My wife Paige had fantasized about having a threesome with two men since before I knew her. Being open-minded sexually and secure in our marriage, I didn’t feel threatened by her fantasy, and although I wasn’t sure how I’d feel seeing her have sex with another man (one never does), I found the notion arousing and therefore was open to the idea. Quite honestly, I never thought we’d actually act on it anyway. That is, until we met Matt while vacationing in St Thomas earlier this year.  

I was sick with the flu the week leading up to our vacation, and wasn’t one hundred percent when we arrived, but felt much better after a couple of days on the island. Needless to say, sex was off the radar for about ten days, but that would actually serve as a benefit to us. 

We passed by Matt a number of times during the first few days of our stay. I didn’t pay him much mind, but I caught Paige eyeing him from afar, which was understandable; he was an attractive man, slim with deep blue eyes and sported a moustache and well-trimmed goatee. He looked to be around our age, mid-forties, and his full head of salt and pepper hair complemented his tanned face; yeah, he was good looking.

It was our fourth evening at the resort, and we were having a cocktail on the patio before dinner. Paige looked beautiful, dressed in a short, slinky pale green haltered sundress with spaghetti tie straps. The straps draped over her delicate shoulders and her long brown hair was tied in a ponytail, her light brown highlights shimmering in the setting sun.  

Matt sat alone at the tiki bar sipping a cocktail and watching TV. He was wearing an off-white short sleeve linen button-down shirt and navy-blue khaki shorts. As we sipped our cocktails Paige occasionally turned toward the bar, obviously seeking to steal a glance at Matt. I knew what she was thinking, so I encouraged her to introduce herself.

“What are you looking at?" I asked.

“What. Me? Nothing.”

“Oh, come on. You keep looking at that guy sitting at the bar. If you like what you see, why don’t you don’t just go up to him and introduce yourself?”

“And say what?"

“Order a drink and say hi. See what’s how he responds. I know how I’d respond if you came up to me looking as pretty as you do,” I said with a big smile. “Go ahead.”

“And you’re good with this?”

“Yeah. You have nothing to lose. I’ll be watching from here.”

Paige stood and tossed me a sly wink as she strolled to the bar. Standing beside Matt, she motioned to the bartender, trying to catch his attention so she could order a drink. Matt turned and faced her, and I saw her smile at him. Her lips moved as she began a conversation, and a few moments later they shook hands, confirming that introductions were made.

When the bartender arrived, Paige ordered her drink then, glancing at Matt’s nearly empty cocktail, motioned to the bartender, pointing toward his glass. The bartender brought him another drink. Hmm. That’s interesting, Paige buying him a drink, I thought.

Paige and Matt were engaged in conversation for about ten minutes when I saw Paige pointing my way. Matt turned his head and waved, then followed Paige to our table.

“Honey, this is Matt,” Paige said.

I stood to greet our new friend. “Hi Matt. I’m Lee.”

“Lee, nice to meet you,” Matt replied with a British accent.

“Matt was just telling me that he’s here alone, so I invited him to join us,” Paige said.

“I hope I’m not intruding?” Matt asked.

“Of course not. Grab a seat and join us, Matt,” I suggested.

“Thanks,” Matt said.

Paige took her seat across Matt.

“Matt was telling me he is vacationing here, oh, let me correct myself, he’s on holiday here,” Paige said with a chuckle.

“Holiday, yeah. I’m here for two weeks. Got here last week. It’s my first holiday in a few years,” Matt replied.

Over dinner we learned that Matt was a widower whose wife passed away some years ago. After her untimely death he threw himself into his work as an Investment Advisor, often putting in twelve hour days, seven days a week. The relentless pace helped him double his client base and build a highly successful business; however, it came with a price.

“I was working myself to death, so about a year ago I hired three Investment Advisor Representatives for support. Doing so allowed me to reduce my workload,” he said. “And at the urging of my friends and family, I decided to take a long overdue vacation, leading me here.”

“Well, St Thomas is great choice,” I said.

“Yes, it is. Just beautiful,” Matt replied.

Our dinner conversation was engaging, and we talked about a myriad of topics. When the bill arrived, Matt insisted on treating us to dinner as a thank you for our hospitality. He then bought us a nightcap at the bar where he mentioned his desire to go deep sea fishing. 

