A sweet wife slowly learns to let go on vacation

Swingers storie – A sweet wife slowly learns to let go on vacation

We were empty nesters and it was mostly going pretty well. I have heard it said that the primary problem that many empty nesters have is that they can’t stop smiling. While my wife Jennifer missed the kids somewhat, texting made things much better than it would have been 30 years ago. She was slowly starting to become someone who was not a non-stop mom, but a regular person who occasionally thought of herself.

And if she wasn’t always thinking of herself, well, I often was. My wife had this almost eternal youth thing going. She was in her very early 50’s but she honestly looked about 20 years younger except for the random sprinklings of gray in her brown hair. Jennifer was probably in better shape than she was back then when the kids were younger, and the fact that about 2% of her hair was light gray against the rest of her darker hair looked really hot on her for some reason. Her skin was a beautiful light brown, and she had a dazzling smile that drew people to her. She didn’t have enormous breasts, but they were amazing. They had survived age and children proudly and defiantly, and they were topped with prominent nipples that made the package perfect.

On the face of it, I had nothing to complain about. I had a beautiful wife, and indeed a willing wife. She loved my passion for her and knew how to excite it – within limits. Unfortunately, she also had classic morals to go along with her classic beauty.

In the beginning of our relationship, I figured this would evolve as sex usually does in a relationship, but it didn’t. Well, it did, but at a glacial pace. After 30 years, she had reached a place where she was okay with me talking about fantasies for fun as long as I understood that she didn’t really think about these things as much as I did. And after 30 years of relatively vanilla sex, albeit with a gorgeous woman, I had a lot of fantasies.

I tried to talk her into a few of these fantasies, but she wouldn’t really bite on any of them. She didn’t hold it against me at all, even when I occasionally talked about having sex with another woman just for fun, but she mostly just laughed them off. Mostly.

While she made some very strong statements about not being interested in anything that didn’t look like a model marriage situation, you could tell that she didn’t really push back in a big way when I started talking about her showing herself off for other people, especially guys. She used slightly different language when I started talking about her being the center of attention poolside in a bikini that would become see-through when wet or maybe at a topless beach with a bunch of young men walking by. She wouldn’t say she wouldn’t do it, she’d just say something like, “That’s not the sort of thing a nice woman would do.” And then she’d start getting just a little more excited, sometimes so much that I think she was embarrassed that her body was betraying her.

Occasionally, when I wasn’t talking about it she’d clearly be trying to lead me into it in a way that didn’t make her look bad. “Wouldn’t it be terrible if people were watching us?”, she’d say in mid-fuck. “I’d be so embarrassed…they’d probably think I was a total slut”, she would say in the most innocent way possible so she could look like a good wife. But she knew where I’d pick up that conversation, assuming that her mentioning it didn’t get me off right then and there. The thought of some guys seeing me drill my wife while her tits bounced around and her legs wrapped around him was often just the thing that made me come like a teenager.

After decades of waiting for her to come out of shell a little, I decided I had to stop being patient and take a little more initiative. It was becoming clear that she didn’t hate the idea of being a little more free-spirited, but was paralyzed by the notion that her very large circle of conservative acquaintances might find out something and her reputation would be ruined. I needed to get her somewhere that she could be a little freer, where the atmosphere was just a little more sexually charged, and where she didn’t know anyone.

I knew she wouldn’t go for anything so obvious as one of those hedonistic sorts of resorts, and honestly I wasn’t looking for a completely booze-drenched atmosphere. I just thought that something that was focused primarily on adults might be what the doctor ordered, just to get her out of “good mom” mode and into something just a little more uninhibited and grown up. Most of our vacations had been touristy ones with the kids, and it took a while to get her to warm up to the idea. But again, when I made it clear it would make me happy to hit a fairly upscale, all-inclusive resort set in the Caribbean and just take it easy for a week, she was happy to acquiesce. I wasn’t really hoping for a miracle, but I’m the sort of person who is naturally happier in problem-solving mode and couldn’t help but be just a little energized by this.


We don’t live in a big city, so any plane travel destination is usually a bit of a haul for us. But we made it to the resort by the early evening in a good mood. The resort itself was not so much a traditional hotel set up so much as a set of duplex bungalows scattered around a central location with a restaurant, common area and pool. The suites weren’t large, but they had a separate living and bedroom area along with a kitchenette. There was a bar in the restaurant, and there was a separate bar by the pool. The pool area also included an in-ground hot tub that was starting to become more popular since the sun had started to set.

We like to go for walks, especially on vacation, and we spent the early evening touring the surprisingly large property. It gave us a feel for what the place was like and also helped it relax us from the plane flight out. And it didn’t hurt that I had grabbed a whiskey sour from the bar as we went out. Jennifer said she didn’t feel like a drink tonight, but what she actually meant is that she didn’t want to look like the kind of person who ordered a drink as soon as she hit the property. As she drank most of my whiskey sour we took a look at the place and were feeling pretty good about our decision to come here.

As we passed back by the pool area so I could get an actual drink for myself, the hot tub was starting to get a little more lively. It was filling up with people and these people were clearly on vacation to get away from their normal lives, and it was exactly what I was hoping to find in this resort. People were showing skin, looking at skin and no one seemed to have any concern about it in the least. I could have stayed and watched for quite a while since there is nothing hotter than a woman who feels comfortable in her skin, and there were a lot of very comfortable women there. There was also a nice variety in ages, which I think was comforting to my wife as she had expressed concern that this seemed on paper like a place for people half our age. Given the price, I was actually a little surprised to see as many younger folks there as there were.

I asked my wife if she wanted to change into our suits, knowing full well that the hot tub and booze scene was a little more mine than hers. She hesitated a bit, and then said she was really too tired this evening but was looking forward to it some of the other nights. It sounded like a bit of an excuse but the way she said it made me optimistic.

We went back to just relax a bit, get cleaned up and then hit the sack. We unpacked and went through our normal evening routine. The bedroom had a reasonably large window that looked towards the property. It didn’t look out directly on to the common area, but it did look out over some of the pathways that ran between the different bungalows. As she got undressed and got ready for bed, I noticed she didn’t close the blinds. I called her out on it, and she said, “It’s a nice view and I don’t think anyone will be out there. They are probably not supposed to be closed.” That was a very funny way of saying that, I thought. But she is the sort who finds comfort in doing things she’s supposed to do. Me, I honestly didn’t give a shit. I spent years doing organized sports and have been naked in front of god knows how many people. And if people wanted to see how hot my wife is on this vacation, well that was sort of the point.


We slept well and woke up feeling good. I woke up hard as a rock as I often do. Often this is met with an exhausted eye roll from my wife. This was one of those mornings where it wasn’t. She moved her arm under my neck, which is our language for, “You need to climb on top of me.” I think that she was too embarrassed to come out and ask for some foreplay most of the time but felt totally comfortable with having me lay on top of her with my hard dick rubbing back and forth on her crotch. I mean, that’s sort of a hug, right? A hug between two people. A hug where one person is naked and the other is wearing some very thin panties. A hug where there is a lot of skin pressed against each other, including some glorious tits that would cause nations to go to war. A hug where both hips are sliding back and forth in a much-practiced rhythm.

I reached down to remove her panties since that was our system. She would rarely remove them herself during sex. I don’t know why that is. I think it was more defensible to her sense of good grooming if her husband removed them. She wasn’t a bad girl that way, just a good girl who had unfortunately found herself in a situation with a rock hard dick that she would be forced to fuck. And the fact that she was dripping wet? Well, that was just her body protecting itself since that big dick was probably going to pound her hard.

I started rubbing my dick slowly around the outside of her pussy as I often do to make sure she was ready, but she was having none of that. She grabbed my ass and pulled me in all the way. I didn’t need any additional signals after that. This was not going to be a slow gentle morning coupling where we talked about what might be fun to do later. This was going to be fast. As I got a good rhythm going and started using my hands on her ass and tits, she was clearly getting into an unusually receptive manner. After a few short minutes, she was going at it like I had never seen.

“You look so fucking hot right now. A good girl being very bad. What would people think if they saw you getting pounded so hard right while you spread your legs and take it?”

She just closed her eyes and started breathing harder and moving faster.

“And with the blinds open even. Someone could walk by right now, and you know what they would see? Your naked body being pounded while your tits just bounce back and forth.”

She started grunting harder, and I could feel myself starting to boil. I wish I had porn star stamina sometimes, but porn stars don’t look like her and they don’t have sex like we do. As we were both getting ready to come, I could have sworn I saw motion out of the side of my vision at the window. A shadow briefly moved across the bed, which normally would have startled me during sex, but I was coming now and so was she.

“Fuck, fuck, fuck…”, I said as I emptied myself in her. She’s not usually one for bad language, but under the circumstances, it was all I was thinking. She came hard with a little whimper and kept it up for an unusually long time.

As we lay there feeling rather proud of ourselves, kissing and laughing softly, she said, “I thought I saw the light in the room flicker a bit.” I wanted to tell her that I thought someone had walked by and possibly spent a little time at our window, but I didn’t want to freak her out and have a celibate rest of the vacation. So I chose my words very carefully. “Well, I mean, I guess it’s possible that someone walked by on their way to breakfast or something, but it seems unlikely.”

“Oh. Well, they probably got an unexpected surprise this morning!”

All I could think was, “What the hell?”


We were not in a hurry to go down to the main area for breakfast, so it was close to 9:30 by the time we straggled in. I actually don’t mind sharing tables for hotel breakfasts with folks I’ve never met, but the place had mostly cleared out, so we took an empty table and sat down to eat. My wife is a relatively fearless eater by the standards of most women. She makes it clear that she doesn’t exercise to look like a supermodel, she exercises for the sake of waffles. Between the two of us gobbling down our favorite meal of the day, and our somewhat loud and animated conversation, we did not look like a couple of introverted people who wanted to be left alone.

At some point, there was a really attractive woman and her husband at the breakfast spread not far from our table, and she was looking over at us and smiling and it seemed that she was genuinely enjoying our happiness and occasionally making eye contact with us. As loud as we were talking, she couldn’t help but be part of the conversation. At some point, I saw her very slightly struggling with the DIY waffle maker.

Being the gallant gentleman that I am, I got up, covered the approximately 5 feet between us and said, “Did you need some help with that? I am the local waffle expert.”

“Is that really a thing,” she said.

“Oh sure. I actually have a degree in waffleology from Breakfast University.”

She smirked in a way that it wasn’t clear whether she thought I was vaguely amusing or was a mental patient that must be avoided at all costs.

“You’ve probably never heard of it. It was sort of a party school.” But I proceeded to get her waffle started while engaging in a small chat with her and her husband. By the time the waffle was done, we had all spoken a few words to each other, and my wife, ever the proper social animal, invited them to sit with us. If it was just me, I probably would have continued behaving like an ass, but fortunately my wife did proper introductions.

“My name is Jennifer and my husband’s name is Jim. And despite his behavior, he’s a normal guy who actually does make good waffles.”

Our new guest, clearly happy that we appeared to be actually nice people, said, “I’m Olivia and this is my husband, Ken.” He smiled and raised his coffee mug to acknowledge his wife while biting into a bagel.

We all started chatting about the place, not in a particularly substantive way, but still all enjoying ourselves. Olivia had a dignified and commanding manner about her, but not so dignified that it was off-putting. It didn’t help that she had shoulder-length dark brown hair and a face that you couldn’t stop looking at. She was wearing a relatively modest top, but there was a suggestion of some slightly larger than average breasts there that, I needed to remind myself, belonged to someone who was not my wife.

It was nice to meet friendly people since chatting with strangers in person has become a bit of a lost art. The gals were doing most of the talking while Ken and I understood our conversational support roles. At some point, it turned out that both Ken and my wife were physicians, and the conversation dynamic shifted to Jennifer and Ken talking about medicine while Olivia and I had small side conversations. It was looking like a nice harmless breakfast when the conversation began to take a weird turn.

