.
The days were now counting down to the end of our holiday but the tan was looking great. We had not anchored off for some days, having meals ashore and tied up to a jetty overnight but on our way back to where we had started from we anchored in the same bay as before and decided to stay there overnight as the weather was settled, it had been a very hot day and was a warm sticky night.
I had a feeling my girlfriend might want to renew her acquaintance with the skipper so I feigned sleep until I felt her slip out of bed and look out of the hatch. He was obviously not there as she slipped back beside me and lay there for a while before she heard some movement when she looked out again. This time he must have been there as she slipped her thin white blouse around her shoulders and got out of the hatch. As she did so I saw just how thin the blouse was as the outline of her breast and pert nipple was clearly visible against the moonlight. I knew it was thin enough for her nipples to show through during daylight and always enjoyed it when she wore it when we went ashore as I guess did a lot of other guys there. She did not do it up but just held it loosely across body her as she moved down to the stern.
He was sitting there in boxers again and was obviously glad to see her. As she chatted to him she let the front of the blouse fall open so both breasts were partly exposed but the nipples remained hidden - just. He said something to her that made her smile - probably remarking on what nice brown tits she had - and she once again opened the front wide so he could see them. Suddenly she slid over beside him and I saw her put her hand on the front of his boxers saying something that made him smile. My guess is that she asked what the bulge in his boxers was and he said "what do you think?". She squeezed it several times and I could see that he certainly had an erection now and he reached over to put his hand inside her blouse to feel her bare tits which she obviously liked as she made no attempt to stop him.
As he played with her tits under her blouse she reached inside the top of his boxers and took out a very erect circumcised cock. He looked down at her small hand wrapped round it and said something to her which made her smile and she started to run her hand up and down along its length. He clearly liked this and kept his hand inside her blouse while she pulled his cock. He pulled her blouse open again so he could see her tits and from time to time I could see him giving her nipples a tweak and from her reaction he could no doubt tell that she liked having her nipples played with.
After she had been stroking his cock for ten minutes or so he told her to stand up as he pushed the blouse off her shoulders so that as she stood up the blouse slid down her back and when she released his cock for a moment it fell to the floor and she stood naked in front of him before taking his cock in her hand again and continuing to play with it. I could now see that she had not put any knickers on before going to meet him and had obviously taken off those she wore on going to bed as she stood completely naked as he stroked the inside of her thigh right up to her pussy.
Soon he began to stroke around her pussy as well as up and down her thigh and this time she didn't move away. She stood with her legs apart just enough so that he could reach her pussy and part her pussy lips to find her clit. Now it was her turn to stand transfixed as he rubbed her clit with the end of his finger but she still managed to stroke his cock and it was soon obvious that both of them were in a fairly advanced state of arousal. After he had played with her clit for a while, she stood still while he slipped his fingers up her cunt. He then pulled her down beside him where she sat with her legs apart and he continued to slip his fingers into her cunt as far as they could go and to play with her clit for another five minutes or so while he stroked round her nipples and I could see she was fully aroused and definitely wanted him to fuck her now. He too obviously recognised the signs and he pressed her back on to the seat and she willingly lay back as she guided his cock towards her wet cunt until the end of his cock pressed her lips apart and he slipped the head of it into her.
I saw her head go back in ecstasy as he pressed it deeper into her and his cock filled her obviously wet cunt. He slid gently into her several times before speeding up when he realised, as I did, that she was going to reach orgasm very quickly. She gave a little moan as he thrust into her and from the urgency of his thrusts I could see that it would not be long before he filled her with his spunk. I did wonder if he would pull out at the last minute and squirt it over her naked body instead of into her but as her hips thrust out towards him as her orgasm began to rack her body he thrust quickly into her and then froze as he emptied his balls deep inside her. Her cunt was now so wet that his cock was no longer a tight fit in her and as his cock went soft as he thrust weakly into her for the last few times I could see his cum leaking out and running down the inside of her thigh.
When he had finished and pulled his cock out of her she lay there for a little while as her orgasm subsided, her nipples still hard with excitement and his spunk oozing out of her pussy. As she stood up a load more of his cum poured out of her pussy and down her leg. She had nothing to staunch the flow as she had worn no knickers when she went to meet him until he grabbed a box of tissues and gave them to her. She mopped herself up as best she could and then giving him a quick kiss she set off back to where I was, still stark naked until he reminded her that she had worn a blouse but even then she didn't put it on and simply carried it back still naked and mopping herself again until she eventually slipped back in beside me still full of his cum but with a bunch of tissues stemming the flow.
When I woke up in the morning she was wearing black knickers which she had not been wearing when we went to bed so I asked her why she had put them on as she had been wearing the white ones she usually wore unless she slept naked. She told me she had got up in the night and had fucked the skipper perhaps thinking I would think she was joking and was surprised when I told her that I already knew and had watched as he first got her aroused and then fucked her. "You don't mind do you?" she asked and I told her that I did not mind as I had seen how much she had enjoyed it and incidentally I had also enjoyed watching him screw her and give her what she had obviously been asking for. She had been asking for it for days and the others must have noticed it too and would not be at all surprised that he had fucked her. She said that she really fancied him, she had really enjoyed it even if he was practically old enough to be her father. It was very exciting to be fucked by an older man; she felt she had been well and truly fucked and he was obviously a very experienced lover who knew just what to do to her to give her the most pleasure. If there had been time she would have liked him to do it to her again and give her multiple orgasms. She said she wondered if he fucked every crew member he met to which I replied that he probably did if every female crew member spent her time like she had, stark naked and obviously asking for it. It was the perks of the job!
After her adventure she spent the last couple of days naked still and even when we sailed into port for the last time she was only wearing bikini knickers and was flaunting her nice brown tits. She only put her top on as we left the boat after giving the skipper a kiss and saying " thanks for everything" - which I thought she said with real feeling!