Our Sailing Holiday in Thailand

Seven years ago, I had been successful in securing a huge contract for our software company supplying our product to a government department. It was massive for the company and personally a great financial bonus.

It has been a lot of hard work and long hours to make it happen, and my wife, Vee and I agreed to celebrate by taking a vacation.

Some friends of friends had told us about a sailing holiday they had in Thailand, and we agreed this was a perfect escape.

After researching the company and looking at the different reviews from former charterers, we contacted the charter company located in Phuket and hired a 38′ sailing catamaran for ten nights.

Amongst other options the company offered a provisioning and reprovisioning service instead of us having to supply our own food and drinks. We opted for the provisioning option but declined the reprovisioning that would take place halfway through the charter, because we didn’t want to have to be somewhere at any particular time. We also thought that we would be eating ashore at restaurants on a regular basis.

Another option offered was to have a crew member along to help with the sailing and to do the cooking and cleaning aboard the boat. Vee and I are both experienced sailors, so we didn’t need help with that, and I thought that another person onboard would cramp our style, however, Vee liked the idea of someone else doing the cooking. We decided to accept this option too but based on the idea that if it did become uncomfortable with another person onboard, we could drop them off somewhere. Some of the reviews we had read mentioned that the additional crew persons were either one of a brother and sister team, attached to the charter company. The reviews for both were very complementary of their skills and cooking ability, but you couldn’t pick which one you wanted, it was a case of who was available at the time. One review mentioned that the brother gave massages and Vee was hoping that we would get him.

We were in the business class lounge of Sydney Airport waiting to board our flight when we received a phone call from the charter company. The brother and sister had had a death in the family and had to return to their family village as a mark of respect. The charter company said however, that the siblings had recommended a cousin of theirs who was an excellent cook, but the company said the downside was that she didn’t have any sailing experience.

We told the company that was fine because we both had lots of sailing experience and it was arranged that the cousin, whose name was Mai would join us on our cruise. “Don’t worry” I told Vee, “I’ll give you plenty of massages, and it’s not like there is any shortage of massage parlours ashore in Thailand.”

We flew to Bangkok (11 hours), stayed overnight in an airport hotel before flying to Phuket the next morning. We took a cab to the marina and saw our vessel for the first time. It was in very good shape (for a charter boat), and we thought we would be very comfortable.

We went through a two-hour briefing about the boat and the navigational limits to our charter (we weren’t allowed to sail it back to Australia), signed our lives away and made ourselves comfortable onboard. We had supplied the charter company with a list of dishes we liked to eat as well as what we wanted to drink. Beer and wine for me, champagne and wine for Vee, and we thought that some gin and tonics would go down nicely in the tropics. We also noticed that there were several bottles of different liqueurs and spirits that had been left aboard by previous charterers.

We were looking forward to meeting our new shipmate, Mai for the first time but when she arrived it was much better than expected. Mai is a beautiful young woman, 22 years old, 5’7, which is tall for a Thai girl, with a wonderful figure and lovely face. She spoke very good English but seemed fairly shy. Mai was dressed in a Chut Thai the traditional long Thai dress and we were hoping that she had more appropriate sailing clothing. Vee saw me checking her out and said, “Steady old man, you’re old enough to be her father.” This was going to be Mai’s first time aboard a boat though, and we were hoping that she wouldn’t succumb to seasickness.

We motored out from the marina and headed out towards Phang Nga Bay with our biggest problem being avoiding the fishing nets that the locals had set across the channel.

Once out in the bay we had a bit of a play with the sails to check on them before anchoring in a little bay off a small island. We were the only boat in the bay, and it was extremely relaxing, exactly what we were looking for.

Vee and I were sitting on the trampoline mat between the two hulls at the bow of the boat when Mai bought out a bottle of champagne which was a gift from the charter company, along with two glasses. We told Mai that she was part of the team and said for her to bring out another glass. Mai had never had champagne before, and we all laughed when the bubbles seemed to get up her nose. We finished that first bottle, and Mai went and made us all a refreshing but strong cocktail. We were all feeling the effects of the drinks but especially Mai who obviously wasn’t used to drinking. Despite this, Mai was indeed an excellent cook and made a delicious meal with chicken and mango which we all enjoyed while sitting on the trampoline mat.

