Once we got up and going, we grabbed a quick breakfast and decided to meet up with Mike and John at the spa. The spa area at the resort, like most, was split between the men’s area and the women’s area. You walked into the respective locker room, which included the steam room and sauna, but you went out a back door of the locker room for the Jacuzzis, which were coed.

Ann and I decided that we’d start there, so we both went through our respective locker rooms and met back out at the Jacuzzi. As it would happen, Mike and John were relaxing in some lounge chairs in that room and we all exchanged hellos. The guys seemed a little tentative or nervous.

John spoke up and said, “I hope no one has regrets about last night, we don’t want to cause any problems between you two.”

Ann walked over and gave both him and Mike a hug and told them, “Last night was the first time we’ve ever done anything like that, but it was fantastic.” She then thanked both of them.

We spent some time relaxing, both in the Jacuzzi, and in the lounge chairs before John mentioned wanting to go spend some time in the sauna. He asked if anyone else wanted to come along and I said, “I think I’ll stay here and spend more time with Ann.”

He replied, “When I was in the locker room earlier, there was no one else in there, so I can double check, but I don’t think it would be a problem to sneak Ann in with us, since the sauna is right by the back door.”

Ann said that sounded nice, so we all went back into our locker rooms to take off our swimsuits and get towels. There didn’t appear to be anyone in the men’s locker room, but John and Mike went to double check the sauna while I went back out to meet Ann.

When the guys came back out Mike said, “There actually are two guys in the sauna, but we explained the situation that we were a mixed group and wanted to spend time together to see if they would be alright with us joining them and they are fine with it as long as Ann isn’t easily offended because they didn’t want to have to worry about covering up.”

With that we all headed into the men’s sauna. The two guys (Bob and Rich) in the sauna were friends and appeared to be in their sixties. They didn’t seem shy and didn’t cover up or anything, just said hi and smiled. Since they were sitting on the left, we all sat across from them, with Ann sitting between Mike and I, and John sitting on the other side of Mike.

As expected Ann had everyone’s attention as she loosened her towel and let it fall on to the bench as she sat down and settled in. It occurred to me that despite her sunbathing in just a thong bottom, prior to this trip, I was the only guy to see her pussy other than doctors, etc, but now there were four more men that had seen her most private of areas. We settled in and just made small talk getting to know each other a little better. Bob and Rich just relaxed and listened in on our conversation.

It didn’t take long until Mike’s hand found itself resting on Ann’s thigh. She didn’t seem put off, so I didn’t care, in fact I was liking how my wife was acting on this vacation and decided that I would encourage her to let loose. Well as you might expect, Mike’s hand didn’t stay put and kept inching higher and higher, closer to Ann’s cunt. She kept spreading her legs wider until Mike was fucking her with his fingers and playing with her clit. The rest of us were enjoying the show and it didn’t take too long before she was moaning loud and breathing hard as she came.

I noticed that everyone was as hard as a rock, so when she calmed down I told Ann, “That’s not right, you’ve gone ahead and made Bob and Rich hard, and you’re not doing anything about it.”

She smiled at me and asked, “What would you like me to do for them?”

I told her that she should at least ask them if they’d like a blowjob, which she did and of course they said yes. Ann crossed the room and Bob and Rich were sitting on the upper bench, so she knelt between them and took both of their hard cocks into her hands and started stroking up and down. They both looked like they couldn’t believe their luck as she took turns licking up and down their shafts.

After a few minutes of licking and teasing she engulfed Bob’s prick and really started going at it, then did the same to Rich as she continued to stroke Bob. This went on for a little while and Mike, John, and I watched. Bob and Rich each reached down and took a tit in their hand, pinching and pulling on Ann’s nipples. It didn’t take long and we could tell that the guys were close to coming. She was sucking Bob as he started coming and she didn’t miss a drop, but Rich came at about the same moment as she was stroking him and came on her side, including her left breast. Once she was done with Bob she looked Rich straight in the eyes, scooped up some of his cum off her breast and licked it off her fingers. The way she did it was so hot I think he almost came all over again.

Bob and Rich thanked Ann and told her she was amazing, and with that they headed out, as they said their wives would be waiting for them back at the pool. Ann then looked at the three of us and smiled, saying that she hoped we liked watching, which we all assured her we did.

With that we decided it was time to head out, as it was only about an hour before lunch time and Ann wanted to get some beach time. John mentioned that they had seen that the resort offered a two-hour trip on a sail boat, and they would like to treat us to come along with them that afternoon for a trip. It sounded good as basically the sail boat had decent size deck where we could lay out and enjoy the scenery as the crew of two would sail along the coast and around some small offshore islands. We agreed and they went off to arrange it while we headed down to the beach.

A couple of hours later we were at the dock boarding the sail boat. It was a quiet day, so it was just the four of us, another couple (Dave and Susan), and two crew, who Ann noticed because they had nice bodies, which I teased her about.

She admitted that she thought they were hot and she was just looking.

