Dianas First Time In Cabo

For our tenth-year wedding anniversary, my wife, Diana, and I decided to get away for a week in Cabo. Fears of the Covid pandemic had settled down and we had not had a vacation in quite some time. Having become so stir crazy during the quarantine and due to some financial problems, we were both way more excited to travel than we'd ever been. It was springtime and, with the weather becoming consistently sunny, we knew that the circumstances for a nice warm trip in Mexico was going to be ideal. In the days leading up to our trip, my wife told me she had bought us matching bathing suits and, as silly as it sounded, it was just another indication of how excited she was to spend some quality carefree time with me. I knew that five days in the sun, laying poolside, drinking tequila drinks with my oh so sexy wife, without a care in the world, would be amazing.

She pretends she's not, but Diana is extremely attractive, and I'm not alone in thinking that. Whenever we go out, I see the way men look at her. Women often make excuses and pretend these kinds of looks are not happening, but guys know guys, and I know guys are lusting after her. At 5-2, with a stunningly attractive face and a tight petite body and perfect tits, she hasn't lost anything through the years. And the very confident sexy way in which she carries herself turn heads, even when we are together. Sure, the guys are respectful of our relationship and don't usually make moves on her when I am there, but they all want to fuck her.

Diana and I had talked before about allowing her to indulge in being with another guy, so long as I am there, but she always said she wasn't into it. I told her that, while it might be hard for me to watch, it's growth and not something to run from. I made no secret it was my biggest fantasy to see her in this sexual way from this vantage point. She is also a very sexual woman but said that was all for me. Still, it made for good pillow talk. I had no idea my fantasy would finally come true during our Mexico vacation.

Getting to the exclusive Cabo resort, everything was as we remembered it. We had been to this place before and it never disappointed--great food and drinks, and top notch service. It was mostly a couples' resort; I suspect people don't usually want to drop that kind of cash just to have their kids screaming and running around. Once a while, we'd seen a single person there, but it was relatively rare. This time wasn't much difference except for one or two solo individuals who probably had their spouses at the spa or back in their rooms. I assumed Diana wouldn't give the presence of these single guys much attention, but I still conjured up a few scenarios about them and her in my head.

Our second day at the report started like most days there. We went down for breakfast, walked into the restaurant area, and were seated by a woman we'd seen there years before. Everything felt familiar and it relaxed us instantly. Most tables around us were occupied with couples, equally relaxed and engaged in conversation. About three tables over, I noticed a man, in his late 50s, with salt and pepper hair, sitting by himself. He was very distinguished looking, and I was sure Diana would've found him extremely attractive. I didn't think much about him at first except that his eyes were sometimes darting around the restaurant, as if he was waiting for somebody. I figured his wife would be along shortly but also wondered what Diana thought of him. Did she find him good looking? Did she have similar thoughts that perhaps he was alone? He was dressed casually, but something about how he was put together made me assume he was European. I figured that his partner would come along soon, but no one ever did. Diana and I engaged in our own conversation and made a plan to go change into our swimsuits to lay by the pool after breakfast.

Back in the room, I watched her undress and put on probably the skimpiest thong bathing suit I never seen her in, which really showed off her beautiful tight ass and tanned breasts which were nearly bursting out of the top. I could tell that her attitude was like "this is vacation. no one's going to judge us or care, and this is my trip to enjoy." Whatever she was actually thinking, it didn't matter. She looked great and I loved it. How revealing the suit was gave me a mixture of pride, knowing that, every day at the pool, she'd be getting excited looks from others. Why not? I look at her that way no matter what she's wearing. As she finished dressing, she hooked a little body chain to the suit, which reminded me of something else: the anklet I asked her to bring on the trip and wear poolside. We both knew the significance of the anklet and, since she likes playing into my fantasy (God bless her), she agreed to put it on as well. I got a twinge of excitement just knowing that certain guys would see it and hope it might be them we'd invite back to our room. We grabbed a couple of books and her pool bag and headed down to lay in the sun.

