This got really long, so I had to split it in two. Part two will have more “going wild”, but it was hard to get to that point without the background.
As I mentioned in the [last episode of my Cabo story](https://www.reddit.com/r/gonewildstories/comments/rwvxuo/a_continuation_of_my_beach_bar_hookup_in_cabo_fm/), after leaving McKenna at the harbor, I headed back to my hotel. It was a nice morning, so I decided to walk back and take in all that downtown Cabo had to offer. When I got back, the others in my room were still asleep, so I went to the gym to get a workout in. There were a couple others working out as well, including a good-looking brunette probably 10 years younger than me. We made some small talk, but I was not getting the vibes that would lead me to try pursuing something, so headed back to my room and showered.
When I got out of the shower, I had a few text messages and a snap notification on my phone. The snap was from McKenna, with a pic of my hotel, taken from the bay on the boat, with a caption about it being a fun night. Then a pic with her friends that said ‘Cabo Vibes’. I checked her stories and that one was there as well. I scrolled through a few other snap messages, including some from some other women I message with regularly, before switching over to the ‘Gram and checking in there, seeing the same Cabo Vibes post on McKenna’s IG. I didn’t want to come across too thirsty, so didn’t send anything back, and decided to get a suit on and head to the main pool to join my friends.
I was pleasantly surprised when I got down to the pool, as there was a good mix of people there already and the scene had good energy. I settled in with my group and took in the crowd to see if there was anyone worth pursuing, or at least chatting up. There were lots of couples there, and but a handful of groups, two of which appeared to be groups of females that I would keep an eye on as the day went on. I also saw a couple single women around the pool, which could also be promising.
I hung with my group for a while before deciding to cool off in the pool. I was joined by another guy from my group, and he and I made our way around the pool and talked to several of the others at the pool. For the most part, some nice casual conversation (a few didn’t appear to enjoy the interruption from what they were otherwise doing), but no real bites in a way I would take seriously.
We headed back to our group, and I saw an Asian woman in her late 20s or early 30s sitting a couple chairs down, so sat on the end of our group’s chairs, a chair away from her. She was preoccupied with her phone, but there was an air of frustration in the way she was using it.
Not wanting to interrupt whatever had her attention, I bided my time and read some texts and emails on my own phone. No texts or snaps from McKenna, so I switched over to IG to see if there was anything new there. Her account was radio silent, but there were a couple new pics posted with her tagged in them of her and two other girls, laying out on the bow of the boat. The first was face down, all three girls topless. The second, similar, but they were face up. McKenna in the center, with a ‘Suns Out Guns Out’ sticker digitally applied over her chest, the other two with hand bras. I made a mental note to keep an eye on that friend’s IG account.
As I cleared off some final morning emails, I turned my attention to the Asian next to me. After a few minutes of exasperated sighs, she made a call and I overheard her trying to make a reservation for dinner, which ended unsuccessfully for her.
‘No luck on the reservation?’ I asked, making obvious my eavesdropping.
‘Oh my god, don’t get me started!’ she replied, and then proceeded to unload to me on her frustrations. She and her husband got in on Saturday (this was Monday afternoon, for those keeping score at home), for an anniversary trip that he had ‘planned’ for them. Not realizing the current situation in Cabo, he had thought they could get dinner reservations while down here, much to her dismay. To further her frustrations, he went golfing Sunday and was deep sea fishing today, so it has been up to her to figure out where they could eat.
I listened to her rant and told her my group had dinner plans at a great restaurant maybe 45 minutes away in the hills. I grabbed my phone, and called to the restaurant, explaining that we had two of our group that were celebrating and didn’t want to be at the group table, and wanted to see if we could get something private. My new friend looked at me like I was crazy, even more so when it worked.
We continued talking about other restaurants in town, and I gave some suggestions on places that would be more likely to accept a walk-in couple. Robin shared more of how disappointing the trip was. Her husband Matt had grand plans for the trip, but everything has fallen a little short. He told her they had a private pool with the room, which he based on photos on the website, not realizing that not all the rooms have that. It wasn’t until they got to their room that she realized they didn’t. As a result, only one of the swimsuits she brought was something she felt comfortable being fully in public in, the fairly modest one she was wearing. She clarified, nothing too risqué, just not something she felt appropriate to wear at a hotel pool.
I asked her how long they had been together – met in college, married a couple years after, celebrating 7-year wedding anniversary, and 10 years together. Fairly momentous, making the disappointing parts of the trip sting all that much more. After thanking me again for the help on tonight’s dinner, she went back to her restaurant searches and answering some work emails, and I headed back to the pool with my buddy where over the course of the rest of the afternoon he and I hit on a couple singles to no avail.
