Cuckolded on Vacation by a Younger Man

Cuckolded on Vacation by a Younger Man - I would like to share a new and recent experience my wife and I had on vacation - one in which I became a cuckold. I apologize for the length of the story but I hope that you will find the read worthwhile.

I am 41 years old and my wife Leslie is 35. Our vacation took us to an adults-only resort on one of the islands in the Caribbean. The purpose of our vacation was to celebrate our upcoming 10th wedding anniversary. Although our anniversary is in March, we decided to go to the resort in late January in order to escape the winter cold.

Since we do not have any children, she has been able to maintain her figure and she looks more like a woman of 25 than 35. To the best of my knowledge, she has always been faithful to me even though our sex life has gradually lost most of its sizzle. She has never complained but I've always believed that my puny 5" dick has never truly satisfied her and I've usually relied on my fingers to bring her to orgasm. She has never been secretive about her attraction to big, muscular men and, although she has never said so, I'm sure she has fantasized about having sex with the well-hung studs we've seen in adult videos.

Getting back to my story, after we made our travel arrangements, Leslie decided that she wanted to buy some new swim suits for the occasion. We went to a shop in a downtown mall and she started browsing for something to sunbathe in. I pointed out a very sexy bikini on a mannequin. She asked me if it wasn't a little too daring and while I agreed it was, I reminded her that we were going to an adults-only resort which also had a private nude beach. I also mentioned that the resort was frequented by a lot of Europeans and that European women often went topless. Therefore, I concluded, it was not very likely that she would garner that much attention. Besides, I said, she wouldn't be able to wear something like that too much longer and that we wouldn't be seeing anyone we know. That observation didn't seem to amuse her and she asked me if I was suggesting that she was getting old and/or fat. Having put my foot in my mouth, I tried to reassure her that she was just as sexy as when we got married but that didn't seem to pacify her. I think as revenge she scanned the rack further and deliberately chose a pink thong-style suit that I knew wouldn't cover her whatsoever. She also picked out a more conservative and traditional two-piece suit for walking along the beach and a one-piece for swimming.

After we got home, she immediately tried them all on and she looked absolutely stunning in all three of them. As I feared, the pink thong outfit concealed little more than her pussy (after she did a lot of trimming) and the top could do no more than cover her nipples and provide some support for her breasts which were spilling out everywhere. Looking at how sexy she was and knowing that every red-blooded man would be checking her out, I was beginning to regret my earlier remarks.

We arrived at the resort around noon on a Saturday. After unpacking and freshening up a little, we applied sunscreen lotion all over our bodies, wrapped ourselves up, and headed for the pool. We positioned ourselves at the end of the pool facing the main resort building and reclined in the chairs. There weren't many people around the large pool and Leslie quickly seemed quite at ease after removing her wrap despite being practically naked. After quite some time, I decided that the sun was getting a little too hot for me and I told Leslie that I was going to retire to the shade of the bar situated in the pool.

I entered the pool, swam to the bar and ordered myself a drink. Perched on one of the stools, I turned to face the pool and took in the beautiful views afforded not only by the scenery but by the sight of my wife's beautiful body as she worked on her tan. By the time I started on my third drink, a young, nice-looking, muscular man appeared at the pool and headed for a chair not too far from Leslie. Undoubtedly, the sight of my wife's nearly naked body attracted him to the spot as there were plenty of other places to choose from. I grinned knowingly to myself as I watched him and knew what must have been running through his mind. My grin was cut short, however, when the guy dropped his shorts to reveal a Speedo type swim suit doing its best to conceal what looked to be an enormous cock. Even from my distant vantage point, the size of his bulge made me literally gasp in amazement. He picked a chair which gave him a side view of my wife's shapely body and the sight of her was no doubt a big turn on for him. Lying on her stomach with her head turned away, Leslie did not know he was there thus giving the young man the opportunity to ravish her body with his eyes without the fear or embarrassment of being caught.

