Shooting my shot poolside in Cabo [MF]

This is a continuation of the [poolside connections story](https://www.reddit.com/r/gonewildstories/comments/w2tra9/making_connections_poolside_in_cabo_fm/?) posted earlier. Hated to split it up, but character limits are what they are.

After breakfast, a group of us headed out to do a little shopping ourselves. After a couple hours of that, I had my fill, and returned to the resort, decided to hit the pool again. When I got there, I saw Robin sitting in the shade wearing a black cover up over a black bikini. I walked over and asked if her husband was on his way down to join her.

‘Oh don’t even get me fucking started!’ she replied in disgust. ‘After a day of catching nothing by a sunburn and a hangover, he got a text this morning offering a second chance for half the charge. We had plans to lay by the pool today, but as you can see, I’m solo.’ I commented that at least the weather was a little cooler than the day before (granted, it was 86 or so, as opposed to low 90s, but every couple degrees helps).

‘I see you decided to go with one of your *other* suits.’

‘Yeah, but I’m terrified to take off the cover up, so no going in the water for me. Even in the shade, I’m sort of melting here!’

‘Can I buy you a drink at the bar then?’

‘Oh, I could soooooo use a drink right now.’

We walked up to the bar, which in addition to shade, had fans circulating some air. Robin wanted a margarita, while I got a paloma. When our drinks arrived, I toasted to the dinner we separately had last night.

‘How was dinner anyway?’

‘Oh my god, that was so sweet of you!’ she said. ‘Not that it was the romantic dinner I wanted. I mean, it would have been, but Matt showed up here loaded, and then drank throughout dinner. By the time we got home, he was a mess.’

‘Ugh, that’s too bad.’

Somehow, even though Robin had just gotten the margarita, she had nearly downed it, and called the bartender over for another.

‘Did you want to get something to eat?’ I asked her. We decided on two salads and ceviche. While we waited on the food, Robin finished up the second margarita. She went to order another, but I encouraged her to have a Topo Chico first before having another. I could tell alcohol goes to her quickly, and coupled with the sun, it could be a long day for her to get tanked just after noon.

We dug into the food when Robin spontaneously returned the conversation to a topic from earlier. ‘And you know the worst of it?’ she said, while I followed along not knowing where this was going. ‘I had shaved some things in anticipation of wearing this suit today, and when we got back to the room last night, thought I would try some lingerie, even though I was pissed at him. I came out of the bathroom, and that fucker was snoring in bed. Fuuuuuurrrrrriouss. So here I am now, in the swimsuit I haven’t worn since our honeymoon, when I was probably 20 pounds lighter, feeling like a fool, and can’t even get sun in it I’m so embarrassed.’

‘Nothing to be embarrassed about, I bet you look great. At least, from what I can see.’

‘Which isn’t much, thank god. Seriously, I do not know what I was thinking. I can’t be seen in this without the coverup.’

‘You know, if you want to get sun, we do have the private pool at our villa. The couple and guy I’m sharing it with are on a sightseeing trip all day, so no one will be there.’

‘No, I couldn’t. I don’t even think I could let you see it.’

‘Sure you can. I bet you look a lot better in it than you think.’

She called the bartender over again and asked for another round of drinks for us both. She took another deep sip, and said, ‘okay, but you have to be honest if I look ridiculous in it.’

We walked over to my villa, drinks in hand. Robin was effusive in her praise of the actual room layout. I could tell this was a sore point after the debacle of the booking her husband had done that promised something and delivered something very different. When I led the way out to the deck and pool, she just shook her head before saying, ‘Yes, this, this is what I was promised.’

We made our way to the pool, and I went into the villa to grab some waters for us. When I came back out, Robin was on a pool lounge chair, and had lost the cover up. She was applying sunscreen, and the tan lines between her suit from yesterday and today were noticeable. Around her bust, where the black suit today was much smaller than yesterday’s, she was near white. ‘You tan up quick I see.’

