Caribbean Surprise 1

After 30 years of ups and downs as a married couple, my wife Anne and I had decided that we deserved a special vacation to celebrate our anniversary. After weeks of talk and research we finally settled on the Dominican Republic as our destination and we found the perfect resort on the eastern shore of the island. The hotel we picked was the flagship of a four hotel complex that offered a wide array of restaurants and night life, all available for our use at an all inclusive price. Best yet, Anne and I loved the beach and the beach at this resort was know to be world class.

The day of the trip we had flown to Atlanta from Newark and were waiting in line to board our second plane to the Dominican Republic. As Anne and I stood in line, my eyes fell on a woman just ahead of us. I had noticed her earlier sitting with her husband, and our eyes had connected briefly. She and her husband looked to be a good ten years younger than us. She was pretty, in a soccer mom kind of way, and I remember thinking to myself, "now that's a mother I would love to fuck." As we stood in line to board, she turned around to look to see if her husband was coming and she noticed me looking at her again. I smiled at her and she smiled back. It was all innocent and if Anne noticed I doubt she thought anything of it.

I didn't really think about her again until after we had landed in the Dominican Republic. As Anne and I were being herded through Customs I spotted her in a different line, some distance away, and I swear she was looking directly at me. There had to have been hundreds of travelers there, but she had picked me and it was quite flattering. She smiled at me again and I started to return the gesture when Anne interrupted the moment by asking me questions about the Customs forms we were filling out.

We made it through Customs fine and went off to find our baggage, all the while my new friend and I seemed to be having a little game of harmless flirtation going on. It was subtle and I don't think anyone noticed but us, including our spouses. She and her husband located their suitcases much faster than us and that's when I finally lost her.

Anne and I took a shuttle bus to the resort and, after check in and orientation, we found ourselves standing in an amazing hotel room. The bedroom was beautiful and the bed was enormous, and after a "finally we're here" kiss, I impulsively tried to guide her to it. It was late afternoon, however, and Anne wanted to see the beach in the worst way. I suggested we pull out our bathing suits and unpack the rest after a visit to the beach.

Anne had packed our suits where they were easy to get to and soon she was stripping off her travel clothes. At 53, Anne had grown more attractive to me than ever. Her dark, brown hair fell just below the top of her shoulders and formed a natural frame around her pretty face. Her soft full lips and her pretty brown eyes always drew my attention, and the attention of other men too, although I doubt she ever realized it. At 5'6" and 155 pounds, she was no fashion model. She was definitely developing a little bit of a belly on her medium frame, but she carried it well. Her breasts were just the right size to cup in your hands around, and her hips, perfect round ass and smooth, sexy legs all helped her look great in a bathing suit.

We spent an hour or so on the beach, which was indeed world class as promised. I brought the camera and got some great shots of the ocean, the beach, and of Anne. The lighting was perfect in the late afternoon sun and I wanted to take a few more, but it was getting late and we were both pretty hungry so we returned to our room, unpacked and dressed for dinner.

At this resort you are assigned a table for your stay for dinner in the hotel restaurant. There's no obligation to eat there - there are several other choices on the complex - but if you do eat there you are assured of having the same waiter or waitress throughout your stay. Of course other people would be assigned to your table, but there was a good chance they'd eat elsewhere or at a different time. It looked as though we were going to have the table to ourselves.

I had just finished going through the buffet line and was headed back to our table when I noticed Anne, who was ahead of me, talking to a man and a woman who looked familiar. They had been seated at our table. I stopped dead in my tracks when I realized it was the same couple from the airplane. My first impulse was to hide but, of course, I knew I had to go over and introduce myself.

I soon discovered that I had nothing to worry about. Other than a hand shake that lingered a little longer than necessary, both my airport friend and I played it cool. Her name was Sarah and her husband's name was Dan and we soon discovered that we had much in common.

Dan and Sarah were both teachers, as was my wife. Dan taught high school Honors English and my wife taught high school AP Math. Sarah taught fifth grade. It turned out we both had daughters, their two still in elementary school, two of ours in high school and a third in college.