“We’re going out tomorrow morning on a private charter. Why don’t you join us?" I asked.

“Really? I don’t want to intrude on your expedition,” he replied.

“Nonsense, definitely come along. We’ll have fun. It’s just us on the boat so adding one more shouldn’t be a problem. When we booked the charter the captain mentioned if we wanted to bring others to feel free to do so because there would be plenty of room. We leave at eight am so meet us in the lobby around seven-thirty,” I said. 

“OK. That sounds great! I’ll see you then!"

As soon as we got back to our villa Paige immediately asked me what I thought of him.

“Boy, the door didn’t even close yet,” I said jokingly. “Yeah. I like him. He seems like a nice guy,” I said. “The real question is how do you feel about him?”

Paige didn’t hold back. “Yeah. I like him too. I like him a lot but I’m disappointed.”

“How so?" I asked.

“I was hoping he’d end up here with us tonight.”

“I thought that’s what you were thinking. If that’s what you want, then you may need to flirt with him a little to see how he responds. You know, test the waters.”

“Yeah. I can do that. Are you sure you’re ok with this?”

“Yeah. This may be the opportunity we’ve been talking about, so yeah, I’m perfectly fine.”

Now, over the years Paige and I had talked about having a threesome an uncountable number of times, most recently before we left for St Thomas. She said that she was thinking more about it and a vacation would be the perfect scenario to have a threesome. She said if we ever were to include a third it needed to be with someone she’d never see again; she didn’t want the embarrassment of accidentally bumping into him somewhere. Well, here we were in St. Thomas, and in this case, with Matt living in London, the conditions were perfect.

The next morning when we arrived at the lobby we found Matt waiting for us. I called an Uber and Matt rode with us to the marina. After boarding the boat, we spent four hours fishing and had a decent outing. The weather was great and I caught two good sized snappers. Paige managed to reel in a yellowtail keeper, but Matt outdid us both, catching two yellowtails and two snappers, all keepers.

Back at the resort, Matt and I grilled the fish which the three of us ate for lunch. Matt thanked us again for allowing him to join us and offered to treat us to dinner again as a thank you for the gesture. We graciously accepted, and he suggested a seafood restaurant in Red Hook. We decided to meet him in the lobby at six-thirty, then we retired to our villa for a short nap before preparing for dinner.

We both woke around five o’clock. Page showered first. Using a brand-new razor, she shaved her legs and between them, leaving a small, well-trimmed triangle of pubic hair. I jumped in the shower while Paige blow dried her hair. Fumbling with a few different hair styles, she settled on putting it up in a bun. The topknot and wispy tendrils provided a casual look and a sexy aura. She clearly hit the mark!

Paige scoured the closet, deciding what to wear, when she settled on a cute powder blue mini sundress. The sundress featured halter straps that tied in the back, and since the fabric was double layered Paige didn’t need to wear a bra. It was perfect for a warm evening in the tropics. White sandals added a nice touch, as did a gold necklace and bracelet plus her favorite two-toned Seiko watch. She looked beautiful.

My attire was simple, a white polo shirt with blue shorts and sandals. Nothing fancy.

“You look amazing,” I said to Paige.

“Thank you!”

“I think I want you all to myself tonight,” I said jokingly.

“Well, we’ll see about that,” she replied with a big smile.

“Would that be so bad?” I asked.   

“Of course not, but I’d rather, well, you know, if I have my druthers.”

I smiled and kissed her on the cheek.

“Let’s see where the evening takes us. I’ll follow your lead,” I told her.

We arrived a few minutes early and found Matt already in the lobby.

“Ready, guys?” he asked.

“Yeah. I’m starving,” Paige answered.

“Good. And may I say that you look lovely tonight, Paige,” Matt said.

“Well thank you, Matt. You look nice yourself. I like the tropical shirt you’re wearing.”

Matt ordered an Uber and we were off to Red Hook. I purposely had Paige sit in the back with Matt while I sat in the front for our fifteen-minute ride.

“I think you’ll like this restaurant. I ate here a couple nights ago. It was really good,” Matt said.

“I’m sure we will,” Paige answered.

Paige and Matt talked about the fishing trip and the fun they had, and before we knew it, we were at the restaurant. We walked in and were greeted by the hostess.

