Because we would soon be naked in front of complete strangers, we went on a crash diet and began working out at a frantic pace. The fact that we were improving our physiques boosted our confidence, which only made us want each other more. One day, Michelle surprised me when she entered my home office completely naked — and completely shaved. I had begged her for years to shave her pussy for me, but she absolutely refused to do so. And yet, there she was, completely smooth.
I practically jumped on top of her, spread her legs, and licked, kissed and sucked her wet pussy for a good, long time. I thoroughly enjoyed the feeling of her smooth skin on my tongue and the full, unobstructed access she had given me. Afterward, she explained that she had read that many of the women at Desire have shaved pussies, and she didn’t want to look out of place. She booked an appointment to have a Brazilian wax the day before our trip, which ensured that she would be silky-smooth the entire week.
We began going out on “dates” more often, mostly so that we could talk without being overheard by our children. Everywhere we went, we held hands and kissed, and we spoke in hushed tones about all the naughty possibilities of this exciting new world we had just opened together. We shared a delicious secret that no one could ever know, and there was something incredibly thrilling about that. We had allowed each other the freedom to express ourselves openly; which meant that if I saw an attractive woman, I could point her out to Michelle instead of pretending not to notice. Michelle would also point out the men she found attractive, and I was surprised that she always seemed to gravitate toward older and/or bald men.
“What if you had sex with some guy with a huge dick, and he was better than I am?” I whispered over a restaurant table during one of our many conversations.
“I’m sure it will be better,” she said, casually.
“You know what I mean. Sex will be better with someone new because it will be different. I’ve told you many times you’re the best I’ve ever had in bed, and you’ve told me the same. But there’s one thing we can’t give each other in bed, and that is something different. Different is always better because it’s new and exciting.”
It was difficult to find fault in her logic. If we were really going to go through with this, we had to abandon all our insecurities and simply trust each other. As Michelle told me many times, no matter what happened, nothing would ever change how she felt about me and how I felt about her.
Since we would be having sex with someone new for the first time in more than seventeen years, we also decided to brush up on our sexual techniques. This was Michelle’s idea, of course. I discovered that she takes a great deal of pride in being able to satisfy a man with her mouth, and as she tends to be a competitive person, she had a strong desire to be the best. In order to hone her craft, she spent a good deal of time going down on me, and I provided her with feedback on what I liked and didn’t like.
When I mentioned that it would be amazing to experience a deepthroat blowjob someday, she did some research online and found a throat spray that numbs the back of the throat. She immediately drove to the nearest sex shop down the road, purchased that spray, and excitedly showed me her discovery once she returned home. Incredibly, she only used that spray twice, and was then somehow able to take me all the way to the back of her throat without using the spray from that point on.
Finally, after what had seemed like an eternity, we arrived in Cancun. A shuttle bus was waiting for us at the airport, and as we drove to the resort, I squeezed Michelle’s hand with increasing urgency. My heart was thumping in my chest, and my insides churned with a mixture of nervousness, excitement, anxiety and outright terror. After talking about this vacation for so long, it was difficult to believe that it was actually happening.
We arrived at the resort, and were greeted with a warm reception and glasses of champagne. We signed in to our room, and as we waited for our room key, a couple walked by the glass doors at the rear of the lobby. They were both completely naked. She was very tall, blonde, and built like a fitness model, with giant (and clearly fake) tits. He was also tall, bronzed from head to toe, and had bulging, rippling muscles and a massive schlong that swung low between his legs.
“Okay…not too intimidating,” I muttered, and Michelle giggled.
We were given directions to our room, and we headed out the same doors where I had just seen the naked couple. The warm Caribbean air washed over us once again, and the ocean air filled our lungs. As we strolled through the resort, several happy couples, mostly dressed in swimwear, greeted us with a warm “hello”. We found our room, which had an obstructed view of the pool.