Mail declined to have anything else to drink but not so Vee who had a couple of G&T’s and was feeling very mellow.

I started massaging Vee’s shoulders and neck and she let out a satisfied moan. Mai asked her whether she would like a massage and Vee said she would love one. Mai went into the main cabin and a few minutes later she came out dressed more comfortably in shorts and T shirt and carrying a towel and massage oil.

Vee, who had been wearing shorts and a bikini top, stripped off and lay down on her stomach on the towel which had been placed across the trampoline mat. Mai started massaging Vee’s back and after a few minutes moved down to her legs. As I’ve explained in previous stories, Vee is an extremely attractive, former model who at the age of 40 still had a killer body. Watching her lay there in the open air with her beautiful butt exposed, being massaged by another beautiful young lady was very erotic.

As Mai was massaging Vee’s right leg, I got some massage oil and started on her left leg, copying what Mai was doing. We eventually moved up to her butt and while Mai did one cheek, I did the other. Mai looked over at me and smiled.

Vee was told to turn over, exposing her firm tits and bald pussy. Mai started massaging one hand and arm while I did the other, before moving down to her feet. As we moved up her legs, I kept seeing Mai take furtive looks at Vee’s pussy. We got to the stage where we were both massaging her upper thigh, so Vee had to bring her knees up and slightly spread her legs as both Mai’s and my hands massaged very close to her pussy. I looked over at Mai who seemed fascinated by the smooth, bald pussy and I also noticed that her nipples were standing out against her T shirt. I wondered to myself whether she was aroused because I certainly was.

We started massaging Vee’s stomach, moving down with light strokes under her belly button. As my hand moved lower, Vee’s pelvis responded by arching up slightly. Mai was massaging Vee’s stomach and sides, but I went further up and rubbed Vee’s right breast and nipple. Vee has very sensitive nipples and she gave a moan and once again her pelvis arched up. I looked across and saw Mai watching and she licked her lips with the tip of her tongue.

I motioned to Mai to massage the other breast if she wanted, and she quickly took up the offer and started rubbing Vee’s left breast and then copied me as I pinched Vee’s nipple. Vee was really enjoying this, so I asked her if she would like a “happy ending.”

When I said this, Mai quickly looked up at me and smiled, she had obviously heard the saying before. Vee on the other hand said, “Don’t start something you can’t finish.” but I thought, what the hell, nothing ventured nothing gained, so I moved down, spread her legs and started licking her pussy.

Vee was already wet and as my tongue initially touched her clit, she let out a load moan. I looked up and saw Mai watching me with fascination on her face. Mai started massaging both of Vee’s tits, pinching and squeezing her nipples. Vee reached up and put her hand behind Mai’s head and pulled her down for a kiss. Mai responded and soon their tongues were entwined.

After a couple of minutes of having her pussy licked, Vee has a massive orgasm with her whole body convulsing. Mai looked fascinated, almost like she had never seen someone have an orgasm before.

Once Vee had recovered, she grabbed the waistband of my boardshorts, undid them and pulled them down revealing my swollen cock. She put it into her mouth and started giving me her best head. Mai was watching on and Vee asked her if she would like to join in. Mai put my cock in her mouth and her head bobbed up and down, but she obviously wasn’t all that experienced. Vee started to show her some of the things that I liked including licking around the sensitive rim of the head and sucking my balls. It was like she was mentoring the younger woman. It was wonderful sitting there on deck, looking out at a beautiful vista and having two lovely women sucking my cock.

While this was happening, Vee removed Mai’s T shirt, bra, shorts and panties and we had our first look at this lovely body. Beautiful coffee skin in all the right places, small but perfectly shaped breasts with hard nipples, tiny waist and thin hips and a thick bush of pubic hair.

After a few minutes, Vee crouched over me and lowered herself onto my cock. I pulled Mai down for a kiss and she responded and thrust her tongue into my mouth. I then positioned her so that she was sitting on my face, and I start to lick her clit. It was like she had received an electric shock and we later found out that she had never had her pussy licked before.

