My wife, Laurie-Ann, and I were long overdue for a beach holiday. We had both been travelling extensively in recent months but mainly on business so we invariably returned home more tired than when we left. We needed to spend some time walking barefoot in the sand at the edge of the ocean, holding hands and watching the sunset. It was time to revisit the Caribbean, and an island resort in the Dominican was our destination of choice.
One of the great things about the Caribbean, apart from the crystal blue water and soft white sand is the relaxed attitude to women sunbathing topless, and Laurie-Ann has always taken full advantage of that. By the first day at the beach, she was already allowing the sun’s rays to tan her beautiful breasts. We had a semi-private cabana at the resort where she sunbathed wearing only a thong bottom. The cabana boy discreetly averted his gaze from her nearly naked body when he brought our drinks.
It occurred to me that she might have inadvertently caused the cabana boy to become a little aroused, and I asked whether she had observed him getting a slight bulge in the front of his uniform shorts. She remarked that she had noticed he was quite good-looking and athletic, however she was not in the habit of staring at a male server’s groin.
I asked whether she thought the cabana boy, being tall and muscular, might be unusually well endowed, observing that rumors about these Caribbean guys abounded. She replied that if she wanted to find out, she was quite capable of doing so, but had come to the Caribbean mainly for a rest.
My wife had suggested we take up the resort’s offer of a candlelit dinner for two on the beach at sunset but I had demurred as the cost was a bit pricey. I told her I would book it if she could get the cabana boy to show us his equipment. The following day, when the young man in question brought the drinks to our cabana, my wife whispered something to him, at which point he briefly lowered his shorts exposing his impressive manhood. They both laughed as she tipped him a fifty, and he was on his way. I seemed I was obliged to book the sunset dinner for two.
Though I conceded that she had won the contest, I told her I was reluctant to admit his superiority. She replied that it had been in the flaccid state and had it been tumescent, the sight of it would have been more than I could handle, although certainly not more than she could handle.
She had issued me a veiled challenge and I decided to call her bluff. She had only cuckolded me once and I was curious to see whether she could do it again, and whether my psyche could handle it.
I told her, “OK - let’s see if you can seduce him and we can all see what we are made of.”
“You’re on,” was her succinct reply.
In bed that night she held my erection and outlined her plan. In the early afternoon tomorrow, she would arrange with the management for our cabana boy to have a couple of hours for her exclusive attention and she would order a drink to be brought to our room. I would be at the pool initially. On his arrival, she would be out of view in the bathroom and call to him to put the drink on the bedside table. She would then emerge totally nude and tell him the management had given him a couple of yours off and ask him if he would like to join her in the shower. The idea was that I would return to the room and “catch” them in the shower, in flagrante delicto. I would assure the poor startled lad that everything was fine as I really didn’t mind her sucking his cock, and we would see were it went from there.
We had wonderful sex that night. She promptly fell asleep but I was surprised to find my erection soon coming returning. As I lay there, I wondered what I was getting myself into. I had only consented to her cuckolding me on one occasion and that had been because she had been pretty much a virgin when we married and I thought I owed it to her to sample another man’s cock at least once. Sex with a dark-skinned cabana boy was going to be rather different. The interracial element was not a huge deal for either of us. We view race as a social construct, however we both regard ourselves as high-flying professionals so the power dimension was huge. Additionally, although I had claimed otherwise, his penis was an order of magnitude larger than mine.
At lunch the next day, my wife seemed to be in excellent spirits and we didn’t discuss the event about to unfold. I was getting very nervous journeying into the twilight zone but it was too late to chicken out at this point. My wife went back to the room and I took off for the pool to wait. I was getting very apprehensive and ordered a stiff drink at the swim-up bar. Here was a guy who made two percent of my hourly charge-out rate and he was going to put the horns on me. There was even a good chance I would be rated second best after he had taken my wife to heights I had never taken her to. What had I done?
I watched from the pool as he entered our room and continued to wait with mounting angst. After five minutes, he was still in there. Five minutes became ten. It had been agreed I would give her fifteen minutes to work her magic but I was getting really worked up. I couldn’t stand it anymore and strode towards the room and let myself in quietly.
There was plenty of noise coming from the bathroom. They were in the shower and she was on her knees blowing him eagerly. He was startled when he saw me but I gave him a smile. She rose to her feet and led him out of the bathroom by the hand. She jumped onto the bed and spread her legs. The poor guy looked totally nonplussed but I handed him a condom at which point he began to get the ideal: in fact, he seized on it with gusto.