Once getting situated poolside, Diana asked if I wanted to take a dip in the water with her to cool off. Since I just got there, I decided to hang back and let her go alone. As she bent over to put her book back in her bag, she clearly gave some nearby guests a great view of her little ass, even a little view of the outer edge of her pussy lips. I noticed it too and it made my heart skip a beat. I situated a towel behind my head and watched as she walked to the pool and stepped into the water. As expected, at least three guys laying nearby pretended not to look at her, but I knew they must be watching. Why wouldn't they? I cracked open my book and began to read as I glance over at Diana from time to time, seeing her walking around the pool, occasionally smiling and making longer than average eye contact with other guests lounging nearby. Could she be flirting with them? Since the pool was still relatively empty, she easily found a spot at the far edge where she could put her arms up on the ledge and zone out while looking at the beautiful ocean beyond. As she leaned forward, arching her back and extending her ass slightly, I noticed the single gentleman from breakfast walking through the water, passing her more closely than necessary, and looking curiously at her and her body as he went by. I thought he might stop to talk to her, but he just proceeded to another spot about 10 feet away, pretending to also look at the view. Diana looked in his direction for a few moments, and then turned immediately in my direction, as if she knew what I was thinking. Although far away, she seemed to pick up on the fact that I was signaling my approval. The man saw her turn as well, but he kept his eyes on her until she turned in my direction and smiled. To this day, I wonder if he got his first clue from my smile of approval.

When Diana returned to our lounge chairs, our conversation started up again. I commented how beautiful she looked in her revealing bathing suit. She made a comment that I was being silly, but I explained I wasn't alone in my evaluation and maybe she should own that she was so sexy. When she asked what that meant, I pointed out how the solo guy from breakfast hadn't stopped at that particular spot in the huge pool just to "look at the ocean." I told her I know how guys operate and that sex is always on their mind. I explained the solo guy was just looking for a smile from her, which would greenlight some casual conversation in hopes of further engaging her. I said that's what all guys do when they're unsure of a woman's status or level of interest. Diana laughed that guys were "dogs." I said I knew that but that we were necessary dogs for the world to continue. She just laughed and went back to her book, but I knew all this got her thinking.

The rest of the day we spent alternating between laying by the pool, getting lunch and walking around the resort. We went to Concierge and talked about some dinner options but decided to stay at the resort and have dinner at the small outdoor bar near our room. Changing out of our bathing suits, Diana put on a very seductive silky black dress, still wearing the anklet. We walked the short distance to the bar, laughing and talking about experiences we'd had there before doing tequila shots and about how much we'd missed getting away these past couple of years. Although the resort had been busy for breakfast, no other guests were present at the bar. We ate, talked with the bartender about the various tequilas they offered, with Diana being very animated and excited about the upcoming days of this trip. As we laughed, the single gentleman from breakfast and the pool came into the bar area and took a seat not far from us, proceeding to order one of the more expensive tequilas they offered. We could hear his conversation with the bartender and, from what he ordered, we could tell this guy had some serious money. Although pretending she didn't, it was clear Diana recognized him from the pool. She was also clearly intrigued by what this guy must do for a living to throw down that kind of money on drinks. Judging by how closely Diana was observing his demeanor, I could tell she found him attractive and intriguing.

Sitting as we were with this very masculine older gentleman right across from us and the drinks flowing, I have to admit my mind stared racing. The man, whose name turned out be John, looked over at us several times, giving me a professional nod, seemingly open to conversation but not knowing if that would be too intrusive. Figuring he wanted to make a connection, I decided to be the one to start it. I asked which tequila he chose, and a conversation quickly proceeded. It turned out that he was not European at all but actually lived outside of Los Angeles. The conversation followed a predictable course, exchange pleasantries and surface information about our jobs and travel histories. It turned out John was indeed there alone, having recently separated from his wife and needing some time away from the stress of the divorce. Apparently, he had founded a successful financing company, but had since sold it and was taking his time to consider his next endeavor. Diana obviously found his calm attitude appealing, remarking that she was impressed he could live so freely while the rest of us stressed about our mortgages.