Famished, we decided to head to the lunch buffet while we waited for our bags to arrive. The buffet is located toward the rear of the pool area, and as we walked, the most amazing scene was slowly revealed before us. There were at least fifty people lounging in and around the pool — all completely nude. They were all chatting and laughing so casually it was as if they weren’t naked at all. Some were playing volleyball; others were lounging in the sun; and many others were simply standing in the water and chatting.
We grabbed our plates and our food, and tried to act casual and blend in as we sat at a small table and watched all of the frolicking naked people. I was relieved to notice that not all of the guests were as well-built as the first couple I saw. All shapes, sizes and ages appeared to be represented. I couldn’t help but notice a few of the women who were particularly attractive. And I also couldn’t help but surreptitiously glance at the packages of the men to verify that I was truly an “average” guy.
By the time we finished eating, our bags had been delivered to our room. We changed into our bathing suits. I wore a standard pair of shorts, and Michelle wore a bikini bottom with a sheer, white, see-through top. Her nipples protruded straight through the fabric, and it was impossible not to touch them. But just as I began to get worked up, she put a stop to it, as she was eager to sit by the pool.
We found a couple of chairs in the shade, and before I had even sat down, Michelle was already completely naked. She wasted no time at all getting into the spirit of the resort, and I was impressed — even awestruck — by her lack of hesitation. With her fair Irish complexion, she doesn’t ever tan; she burns and freckles. We were surrounded by fully tanned bodies, and her smooth porcelain skin, contrasted with her long, curly red hair, really made her stand out from the crowd.
I shed my shorts as casually as possible, though inside I was a bundle of insecurity. I gave my cock a tug to make it look a little longer, and tried not to think about how many people were looking at me as I settled into my chair. Within moments, a very friendly server asked us what we’d like to drink. Several rum punches later, my insecurities melted away.
I couldn’t wait to get to the hot tub. I had read so much about it over the past several weeks that I was excited to experience it first-hand. As soon as it opened at around 3:00pm, I nudged Michelle, and we headed to the roof.
We were among the first to arrive, and after depositing our belongings in one of the cubby holes, we entered the hot tub and waded over to the bar. The bartender, Carlos, was amazingly attentive. Whenever our drinks would get a little low, he would replace them with a fresh one before we had even requested it. Within no time at all, I found myself light-headed from all the rum, combined with the hot water and the blazing Caribbean sun.
More and more people filtered into the hot tub area as the day progressed, and by the time the sun began to set, the hot tub appeared to be filled to capacity. There were so many naked bodies standing in the water, it was difficult to move without brushing up against someone. The atmosphere was indescribable; like a frat party for middle-aged adults. Everyone was so friendly and so happy to be on vacation. And the fact that we were all naked seemed to place all of us on a level playing field where social status was thrown out the window. We met people from all walks of life and with a variety of backgrounds, and the fact that we were all there to have sex gave us something in common to discuss.
As the evening wore on, the activities in and around the hot tub grew more playful. At one point, a woman hopped up on the bar and lay down. Carlos handed a shot to one of the guys, who poured it all over her. Then a man and a woman simultaneously licked it off her. Another man brought a water gun filled with Bailey’s liquor and floated around the hot tub, shooting it all over women’s tits, which the men (and women) would then happily devour.
At another point, I noticed a man was sitting on the ledge of the hot tub, and a woman’s head was bobbing up and down on his lap. I recognized the man, as we had just met him moments before, but the woman sucking his cock was definitely not his wife.
Several canopy-topped beds were lined around the perimeter of the hot tub area. On one of the nearby beds, two couples were going at it. One couple was fucking with the woman on top, and the other woman had her legs spread wide, moaning loudly without any inhibition as the man on top of her thrust himself into her. Live sex shows were happening all around me, and it was difficult to conceal my raging hard-on under the bubbling water.
