The holiday started as any ordinary holiday did. It was mid-afternoon on a warm summer day up on the Coast. The beach looked terrific and was absolutely packed with tourists. Win (Winona, my wife) and I (Keiran), dropped our bags off at the room, changed into our swimming attire and headed for the resort’s pool. The pool was one of those that had several beach entrances and a swim up bar: Just our kind of place.
Win is in her early 50s with the body of a woman half her age; she has long sandy blonde hair, a trim athletic figure, tight arse, and pert breasts that round out a sexy body. She exercises regularly, putting me to shame, and has good tone and cardio fitness. I would say she gets her fair distribute of looks from men of all ages, and even some jealous women. I had been carrying a bit of weight over the years after slowing down with exercise, so I worked hard to lose weight over the winter to impress Win, and come summer, I was looking particularly fit.
Down by the pool area there were the standard family groups coming and going, and a small group of men in their late 20’s to early 30’s who looked like they had had a few drinks but were not rowdy or causing trouble. They were either sitting or standing around in their speedos and looked like lifeguards with their toned arms, blonde hair, and abs that you could wash your clothes on. One blonde haired guy even had those muscles that extend down from the stomach to the groin area. Not over muscled, but particularly toned. He had a good tan like the others but seemed quieter than the rest and from the look of it, he didn’t need their bluster. His budgie smugglers seemed to strain from what was, evidently, more than a budgie.
I asked Win, “Did you see the birdlife he was hiding?”
Win laughed and said, “No, I most certainly did not.”
I knew she had seen because she had given him a quick second glance as we walked by. Win went over to check the water and proceeded to take her sarong off and walk over to the pool, her breasts sat high and proud, and her one-piece bathers had crept up her backside revealing firm, well rounded cheeks.
As she bent over on all fours to feel the water, I noticed the group of guys begin to talk quietly and look in my wife’s direction; They didn’t know I was watching because of my sunglasses. Looking at Win’s backside gave me a tingle in my groin. I could see the gorgeous mound between her legs as she bent over to touch the sparkling water, and so could the guys. What a sight.
Win decided to go for a dip, suggesting that I should join her.
I said, “Maybe later.”
I really wanted to watch the reaction from the guys.
She walked into the beach entry of the pool and did a few laps before coming to a stop at the opposite side. She climbed up the stairs and walked the long way around the pool, deliberately passing the group of men. I noticed that from the frog kick she did in the pool, the crutch of her swimsuit had ridden right up between her luscious lips, leaving nothing to the imagination.
The guys were talking quietly again and the blonde with the strain in his smugglers had to adjust himself and place a cap over his crutch area. It seemed I wasn’t the only one turned on by my wife, who pretended not to notice, but I could tell from the set of her head that she was enjoying the looks she was getting.
We sat by the pool for a while then decided to head over to the pool bar for some refreshments. Mojitos were on the list so we order some, laid back on the sun lounges and quickly devoured the first round.
When I went back to the bar to get some more, I noticed the young blonde guy who had taken a good look at Win, standing in line at the bar waiting to buy a drink so I got to talking to him as we waited. He told me that he and his friends were having a reunion and they were heading out clubbing later that night, but he wasn’t all that interested. I told him we were up on holidays for a week or so and would be hanging around the resort that afternoon as they had some good live music coming on later. I introduced myself and he told me his name was Tristan. We got our drinks and headed back to our own areas.
After the second round of mojitos Win started to fall asleep.
As I watched the other guest come and go, I noticed through my sunglasses that Tristan was looking in our direction. I stole a glance at Win and noticed that as she slept her legs had parted slightly and they were aimed directly towards Tristan. I saw him adjusting position uncomfortably on his seat, but his eyes refused to budge from my wife.
I started getting aroused thinking about another man looking at my wife with the same desire I felt. I think a lot of men feel a sense of pride knowing that other men discover their partner attractive. My mind started to wander about the possibilities. After another 20 minutes Win woke up and said she wanted to head up for a shower and get ready for the afternoon’s music and dinner.