Robin reached her hands up, almost to block the view. ‘Oh, I’m so pale, this probably looks awful.’

‘No, not at all, I just meant you got some tan yesterday it appears.’

‘Yeah, I can get tan pretty quick. When we got back from our honeymoon my mom was so mad at how dark my skin was. A week in Jamaica, wearing this suit for most of it, I was verrrrrry dark. Totally goes against our culture.’

Her hands were still covering both breasts. I noticed the tan lines at the bottom of the suit were also slightly pronounced. The bottoms were lower cut in the front, and higher cut on the sides, far narrower as well. ‘The suit still fits you though, so congrats on that.’

‘I feel like I’m spilling out of it, and not just up here’, she said, removing her hands from the cups.

‘I think you look good. You could totally rock this at the pool.’

‘Definitely not, you haven’t seen the back, and I don’t think I want you to.’

She continued applying suntan lotion before laying back, sipping her drink. We got to talking about her family, her being the child of refugees whose parents moved to Minnesota as kids in the late 70s. She touched briefly on her relationship with Matt, and how things had just sort of stalled out over the past year. ‘I brought this on the trip hoping it would remind him of our honeymoon. But I guess you can’t expect your sex drive to be the same at 30 as it was at 23, at least if you’re a guy.’

‘I think that varies from person to person. Mine was pretty high in my early 20s, but I wouldn’t say it’s that different now, to be honest.’

‘Mine is so much higher than it used to be, but Matt’s has just dropped off. Oh my god, why am I sharing so much with you?! I’m tipsy, in case you haven’t noticed!’ she said as she sipped the rest of the third margarita. ‘Downside of private pool is no bartender to keep your drink refilled!’

‘Do you want to try the paloma?’ I asked, as I hadn’t yet had but a sip of that second round of drinks. Robin sat up and crossed her legs in front of her as I handed her my drink.

‘These bottoms are as small as my underwear! Oooh, this is good, I’ve never had one of these before!’

‘They aren’t the smallest bottoms I’ve seen down here this week.’ Which was true, and not just counting McKenna’s.

‘Yeah, but those girls are in college and didn’t have to shave things for the first time in five years.’ She made an “Oh!” face right after saying that last part.

‘You mentioned earlier, and the lingerie fail.’

‘The lingerie wasn’t a fail, my sleeping husband was the fail.’

‘I’m sure he’ll appreciate it at some point.’

‘At this speed, it will have grown out by the time he pays any attention.’ She took another deep sip of the paloma, before saying, ‘Ok, I’m gonna turn over, please don’t make fun of my butt.’ Robin put the drink down and moved to turn over. Other than the paleness of where her suit had covered, it was actually a pretty good butt, to be honest. The bottoms were definitely not the smallest I had seen, but she was right, they were comparatively small, with a scrunch thong separating her two cheeks, probably an inch thick fabric.

‘Nothing to be ashamed of there Robin.’

She turned her head, ‘thank you, I appreciate the compliment. Umm, could you put lotion on my back?’

‘Happy to!’ I squirted some lotion in my hands and applied it to her back, going under the thin straps of the bikini top, working my way down her back to the top of the bottoms. ‘Can I do your butt for you too?’

‘Oh, you don’t have to do that, I can do it.’

‘I didn’t say do I have to, I said can I.’

She looked back at me, lowering her glasses and giving me a smile. ‘You’re bad. Don’t make fun of my cellulite.’

I squirted more lotion onto my hands before starting at the top of her ass and working my way down. There was maybe a dimple or two, but nothing for her to be ashamed of. As I worked my hands down, I got to the line where the bottom of her ass connects to her thighs. I traced that line inward, bringing my thumbs up towards the crack. My thumbs grazed the edges of the thong, rubbing the suntan lotion in there before asking, ‘Want me to do the backs of your legs as well?’ She agreed, and I started at her calves, working my way back up until I was back at her ass. ‘Robin, you’ve got a nice ass, seriously, no need to hide it.’

