If on an Island a Traveler Pt. 01

[This story was written while vacationing on an island. The sun was hot, the mood languid. Consider this a slow open. No actual sex; just some light voyeurism and plenty of sexy ruminations and fantasies, to be realized in the next installment(s). Happy reading.]

*****

His POV:

If you're going to be jilted, Barbados is not a terrible place to drown your sorrows. I planned this trip months ago with my lady love, only to be informed just last week that she'd changed her mind and that her feelings for me have "evolved." Classy dame that she is, she didn't want to half-heartedly go on a romantic exotic vacation under false pretenses.

Understandably, I was crushed and my kneejerk reaction originally was to 86 everything and use the flight credit for another trip. But when I checked my reservation online, I saw that the cancellation window without penalty was 7 days' advance notice, and I was half a day shy of that. I could eat the 50%, but upon reflection, I had already scheduled the time off, and rather than eat the penalty, why not just go myself. It's only a 4-hour flight from JFK.

So, I arrived yesterday afternoon and didn't do much, just a quick dip in the pool then puttered around the duplex rental getting set up. In the early evening, I drove a mile down the road for traditional Barbadian food and some cold brews, then turned in early. The AirBnB was a luxury 2-bedroom with 2 baths, way too much space for me. I'm a consultant and anticipated needing the second room to make calls and do some work, but now as a party of one, the place seems cavernous.

The entire property is actually two apartments, the other one looking just like mine from the outside and seemingly unoccupied. I assume it's either the owner's unit or another rental. In back is a pretty pool, about 20 meters long so not huge but just long enough to get a few short laps in. Decades ago in college, I was a competitive swimmer. Now at 54, I still try to get some laps in whenever I can to keep fit.

It's late April so it gets quite hot by mid-morning. The pool area is in full sun until noon then enjoys shade in the afternoon. The first morning I'm there, I go for a swim early in the morning before the heat of the day. Upon coming back inside for some fruit and coffee, I notice there's a second car in addition to my rental in the 4-car lot in front. As any city-dweller, I feel a twinge of disappointment, thinking I had the property to myself for the short week I'm here. Well, as long as they're not noisy. Let's hope for no kids, this being spring break for many.

After breakfast, I drive into town to have a look-see before coming back to take some calls that kept me busy for a few hours before and after lunch. By 2pm I'm ready for the requisite tropical siesta - nothing else to do during the hottest time of the day. As I close the drapes to ward off the strong afternoon sun and set the A/C to take the heat down a bit, my thoughts turn to my lost lady love. Had she been here, we would certainly have made love last night, and probably also this morning. And right about now, we would likely lie in for some lazy fondling, with me eventually eating her out or rimming her ass and bringing her to a climax or two.

I'm fit but as an older guy, I need to pace out my orgasms, which doesn't prevent me from giving the lady in my life a lot of pleasure. I've read up on seminal retention and while I don't practice it in the esoteric sense, I can enjoy copulation and two-way oral sex without necessarily losing my semen every time and just letting it build up. My lady liked it, too.

It was a huge turn-on for her that I could be ready for her just about any time without fully climaxing. And likewise, she enjoyed the power of eventually making me lose control and gifting her my saved-up cum. Too bad that wasn't enough to keep her on. I guess if I were honest with myself, the great sex was the main thing holding it together towards the end.

It's very pleasurable to make leisurely love without the impatience of youth. It's better if I ejaculate at most every few days, or better yet, once per week or even less. Bonus if at least once of those times is in a nice, tight ass. I do love every single aspect of lovemaking, but especially anal sex. I crave licking out a tight anus, slowly teasing it more open with my fingers, or with toys, and eventually with my cock.

As I'm thinking of her, I'm fondling my cock in the semi-dark cooled room. Mmmmm, it would be lovely to have her here right now to wrap her sensuous lips around my cock. She knew exactly what to do to keep me on a slow burn and knew precisely when to taper off to keep me on a low simmer for later. In remembrance of her, I'm masturbating to the same cadence that I imagine she would take at moments like these. Eventually, I do slow down to rest my cock and drift off for a cat nap.