“Hopefully we’ll see you around more”, my wife said. And she meant it. She’s always looking for folks to hang out with.

“Actually”, Olivia said, jumping back into the conversation with Jennifer, “I think we are neighbors. Aren’t you in the other side of our duplex, #203?”

“Yes!” said my wife, happy that fate was conspiring to get her some company for the trip. “How did you know we were there?”

There was a pause. A very slight pause, but a pause nonetheless. “Oh, I think I’ve seen you coming and going.”

And then, even subtler than the pause, was another smirk from Olivia. People are good at lying with their words, but not nearly as good as with their faces. I think we would have noticed them around the bungalow, and Jennifer would certainly have introduced herself. And we really hadn’t been getting out all that much. Then it hit me, we were having breakfast with a woman who, perhaps only briefly, had seen us fucking like rabbits. She had seen my cock driving in and out of my wife’s pussy, and now she was sitting there drinking coffee, talking about some of the shops just off the property and smiling like nothing was going on. And smirking.

Ken, on the other hand, seemed oblivious and clearly wasn’t going to let this story go down easy like a good husband. Lost in thought, he said, “When? We just got here late last night, and we haven’t been out at all except for your quick trip to get us some coffee this morning.”

“Ken, we have next door neighbors that you probably couldn’t pick out of a police line-up.”, Olivia said with a laugh, albeit a kind one. Ken just smiled, properly chastened, and went back to his bagel.

Unfortunately, I have an almost dog-like ability to wear my emotions on my face, and Olivia had clearly noticed that my mind was racing and that I was putting two and two together. And there was again just a slight crack of a smile there that the others didn’t notice. She had seen us, but clearly was not traumatized by the experience. She almost seemed to be reveling in it a bit, or at least reveling in my very slight surprise. Meanwhile, Ken and Jennifer carried on like long-time colleagues.

After my brain had processed all Olivia’s revelations, which really only took a few seconds, I quickly realized that an extremely hot woman had watched my wife and I have sex, and was actively chatting with us and trying to get to know us better. A better man than me would have more dignity than to say this, but knowing she was watching me at my best was totally turning me on. But knowing that she had no problem watching us and that my wife was quickly making a new friend really had the gears in my head turning.

Olivia eventually made some polite excuses for her and Ken to go back to their room. Ken seemed to be pretty clueless as to what that would be for, but he followed along rather obediently. Jennifer kept dragging out the conversation with Ken as Olivia was moving them towards the door, but eventually they exchanged phone numbers and made vague plans for us all to get together later.

Jennifer and I finished up in a slightly more leisurely fashion but eventually started making our way back to the bungalow. On the way back Jennifer continued to be delighted that we had started making friends here and talked fairly animatedly about some of the things that Ken had said. I didn’t really think anything of this as Jennifer seems to be everyone’s friend after speaking with them for 5 minutes.

We got back to the room, sat down, and checked out the website of the hotel to see which of the activities we wanted to be sure to do while we were here. Jennifer is a little more of a fan of the structured activities while I’m just a little more the sort to either wander around or hang out by the pool. I was going to be good with anything she wanted although I was really hoping we wouldn’t get over-scheduled.

Nothing really caught my eye until I saw the massages. They had the normal sorts of choices, but they also had the increasingly popular ‘couple’s massage’, where a couple can get massages together. I was totally down for that, but my wife had never really been a big fan of massages. I’m not sure if that was because she was conservative or just had had a bad experience before. But I threw out the idea, hoping she might bite.

“Hmm… I’m not sure. I’ve never really figured out how it’s supposed to work and what clothes you are supposed to keep on or when you get undressed or things like that.”

“I don’t think there are hard and fast rules about things, and I think they’ll be happy to explain anything or answer any questions. We can’t be the first folks to wander in there without a clue.”

“And you’d be okay if I wanted a guy to give me a massage?” she asked, smiling. She’s pretty naive, but she knew the answer to that one.

“Of course. And if it makes you feel better, there will be a woman with her hands all over my body too,” I joked. I’ve never heard her express interest in that being something she’d find hot, but I had a feeling it would appeal to her sense of fairness.

“Sure, we can do that then. But then I get to pick something too.” Yes, because I’m sure she’ll be suffering with my first choice of activities.

As we browsed through the website, I saw her stop on the page for their gift shop. It had the normal sundries and souvenirs, but it also had clothing. “Maybe we should hit the store right now and look around. They probably aren’t busy right now and it might be nice to have some chocolate laying around.”

“Sure”, I said, “and a bottle of wine for the room might be nice for the nights we don’t feel like going out.” Nothing like provisioning the room if one of the nights turned out to be movies and chill.

So we headed down to the shop. I was pleasantly surprised by how nice it was. It was big enough that they had a number of separate sections. The snacks and drinks were near the front, and shopping like a guy, I thought that we’d be in and out of here in 30 seconds. But my wife just wandered in and started looking around. I had known her long enough that that neither surprised me or bothered me. She likes browsing and I’m happy to hang out and look around.

What did surprise me, however, was that we eventually wound up in the clothing section of the gift shop. And then a bigger surprise, we wound up looking at the swimwear. We didn’t need swimwear. We had packed for a warm-weather vacation, so we were good, right?

“I worry that the suit I brought isn’t quite what everyone else is wearing. I’d hate to stand out.”

Okay. That second comment was totally Jennifer, but not where she was going with this.

“Everyone else we saw in the hot tub last night was wearing a bikini. Maybe I should try to find one that looks good on a fifty-something, if that wouldn’t be too weird.”

“You know I have no problem with that. I’m happy to help you pick one out.”

She laughed. “Yeah, that’s very noble of you, helping a woman pick out a bikini. I’m not sure I can trust you to do what’s in my best interest.”

“Not in your best interest? I can assure you I’ll be thinking of you the whole time I look at these.”

“How about I pick and then you can vote?”

I resigned myself to being a mere consultant in the process, but looking at the suits, there were only two options for her: hot and hotter.

She spent quite a while going through the suits, evaluating them mentally and trying to figure out the right size. Eventually, she decided on either a smallish white one or an even smaller blue one.

“Okay, here are the choices, what do you think?”

“Well, the blue one is smaller, but because your skin is a little darker, the white one will probably look better on you.” Look at me, being a great husband, suggesting the white one. The thin, unlined white one.

“That’s what I was thinking too. This one’s a little more appropriate for someone my age.”


We scheduled the couples massage for one o’clock and spent lunchtime walking around the property and down to the beach nearby. I love being around the ocean and we waded through the shallows since the water was warm. It was just nice having the two of us chatting and getting a vacation vibe going. It also helped normalize the notion that, on the whole, women don’t wear much around here.

As it got closer to our scheduled time, we headed back to the room and Jennifer started struggling with the what-to-wear question again for the massage.

“Well, I don’t know anyone here, and don’t really care, so I’ll be in the buff”, I said, hoping that she’d follow.

“I figured that was your plan, but I don’t know if that’s helpful for me.”

I didn’t have a good idea for how I might win this battle, and decided to hit the bar on the way over for a consolation prize. That turned out to be a good decision. A large, cold glass of wine for a warm afternoon was enough to even tempt Jennifer, and as usual, she helped herself to more than half of it.

We got to the spa area and were shown into a small but beautiful room that clearly impressed my wife. We met our two masseuses, Elena and Paco. I’m sure that they were good at what they did, but they also qualified in the looks department too. Elena was a little older, probably in her mid 30’s, and very pretty, with a nice smile. She had on a relatively tight tank top and shorts and it was hard not to think I had done pretty good with my choice.

Paco, however, was probably more of a looker though I can’t really judge that as a guy. But he was bronzed and fairly buff without looking ridiculous. He chatted up Jennifer a bit in a very casual but professional manner, and I think that relaxed her though the wine didn’t hurt.

The clothes thing was still bugging her a bit, and she eventually got enough courage to bring that up with Paco. “I should probably leave my underwear on, right?”

Paco, probably having heard this before, said, “You can do whatever you feel comfortable with. We just want people to enjoy themselves, so keep your underwear on if you want.” I had kind of hoped for a little more pushback from Paco, so I gave him a tiny glance to indicate that wasn’t quite what I was hoping for him to say.

“But,” Paco continued, “it’s easier for me if you take them off. I’d feel terrible if the oil ruined them.” Yes! He probably didn’t realize, but he was appealing to her sense of being nice.

“Oh, that’s a good point. I hadn’t thought of that.”

Elena and Paco left the room to let us get undressed and explained that we should just lie down on our stomach with the towel covering us and they’d be back soon.

We got undressed, and it was kind of hot seeing Jennifer get naked in an unfamiliar, somewhat public place. My body was beginning to betray itself and she just gave me a humorously disapproving look and told me to put the towel on her to make sure it was covering her completely before I covered myself up. The towel was just big enough to cover the distance from her ass to most of the way to the top of her back.

Not long after, our masseuses knocked, checked that we were ready, and then came in. They both got to work on our neck and back area, and for Jennifer that meant folding down the towel. Despite the fact that I had just seen her naked, seeing her laying there with the sides of her tits very exposed and a young man rubbing oil all over her back and sides caused me to become unbelievably hard after a couple of minutes, almost uncomfortably so. I tried to sort of lift myself up a bit so my dick could get itself in a less awkward position without anyone noticing, but in the quiet stillness of the spa area, I imagine it was obvious to everyone in the room what I was doing.

At some point, they returned the towels to their original positions and moved down to start on our legs. That felt amazing. I thought that the back massage would be my favorite part, but I had clearly never had a good foot massage. Jennifer seemed to be feeling the same way, and she had started to moan very softly and contentedly.

After the feet, they both started working their way up our legs which also felt nice. However, at this point I started watching Paco move his hands up her legs to the edge of the towel. I was loving the fact that because it was a ‘massage’, it was totally okay for this handsome young man to be rubbing oil on my wife’s thighs. I was worried that my wife was going to start getting very uncomfortable with this, but the look on her face was definitely not one of discomfort.

I was keeping my body very still because I was worried that, as hard as I was, I didn’t want to set myself off in possibly the most embarrassing moment of my life. I was watching Paco’s hands creep higher and higher and the fact that Jennifer just kept smiling was killing me. It certainly didn’t help that I had a hot woman’s hands inches from my dick, but honestly, watching my wife had my full attention. Nominally, you could argue Paco was massaging her glutes, my brain was just aware that he had his hands on her ass. I couldn’t believe my shy wife didn’t have a problem with that. Technically his hands were ‘under’ the towel, but that poor towel was not meant to cover a nicely-sized ass and a couple of large male forearms. She had to know he could see her.

Fortunately, Elena and Paco were both professionals. Soon, they stopped and asked us to turn over. I wasn’t sure how Jennifer was going to do this, but it wasn’t complicated. Paco lifted up the towel and she turned over. He made a show of keeping it low to preserve her modesty, but it wasn’t that low, and Jennifer didn’t seem concerned about modesty all that much at this point. I think I saw her tits, and he was lifting the towel from his side. And she hadn’t stopped smiling. There had to be some compromise on how he put the towel on her when she was laying on her back, and the compromise was that the upper part of her tits were showing. God, did she look good.

I, on the other hand, just had to grin and bear it. I had a rock hard erection that hid under a hotel towel about as well as you could imagine. Jennifer almost laughed when she opened her eyes and looked over in my direction, but our masseuses mostly stayed professional. Elena’s look was less disgust than an amused, ‘not again’ look. There is no way I was the first person to be in this situation.

Since they were at our feet they started working their way back up our legs, and given that shins don’t need much of a massage, they quickly found their way back up our thighs. They had carefully folded the towel over a bit so that each of us had our legs exposed such that they could get better access to our upper leg. Well, Elena had very carefully folded the towel for obvious reasons. I couldn’t completely see what Paco was doing but there was a lot more towel folded over. There is no way that he couldn’t at least see part of her bush and who knows what else. He had both hands around her thigh and seemed to be rubbing from the bottom to the top, without a lot of concern about what was on top. Jennifer was breathing more heavily at this point and had a little less of a smile, but that look clearly did not say ‘stop’. At some point, they switched sides and he kept up the rubbing. On one hand, I couldn’t see quite as much since he was on the side closer to me now, but I could basically see that he had her thigh in his hand and he was picking it up a little, so he could have more control. Her leg was being lifted and spread out a little and I don’t know how the towel was doing its job.