She looked back at me again and said ‘thank you. I wish Matt thought so. Maybe because I was 19 when we met, but any time he talks about it, it’s just about how it’s not as perky as it was then.’

‘He’s an idiot.’

I laid back down on the lounge chair next to her. She was opening up quite a bit, so I thought I’d continue to engage in that line of conversation. ‘Things aren’t as frequent as you’d like then?’

‘Sex? No. We had sort of tailed off, then when we both had to start working from home, it was kind of a spark for a couple weeks, like during the day even. Then that tailed off. Once a month, twice a month if I’m lucky, always missionary.’

‘Always? Like, no variety? Not even doggystyle?’

‘Oh my god, I can’t believe we are having this conversation. No, never doggy. Not since we got married. Maybe once on our honeymoon I guess? He has weird hangups about butts.’

‘How unfortunate. If we’re being honest, what about oral?’

‘Oh, he loves it’ she said laughing, ‘asks for it all the time.’

‘Asks to give?’ I said laughing.

She continued laughing, ‘Oh please. Those hangups extend I guess.’

‘Wow, he’s missing out. I guess so are you.’

‘I have learned to take matters into my own hands. Okay, enough about this. Let’s get in the water.’

We both got into the pool, which was refreshing with how warm it was. Our chat became more mundane, talking about travel, food, books. ‘This is so nice. I wish my room had one of these. If only we had more drinks.’

‘We’ve got some stuff inside. I don’t think I can make margaritas, would you want another paloma?’

‘Yes please, that was great.’
I went back inside, made us two palomas and returned to the patio. Robin was getting into position to lay back on her stomach on a chair. I walked towards her and handed her a drink, while she was still on all fours. ‘I would be eating that daily.’

‘Excuse me?’ she said, laughing again.

‘Just sayin, your ass looks great, especially in that position. Matt’s seriously nuts.’

‘You’re sweet. Hey, I think the suntan lotion came off, since we didn’t wait long enough. Could you put more on?’

I grabbed the lotion, spreading it across her shoulders and back before moving down to her ass again. As I did, I grabbed it a little more firmly. I did the same move with my thumbs along the edges of the thong, but let my thumbs travel just a touch inside the edge of the fabric.

‘Ohh’ Robin exclaimed but pushed her body up slightly. ‘Wow, that was unexpected.’

‘Didn’t want you to burn. Sometimes you need to go a little under the suit, just to make sure.’

‘Good thinking!’

‘Want me to continue?’

‘I don’t want to burn. But no funny business.’

I put a little more lotion on and rubbed it slightly under the strap of the bottoms, starting up at the waistline, before moving back down to the thong separating her cheeks. I brought my thumbs down that line until I was just above her asshole. ‘You said no funny business, right?’ and pulled my thumbs away from the suit before getting more lotion and working my way back up her calves, knees, and thighs. As I *slowly* worked my way up her inner thighs towards her bikini bottom, I could see she was squirming a bit, and not in what I perceived as an uncomfortable way. I ran my thumbs again right against and slightly under the fabric, this time clearly stroking the edges of her outer labia, eliciting a slight moan from Robin.

My hands were now gripping both cheeks, with just a little tension pulling out to spread them slightly. ‘Just sayin, if my wife were wearing this bikini, I wouldn’t be miles out to sea, drinking with guys and trying to catch a fish. I’d be on my back with her riding my face.’

‘Wow, that’s quite a visual.’ Robin replied, ‘That is something I’ve never experienced.’

‘Oral sex?’

‘Of course not that, umm, riding a face as you said it.’

‘It’s one of my absolute favorite ways to do it.’

‘How many other ways do you have?’

‘I could tell you or I could show you.’

‘Out here, right now?’

‘I don’t know whether to take that as incredulity or a request.’ Robin didn’t respond, hesitating. I pulled the cheeks slightly further apart, leaning in and placed my tongue flat against the thong, right above her asshole.

