As I mentioned in my last post, it was our final full day in Cabo. We were there celebrating as a group, celebrating a huge return on an investment we had made in a real estate venture. With such a varied group, throughout the week people had split off and done various things separately. The group had decided that for our last day, we’d hire a few cars to take everyone up to see the “Hotel California” in Todos Santos, an artist colony about an hour north of Cabo, and then that evening do a dinner together and a bar crawl downtown.
I had originally been indifferent to joining them in Todos Santos and figured I would rather hang out by the pool and look for a hookup as opposed to spending a couple hours in a car and sightseeing, but after starting my morning pounding a 19-year-old college student before she almost threw up in my bed, I decided playing the adult and spending time with my friends was the wiser choice. Besides, now that I had continued my “streak” another day, there was no compelling reason to be on the hunt all day, as there was no groundwork to be laid (so to speak, pun entirely not intended) for future hookups since it was our last day in town.
When I got back to my room that morning, I stripped the bed (for the third time that week, incidentally), and then took a shower before meeting our group for a pre-drive breakfast. As we were assembling for the SUVs to drive us up, my friend John showed up, apparently straight from the room of the girl he had slept with the night before, as he was still in the same clothes as yesterday.
We got started on the drive, with John and I sharing a row in our SUV. We exchanged details on our respective nights, and he shared that when they got back from the pharmacy to Kelsey’s room, she had calmed down from the panic, and the lust that had consumed them before took over again, leading to a couple more rounds. Since they’d already crossed the Rubicon on bareback/full fluid exchange sex, they continued on like that for the later rounds as well.
I asked him what happened the night before, and he said even though they didn’t have any condoms, she was okay with going bare as long as he pulled out. That was the plan all along, but during sex, she kept saying “keep going, don’t stop”, and when he asked if she was on the pill, mentioned her parents hadn’t let her, and after having just turned 18, she hadn’t yet done it on her own. Her saying she just turned 18 pushed him over the edge, which is when disaster struck. Apparently, it wasn’t all that bad though, since they continued on into the morning, and exchanged numbers as well.
Around mid-day, there was a slight lull in our sightseeing as we all gathered for lunch. I pulled out my phone and had a couple messages, including one confirming plans for a dinner date tomorrow. I decided to check my socials and saw that Cameryn, one of the girls I had met earlier in the week, had connected with me. She was part of the group that we had met on our second day in town, one of whom (McKenna) I had hooked with up a couple times. She’d had some interesting IG posts that I thought would make a good follow, and she apparently wanted to connect on Snap as well.
Cameryn had a couple stories posted, so I decided to see whether her Snaps were as interesting as the IG posts (thinking, “Of course they’ll be interesting, probably more so…”). The first post I saw was a short video of her and friends out at a club, looking like the hot college-age girls they were. The next post in her story was a boomerang of five of them, again at a club, with the caption “Partying with our friend Molly.” In it, McKenna, my hookup earlier in the week was rubbing on, and making out with one of the other girls, Cassidy. The next post, though, took the cake. Captioned “When your roommate takes a double dose – comes home from the club at 9am and passes out on the bed”, it showed a girl face down, naked on the bed, one leg bent, with a three water drops emoji and WAP covering up the naughty bits. From what I could tell, I was 99% confident that was McKenna. As I had realized a couple days before, she was just living her best college girl life down here.
Since it was our last day, I thought I might just see if there was any chance of one more hookup and sent McKenna a quick text of <Hey you – Leaving tomorrow, any plans tonight?>. We hadn’t had any contact since she I dropped her off at the pier for her boat trip, so this was a long shot, but you miss 100% of the shots you don’t take, so why not try.
After lunch, we looked around the town some more and did some shopping. Overall, our sightseeing trip was great (I highly recommend Todos Santos if you are heading to southern Baja), and by late afternoon, we were headed back. Everyone went back to their rooms to freshen up for our final group dinner at the Sunset Monalisa. After another great dinner with spectacular views, we headed back towards the marina for a final celebration of a bar crawl. Nothing too out of control, as the jet was slated to leave the next morning around 10.