At this point, I basically had to have Elena stop doing my thighs as the towel was basically rubbing my dick, and there was no way I could take this. I was hoping that she thought that my leg was getting sore, but she probably knew exactly what was going on.

Finally, they moved to the head of the table, to finish the massage. Paco had gone to wash his hands first, which seemed odd since he was just going to get oil on them again anyway. Soon they were both doing our scalp, which was unexpected to me, but felt great and helped me calm down again after watching Paco manhandle my wife. I thought that I might actually survive this with a little dignity. After massaging my scalp, Elena said, “What would you like to finish with, your pectorals or arms?”

I wasn’t really thinking there was a wrong answer to that question, so I just said, “Pecs sound fine.” I was feeling mellow and agreeable at this point.

Elena looked over at Paco and said, “Okay, we’ll do pecs”.

Wait, I thought, was this the plural, “you”? Was she asking for both of us? What’s that mean for Paco and Jennifer? Does Jennifer get a say in this?

It appears that the answer to the final question was no. Elena and Paco moved their respective hands down our necks and then down to our upper chests. As good as that felt, I had to glance over to see if that was happening to Jennifer too, and the answer to that question was yes. It was still a fairly modest exercise on the other table, but the slight rocking back and forth from the rubbing was not doing her towel any favors. I swear that it almost looked like her barely covered nipples were pushing the towel down her body every time Paco rubbed back and forth and that the towel was losing that battle as Paco’s hands moved closer and closer to some of the finest tits on the planet.

I still kept thinking about how there is no way Jennifer could be comfortable with this. She was starting to get tense, but it wasn’t an uncomfortable type of tense. She was grabbing the edge of the table, but she was definitely not nervous.

At some point, Elena was still finishing up rubbing me and had worked her way down to my chest, which was fine, but I had been focused on the other table. Paco, on the other hand, seemed to pull the towel up a little bit, and I felt myself mostly relieved but just a little disappointed.

But then it happened, and I don’t think Jennifer or I was expecting it. Paco put a little more oil on his hands, carefully slid them under the towel and started massaging her pectoral region. Except those muscles were covered with her tits, and topped with nipples that I had seen clearly poking through the towel. He tried to make it look professional, but he was a young man with strong slippery hands and they were going back and forth on my wife’s tits. Back and forth. The towel was there, but it might have well not been. You could even hear it as his slippery fingers rolled over my wife’s tits over and over.

I thought it was going to be too much for me, but in the end it was too much for Jennifer. She tried to not make a sound, she tried to act like nothing was happening, but she wasn’t fooling anyone but herself. She was coming, and she was coming in front of strangers, and one was a handsome young man whom she had known less than an hour who was half massaging her and half feeling her up like a total slut.

Eventually, her orgasm subsided and the massage was over. Paco and Elena quickly washed up and told us that we were free to use the shower in the room to clean up before we left, and that they didn’t have another massage for a while so we could take our time.

I got up and went to her side, but she was quiet. I took her by the hand and we walked over to the shower and turned it on. She was still not saying anything and I didn’t know exactly what she was thinking.

“Hey, are you okay?”

“Did you… see?”

“Did I see you come? Oh God yes, I saw it.”

“I was so embarrassed. I can’t believe I came. I can’t believe he rubbed his hands on my tits. I can’t believe I let him. I can’t believe YOU let him. You put me in this situation. It wasn’t my fault.”

She was holding on to me tight, our slick bodies rubbing together as she sorted this through.

“There was nothing wrong with that. You were enjoying yourself. A lot. I was enjoying myself. And Paco was sure as fuck enjoying himself.”

She had to laugh briefly at that. “What was he thinking, a young man like that feeling up an old woman?” She was starting to relax a bit as she understood that I was good with what happened.

“Do you want to know the truth? He was hard as a rock when he hurried out of here. I bet he’s probably done jacking off already thinking about your legs in the air and his dick in your pussy.”

She started smiling a little more, “I guess MAYBE. He is a young man, and they do get excited by just about anything. Maybe even an older woman.”

“I thought you were totally hot, and you looked like he’d have paid you for that massage instead of the other way around.”

“So you’re sure you’re not mad at me?”

Okay, at this point she had to know I was not mad, but if she wanted to hear me say it, I was happy to say it. I mean, I was smiling, about to explode, holding her fucking hot body against mine while I talked in detail about what was possibly the hottest thing we had ever done.

“Well, okay then, I suppose I can get just one more thing off my chest then.”

“What’s that?”

“You know how Paco had to go wash his hands after massaging my legs?” she said, less guiltily and more seductively. “While he was rubbing my thighs, the sides of his hands kept bumping into my pussy. He tried to make it seem accidental, but I’m sure it wasn’t. The more he was rubbing the more he kept hitting it, rubbing across it, rubbing across my clit and just moving over and over my pussy more and more. I almost came then, and I was so wet that his hands must have been a mess. I’m sure he didn’t want to take all that juice from my pussy and have it wind up on my face.”

As she described the lurid details with words that rarely came out of her mouth, I came. I came and I came as my dick rubbed all over her body and came all over her stomach, hip, and even the hair around her pussy. I came so much that she looked sort of like she had been gang-banged, until the shower water washed it all down her leg in what was one of the sexiest images I had ever seen.

“Well, it looks like you were okay with it, and if it makes you happy then that’s what’s important to me,” she said, probably even half-convincing herself.


We spent the afternoon napping, with Jennifer watching TV. I know that seems a little lame considering we were at a nice resort, but we were happy and just wanted to hang out in a comfy bed together for a while. At some point, Jennifer texted with Olivia to let them know that while this afternoon was probably going to be a bust for getting together, dinner might be fun. We agreed to get together at six for dinner, which would hopefully avoid the crush between around 6:30 or 7.

Jennifer started to talk about what she was going to wear. She had changed back into just a dress and panties after the massage and was trying to figure out what was the right thing for dinner here at the resort. I thought she looked good in what she had on and was probably dressed appropriately for a casual dinner, which was my honest opinion. She pushed back and said that she should at least put on a bra, to which I replied that no one is really going to notice. Given the relatively thin dress she was wearing, that was a slightly less honest opinion. It was not at all see-through, but it was no match for her determined nipples this afternoon She almost never went braless at home, but due to some combination of laziness and possibly something else, she grudgingly conceded the argument, but made it clear that she wasn’t convinced that a bra wasn’t necessary.

We got to the restaurant just a minute or two before them, and they seemed happy to see us. I think they had had a chance to process meeting us for breakfast and decided that we were certainly harmless and possibly more fun than eating alone. We joked that we were worrying about them standing us up, and Ken volunteered that Olivia had spent quite a bit of time talking about us this afternoon. Olivia looked at him sharply as if to say, “Shut up!”, but then laughed and said, “Meeting new people is part of the fun of being on vacation.”

We sat opposite them, with Olivia across from me and Jennifer across from Ken. That was roughly in line with the flow of conversation although much of the talk was really the four of us. Jennifer and Ken wound up steering the conversation towards medicine and keeping up the lion’s share of the talking. Ken was definitely taken by Jennifer’s simple, happy charm. While Olivia was easy to warm up to due to her having remarkably good looks and confident charm, I was starting to also think Ken was pretty great. He was easy to talk with, and wasn’t shy about admiring Jennifer’s shapely breasts. We had a lot in common.

Dinner was light and sped by thanks to the pleasant conversation with our new friends. After a couple of glasses of wine each, we were feeling even better than when we started. Olivia suggested we let someone else have the table, and instead grab the hot tub before it got too busy. Olivia was not only gorgeous, but she could read my mind.

I think that Jennifer might have been a little more apprehensive if I had suggested jumping in the hot tub with them so fast, but with Olivia asking, it seemed more like a girls’ night out. That would have been great by itself, but the dynamic was very slowly evolving to be her and Ken hanging out, with Olivia and me tagging along – and I considered that even better. Jennifer was feeling more comfortable talking with both of them about a wide variety of subjects, while Olivia and I spoke less but seemed to be getting along well. In a world of people who are increasingly growing more isolated, she wasn’t afraid to make eye contact and smile when I made some pretty mediocre attempts to be charming. I’m really not a star with the ladies, but I think she at least appreciated that I was incompetent but genuine.

Jennifer and I went back to the room to change. I’m a guy, so I took off my clothes, put on my trunks and was ready to go before Jennifer had really gotten started. Jennifer was still trying to get the tags off of her suit, so I volunteered to help with that so that she could get undressed. (Hey, what can I say, I’m a nice guy.)

After she got undressed she was standing there holding the suit, straightening out the pieces before she put them on. And I was just sitting there looking at her naked, holding the suit and thinking, “Oh man. She’s going to put that into that. That’s going to be so fucking hot.” And let me tell you, I was right. She stood by the mirror to look at herself, and you could almost hear the gears clicking in her head where she was trying to find some way to complain about it. But it was impossible. Eventually, she just cracked a little smile and came over to put on her sandals.

Unfortunately, we didn’t have anything in the robe family to wear. I had approximately zero concern for that for myself, but Jennifer grabbed one of my T-shirts to wear to be a little modest. She went from looking like a MILF swimsuit model to a hot woman who was walking around in a t-shirt and panties. You can’t hide hot.

And speaking of not hiding hot, we got to the hot tub just as Ken and Olivia were getting in. For Ken, this consisted of stepping down a couple of the stairs and plopping down with a little more splash than you’d expect, drawing a disapproving glance from the more dignified Olivia who was making her way in a little more carefully. My wife on the other hand was amused and was watching Ken closely. Unlike most of us men who get slightly less handsome when undressed, he was quietly carrying a fit body around under his clothes. Jennifer noticed this too.

Much to my enjoyment, Olivia was taking her time standing there before descending into the water. She had mostly been wearing slightly upscale but modest clothing so far, but now she had on a dark red bikini that was practically painted on. It advertised her breasts better than a neon sign. Previous clothing choices had not done her breasts justice. They were pretty large compared to Jennifer’s, but the bikini was clearly some engineering marvel that made them sit up tall and just a little more exposed than they needed to be. I stared for what was possibly a criminal amount of time until she turned around to both get in and let me get on with breathing. Olivia didn’t indicate any obvious displeasure with this, and Jennifer just lightly snickered.

It was just the four of us for a while, and that was really nice. We had settled into our little piece of the resort right, and it was like we owned the place. The hot tub had a decent amount of space and we had spread out quite a bit with the guys across from each other and the girls also. We were mostly submerged and feeling very mellow. At some point I was wanting to get another drink, but I didn’t want to spoil the moment.

Pretty soon, two other couples showed up, and they showed up at a funny time. Although the initial conversations were shared among the group, we had once again degenerated into Jennifer and Ken talking, with me chatting Olivia up. The other two couples entered the hot tub where they thought they were keeping the existing couples together, but they wound up first splitting Jennifer and I up, and then splitting up Ken and Olivia. So now there were four couples in the hot tub, but not quite the right ones. This was mostly lost on Jennifer as she was talking to Ken quite animatedly about something, but it was not lost on Olivia and me. Partially, it was because the situation was just kind of amusing. But it also was not really a hot tub for a large number of people to spread out in.

Olivia and I were pressed together for the first time, and I had this beautiful but unfamiliar half-naked woman sitting next to me with our legs and sides pressed together. We exchanged a brief smile when our fellow soakers pushed us together, but she just kept up the conversation with everyone else as if nothing had happened. I, however, was desperately trying to figure out what to do with my hands and arms. I wound up scrunching them into my lap, and looking really ridiculous and awkward in the process, which is exactly what I was trying to avoid. At some point, Olivia took my right hand in her left and let us both rest our clasped hands on our legs. In some way, this was much more relaxing. In a small way, it was in the comforting hand of a new friend.