‘Oh! Oh my god!’ she exclaimed. At first, I wasn’t sure if that was a statement of panic or pleasure, but as her body then responded an instant later by tilting her ass right up at me, I took it to mean the latter. I took the opportunity to flick my tongue slightly across the skin on either side of the thong, eliciting a further moan.

I continued to flick my tongue against the fabric and adjacent skin around her asshole for 30 seconds or so, my hands on her two ass cheeks pulling them apart. Hearing no objections, I pulled her thong aside with my left thumb, and made the first direct contact between her asshole and my tongue. I ran my tongue around the edges of it before placing it flat against her asshole and putting a little pressure on it. ‘Oh my god, oh fuck.’ Robin exclaimed.

I pulled back for a moment, now getting to take in what her asshole looked like. Tight little pucker, but most noticeable was how much darker it was than the rest of her skin. I could only see the ‘back’ of her pussy, so to speak, but her labia appeared darker as well. Her pussy was wet from what I could see, and at least in that position, her labia were slightly open as well, showing the pinkness underlying.

I move my mouth back to her asshole, going perhaps even a little deeper. The taste below her suit was primarily suntan lotion and the pool water, but as my tongue penetrated her ass, I could taste just the slightest bitter taste of asshole. ‘Oh fuck, this is so weird, but… ungh, that feels so good!’

I was still holding the bathing suit to the side with my left hand, and brought that hand down slightly to move more of the suit to the side to expose her pussy. I pulled my tongue back, got another look at her pussy, noticing her lips were even wetter and were pretty well parted, before bringing my tongue down, this time starting at the ‘bottom’ of her pussy, licking down (with her in a doggystyle position) towards her clit. ‘Oh my god, oh fuck, that is so good.’ Robin said aloud.

Her pussy was soaked and while the suntan lotion flavor wasn’t there, it was a mix of a salty sweet female wetness and pool water taste as I licked my way down. When I reached her clit, I could sense her gripping the side of the lounge chair she was kneeling on as she said, ‘Oh right there, fuck, oh god, yes.’

I tried out a few different techniques to see what was going to work best for her. The swimsuit pulled to the side made everything a bit more difficult so after several minutes of it, I used both hands to just pull them down to her knees before resuming my ministrations.

Robin had responded most vocally to a light butterfly flick of her clit, and so I resumed that action, with her responding positively again. After about 5 more minutes of this, Robin said, ‘Oh yes, right there, don’t stop!’ followed by ‘Oh my god, oh fuck, oh my god, ohhhhhhh!’ as she came.

I kept going at her clit with those butterfly flicks for a few seconds after before Robin said, ‘oh, so sensitive, I need a little break’. I move my way back up towards her wet vaginal opening, take a deep stroke of my tongue up between her labia and dipping into the opening before returning to the asshole that started our fun.

‘Oh my god, I had no idea this could feel so good.’

I continued licking her there, bringing my tongue around in circles around the rim, poking in lightly, and then driving it in my deeply and circling around inside. Each movement brought verbalization from Robin, and when I brought my thumb back to her clit while doing so what had been mostly talking turned to unintelligible mumbling and moaning. That is until she started to buck her hips slightly up towards me, my tongue embedded at least an inch into her asshole, my thumb stroking her clit quickly when she exclaimed, ‘Oh don’t stop I’m cumming!’

After that second orgasm, Robin pushed herself up and turned before sitting back on the chaise lounge, now bottomless. She turned to me and said, ‘I can’t believe that just happened. That was unbelievable. I haven’t had an orgasm from oral in like six years.’

‘Really!’

‘Well, I haven’t *had* oral in at least four I guess, but even then, it was foreplay, not something I could come from. And don’t even get me started on the other stuff you did there. That was, umm, something.’

‘Glad you enjoyed. Only three or four other ways of doing it to show you.’

She gave me a quizzical look before a moment of recognition, then saying, ‘Oh my god, you’re so bad!’

She looked at my again, sort of biting her lip, and said, ‘I shouldn’t even be here, let alone letting that happen, but my god, that was so good. I, um,’ a pause, quite a pregnant one, ‘what can I do for you?’