I wake up with a start, the timer on the A/C having gone off and the room feeling stuffy. I check my watch and see it's already 3:30pm. Longer than I had planned to rest but perfect timing for a mid-afternoon swim, the sun well past its apex and the tall hedges lending a nice shade to the pool area. I peek outside to see if my new neighbors might be down there. Please, god, let there be no pool floats or radio.

There is just one lone figure on a lounge chair, a woman in a two-piece, lying face down, face turned to the shaded side facing away from me, cheek on crossed forearms. Her swim bottom is not terribly revealing in the back, the seat mid cut so just a bit of butt flesh shows but still modest. She is slim but shapely, nipped waist which makes her hips seem wider even though they're not. Nice ass, from what I can tell at this distance.

I'm wondering if I should wait a few and give her space. Who knows, perhaps she was hoping to be here on her own as well, or maybe she's taking refuge from her kids. Somehow she didn't seem like a mom to me, though. Impossibly to know her age range from this distance, but that butt doesn't look like a mom butt. Just thinking about butts, in general, makes my cock perk up and I lazily glide my hand over my boxers. Maybe I should have rubbed one out earlier, after all. It has been a week since I last gave my old girlfriend a semen sample.

I go to the kitchen to get a cold drink as I ponder my stratagem. Do I go to the pool? Do I go in town and swim later? Am I over-thinking it? Finally, I decide, fuck it, I'm going for a swim. This trip is already compromised by one woman; why should I let a total stranger affect my plans.

I pull on my trunks and put on my shades to go outside. She's on the other end and still facing down so I don't need to greet her. Not to disturb her, I slip into the pool rather than diving in and pull about a dozen short laps. I do love swimming. It always resets me in a good way.

Once I'm done with the first set, I need a pee (should have gone before I came out) so go inside, and while I was at it, grabbed a cold brew. This is one of the best feelings: a cold one after some exercise. Back out on my patio, I see the woman has turned over and is lying face up, knees bent with feet apart and knees together. She has an oversized sunhat over her face and at the pool's distance away, I still can't see what she looks like. But her proportions look pretty good from here.

I slip into the pool again, swim to her end, then back, then back to her end again. I come up for air on her end and under the pretext of taking a break, I stay a few breaths and check her out. With her feet flat on the chaise, I can admire her beautiful toes and high arches. I do have a thing for feet, not gonna lie. My horndog eyes trail up to take in her long, toned legs; her dimensions make her out to be tallish, maybe 5'8". Absent-mindedly I wonder if she's a swimmer, too, and continue my gaze to her chest.

If her suit looked modest from the back, it certainly made up for it in the front. The two triangles of fabric covering her chest were minimal, showcasing her small breasts and perky nipples. Fuccckkkk, even more than pretty toes, small perky tits are my downfall. There is nothing like fucking a woman from behind and fondling her small swells and pebbly nipples with both hands. Especially if my cock is embedded in her ass. Once again, my cock is perking up in my trunks. I duck-dive back into the water and stroke back to my end, grateful for the water tempering my semi.

I get back out and set up on my own lounge chair, returning to my ridiculously small 25-cl beer. The mystery woman stirs on her chaise and shifts the hat onto her head now, adjusting her chair so that she is half-reclined. She spies me and raises a hand in a half greeting. I motion back, equally nonchalant. She then leans back on her chaise. She's too far away for me to see if her eyes are open or not. I guess it doesn't really matter.

+ + +

Her POV:

What a drag. Since my best friend bailed on me on this trip, I had gotten used to the idea that I would be solo for some me-time. I was looking forward to a change my surroundings to get some writing done. So naturally I was a bit disappointed to see another car in the drive when I pulled up to the rental. I had hoped it was the property manager or cleaning staff.

It's now past the hottest part of the day, and I'm laying out by the pool enjoying the solitude when out of nowhere there's a guy on the other side coming out of the duplex. Hopefully he's here with someone and not alone, potentially on the make. I hope he's not chatty. Please god, don't let him chat me up.