While watching this young stud devour my wife with his eyes - and no doubt fueled by the alcohol - my horny imagination quickly took over. I began fantasizing about my wife getting up, removing her bikini and walking over to kneel in front of him and start sucking on his huge dick. As these images flooded my mind, my own dick suddenly got harder and faster than it had in a very long time and I realized that I had to go away to masturbate or else go insane. I quickly pounded back my drink and started looking for an escape. Even with a small dick, I knew my hard-on would be noticeable with just my swim suit on but I made it safely to the nearest restroom. I went into one of the stalls, removed my suit and began furiously pounding my meat. In what seemed to be a matter of seconds, I was shooting cum out of my cock trying my best to aim it into the toilet bowl. I was panting hard and the orgasm which ripped through me was something I had not experienced in a long time. As I cleaned up the mess I had created, it suddenly hit me like a ton of bricks that what I really wanted was to watch that young man fuck my sexy wife. My cock remained just as hard as it had been before I shot my load. I sat down on the toilet seat shaking - trying to comprehend what I was thinking. I had often enjoyed reading letters by husbands who got off on watching their wives fuck other men but I never really thought of myself as one. Maybe it was just the sun and alcohol getting to me but I decided right then and there that not only would I allow this young stud to hit on my wife if he wanted to, I would work quietly behind the scenes to make it happen!

After quite some time, my cock began shrinking and I put my suit back on and headed back to the pool.

When I got back, Leslie was still lying on her stomach and I walked over and sat down. As I passed the young man, I nodded politely and he looked disappointed after I sat down beside her. Leslie turned over and asked me where I had disappeared to. I told her that I had gone back to our room to use the toilet. We chatted for awhile and she reapplied sunblock to her body. Out of the corner of my eye, I could see the guy eyeing my wife and smiled to myself that he had no idea how badly I wanted to see him fuck her. Leslie settled back in her recliner and closed her eyes. I started trying to make eye contact with the guy and finally succeeded. I smiled and said hello and asked him where he was from. He replied that he was from Milan, Italy and that he had arrived the previous night. I introduced myself and asked him if he was alone. He replied that he was so I invited him to sit closer to us to which he readily did. He grabbed his things and sat in the chair to our left with me between him and Leslie. We shook hands and I introduced him to Leslie.

She sat up in her recliner and extended her hand out to him. He got up, walked around me and instead of shaking her hand, took it in his and kissed it and told her what a pleasure it was for him to meet such a beautiful woman. Leslie seemed a bit shocked and embarrassed but I wasn't sure if it was because of what he had said or done or whether she had noticed the huge bulge in his swimming trunks. Either way, she seemed genuinely charmed to meet him. We soon learned that his name was Sergio and that he was a junior investment broker. Eventually, we learned that he was 26 years old and that he had broken up with a longtime girlfriend not too long ago. In fact, they had originally planned to holiday there together. He turned out to be a decent guy and I felt very comfortable about letting him seduce Leslie if he chose to do so. I was intrigued by the thought of Leslie cheating on me behind my back and decided that I would not confess my fantasies to either one of them but would let things take their course (with me trying to make it happen as best I could).

During the course of the afternoon, I pointed out to him young, attractive women who were hanging around the pool kidding him to find himself a companion for his holiday. (What I was really doing of course was trying to get him good and horny). Leslie kept telling me to stop embarrassing him. He would just laugh and say the girl wasn't his type or whatever. I tried to make Leslie jealous by pointing out a young, attractive Asian woman strutting her stuff saying that I wouldn't mind going after her if I wasn't married. Sergio chided me saying I had a beautiful wife and I had no need for a young woman like that. Leslie pretended not to be bothered by my declaration, assuring me that the girl would not be interested in an "old fart" like myself. Secretly, I was hoping that it was pissing her off and making her feel insecure so that she might be more apt to have a fling with Sergio for the dual purpose of revenge and to reassure herself that she was still physically and sexually attractive to other men.

After awhile, Sergio decided to go into the pool to cool off. Leslie and I watched him swim around while taking in the sun and scenery. Sensing that Sergio's swim was almost over and that he was on his way out of the pool, I got up and pretended to adjust my lounge chair. I wanted Leslie to get a good look at his body without worrying about me catching her checking him out. As he climbed out of the water, I snuck a peek at him and saw that the bulge in his swimsuit was still impressive despite having been in the water. Leslie had a head-on view of his body as he toweled his face dry and her head did not turn the other way until he took the towel away from his face. I was very pleased she was checking him out and could feel my own prick beginning to harden again.

