Caribbean Vacation Fantasy

Copyright © 2010 Caribberos

My first trip to the Caribbean was in the 1970s. Yes, I am middle aged and this is a story about middle aged people -- average people, no gorgeous babes with huge tits, no twelve inch cocks that can stay hard for twenty-four hours straight, just average looking, middle aged, middle class Americans.

I love the islands and we have been fortunate enough to have traveled there almost every winter since the eighties. My favorites are the French West Indies because the French have two things going for them: great food and a relaxed outlook toward nudity. In fact, the whole feel of the French islands is more relaxed and comfortable with a slower pace. An early dinner would be anything before eight pm and they expect you to be at your table for the entire evening.

What makes this, or any story interesting is not just the events but the characters involved. A story about wild sex with a character who has wild sex every day is just a story about wild sex. But when the characters involved are middle class, average guy or gal next door types, conservative family-oriented types then the wild sex becomes even more unlikely and thus more interesting. When the characters act completely out of character, it becomes more than just wild sex.

Mary and I have been married now for over thirty years but the events described here happened back in the nineties. That was the age when our kids were getting old enough that we finally start thinking about ourselves again and about what life might be like after the kids are gone. We had spent most of our time and energy focused on raising the kids and we had lost touch with most of our past friends and we had developed some friendships with parents of our kid's friends but nothing close.

I am a few inches over six feet tall, slim but not skinny at about 200 pounds. I am reasonably attractive and most people tell me I look way younger than my age. Mary is about ten inches shorter than me and even though she is putting on a few pounds now I think she still looks great and back then was even better (as we all were). She has dark hair, 36C boobs, and has a naturally beautiful face that doesn't need any makeup.

Mary is a bit more conservative than I, hardly ever drinks, thinks of the kids all the time and would never be imagined in a "sexual" situation in by anyone who knew her. This is what makes the events that are about to occur so amazing to me. I long ago accepted that I married the woman that I love "bringing home to Mom" or raising my kids and not the sex crazed nymphomaniac that my hormones would have enjoyed more.

Mary's conservative dress and appearance have a lot of people fooled though and we have always enjoyed an active sex life but she really comes alive in the Caribbean. I suppose, like a lot of people, she needs to get away from it all in order to relax. We have had our best sex when on vacations alone but it has always been alone and she has always been turned off by my fantasies of sex with others or even talking about our sex life with others.

We met Rob and Lynn through our kid's activities and had known them for several years before we started building a relationship. We had started doing family get-togethers, and dinners or movies out once in a while. Rob has a quick wit and a wonderful sense of humor and makes me laugh a lot. He smiles a lot and has a positive attitude so he is fun to be around. He is a couple of inches shorter than me and a few pounds heavier. The more we got to know each other the more we enjoyed hanging out together.

Lynn is even shorter the Mary at about five -- two. At the time she was only about 125 pounds and she looked great. Her best assets are her legs -- perfectly shaped with smooth and flawless skin. I had started noticing her legs about a year or so earlier and on many occasions had enjoyed watching her from behind as she teasingly shook her booty at me as she walked in heals. She is supper light hearted, always laughing and has an adventurous side that none of the rest of us have. To sum it up we were just four average, middle aged adults raising families.

As fall started its turn to winter, Mary and I started talking about our annual trip to the Caribbean and started picking our island. One day I asked Mary what she thought about inviting Rob and Lynn to join us on this year's trip. We talked about it and agreed that we would be giving up a lot but potentially gaining a lot in a deeper relationship with our friends. We also agreed that we would not give up our own annual private trip so if this developed into a regular thing we would have to take two winter vacations to the Caribbean each year -- one with friends, one alone. Sounded great to me!

The next time we got together with Rob and Lynn we brought up the idea and invited them to join us on our vacation. After some discussion they agreed and we decided that a good island for them to first experience the Caribbean would be St. Martin, a good mix of sand, sun and great views with its nude beaches, plus incredible French cuisine.