Late afternoon, headed back to the room for a quick catnap and then showered. I grabbed my phone and responded to a few texts, which included a few from girls I had met the prior week and was working on. Another cursory review of IG, still nothing posted *by* McKenna, but some new material in which she was tagged, specifically a pic of her and another girl, backs to the camera and apparently still topless, given the lack of straps on top, in what appeared to be a twerking position, McKenna’s thong barely visible between her perfectly sculpted ass cheeks.
I checked the profile of the girl who posted the photo, and saw she had new videos in her stories so checked those out as well. The first was a video of the girls dancing on the boat, drinks in hand. The second was captioned about her roommates being wasted, featuring a video of McKenna and the other girl on their knees, acting as the luges in a dual butt luge, with White Claws being poured down their cracks into the waiting mouths of a couple of the guys on the boat, and given the proximity of those mouths to the asses, it didn’t seem like much of the White Claw was spilling.
I finished getting ready and our group met down by the lobby and piled into several Suburbans for the trip to Los Cabos for dinner. We did some shopping and grabbed cocktails before dinner, enjoying the cooling air of the evening after a comparatively hot day. While we were getting started on our orders, I saw Robin and Matt walk in to be sat. Matt appeared to be punching well above his weight class, but had a good-looking face, so thought that maybe he’s let himself go in the past seven years. I did note that he seemed a little, perhaps more than a little, drunk when they were being sat.
As I had anticipated, the food was absolutely spectacular. Fresh, seasonal, and well worth the drive and the cost. The Company was great as well. Our entire group managed to make it out, and there were a lot of speeches and congratulations shared across the table. A lot of laughter as well, including some directed at me in good fun. When the entrees came, the porterhouse pork chop that was delivered to me elicited the following exchange:
‘Oh my god Jack, that’s so thick!’, said the wife of my great friend who had invited me.
‘That’s what she said!’ someone down the table chimed in.
‘You joke, but I literally have heard at least two different women say that while sharing a wall with this asshole’ said John, who was the other single in the villa I was staying in this week.
‘Speaking of, where is your darling little college student Jack?’, my friend’s wife asked.
‘Doing what college students should be doing in Mexico, getting wasted, half naked on a boat somewhere.’ I replied, to laughter from the table.
So yes, some laughter at my expense, but I suppose the best kind. The entrees were great, dessert even better. I glanced over to Robin and Matt’s table a few times during the night and observed their body language. He was just generally blitzed while she seemed annoyed. I hoped for her sake that their actual meal was as good as what my table was all having.
We settled up the bill, and by that, I mean our rich benefactor picked the entire thing up, after which we piled into our entourage of Suburbans for the drive back to CSL. When we got in, about a third of our group retired to their rooms, a third decided to hang out at the hotel’s poolside bar, and then a third of us went to a rooftop bar nearby, with me joining the rooftop group, figuring that that was the best chance for some more fun.
My expectations were correct, and the bar we found ourselves at had a favorable mix of women to men, many of whom appeared to be single. After a bit, a couple of us ended up talking to a bachelorette party, and after buying the group some rounds of drinks, we ended up co-mingling with them further.
Things were looking up on my evening, especially when one of the hotter members of the party, Kim, ended up sitting on my knee to thank me for buying them drinks. She was a bridesmaid, with the bride being one of her best friends from high school. Late twenties, brunette, and fit, and I decided to see how far I could take things.
As the club got more crowded, things got louder, and she moved closer to talk, never leaving my knee and thigh. I had my hand on the small of her back, lightly rubbing circles on her, and she was responding favorably. She was absentmindedly tracing her fingers up and down my leg, in between talking and taking sips of her drink.
We made eye contact and she subtly licked her lips. I took a chance in that moment and leaned forward. Judging the nonverbal cues correctly, Kim leaned in as well, and what started as a brief kiss turned into full on making out on the couch in front of our respective friends. Kim moved off my knee by turning into me and straddling me, the thin fabric of her knee-length sundress doing nothing to obscure the warmth between her legs from transferring through her underwear and my shorts as she grinded on me.
We made out like that for probably 15 minutes, as I heard her friends commenting, ‘Get it Kim!’ and the like. When we broke the kiss, she looked around sheepishly, before resuming our make out session. Since she resumed things, I took the opportunity to bring one hand up the inside of her thigh, until it reached the smooth skin of the crease between her leg and torso. I felt the warmth and dampness of what felt like a lace thong and rubbed her clit over the fabric while her tongue probed my mouth.