He was young but he knew exactly what to do. After briefly exploring her breasts, torso and thighs with his hands, he flipped her over and probed for her vagina with his penis. I was amazed how easily he was able to penetrate her. With his rigid cock inside her he started to pump her very gently. My feeling of jealousy rose to the level of insanity, but at the same time, I was seemingly paralyzed. I watched with surreal fascination as she responded with soft moans as his cock moved inside her. Their joint movement continued for many minutes. And her orgasm came suddenly with a massive crescendo. Anyone passing our room would have known that the female occupant had just enjoyed a massive climax. I stood, transfixed, not knowing how to react. My erection had hardened to the point of pain.
He wasn’t finished and turned her over into the missionary position. He probed her with his fingers to make sure she was still responsive and, having decided she was, he slipped his glistening rod into her holy-of-holies and repeated the process, this time at a faster rate. It didn’t take her long to come again and he released his load as soon as she had finished pulsating. Unable to control myself any longer, I lost my own load at about the same time. I guess I could claim the three of us came simultaneously.
He swiftly dressed and left with his drinks tray in hand having pocketed what I’m sure was the biggest tip he had ever received. Of course, I immediately asked her which cock she liked better. She didn’t give me a definitive answer but I rather got the impression he had the edge on me. She did say we were different but couldn’t say how, perhaps to preserve my ego.
We had only booked a week at the resort and our intimate encounter with the cabana boy was a one-shot deal. Will there be more well-endowed young men in her future (and in her vagina). I’m not sure yet but I’m resolved to be very careful who I go up against henceforth next time.
I met the young woman who would become my wife when she was in her sophomore year of an undergraduate degree in biochemistry. Ah, the heady days of academia. I noticed her eating alone in the student union building and occasionally made a point of saying “hello” without making my interest in her too obvious. I was eventually able to engage her in conversation and found her shy and bookish but gifted and curious about the world. Physically, I would describe her as slim, petite and pretty in a girl-next-door style.
I was a grad student and several years her senior. I eventually found the courage to ask her for a date but she brushed me off with the claim of being busy preparing for a mid-term. Things might have gone no further if I hadn’t met her on a bus a few days later. Happenstance is a curious thing. I rarely took the bus but I was travelling by motorcycle at the time (I still love bikes) and my machine was out of action on that fateful day.
She accepted my invitation to an evening out. I later discovered that she had had just broken up with her boyfriend due to his duplicity and was thus newly single. The date went well though she seemed a little nervous with me and I took her disapproving comment that guys always wanted sex right away as a subtle warning to take things slow.
She left campus during the summer semester but we kept in touch long-distance (this was before the days of Zoom) and resumed our relationship with more intensity in the fall. I had to admit to myself that I was falling in love with her but she was quite reticent around the subject of sex. I discovered she had had three previous boyfriends. Each of them had touched and fondled her in intimate places and she was familiar with more than one way to stress-relieve an erection, but curiously she had ever been allowed a penis to enter her vagina. I don’t know that she would have met everyone’s definition of a virgin but that was certainly how she seemed to me.
I proposed to her the following year and finally, during a short vacation in Myrtle Beach, she surrendered her maidenhood to me. We married shortly after her graduation and years of happy marriage ensued. At her request, we delayed starting a family for several years as she wanted to get established in her career but eventually, a daughter arrived, and three years later, a second.
ur relationship continued to be happy as, despite the challenges and tribulations of parenthood, we adjusted to family life. She became progressively less inhibited about sex and, although our sex life would be considered “vanilla” by many modern people, we had sex in some interesting places outdoors and she was confident enough to sunbathe topless when we vacationed in France.
I asked her if it bothered her that I was the only person with whom she had performed the sex act. After thinking about it for a while, she replied, “Not really”, which I thought was rather non-committal. She was aware that I had had a number of intimate girlfriends before I met her and she told me I was fortunate to have sown so many wild oats. I told her that if it did bother her that I had been her only one, we could work something out as I had always been curious about what she would be like with another guy.
A month or two later, she told me during foreplay, that it did trouble her that I had been her only lover, and asked whether I was really serious about letting someone else have sex with her. She was open to ideas and had often wondered what another guy would feel like moving inside her but was unsure how infidelity might affect our relationship. I told her that it would make me insanely jealous but, provided we were both assured it could happen safely, I felt I owed it to her. In all honesty, I found the prospect intensely exciting, but I wanted to keep it about her rather than me. I very much wanted it to happen but did not want her to feel I was pushing her into it. I did tell her that I had read in a respected psychology journal that fifteen percent of adult males harbored the fantasy of watching their wife have sex with someone else and that about half of these had acted on it.