I responded, “With what’s happened on this trip, are you sure you were just looking?” She noticed that I was smiling as I spoke, so she just gave me a sly smiled and boarded the boat.

Once we were under way we were give a rum punch that was pretty strong, but the sweetness masked the alcohol. Everyone was getting along well and Ann was laying down a towel to sunbathe on and asked the crew if it was okay if she went topless (like they’d really say no) and they told us that was fine and that some of the guests on the sails even went completely nude since we were not really visible from the shore.

I smiled and asked, “Well, what does everyone think of that?”

We all agreed that we’d like to try it. Susan seemed hesitant, but eventually said that it sounded fun since we had a small group. So off came the clothes and we all laid out. I had just closed my eyes and I heard one of the crew coming to refill our drinks, I heard Ann gasp slightly, so I opened my eyes and was surprised to see Jake (the crew member) was nude as well and he had a huge black dick swaying back and forth as he moved around. Susan looked shocked and Ann was mesmerized by the large organ. When he had finished with the drinks and left, Ann just looked at me and said, “Wow!!”

Not wanting to get burned, Ann asked for the sunscreen and then looked at me and John, who was on the other side of her, and asked if we’d help her with the sunscreen. John jumped at the chance and he started rubbing it into her chest and arms.

I noticed Jake nearby and asked him if he’d be kind enough to put sunscreen on Ann’s legs as I really just wanted to relax. He of course agreed and Ann smiled and stared at his huge cock as he walked toward her. So John started rubbing the lotion into Ann’s chest making sure to get plenty on her breasts, and Jake came over and started by rubbing lotion into her hips, moving down the outside of her thighs to her knees. Then he moved to her inside thighs and moved right up, not even hesitating before he was massaging her pussy lips. Ann immediately gasped and watched as he continued to caress her most intimate of places. Meanwhile, John became focused completely on Ann’s nipples, pinching, pulling, and even leaning over to suck and bite them.

Ann reached over and started stroking John’s hard cock and started moaning as Jake started working his fingers into her wet cunt. Susan was watching all this happening and Dave had reached around her and was fingering her while she was playing with her nipples, obviously very turned on.

Once Ann was really worked up, she got up on her hands and knees and starting sucking Jake’s cock. Now fully erect his cock was at least ten inches, probably longer, and thick as well. Ann was having trouble sucking it due to the size. While this was going on, John moved in behind her and slid his dick into her.

Meanwhile Susan and Dave had started fucking and Mike was watching them and jerking off right in front of Susan. Before too long, John announced, “I’m cumming!!”

Dave was not far behind him and Susan was cumming as well. I couldn’t help myself, so I took John’s place and slid right into my wife’s sloppy cunt.

She came as I pounded her for all I was worth and she never stopped stroking and sucking Jake. After I came inside her, Jake needed a release as well, so he laid her on her back and spreading her legs wide, lined up his mammoth tool with her slit. I was mesmerized, and a little nervous, as I watch the huge mushroom head spreading Ann’s cunt further than it had ever been before.

Prior to this vacation I was the only one she had ever been with, so I know that she was experiencing something entirely new with Jake. He eased it in an inch at a time, until he was about seven inches in, then he pulled out and in one forceful move buried his entire length into my wife. She screamed with pleasure as everyone else just watched.

I couldn’t believe what I was seeing as lust had just completely taken over Ann. She screamed that she was coming, and I think that Susan came just at seeing and hearing what was happening. On her second orgasm from Jake he had finally had enough and groaned as he started coming too. Once he started going soft, he pulled out and cum was just pouring out of Ann’s well used cunt.

Mike hadn’t yet gotten off, so he took Jake’s place as Jake lay down next to Ann, which allowed her to reach over and play with his cock. Amazingly, in just a few minutes he was hard again and once Mike came inside her, she got up and impaled herself on Jake’s once again hard cock. She told him, “Your dick is absolutely amazing.” As she was riding him, he mauled her tits with his hands and mouth until they both had earth shattering orgasms.

Jake got up and went back to his tasks around the boat while the rest of us were just in awe. Mike and John told me how lucky they were to have met us this trip and Susan and Dave complimented Ann on how hot the show was. Ann for her part didn’t really say much and just seemed tired and relaxed. Once the sail was over and we were disembarking, Jake, came over and put an arm around Ann and said, “You should bring your hot ass back on this trip tomorrow.” Then he shook my hand and told me how lucky I was and we left.

When we got back to our room, Ann apologized to me for acting like a complete slut the way she did. I told her it was a great time and that I was so turned on, that my hard-on may never go away. She said that she really shouldn’t have done that and she was sorry, so I asked if she enjoyed fucking Jake, which she bashfully admitted she did, so I told her that was fine and it was fun for all. I also told her we could go back on the sail again while we are here, which got a smile from her. Then I said, “We should really get cleaned up, we planned to meet Mike and John for dinner before we go to a night club with them and I think even Susan and Dave are joining us.”

She said, “ Knowing Mike and John, they’ll probably have some plan for the evening.”

I replied, “That sounds like fun.”