When she next broke the kiss, I asked if she wanted to get out of there and head to my room. To my surprise and amusement, she flat out turned me down saying, ‘Nope, I have a boyfriend back home, and I’m definitely not going home with a fuckboi’, before returning to the kiss, and pushing even more firmly against the fingers circling her clit.
I could feel her get wetter and moved my thumb to her clit while my index finger moved down to stroke between her lips, pushing the fabric up and in between the soaked lips of her pussy. Her kissing became more urgent, and her hips began to subtly buck against my hand for a half a minute or so. When she broke the kiss the next time, she hopped up off my lap and said, ‘thanks again for the drinks’ before finding the bride and dancing.
I took that as my cue to call it a night. I found my two friends at the bar, and after they settled up, we headed back across the street to our resort. While there was *some* touching with Kim, I wouldn’t have considered here part of my streak, so luckily for me, McKenna and I had fucked earlier in the day. Given the long day in the sun, the great meal, and some light drinking, I slept well that night.
This is a continuation of the [poolside connections story](https://www.reddit.com/r/gonewildstories/comments/w2tjvp/making_connections_poolside_in_cabo_mf/?) posted earlier. Hated to split it up, but character limits are what they are.
When I woke up, I threw on some workout shorts and a shirt and headed down to the gym and spa area. I had seen there was a morning yoga class and thought I would check it out. The sun was just rising, and there were only a handful of guests and staff milling about. When I got to the room near the spa, there was a sign on the door saying the yoga class would take place out by the pool as a covid prevention measure. Since the weather was fantastic, it would be a great setting to take in a light workout.
The other participants gathered, and the female instructor was now standing in front of a small group of eight of us, six women, myself, and another guy who looked to be in his 60s. The women looked to mostly be in their 20s, with one probably a touch older than me, and another in her 50s who appeared to come with the other guy. We did a relatively light workout, and at the end of it I was energized and not tired in the least so decided to head to the gym facility to get more of a workout in.
When I got there, it was all but empty, with a woman just leaving. Right after I arrived though, one of the women from the yoga class (one of the ones in her 20s, and an attractive one at that), came through the doors. We gave each other a friendly nod of acknowledgement as she went over to one of the treadmills while I went to the rowing machine. I would have normally gotten a cardio workout in on the treadmill myself, but since I was freeballing under the workout shorts, I thought better of it.
I watched her get started as I started my own workout. She was quickly up to a good pace, clearly not a casual runner as the tone of her ass in her yoga pants confirmed. And what a pair of yoga pants they were, light green in color, very thin material, and with the seam splitting and emphasizing the cleft of her ass.
The temperature in the gym was warmer than I would have expected, and within short order I was sweating, and I could assume she was in the same boat given her pace. Both of us wearing masks wasn’t helping the situation. She paused her workout, turning to me and saying, ‘would you mind if I took this off?’. Not being particularly worried given the distance between us, I said ‘sure, not a problem’, and was slightly surprised when rather than just taking off the mask, she took off the tank top she was wearing, now just wearing a small sports bra. I *definitely* didn’t mind that she took off the shirt!
She resumed her run, and I did another couple minutes on the rowing machine before moving over to do some cable twists. That had the added benefit of shifting my perspective from just the excellent view of her ass to getting a good view of her breasts bobbing in the sports bra as she ran. I periodically checked her out while continuing my workout, as she finished up and went into her cooldown.
When she finished, she walked directly over to me, her cleavage glistening with beads of sweat rolling down between her breasts. From what I could tell, she was probably a full C, which looked great on her athletic frame. She had a great smile too, so I’m glad she took off the mask. ‘Could you help me with that machine, I haven’t used this type before?’ gesturing at the power rack.
‘Happy to, I can spot you if you want as well.’
‘Oh, thank you, that would be great!’
‘I’m Jack, by the way.’
‘Rachel’
We walked over to the rack, ‘So, did you want to bench, or what were you thinking?’
‘I wanted to do some squats.’ Oh boy, I thought, this could get interesting. ‘The gym I go to has rails on the machine, so it’s a little different, thanks for helping.’ We talked through how much weight she wanted to do, and I got her set up. Before she started, I wanted to make sure Rachel was comfortable with the spotting, since a spot while squatting can get *pretty* familiar. She appreciated the question, and confirmed she was okay.
