An Anniversary Trip to Remember

My wife was reading this forum and suggested that I post our story here, so here it goes.

My wife and I were coming up on our fifth wedding anniversary and she suggested that we take a trip with just the two of us. We are both on our second marriage and we both have a child from our previous marriage. We normally travel with them, so it was a little of an unusual request for her but it also made sense being that it was our 5 year anniversary. Our children are older so letting them stay with their respective other parent was an easy solution to being able to travel alone. When we travel I usually go along for the ride, meaning my wife does most of the planning. That isn't to say I am a pacifist in the relationship, I am just fine to defer travel planning to her and I trust her opinions on what we will both enjoy. She told me she found a resort in Mexico that was adults only and geared toward "the sexually liberated."

I asked what that meant and she explained that based on what she read it wasn't like one of the famous Jamaican sex resorts, but that it was adults only and that the people that go tend to be uninhibited, there are very few rules including clothing optional, and from what she read people go there to have fun. I was a little confused and asked what she had hoped to get out of it. We have a good marriage and I thought we were both very happy and satisfied (an opinion my wife later strongly affirmed on her end too), so I wasn't sure what she was suggesting this for. I was kind of thrown off a little bit and also nervous about agreeing since I didn't know what to expect. She just said she didn't know and wasn't sure herself, but that she thought it might be fun to try. I asked her what trying meant, and she just said going there and experiencing the environment. I asked what I should prepare myself for, meaning did she have any possible outcomes in mind. I think I was probably sounding insecure, so I stopped the line of questions.

Later that night we were having a glass of wine after dinner and my wife said that if I was uncomfortable we would do something else. I said I didn't know whether to be comfortable or uncomfortable because she wasn't explaining what she was hoping to do on this trip. She then said that she thought it might be fun to try going topless in public. She then asked if I would be okay with that. I thought about it and reasoned that we would be around people that we would never see again, and I thought it might be kind of erotic and maybe stimulating to see my wife naked in front of other people. I asked if she would have any expectations of me, and said I didn't want to be nude in public. Not that I am miniscule or anything but I definitely don't meet the threshold for public nudity.

So we agreed to go. As the date neared I was looking forward but also getting nervous. I think I was feeling insecure more than anything. My dick isn't embarrassingly small when it is hard, maybe kind of a small average, but when it's soft it can go from okay to something that I definitely wouldn't want anyone seeing. And I was getting worried that she would try to get me to go nude. I reinforced to her that I didn't want to do that and she said she was completely fine with that. On the plane we talked about rules, what we would and wouldn't do. And as the flight went on, and we had more airplane bottles, we got more and more relaxed with the rules. It became a 5 hour foreplay session.

When we got to the hotel the vibe was very casual and easy going. I noticed that the resort staff were themselves dressed in a sexy way, which created a vibe. As we walked in I looked out to the left where there was a pool and I could see that a lot of people were naked. I couldn't see well due to where the sun was (in my face) but I could make out the general outline.

It was getting late in the day - maybe a half an hour before sunset, but it was still very hot out so my wife suggested that we go down to the pool and hang out at the pool bar for a while. We got ourselves set up in our room and headed down. The regular bar was packed but the swim up bar had a few open seats so we went in the water and went over to it. When we sat down, I noticed that the area that the bartenders made the drinks was up a few steps, and they would drop down a few steps to bring you your drink. I got to thinking about what a strange setup it was, and then I realized that it was designed to put the bartender's asses at your eye level, and I also noticed it was a very attractive bartending team. Both the women and the men. I definitely didn't object to the view, and before we knew it we were a few drinks in. There must have been a shift change or something since the people that were around the bar were slowly disappearing and there was a new group coming in.

There were 5 bartenders in the swim up bar. Earlier there were four women and one man, and all but one of them was attractive (one of the women was a little bit too overweight to be my type, although she had a nice face). The new shift reversed the ratio and now we had 4 men and one woman, with another woman coming in and out bringing supplies. The outfits for the women were very tight fitting but sheer cotton (or some similar fabrik) dresses, and the men wore tight fitting knee length white shorts and fitted polos. On a few of the men I could see that they were large and the outline of their cocks was pretty visible, and I was feeling a little uncomfortable at first. Maybe embarrassed is a better word. I kind of looked over at my wife to see if she was noticing and I saw her glance at the guy standing in front of us shaking a drink a few times.