I still hadn’t heard anything back on my text from earlier in the day. Checking Snap again, I saw Cameryn had a couple new Snaps posted. “Post-brunch welfare check before pool time” featuring a still naked roommate, bits all covered with emojis, still passed out in bed. “Sleeping beauty finally wakes up as we are walking out the door to dinner… Dry shampoo and a line – hot girl tips!” This one featured McKenna for sure, now dressed, doing a line of what appeared to be coke off a coffee table book. The joys of being 21.
Our group, meanwhile, were still having a fairly low-key evening, and I in particular was trying to be good in light of my behavior earlier in the week, which a couple of the women in my group had picked up on given I wasn’t engaging with any of the single women at either of the first two bars we went to. But try as I might to be good, old habits die hard, and when a group of attractive women walked into the third bar of the night, I couldn’t help myself.
The group of four women looked roughly my age, perhaps up to their early 40s, and were uniformly attractive. They ended up taking a table right by our group. I did notice, however, that all four had wedding rings/sets, and not insubstantial ones at that. Not necessarily deterred, I observed the group for a bit to figure out whether there was a play to be made. It was apparent from chatter and their interactions that this was an after-dinner stop off for them, and that there had been drinks with dinner, if not additional drinks earlier in the day as well.
Soon after sitting down, their waitress arrived with a round of large margaritas, and the four began to drink them while people watching. One of the four, however, had moved from her barstool to stand next to the table and looked to be trying to get her friends to come dance with her to the old school hip hop the DJ was playing. She was conservatively dressed in white jeans and modest tank top, but I also spotted a tattoo down her spine, which to me signaled she wasn’t *all* that innocent. Perhaps it was the white jeans, but her ass (which was a great ass, by the way, perfect bubble butt) was just slightly too large for her frame.
‘I can’t get my friends to dance with me either’ I said across our table to theirs. My statement caught her attention and she turned to me with a smile (masks were not required at this bar, which was for all intents and purposes indoor/outdoor).
‘I just want to daaance!’ she shouted back.
‘Do a shot with me then we dance?’ I suggested. She eagerly nodded, and I came around to her table and we walked to the bar. She ordered tequila shots and we toasted and downed them. I introduced myself, ‘I’m Jack’, and she replied, ‘Jill!’
‘It was meant to be!’ I replied.
We headed to the open area where some others were dancing and began to dance with one another. It started off innocently enough, but after a couple songs, I would say the dancing got a little flirty. Jill rubbed up against me a little, and then I did the same. It was like a game of cat and mouse, only we kept alternating roles in that game, one being the aggressor before switching. Flo-Rida’s “Low” came on, and Jill really hit her stride. She had every move to that song down, and as I watched her dance in front of me and on me, the thought of bending this MILF over and pounding that ass from behind got me pretty hard.
Jill put her ass right on me, bending forward, and grinded herself up and down directly on my now hard cock before pulling away slightly and putting a hand back behind her. Her hand went directly to my pants over my cock and I saw the exact moment of recognition as she popped up quickly from her bent over position with wide eyes. ‘Ummm, let’s get another drink.’ she said. We went back to her table, and she grabbed her margarita, downing about half of it quickly. I grabbed my Pacifico from my table, rejoined her and took a sip.
My group started to leave, with a few peeling off to go home, while others were headed to the next bar. ‘So, my group is heading out. We can stay here and dance more, or skip that and we can get out of here together?’ Jill paused for a second, giving me hope, but alas, she raised her hand to point to the quite large ring before saying, ‘Sorry! Good luck with that though!’ and patting my cock lightly through my pants.
I took the L and headed out. I had a text that our group had headed down to another bar down the way. Catching up to them, we paid our cover and almost immediately, the shit talking commenced about my failed attempt to land the MILF. ‘Nice to know you strike out sometimes’ one of the guys said to me. Another said he just won $10 from another of our friends, on a bet as to whether I’d get her to leave with me. ‘Happy to see you fail there, Jack.’