‘Whatever you’re comfortable with.’

‘I don’t think we can have sex, that just…um’

‘I get it.’

She moved off of her chaise lounge and move over to my own, kissing me. My face was still wet with saliva and her wetness, my tongue having just been in her ass. It was a quick kiss, but the fire in her eyes seemed even more intense afterwards. She kissed her way down my chest and abdomen before pulling the tie on my swimsuit bottom and then pulling them down slightly. As she did, I heard a small gasp.

‘Umm, has anyone ever told you you’re big?’

I laughed, ‘Yeah, once or twice.’

‘If I hadn’t already said we weren’t going to have sex, I would say it now. That would never fit.’

‘You’d be surprised.’

‘Well, doesn’t matter, but I can still try to make you cum like this.’ she said before moving her mouth down and opening her lips around the head.

I let out a small moan as her lips and tongue surrounded the head and she began to suck. She did appear to be struggling a bit to get me into her mouth, which was definitely on the smaller side, as far as mouths go. I was going to encourage her to use her hand as well when what sounded like a group of people came out to the patio of the adjoining unit, making a bit of noise. It startled Robin and she looked up at me, pulling off, panic in her eyes. ‘I don’t think we should do this out here.’

‘I don’t think they can see us.’

‘Umm, I’m just not comfortable.’

I stood up, my swimsuit dropping to the ground as I stepped out of it and grabbed her hand to lead her inside. I was naked while she was bottomless. We went to my room, and I led her to the bed. I thought perhaps getting her off again would remove the anxiety she seemed to be carrying from the “close call” at the pool and had her lay back for a more “traditional” attempt at cunnilingus.

‘I thought it was my turn to, you know.’

‘Just lay back and enjoy, seems like maybe you deserve one or two more orgasms.’

Robin didn’t object to that and laid back. I spread her legs as far as I thought she could comfortably go, taking in the slick, dark brown labia with above it. I caressed my hands up her body towards her breasts, and pulled the bikini top up, releasing them from the maybe just slightly too small bikini. Her nipples were of a similar color to her labia. I lightly pinched her nipples before taking one in my mouth, then moved back down towards her waiting pussy.

Starting at her vagina, I licked my way up, my tongue getting coated with the slick, slightly salty wetness that had formed since my tongue was last there. Licking up until I got to her clit, I began to again flick it lightly, while my thumbs stroked both labia up and down, lightly massaging them. ‘Oh my god, I love this’ Robin said. After a couple minutes, I began to circle my middle finger at her opening before sliding into her. ‘Oh fuck, oh that is good.’ she said aloud.

Still focusing on her clit with my tongue, I stroked her g-spot with my finger before sliding my ringer finger in aside it. While her labia gaped a little in their natural state, the two fingers inside her seemed to take up all the real estate as her vaginal walls squeezed tight against them. With the thumb of my other hand, I began to run light circles on her asshole, using the saliva and wetness from above to make those strokes smooth. Hearing Robin begin to coo, I lightly push pressure on that thumb starting to slide it into her.

When my thumb breached her sphincter up to the first knuckle Robin said, ‘Oh fuck, I’ve never had something in there!’. I pulled back to ask if it was okay when she said, ‘Don’t stop licking me, oh my god I think I’m going to cum again.’

Moving my tongue back into position I redoubled my efforts with my fingers and slid my thumb in to the webbing of my hand. Robin moaned unintelligibly before saying, ‘Oh my god I’m cumminggggggg’ as both her pussy and ass contracted around my digits.

Having learned how sensitive she was earlier at the pool, I removed my tongue, fingers, and thumb once she stopped contracting, and brought my tongue down to her labia, licking them slightly just to keep *some* stimulation going. Robin didn’t object, and brought her hands down to my head, running them through my hair before saying, ‘This is so fucking good.’

After a couple more minutes of that licking Robin said, ‘Ummm, would you, umm, lick me again, you know…’ I knew exactly what she was asking for, but thought I’d have some fun with it.