The hotel we chose was an all inclusive on Orient Beach, near the world famous nude resort. We figured walking the beach from one end to the other would be a good daily exercise activity, and provide some stimulating views.

We checked in to find that the resort was way below our expectations but we figured we would make the best of it and tough it out. That is until the second night when Rob and Lynn woke up to find two inches of water had flooded their room and we were completely disgusted by the food and the filth. That day Rob got on the phone to the travel company and put up enough of a stink that they told us they would refund our money and we could find our own hotel to finish the stay.

We headed out to scout out the island and after several hours of driving we found a remote hotel on the north end of the island. We parked our car and walked into the resort where we were greeted by a beautiful large, columned building which was the main lobby for the resort. We walked into the open-air building and immediately fell in love with the place. Someone playing at the grand piano, the beautiful gardens in the enclosed courtyard, the friendly staff, all screamed this is the place you need to be.

I jokingly knelt down and front of Rob and begged him to arrange for us to stay here -- no matter what the cost. He laughed and pointed to his crotch which was only inches from my face at the moment. I looked over at Mary and said "Tell Rob you will give him a blow job if he gets us rooms here."

"Rob, I will give you a blow job if you get us rooms here" she said without hesitation.

All four of us looked at each other for several seconds in silence before we burst out in laughter; this was so out of character for my conservative Mary. As we laughed, Mary turned a bright shade of red as what she had just said to another man in front of her husband began to sink in. I quickly went over to her and gave her a big hug and a loving kiss to assure her everything was ok.

Arm in arm and laughing like school children, the four of us headed to the front desk and Rob began negotiating for two rooms for the rest of the week. Within two hours we were back, bags in hand, checking into our new hotel.

The bellman brought us and our luggage to our rooms which were right next to each other, on the first floor, with large sliders opening to patios facing the gardens at the edge of the property. The rooms were about two hundred yards from the incredible Caribbean Sea but the setting facing the gardens was very secluded and private.

We agreed to stay at the hotel and dine at the hotel restaurant that evening as we had all had enough driving for the day. I made reservations at the restaurant for seven-thirty and we agreed to meet at seven for a drink in the bar. This gave us about two hours to get settled in our room and get freshened up for the evening. Alone in our room for the first time we fell on the bed in exhaustion and sighed in relief. We were so happy to be out of the dump we had been in for the last two nights. I think we both drifted off for twenty minutes or so without moving. I woke to the sounds of the Caribbean wafting in through our open patio door, got up and grabbed a Presidente Beer from the stocked fridge.

One hit on the beer had me more relaxed than I had been since we arrived on the island and I stripped out of my clothes and wondered over to the patio, parking my naked ass on a toweled chair, my feet on the table and enjoyed the rest of the beer. I gazed over at Mary dozing peacefully on the bed and began to imagine what fun we might have on our vacation.

From my chair on the patio I could hear the muffled voices of Rob and Lynn next door. It was apparent they had left their door open as well and were on the bed engaged in some private fun. I smiled as I imagined them relaxed and enjoying themselves for the first time in two days as well. I was so happy we had moved to the new hotel rather than ruin our entire vacation -- and their first Caribbean trip -- in the dump we had left.

Going back in the room I gently climbed on the bed and straddled Mary, softly nudging her from her slumber with kisses. She awoke slowly and our lips met in a brief kiss. I let her get her bearings and shake off the grogginess before kissing her again, this one a deep, loving kiss that brought her fully to her senses.

I suggested we unpack, share a shower and get ready for our evening out. In the shower Mary was starting to show me her Caribbean wild side and my cock was springing to life in anticipation of what was to come. I had almost given up on any hope that this was going to be a sex filled vacation as we had in the past.

Mary's mouth is almost exactly at the height of my nipples when we are standing and holding each other, very convenient given that I love it when she bites on my nipples. She was kissing my chest and moved slowly to the left, flicked her tongue a few times and then drew my nipple between her teeth.