An hour later we had showered and dressed in casual clothes for the festivities and were both raring to get back down to the entertainment. I had shorts and a polo on while Win had a lovely, floral, sleeveless, thigh length loose flowing dress that set off her figure. The type that when she sat with her arms down you could see in the sides and catch a look at her bra. On this occasion though, she wasn’t wearing a bra and as she sat at our table waiting to leave, I could see a gorgeous side on view of part of her breast; the nipple was still hidden by the angle, but I could definitely see the milky curve of her gorgeous breast.
You could see how pert they were, and I started to get hard again.
I smiled inside knowing how she was gonna drive all the men crazy tonight.
As Win walked ahead of me to the lift I noticed there was no bikini line from her panties; I thought if she was wearing a G-string? This was driving me crazy!
We entered the bar and sat at a high table with stools, the only remaining seats, over to one side of the stage and had a good view of the stage and the rest of the crowd. The crowd were talking loudly and after a few drinks looked energised and having way too much fun. After a few minutes I noticed Tristan sitting with his mates at a low table that was in a sunken area just below ours that happened to be looking straight in our direction.
Coincidence? I didn’t think so.
But then again, we did come in after them.
I got up to get some pinot gris for us and noticed from the bar that Tristan was looking intently over toward our seats. I looked toward Win who was observing the band in the process of setting up.
At this point I noticed she was sitting forward on the edge of her seat and her legs were slightly aside. When I had our drinks, I walked slowly back to our seats but took a path that would show me what Tristan could see. Tristan quickly looked away when I neared his group to say hello.
I had a brief chat and turned toward our table nearly dropping our drinks when I saw what had caught his eye. I found I could make out my wife’s gorgeous flower looking at me from this lower vantage point. She wasn’t wearing panties!
I’m not sure if she knew what he could see, but God, what a turn on knowing that Tristan could see this gorgeous view.
I was sure from the angle that only he could see. I went back to Win and sat with the drinks, saying nothing. From the corner of my eye, I saw Tristan constantly stealing glimpses but none of his mates looked in our direction. He was keeping this his little secret.
Dinner came and went, the music was great, and everyone was getting very tipsy and ready to party. The dance floor was crowded, with no room to move. We danced as hard as the other guests and now and again I noticed people would sometimes bump or rub up against Win from behind. At one point she lost her balance and went backward slightly and fell against Tristan, who had been dancing to the side and behind her for some time.
I guessed he was trying to get a good look through the sleeves of the dress while off to the side. On this occasion when she fell back there was a slight pause before she moved off him and I noticed he had a considerable bulge in his shorts.
A few more drinks and then the music was pumping; there was hardly room to move. I was standing against and in front of Win, Tristan was behind at a minimal distance although the throng of the crowd made it hard to keep aside. There was a strong scent of perfume, cologne and sweat.
A surge from the crowd and Tristan was now pressed up against my wife from behind; she was smiling deviously.
I said, “If you liked that, how about this?”
I pushed up against her from the front moving her hard up against Tristan.
She laughed and said, “I’m thoroughly enjoying it.”
Tristan was definitely smiling now, and we all laughed at the impossibility of any real movement on the dance floor.
Tristan said, “It’s like dirty dancing.”
He then moved his hands to Win’s shoulders and slowly moved them down her sides to her hips and held on tight as the two of them started to swing their hips back and forth against me, which in turn pushed me against the people behind me. We were having a ball and Win was having quite a bit more, it seemed.
Another hour passed and Tristan’s mates said they were leaving to chase the girls up at a night club. He told them he wasn’t that keen and was gonna have a few more drinks then go to watch a movie in his room.
After they had left, we suggested he come up and have a few drinks with us and we could play cards, watch a movie, or whatever. He said thanks, that would be great, but he wanted to go to his room and shower first. Sounds like a plan, we agreed, and we went back to our room to await our guest.
Win said that she was gonna shower too, and I said I’d join her. When we got to the shower, I kissed my wife hard on the lips and told her how hot she was. I told her she had been making me horny since the pool that afternoon. I’m a naturally horny guy so it wasn’t hard but today was extra special.
I reached down between her legs to discover she was very, very wet. She said she had been so horny all afternoon after the pool, and the dancing just topped it off. I told her that I was glad she was horny and that I wanted to make her happy. I wanted to please her in any way, physically, emotionally, and sexually. As long as she was comfortable and happy, she could have what she wanted, within my power and limited finances to give.