‘Lick you again how?’

‘You know, back there.’

‘Back where?’

‘Oh my god, I can’t even say it! My, you know, ass.’

‘Where on your ass, I want to hear you say it?’

‘My asshole, lick my asshole’

‘There you go. I won’t make you beg for it.’

‘Thank god, that would be so embarrassing. *Oh please, please lick my asshole sir*’ saying the former in a mocking, whimpering voice. She may have been joking, but it was still hot to hear.

I pushed her legs back, knees on either side of her chest, bringing the tight, brownish pucker of her ass into view. Holding her in that position, I began to lick at her ass. With it been penetrated by my thumb just minutes earlier, it wasn’t as tight and my tongue was able to enter easier. Robin began to moan as I did. I pulled back and she said, ‘Oh, please don’t stop!’

I responded, ‘Hold you legs back for me’ and as she did, I brought my hands down to pull the skin on either side of her asshole apart even more as I brought my tongue back down to it.

In that position, with my hands pulling on either side, her asshole was just slightly gaped, and I inserted my tongue a half inch or so inside, swirling it around and feeling the muscle contract around me. Robin was moaning ‘oh god’ frequently as I did so. She then said to me, ‘I can’t believe how good this feels. I don’t want this to ever stop.’ I wasn’t going to stop licking to respond, and after another minute or so, she said, ‘Um, can we try that other position you mentioned?’

I pulled back and again thought I would play with her a bit. ‘Which position is that?’

‘I think you called it riding your face?’

I made my way up onto the bed and laid down. I noticed the precum on the head of my cock was glistening, and had started to drip down when I was kneeling in front of her. As I laid down it formed a string between the head and my abdomen. ‘Which way do you want me to do this?’ Robin asked me.

‘Up to you.’ I replied and she made her way up. She started with her back facing down towards the foot of the bed so she could hold onto the headboard. As she straddled my face, I saw her labia opening up, swollen with arousal and dripping wet. I grabbed her hips and brought her down to my tongue, licking up the wetness that had accumulated- before making my way up to her clit. As I began to flick my tongue there, Robin said, ‘Oh god, this is so good.’ I continued licking as she repeated that phrase several times.

She was grinding herself onto my tongue and mouth as I did and as her pace increased, so did the pace of her verbal expression of pleasure. ‘Oh my god this is so good I’m going to cum!’ she said before pressing firm down against me. Robin then lifted up slightly looking down her body at my eyes, her pussy hovering an inch above me. I continue lightly licking up and down her labia as she said, ‘I don’t think I’ve ever cum this many times. I usually can’t take much after it happens but this time, it’s like I can’t get enough. Can I try it the other way?’ Looking her straight in the eyes while I continued licking I just nodded at her.

Robin spun around and resumed her sitting position hovering an bit above me. Starting at her clit, I licked my way back before bringing my tongue right back to her asshole. Opening my mouth, I made my tongue firm and pulled her down towards me, effectively impaling her asshole with my tongue, albeit only a couple inches. It was some of the most aggressive oral-anal contact I had had this year, but given how much she was enjoying it, I thought I would try to go above and beyond. I could feel Robin’s pussy splayed around my chin as she leaned forward slightly, resting her hands on my chest. It was entirely erotic and I could feel my cock, still rock hard, continuing to leak precum.

‘Fuck, your cock is so big’ she said, ‘are you cumming right now?’

Lifting her just slightly, I said, ‘no, that’s just precum’, although I’m positive it didn’t come out nearly that clearly, since my tongue was still partly in her ass. As I pushed my tongue back into her, I felt her weight shift a little, and one hand grab my cock firmly. Robin bent down a little, changing the position of her ass relative to my tongue so that only the tip was now inserted into her tight hole. I flicked it a couple times before licking across her perineum and down to her pussy, which was now spread further from having been “penetrated” by my chin for several minutes.