Michelle and I were separated at one point, and when I found her again, she was talking to a couple at the opposite end of the hot tub. After making my way to that end of the tub (taking great care not to brush my hard-on against anyone along the way), she introduced me to them. Danielle was an attractive woman who appeared to be in her late-40’s. She was obviously a fitness freak, judging by her tight and muscular body, and she validated that assumption when she later told me she is a Pilates instructor. She had dark eyes, a sexy smile, and large breasts that appeared to be fake. Her husband, Dave, was tall and lean, and had an easy-going personality and quick wit.
Michelle and I spent a good deal of time chatting with the two of them, and we all seemed to connect instantly. We learned that it was their last night at the resort, and they gave us several tips to help us enjoy our stay. As I broke off in conversation with Dave, Michelle and Danielle moved further away until they were out of earshot. Although I couldn’t hear what they were saying, I was unnerved by the way they were smiling and their furtive glances in our direction.
When they rejoined us, Danielle immediately pulled me aside and surprised me by wrapping her arms around my shoulders.
“Michelle tells me you’re here to celebrate your 40th birthday,” she said.
“Yeah, it’s coming up soon,” I replied, and I put my arms around her waist. She was amazingly slim and firm. I realized that I hadn’t touched a naked woman other than Michelle in nearly twenty years. I glanced over at Michelle to make sure she was okay with me touching this woman, but she was engrossed in conversation with Dave, and didn’t seem to notice. Danielle turned me so that my back was to them. I could feel my cock growing harder as I let my hands drop toward her hips. I desperately wanted to get my hands on her firm ass.
“She also tells me that you’ve always fantasized about having a threesome,” she purred.
“Well…uh…she said that? Umm, yeah,” I stuttered.
“Well, maybe we can make that happen.”
And with that, she leaned in and kissed me. My initial reaction was sheer panic. Although Michelle and I had talked about kissing others, and we were both comfortable with it in theory, I wasn’t sure how she would react now that it was actually happening. Even though I knew I had permission, it still felt wrong. But Danielle was such a good and tender kisser that the initial shock faded quickly and I allowed myself to enjoy the soft lips and tongue of this woman I had just met. I also let my hands roam down to caress and squeeze her firm ass. It felt exactly as incredible as I had imagined.
After making out for a couple of minutes, I needed reassurance from Michelle that she was okay with what I was doing. I turned around to glance at her, but her eyes were closed. Dave was embracing her from behind. He had both hands on her tits, and was kissing her neck. She was leaning her head back to expose more of her neck…and one of her hands was stroking his hard cock under the water.
In the weeks leading up to this adventure, Michelle and I had endless discussions about the lines we were willing to cross, and how much of each other we were willing to share. I was confident that I would not only be willing to share her completely, but that it would turn me on to do so. But again, there is no way to know how you will react until it actually happens. I felt an immediate and overwhelming combination of adrenaline, panic, jealousy and insecurity. But most of all, when I saw my wife stroking another man’s cock for the first time, it was the most thrilling and arousing sensation I had ever experienced, before or since then.
“I guess she’s okay,” I quipped to Danielle, and we continued our make-out session. She reached into the water and wrapped her hand around my hard cock as we kissed. I had forgotten how thrilling it can be to have a strange hand stroking your dick.
Eventually, Danielle excused herself to the ladies room, and when Dave saw her leave, he followed her. Finally, I had the opportunity to reconnect with Michelle.
“What are you doing?” I asked. “I thought we had agreed we weren’t going to hook up with anyone on our first night.”
“Are you complaining?” she responded. “Danielle is smoking-hot! C’mon, you know you want her.” I could tell she had a few too many rum punches.
“So you’re okay with seeing me make out with her?”
“Are you kidding? That was really hot! Are you okay with seeing me and Dave?”
“Then what’s the problem?”
Once again, it was difficult to argue with her logic. I had wanted to ease into having sex with others, but there wasn’t any compelling reason not to seize this opportunity. When Danielle and Dave returned, we all agreed to go back to their room. Dave and I stayed behind while the girls went to their room. They had a deluxe suite with a hot tub in the room, and they needed time to prepare it.