He came down and poured my wife's drink and he asked where we were from (outside of Chicago) He said wow, I'm from Detroit. Over the next hour or so we had a conversation about how much the northern midwest had changed, and he seemed comforted by having a sense of home. My wife is in her late thirties and I am in my early forties, and I would estimate that the bartender is in his early or mid thirties. I say this because my wife asked me how old I thought he was, and I asked her why. She said she was just curious, but I thought there might be more to it. She was getting more and more flirtatious with him and became less polite about hiding her glances from me (but she was also getting more tipsy and I think she felt liberated by our conversation on the plane). And I will admit that as this went on, I started being turned on by what I was seeing and I was kind of reachin acceptance with the thought that something would happen.

It was late and we wound up going upstairs, but my wife was hot and bothered and we fooled around for a while. As I was using my hand on her I asked her if she liked Darren (the bartender) and she asked if it was okay if she said yes. And I just said it is not only okay, I want you to give me the first unfiltered thing that comes to your mind. She said yes. I asked what she liked about him and she said he had a very nice butt and legs. I asked what else, and she said that it looked like his zipper was having to work hard to stay closed with the pressure he was putting on it. We talked like that for a while longer and she had a very good orgasm. So did I.

The next day we got up early (we actually went to bed pretty early all things considered) and did a bunch of things around the resort. We went down to the beach for a while and there were lots of naked people, both men and women. My wife finally got to take her top off and I found that very arousing. It was sexy seeing her be unencumbered and openly sexual. It was fun people watching and it was fun seeing some of the women naked, but I was definitely feeling inadequate as most of the men that were naked were well endowed. Several obscenely well endowed and my wife made a few flirtatious comments. Later she said that she was feeling aroused being around all of this nakedness.

We had an afternoon snorkel cruise booked, and we left to go find the boat. We got there a little early so we went to the little cabana bar and got a beer. A few minutes later the boat pulled in and we went over and got on. It was only 3 other couples that loaded on, but then who came on the boat but our friend Daniel. He was apparently on boat duty for that cruise (not the driver, that was someone else). Daniel welcomed us warmly and treated us like friends. He gave my wife a particularly strong drink at her request and then we started nearing the snorkel spot. He started handing our snorkel bags with flippers and mask, and my wife took off her coverup. I saw Daniel look her over with interest, and I looked away so as to not interfere with whatever process was happening. We all got in the water after listening to the rules, and after about 5 minutes into the dive my wife said that she didn't feel great and wanted to go back to the boat. I asked her if he wanted me to go and she said that it was okay. To enjoy myself. The second she said that I know that she wanted to flirt with Daniel and I realized I was getting hard and nervously excited. Not that I thought anything was going to happen on the boat, but it was just kind of a situation developing.

I snorkeled around for another 40 mins or so and headed back to the boat. My wife was sitting with her legs up on the cooler but still no cover up on. Darren was sitting across from her split legged and a very noticeable bulge, and I suddenly went back to feeling kind of insecure. People started showing back up and Darren handed everyone fruity drinks with rum as they got back on. On the ride back my wife told me that Darren asked if we wanted to see some cool parts of the peninsula. He was off and was going to meet some friends. We agreed. Darren picked us up in an open air jeep and we had a great time. We met some friends of his that had all terrain vehicles and Darran had my wife get on the back of the one he was riding and I sat in more of a dune buggy looking one with his friend. We got there first and Darren and my wife pulled up 15 seconds later and my wife's hands were down around Darren's stomach resting on his thighs, and her hands were even lower. I wondered if she allowed herself to slip, and wondered how she was feeling. I didn't get a chance to ask her because we were off again.

Later as Darren was dropping us off my wife asked him if he wanted to join us for a drink. He did and we went into the little covered patio behind our bungalow. My wife got changed and came out in short shorts and a thin cotton belly shirt with no bra, and her nipples were visible through the material, I wondered if she realized how visible they were. Here again I got a little hard at the situation. My wife grabbed some cards and said let's play a drinking game. She told us the rules and the last rule was the loser of the round had to take off a piece of clothes. Darren looked at me I guess to see if I approved, and I looked at her (not saying anything) and then she started dealing the cards. Of course I lost the first round and took off my shirt. Darren lost the next round and my wife said I want to pick the garment. He again looked at me and I just smiled to kind of signify it was okay, And she said "your shorts." He slid his shorts down and he was wearing bikini briefs and my god did I feel inadequate since his cock appeared huge. But I was also really excited about seeing my wife see another man naked in the next few minutes.