The mixed sensation of pain and eroticism raced from my left nipple to my cock and then to my brain. My erection twitched to life before my brain kicked into action and before I knew it, she was biting on my right nipple. Oh how she knows how to get me going!

I grabbed the back of her hair and gently but firmly pulled her head back. At first she didn't let go of my nipple and my pulling of her hair resulted in an equal pull of my nipple. I could have gone on with this game for a long time but Mary opened her grip and released my nipple with a final twitch of pain. She looked up into my eyes as our open mouths met in a wet tongue searching kiss.

I suggested we hold this place and pick up here after our dinner. I know that sounds like a strange thing for a horny guy with a raging hard-on to say but over the years I had learned that it was far more enjoyable to go out in public very horny than very satisfied. We tend to be much more touchy and sensual if we don't finish things ahead of time.

As we dressed for the evening I was pleasantly surprised to see Mary dressing sexy, especially for her. She had taken out black high-heeled sandals, a short, loose skirt and a sleeveless top that buttoned up the front. She put on a black lace push-up bra and then buttoned the top so that the top two buttons were open to reveal her cleavage and the lace edge of her bra. The only time she had dressed even close to this was when we were alone on past trips. I smiled at her in the mirror grabbed her tits from behind and kissed her on the neck telling her how much she turned me on.

We met Rob and Lynn at the lobby bar at seven as agreed. Rob looked more relaxed than I had seen him since before we left home and Lynn looked incredible in a short, tight skirt, heels and white top that was sheer enough to see her bra underneath but not so sheer that she looked cheep. Her ample nipples pressed discretely against the fabric.

I love being in the presence of sexy women. I don't think there is anything that gets the testosterone flowing faster than two men showing off their women to each other. This is one of the many things that actually gets better with age.

We ordered drinks and sat down across from each other in low comfy chairs with a low coffee table between us. I was across from Lynn with Mary to my right, across from Rob. As I held Mary's hand and relaxed into the chair, I stretched out my legs under the table and kicked my boat shoes off. A moment later I felt Lynn's bare foot gently caressing the top of my foot. As my cock twitched in my pants I had the thought that this could be an interesting vacation after all.

Rum punches all around to start the evening. Both Mary and Rob are not much into drinking but this was a special celebration time and they both like the sweetness of the rum punches. The first ones went down quickly and had two more rounds before our table was ready in the restaurant. We were all enjoying the relaxed conversation, piano music in the background, wonderful weather and the general feeling of paradise we were in. The conversation was light and lively and there was an occasional joking mention of the payment that Mary owed Rob for setting this all up.

I ordered a rum and coke and was surprised when Mary ordered one as well. She enjoys them occasionally but one drink is usually her limit and she had already had three rum punches. We ordered appetizers and settled in for a slow, relaxing French dining experience.

The casual, relaxed conversation combined with a few drinks had us all feeling good. We talked about some of the sights we had seen on the topless beaches and started to get to know each other a little better in a 'revealing' way. Rob and I were leading the conversation -- being raunchy guys -- but Lynn was holding her own as well. Mary was laughing at the suggestive conversation even when it came back to the blowjob she owed Rob.

At one point I told Rob he was really going to love it and proceeded to describe Mary's cock sucking abilities. I told him that if he really got her going he might even be able to convince her to turn around and sit on his face at the same time. I couldn't believe I was talking about my wife like that to another man and I thought she was surely going to put a stop to the conversation with that one but instead she hit me on the arm and told me to stop it with a smile on her face that said I didn't really have to stop.

I had never seen her like this before. As I have said, she and I have always had great sex while on vacation in the Caribbean but she had never liked it when shared specifics about our sex life, much less her personal sex drive or abilities. It was like she never wanted anyone to know what was hidden beneath the conservative shell.

Lynn must have been feeling left out because she suddenly said "I think that if Mary is going to give Rob a blow job that good, then I should give one to Fred at the same time." I just sat back and smiled at the thought of that as I felt Lynn's foot caressing my leg again under the table.