I ordered another drink from Carlos to calm my nerves, as I had been chugging water for the past hour in order to rehydrate. As we chatted in front of the bar, we were approached by a couple of women. They introduced themselves, and then asked if we’d like a blowjob. Dave immediately said yes, and I just nodded my head stupidly.
They lowered themselves into the bubbling water. The blonde put my dick in her mouth while the brunette took care of Dave. I gave Dave a strange look, and he just laughed and high-fived me. After a few minutes, they rose to their feet, thanked us, and then disappeared. I could only imagine that this had been some sort of dare, or perhaps they had lost a wager. Whatever the case, it was time to check on the girls, so off we went to their room.
In the back of my mind, I was hoping to see Michelle and Danielle making out when we entered the room. Although Michelle had never been attracted to women, she mentioned that she might want to try playing with a woman during our vacation. Seeing those two hot women going at it would be quite a treat. Instead, when we opened the door, our wives were merely lounging in the hot tub and chatting.
Dave and I joined them, and we sat boy-girl-boy-girl around the tub. While we continued our casual chat, I felt Michelle’s hand rubbing my left thigh, and I responded by rubbing hers as well. I then felt another hand on my right thigh. Danielle smiled at me, and I began stroking her thigh under the warm water.
I then noticed that Michelle’s left hand had disappeared, and Dave had a very content look on his face. The up-and-down motion of her arm was a dead giveaway as to what she was doing. Moments later, her right hand moved to my stiff shaft. She now had a hard cock in each hand. I felt a second hand join Michelle’s, and the two hands played together, alternating strokes and playing with my balls.
“What do you say we move this over to the bed?” Danielle asked, and we all quickly complied.
The girls instructed me to lie down on my back, with my head propped up against the baseboard with pillows. Both ladies then seductively crawled between my legs. Michelle was the first to put my dick in her mouth, and she showed off her deepthroat skills by taking me all the way into the back of her throat while Danielle lightly played with my balls.
Michelle then made the sexiest move I had ever seen, and handed my dick to Danielle, who slid me right between her soft and luscious lips and into her mouth. As she did so, Michelle moved lower and began licking my balls. I now had two women licking and sucking my cock at the same time. Another item had been scratched off of my bucket list.
The two girls continued to take turns sucking my cock, passing it back and forth between them. Every once in a while, one would begin to lick up and down one side, and the other would join, licking up and down the other. The sensation of having two tongues on my cock at the same time had been a fantasy of mine for so long, and the reality exceeded my wildest fantasies.
While the girls continued to work on me, Dave was lying on his back to my left, stroking his cock and simply watching. I was somewhat intimidated to notice that his dick was at least an inch or two longer than mine, but I tried to remind myself that it isn’t a contest. At some point, Michelle reached over and took over the task of stroking him while she continued to take turns sucking me. Then, after handing off my cock to Danielle once again, she moved over between Dave’s legs and took his dick in her mouth.
Over the years, I had jerked off many times to the fantasy image of seeing my wife’s mouth on another man’s cock. Never, at any point during that time, did I believe that I would ever actually witness that act. Watching her take Dave’s long cock down her throat, seeing the expression on his face, and hearing his low groan, was so incredibly arousing, I immediately felt an unstoppable surge of cum begin to erupt straight through my shaft.
It came as a complete surprise to me, as I hadn’t felt that I was close to cumming until it was too late to stop it. Danielle had her mouth on my cock when I felt that first surge, and I frantically tried to warn her, but it was too late. I spurted my first load into her mouth, and she gagged a little and reflexively jerked her head back. When she removed me from her mouth, she spit out a large amount of milky-white cum from the corner of her mouth. She didn’t seem happy about that, and I apologized as two more spurts erupted from my swollen head, covering my belly in fluid.
“I’m so sorry,” I said. “I really didn’t mean to do that. It snuck up on me.”