We also discovered that Dan had grown up in the same city as my wife and they had actually gone to the same high school, though several years apart. While Dan and my wife talked about teachers and places they both remembered, Sarah seemed fascinated to learn that I owned a small book store. She pumped me with questions, occasionally putting her hand on my wrist to emphasize a comment.

In hindsight I would say that Anne was quite taken by Dan. He was pretty good looking, about 6' tall, perhaps 180 pounds, definitely a man who worked out. His brown hair and brown eyes contrasted my blond and blue. He had that "Jim Halpert" from "The Office" look that I knew Anne found sexy. More than that, he was very easy to talk to and Anne loved to talk.

We ended up conversing and drinking wine for long time after we'd finished eating. The age difference didn't seem to be a factor, and I could feel a genuine budding friendship developing as time flew by. We finally said our good nights and agreed to look for each other on the beach the next day.

In the elevator Anne told me she really liked them and I told her I agreed. We were both looking forward to seeing them again. Once we were back in our room my mind shifted gears and I started thinking about fucking Anne. I grabbed her from behind and started kissing her neck as soon as she started unbuttoning her blouse. Anne had a different idea though. Sleep. Actually it had been a very long day and I didn't argue with her.

When we woke up the next morning Anne began kissing me and before I knew it she was on top of me humping away. Back home Anne almost never initiated sex and the last time she dry humped me was before we had kids. After thirty years of marriage, our sex life had become very routine, so I was moderately surprised by what was happening. It only took her a few minutes to cum hard and then she rolled over on her back, exhausted. I helped her out of her night gown and pulled off her panties and fucked her missionary style for some time, thinking about Sarah as my cock slipped in and out of her cunt. She finally urged me to finish and I had a nice, stong release deep inside her.

Later that morning we meet Sarah and Dan on the beach. They had saved us lounges under the protective shade of a palm grove. Sarah was wearing a yellow bikini that looked really hot on her. She was more petite than Anne, a couple inches shorter and at least twenty pounds lighter. Her breasts were larger than Anne's but not so large that they dominated her nicely proportioned frame. Her shoulder length brown hair (a little shorter and a little lighter than Anne's) was pulled back into a ponytail. After figuring out when Dan had graduated from high school from our conversation the night before, I calculated that Sarah was probably around 38 years old.

We spent a lot of time with Sarah and Dan over the next couple of days. They were fun to be with and I believe they thought the same of us. We explored the other hotels and their restaurants and pools and went to a couple of shows together. We also ate together, trying out new places for lunch and coming back to our hotel for the dinner buffet. The attraction between Sarah and me had morphed into a kind of harmless group flirtation between the four of us. It seemed like it was all in good fun, but deep down I felt that it was becoming more that just a game between Sarah and me, and I worried about our spouses catching on.

I was certain Anne would bring up the open flirting and say it was making her uncomfortable. She didn't and that surprised me. What surprised me more happened in our room that second night. Not only did Anne let me have my way with her, she let me indulge in a fantasy involving her and one of the black men who served us drinks that evening. She never let me talk about my fantasies back home. I rubbed her clitoris as my story unfolded and she climaxed as I described his large cock pumping semen into her wet vagina. If that wasn't shocking enough, the next morning she wanted to fuck again! I told her another fantasy about a college kid we know who accidentally finds her home alone in the shower. She came hard before I could get to the end.

On the third day Sarah and I were alone on the beach for a few minutes when Anne went back to the hotel to use the bathroom and Dan went back to get his camera. Sarah asked me to help her put on some sunscreen. After I finished with her back, she turned around and I had an overwhelming desire to kiss her. I know she felt the same, but we both just stood there staring at each other. Finally she touched her fingers to my mouth and sat back down on her lounge. Shortly afterwords Dan appeared and my opportunity was lost.