Our meals arrived and the conversation calmed down for a while and turned more to food than sex. The food was great and the accompanying bottle of wine relaxed us even more. It was almost midnight before we left the restaurant and headed back to our rooms. We were giggling and stumbling a little and we ended up with all four of us walking arm in arm, boy-girl-boy-girl. Rob was the lucky one in the middle with Lynn on one side and Mary on the other. Mary didn't seem to be holding back as she had her arm wrapped around Rob's waist.

As we stopped to say good night at our rooms it was Rob who made the first move, approaching Mary and placing his hands on either side of her head, bending down and softly saying "Good night" before kissing her on the lips in a slow sensual kiss while Lynn and I stared in shock. Mary made no effort to pull away or stop him and I am sure there was some tongue action going on. When Rob finally released her she looked into his eyes for the briefest moment before looking over at me and instantly turning red.

Somehow I knew now was not the time to give her a hard time, even jokingly, nor was it the time to reciprocate by kissing Lynn -- as much as she or I may have wanted to. Instead, I quickly slipped around behind her, bent down to wrap my arms around her from behind and tenderly kissed her on the neck. I whispered in her ear "I love you so much and I want you so bad."

We all said good night and unlocked the side by side doors to our rooms. The ladies entered the rooms first and I looked over at Rob, smiled at him and gave him a wink to assure him that I was ok with everything. The truth is that I was better than ok, I was super turned on by what I just witnessed -- the love of my life being deeply kissed by another man and obviously enjoying it. The image of her giving him a blow job filled my mind as I closed the door to our room.

The second the door was closed I approached Mary from behind and began kissing her on the neck again as I unbuttoned her top and unfastened her skirt. The skirt fell to the floor as I watched in the mirror and was shocked to see that she had no panties on underneath. I had only talked her into going pantiless a few times over the years and here I had just spent an entire evening with her and didn't even know it. I dumbly said "I didn't know you had no panties on; were you like that all night?"

To which she replied with a smile "You might have noticed if you weren't working so hard to get a view of Lynn's tits."

"Well, I can make it up to your right now" I said humbly as I slid my hands down her thighs and in toward her pussy. We both watched in the mirror as my hands approached and she moved one foot sideways to give me easier access.

My right hand won the race to the finish line and I plunged my fingers between her lips. Again I was shocked as I realized how wet she was and the smile on her face widened as she revealed this additional secret to me. "Oh my god, you are soaked" I said in shock.

"I know," she said, "I have been having fun tonight."

"Imagining what I am going to do to you?" I asked.

"That, and maybe a few other things."

"Like what?"

"Oh, I don't know, maybe what's going on next door, things like that."

I finished undressing her as we talked and quickly dropped my clothes on the floor as I moved her toward the bed. I laid her back and knelt next to her kissing her lips, then moved to her nipples, then down her soft belly and finally to her soaked pussy. As I approached, her legs opened automatically and I was overwhelmed by her beautiful aroma. Inhaling deeply a savored her scent before inserting my tongue for a taste. So sweet, so slick and wet!

As I licked her, she played with my cock for a few minutes and then I felt her pulling at my left leg, indicating she wanted me to lift it. I complied with her request and moved into the sixty-nine position. I buried my face even deeper into her trimmed, wet pussy only to feel her pushing my legs again to get me to pull my knees up toward my head. Again I complied as I felt her pull my hips down toward her mouth -- and then the wonderful feel of her breath and then her tongue on my asshole. I thought I had died and gone heaven.

Several minutes in this position had us both breathing very hard and I felt the first pangs of orgasm building in me. "On no, not yet you don't. I am going savor this as long as I can." I thought to myself as I reluctantly rolled off her.

"I want you on top" I said as we quickly repositioned ourselves.

Back in the sixty-nine position but with her on top, she began to suck my cock with a vengeance while I slowly spread her lips and examined her soaking, pink hole before plunging my tongue back in.