In a much larger way, a hot woman had her hand on my thigh, and I immediately started to get hard. This wasn’t a big deal since I was under water, but it didn’t look like I was going to be getting my drink any time soon in the shape I was in.

Ken came to the rescue. “Hey, there are lots of drinks in this hot tub, but some of us are getting left out of the fun!” He asked Jennifer if she wanted anything, and she was on the fence. He looked at Olivia and me, and I said, “Margarita, rocks,” and Olivia indicated that worked for her also. Ken then turned back to Jennifer and suggested she should come with him to see if she could make up her mind at the bar, and also to have some help carrying back the drinks.

Jennifer, always the helpful one, thought that was a great plan. She and Ken got out at the same time. Ken, wearing modern men’s swim trunks that had about 30 sq. ft. of fabric, proceeded to take about 3 gallons of water out with him, which was amusing. Jennifer, on the other hand, emerged from the hot tub, and the conversation came to a stop. As it turns out, I had made a pretty good decision with her bikini. While not totally see-through, it wasn’t exactly opaque when wet. She got up and gave the group a quick wave, and somewhat jokingly said, “Save our seats,” but in the process, she gave us a display usually reserved for wet T-shirt contests. Her nipples and areolas were clearly visible, and the younger woman to the right of Olivia was somewhat shocked by this and was clearly not good at hiding that.

At some point, my wife was going to have to look down, but now she was going to wander through the crowd, up to the bar, and order some drinks essentially topless. Oh man. I was so hoping that she didn’t notice. It might ruin the vacation. But for now it was the hottest thing I could imagine.

Olivia, you could tell, clearly noticed, but didn’t say a word. She just kept on smiling and carrying on with her conversations. My biggest worry was Ken. I didn’t think he had the wherewithal to have that conversation with Jennifer, but I also didn’t think there was anything in his experience with being a guy that could keep his jaw off the floor.

With the two of them gone temporarily, the atmosphere subtly changed between Olivia and me. We leaned into each other, more like a real couple than two people trying to pretend like we were not a couple. We began chatting with each other a bit, and not to the whole crowd. And our faces were getting much closer to each other than a non-couple ought to be.

“Are you enjoying yourself here at the resort?” I asked, a little tongue-tied and bewitched to have her so close to me, but desperate to cover up my nervousness.

“Very much. There is a sense of freedom on vacation that doesn’t really exist at home.”

“That’s what we were going for also. Just a chance to let loose.”

“Yes, I’ve definitely noticed that.”

“I thought you had noticed. You don’t seem terribly scandalized by seeing two people having sex.”

“Scandalized? Not so much. Surprised to see a couple going at it in front of an uncovered large window in a public space? Maybe a little.”

“Well, sorry to surprise you in that case.”

“Surprises aren’t always a bad thing,” she said as she moved slightly away.

Well, so much for trying to get the upper hand in that conversation, as she left me speechless. I was wondering why she had said something like that and then pulled away, but she was once again one step ahead of me and had noticed our spouses coming back. Given that my half-naked wife had gone off with her husband for a few minutes, I’m not sure what the protocol was, but she was probably right playing it cool with them.

Jennifer’s suit had dried a little bit and wasn’t quite so explicit in its display. They both had two drinks in each hand and came over to hand them to us. As they bent down to give us our drinks, I saw that poor Ken was getting hard. Jennifer had to be getting to him. He quickly jumped back into the hot tub with Jennifer getting in a little more carefully. After spending so much time engaged in conversation with Ken, she actually took an extended look at Olivia and me, and gave me a look that, while ambiguous, clearly did not mean, “You are in trouble, Mister.”

With the drinks now in hand, we were back to talking with the larger group, with a nice mix of drinking and conversation. Jennifer and Ken gota little more comfortable in each other’s space, and Olivia and I became more relaxed too. When the other two couples eventually said their goodbyes, we were now in this pairing where the wrong couples were coupled up with each other for no particular good reason, but no one seemed to be in a hurry to change that.

Eventually the drinks were finished and things started to get quieter. I was trying to figure out what the next move would be that could keep things going when Jennifer declared somewhat abruptly, “I think we need to turn in. It’s been a long day.” It was a statement, not a question, and it very quickly broke the mood and made the whole odd seating pattern seem awkward all of the sudden.

We all got up quickly, and it was starting to look like things were going a bit sour as we were taking the long walk back to the shared bungalow together, but before we went in our door, Olivia went over to Jennifer and gave her a quick hug and said, “It was really wonderful having dinner and just hanging out with the two of you. Hopefully we’ll see you around later.” And with that, Jennifer immediately brightened back up and the mood lightened.

We went back inside and hung up our swimsuits to dry. Jennifer was quiet, especially by her standards, and I was worried I was going to hear about the swimsuit I had helped pick out or my unnecessarily close seating with Olivia. Instead, we just crawled into bed and got in our normal position where we were lying close to each other, with me on my back and her on her side. We were in our normal sleepwear. Jennifer in her panties and me in nothing. Everything was totally normal.

“Wasn’t that sort of weird that you and Olivia were sitting together and Ken and I wound up sitting together?”

“Yeah,” I said carefully, “that was kind of funny.”

“I mean, we weren’t doing anything wrong, right? Neither one of us.”

“Nope. Just hanging out in the hot tub.”

“Was Olivia feeling okay? It looked like you were holding her hand under the water.”

“I think that something about the crowd and dinner was unsettling to her.”

“I was worried earlier that she was mad at me for monopolizing Ken so much.”

She was more worried about herself. “I don’t know why you would think that. You didn’t do anything wrong.”

“Well, it’s just that Ken seemed to be checking me out quite a bit, especially when we were going and getting drinks. And when we sat back down, he had his hand on my thigh. But I guess they are probably just friendly people.”

“I thought tonight was great, and I hope you enjoyed the attention. Even if it was drifting into flirting a little, all of us were together and everyone seemed to be having a good time. I don’t think anyone meant any harm.”

“No, I guess you are probably right. I probably shouldn’t have chased them off. I don’t know what made me think those things.”

“It’s okay. They’re great folks. There was nothing sexual about it.” I probably didn’t need to add that part, especially since at least on my end it was a lie, and there is no way that Ken wasn’t starting to have inappropriate thoughts about Jennifer. But it was the type of statement that no one was going to have any way to verify, so I said it to make her feel better.

I was pretty good with all of the harmless fun during the evening that had followed up the excitement of the afternoon’s massage. But it didn’t look like I was going to get lucky tonight unless something radically changed.

And then we heard them. It wasn’t quite like they were in the same room as us, but the walls were obviously pretty thin. At first it was just quiet bed movement and some tell-tale moans. I didn’t say anything to Jennifer as I worried it would give her a chance to say that we shouldn’t be listening. But I did hold her hand just a little tighter. As it turns out, Jennifer was smiling and everything was good.

Jennifer even volunteered, “That’s sort of sweet, they are having sex. They must have enjoyed the night with us also.”

I couldn’t resist pulling on this thread a bit. “Well, I’m guessing that Ken saw enough of your body tonight that he probably ripped Olivia’s clothes off her as soon as they hit the room.”

“What? Oh, please. Olivia is gorgeous and younger than me. You are just a lecherous old man and think Ken is too,” she joked.

But then we started hearing them talk. As they started fucking harder, the bed was moving harder and it was a lot easier to hear them.

“Oh God, Ken, that is so fucking good. It’s been forever since you took me like this.” Olivia did not sound like nice Olivia. She sounded like a bad girl, and I was getting hard fast. The whole thing was so hot. “I bet it was Jennifer that got you so worked up, wasn’t it?

Jennifer froze up. Holy freaking shit, did Olivia just say that? We probably shouldn’t be listening to this, but I was hard as a rock. I was listening to the woman that had spent the evening getting me hard, and now she was getting drilled by her husband and bringing up my wife? Oh, man.

They continued to pound hard, and the moans and the slamming bed sounds were getting to be too much for me. I pulled down Jennifer’s panties and climbed on top of her in an instant. I’m a nice guy, but this wasn’t the time to ask politely. After years of fucking this woman, I knew exactly where I was going and drove my dick home hard and fast.

She didn’t tell me to stop, she didn’t ask what the hell I was doing, she just said, “Shhh….” I got the hint and started fucking her with long, slow strokes.

Ken and Olivia were increasing the pace, but Olivia wanted more. Evidently I wasn’t the only one getting off a little on their spouse getting off with someone else.

“Oh God, Ken… Just fucking say it. Say it. Say it was Jennifer. You know she looks hot. She’s sweet but she’s one of those women that are totally fuckable. She looks fuckable, and you heard them this morning.”

The moment of truth. Was this conversation going to bother Jennifer?

She was moving under me with her hips with mine to make things go faster, which was not like her. But she was sloppy wet, and was starting to make noises of her own.

“Oh fuck, oh fuck, I’m getting so close, Ken. I bet they’re fucking right next to us. Jennifer is probably on her back with her tits bouncing around like a total slut… so fucking hot. I saw her this morning through the window, and she was taking it like a tramp. Oh God, he was drilling her… so fucking good.”

I don’t know when they started fucking, but this was getting to be too much for me already, even having emptied my balls all over Jennifer earlier in the afternoon. Jennifer said loudly, “Don’t stop… don’t stop… don’t stop…” as she neared the edge.

And then, as if we needed any help, Ken finally blurted out, “Yeah, Jennifer. Take my dick! Take my dick, you little slut!” This put Olivia over the edge and she started screaming incoherently. “Yeah, come on my cock, Jennifer, and I’ll come in your pussy like all you teasing sluts deserve! I’ll fill you up. Oh God, oh God…” – at which point he let out a long series of grunts and clearly emptied into Olivia.

But more importantly, listening to Ken talking about fucking Jennifer hard sent Jennifer way over the edge. She had her head to the side, and I don’t know if she was ashamed or just flailing about as she was coming, but she had a look on her face like I had never seen before. She was making this loud mewling noise that was unbelievably hot and unrestrained as she unabashedly came and came in a very non-Jennifer fashion. That put me over the edge of course, and I watched her thrash while I pumped a load into her that matched her orgasm.

We collapsed together, catching our breath and enjoying the fact that a couple of nice, polite middle-aged people like ourselves had just done some world-class fucking. As we cooled down, I was expecting Jennifer to go back into embarrassed, good-girl mode, but instead she just kept the smile on her face as we slowly drifted off. Not long before we both fell asleep, I heard her say softly, “Can you believe that people actually think I’m some sort of tramp to get off to?”

Was this my wife?


We slept great, thanks to the sex, and woke up relatively late the next morning. We didn’t go down for breakfast and instead just hung out in bed watching people fix up homes on TV. We didn’t have cable at home so my wife considered what were fairly mediocre home renovation shows to be a bit of a fun treat. I think she might have been a little nervous about facing Ken and Olivia after the dueling sex business the previous night, but if she was uncomfortable, she didn’t show it at all. It was a little surprising to see her let loose like she did yesterday, but it was wonderful to not see too much of the guilt afterwards. That had always been one of her sticking points. After being even a little bit of a bad girl, she’d have a guilt trip afterwards. But now, things seemed to be building on each other. I was determined to keep the momentum going.

The day was looking a little cloudy, but still warm. I had wanted to hit the beach to swim and be outside a little more as long as we were in paradise, but Jennifer wasn’t really one for sunbathing or swimming. Much of that was because of the sun, and years of medical school had caused her to fear being out in the sun too long. I managed to convince her to hang out at the beach since it was cloudy, and mentioned that I’d go back and grab some lunch if she got hungry. She had a book that she had hoped to read while on break and that sealed the deal.

The part of the beach associated with the resort was relatively small. There was a decent crowd there so people were situated closer to each other than we were expecting. Since it was early, we had no trouble finding a couple of chairs though. People were just starting to fill in the spaces.