This bar was comparatively dead, but we decided to stay to grab a drink since we had paid a cover and got an included drink. The waitress brought Coronas all around, not ideal, but given the scene, not too surprising. We people watched for probably half an hour, with some of our group getting a second round. Around 11:30, though, the atmosphere started to change a bit. I don’t know if another bar shut down for the night or what, but it was like a transformation occurred, with a line forming to get in, and the music getting louder, and changing style a little which seemed to bring in a younger crowd.
About five minutes after that change, a group of a six younger women walking in caught my eye. Again, uniformly attractive, but in this instance, dressed more like they were out for a night in Vegas, in contrast to the more casual/beachy attire most were wearing that night. As they walked in, they were immediately led to one of the private tables by a bouncer. Within minutes, bottle service arrived, and the girls were imbibing.
As I watched the group, I realized that one, who had her back to me or was otherwise obscured from view was Megan, whom I had run into the day before at The Office and had connected with in April on Seeking. That April connection only resulted in a single meet-and-greet date, but it was clear the sugar she had been looking for was well beyond what I was interested in investing. Our conversation the day before had been somewhat brief, but pleasant.
Megan had gotten up and after slamming back what looked to be vodka and soda, was gathering some of her girls to join her to dance. She had looked great the day before at the office in a bikini, but somehow wearing more tonight, she looked even better. She was wearing a red bodycon dress, it showed off every part of her body amazingly well. Overall, she just looked incredibly put together. It was a little evident though when they got to the dance floor that the drinks they just were served were not their first of the night (or likely even the second, third, or fourth).
I decided I’d try my luck with Megan again (although my try the day before had been just a fleeting interaction). I went out to the dance floor and made my way towards Megan. It wasn’t easy to get in her orbit, with the crowd on the dancefloor, other guys vying for her group’s attention, and the other girls she was dancing with. But when I did finally get close enough, I caught her attention with ‘Looking hot again Megan.’
‘Hi Jack! I keep running into you down here. Swear I’m not following you.’
‘Sure you’re not. Having a fun night?’
‘Yes! We leave early Saturday, so last chance to go out like this.’
‘Is your, uh, boyfriend, or whatever here?’
‘Oh my god, no! This is totally not his thing. He’s prolly asleep.’
‘He’s missing out, you look fantastic.’
‘Thank you’ she said in a somewhat flirty way, pouting her lips after. It actually gave me the thought that this actually materialize into something here. ‘Let me get my drink, do you need one?’
‘Sure’ she took my hand and led me up to their table where two of her group were already sitting. ‘This is Jack. He and I know each other from home. Jack this is Alex and Natalie.’
‘Nice to meet you ladies.’
Megan made a vodka soda for me while the two joined their friends on the dance floor.
Megan and I talked for probably 15 minutes there. Given how loud it was, it necessitated us sitting quite close to one another and leaning in. She smelled intoxicating, and the longer I spent with her, the more I was actively wanting to close on this pursuit. I won’t bore you with a bunch of dialog that I would be paraphrasing anyway, so will get to the gist. ‘So, you and this guy, exclusive then?’ I asked.
‘Sort of? It’s complicated’ she replied.
‘Complicated how?’ I followed with.
‘His wife?’ she replied laughing.
‘Ohh, yeah, that’s a complication. What about you? Do you have anyone on the side?’
‘Nope, no sidepiece for me.’
‘Want one?’ I asked, with all the innuendo dripping.
‘It’s tempting.’ She said, giving me a look before continuing on. ‘He said he needs this because his wife isn’t keeping up with his appetite, but then this week I’ve been lucky to get 10 minutes every other day. Whatever, it’s vacation, and I got to bring my friends.’ She said before she took down what was left of her drink.
‘My place is not far away if you want to take out some of that pent up aggression. I’m positive I’ve got more than ten minutes in me.’ I could see the inner turmoil in Megan’s eyes. ‘Let’s go dance again, and you can think about it.’
We went back to the dance floor and got back at it. Megan alternated between dancing with me directly and dancing with her girls. She would dance with a manic energy before pausing to look to see who was watching, in a way that I thought underscored this conflict within her. She had just graduated and wanted to party, but at the same time, was trying to mirror the elite status that her benefactor had bestowed on her.