We talked about the possibility in the abstract at some length but didn’t get around to doing any serious planning for some time. When she was definitely sure she wanted to go ahead, we agreed to discuss the details seriously over a restaurant dinner. I was surprised to find she had given a lot of thought to how she wanted it to happen.
She would be the one to choose the lucky guy and he would need to be someone we knew and trusted; not someone we picked off the internet.
She would want me to be close by during encounter but for me to take no part in it (which was all fine by me). She would want it to happen in a classy hotel room and not at home.
She would set the boundaries in advance on what he would do with her and what he expected her to do to him (which sounded reasonable enough).
She even had someone in mind for the encounter; a male friend of her best girl friend whom she found attractive. She asked me to make the approach to him so that he appreciated my feelings and understood she was looking for a one-time sensual experience rather than an affair.
Everything looked really promising, however the thought did occur to me that the guy under consideration might, in the event, disclose some salacious details to my wife’s BGF (who was not good at keeping secrets) and it might become common knowledge that I was a willing cuckold. I decided that was a small price pay for what would be achieved and invited my wife’s prospect to meet me for a drink. If he was surprised that I was inviting him to have sex with my wife, he didn’t show it. I explained everything to him as best I could, and my wife joined us later to assure him that we were quite serious about the invitation and keen for it to happen. I had confessed to my wife that this had long been my fervent desire but didn’t let him know just how keen I really was.
The organizational details, time, place and safe-word were mutually agreed which unfortunately required me to endure an agonizing week of anticipation. My wife and I made love every day and each time was hot indeed. At no time did she need to ask me whether I was going to change my mind and withdraw my consent and we didn’t discuss the upcoming event at all.
Everything seemed to be going well until twenty-four hours before the planned get-together. My wife experienced what might be described as a failure of nerve.
As we were about to go to bed, my wife suddenly became withdrawn and had no desire to make love. She asked me if I had fully thought through the ramifications of what we were about to do, and could I really remain disengaged as I watched another man’s cock go into her. I told her it wouldn’t know how I would respond until the moment, but it was something I felt I had to let happen, for both our sakes. We both slept fitfully that night.
The momentous day finally arrived. We enjoyed a relaxed dinner and drinks in the hotel before adjourning to the room for the night (two double beds – one for them or them, one for me). I managed to stay fairly calm and my wife seemed remarkedly self-assured. Up in the room, with both of them now nude, she seemed less confident and unsure of how things should start. My first (and only) contribution to the proceedings was to suggest to him that he start by giving her a gentle massage.
She lay face down on the bed and he commenced to do so and she soon seemed to relax. As she rolled over, I could see her nipples were hard, and she touched his erection tentatively, giving me a sideways look of concern as she did so. I gave her a reassuring smile. He had also noticed her nipples and he took each of them in his mouth in turn. Being fairly small-breasted her nipples are very sensitive and they both enjoyed the attention he gave them. I observed that his penis was curved and circumcised, and it occurred to me that this was the moment of truth; the point when my wife found out what another man’s cock felt like in her wet and willing pussy.
He wasn’t in a rush. He opened her legs and then her labia in order to apply his tongue to her clitoris. She really enjoyed that and he soon had her moaning. He may have felt no urgency but I was frantic to see him penetrate her. He finally did so and I was surprised how easily he slid it in causing her to gasp for breath. As he pumped her slowly and rhythmically, I could see her smile. She came in less than a minute, letting out a muffled scream as she did do, her toes curling and her fingernails clawing his back.
He wasn’t finished and he continued to pound her for several minutes until she came a second time, at which point he shot his sperm into her with a series of guttural grunts (please note that it was her request that he go in bareback as, if she was going to do it, she wanted to experience it fully – consequently the health safety aspects had been covered in advance). I had been unable to contain myself after her first orgasm and relieved myself at that point.
They rolled apart and I watched the white fluid leak out of her. To my surprise, my wife burst into uncontrollable sobbing. Tears cascaded down her face and over her breasts.
“I’m sorry darling, so sorry,” was all she could say. I assured her neither of us had anything to be sorry about. It had been the second most intense moment of my life (the first having been when I popped her cherry years before). Our male guest stayed through the rest of the weekend and the two of them had sex too many times to count. We haven’t seen him since, but if she ever needs a reminder of what another man’s cock feels like, she has his number and is welcome to call him.