My emotions were complicated and the whole situation was almost electrically charged. I don't think I had ever felt that aware and alert and excited all at once. But I was definitely getting in the mood and was getting kind of aroused myself. Finally my wife lost and she asked Darren what he wanted her to take off. He laughed and asked why it felt like only he and her had special rules and she said because I'm the lady and you're a guest. Darren was feeling a bit sheepish I think and said your sandals. She said I'm not wearing sandals so he said your shorts. So she stood up and pulled down her shorts. I then lost and took off my shorts, but I was a lot more humble in my movement and didn't stand there showing myself off for what felt like 30 seconds like he did. Then my wife lost again and Darren named her shirt as the garment to lose. She took her shirt off pretty slow and I will say that when her breasts fell out of her shirt I went into full oh my god this is a fucking awesome experience mode. Darren took a good look at them and then looked at me nervously. I said don't be nervous, we are all having fun here.

Next Darren lost and my wife said "take it out." He stood up and started sliding down his bikini briefs and then his cock fell out and it was something out of a porn movie. Probably 6 inches long, completely soft and about as thick as a vacuum hose. And he went to sit back down and my wife said wait. Come over here. As he got near her she just reached her hand out and grabbed it and I didn't even know what to do. I immediately felt like an intruder. My wife kind of gently pulled him closer by his dick which was starting to get hard. My wife looked at me and I was just staring back at her with a devilish and probably lustful grin and she reached down with her mouth and took his dick into it. Darren got fully erect in seconds and it was very long and very thick around. I would guess 9 or 10 inches. My wife had him sit down and continued working on him there. I was at a loss for what to do so I walked into the house feeling like I needed to give her space. I watched what I could through the glass door. I was so turned on by this that I started taking care of myself with my hand right there. My wife then led Darren into the house and as she walked by me she grabbed my hand and then stopped me short of the couch, like she was putting me in a good position to watch. She laid down and kind of pulled Darren on top of her and his cock was fully hard. My wife was on her back on the couch and Darren was kneeling on the floor. He kind of laid his cock on her stomach, and for a second it gave me a visual of how far he would go into her if he put it in. It went half way up her stomach, and seeing suck a thick hard cock laying on my wifes soft stomach and on her pussy was almost too much to stand there and just watch. Then he started pulling back and the head of his cock was inching closer to her pussy. He then rubbed it up and down and I noticed that the tip of his cock was immediately soaked. My wife was dripping wet.

He slowly started sliding his cock in her and I watched my wife's face. Part surprised at the feeling, part delighted, part fear, and part carnal pleasure. She jumped when he first put it in and then had to hold him so he couldn't go all the way in. By the sounds she was making she was seriously enjoying it and I could see where her hand was stopping the depth of his thrust, and she was slowly letting more and more of him into her. Then he turned her over and she was kneeling on the rug and laying on the couch and he started taking her from behind. I could hear in her voice that she was going to have an orgasm, and she did about 30 seconds later. And it sounded like a very good one. He kept fucking her and then Turned her over again and started fucking her on the ground missionary style. A few minutes later I could tell she was going to cum again, and she did. Also sounded like a good one.

Then he sat on the couch and she sat on him facing him, and she kind of squirmed in his lap for a while and then I realized after another 5 minutes that she was going to come again, but I could tell that he was also getting close to coming, He asked her where he should cum and she just started saying don't stop, don't stop, He again asked her where he should cum and she again said don't stop and I could tell that they were both going to cum, and then they did at the same time in what seemed like a really eclectic experience. I hate to say it but her and I never had an experience like that. He came right inside my wife, and my mind ran through a whole range of feelings about this but I landed on I really need to cum. My wife started pulling me to her but I said I wanted to wait until Darren left, and he got the point. He started collecting his things and left after an exchange of that was funs and goodbyes.

I grabbed my wife by the hand and took her into the bedroom, and I was already oak hard and I slid into her. She was very wet and I realized she had a lot of cum in her. As I pulled my dick out I looked down and I could see I was coated in his cum and it was making my wife's pussy very wet. I tried to hold out and to make her cum (which she does very rarely) but I couldn't last. She started telling me how good Darren felt and I came almost instantly when she said it. I don't think I have ever had an orgasm that good, or where that much cum came out of me, in my whole life.

After we got back home, my wife and I were fooling around one night. She then told me that when she was on the boat she fooled around with Darren when the captain's back was to them. I asked what happened and she said he played with her breasts and she played with his cock on top of his pants and had just taken it out of his shorts to give him a blow job when she saw me swimming back up.

Now I can't wait to go back. I feel like we have had a sexual awakening.