Making Friends on Vacation

"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.