When we were walking the first evening, I had noticed that part of the beach had some hand-painted signs that said ‘NO NUDITY’ on one line, and then, ‘Topless OK’ on the next. I laughed to myself at that because topless is definitely OK in my book. Jennifer had never gone topless before and had pushed back against it in the past when I had suggested it. I thought about mentioning it when we first grabbed our chairs, but I had had more success this trip letting things take their course and thought I’d look out for a good opportunity to get her out of her bikini top.

I went into the ocean and swam a while, enjoying the sensation of the warm salt water. I love the ocean and the fact that it’s easier to float because of the salt. I’ve had people tell me that it’s all in my head but that’s fine with me. I also love the fact that the ocean just goes on as far as the eye can see. It gives a great sense of being enveloped by nature. And it didn’t hurt that there were a number of women enjoying the water also. Not a lot, but enough smiling, wet, barely dressed bodies that I really didn’t want to get out.

After a while, I did want to check on my wife. As I walked back from the water, I saw that it was getting significantly busier. It was the afternoon and people had started bringing drinks down to the beach, giving it a little more of a fun vibe. Most importantly, the toplessness had also started. It wasn’t a majority of the women by any means, but it was still probably at least a dozen women who had the girls out. It was awesome. I don’t think women know how they can make a man’s day by just letting us take a look every once in a while.

Jennifer was just reading though, pretty much as I had left her, lying on her back and getting into her book. I noticed that she had started chatting with the folks around her, which is pure Jennifer. It was mostly couples, although there were also a few groups of younger guys and younger girls who were there also. Jennifer was mostly chatting with the couples that were our age and seemed to be enjoying the company.

My wife decided to take me up on my offer to go back and grab some food. I was really enjoying the beach and slightly regretted making that promise. “I guess I can go back and get us some food and drinks – but you owe me.”

I smiled to soften the words, and she laughed. “Okay, fine,” she said. “What do I owe you for walking all that way and bringing back a sandwich.”

“Well,” I said with a grin, “you could go topless.”

As expected, I got the world’s largest eye roll. “I’m not sure those are equivalent.” But she was still smiling.

“Hey, don’t do it for me. Do it for all the guys out here. Consider it a charitable donation to the welfare of men everywhere on the beach.”

The older couple next to us that Jennifer had been talking to couldn’t help but overhear our conversation. The woman commented that she had promised her husband she’d do it once and it would count as his birthday present this year. And if Jennifer would do it, it would make it easier for her.

More eye rolling, but you could tell that if she could do someone a favor, then that would help it happen. “Fine, but your husband is getting quite the present this year.”

Both women reached behind to undo their tops. You’d think that I’d be watching my wife’s new friend, but I had waited too long in my life to not watch my wife do the deed. There she was, taking off her top like I’d seen her do a thousand times before. But this time, she was outside in a decent crowd. It was magnificent. And her friend didn’t look too bad either. This was turning out to be a fucking great day.

I’m sure I was staring at both of them when my wife rather tersely said, “Well, where’s my lunch.” Oh right. Lunch. I hated to leave, but a deal is a deal. And she’d look just as good when I got back.

I headed back up to the property, and got a large sandwich for us to split, a mai-tai and a sparkling water since I didn’t know whether she would want to indulge a little or was just thirsty.

As I made my way back, I had a little trouble finding where we had settled down earlier. Something didn’t seem right. Where I thought we were sitting was a crowd. As I got closer, there was my wife, surrounded by a small crowd of young men who were engaging her in conversation. What was going on here?

It seemed that they were all having an animated discussion about the book my wife was reading. At least that was the pretense. These guys did not look like the local book club, but they sure were hanging on everything Jennifer was saying. It must have been fascinating, because they never looked away.

After I returned, the guys somewhat awkwardly made their way back down to the beach to a group of young women who were more their age, but not confident enough to shed their tops. I wanted to ask what exactly had transpire, but didn’t know where to start.

Jennifer looked a little guilty. “Those guys sure had a lot of questions about this book. They just kept asking and asking about this and that. I didn’t want to spoil it for them if they were that interested and I was trying to be helpful, but everything I said just led to more questions.”

Was she serious? Her tits were holding a very public showing around a bunch of horny young men, and she thought it was about the book? Even her new friend had to hold back a guffaw when Jennifer attempted that explanation. I noticed that her fairly attractive friend was able to keep her tits to herself just fine, but somehow my wife had “accidentally” attracted an audience of guys that happened to hang around for a lecture. She’s naive, but she’s not that naive.

That was all a little weird, but at some point I just sat back and enjoyed food, drink and breasts. It turned out that Jennifer was both thirsty and in the mood for something boozy, so I scored some points with the drink order. The neighboring couple excused themselves to go back for a nap, and we settled in for a little more relaxation. Jennifer went back to her book, and I did one more dip in the sea. She didn’t cover herself back up after our friends left, so every guy on the beach got a birthday present for themselves that afternoon.

We eventually went back to the room around half-past two. We put our stuff down on the table, and I pulled her close for a quick kiss. “Hey, you looked great out there. Thanks for doing that for me. This will be a very memorable vacation.” I didn’t know if anything like that would ever happen again, so I wanted to make sure she knew I appreciated it and to give her some positive reinforcement before the moment slipped away. Turns out, the moment wasn’t going anywhere.

“Did you really think that was okay, me taking off my top?”

“Of course. What could possibly make you think that it wasn’t?”

“Well, I mean, most of the women were just laying there, but I had started talking to a couple of the young women about the book, and the guys followed them over to me. I really was just trying to talk to the women.”

“I was wondering what was happening there.”

“And at some point, the women wandered off and the guys were still hanging around chatting with me while I was practically naked. And they were just checking out my boobs, not really trying to hide it. I didn’t want to be rude and say something. What do you even say in that situation?”

“Yeah, I’m not sure what you should have done.”

She was still pressed up against me at this point and could tell I was getting painfully hard hearing her talk about this. Her hand moved to the front of my trunks and outlined my huge erection.

She smiled. “Too many tits out there today?” She had no idea that I was just thinking of hers and the whole world enjoying them. “I can do something about that.”

Jennifer pulled down my trunks and gave the tip of my dick and nice slow suck. This is not typical Jennifer, but it felt so good.

“I guess I’m not really doing anything right now that a slut wouldn’t do. Showing my tits to a bunch of guys, and now I’m blowing one of them. Good thing it’s you, right? I mean, I could tell that most of those guys were big and hard while they were looking at me. They were staring at my tits, but I was a little bad looking at the outlines of their cocks in their trunks. All hard for me.”

Oh fuck that was so hot to hear her say that.

“You know, I’m just a little excited too. Maybe you could help me out while I finish you off. And then I promise to try to not be such a slut.”

I ripped her bikini off, picked her up, threw her on the couch so that her feet were away from me and her head was right where it needed to be. We didn’t 69 very often, but we had no trouble getting into a position where I was on top of her with my dick was in her mouth. I headed straight for her pussy.

I would not have described her as, “a little excited”. My sweet wife was running like a faucet. I dove into that pussy and it was wet. Usually she likes her clit to be gently licked, but she was pushing her whole pussy in my face like her life depended on it. All the while she was giving me a really sloppy blowjob. And honestly, it wasn’t a great blowjob, but this wasn’t about me, this was about her getting herself off after this afternoon, and I think the blowjob was just an excuse to get her pussy eaten.

It would be great to say that we both came at the same time, but I can’t tell you how hot her talk had gotten me. Despite the fact that my dick was basically just fucking her mouth while she was focused on getting off, I got there first. I came hard. Some of it wound up in her mouth, but a lot of it just wound up everywhere on her lips, her cheeks and other places on her face.

She wasn’t far behind when she started panting, “Oh God, faster, faster,” only it was a bit slurred because she had my cum all over her mouth and lips. But she didn’t care and kept up the noises until they became a little incomprehensible.


She screamed out one last muffled scream and her legs clamped together like a vice. I had just gotten my head out of the danger zone, but my hand was still there with a couple of fingers buried in her pussy. It hurt my hand a little, but it was so fucking sexy to see her react like that.

She was moaning for quite a while and then she finally relaxed her muscles. Usually after a rare 69 session, she’s quick to get up and clean up, but she was just laying there looking like this strange combination of angel and slut. It was beautiful, and it was hot. She eventually got up without a word and went to take a shower. I was hoping we’d get a chance to talk a bit so I could tell her how amazing she was, but now I was worried she was just a little embarrassed about this interaction. We were definitely on a roll as far as her pushing way past her boundaries. I didn’t want anything to hold her back.

She took a long shower, and I was expecting her to be a bit sheepish afterwards. Instead, she just plopped beside me on the couch right next to me and grabbed my hand with her right hand, and the TV remote with her left hand and turned on a cooking show, settling in next to me.


We were very lazily watching TV for a couple of hours, half-napping in the process when we got a text from Olivia on the group text for the four of us asking if we wanted to do a slightly early dinner with them tonight so we could hit the resort club/bar and do some dancing. We were both game for this. I think Jennifer was just having a blast hanging out with new friends. I was thinking more that between Jennifer and hopefully Olivia, I would feel like I had won the dance partner lottery.

Dinner was once again great. The conversation flowed, with lots of light touching and flirting by the girls. Olivia was a bit more restrained, but more intentional with her flirting. Jennifer, on the other hand, felt so comfortable with Ken that she was just carrying on with him like a teenager. Since it was early, it was mostly older folks at the tables around us giving us disapproving looks, but we were having too much fun to care.

Olivia was wearing a thin dress that was modest by the bikini standards that seemed to be quite popular at the resort. By dress standards, though, it was hot. The straps that came down from the neck got wider as they covered her breasts, but not that wide. Olivia’s breasts were not small enough for this to be simple and dignified either. Those pieces of cloth were not quite covering the sides of her tits, exposing a beautiful roundness on both the inside and outside. It wasn’t trampy, just hot.

Jennifer hadn’t really thought too much about what would be a good outfit for dancing. Olivia’s outfit set the bar a little higher than the casual clothes she was wearing. When we were done with dinner and two bottles of wine, Jennifer said that she wanted to change into something more fun for dancing. She surprised me a bit when she asked Olivia to come with her to pick something out. I know that’s what a lot of women do, but that wasn’t like Jennifer. Also, it’s not as if we had brought a ton of clothes with us, so there weren’t a lot of choices for her.

That left Ken and I to talk for what I’m sure was not going to be a quick trip for the two gals. Part of me wanted to bring up the whole big picture of what he thought of the closeness between the opposite spouses that seemed to be developing. But how do you bring that up? I saw the primary outcome of such a conversation to be possibly ruining everything through awkwardness. So, we kept the conversation light and talked about the kids, work and some wonderful day in the future when retirement was a possibility. It turned out that this was a great conversation to have. There was nothing about the exchange with Ken that made me think he was anything but just a great guy, and I was strangely happy that Jennifer was getting along so well with him. Of course, the conversation that Jennifer and I had heard through the wall while he and Olivia were having sex was not lost from my mind. Part of him very much realized that he thought Jennifer would be great as more than a friend, but he never said anything remotely creepy. And there was nothing that made me think she was upset with all the attention I was paying to Olivia.

When Jennifer and Olivia returned, I did a double take. Jennifer was wearing an outfit I didn’t recognize. I was hesitant to say something and possibly get myself into trouble for not recognizing an outfit that she had bought and showed me, but she quickly volunteered that Olivia had offered to loan her one of her dresses. It was a small, black spaghetti strap number that probably fit her a little tighter than it should since Olivia was a bit thinner than Jennifer. Jennifer seemed to be reveling in it though. She didn’t really have anything like that at home, so I was impressed with her confidence to wear it. I wasn’t sure how much of it was her getting bolder or the wine at dinner, but she wasn’t going to get any complaints from me.

“You look great,” I said. She did, and I wanted to encourage her.

“Don’t I?” she said with a giggle. It looked like she wanted to tell me something, but we were already headed into the club.