We chatted and lounged some more before calling it quits for the day. I invited Sergio to join us for dinner and he agreed. The three of us spent a pleasant evening eating, drinking and dancing. Since I'm not much of a dancer, I encouraged Sergio to take Leslie onto the dance floor more times than I did. They enjoyed dancing together and I noticed that they had their bodies pressed up against one another probably a little more often and closer than they should have. We retired for the evening and Leslie and I made love. I was really getting off on the fact that she was probably fantasizing about Sergio as my little 5" cock ploughed into her pussy. I came much sooner than I usually do which was good as I thought it might make Leslie sexually frustrated and more apt to fuck Sergio.

The next morning, Sergio joined us for breakfast. He asked me if I wanted to play a game of tennis after breakfast. As I had had more than enough sun the day before, I declined the offer. He then asked Leslie if she wanted to play and she said that she would love to. That surprised me as she's not much for sports and has very rarely played the game. She went back to our room to change and we all met up at the tennis court a short time later. She wore tight shorts and a halter-top that allowed her tits to bounce more than the tennis ball as she ran around the court. Sergio seemed to enjoy playing and it was no doubt my wife's body which was making it fun as her tennis skills were scarcely good enough to return the ball. I excused myself from court side to get a newspaper. When I returned to the court, I saw Sergio standing behind Leslie with his arms around her trying to teach her how to swing the racket properly. They seemed embarrassed I found them like that but I pretended not to care.

After an hour on the court, they joined me in the shade. I suggested to Leslie that we check out the little town nearby and asked Sergio if he wanted to come along. To my disappointment, he said that he preferred to spend the afternoon on the beach but would meet up with us again in the evening. Leslie and I then headed into town by taxi and checked out some souvenir and jewelry shops. I asked Leslie what she thought of our new "friend" and she said that she thought he was a great "kid." I suspected that she thought of him as more than a "kid" but I didn't pry her for more. We met up with Sergio again that evening but retired a little earlier than the night before as both of us were beginning to get sleepy.

The next day, the resort announced that there was a van available for those interested in a trip to a special secluded public beach. Sergio indicated that he wanted to go and asked us to join him. We readily agreed and Leslie changed into her one-piece swim suit as we planned to do some swimming. She looked just as hot in her one piece as she did in her other swim suits and judging by Sergio's eyes, he agreed with my assessment. The beach was located just a few miles from the resort and was quite expansive and uncrowded. About the only people there apart from our resort were people arriving on horseback from the stables which were located near our resort. The riders would come down along the beach until the point where a boulder-strewn hill ran down into the water forming a natural barrier. They would then turn around and head back the other way. We enjoyed the day swimming in the warm sea and sunning on the beach. Leslie and Sergio enjoyed discussing books as they both have a keen interest in reading. I, for the most part, just sat there in silence trying to keep my erection under control as the two of them continued their bonding.

Later in the afternoon, the three of us went back into the water and swam out quite a distance. Since I'm not a strong swimmer, I soon got tired of treading water and told them I was heading back in. To my surprise but delight, both of them said they were going to stay out a little longer so I headed back in alone. When I reached the shore and sat on the beach, I observed the two of them treading quite close to one another. Soon after, the resort employee came to tell me that it was time to go. I got Leslie and Sergio's attention and motioned for them to come back to shore. As they got close and stood up to wade in, I could see that Leslie's nipples were big and hard in spite of the warm sea water. Sergio also seemed to have been aroused and was doing his best to conceal a semi-hard-on with his hands. Not wanting to embarrass either one of them, I turned my back to them in order to gather our things up until they had both reached their towels and covered themselves up. I now knew that the sexual attraction between them was real and becoming more intense. All I had to do was give them the opportunity to be alone in order for the three of us to realize our respective fantasies.

As we rode back to the resort in the van, I began plotting on how I could do that and quickly came up with a plan. I asked Leslie if she wanted to do some horseback riding along the beach as she used to do a bit of riding when she was in college. She said it was a great idea and that we should do it the next day. I asked Sergio if he had ever ridden horses before and he said that he hadn't but would love to give it a try. That night, at the resort, the three of us partied and I deliberately drank a little more than usual so that I could excuse myself from the ride the next day on account of a hangover. I had come up with the idea that I would tell Leslie that I would instead go back to the little town to buy a ring for her as an anniversary gift thus giving them some private time together.