She laughed, gave my cock a squeeze and rub saying, “Hmmmm, I hope you’re ready for me to hold you to that promise? Now shower before Tristan gets here or it could be awkward.”
She laughed and we proceeded to shower and dress before our guest arrived. Win appeared in a long flowing white skirt and tight t-shirt with no bra underneath. I was just in my favourite shorts and a t-shirt. We were both feeling relaxed yet there was a buzz in the air.
We put on some relaxing music, turned the lights down a bit and poured a couple of drinks. Before we knew it there was a knock at the door and Tristan came in wearing a pair of those happy pants from the 80’s and an Australian Crawl t-shirt. Cool guy I wondered. I poured him a drink and before you knew it, we had been talking and laughing for an hour or more, and quite a few drinks had been devoured. I asked what they wanted to do, and they all agreed to play a game. We tossed around a few ideas and settled on truth or dare. Win looked pretty pleased; like she had manipulated us boys into this particular game. I was excited that she was taking control and wanted to see where this would lead.
We threw the dice to see who would go first and it landed on Tristan. Who would he choose and what would he ask?
He looked at Win and said, “Truth or dare?”
Win replied, “Truth.”
He then asked, “Did you like all the dancing tonight?”
She replied with a smile, “Yes, I most certainly did.”
It was now my turn and I asked Tristan, “truth or dare Tristan?”
He replied, “truth.”
Damn! I was hoping to see some flesh.
I asked Tristan, “Although it was uncomfortable and crowded, did you like dancing behind my wife?”
He dropped his eyes and went a bit red (shy hey) and replied, “I enjoyed it immensely.”
Win smiled at this.
Next it was Win’s turn to ask.
She turned to me and said, “Truth or dare?”
I replied, “Truth.” I was going at their pace.
She asked me, “Were you sincere with what you said in the shower in terms of making me happy and giving me anything I want?”
I said, “Yes, whatever you want!”
It was back to Tristan and he asked Win again, “Truth or dare?”
She replied, “Dare.”
His face lit up, and so did mine.
He said, “Before I give you my dare, we’re all adults here, is anything off the table?”
We replied, “No.”
He then turned back to Win and said, “I want you to go over to your husband, take out his cock and put it in your mouth.”
Win stopped, looked at me (I smiled) and said, “I’d love to.”
She walked over to me, pulled down my shorts and took out my cock, licking from my balls to the head of my now semi-hard shaft; She took me in her warm inviting mouth and as she bent over her skirt rode up giving Tristan a close-up view of her mound. This was gonna be an extremely erotic night.
It was now my turn.
I asked Tristan, “Truth or dare.” He replied with, “Truth.”
I asked, “Would you like to watch me and Win have sex?”
He blushed again and said, “Yes please!”
Win asked me, “Truth or dare?” I took a dare.
She said, “Come over between my legs and lick this sweet pussy through my panties.”
I did as she asked, licking the full length of her pussy lips and placing my thumb against her arsehole; She likes this. I could smell her wetness. She shook and took a heavy breath when I pulled away. Her pupils were wide.
Tristan then asked Win, “Truth or dare?”
She replied, “Truth.”
He asked, “Have you ever been with another man or seen another man’s cock?”
She replied, “No I haven’t. But I would like to!” I was getting hard.
Back to me.
I asked Tristan, “Truth or dare?”
He replied, “Dare.”
I said, “I guess you’re going to be the first. Stand up, pull your pants down and show Win your what you’ve got. She’s been wet all afternoon thinking about you.”
Given his budgie smugglers from earlier I knew he would have an abundant length of cock and large balls. He smiled, took down his pants revealing a semi-rigid shaft that was straight and long. The head of his member was a large mushroom that looked straight at my wife. The summer heat allowed his balls to hang a bit lower and his shaft began to grow as he saw my wife staring at it.
“Can I touch it?” she asked.
I didn’t know if she was talking to him or me, but with both answered, “Yes!” at the same time.
Win moved forward and took his long semi-hard cock in one hand and supported his balls in the other.
She looked at me and said, “You said whatever makes me happy right?”