“We have a table for three at seven,” Matt said to the pretty hostess.

“Yes Mr. Miller, table for three. Please follow me,” the hostess replied as she led us to our table.

Matt was right about the food. Everything was delicious and the conversation was lively. We talked a lot about the island since we had been here several times, giving Matt an education about the different areas of St Thomas and some of its history. We also talked about our occupations, Paige as a registered nurse and me as an electrical engineer. The conversation flowed smoothly.

I took the liberty of ordering the Uber this time, and like our trip to the restaurant, I made sure Paige and Matt were seated in the back. When we arrived at the resort, Matt suggested cocktails at the tiki bar. Of course, we were all too happy to accompany him.

We sat at the bar for a couple of hours, drinking tequila shots and enjoying the warm tropical breezes and flowing conversation. Paige’s inhibitions were beginning to wane, and soon she began flirting with Matt, sitting close to him, touching him whenever possible, and staring into his eyes. Her attraction to Matt was now obvious, and equally obvious was his attraction to Paige. And who wouldn’t be? She looked lovely and sexy.

Matt returned Paige’s innuendos with his own version which also included long stares and brief touches, particularly on her shoulders. I was perfectly fine with the exchanges and was actually becoming aroused watching them. It appeared everything was going according to plan, and the alcohol helped things move along.   

The weather began to turn as a storm was moving in from the ocean. The air was getting thick and flashes of bright lightening lit up the night sky over the ocean. By now it was getting close to eleven o’clock and the bartender told us he was getting ready to close the bar because of the incoming storm. A pretty tipsy Paige took advantage of the situation and suggested we go upstairs to our villa for a nightcap.

“We have some Patron upstairs. Come on up,” she said, staring into Matt’s eyes.

Matt was absolutely on board, so we settled the tab and staggered to the elevators. We rode to our floor, exited the elevator, and walked down the long corridor to our room. A quick wave of the keycard and we were inside our villa.

After dicing a couple of limes into quarters I grabbed the open bottle of Patron and poured out three shots. I walked into the living area and handed Paige and Matt their shots and a lime slice. Two shots later, I needed to use the restroom, so I left the room and relieved myself in the en-suite bathroom.

When I returned and re-entered the living area my heart skipped a beat. I stood frozen for a moment as Paige and Matt were engaged in a long, deep kiss. I felt my adrenaline flow and butterflies flying around in my stomach. I walked over to the sofa and sat beside Paige, who immediately slid her hand under my shorts in search of my cock. Matt looked my way, as if to get a read on my reaction, and I smiled and nodded, signaling my approval. Paige then brought her soft lips to mine, and we embraced in a sensual kiss.

I felt her lips tremble when we kissed, and realized Paige was clearly aroused that her long-awaited threesome fantasy was finally happening; she was going to be the center of attention between two men who wanted to please her, and I could only imagine how turned on she must have been. For my part, I was going to do my best to make sure the experience was as unforgettable as possible for her.

Oddly, the storm outside, with its loud thunder and bright lightning, created sort of a sexy ambiance in the background, adding to the eroticism as the three of us engaged in a series of back and forth, sensual foreplay of caressing and kissing. As lightning flashed in the background Paige’s soft tongue sought out mine, moaning in my mouth while Matt kissed the side of her neck. Paige turned and kissed Matt again as she stroked our semi-hard cocks through our pants.

Matt began unbuttoning Paige’s dress, and as he spread open her dress just enough to expose her pert breasts, Paige’s breathing grew heavier and more pronounced. Paige leaned her head back and closed her eyes while Matt and I glided our hands over her breasts, caressing and gently squeezing them. I tilted my head forward and took her right nipple into my mouth, sucking and gently swirling my tongue around it, alternating between left and right. The sensation of Matt's tongue exploring her mouth and my tongue gently grazing her nipples triggered Paige’s arousal to intensify to new heights, and sensing this, I decided it was time to move to the bedroom.

“I love you, Paige,” I whispered.

“I love you too, Lee” she replied as I took her by the hand and led her to the bedroom with Matt following close behind.