Sure enough, the following morning, I didn't feel or look very good and I told Leslie she and Sergio should go riding without me. She said she wasn't surprised I didn't feel well and that perhaps it was better that way as she could help Sergio learn the ropes of horseback riding. I then told her that I wanted to buy her a ring as a present. She replied that it wasn't necessary but threw her arms around me and kissed me telling me what a wonderful husband I was. I asked her for her wedding band so that I could pick out a ring that would go well with it. She gave the band to me and I was hoping that with it off of her finger, she might subconsciously feel less guilty about screwing Sergio. She put on a cotton/linen outfit which would be ideal for riding. I got ready too and gave her a kiss goodbye and told her to enjoy herself and that I would be back late in the afternoon. I'm sure she had no idea of what I meant by a "good time." My plan was to go to the beach we had been to the previous day and hope that I could catch her and Sergio making out - or more!

I hired a taxi to take me to the beach and headed for the hill which formed the barrier down to the water's edge. I found a good vantage point which was shaded and settled down to wait for them to come. I was there for about a couple of hours and was beginning to think that maybe they wouldn't be coming at all. I got thinking that maybe they were already in Sergio's room going at it like a stallion and a mare in heat and that my fantasy of watching them would go uunfulfilled Eventually, I saw three horses coming down the beach and I cursed to myself that maybe they had picked up a riding companion and wouldn't be having sex on the beach after all. It turned out not to be them and I watched as the the riders neared and then turned around. As I watched them head back, the sky quickly clouded and then the rain starting coming down.

I really began cursing when the rain turned into a downpour but it ended almost as quickly as it began. Gradually, the rain stopped all together and I was sitting there soaked wondering what to do next. Then, all of a sudden, I saw two more horses coming my way and got very excited when I realized it was Leslie and Sergio. What excited me more than the sight of them coming was the fact that both of them were in swim suits. I wondered if Leslie had brought her bikini with her in her bag and had changed into it on account of the rain or to turn Sergio on. Whatever the reasons, my cock was rock hard as I watched the two of them ride toward me. Sergio seemed to be managing fairly well for a beginner on the horse he was riding.

I withdrew to a more secure spot as they drew almost within hearing range. They were riding along the water's edge as they reached the spot where the hill ran down into the sea. Curiously, I saw Sergio dismount from the horse and begin wading out around the boulders which were blocking the way. Leslie held his horse and waited. Within a few minutes, Sergio returned and motioned for Leslie to go into the water with the horses and go around the natural obstruction.

I quickly but quietly scrambled to the top when they disappeared from sight and saw them back on shore when I reached the top. On the other side of the hill, the expansive beach all but disappeared and I lost sight of them as soon as they reached the shade of the palm trees near the shore. I scrambled down the hill into the trees. Jogging slowly and quietly, I caught up to them just in time to watch them dismount from their horses. They no sooner had their horses tied up than Sergio grabbed my wife and pulled her close to him. My heart started pounding furiously as I watched him wrap his arms around her and she offered no resistance. They were soon locked in a deep kiss and embrace and I was mesmerized as I watched my wife willingly surrender herself to this young stallion of a man. Sergio began rubbing his hands over her back and then began squeezing and rubbing my wife's ample butt cheeks. The initial shock quickly abated and I took advantage of the situation to move in closer and conceal myself from their unsuspecting view. After a few minutes of nonstop kissing and caressing - my wife had begun to stroke Sergio's well-muscled chest, waist and thighs - Sergio reached behind and undid my wife's bikini top. With her top lying on the sand and her ample tits exposed, Sergio began cupping and caressing them and then wasted no time bending down to kiss and suck on them. My wife's head was tilted back and it rolled gently from side to side and I could tell that she was in heaven. Sergio's cock could no longer be contained and he had freed it from his trunks. It was sticking straight up out of his trunks easily reaching his abdomen.