The fourth day of our vacation began with some pretty feisty morning sex. Anne rode me to a strong orgasm and I finished a little bit later by rolling her over on her tummy and masturbating all over her pretty ass. I was just headed to the bathroom for a towel when I heard a knock on the door. I had forgotten that we requested fresh coffee be delivered the night before. I quickly pulled on some shorts and a tee shirt, closed the door to our bedroom and walked through a little bar area to the outside door where a nicely built black man was holding a serving tray of coffee. I expected he would hand me the tray and I would give him a tip and that would be it. I was surprised when he pushed right past me and headed for the bedroom. I tried to tell him to just leave the coffee with me, but he pretended he didn't understand me and pushed his way right into the bedroom.

Anne was completely naked and just barely had time to pull the covers up over her breasts. We both watched in silence as he set the service tray down and poured out two cups of coffee. He had his back turned to Anne but I could see him checking her out in the mirror. I pulled some money out of my pocket and he took it with a polite nod. Then he smiled at Anne and left.

Dan and Sarah had reservations for para sailing that morning, so Anne and I decided to check out an avenue of shops between two of the hotels on the property. We met them for lunch later on and we all had a good laugh about our coffee story. Dan said he'd deliver coffee to us for free next time.

After lunch we decided to go pool hopping. Each hotel on the property had it's own unique pool and we thought it would be fun to visit them all in one afternoon. My favorite pool was the last one we visited. It had a great swim up bar and large hot tub area that resembled a little lagoon. It was surrounded by natural looking rocks which lent a sense of privacy. You could get to it without ever leaving the pool. Sarah had promised her daughters she would call them after they got home from school that day and she excused herself to go back to the room. Shortly after Sarah left, I offered to grab some beer for us. I left Dan and Anne alone and made my way out to the pool bar. The bar was mobbed and after a couple of minutes of waiting I decided it would be smarter to come back after it thinned out some.

As I was coming around the rocks that led into the lagoon I paused. Something wasn't right. Anne had a serious look on her face and that puzzled me. She didn't see me standing there and Dan had his back to me, so I stood still and watched. Then my heart stopped. As I stood there, Dan leaned over and kissed Anne on the mouth. It was a gentle, tentative kiss. I fully expected Anne to pull away, but instead she put her hands around the back of his head and kissed him back. Hard.

In thirty years of marriage I never once suspected my wife of cheating. Now I wondered if she held secrets from me that I was never intended to know about. I stood there immobilized. I was definitely angry but I could feel my cock stiffening at the same time. When the second kiss broke, Dan took two fingers and traced them down her chest to the top of her swim suit. He slid the fingers inside her suit and traced the upper parts of her soft tits.

Anne gently pulled his hand away and I thought she was coming to her senses. But, instead of backing off, Dan slid his hand down her tummy, under the bubbling water and out of sight. I watched as Anne bit her lower lip and slipped lower into the pool. Though I couldn't confirm it, I was pretty sure she had opened her legs and Dan was rubbing her cunt.

I had no idea what I wanted to do. There were other people in the lagoon, but it didn't seem as though anyone noticed what was going on. Then I saw an older man looking on with great interest. His hand was hidden under the water too, and the look on his face told me he was stroking his cock while he watched. He looked over and saw me and quickly looked away.

Finally I decided to do nothing. I went back to the pool bar and waited my turn to be served. When I returned, Dan asked me if I had gone to Cuba to for the beer. I mumbled something stupid and then did my best to pretend everything was normal. We drank our beers and headed back to our rooms to get ready for dinner.

When we were back in our room and Anne was changing out of her swim suit, I probably could have told her what I saw and we would have talked about it. Instead I groped her. I wanted my hands to touch the same places Dan's hands had been. I kissed her gently, like Dan had done with her, and she kissed me back hard, like she had done with Dan. It was pretty weird and erotic at the same time. When my hand slid down her tummy and started to touch her hairy pussy she started to cry. She pushed my hand away and told me she had done something bad.

I listened to her tell me about her encounter with Dan. I didn't let on that I actually saw most of it happen. At first she left out the part about Dan's wondering fingers, but she described the kissing part just as I had witnessed it. I told her I loved her and I wasn't angry. I told her that she wasn't a bad person, that she was only human. I held her naked body tight to my own and I told her I wasn't about to leave a good marriage over a kiss. Then guilt seemed to get the best of her and she told me there was more.