Michelle took her mouth off of Dave’s dick, looked over, and giggled uncontrollably. Here I was, finally living out my lifelong fantasy, and I was already finished. I excused myself to their bathroom and cleaned myself up. I then noticed a little blue pill on the counter. Earlier, while we were standing in the hot tub waiting for the girls, Dave had mentioned that he bought a few Viagra pills from the gift shop, and that I was free to take a bite of one if I wanted. I had never taken one before, but figured I might need one if there were going to be any chance for a second round.
When I re-entered the main room, I saw that Danielle and Michelle were taking turns sucking Dave’s cock. I sat on the lower half of the bed and ran my hands along the girls’ smooth legs and watched with great interest as Dave’s impressive cock slowly disappeared into my wife’s eager mouth. She was clearly enjoying what she was doing, as she was moaning nearly as loudly as he was.
I let my hands roam a little further north up Danielle’s legs and gently stroked her thighs. She parted them for me a bit, giving me access to her pussy. Just as Michelle had noted in her research, most of the women at Desire were fully shaved, and Danielle was no exception. I desperately wanted to taste her, so I began kissing my way up to her cunt. She was turned sideways, but once she noticed what I was trying to do, she turned over completely onto her back and slid down the bed so that I could get a much better position.
I teased her a bit with soft, flicking motions with my tongue over her clit. I licked my way from her entrance all the way up to her clit, up one labia and down the other. I took as much of her into my mouth as I could and gently sucked. And I swirled my tongue around her clit, and alternated with gentle kisses.
She tasted clean and sweet, and judging by her soft moans, I seemed to be giving her as much pleasure as she had given me. Although I was thoroughly enjoying what I was doing, I couldn’t resist glancing over at Michelle from time to time. She was giving Dave an amazing blowjob, and his eyes were rolling to the back of his head. I continued to work on Danielle, and inserted a couple of fingers into her wet opening. It took me a while to figure out just the right combination of movements that she enjoyed, as she responded so differently than Michelle. But I seemed to have hit the right spot, judging by her breathing and the way she held my head in place.
The next time I looked over at Michelle, she had switched places, and Dave was now licking her pussy. Her eyes were closed, her lips were parted, and she wasn’t shy about telling him what to do.
“Oh, yes — right there!”
“No, don’t stop!”
“Harder! Yes! Oh, god!”
She was never this vocal at home, I thought. But we had spent so many years being as quiet as possible during sex because of our house full of kids, and we never really had the opportunity to be vocal.
After a while, I asked Dave to switch places with me. I desperately needed to reconnect with my wife. He reluctantly agreed, and I began licking and sucking Michelle’s pussy. She was incredibly wet, and knowing her body much better than Danielle’s, it didn’t take me long at all to get her to orgasm. She came loud and hard, and shook the bed as my fingers and tongue struggled to keep up with her.
Meanwhile, Danielle had flipped over onto all fours, and Dave was slowly fucking her from behind. Her gorgeous ass looked so inviting, and I envied his position. Michelle was still reeling from the after-effects of her orgasm, and I crawled up from between her legs and kissed her passionately. Amazingly, I could already feel my dick becoming hard again. Either that little blue pill was doing its trick or this situation was far too exciting not to be aroused. I continued to move up her body until I was straddling her face. She took me into her mouth and in no time at all I was fully erect.
I slid back down her body and positioned myself between her legs, placing my cock right at her opening. She gasped as I entered her, and she was so swollen and wet it felt incredible. The four of us continued fucking side by side on the bed for several minutes until Dave announced that he was about to cum.
I heard a voice say, “Cum on Michelle’s face”, and I was startled to discover that the voice was mine. I was lost in a world of raw sex and lust, with a belly full of rum punch, and had no idea what I was saying anymore. The whole situation was so surreal. When Michelle and I were exchanging fantasies prior to our trip, I mentioned that I would pay anything to see a man cum on her face. There was something about that act that I felt was just so dirty, it made me hard just thinking about it. In seventeen years of marriage, Michelle had only let me to cum on her face once — and it was in the week leading up to this vacation.