I had never seen such an enormous cock in person in my life and couldn't believe something that big belonged on a man! My wife reached down with her one hand and began to stroke it. Sergio stopped sucking on her tits and stood straight up. My wife literally dropped to her knees in the sand and slid his trunks to the ground. He stepped out of them and kicked them off to the side while my wife took hold of his horse-sized dick with both of her hands and began sucking on the enormous head. His cock was very thick and must have easily been 10" long!! She then began sliding her mouth up and down the entire length of his prick before pulling away coughing and spitting. I wasn't sure what the problem was until I saw Sergio laugh, run over to the horses and return with a water canteen. He gave it to my wife who poured the water all over his dick and washed it clean. Presumably, the sea salt on Sergio's dick from wading in the sea must have made it difficult for my wife to suck. After cleaning it, my wife resumed stroking and sucking his penis while Sergio leaned back up against a tree and ran his fingers through my sexy wife's hair as she eagerly blew him.

She sucked and stroked him for several minutes and I figured that at his age he would soon be blowing his wad. By this time, I was beginning to go insane by the sight of my wife servicing another man with a huge dick and so I pulled my own dick out of my shorts. It was particularly exciting to see since it was only on rare occasions that my wife would do the same thing to me. I gave my cock a few quick pulls and it was soon spewing cum all over the sand. I had never been so excited in my entire life! As I regained my composure, I couldn't help but notice what a sexy couple they were. The sight of a young, single, well-built man and a sexy, older, married woman blowing on his huge cock made for quite a voyeuristic scene!!

But before he blew his wad either over my wife's body or down her throat, he said something to her and she stopped sucking. Pulling her up and leaning her far over to support her own weight against the trunk of the tree, Sergio pulled down my wife's bikini bottom to bare her beautiful big butt. He grabbed and rubbed her ass cheeks for a moment before giving her a playful slap on one of the butt cheeks. Leslie responded by spreading her legs while Sergio took his shaft and directed the head toward my wife's eager pussy and began rubbing her pussy lips with the head. He did this for a minute before pushing his cock a short way into her cunt. She let out a scream and I knew that she was in for the fucking of her life. Sergio started sucking and blowing air as he slowly began to push his cock into my wife. He slowly and carefully began to grind his monster cock deeper into my wife.

Leslie was screaming even though he only had about half of it in. He paused for a minute and then pulled back before pushing it in again. He was obviously trying to get her well-lubed and stretched in order to aaccommodate his entire length.

While I watched with a mixture of disbelief, excitement and a tinge of jealousy, my wife began urging him on screaming how good it felt to have a "horse dick" inside her. Sergio skillfully continued until it appeared from my vantage point that he had his cock completely buried inside my wife's pussy. I couldn't believe my wife could take in a cock that size but seeing was believing. Sergio developed a slow but steady rhythm which gradually picked up to a measured pace. My wife was screaming and moaning and groaning like I've never heard her before. As the pace picked up, Sergio began slapping and grabbing her ass cheeks and pulling on her hips while he pounded his dick forcefully into her cunt. After what seemed to be several minutes of steady pounding and grinding, Sergio let out a roar and began unloading his cum into my wife. I could only imagine the amount of cum that must have oozed from his balls up his long shaft and deep into my wife but the sight and the thought brought my own little cock out yet again to blow another load. I was now emotionally and physically drained and I sat down shaking on the sand trying to collect my wits.

Sergio removed his still-hard dick from my wife's cunt while she collapsed to her hands and knees on the sand breathing hard and moaning from the sheer excitement and pleasure of it all. Sergio gave a look around to see if they had been watched and luckily did not see me concealed by the foliage. He picked my wife up in his strong arms but she dropped down to her knees again to suck on his dick. I had never seen my wife act so brazen and cock-hungry but I could certainly understand why. She cleaned his cock good before getting up to put her bikini back on. Sergio's hard-on looked like it was not going to go soft anytime soon and he went to his saddlebag and pulled out a pair of pants. He returned to my wife and sat down on the sand. I decided to take the opportunity and make my escape since I figured their tryst was probably over for the time being.