Once inside, we were greeted by our spacious king-sized bed. I threw the pillows and white comforter to the side, revealing a set of soft, crisp, white cotton sheets. Matt stood behind Paige and helped her out of her dress, and as flashes of lightning outside briefly illuminated the room, Matt untied the dress’s halter straps. Paige’s dress slid down her slender body and fell to the floor, and wiggling her feet and ankles, Paige stepped out of the dress.  Matt squatted behind Paige and removed her panties, slipping them down her shapely legs. Paige stepped out of them and turned and kissed Matt.

Matt placed Paige on the edge of the bed where she watched Matt and me undress. Any reservations I had about being naked in front of another man disappeared. All I could think about in this moment was Paige’s excitement of seeing two naked men with their erect cocks, there for her taking and her pleasure.

Paige fell to her knees in front of us just as a thunderous roar echoed, followed by two flashes of bright light. Undeterred, Paige wrapped her slender fingers around the base of Matt's cock; he was noticeably larger than me, probably about seven inches or so, with a thick, purple mushroom head. Matt placed his hands behind Paige’s head while she slowly licked his shaft. That was the moment that I realized I was perfectly okay watching my wife with another man. I felt no jealousy or anger or rage, just a feeling of extraordinary excitement and arousal.

I watched in earnest as Paige bathed Matt’s cock with her tongue, licking it up and down, leaving a trail of saliva behind with each wet lick. Cupping his balls in the palm of her hand, Paige took Matt’s swollen head between her lips and gently encircled it with her tongue. Slowly, she took more of his hard cock into her wet mouth, and I watched as she gradually and enthusiastically consumed more and more of it until nearly his entire cock disappeared. Matt began rocking back and forth, trying to fuck Paige’s mouth, but Paige, always the tease, released his cock and turned her attention to me.

I could feel Paige’s hot breath on my cock as she nuzzled her nose against me. Working her way down to my balls, she began licking that sensitive area between my balls and anus. Her tongue felt amazing! A few moments later she slid her lips up my shaft until she reached my head. Paige rotated her tongue around the tip before taking it into her mouth. She sucked me gently for a few minutes, then returned to Matt’s aching cock, licking his shaft again before wrapping her soft lips around it and taking it into her wet mouth.  

While sucking Matt, Paige reached between my legs and slid her fingers under my balls, cradling them as she engulfed Matt’s cock, bobbing her head up and down his long shaft. She expertly alternated between us, bringing each of us to the edge of orgasm, intuitively knowing just when to stop to prevent us from cumming, only to begin all over again, a talent learned from years of joyfully sucking cock.

While Paige was enjoying herself, she was ready for some pleasure of her own, so she begrudgingly abandoned our cocks and lay on the edge of the bed. She spread her legs wide apart, and Matt, needing no further encouragement, knelt between Paige’s legs and buried his face in my wife’s wet pussy. I lay beside her and began licking her nipples while Matt's tongue danced rhythmically across her folds. Paige’s breathing became heavy again, and once Matt’s tongue found her clit, he licked it feverishly, sending wonderful pre-orgasmic sensations through her body.

“Yes, that’s it. Lick my clit, Harder! Harder!” Paige demanded.

Matt plunged his tongue deep inside my wife before returning to her clit, and the sensation of his tongue moving back and forth over her clit and penetrating her vagina drove her to the brink of orgasm.

“Don’t stop, Matt. Don’t stop. Yes. Right there. Right there! You’re gonna make me cum!”

Paige’s face tightened and her body shuddered as her first orgasm of the night approached.

“Oh, God! Fuck. Yes. Yes,” she yelled as her orgasm moved through her body. She came hard and her body shook uncontrollably while Matt continued licking her. I hadn’t witnessed her come that hard in years.

Once her long orgasm subsided Paige turned and knelt on all fours, her pretty little ass facing Matt.

“Fuck me,” Paige demanded. “I want your big dick inside me.”

Matt knelt behind her and placed his hands on her hips. With his chin glistening from Paige’s juices, Matt teasingly rubbed the head of his cock around Paige’s wet pussy before entering her. He slipped just the head of his cock into her, and it slid easily inside. Slowly, he inched his cock in deeper, and when he fully penetrated her, Paige gasped.

“Oh, my God. You’re so big! It feels so fucking good,” Paige exclaimed.