Dave began thrusting in and out of his wife a little faster. He then pulled out and moved quickly to the head of the bed. He positioned himself directly over Michelle’s face and, stroking his cock, ordered her to open her mouth. To my amazement, she did. He pumped out a stream of cum directly into her mouth, which she promptly spit out of the corner of her mouth. Another stream covered her cheek, and another splashed across her closed lips and chin. He continued to stroke himself over her face and squeezed out several more drops before he was completely drained.
Michelle’s face was covered in another man’s spunk. It was the dirtiest, most erotic vision I could ever imagine. She gave me a huge smile, and then asked for a towel. We all laughed at the absurdity of what had just happened.
As Dave rose to get a towel, he pointed to Danielle, who was still on all fours, with that amazing ass facing in my direction.
“You wanna hit that?” he asked.
I looked at Michelle, and she smiled and nodded her approval. Danielle gave me a sexy smile as well, and shifted down the bed toward me. Dave handed me a condom and then handed Michelle a towel. I hadn’t worn a condom in nearly twenty years, and I fumbled with it clumsily before finally managing to wear it the proper way.
I positioned myself behind Danielle and ran my hands over her smooth, round ass. I rubbed my cock along her slit and then pushed inside her. I tried to go slowly, just as Dave had been with her earlier. I savored the feeling of her hot, tight cunt wrapped so firmly around my cock, and I couldn’t take my eyes off of her gorgeous ass.
I slid my dick in and out of her faster and faster, and I could feel another orgasmic wave building inside me already. Michelle had gone to wash up in the bathroom, and Dave was sitting at the head of the bed, watching us with interest. I couldn’t hold out much longer. The pressure was building inside my balls, and every thrust brought an increasing sensation of pleasure. I pounded into her harder and harder until another burst of fluid erupted from my cock and filled the condom to capacity.
I collapsed onto the bed, completely spent, and Danielle did the same. She flipped over onto her back, and I kissed her and thanked her for an amazing time. With a cum-filled condom dangling comically from my softening cock, I excused myself to their bathroom once again.
When I returned, I heard the sound of moaning and slapping flesh coming from the main room. It occurred to me that Danielle hadn’t finished, and I felt terrible that Dave was now picking up where I had dropped the ball. I couldn’t believe that he was ready to go again so quickly, but assumed he had taken one of his blue pills, too.
As I entered the room, however, I saw Danielle sitting on the opposite side of the room on a couch. I then turned toward the bed. Michelle was on her back with her legs high in the air, and Dave was on top of her, thrusting into her hard and deep. My wife was now being fucked by another man. Yet another line had been crossed. It was all happening so quickly, it was difficult for me to process.
I joined Danielle on the couch, and we silently watched as Dave continued to trust his hips hard between Michelle’s open legs. She was moaning so loudly that it seemed the entire resort could hear her. Her legs were so high in the air, I couldn’t figure out how it was possible. Then I noticed that Dave had shoved a bunch of pillows under her ass in order to elevate her hips. Later, Michelle told me that this created an amazing and unfamiliar angle that felt incredible. One of the benefits of being with new people, we discovered, is learning new tricks.
Michelle’s moaning grew even louder and more guttural, and her body became incredibly tense. She grabbed Dave’s ass with both hands to keep him in place, and she shook beneath him. When she finally stopped shaking, he withdrew from her and rose to his knees. Aside from the heaving of her chest, she barely moved for several more minutes.
Finally, we said good-bye to our new friends and made the “walk of shame” back to our room with our clothes in our hands. On the way, we began to replay the events of the day and night. By the time we returned to our room, we were so horny from talking about what had just happened that we had sex yet again. Our first day of vacation had already surpassed our wildest expectations.