After about 30 minutes of dancing, alternately between me and the girls, Megan had made her way back to me. She had worked her way close, and with her 5’8” frame and several inch black heels, we were face-to-face. I thought for sure she was going to kiss me the way she was looking at me when she leaned in. She swerved at the last minute though, and her lips when towards my ear.
‘Was thinking about your offer. Tempting, but I’m gonna pass. Too much to lose, you know? Besides, you had your chance.’ Ouch, that last part stung. It was true, I did have the chance, but still hated to hear it.
‘All good. If you change your mind when you get back home, you know how to find me.’
She gave me a quick peck on the cheek and went back to her girls. I realized I had been away from my group for almost an hour at this point. I made my way back up to them, seeing the group had now dwindled to just five other guys and two women. It was now a little past 12:45 and they were antsy to leave. ‘Are we leaving for home, or another stop on our bar crawl?’ I asked.
‘We’re out, heading home,’ one of the couples said. They were joined by one of the single guys. The other couple and the two other single guys wanted to hit up another bar, so off we went. As we walked by El Squid Roe, the vibe inside seemed pretty lively still, so we go in line, paid another cover, and headed in. It was actually surprising full in the bar, especially given it was almost 1am. We got in, got another “complimentary” round of Coronas to sip on, and tried to find a good spot to people watch.
The people watching was again good, with a lot of people making very questionable decisions. It was nice to see some normalcy return to this vacation destination after over a year of panic and a pause on life. My group was finishing up our first round, and ready to get a second when I saw a hot girl walk up to the bar. Now, I say I saw a hot girl, but in reality, I didn’t really have any validation on that, as her back was to me, so I was only going off of her figure, the way she carried herself, and her attire. Still, to me, it read “hot.”
I volunteered to get us the next round, and went up to the bar, next to the girl, who had just ordered a round of frozen drinks in plastic cups. The seven or so cups looked to be way too much for her to carry, giving me an opening. ‘Need a hand bringing those back?’ When she turned, I had a moment of recognition, but couldn’t quite place why I recognized her.
‘Oh my god, you’re McKenna’s D…’ she said, before pausing, so I don’t know what the D word was going to be. With context, I realized it was Cassidy, one of McKenna’s best friends who I had met several days before and who was featured prominently in the socials I had seen over the past couple days. ‘Stay right here.’
She took off with two of the frozen drinks, and I followed with my eyes as she navigated a walkway, heading up a short flight of stairs to a seating area sort of above where my group was sitting, previously not in my line of sight. A group of girls and a couple guys were dancing in front of a table, and I watched as Cassidy got caught up with a couple of them trying to dance with her.
Cassidy beelined though into the booth and tried to get the attention of a girl who was dancing on the table with a guy. Given the angle, it was hard to see who the girl was, but I suspected it was McKenna given the situation. Also, I said they were dancing, but really, there was some light side to side movement while they were actually making out. Also, I couldn’t totally tell where his hand was, but when Cassidy did get the girl’s attention, the first thing she did was re-arrange the extremely short denim skirt she was wearing. When she bent down slightly to talk to Cassidy, my initial suspicion was confirmed, there was McKenna, in the flesh.
After a super quick conversation, with Cassidy pointing down to where I was, McKenna climbed down from the table, and ran down the stairs, straight at me. ‘Oh my god, Jack, I didn’t think I would see you again!’ she said, rapidly. She was in a super short cutoff and frayed denim skirt, a black tank top (with no bra in sight, and nipples poking through the fabric), and flip flops, with her hair in pigtails. It had only been a couple days, but I had sort of forgotten just how absolutely beautiful and sexy she was.
‘Hey McKenna, didn’t mean to interrupt your night. Having a good time?’ Before I could even finish that statement, she had wrapped her arms around me leaning into me. She leaned her head back and pulled mine down to kiss me. Her mouth was wet and tasted of the fruity cocktail they had been drinking, and a little salty as well. I tried to put it out of my mind that she had just been making out with another guy.