I smiled and nodded but was nearly bursting in my pants watching my wife with another man’s cock in her hands. It was so erotic.
I moved behind and could see that her panties had a large wet patch on them and knew she was very horny. I touched her pussy and she jumped.
“Sorry, I was busy looking at Tris and didn’t see you moving behind me,” she said.
I told her, “If it’s ok with Tris, you can do what you want with him.”
He smiled and said, “Yes please. I’ve been admiring your hot figure all day and tonight’s conversation and friendship makes me want you all the more Win.”
She bent forward and kissed the head of his cock and he sighed. She then moved down and licked from his balls up the shaft of his large, now engorged head, and teased under it with her tongue. He was a good inch longer than me and the girth was slightly larger. Before our very eyes his cock grew longer and harder. By this time I was rubbing Win through her panties and she was moving on my hand.
I asked Tris, “Would you like to change places?”
He said, “Gladly.”
Win then laid back on the floor as Tris moved between her legs.
He bent over removing her skirt and top then leaned forward to kiss her ear lobe asking, “Is this ok.”
She moaned through a slightly opened mouth, “Yes.”
He looked at me and I just nodded and smiled. He kissed his way down her body, touching and feeling with his hands. Everywhere he touched she flinched as if his hands were fire. He kissed his way down to her panties then lifted her legs in the air, removed her panties and bent down to smell her musk. I watched as my wife was about to be eaten by another man.
My cock was rigid and so was his. It had hardened even further after smelling her wetness. He held her legs in the air and placed the fullness of his tongue on her cunt. Win nearly exploded then and there. She grabbed the back of his head and thrust it between her legs. He licked and sucked like there was no tomorrow.
When she had cum he knelt back, revealing his long straight shaft that was glistening with pre-cum.
Win looked at me and I asked gently, “What would you like to do with that beautiful young cock there?”
She said, “I want to feel it in me! I want to feel that beautiful head slide all the way in. I want his shaft in my cunt! I want to feel his balls on my arse.”
“Well,” I said, “We’ve gone this far, and as long as everyone is happy and having fun, it’s totally up to you. Let’s enjoy ourselves tonight.”
I sat to the side where I could watch the action and Win could grab my cock if she wanted to. I watched as Tris slowly guided the head of his cock between the lips of my wife’s cunt. He slid it up and down then ever so slowly, he slid into her warm folds.
Win gasped, “Oh!” as his manhood slid in, and in, and in.
She grabbed my cock and started to stroke it as she breathed heavily. Tris started to slide in and out, ever so slowly, as I reached down and started to rub Win’s clit.
Win was in heaven with this young stud starting to increase the speed and power of his thrusts; her hand was stroking my cock in time with Tris’s thrusting. He leaned down and kissed her, their tongues entwined in a dance of their own.
Win started to cum, her pussy tightening as she moaned, “Oh, oh, oh, please fuck me.”
Tris was breathing hard and pumping harder.
Win cried out, “Yes, yes, yes,” as Tristan’s cock exploded inside her. He pumped and pumped and pumped until he was empty.
He leant down toward Win and softly kissed her on the lips, and she returned the kiss with a passion I hadn’t seen for quite some time.
As a result of the kissing, Tristan was soon hard again, and Win screamed with delight as she felt him grow inside her. They’d stopped kissing now but the sight of Tris inside Win was too much to bear and I exploded all across her breasts. I sat back and watched for the next 15 minutes as they repeated their act with increased fervour.
I didn’t know how exciting watching my wife could be. My cock was now hard again so I walked over and Win took me in her warm mouth. She was licking and sucking on my cock as Tris rubbed her clit and thrust into her warm, wet, cunt.
I came again on Win’s chest. With Tris’s pumping and rubbing she was moaning in ecstasy again, and I watched as his massive balls slapped against her arse: They started to pulse as he pumped his hot seed inside her. She moaned with pleasure and slumped against the floor, spent. We all laid back for a rest.
We took turns having showers and sat back talking with a few more drinks before Tristan said he should probably get going. We discussed whether Tristan would be keen to meet up again, to which he agreed, and then said our goodnights.
As we closed the door I turned to Win and said, “Next, it’s my turn…..”