Mai was facing away from Vee who was still moving up and down on my cock, and both Vee and I were playing with Mai’s tits.

To my dismay, Vee got off my cock and came around and started to suck on Mai’s nipples. We lay Mai on the trampoline mat, and I spread her legs and continued to lick her clit. After no more than two minutes she absolutely erupted in an intense orgasm, thrashing around looking a bit perplexed and even scared. When the pleasure had subsided, we asked her if she was ok, she nodded that she was, but it took a couple of minutes before she could explain that something like that had never happened before.

Mai explained that she wasn’t a virgin, she had had three boyfriends over the years, but none had licked her down there, and it seemed like she had never had an orgasm before. I have to say that I was feeling pretty chuffed at this point. Vee asked her if she would like to have sex with me, but Mai looked a bit scared, pointed to my cock and said it was too big.

Vee told Mai that she could try and if it hurt too much, we would stop, and Mai nodded yes.

We lay Mai down on the mat, put her legs on my shoulders and I entered her very slowly. She was so tight, but after putting just the head of my cock in, I started easing in and out and gradually putting more and more in. When I had most of my cock in her pussy I stopped, and we asked her if she was okay. Mai nodded yes. I started working in and out a bit faster while Vee kissed Mai and then started rubbing her clit with her fingers.

After just a few minutes, Mai erupted in orgasm again and during the throws of her orgasm her pelvis and hips were thrusting and moving uncontrollably. I started thrusting faster and faster into her tight pussy getting close to my own release, when Vee said, “Don’t cum in her, it might freak her out.”

Reluctantly, I slowed down, but Vee got up on her knees with her beautiful ass facing me and said that she needed to be fucked. I drew out of Mai and got behind Vee, grabbed her hips, thrust into her, and started pounding away as hard as I could.

Mai was still lying there recovering and watching us in awe. A few minutes later, I knew from experience that Vee was getting close, so I put the tip of my index finger into her ass which is something she loves. She climaxed and while she was enjoying that, she bent down and kissed Mai. Seeing this set me off, and I released into Vee.

We all lay there naked, I had a woman on each side, with my arms under their necks cushioning their heads. We kissed often as we chatted to Mai about her previous experiences.

Vee was playing with my cock as we just lay there relaxing. Mai asked why we didn’t have any pubic hair as she had never seen this before, and Vee explained that we liked to have it bare and had it waxed off.

Vee also explained to Mai that she loved men but also loved to kiss and caress other women because their bodies were so soft, smooth, and beautiful. Vee said that she sometimes licked other women too and asked Mai whether she would like Vee to lick her.

Mai nodded yes. Vee got between her legs and started licking with Mai closing her eyes and going into bliss. It looked wonderful with the sunset in the background, so I went inside, got my camera, and took some shots for our holiday album. I knelt beside Mai’s head, and she took my cock into her mouth and started sucking. Both of us were getting close to cumming, so I took my dick out of her mouth and started stroking it, aiming at Mai’s tits. As she came again, I shot all over her tits.

The next morning, I got up and made the coffee (we had made sure there was a coffee machine onboard). When Mai came out of her cabin, I bent down and gave her a good morning kiss which she returned.

Mai made us some breakfast and we decided to get sailing. Vee was just wearing a bikini bottom with no top, and later we could not help to notice that Mai had removed her T shirt and was just wearing shorts.

We spent most of the day sailing through the bay before anchoring in another secluded bay. I was hoping for some more fun, but three fishing boats came and anchored nearby, and the men onboard looked very rough. The ladies got dressed and mostly kept inside for the evening.

We had a lovely meal thanks to Mai again and then turned in early. Apart from a bit of touching and kissing nothing of a sexual nature had happened during the day.

I was awoken at around 3am by the wonderful feeling of someone sucking my cock. I could feel Vee beside me, so looked down and in the moonlight, I could see Mai testing out her new skills.

I nudged Vee (who doesn’t like to be woken) and nodded towards the foot of the bed where she saw what Mai was doing. “We’ve created a monster,” was all she said before going back to sleep again.

Mai kept sucking until I came, taking most of the load in her mouth and swallowed. She then just got off out bed and went back to her own.