After a while of this, and feeling the booze kick in, we agreed it was hard to talk across a bar and so Diana asked if we should move to a table, suggesting John join us. He didn't miss a beat and, before I knew it, the three of us had been sitting together for another hour before I realized the drinking was making us bolder. Having my own share of bad relationships, we lamented about the difficulties John must be having going through his divorce. Mentioning what an attractive couple we made, John said how we were lucky to have found each other but was obviously focusing more on how attractive he found Diana. Given how Diana was sitting with her legs crossed at the edge of the table, John had a clear view of the anklet on her leg, more than once looking directly at it and then up at Diana--suggesting with his eyes that he knew what it meant. Diana noticed him look too and cast toward me a knowing smile.

When the conversation turned to the reason why he and his wife separated, John revealed she had cheated on him and, despite their efforts at counseling, he just couldn't stay with her anymore. Diana explained how where we lived was full of married people cheating. I agreed, but saying I didn't think the problem was necessary sex outside the marriage, but rather the lying. I said that some of these neighbors had an arrangement and were happy with it, but it had to be agreed upon first. Sensing that I was trying to move the conversation toward a spicier topic, Diana was looking a lot at me, wondering how far I would take this. I wrapped it up saying that it was enviable when a couple can get all its sexual needs met with honesty. Glancing at Diana, John explained that, so long as everyone gets pleasure from it, that kind of adventure might have even made his marriage stronger.

Thinking that part of the conversation had run its course, I excused myself to use the restroom, standing up and making a joke about, with all this talk about swinging, I hoped Diana and John would still be there when I got back. John laughed it off but Diana gave me a sly look as I walked away, sarcastically saying "you never know" and laughing as I grabbed my phone and walked off. Cleary, she knew what I was thinking, and was teasing me, but John was getting curious. In the bathroom, I took a few extra minutes to check emails, but was really just giving Diana and John time to talk alone.

When I returned to the table, their conversation was still on the topic of different kinds of relationships. As I sat down, I commented how they each seemed to really like this topic and how Diana even once thought I tried to set her up with another guy. I explained she was mistaken but that it certainly wouldn't have been the worst thing if it actually happened. John said the guy would've been damn lucky if it played out as he wanted, to which Diana responded playfully that, "well, he just wasn't the right guy." When John asked what kind of guy would be the right guy, I decided we'd had enough small talk. I half-jokingly said "well you, buddy" which left no question in Diana's mind about what I was trying to start. Despite her jaw dropping at this comment, she still mustered up a "yeah, right." It turned out to be the perfect response since we all then stayed silent for a moment, realizing we were all staying silent for a reason, looking at each other curiously. With her comment, Diana had clearly found her "partner in crime," a guy with whom she could maybe even make me a little jealous, something she knew I badly wanted. Clearly, a switch had gone on for her, where she was now apparently thinking "Fuck it. I know she wants this. Why shouldn't I do this?"

Sensing his opportunity, John got serious and said he respected our relationship but that, if this was ever something that we'd consider, he knew lots of guys who'd be happy to oblige. Diana just looked at him and coyly said "a lot of guys, huh?" then turning to me and saying "so, seriously, you'd really be ok with me being like one of our neighbors, doing it with some guy while you watched? You wouldn't be mad?" I asked how I could be mad at something that would remind me of how sexy she was, and how giving that would be to both me and another person. John just listened to us, praying it would end well for him. John commented that, since the bartender could probably hear us, if this was a conversation we wanted to have, we'd better have it in private. Diana just looked at me and said "let's go. I couldn't pay the bill fast enough.

As I opened our room door to let them pass, I saw John's hands low on Diana's hips, guiding her inside. As the door closed, she didn't turn around but just froze, staring at the room where it was all going to happen, waiting for him to lead her somewhere. It was so incredibly sexy how she just let him direct her, obviously waiting for him to make his move. As I stood and watched, he kissed her neck, his hands still on her hips, then moving them slightly toward the front of her dress just above her pussy, caressing her stomach and just above her mound. While his hands began to sensually explore her body, he pulled her closer, pushing his crotch against her ass, his right hand then reaching down to lift her dress, finally gaining access to her bare ass. As uncomfortable as I was just staring at this scene, I didn't dare disrupt what was happening. Her dress now lifted up to her waist, his hands were now on both of her cheeks, alternating between squeezing them and moving them apart. I thought he might end up fucking her right there until Diana spun around and engaged him in the slowest, most passionate kiss I think I'd ever seen. Remembering that I was there, Diana turned her head to me at one point and asked if I was really OK with this. All I could utter was an affirmative noise as she went back to kissing his face hard, her hands behind his head.