When Rachel got started, I made a couple suggestions on her form, since there was more movement when doing the squat without the rail assist, but overall, she did great. More importantly, standing immediately behind her for the squat gave me a fantastic vantage point to watch her ass. After the first few, it became very apparent that under the yoga pants was not a stitch of clothing, and I watched as the already thing fabric strained in the squat. The sweat from the earlier cardio workout also came through, making a v shape at the top of her crack.
Watching her ass as she finished her sets, I realized I had sort of chubbed up a little, and was the slightest bit self-conscious about it, especially given my own attire. Looking down, it was entirely noticeable. I helped Rachel get the barbell back on the rack and complimented her form. ‘Thank you, if I wanted to do some bench presses, could you help me with that too?’ Of course I was happy to. We got that barbell set with her weight, and after she was in place, I helped her get started.
I realized as she was in position for her bench press that the squats had pulled the yoga pants directly up into the cleft of her vulva, giving her quite the cameltoe. In fact, with the thinness of the fabric, you could pretty much see everything. The “v” of sweat on her back was mirrored in the front as well, although slightly wider. Between the visible cameltoe and the glistening breasts in her undersized sports bra, I could feel the ¾ chub extend a bit further. Not quite rock hard, but I was at almost full mast, extending down the left leg of my shorts, straining against the fabric and pushing out with the tension of the need to rise up. A little awkward when standing less than a foot behind her head and right above her eye level.
When she finished her first set, I helped her put the bar back on the rack. Not trying to be one of those creeps who straddles the person’s head, I stayed back as much as I could, but was still perhaps 3 inches away from her. I saw Rachel’s eyes make contact with the distinctive shape protruding from the left leg of my workout shorts. The fabric of the shorts was doing nothing to hide anatomy, and between color and the thickness (or lack thereof) of the fabric, at least from my perspective, I felt like you could make out the head if not individual veins in the shaft. The moment of realization was apparent on Rachel’s face, her lips parting and eyes widening just slightly. She didn’t say a word though. We made small talk about her set, and she started the next one. I approach again, and I saw her eyes dart to my leg once again before returning to the bar.
This process repeated at the end of her second set and then at the start and end of her third, at which point she said she was done and got up. She wiped down the bench while I was adding weight to the bar for my own workout. Rachel asked, ‘Did you want me to spot you too?’ I had honestly planned to do my bench without a spot, but welcomed the opportunity to spend a little more time with Rachel.
When I got down to the bench, I realized the “dick print” was even more pronounced in that position, straining against the fabric. Looking up, I saw Rachel’s eyes locked onto it as well. I moved my hand down to slightly pull the shorts, hoping to relieve enough pressure, and do it subtly, with which there was no success. Rachel said, ‘Feel free to adjust there, not a problem.’ I lifted the waist band just enough to cause my cock to spring back against my body. Looking down, I was able to see it directly, and while I wasn’t positive Rachel did, it wouldn’t have surprised me at all if she had. Luckily, the lack of strain helped relieve some of the erection.
I went to grab the bar, and Rachel moved forward. Given the additional weight, she moved perhaps closer than I had, and was now just behind my head. As I looked up, I was treated to a close-up view of the cameltoe I was seeing before, along with the slightest bit of underboob, given how small her Alo sports bra was. If the lack of pressure had relieved some of the intensity of the erection, that brought it right back. Luckily, once I started lifting, it subsided again, although I stayed at probably ¾ firmness throughout.
Once I finished my sets and wiped down the bench, Rachel and I walked over to get water. I asked about her plans for the day, which consisted of shopping. ‘If you want to come by the pool bar later, I’d love to buy you a drink, and if you’re up for it, perhaps dinner?’
‘I don’t think my husband would like that!’ she replied.
Without missing a beat, I said, ‘Where’s your husband now?’ taking a chance that she was, like several women I had seen this week, on a girls trip.
‘Upstairs, probably still asleep.’
‘Well, the offer is still open. Hell, bring him along.’
Rachel laughed, ‘That’s tempting, but I get the feeling that what you are looking for isn’t quite our speed. I’m sure you’ll make someone else’s night if you are successful though. Quite an eyeful this morning.’
We thanked each other for the workout assist, and said we’d see each other around. With that, we walked out of the gym and headed back to our respective villas. I was soaked with sweat at this point and jumped in the shower to clean off. When I was done, after texting some of my friends, saw they had just headed to breakfast. I threw on a pair of board shorts and a clean t-shirt and headed down to meet them.
Source: reddit.com/r/gonewildstories/comments/w2tra9/making_connections_poolside_in_cabo_fm