‘Having a better time now!’ she said again rapidly. She then proceeded to tell me all about the past three days since we had parted ways. She was talking so fast I could barely follow everything she said, but apparently her phone had gone overboard on the boat trip she had gone on Monday, hence no texts or snaps from her since. Lots of partying, apparently. ‘I tried to come see you last night! We did molly and I was so horny. I found your resort, but couldn’t figure out what room you were in, and it was like 2am so I didn’t want to bang on the wrong door, so ended up going to an after hours club with friends and did more molly and, yeah. I wanna dance, do you wanna dance? Let’s go dance.’ She was literally racing through her sentences, it was cute, but at the same time, sort of exhausting.
‘Let me get drinks for my friends first?’ I suggested.
‘Ooh, your friends are here? Can I say hi, where are they sitting? I’m so happy Cassidy found you! I really wanted to see you again before we left Cavo, did I tell you I tried to come see you last night? Seriously, so horny. I needed you last night. I wish I hadn’t lost my phone. I would have booty called you. Where are you friends sitting?’ I had the thought of 21-year-old McKenna coming to my place last night when I had the 19-year-old Peyton naked in my bed. That could have been incredibly awkward, or incredibly great.
I pointed the way for McKenna to my friends and she grabbed the last of the frozen drinks that Cassidy had left at the bar and walked over to them. I ordered another round of beers, switching to Dos Equis, and joined them at the table. My group was wide-eyed at McKenna’s rapid pace delivery. John, my neighbor in the villa who had already gotten quite the eyeful of her a couple days before, seemed to find the entire interaction hilarious.
Cassidy re-appeared at our table with two more of the frozen drinks. ‘Um, I bought too many of these, do you guys want any?’ John took her up on the offer, even though he had a fresh beer in hand. ‘McKenna, let’s go dance, I want to dance again and everyone wants to go home!’ While maybe not as hyper sounding as McKenna, Cassidy seemed to be a little “up” as well.
McKenna grabbed Cassidy’s hand and started to head to the dance floor. After a few steps she turned and looked over her shoulder at me. ‘Aren’t you coming?’ she asked me. I caught up and joined the two of them in the crowd. The music was a mix, mostly of stuff from the 90s and early 00s, and the crowd was sloppy at this hour. There were multiple couples grinding on one another, making out, etc. That did include at times McKenna and I, and McKenna and Cassidy did some grinding as well and a kiss or two. Nothing too salacious, just hot drunk girl kisses on the dance floor.
*Reader – since you are here for one thing, I suppose I should describe Cassidy as well, to help complete the image. Sandy brown/dirty blonde hair, a little below shoulder length, with some highlights in it, she was a couple inches taller than McKenna, although she also had on wedges, compared to McKenna’s flip flops. She was also wearing a denim skirt, but hers was a darker wash, and went to mid-thigh, compared to the super weathered and distressed wash on McKenna’s, and as I mentioned before, negligible length below her ass. Cassidy had a short-sleeved white shirt, with a couple buttons. Her chest was I would guess a C-cup, a little bigger than McKenna’s B-cups, but hard to tell exactly what was natural, and what was the bra she had under the blouse. Green eyes, and very full lips with high cheek bones, she looked like she might have some eastern European blood in her somewhere along the way.*
About 15 minutes into that, John joined us out on the dance floor, and said the others from our group had headed back. I could tell he was a little unsure of his place there, as he kept mostly away from direct dancing with the two girls, and it was mostly the two of them dancing, or McKenna dancing with me. McKenna’s own dancing was getting flirtier by the minute, and at one point, she had her hands on the floor and was sort of twerking up towards me. Looking down as she did, I saw her skirt had really ridden up to mid-ass, and with her bent over like that, there was not-so-subtle flashing occurring. Also evident was that the thong she had, which wasn’t all that much fabric to begin with, was sort of pulled over to the side, with fully half her (visibly wet) pussy on display. While that could have been due to the dancing, I suspected it was likely what she had gotten up to before Cassidy had gotten her attention to head downstairs.
In a break between songs, Cassidy leaned over and whispered something to McKenna, who responded in kind. As she broke away from her, I said, ‘what was that about?’