I crept away still shaking with excitement from the experience. As I walked through the jungle back toward the road, I felt a whole gamut of emotions - joy, pain, triumph, guilt - you name it - but I regretted none of it! I was even pleased with myself that I had managed to manipulate events somewhat to make my fantasy a reality. For some reason it didn't bother me that my wife had just cheated on me. Perhaps it was because Sergio was nine years her junior and from another country with the likelihood of them meeting again remote. I was also confident that she was motivated by physical and sexual attraction rather than by feelings of love. It did suddenly dawn on me that they had had unprotected sex but I tried to reassure myself that Sergio was by in large a sensible and intelligent young man and that sticking his cock into a woman unprotected by a condom was a rare occurrence. Having had the opportunity to fuck a woman as sexy as my wife, I couldn't blame him for his lack of discretion. I also hoped Leslie too must have felt it was a safe gamble for unsafe sex. I finally made it out to the road and began walking in the direction of the resort. I flagged down a passing car and gave the man $20 to take me back to the resort. When I finally reached our room it was just past noon and I sat down on the bed and collected my thoughts. I reasoned that Leslie and Sergio would be coming back in an hour or so after returning the horses to the nearby stable and that they would probably pick up where they had left off sexually in Sergio's private little bungalow provided Leslie thought I was still in town shopping for a ring. I went and got something quick to eat at the restaurant and then picked a secluded part of the resort beach to wait and watch for their return. Eventually, the two of them came walking back together and I followed at a safe distance. They parted company with Leslie headed toward our room and Sergio toward his bungalow. I decided to hide outside Sergio's bungalow and hoped to be able to spy on my wife and Sergio in the privacy of his accommodations.

Fortunately, well-concealed by large plants and bushes, I was able to hide and spied my wife coming toward the bungalow within about 10 minutes. She had changed into the outfit I had seen her in when I had left that morning. She knocked on the door but immediately went inside. Due to the fact that the front window was not well-concealed, I couldn't take the chance of peering in. Instead, I knelt under the bathroom window which was situated too high for me to look into even if standing. I could hear their voices but was unable to hear clearly what they were saying. Soon I could hear the sound of the shower and both of their voices - i.e. moans and groans - coming out of the bathroom. The shower didn't last too long so I figured they must have soaped one another up quickly and then retired to the bedroom for a good "romp in the hay." Knowing that my wife enjoyed being on top, I imagined her riding her Italian stallion and him kneading her breasts and caressing her ass as she rode his impressive cock. In very little time, I could hear my wife screaming as she no doubt had his cock buried deep inside her pussy and presumably riding him hard and wild in a way we never could with my small dick. I was beginning to feel jealous and nervous so decided to go back to our room lest I be seen eavesdropping in the bushes. When I returned to our room, I tried masturbating but was unable to cum. No doubt at my age, I had already shot my quota earlier in the day.

Leslie returned to our room about two hours later. She seemed surprised to see me and a bit flustered. She asked me when I got back and I told her about 30 minutes ago. I asked about her ride and what she had been up to. She said the ride was very good but that she and Sergio were both sore - their bodies not being used to riding horses. I grinned to myself knowing that she had had quite a bit of meat between her legs that day - the horse's back and Sergio's cock - and that she wasn't really lying when she said she was sore! She then explained that Sergio had returned to his bungalow to soak in the tub and rest and that she had gone for a walk trying to prevent her muscles from tightening up. She then inquired about "the ring" but I told her I had given up after a long, fruitless search and that I would wait till we got back home to buy her one. I returned the wedding band and she gave me a big kiss and told me that she loved me very much. I told her that I loved her more than I ever had and could feel myself getting hard. I pushed her onto the bed wanting to stick my own cock into her and experience the feeling of sloppy seconds but she insisted she was too sore from riding the horse - and I knew exactly what she meant!

The remainder of our stay was uneventful and anti-climatic. Leslie and Sergio played it cool while we were together. I convinced Leslie to go to the resort's nude beach but that was not terribly exciting given the events I had witnessed earlier.

Sergio departed on the Thursday and Leslie gave him a big hug and kiss, told him to keep in touch and invited him to our home in upstate New York. He replied we could count on it and he gave my hand a firm and sincere handshake and invited us to Milan. On the following day, my wife and I checked out and flew back to New York.

It's been almost a month since our vacation and my wife hasn't shown any indication that she was unfaithful nor remorseful about it. I've quickly come to terms with her infidelity and my new status as a cuckold. Our sex life is now more exciting, my erections stronger and my interest in having sex with my wife more intense than it has in a long time. Every time we make love, my mind goes back to that Caribbean beach and the sight of my sexy wife getting it on with her young Italian lover with the big cock. I couldn't be happier!!

TheCuck