It was early, and we had no trouble getting a table and drinks. We were downing the first round and feeling very little pain when Jennifer grabbed my hand and pulled me to the floor, with Ken and Olivia soon following. Jennifer and I don’t dance much, but after a few drinks, everyone is a dancer. We were enjoying ourselves thoroughly when Jennifer came a little closer to me and said, “So you like the dress?”

I just smiled and nodded.

“It’s a little tight.”

“Tight looks good on you.”

“It’s way too tight for any of the bras I brought.”

“I’m totally okay with that,” I said, probably a little more eager than appropriate.

“But guess what else?”


“Olivia said I couldn’t wear it with any of the underwear that I brought. She wouldn’t let me leave without seeing what it looked like without the underwear. So I just took it off while we were standing there just to see what it would look like. I wasn’t actually going to not wear underwear, but she just told me that it was perfect and practically pushed me out the door!”

Wow. I was impressed that Olivia pulled that off, but Olivia’s skills were becoming less and less surprising. I’m not sure where she was going with all of this, but it seemed that Olivia and I were pushing in the same direction.

“So now I’m stuck here wearing nothing but a tight dress while my panties are sitting on the floor of someone else’s room.” She laughed about that, which was a good sign. “I wonder what Ken is going to think of that?” Her voice was more playful than concerned.

I smiled, but mostly I thought that you will never see those underwear again if Ken finds them.

I usually like to down a few drinks before hitting the floor, but seeing as how we were well into the alcohol phase of the night and feeling fine and the music was playing, we stepped out onto the floor and found a place that we could dance. We didn’t have any problem finding a place for the four of us on the floor since it was early. There were only a few other people dancing, so we probably stood out, but we didn’t care. The combination of being slightly older and slightly drunk meant that we were very capable of having a rocking good time without giving a crap about what other people were thinking. And if other people were thinking something, it was that those two chicks were totally hot.

At some point, we took a break and headed to a table to cool off with another well-deserved round of drinks. We had gotten in some serious exercise moving around like we did, and the women had a bit of a sheen about them that looked ridiculously sexy. Jennifer was sitting next to me, but Olivia was sitting across from me. The sides of Olivia’s breasts were glistening and it was impossible to look her in her eyes for more than a couple of seconds at a time. Jennifer had cleavage that was also drawing the attention of Ken and I, but it was a little harder for me to casually glance at my wife’s breasts without totally turning my head. And as far as I was concerned, it was their job to distract Ken while I was checking out his wife.

We talked and laughed while we worked on our drinks. Ken and I each had a whiskey sour and we were feeling a little mellower than before. Jennifer and Olivia were both drinking white wine, which seemed to be more like Gatorade to them, because after the break, they were ready for us to dance more. I have never said no to a beautiful woman in my life and wasn’t about to start.

The club was quickly filling up at this point, and the floor was more crowded. As we got up from the table, Ken and Olivia came out from either side of the table and wound up closer to Jennifer and me, respectively, than they were to each other. As we worked our way through the crowd onto the floor, we were separated, Ken with Jennifer and me with Olivia. This seemed to be happening a lot this weekend, and as usual, we just went with the flow. I started dancing with Olivia and pretty soon we found ourselves separated from our spouses with the throng of other dancers giving us a little privacy.

For someone whom I would have best described as somewhat dignified in most of our interactions, she was starting to show some serious sexpot vibes. She was moving like a woman who knew she was hot, and she was starting to dance a lot closer to me than she was before. Really close. Lots and lots of incidental contact. I was trying to be coolly receptive, but I was clearly getting worked up by Olivia.

At some point, we were getting pinned increasingly close to each other by the crowd. Her face was getting closer to mine, and my heart was starting to race. I wasn’t sure where she was going with this, but she just wanted to have a quick conversation.

“You look like you are enjoying yourself,” she said with a not very innocent smile.

I smiled back. “Of course. What guy wouldn’t enjoy dancing with you.” I wasn’t sure where she was heading, so I thought I’d keep it safe.

“Good. I like to see my friends happy,” she said in a slightly conspiratorial way. “And I haven’t seen Ken and Jennifer in a while. They are probably enjoying themselves also.”

I didn’t quite know what her agenda was, but it was clear that having Jennifer and Ken spend some quality time together was not a problem at all. Again, I didn’t know for sure if I was all-in on this, but I was clearly not that bothered and wanted to see where she was taking this.

“I certainly hope they are having fun. We seemed to have lost them in the crowd, but they are big kids. I think they can take care of themselves for a while.” I laughed a bit as I said this, hoping that she would run with it.

“I think it is great for a man to be so supportive of his wife having fun without watching over her all of the time. You sound like a great husband.”

“What about you? Ken seems to have no problem with you getting lost on the dance floor for quite a while with a man who can’t keep his eyes off of you.”

“Ken is not going to complain about anything as long as a pretty girl is paying attention to him. He’s a great guy, but he’s a guy.” She pulled in a little closer to me, and our bodies were now touching. I was trying to keep from getting too close so she couldn’t feel me getting hard, but that might have just made it more glaringly obvious that I was having a problem.

“I’ve always thought it would be fun if Ken could open up a little more, but I’ve never really noticed him move in that direction – until I saw Jennifer. Your sweet little wife is exactly Ken’s kryptonite. She’s clearly got him wrapped around her finger. I don’t think that was her plan, but now that she’s got him hooked, I think she’s enjoying it.”

I hadn’t really thought of it that way, but accidentally seducing a guy would appeal to her sense of being desired without actually looking like she had done anything wrong. And so far, no one had called her on it. And the ‘accidental’ part was starting to slowly slip away. Between the attention from Ken and listening to Ken and Olivia talking about her while they were fucking their brains out, I think Jennifer was moving from just being drunk on wine to being drunk on the power of having Ken desire her.

While I was sorting this out Olivia and I were getting closer. We were still moving, but now my hands were around her waist, and her arms were around my waist. Slowly, she moved her hands to my neck to pull my head a little closer to hers. This was causing her breasts to slide up my chest a little, and I had given up on trying to hide how hard I was. If she was going to play this game, I was assuming that she knew that a hard dick was going to be part of it and she wasn’t going to run screaming. As she pushed her crotch against mine, she smiled and pulled my head closer.

“I think if Ken and Jennifer can figure things out, then we can all win this game,” she said in my ear with her lips touching me. I was getting so turned on by her. I had mentally bought into this scenario a long time ago, but at this point I would have begged Jennifer to fuck Ken right on the dance floor if I thought she would do it. But I wasn’t sure if Jennifer was quite where I was. Getting turned on is one thing, but having a nice girl like Jennifer let herself have sex with a guy she just met is quite different.

“They might need a little bit more help,” Olivia said, “but I think we can give them a push if you are willing to work with me a bit. Let’s go check on them.” As she spoke, her tongue was now touching my ear. I don’t quite think she realized how close I was to just carrying her off to the room and not giving a shit about what our spouses thought. She was killing me.

We worked our way through the crowd to where we thought they might be. It took a while to find them as they seemed to be hiding from our eyes. But it was clear the dynamic had changed a little. Jennifer was no longer in a fun, giggly mood. She was now in full vixen mode. She had her arms in the air with her chest thrust forward just a little, and her ass pushed back a little. Ken was behind her, not quite touching her, but staring at her with a look of lust on his face. The dancing was just barely defensible as something two friends might do for fun, but they were about to cross a line.

We had stopped to watch them, our bodies pressed close together and arms around each other’s waists, when Jennifer saw us and immediately stopped dancing and looked a little guilty. Olivia and I were careful to give her a big smile, and Olivia immediately spoke up. “God, you look so good out there dancing. I wish I had your natural charm. I can’t believe Ken wasn’t all over you!” She finished that off with a genuine laugh and smile such that Jennifer immediately became her happy self again.

“Oh please, I’m just a middle-aged woman out here having some silly fun far away from home. You guys are so nice indulging me.”

“By the look on Ken’s face, I don’t think he’s just being nice. And I’ve been monopolizing your man also for a while. But I don’t want to wear these nice guys out so soon. How about we go back to our room and have a nightcap there. It’s getting a little loud and crowded here, and it’s hard to chat.”

No one had to be convinced that a break was a good idea, so we went back to the room. This time though, we were walking with each other’s spouses and no one was being shy about it. Olivia and I were walking closely with our arms around each other, while Jennifer was basically hanging off of Ken in a way that was a little more than friendly. Ken looked like he was king of the world with Jennifer hanging on him like she was.

We got back to their room and Olivia told them to have a seat while she asked me to help her with glasses and wine from the kitchenette. It didn’t take us long to open the wine and get the glasses, but Olivia gave me one quick kiss on the ear and asked, “Are you good?” I smiled and nodded. I was not quite sure where she was going with all of this, but she had clearly executed her role as the puppet master perfectly so far and I wasn’t going to stop her now.

As we walked towards the couch Jennifer slid over closer to Ken to make room for us, but Olivia changed her path at the last minute and offered me the chair. I wasn’t sure how this was going to work, but I was following her lead at this point. Olivia sat on the floor and leaned against the front of the chair.

We chatted and laughed about some of the things that we had done so far to compare notes about the resort. Olivia volunteered that they had spent some time checking out the beach and had availed itself of its features. “It was so hot a couple of days ago that it felt great to let my boobs out for a while.”

“Sorry I missed that,” I volunteered, trying to keep the conversation light, but also looking down the front of Olivia’s dress and letting my mind fill in the blanks.

“That’s okay. Ken seemed to be doing enough looking around for everyone,” Olivia teased, clearly in fun.

“Hey, I was just comparing everyone to you and realized that you had the nicest ones at the resort.” That Ken was pretty good.

“Did you make it down to the beach?” Olivia asked.

I smiled, “Oh yeah, we were down there earlier, weren’t we hon?” I laughed a bit, trying to draw Jennifer in. She might need a little encouragement to tell her story. But she just gave me a look that wasn’t mad, but she clearly wasn’t going to be drawn in so easily.

“I really think Jennifer was enjoying herself there. She was chatting with a few folks about one of the books she brought, and being the great speaker that she is, after a couple of minutes she had a large crowd of young men hanging on her every word.” I gave Jennifer an evil smile after that last sentence, hoping to get a rise out of her, but she just smiled and didn’t say anything.

Fortunately, Olivia jumped in. “Hmm… I’m assuming you had some visual aids that accompanied your story, Jennifer. Or do you have a speaking style that captivates young men?”

At this point we were all laughing and Jennifer was forced to jump in and defend herself. “Hey, going topless was more Jim’s idea than mine! And I can’t help it if I’m ‘captivating’ in the right environment.” She tried to look embarrassed, but you could tell she was pretty proud of herself.

“Did you really have a crowd?” Ken asked, clearly delighted by this story.

“Well, it probably wasn’t a ‘crowd’ as Jim would say, but when you are just sitting there with your boobs on display for the first time in your life in front of a bunch of young guys, it seems like a whole lot.”

“Wow,” said Olivia, clearly impressed. “I’m clearly the amateur here when it comes to laying out in the sun. I’m sorry I missed it. I could have learned something.”

“YOU’RE sorry you missed it?!?” Ken said in an exaggerated fashion. “So basically, every guy at the place has seen your assets, and after spending all this time with you guys, I get nothing? That seems unfair.”

Jennifer just smiled. Ken was close, but that wasn’t quite going to get it. It was killing me that we were just on the edge. Oh please, Olivia, Do something.

“Well, it seems like our tits have been on display to a bunch of potential weirdos that we don’t know, and I’m just about sweating to death after dancing so much. So if no one minds, I’m going to pull these straps down and give the girls some air. Last chance for complaints?”

Oh man, this was it. I think the whole crowd knew I was not going to complain. And Jennifer would never tell someone what to do, although she might make an excuse and leave. Ken, however, was not whooping and hollering and cheering like I thought he ought to. There was just a little pause, and I worried that the whole thing would come crashing down.