McKenna replied, ‘Nothing, just sort of an inside thing. We’ll be right back.’ The two of them went off to the bathroom, laughing. John and I were still in the middle of the dance floor, and the crowd around us made it awkward to just stop, so we kept dancing. After a few minutes McKenna and Cassidy made their way back, laughing even hard than they were when they left. McKenna pulled my head down and kissed me and said, ‘If I tell you you can fuck my throat later, can we keep dancing? Maybe not here, like somewhere else, I’m tired of the music and there’s some sketch people here. Oh, also, Cassidy wants to get laid tonight…’ as she said that last part, House of Pain’s Jump Around came on, and the entire dance floor started jumping.
I wasn’t sure what McKenna was suggesting vis-à-vis Cassidy, but we could get back to that later. I did note that Cassidy’s breasts were bouncing deliciously as she jumped. The thought that maybe this would be a threesome was definitely in my head now, and I could feel myself start to get a little hard. Still, better to wait for direction before making a wrong move.
When that song ended, McKenna said, ‘We should go to another bar, I wanna keep dancing but not here.’ I saw her looking over behind me and turned to see that it looked like the guy she was “dancing” with earlier was still in the bar with some friends, watching us. The four of us filed out into the street. It was now a little past 2am, and most places were shutting down. We walked around a corner to the Nowhere Bar, right on the water which had an outdoor seating area and a packed dancefloor. I went to get us four waters, and McKenna followed. ‘So what’s John’s story? Is he single?’ I confirmed he was, for the most part. ‘Cassidy thinks he’s kind of cute, he could totally take her home if he wanted to tonight.’ I’d have to share that with him. He had been texting Kelsey from the night before during the day, but it didn’t seem like it was going anywhere, and given the hour, that didn’t seem like a possibility for him.
We brought the waters back, and McKenna and Cassidy went to dance. ‘You should make a move on her bud.’ John looked at me like, “seriously?” ‘Yeah, she told McKenna you’re cute. Strike while the iron’s hot. Come on, let’s join em.’ We walked over to join the two of them in dancing. With some newfound confidence, John danced a little closer to Cassidy, and after several minutes, when each baby step along the way wasn’t rebuffed, McKenna got my attention to the show me the two of them kissing. We all danced there for probably another 15 minutes, but finally at 2:30, it was time to call it a night. The crowd slowly started to make their way out to the marina area, and we headed back towards the hotel area to the east. McKenna was holding my hand and about 10 feet behind us, John and Cassidy were similarly situated.
As we walked by a Farmacia, McKenna shouted back to them, ‘Make sure you use protection you two!’ I laughed, but on turning, I saw Cassidy pulling John into the pharmacy. ‘We’re gonna go on ahead, see you in the morning babe’ McKenna said to them. We walked another couple blocks, and McKenna pushed me into a little alcove/alleyway just off the street. She dropped to her knees and said, ‘I want you so bad!’ while unzipping me and pulling my dick out. She wrapped her hand most of the way around my moderately stiff cock and brought her mouth down to lick her way up the shaft before putting the top couple inches in her mouth. After pumping me in and out a couple times, McKenna popped off to say, ‘I’ve been wanting to do that since you showed up tonight. God I love your cock,’ before putting the rapidly hardening cock back in her mouth.
I groaned, it felt great, but the situation was a little awkward given where we were. The feeling of her mouth on me won out as she bobbed up and down until we had our first interruption as Cassidy and John walked by, hand-in-hand. ‘Wooo, not even waiting for the room!’ Cassidy shouted as she spotted the movement. It really made it clear how vulnerable our position was there. McKenna undeterred, kept sucking me as Cassidy and John walked on.
It wasn’t until another group of late-night partiers walked by that I pulled McKenna up and began making out with her, quickly getting my cock back into my pants before we were in view of them. When we broke the kiss, McKenna said, ‘Oh my god that was so hot, we almost got caught by them. How far to your place?’ I took her hand and we walked the final few blocks, stopping several times to make out again.
*************
Stay tuned for the continuation of this shortly.
Source: reddit.com/r/gonewildstories/comments/zivqw7/running_into_a_familiar_face_in_cabo_mf_part_1
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