I felt Robin take the head of my cock into her mouth as she bent further down and matched her motion by bringing her hips up and my tongue down to her clit. Her lips and tongue were lapping at my cock, presumably licking up the precum that had been pouring out and glazing the head and shaft.

Robin moaned around my cock as my tongue began flicking at her still swollen clit, and I felt the hand that was holding the shaft start to pump up and down. The combination handjob blowjob was better than just the mouth on head action at the pool (not that that didn’t feel great itself), and we continued in that 69 position for several minutes, my nose now taking the place of my tongue with the tip of it now penetrating her asshole.

I went back to the butterfly flicks that worked so well previously, with perhaps a little more pressure, given how aggressively she was pushing back against me. I continued licking her like that for several more minutes as she continued pumping my cock with her hand while she continued moving her mouth up and down the head and top inch or so, sucking all the while.

Her grip was tight and while it wasn’t the best blowjob I’d had, it was enough friction, coupled with how hot the entire afternoon had been, I felt myself getting close. I pulled back for a moment to tell her that I was getting close, wanting to give her warning when she pulled her mouth off of me to say, ‘Oh keep licking me right there, I’m gonna cum!’

I immediately went back to her clit, focusing on the spot I had been at, as her mouth moved back to my cock. She was moaning around it while bucking her hips, and I could feel myself reach my own tipping point. As the first shot rocketed out of my cock, I heard the telltale sound of a sputter as it hit the back of her throat. It had been probably 32 hours since I had last cum, and in my experience, when there’s that much time, and just a single orgasm in the preceding day, my first orgasm the next day is quite big.

My cock spasmed several more times, at least eight I would suspect, and Robin’s lips were tightly sealed around the head as it did. I could hear her attempting to swallow, and she was sucking hard on the sensitive tip. On my own part, I was still licking her clit as she did, or at least attempting to as I moaned through my own orgasm. When my own spasming stopped, I felt Robin’s mouth pull off and she pushed herself up, still sitting on my face.

‘You just, mmmm, came so much. Oh god, I’m so sensitive but I can’t stop cumming on your tongue.’ She was now rocking back and forth on my tongue, my nose brushing against her asshole and taint. ‘I’m so close to cumming again, just don’t stop.’ She rocked on my face for several more minutes before she came one more time.

When that orgasm finished, she moved a leg up and laid down next to me. Looking over at her, I saw a dribble of cum leaking down from her lip and down her chin. ‘You’ve got a little something there.’ I said, and she used her tongue to lick up the top of it, before using a finger to get the rest.

‘I cannot believe that all just happened. I have never, umm…’ not finishing the sentence as she drifted off. Looking at the bedside clock, we both realized it was now almost 4, and it was hard to say when her husband would return. We got up, and as Robin put her bikini top back on (having taken it fully off while riding my face), we realized both of our swimsuit bottoms were outside along with Robin’s pool tote. After a quick bathroom break,

We walked through our suite (which was quiet still) to the patio sliding door. Robin apparently got a little self conscious, and didn’t want to walk out bottomless, and hung out on the covered area of the patio while I made my way out to the pool. When I got to the chairs we were at, I saw that rather than out bottoms being on the ground, they had been picked up and laid out on the chairs. There were a couple other towels laid out as well, so clearly someone had been around while we were in my room. I made my way back, carrying our suits and her tote.

As I made my way back to the covered patio of the suite, I handed Robin her tote and the bottoms. She stepped into them and was sliding them on when the patio door of the bedroom occupied by the couple opened and the wife of the couple walked into the same area that Robin and I were standing in, quickly followed by her husband. The two of them were adjusting their suits and looked at us in a startled manner.

Robin quickly pulled her suit up the rest of the way while I stood there, similarly surprised by their presence. The two of them were in their early 50s, and the wife’s eyes immediately darted to and locked on to my member, hanging free, still at a 75% chub and completely unencumbered by clothing, or for that matter hair. Her reaction was priceless, silent and open mouthed, her hand quickly covering her mouth as I made a move to cover my junk (albeit somewhat in vain).