And then, against all odds, the miracle occurred. Jennifer spoke up. “Of course. It’s not a big deal at all, Olivia. And what kind of friend would I be if I wasn’t supportive. I’m kind of sticky in this tight dress myself, so if you’ll do it, I’ll do it. I’m just drunk enough and feel bad that Ken didn’t get to see the show yesterday. But you two guys better be thankful for this.

Olivia was right. It all revolved around Jennifer. If she was in, everything would work out.

And then it happened. Without any further ado, Olivia slipped the straps of her dress down off of her shoulders and pulled it down to her waist. It was glorious to see those tits for the first time. I would have considered her tits one the great highlights of the decade in any event, but wanting to see them so bad and finally getting them was great. And they were indeed great. They had a natural beauty to them and hung down just slightly, capped with some very hard nipples. She was clearly enjoying the attention and looking forward to anything that might happen next.

Jennifer, on the other hand, didn’t quite have a dress that could slip down so easily. It was tight on her, and a bit sweaty from the dancing. She stopped for a second, trying to figure out how to pull the dress down without doing damage to the goods, when I made a very generous offer. “Ken, could you do her a big favor and unzip the back of her dress?”

My wife gave me a look that was half smile and half glare, for me being so bold as to offer the honor of undressing her to another man, but she didn’t hesitate to turn her back to Ken. And Ken hesitated even less to do the honors. He unzipped the dress most of the way down her back and then moved back a bit to await the fruits of his labor.

All eyes were on Jennifer as she grabbed the front of her dress and pulled it down just a little more slowly than necessary, soaking in the attention just a little bit before the big reveal. Ken was staring a little more than necessary, but who could blame him. Olivia even seemed to start smiling a little bigger, possibly in admiration, but more likely in anticipation of her plan coming together. And watching my wife undress in such an intimate setting was making me hard as a rock. Have I mentioned how good she looks?

“Ta-da!” she said, thrusting her arms out and trying to cut the sexual tension in the room with a little levity. We all honored the gesture and clapped for her and she seemed to be happy with her situation despite what seemed like a minor case of nerves at first. She settled back into her previous spot next to Ken, although now she was leaning on him and his arm was around her lower back. They were looking quite cozy with each other. Of course, I wasn’t doing too bad with Olivia sitting on the ground between my legs while I sat on the chair.

We continued to chat, talking a little bit about our lives back home, while the women sat there with their dresses pulled down and their tits enjoying night air while we guys enjoyed the view. At some point we all needed a bathroom break so in a brief moment where I wasn’t totally hard, I excused myself. When I returned, I took off my shirt.

Olivia decided to take her turn, so I offered her a hand up which she gladly accepted. This left her walking around with a dress rather awkwardly hanging around her waist and legs. When she returned, she walked out holding the dress and wearing just her underwear. We all stopped talking as she approached in nothing but black lace panties that were mostly transparent, especially if you were staring like me. She explained that she felt dumb wearing the dress around her waist, and asked if we minded. I think she knew the answer from the guys. Jennifer just giggled.

Ken went next and returned sans shirt, and then all eyes were on Jennifer. She had her dress around her waist and nothing else and I wasn’t sure where she was going to go with this. “Somebody needs to find my underwear that I left in here when I got dressed. There is no way I’m walking around buck naked.” I didn’t like the second part, but it sounded like she was okay with dressing down just a little bit more, which was progress. Olivia volunteered to go hunt down her underwear in the bedroom while Jennifer went to the bathroom.

This left Ken and I alone in the room for a minute. We didn’t say anything but at some point we exchanged a smile and knew he was good to go for just about anything. But like me, I think he was prepared to let Olivia drive.

Jennifer emerged from the bathroom looking a lot like she left and Olivia returned shortly afterwards, having struck out on her errand. “I’m not sure where your skivvies ran off to, but they have to be in there somewhere. Why don’t you see if you can make Ken do something useful this evening and see if he can find them in there while Gus and I open another bottle.” Nicely done Olivia.

Olivia and I wandered into the kitchen and put a little more distance between us and our spouses. I was getting ridiculously horny after spending all of this time with the mostly naked women, and as soon as we wandered into the kitchen I pulled Olivia into me, pressing her breasts against my chest and leaning into her for what I thought was going to be a much-deserved make out session. She didn’t resist my embrace, but once again put her mouth next to my ear and whispered, “So how long do you think they will be in there?”

Honestly, I had briefly forgotten about Jennifer and Ken due to the fact that I was good with Jennifer doing what she wanted and well, Olivia. I was starting to see that Olivia’s game was more focused on Ken and Jennifer and less on herself. But the Ken and Jennifer game was clearly getting her off so I wasn’t too worried.

“Unfortunately, I can’t imagine that it will take too long to find a pair of panties in a hotel bedroom. So we probably don’t have a lot of time.” Give me something Olivia, just a few seconds, because you are killing me.

“They might be a while. It depends on how well I hid them and how much time they want to spend on their appointed task.”

Shit, she was good.

“I appreciate your patience. It will be rewarded, let me assure you, if Jennifer is good with it. I think she will be.” For the first time, I felt her hands roam up my back to my neck and pull my head down a bit and pull my head into hers. She pressed her lips to mine and quickly used her tongue to open me up. After decades of being good, I felt totally like a teenager making out with the hottest girl at school. A total sexpot standing around in an almost non-existent pair of underwear was making out with me while my dick was essentially trying to fuck her through my shorts. And she was totally getting into it. It was amazing.

I didn’t really have a plan but my hands did and were starting to work their way into her underwear. But after way too short of a time, Olivia pulled away and said, “I don’t hear Jennifer and Ken. What do you think they are up to?”

“Hmm… Not sure. It depends on how good Ken is at getting Jennifer warmed up.”

“I may have given him a few pointers.”

“Sounds like none of this was accidental.”

“Fate needs a bit of a nudge every once in a while and the minute I saw Jennifer, I didn’t want to let this opportunity get away.”

“Sounds like you are okay with Ken enjoying himself.”

“Okay with it? I have been waiting for a long time to watch Ken fuck someone else. It’s taken a long time to warm Ken up to the idea and a much longer time to find the right situation. And that situation is Jennifer.”

“You sound like a really great wife. But I’m hoping this isn’t a totally selfless experience.”

“Oh hell no.” She moved her hand to the obvious bulge in the front of my pants. “You are part of the equation also.”

The nearly naked nymph was totally driving me crazy, but she asked a good question. What was Jennifer up to? I had a feeling that the Jennifer/Ken question wasn’t just a rhetorical one for Olivia. I put my hand around Olivia’s ass and gave her one last kiss and a grind against her crotch and we quietly made our way towards the bedroom door.

We could hear Jennifer and Ken talking softly. They didn’t seem to be obviously making a lot of noise, but they weren’t exactly whispering at this point. The notion that somehow one of the four of us was going to get upset easily had long since slipped from our minds.

“Ken, what do you think you are doing?” Jennifer said with a slight laugh.

“Just doing my part to help with the search.”

“My underwear aren’t lost on my body, and yet that seems to be where your hands and eyes wind up.”

“Well, they don’t seem to be anywhere in the room and this seems to be the next best place to search.”

“I appreciate your enthusiasm, I really do, but we probably shouldn’t be doing this.”

“My hands were all over you when we were dancing. And if I recall, yours were roaming freely also.”

“That was different. We were surrounded by people. That way we couldn’t go too far. Right now I’m standing here topless with my dress around my waist and your hands roaming around my boobs and ass.” I gave Olivia a squeeze when I heard Jennifer say that. Olivia just smiled.

“So you don’t like what I’m doing?” Ken said fairly quietly

“That’s not the problem. You are making it hard to be good with your hands on my body and your lips on my ear. Mmm… very hard… and Jim and Olivia are probably in the other room wondering about us. What if they walked in here?”

“What if? I don’t hear them, so whatever they are doing, it doesn’t involve a lot of talking. I’m thinking they are not too concerned. And deep down, I don’t think you are too concerned either.”

“I’m trying to be concerned about them,” she said without much conviction but with a somewhat labored breathing. “But I’m a little focused on your hands and where they seem to be going.”

I couldn’t help myself. I had to take a look. Fortunately, they both had their backs to the door, with Ken standing behind Jennifer with his arms around her. One of his hands was slowly stroking her nipples, but one seemed to be slowly reaching under the bottom of her dress. Jennifer’s head was leaned back into Ken and his mouth was against her ear.

Suddenly, Jennifer let out a low moan that she cut off as if she was embarrassed by her own response. “Ken, what are you doing?”

“Oh damn, Jennifer. Your pussy feels so good. So fucking wet. Let me just rub it for a little while. Please.”

“Oh God. I’m not usually like this.” She didn’t say no.

“You look so fucking hot right now, and feel so good. Just enjoy it. Let me enjoy it.”

She was leaning into him and breathing hard. Her hand had reached down to grab his ass and press him against her harder. Ken was clearly rubbing his hard dick against her ass while he played with her. Olivia was watching them play and had a hand down her panties. I was almost afraid to touch myself. I was so close to coming, but I needed relief.

Jennifer was clearly driving herself crazy getting fingered by a very recently found friend while her husband and his wife were somewhere nearby. “Oh God. We should stop. You feel so good, but I don’t want to do this to Jim and Olivia.”

At this point, Olivia finally spoke up. “I think Jim and I are possibly enjoying this more than the two of you are.” Jennifer turned around startled, and, unusually for her, speechless. Olivia just deftly slid her panties down her legs and walked over to Jennifer and said, “The moment I saw you I wanted to see you with Ken. You are sweet, sexy and just once in my life I’d like to watch Ken fuck someone else, and it has to be you. Please do this for me. Please.”

Jennifer was still in a bit of a state of shock and looked to me. I’m not sure what I was supposed to say here. If she was looking for someone to defend her honor, I wasn’t the right person. She knew that this was one of my fantasies and I knew that while she hadn’t ever said it explicitly, it was hers too. I knew her well enough that she wanted this, but wanted a push.

I walked over to her, and pulled her dress down, leaving her naked. She looked beautiful, she looked sweet, but she also looked like sex. Olivia and I Ied her to the bed and sat her down on it. Olivia then walked over to Ken and removed his slacks and underwear. She finally got to see what she was doing to Ken. He looked painfully hard and was staring at Jennifer. I think seeing Ken’s dick made this very real very quickly for Jennifer.

Jennifer was starting to breathe heavily again, and was clearly getting worked up. But I think she still needed to be pushed into this to make it okay. And, I think, she was looking to Olivia and me for that push.

Olivia and I sat down on either side of her and slowly laid her down on the bed where she was mostly lying down but her legs were bent at the knee and hanging over the bed. Our arms were on her shoulders and breasts, not holding her down in a real way, just a symbolic one.

Ken walked over and stood between her legs, his cock leading the way. His legs were in between her thighs and as he first touched them, she gave a little bit of a twitch, closing against his legs just a little. He bent down, not far enough to fuck her, but just to rest his dick against her pussy. He slowly started rubbing it against her clit and pussy, quickly getting wet from Jennifer.

After all of the fingering early, and now having a hard dick teasing her, Jennifer was quickly getting as worked up as she was before. Except that now there was a dick just waiting to go in her. All she had to do was ask.

“Oh fuck… I shouldn’t do this, right… but you said it was okay, didn’t you?” She was slipping fast.

And it didn’t help that I had started fondling her breasts and Olivia had slid her hands down to her thigh. “Well, really, the decision is yours. You don’t have to do it,” said Olivia, having a little fun with the situation.

Meanwhile, Ken had placed the tip of his dick right at Jennifer’s opening, and she was grinding her pussy against the head.

Jennifer was moaning at this point. “But you all want me to do this right? You want me to get fucked by Ken, right?” She continued to squirm against his dick.

“I’d feel better to hear you say it was okay,” Olivia said, continuing the torture, but knowing just how this was going to end.

“Uhhnnnn… uhhnnnn… I guess… I guess… that… Ken can fuck meeeEEEE.”