I knelt beside Paige and she put her mouth on my cock, struggling to suck it as a second orgasm was building. The pleasure that was starting to spill over inside her caused her to release my cock and surrender to her pleasure. As Matt thrust harder, I could hear the sound of Matt’s balls slapping against my wife’s ass. Paige moaned louder and her breathing became heavier. Gasping, Paige gripped the bedsheets and squeezed them with both hands, bracing for another orgasm. I lay back and watched as her face became flushed, her orgasm nearing. I reached down and gently squeezed her erect nipples while this wonderful scene unfolded in front of me. Moments later, Paige yelled again that she was cumming, and after a few moments of heavy breathing, she rocked her head up and down as the contractions kicked in.

Paige’s pussy contracted and pulsated around Matt’s cock, as if trying to coax him to come as well. Amazingly, Matt didn’t cum, but rather pulled Paige into him and kept still, allowing her to savor the intense pleasure he just gave her. What a wonderful, unselfish act, I thought.

As Paige began to regain her composure, she brought her mouth back to my cock and began sucking me. Matt threw his head back and took a breath as he started fucking my wife again with deep, steady strokes. Matt’s tempo increased with each stroke, and now he was plunging his cock in and out of her hard, pushing and pulling Paige's hips forward and back, making it impossible for her to suck me. Much to my chagrin, Paige released my cock again; I was so close to cumming.

Matt fucked my wife with abandon and Paige encouraged him.

“Fuck me. Fuck me. Cum for me! Cum for me!” she yelled.

Matt’s head tilted back and he grunted loudly. Removing his cock, he unleashed a long rope of milky cum onto the middle of my wife’s back, followed by several more spurts that landed on Paige’s ass. Witnessing this put me over the top, and I slid my cock into Paige’s mouth and immediately erupted. Paige swallowed as much of my semen as possible, with the overage spilling out of her mouth and onto the bed sheet. 

After a brief break that included several bottles of refreshing cold water, Paige rinsed off in the shower and brushed her teeth. When she returned to the bed she lay between us with her damp bath towel wrapped around her. No longer pinned in a bun, Paige’s damp, shiny brown hair fell loosely below her shoulders. Matt and I sat against the headboard with our semi-erect penises.

Paige took a sip from my water bottle and asked, “Who’s ready for round two?”

Paige began stroking us simultaneously and we were hard in no time. Removing her bath towel, Paige gazed into my eyes and said, “I’m going to suck Matt’s cock while you fuck me from behind,” then slid down on Matt’s torso and took him into her mouth. Like before, Paige teased Matt with her tongue and fingers, licking the length of his shaft and stroking him with her fingertips. Paige gives amazing blowjobs and tonight was no exception as she painstakingly sucked and licked Matt’s big cock. Matt leaned back, closed his eyes, and let Paige pleasure him.

I moved behind Paige and entered her from behind. Paige gasped as I entered her wet pussy with one long stroke while she continued sucking Matt. I fucked her with long, deep strokes as more thunder and lightning flashed outside. Paige was in absolute heaven, getting exactly what she fantasized about for so long, one cock in her mouth and another in her pussy.

Paige released Matt’s cock from her mouth, turned, and blurted, “I want you to fuck me in my ass.”

I removed my cock from Paige’s wet pussy and reached for the night table drawer to retrieve a bottle of lube and my trusty rubber cockring. I stretched the cockring and wrapped it around my scrotum. My cock swelled immediately, its veins bulging from my shaft. I poured some lube on my cock to get it nice and lubricated and was preparing to pour some on her ass when I saw that Paige had already mounted Matt.

With Matt’s cock buried inside her she said, “Come fuck me. Put it in my ass.”

I poured a generous amount of lube on her opening and slowly placed the head of my swollen cock on the edge of her ass. I placed my hands on her hips and positioned myself behind her, angling my hips until my swollen cock head was pressing against her opening. Slowly I pushed my hips forward until my cockhead penetrated. I gently parted her cheeks and slowly slipped in deeper, careful not to go too deep too soon. She was incredibly tight, and Paige gasped as I began rocking back and forth, my cock inching deeper with each stroke. When I finally got about half of my cock inside her she moaned deeply.

"Mmm god, baby. Keep going."