The two of them quickly returned back to their room, while Robin and I retreated to the main room of the suite and slipped back into my room. ‘Oh my god, I’m moritified!’ Robin said.

‘I wouldn’t worry about it, I think they were just as embarrassed as we were.’

‘Well you have nothing to be embarrassed about’, gesturing to my cock, still hanging free. ‘So, I need to get going. I just have to say, that was unforgettable, I mean it. Thank you.’

‘No need to thank me, I’m glad we met.’

‘I don’t want this to be awkward later, so if I see you later and act like I don’t know you, don’t let it get weird.’

‘Totally agree.’

‘I’ll let myself out, but before I do…’ and Robin closed the gap between us and kissed me deeply, grabbing and squeezing my cock.

When we broke the kiss, she turned and left my room and I heard the main door open and close shortly after. I straightened up the bed before jumping in the shower, and when I was done, grabbed my phone and returned to lay down on the bed for a bit. Checking my phone, I had a rather suggestive text from Stephanie, a physical therapist I had hooked up with 5 times already this year at this point.

S: <Schedule @ work changed & just got back from gym>

<What r u up 2?>

Me: <In Cabo w friends>

S: Frowny face emoji

<U should have brought me w u>

<I need your> eggplant emoji

Me: <Oh yeah? Where do you need it?>

S: <Everywhere>

<So horny>

Me: <Show me>

A few minutes pass, three dots appear, then disappear, then reappear. Next thing I know, I get a pic of Stephanie’s always perfectly shaved, fantastic looking pussy, soaking wet.

Me: <Mouth watering> and the water drops emoji

S: <2 bad you rnt here to enjoy>

<Now I have to get myself off alone>

Me: <We could facetime>

10 seconds went by before she Facetimed me. I haven’t yet posted a story about Stephanie, and definitely plan to, but at the gym, she was a machine. She went beyond athletic and was straight up jacked. Her nude body on my phone looked phenomenal and she quickly got into a masturbation session, with Stephanie using a dildo and a vibe on her clit. She wanted to see my cock hard, so I started to stroke for her as well.

We were several minutes into it, when there was a knock at my door, followed by ‘Jack are you there? I just wanted to apologize for the interruption on the patio.’ It was Becky, the female half of the couple that had the master room of the suite.

‘Yeah, no worries, all good.’ I replied as I turned my attention back to Stephanie on my phone, who now had four fingers inside her pussy and looked damn close to cumming.

I meant my reply to my suitemate in a “don’t need to worry about it” manner, but she apparently took my “no worries all good” to mean come on in and apologize. So next thing I know, she’s standing in my room, looking down at my naked body laying on the bed, full rock-hard erection while Stephanie is crying out something about me fucking her with my thick cock over Facetime. After what felt like a 30 second staring contest between her and the head of my cock, eyes fully wide, she turned and walked right out the door.

After Stephanie finished, we ended our call and I got dressed. When I came out into the room, there was a note of apology about the second intrusion and that they had left for dinner with a sub-group of our group. John, the other guy staying in my room seemed to be out as well. I headed out to the pool bar area to grab something to eat and drink.

While at the bar, I ran into Rachel from the gym with her husband. We made some light small talk. I offered to buy them drinks, but they declined. Rachel gave me a sly smile as they went to sit at a table. About an hour later, Robin showed up with her husband, who again appeared three sheets to the wind. There was no seating available in the restaurant portion of the bar, so they ended up sitting at the bar, directly across from me. Robin and I caught each other’s’ eyes quite a few times, but I tried to keep to our agreement.

After I finished dinner, I went across the way to the rooftop bar I had visited the night before. It was about the same vibe as before and while there some potential promising encounters, including one with a bachelorette who had way too many margaritas, nothing proceeded past kissing. I called it a night and headed back to my place, alone, for a night of sleep.

Source: reddit.com/r/gonewildstories/comments/w2ts73/shooting_my_shot_poolside_in_cabo_mf