Ken hadn’t waited for her to even finish the sentence before he buried his cock in her. I finally got to watch as my gorgeous wife got her wet pussy drilled hard by a strange cock.

This was not a sweet fuck. I think Ken knew that he was going to be coming soon and wanted to get as many strokes in as possible before that happened. She was getting fucked hard and fast. Her eyes were rolled back in her head and her tits were flopping around. It was everything I had hoped it would be.

It’s a testament to how hot my wife looked that I hadn’t noticed that Olivia had one hand on Jennifer’s thigh and another one between her legs moving around hurriedly while she knelt next to the bed. She was looking at me, but she wasn’t looking at my face. She was looking at the obscene bulge in my underwear with a face that made it clear that she needed it now.

I realized that my wife wasn’t the only totally hot woman in the room and quickly moved behind her. She raised her hips and spread her legs a bit to remove any doubt as to what she was asking for. I immediately pulled off my underwear and slid right into Olivia. That was the first new pussy I had had in decades, and it felt like it hadn’t in years. I was also so worked up that I wasn’t doing anything but fucking her hard, and I think that’s how she wanted it.

All four of us had spent so much time dreaming about this moment, and then working our way up to it all night that we weren’t going to last long. Surprisingly, the first person who came was Olivia. I guess she had clearly wanted this the most of all of us. At some point right before she came she took her hand off her clit and grabbed Jennifer’s thighs tight with both hands. She started seizing up and buried her head in Jennifer’s hip. As she started to come, she clearly had her eyes on the prize of the evening. “Keep fucking Jennifer… Fuck her harder… HARDER… UNNNNGGGGHHH.” As her pussy clamped down around me and I watched Jennifer get fucked hard, I unloaded hard in Olivia and just kept coming and coming. It was the most amazing experience.

Of course, this started a chain reaction where Ken was getting faster and faster and grunting louder and louder, and between Olivia grabbing her legs and Ken fucking her, she wasn’t going to last. She hadn’t been as vocal as Olivia, but Olivia looked towards Jennifer and said, “You look so fucking hot. Ken is about to come in your pussy Jennifer. He’s going to come hard because you look so fucking hot.”

And she lost it. “YESSSS… Ken… MAKE ME COME… FILL ME UP… MAKE ME COMMMM…” She was thrashing hard while Ken grabbed her hips and pulled her to him as he shot into her. If there was any doubt that I had wanted this, that moment made it all very clear that I did. It was a million times hotter than I could have possibly imagined. Even after everyone had come, there was still this wonderful feeling of sexual energy in the air now that the pretenses had all been removed and we could finally admit that we all just felt like horny teenagers for the moment with our new partners.

After Ken was done he left himself inside of Jennifer while he laid slightly on top of her and slightly to the side on his elbow. Her arms were around him and they were clearly luxuriating in the afterglow of the sex, trying to get their wits back about themselves.

Unfortunately, the rear entry position that I had with Olivia didn’t really lend itself to keeping coupled once I started to get a little soft. Olivia pulled off of me, and took my hand to lead me to the other side of Ken and Jennifer. She lay on her side right next to Jennifer while I was behind her, propped up on a pillow so I could see my wife also.

We were a little bit giggly as we made small talk. It was nice that no one seemed uncomfortable with having their spouse shagged by someone else. I’m sure it helped that everyone was getting some, and everyone was enjoying themselves. Olivia made a remark about having to pay for the top cover on the bed and that in hindsight we probably should have pulled it down. She rather scandalously called attention to her crotch and said, “I’m not sure what got into Jim, but his cum is just kind of spilling out of me everywhere. There is a huge wet spot around my legs.”

Women aren’t supposed to say things like that, and Olivia said it in such a way that it just sounded slutty. And then looking to where she was pointing and seeing the mess I caused just made it look more slutty. That was starting to affect me. Usually I need about an hour to get hard again, but with the scene in front of me, I could feel myself stirring not minutes after I had just come.

I wasn’t the only one. Olivia’s comments had made Jennifer giggle, but I could see Ken starting to move again. And by move, I mean move his dick, which was still inside of Jennifer.

It was a beautiful thing to watch now that we weren’t quite in the frenzy that we were in before. Olivia and I were both entranced by our spouses slowly starting to move together again, and this time, Jennifer clearly had gotten the message that tonight, everything was good.

“I think your husband thinks it’s time for another round,” Jennifer said to Olivia with a little bit of a smile.

“Well, your husband is being a little presumptuous also. I think he wants seconds too. I don’t know what we could have done this evening that would make our husbands think we are that kind of girl.”

Jennifer laughed out loud at this, almost dislodging Ken. “I’m having a little trouble believing that he is up again quite so fast.”

At this point, Olivia got up on her knees to expose me to everyone and made it clear that the two women in the room were again having an effect on me. “Look at this,” she said as she softly grabbed my swelling dick and began to stroke it gently. “Somehow there must be something in the room that he really likes.”

As she stroked me, Ken was being a little more intent with his fucking. He was taking long, slow strokes, clearly more confident that he could last for a while. And between Jennifer’s wet pussy and the fact that he had just emptied a bucket into her, there was no resistance, just a sloppy mess and a small smile on Jennifer’s face.

“Well,” said Olivia, “it looks like Ken is all ready to go, and Jim is only half way. I believe I have some pride at stake here.” I was assuming she was going to do some magic with her hands. Fortunately, I was wrong.

She rolled me over on my back, and then crawled between my legs. She took my half-hard dick and put the tip in her mouth and very slowly swirled her tongue around the head. I was in heaven. I love blowjobs that start when my dick isn’t full hard, and the whole thing fits nicely inside of a woman’s mouth. But the important thing is that my dick had just been inside of her pussy a short time ago. My wife had never done that for me, and I assume that most women wouldn’t do that. Olivia was clearly not most women. She had no problem with the fact that it was a recently fucked dick and was going to town on it.

When I was most of the way hard, Olivia slowly pulled her mouth off of me. Jennifer, though getting gently screwed by Ken, had actually been watching the whole blowjob intensely, probably thinking, “I can’t believe you put that in your mouth,” but clearly thinking it was hot.

Olivia looked at Jennifer now, clearly proud of her handiwork, smiled and said in a voice that sounded like a dare, “Did you want a try?”

Jennifer looked surprised, and didn’t immediately react. But Jennifer didn’t want to look like the coward and had occasionally indicated that two dicks at once was a fantasy of hers. So, she eventually smiled, and I didn’t wait to slide over and put my cock in her mouth. If she had concerns, she didn’t show them and started sucking on my cock with gusto. Maybe she was trying to outdo Olivia, but all that I knew was that very soon she was all-in on this blowjob.

I love a blowjob easily as much as the next guy, but this was special. This was my wife, who had always claimed she was a 10 out of 10 heterosexual, sucking on a cock that had recently been inside of another pussy. And her mouth was involuntarily bobbing back and forth as she was getting fucked.

I was a little jealous that Ken was getting fucked by my wife and I wasn’t getting fucked by his. Fortunately, Olivia seemed to be feeling that way also. This was my lucky day that not only did Olivia feel like another session, but she rolled me on my back and slid right down on me.

I thought maybe Olivia was trying to establish some dominance in the situation, or possibly trying to show off how hot she was. In any case, she was sliding herself up and down on me while I got to watch her amazing body fuck me. I had been too concerned with wondering how the night was going to go earlier that I didn’t really have the chance to take in how good looking she was without her clothes on. I was really starting to appreciate how hot she was and thinking that I must be some sort of sex god that she’d want to ride me.

At some point though, I understood what was happening. She was really getting into the sex, but she was sitting on top of me and watching Ken and Jennifer fuck. And at some point, they made the transition from nice, slow friendly sex to fucking. Ken was now totally back on top of her, and their bodies were pressed together. Jennifer had her hands on his ass and he was pistoning in and out of her with a slapping sound. She would never admit it, but I think that loud slapping of bodies together while fucking really gets her going. Ken and I were both a little more restrained than we were previously, and fortunately lasted a lot longer, but it was easy to see where this was heading.

As things started getting more intense, I had to look over at my wife and see if I could catch her in the act of coming. Like every woman, watching her come is amazingly hot. Usually she gets a bit of a blank stare before she comes and then closes her eyes, but they were open. They were open and they were watching Olivia bounce up and down on me. I believe her when she says she’s not interested in women, but watching Olivia ride me was something that was too beautiful not to look at.

I was nervous about being able to go two for two as far as making Olivia come, but I think of all us, she was probably feeding off the energy of all of the sex in the room more than anyone else. She was watching Ken fuck Jennifer while Jennifer watched Olivia fuck me. I felt a little like I was being used as a tool for her orgasms, and that made me feel like a million bucks.

At some point, she stopped bouncing so much and pushed her tits against me while she ground her clit on me while we fucked. You could tell she was getting closer and was interested in getting there at all costs. Ken was getting close too. I had a sense that I was going to outlast him this time, although to be fair, he’d had his dick in Jennifer non-stop for most of the past hour.

Sure enough, Ken went from confidence to coming in an instant. It’s usually like that for me the second time. You think you can last forever since you just came, and then at some point it just rolls over you out of nowhere. As he shouted Jennifer’s name out as he came, Olivia followed close behind him, pulling at my back and grinding herself into me.

All of these orgasms were getting me very close, and I was ready to start going full speed at Olivia, when she climbed off of me and said, “You should finish with Jennifer.”

I was not expecting that. I don’t think Ken was expecting that and I’m sure that Jennifer wasn’t. Ken was probably used to Olivia giving orders at this point in their marriage, and he just rolled off to the side and wound up with his knees on the floor beside the bed. Jennifer was just laying there, very worked up, but she hadn’t come. I don’t think she was thinking, “What kind of slut am I?” so much as, “Someone needs to get me off!” And Olivia had rolled off of me before I came.

A small part of me was thinking, do I really want fuck Jennifer right now? I mean, Ken has come in her not once but twice. But really, I wanted it. I wanted to fuck her because I was close and honestly needed to get myself off. I wanted to fuck her because I wanted her to be able to get off. But mostly, I wanted to fuck her because I wanted to stick my dick in her once-in-a-lifetime slutty pussy and make my contribution to the cause.

It goes without saying that I slid in effortlessly. It was a hot, wet mess, but it was my wife. After an evening focused around screwing the beautiful woman I had met only the day before, this was now about me and Jennifer. I felt it, and she felt it. I had had my fun, she had had some fun too, but this was about us. We had been fucking each other for decades, and we knew just what to do. It was messy, it was sloppy, but we both wanted each other so bad.

Ken and Olivia just watched from either side of us as I started fucking her hard. Ken had had her all night, but she was finishing with me and that was how it was going to end. I was fucking Jennifer hard, two people were watching, and Jennifer didn’t seem to give a shit. She was loud, she was obscene, and she was beautiful. As we got near the end, she started shouting, “Jim… Jim… Jim… Oh fuck… I’m coming, I’m coming… I’M COMMMMMING…” as if no one was watching, or maybe as if everyone in the world was watching. I came hard, and made her mine again. There were no bad feelings anywhere, but I wanted the audience to know she was mine.

And honestly, I think they were rooting for me. Everyone had gotten what they wanted this evening, and everyone was going to go home happy, except possibly the maid when it came time to clean the room.

Jennifer and I lay there in each other’s arms while Ken and Olivia got in bed and snuggled under the covers. At some point, we realized we were a little tiny bit cool, and that it was probably time to get up. Ken and Jennifer were ‘home’, but we had to gather our things and head back to our suite where the door was about 6 feet from the door to their suite.

Jennifer grabbed her original dress and put it on, leaving the borrowed dress from Olivia with them. I put on my pants and just held everything else in my hands. We left with a smile and a wave after a night that was life-changing. It was unlikely we were ever going to forget this, and I wasn’t sure what the proper thing to say after something like this. As we were going out the outer door, Jennifer quickly peeked back in the bedroom door and said, “Hopefully we’ll see you at breakfast tomorrow!” That was such a Jennifer thing to say.

We never did get her underwear back.

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