It was time for our annual vacation. Lisa arranged for care for the kids while we were away and we were looking forward to a relaxing week in the Caribbean. Three weeks before leaving Lisa told me she wanted to really relax and asked if we could do something 'fun'?' I knew what she meant. I told her it might be nice for us to just reconnect ourselves and just have a normal vacation like we used to. She insisted and asked to me to see if there were anyone we could meet, would I be able to find someone for just one fun night. I said finally relented and told her 'I'll see what I can do...'. I placed an add on a site that caters to such activities. Over the next week I began getting messages on yhoo IM from a man from the island we were going to. He said he was interested in meeting Lisa and I for a drink and lived about an hours drive from where we were staying. We exchanged a few photos. He loved Lisa's look, and seemed like a nice clean cut guy who Lisa would get along with. I showed Lisa his face photo and she told me 'He looks nice, let's meet him'. 'Mark' gave us his phone number and said to call when we had a free night. We arrived at the hotel and had a few relaxing days at the resort. Lisa spent some time shopping, and came back with a few bathing suites and short black mesh dress. She looked great in it but it was not what she ordinarily chose. It was very short, with a low cut neckline and was mesh which was slightly see through. With 4 nights left, Lisa told me this was for our 'special night'. The next morning over breakfast Lisa asked if I had called Mark yet. She said we should get together with him because we'd be heading home in a few days. I called him and we arranged to meet him. He would come to our hotel in the afternoon to meet and since we had planned on going diving that afternoon, he would join us. When he arrived, Lisa hit it off very well with him. He was about 26, and Lisa liked him right away. We soon left for the dive. Once on the dive boat I became alittle seasick so Lisa buddies up with Mark for her dives. As the boat returned to the dock, Lisa invited him to meet us for drinks after dinner. he eagerly agreed and we arranged to meet around 8PM in our hotel bar. We were running late that evening, so while Lisa finished getting ready, she sent me to the bar to meet Mark. I sat there for 30 minutes nervously waiting. Soon he tapped me on the shoulder, shook my hand and introduced me to his Friend. He had brought one of his buddies. He said his Friend needed a ride over to our area and he had given him a ride. Deep down I think I knew what they both wanted. I called Lisa and told her that Mark had arrived and we were waiting in the bar for her. She arrived a few minutes later, gave Mark a big kiss and then he introduced his Friend. She was surprised by this, but went with it and we all talked for about an hour over drinks. We all had a few drinks at the bar and then she told me she wanted to get a bottle of wine and go back to the room. She invited Marks Friend to join us. Lisa went to the room with both of them and I went to get a bottle of wine at a local store. When I got to the room I opened the wine for us all. The guys seemed uncomfortable so Lisa asked me if I would mind staying out on the balcony for a while. She whispered to me that I could turn on the camera but just leave it on the table, then she opened the door and got down to business. She went to the other room and put on a see thru nightie and sat on the bed with Mark, he started by giving her a back massage. They undressed each other as I watched from the balcony. Lisa sucked his big cock and looked over at me, smiling at me with his cock in her mouth. He got her up on her knees and fingered my wife from behind as she blew him. I could see him put 3 fingers into her wet pussy before turning her over and sliding his cock inside her. His Friend just sat and sipped his wine patiently and watched while my wife got it going with Mark. I had been asked to leave the room but his buddy saw the camera and picked it up and videoed Lisa sucking and getting fucked by his buddy. He soon put the camera down and joined them on the bed. I began to masturbate on the balcony as Mark fucked her from behind and his Friend walked to the edge of the bed, my wife taking his cock into her mouth and started to suck blow him. They did this for 10 minutes or so, then switched positions. These two men were fucking my wife, as I sat on the balcony masturbating. I had a hard time understanding how quickly this all unfolded, this was unbelievable to me, but was happening and I could not or would not be able to stop it now They then took turns fucking my wife as if she was some slut. I watched from the balcony as Mark fucked her from behind, his Friend video taping as he pulled out and came all over Lisa's ass and back. He spread his cum on my wife's ass and back and then his Friend took his turn. Lisa soon brought his Friend to orgasm with her mouth, taking his load on her face and tits. They left around 3AM and Lisa let me in to say goodbye to them. They were laughing as they left, telling me that next time I should send her on vacation alone. Lisa laughed and agreed. She was exhausted and sticky with their cum. I could see it on her face and neck. As I lay next to her in the bed, the scent of their cum was unmistakable and kept me awake most of the rest of the night. She told me the next day that she had never been so excited as she was last night. She thanked me for not interfering and staying on the balcony. She said it was comforting knowing I was close by, but liberating knowing that I was not a part of it. She said she felt badly for me, and that she also felt 'like a whore and a bit slutty'. I knew she was not a whore, she would never have sex with someone for money. But she had reached a new level of slutty-ness. But she said did not regret it at all, because it was an 'amazing experience'. On the plane ride home, I can't help but feel we have reached yet another level.