I ignore him until he finishes his laps and goes inside. Thank god. I flip over and add some SPF to my chest between the panels of my plunging bikini top even though it's nearing 4pm. Peeling sunburned cleavage is no bueno. If I had known I would have a neighbor, I would have worn my other suit. Oh well, let him look if he wants to. I'm not shocking anybody with my A-cup tits, unless that's what gets him off. There are guys like that, Lord knows.

Even with my hat on my face, I could see him discreetly checking me out from under my eyelashes when he did his one and a half laps and paused on my end. Guys are so predictable. I feel rather smug knowing my nipples are super perky right now, and in spite of myself, my freshly waxed pussy is creaming a little bit just imagining what he's taking in with his eyes. I'd bet his eyes would pop right out of his head if he could see my bald snatch and ass.

Finally, he swims back to his end, and I take the occasion to raise myself up to semi-recline on the chaise. I put my huge sun hat on my head but don't put on my sunglasses back on, the sun now well on the wane. Once he reaches the other end of the pool, he gets out by pressing his hands on the concrete edge and pushing up. His entire body flexes for a moment, and I must say, he looked pretty good. He seems older, definitely older than my 37, but aside from a little telltale softness above his waistband, he is in excellent shape which makes sense considering his expert swim strokes.

I've been celibate for six months now, if you consider copious masturbation with a menagerie of sex toys and penning salacious erotica being celibate. My last relationship and breakup was pretty tragic, after which I decided to stay on my own a while. It's also been good for the writing. There's something to be said for abstinence stirring the creative juices, so to speak. Hence the current state of affairs is I'm always a little bit horny but have no real desire to hook up. I make pretty good love to myself and am content with the way things are, for now.

On the other hand, I do have a thing for hot older guys, my last guy being both older and hot. Just unfortunately a womanizing fuck-up. I'm pretty open-minded and not 100% monogamy-minded; just don't fucking lie to me. Anyway, hot older guys... lying here in the warm Barbadian late afternoon, I find my mind wandering to various scenarios, utilizing the model in closest proximity, the older fit guy coming out of the pool.

Maybe I could get him to help me apply sunscreen to that hard-to-reach spot in the middle of my back, which might expand to my entire back because why not, and his hands would linger because that's what guys do. Then maybe he would nuzzle his face in the crook of my neck where I'm so sensitive as his hands wander to my front under the guise of applying sunscreen between my A-cups and his fingers would slip under the edges of the fabric triangles because, hey, you can burn along those edges if you're not careful.

But his fingers are long so they graze my nipples, as if by accident. And then the hands linger and palpate my breasts and lightly pinch my nipples and he'd say, "Mmmmmm, pretty breasts. Do you mind if I lick them?"

To which I don't reply and only turn on my chaise and hook one arm around his neck as he unties the string behind my back. I offer my white tits with their tan lines to his half-opened mouth and watch as he takes his moistened tongue out of his mouth and envelopes one dark nipple with tongue and lips to lightly suck on them, then the other, then back and forth between the two.

As he does this, his hand unties the string behind my neck and whisks the tiny strips of fabric away, and then he slips his hand inside the front of my bikini bottom and his middle finger lands at the top cleft of my camel toe. Still loving on my tits, he slides his hand down further and discovers my pussy is completely smooth and I can hear him groan softly in the back of his throat as he sucks a little harder on my sensitive tits. He moves his hand more firmly down my mound, shifting the bikini bottom lower on my hips as his other hand pushes it down the back.

The middle finger of his front hand is at the entrance of my inner pussy lips now which are slightly gummed together from having been encased in the snug bikini. He lightly strokes and coaxes the lips apart and discovers the puddle just inside the mouth of my vagina, making him grunt again. He takes his head off my nipple and moves up to finally kiss me deeply. His tongue plunges into my mouth at the same time he dips two knuckles of his middle finger into my creaming pussy. I, in turn, moan deeply into his mouth as I suck on his tongue.