I listened intently as she confessed to the rest of what I had seen. I was a little surprised when she revealed that, not only did Dan touch her pussy, he actually slipped his fingers inside her. She said she broke it off when she saw an old man staring at her from across the pool. I was silent for a minute and then I said, "It's alright, Anne. This still doesn't change anything." Then, I don't know why, but I asked her if she liked feeling Dan touch her. She immediately said, "no" ......and then she looked down at the floor and whispered, "yes". My cock was as hard as a rock.

We talked about what to do next and finally decided to keep Anne's confession just between us. I convinced her that I had no ill feelings towards Dan, and thought that he was a good and decent person. I honestly didn't want to end our new friendship, but more truthfully I was thinking this could be my free pass to pursue Sarah. I didn't say that to Anne. Instead I said, "Who could blame him for wanting you so bad, most of the boys in your math classes walk around with hard-ons all day thinking about what they'd like to do to you!" She didn't appreciate that comment.

We composed ourselves, dressed for dinner and met Dan and Sarah at our usual table. We were late but they didn't mind. Anne was quieter than usual while we ate. I knew she was nervous because she practically guzzled her first glass of wine and consumed two more glasses before dinner was over.

After dinner we walked down to the beach to see the moonrise and then we went to a comedy show at an outdoor amphitheater. When the show was over, Dan invited us up to their room to watch a video he had taken of Sarah para sailing that morning.

As Dan set up his laptop, I volunteered to mix up some gin & tonics, keenly aware that when Anne gets drunk she often loses her inhibitions. I'm not sure what I wanted to happen, but I was horny enough to take a risk. Dan set the laptop up on a coffee table in front of a small couch. Dan and Sarah sat on the floor and, after bringing out the drinks, I joined Anne on the couch. After the video we looked at photos Dan had taken of the vacation so far, and then some other pics from a trip to Cancun.

I went out to fix more drinks and when I came back Dan had moved up to the couch with my wife, so I sat next to Sarah on the floor. It was hard for me to see the screen at that angle, so I put my arm behind Sarah and leaned in to her a bit in order to get a better view. I think we were all feeling the alcohol by this time. Sarah snuggled into me and I put my arm fully around her as we watched. Neither Dan or my wife said a word.

Dan got up to get the third round and I could tell from the first sip that he'd made them extra strong. There is fine line between getting drunk and losing your inhibitions and getting drunk and not being able to function. When Anne started slurring her words I was afraid we'd crossed the line. We were discussing logging on to Anne's facebook account to look at some of our kids pictures when Anne abruptly announced it was time for her to go to bed. She tried to stand up and almost knocked the computer over.

I realized that I had to get her up to our room and that any chance of fucking Sarah from here on in was highly unlikely. I was just drunk enough myself that I failed to get Anne off the couch and Dan and Sarah had to help me. After we got Anne standing, Dan took one arm and I took the other and we pointed ourselves towards the door. Sarah said, "come back soon," and I wasn't sure if she was talking to her husband or me, or to both of us.

We made it up the elevator and to our room and I planned to just lay her down in bed and let her sleep it off, but Dan asked, "shouldn't we take her clothes off?" I went to pull out her nightgown but it wasn't where I thought it was. By the time I got back, Dan had removed her shirt and was undoing her bra. Anne stood up on her own power and unfastened her shorts and began to pull them down. She stumbled into Dan and they both fell onto the bed. I pulled her shorts off and was suddenly aware that Dan was groping Anne's left breast. She looked at me as if to say, "I can't help myself", and then turned her face to him and they kissed each other, right there in front of me. I laid down the nightgown on the bed and sat down in the chair and started to rub my penis.

As they kissed, Dan moved his hand over and around Anne's tits, squeezing her nipples one at a time. Then he moved his hand down between her legs and rubbed her cunt through her panties. Anne opened her legs slightly, pulling her right leg up so that she could push her pelvis in rhythm to his strokes. After three of four minutes of this, she was breathing pretty heavy and started to cum. Dan pressed on and she came in waves. When she was finished Dan sat up and began undressing.