Paige wrapped her hand around the base of my cock, slowly pushing me in deeper. About three-quarters of my cock was buried inside her ass, and I paused, remaining motionless for a minute, letting her relax before entering her further.

"Mmm, baby. That feels so good," she said while rocking up and down on Matt’s cock.

Matt moaned as Paige slowly bobbed up and down on his hard cock, careful not to dislodge either of us from either orifice.  

"Fuck me, babies. Give it all to me," she said to both of us.

I responded by tightening my grip on her hips and pulling her back toward me. I thrust my hips forward and nearly my entire cock penetrated her ass.

"Ugh, fuck," she groaned. "You're so deep. Fuck me! Fuck my ass!"

I pulled back and thrust again, this time more forcefully, causing her ass to slap against me.

"Oh!" she gasped. “Keep going!” she yelled.

I continued fucked her slowly and steadily while Paige continued sliding up and down on Matt’s cock. I spread my legs wide and lifted myself from my knees, and standing while supporting my weight with my hands, I plunged my straining cock deep in her slick ass. Paige was gasping as Matt and I fucked her together.

"Do you like his cock inside you?” I asked. “Are you going to cum on this big cock?”

"Mmm, yes."

"Tell him. Tell him you like it."

"Oh, baby. I love his big cock. Oh, fuck. I'm going to cum," she bellowed indelicately. "I'm going to cum all over his big dick. Make me cum, baby. Make me cum."

Her grunts and moans became unintelligible as her orgasm approached. I thrust deeply inside her and left my cock there, letting her spasm around me, then removed my cock and sat back, content watching Paige cum while Matt fucked her.

Paige rolled off of Matt and turned around with her ass high in the air.

“Fuck my ass,” she demanded.

Matt ran his hard cock along the length of Paige’s wet pussy, getting it lubricated, then inserted it into her ass. It slipped in effortlessly. Matt fucked her with long, deep strokes and within minutes Paige had another orgasm, her body shuddering.

Matt removed his cock from her ass and Paige turned on her back. Spreading her legs wide and placing her hands behind her knees, she pulled her legs as far back as she could. Matt lay between her legs and frantically began licking her pussy.

Paige moaned and squeezed her nipples as Matt’s tongue lapped at her clit.

“Oh, my God, I’m gonna cum again! Oh, God, I can’t believe it!" she yelled.

Rocking her head back and forth, her orgasm struck, sending waves of pleasure through her. Matt slid atop of her and pushed his cock deep inside of Paige’s pussy and began fucking her, his body literally flying off the bed with each stroke. Droplets of fluid were spewing out of Paige as Matt fucked her. I never saw Paige that wet before, and I instinctively began stroking my cock.

Matt slipped his cock out Paige’s pussy and straddled her chest. He began stroking himself with his right hand while supporting his weight with his left hand, resting it on the headboard. When Matt announced he was cumming, Paige opened her mouth and stuck out her tongue.

“Cum in my mouth. I want to taste you,” Paige demanded.

Matt released his grip and allowed his cock to throb over my wife’s open mouth. She grabbed his cock just as he ejaculated, and a glob of warm semen landed on her tongue and slid into her mouth. At that point I came too, shooting a long stream of cum onto the floor. I hadn’t cum twice in one night in a long time!

Paige licked Matt’s cockhead as his semen dripped into her waiting mouth and down her chin. Her tongue was coated with Matt’s semen, and as his orgasm began to ebb, she looked him in the eyes and swallowed his load.

Once Matt dismounted my wife, Paige lay back and wiped her face with the bed sheets.

"Oh, baby! That was incredible," Paige said with a smile in her voice. Then she looked over to me and asked, “Are you okay?”

"Oh yes, baby. That was fucking hot,” I replied.

I collapsed on the bed next to Paige, cradling her in my arms with my body pressed against her side.

"Mmm!" she moaned, sighing softly.

Matt joined us, pulling himself tight to Paige’s other side with her nestled firmly between us. We lay there breathlessly for several minutes.

"This is how every vacation should be," Paige said.

We all started laughing together. We couldn't help it. It was infectious and I felt good knowing I was a part of this experience for Paige.

“Maybe we can do this again on our next vacation but this time with another woman,” I said to Paige.

“That’s a thought. We may want to try that,” she answered.