In the morning when I was making coffee again, Mai came out just wearing panties and I gave her a big kiss, clutched the cheeks of her butt in my hands and squeezed. I rubbed her pussy through her panties, and she was very wet.

When I had finished making the first coffee, I gave it to Mai and asked her to take it to Vee. When I got into our cabin with my coffee, the two women were entwined.

Now there are some things (I discovered that day) even more important than the first coffee of the day, this was one of those.

I got between Mai’s legs and started licking her pussy again, returning the favour from the night before. Soon Mai had another enormous orgasm.

We were in clear, clean water so we decided to go for a swim, but we soon found out that Mai didn’t own any swimwear (not that she needed any). Vee decided that a shopping trip was necessary to get Mai some bikinis.

We headed across the bay to the city of Krabi and anchored off the Sheraton Hotel there. We’d been told that the Sheraton was often welcoming to visiting yachts, especially if they didn’t have high occupancy.

As we took our dinghy towards the shore, two men in Sheraton shirts walked down to the beach, met us, helped us pull the dinghy up the beach somewhat, and then let us know that we were most welcome. They showed us the pool area and said we could use it, as well as the bar and restaurants.

My plan was to relax with a book while Vee and Mai took a taxi into town to go shopping for bikinis.

I did some laps in the pool, read for a while, and eventually found myself in the jacuzzi. I was joined by an English couple, Jessica and Gavin. Both were attractive in their mid-30’s and in Krabi on a two-week holiday. Jessica asked what I was doing, and I explained that we had hired the catamaran and were sailing around visiting different places.

She said that it sounded wonderful and wished that they could do something like that. She kept on taking shots at Gavin saying that he should have learnt to sail, he should have thought of hiring a boat, he should do this or do that and generally running him down. For his part, Gavin just sat there saying very little and when he did, she chastised him.

I decided that I didn’t like her very much, but at one point her leg moved over and rested against mine. I moved my leg over to apply more pressure and she responded. She then put her hand on my thigh.

As I say, she was very attractive, but I didn’t really like her, so I thought “what the fuck” and moved my hand down the back of her bikini bottoms, lifted her ass slightly and stuck my middle finger into her pussy.

She looked at me, bit her lower lip and then smiled.

She sighed and said, “That feels so good.”

“Gavin,” she said, “Steve has his finger in my pussy.”

I didn’t know how Gavin would react, but I thought that I could take him with my spare hand, if necessary, but he just looked at us both and nodded.

I thought to myself that this was one of those cuckold situations that I had read about but never experienced before.

I looked at Gavin and said “Okay, lets go to your room so I can fuck your wife.” He just got up to lead the way.

When we got to their room, which was a ground floor villa, I told Gavin to undress his wife for me. He pulled down her bikini bottom and then unclipped the top. I then told him to take off my boardshorts.

He came over and reached for the clasp at the front, but I told him to kneel to take them off. When he lowered my boardshorts, my cock sprang free and almost hit him in the face.

I told Jessica that we were going to have a shower, and once we got into the cubicle, I pushed her shoulders down so she was kneeling and fed her my dick. I thought that I would cuckold both of them.

I eventually stopped her, and we moved onto the bed. I had Jessica lie down on the bed, put her legs on my shoulders and told Gavin to come over. I told him to take my dick and rub it along his wife’s pussy lips.

I’d been in the army (a very homophobic organisation) for 12 years, and this was the first time that I had ever let another man touch my cock. Gavin rubbed my cock up and down his wife’s wet pussy lips until I told him to put it into her.

I started fucking her hard and she was loving it. She kept on yelling “fuck me, fuck me harder” and then saying to Gavin “now that’s a real cock” and continued to belittle him.

I didn’t like the way she treated him, so I told her to shut up.

After a few minutes, I turned her over and pulled her hips up, so she was kneeling.

“Oh, yes, yes fuck me doggy” she said, so I told Gavin to come over and put my dick into his wife again.

I pounded her, not really caring about her pleasure, although she did seem to be enjoying it.

I told Gavin to come over and lick her asshole. “Get it nice and wet and ready for me Gavin” I said.

“Did you hear that Gavin” she said, “he’s going to fuck my ass in front of you.”