Diana knew exactly what she wanted and so walked John over to the bed, sitting down as John stayed standing. She quickly unbuckled his pants and then lowered them to the floor. As he stood there, she took his now hard cock in her hand and started massaging it but, surprisingly, didn't put her mouth onto it. I wondered what the reservation was. I guess John thought she needed a bit more coaxing to cross this line and so he reached down and started massaging her now soaked pussy. I was losing my mind with a mixture or jealousy and pride as Diana glanced over at me, her eyes squinting in pleasure and with the most determined look on her face. I knew what that look meant she was set on giving both me and John total satisfaction, albeit in very different ways. As he rubbed her, inserting a finger now and then, her head tilted back as she lifted her ass slightly to give him better access.

Almost ready to come herself, Diana took John's hand from her wet pussy and placed it on the back of her head as she lowered her face down onto John's hard cock, finally putting it into her mouth. John uttered an audible "oh fuck" as she pushed her face down onto his stiffness, grabbing his balls with one hand, stroking his cock with the other as she sucked sensually and slowly. As I moved to sit down on the bed near her, I gained a clear view of her mouth working his dick and balls. I could barely contain myself. "Oh my god, I'm so fucking proud of you," I said to her, prompting her to turn and look at me as she continued sucking, breaking her rhythm just a moment to smile and say "that's good."

Clearly, John was in total ecstasy as Diana continued her motion up and down on his cock, teasing its head, looking at me and holding that gaze as much as she could, John moving her hair from her face so I could see better. This was a show for me, I could tell, and they didn't disappoint. John turned to sit on the bed as Diana then got on her knees in front of him. His body arched backward, giving me the most amazing view of my wife's mouth, the same mouth that I kissed every day, moving sensually over the skin of his engorged penis, her tongue slightly darting around as she approached the head of his cock on each stroke. As John's body writhed almost uncontrollably on the bed, it was clear that Diana wasn't going to stop until he was completely spent. Wanting to make it last, John tried to slow her movements down from time to time with his hand still behind her head, but she was having none of it. She wanted to taste his cum and have me see it. As she worked her other hand against his balls, holding them firmly, and I knew John wouldn't last much longer.

As he was clearly close to cumming, I whispered "however you want this to end is fine." She took her head off just for a moment to say she wanted to taste it, that she really wanted me to see this, that she was going to do this. I almost orgasmed right there. As she continued sucking, she was making little whimpering sounds, almost like a wounded animal, pretending she had no control over the flood this guy was about to give her. As John loudly announced "Oh shit. I'm close" and then winced, Diana made a moaning sound I'd never heard before as John's body tensed up, his cock convulsing, unloaded his cum forcefully into her warm mouth as he held the sides of her face and grunted.

Diana squeezed his cock tightly and slowed almost to a halt as it pulsed aggressively and she slowly moved her hand up and down, milking it all. Diana always swallows my cum when she sucks me, but I sensed she was holding back something this time, and she was. When John stopped bucking, Diana opened her mouth cautiously to show me the sticky cum she was holding there, and I suddenly felt the most amazing pride ever, pride in that she'd completely embraced her sexuality. John left his hand on her shoulder as he witnessed his load on her tongue. She cupped one hand and let his cum drip from her mouth, using her other hand to continue sensually massaging the area just under his balls. Seeing John's cum still sticking to her tongue despite her efforts to spit it out was so hot, like he'd left part of him inside her that would remain inside her. Surprisingly, she didn't get up, but just sat there with a huge grin, staring at me and John's still hard cock, commenting on how his cum was a lot to take but didn't taste bad at all, and how she had almost convinced herself to let him fuck her. Although John mentioned how wet her pussy had been earlier and how he'd gladly have done that, I still knew Diana made the right choice. She was sitting there on her knees, with cum in her mouth, on her lips and in her hand, and she did it all to show me I'd chosen well.