His finger now gooey with my juices, he slowly takes it out and strokes my clit. He goes back and forth between my wet snatch and my nubbin many times with his finger as he continues to kiss my mouth, neck, throat. Fuck, he is good with his hands. That's one great thing about older men. Never in a huge hurry.

By now, I'm lying on my side on the chaise. He pauses to draw my bikini past my hips and off my body so now I'm completely naked outside next to a complete stranger whose name I don't even know on a Caribbean island. He rolls up the fluffy towel into a makeshift bolster and tucks it between my bent knees, so that I'm still on my side with my smooth snatch and ass completely exposed to his gaze and open to his hands.

He resumes the play on my pussy and my clit with the front hand, while his other hand strokes my pucker. Oh my god, I love ass play. This is my downfall. For a guy who makes love to my ass the right way, I would willingly break my celibacy.

With his hand in back, he is now wetting his thumb tip in my pussy as well and inserting the first knuckle of his thumb into my anal ring, and eventually up to the second knuckle. I am a writhing, moaning mess and am literally putty in his hands. I had already been rubbing my nipples and am now tweaking them even harder.

He is speeding up the cadence of his movements, coordinating his front hand with his back hand, or his back hand with his front hand perfectly, relubing with my pussy cream as needed. It's uncommon that I orgasm from manual stimulation, but this guy has got it going on! I'm bucking my hips rhythmically back and forth on his talented fingers as I roughly squeeze and twist my nipples.

"Oh my god, you're gonna make me cum. Your hands are amazing... "

"Yes, cum for me, cum in my hands, baby."

I hate it when guys call me 'baby,' but it suits this older playboy in this setting and turns me on immensely. "Oh my god... Oh, fuccckkkk, I'm gonna cum hard. Work your thumb faster in my ass!"

He does so as he focuses the finger pads of his front hand on my clit, bringing me to a teeth-gritting climax and plunging the thumb of that hand into my sopping pussy right as I'm coming. I reach back to connect my hand to his and keep his thumb in place in my ass, my other hand on top of his hand on my front mound. I can feel my ass ring convulse around his fat thumb which feels like a sweet little cock, and my pussy is creaming so much, my inner thighs are completely slick. Amazing.

Mmmmm, I'll have to incorporate that into my next story. See? Abstinence stokes creativity. I think I'll go in and type it up.

+ + +

HIM:

After about 15 minutes on her back, my mysterious neighbor gathers her things and gets up to go back to her unit. She flicks me another a little wave, which I return. I enjoy watching her walk away. Her ass is very nice indeed, and between her perky tits and her long-limbed cat-like gait, my cock is threatening to rear up again. It's fun to have some eye candy nearby even if I have no plans to hook up. I'm old enough to know that rebound sex is not a great idea. But my temporary housemate will provide fresh fodder for a future wank session, for sure.

I stay a little while longer and finish my beer then go inside. I take a long shower, lazily fondling my cock while foaming up with the body wash, my mind going over the images of the afternoon. As usual, I don't bring myself to a full orgasm. Keeping it nice and easy. Low simmer.

That evening I drive over to Bathsheba and have a nice dinner solo. I do wonder what my neighbor is doing. Does she have friends here? Is she cooking for herself? Or is she also at a restaurant by herself? It would be a crime for a good-looking woman to dine by herself. I mean, I presume she's good-looking, I've only a few body parts and observed her walking away from me, and that all looked pretty good.

The next morning, I rise early and go for a walk to the beach and back. It's not far, about 15 minutes each way, but by the time I'm back at 8am, it's already quite warm. I had trunks on already and without even going inside, I pass through the little side gate to access the pool. As I'm pulling the gate to behind me, I can just see my neighbor rinsing off in the outdoor shower that each of our units has. She is completely naked, of course, her front turned towards me, suds coursing down her glossy body.

Reflexively I take a step back to duck out of view, but my eyes already took in her full nakedness: Her head leaning slightly back with her eyes closed as she's rinsing the shampoo out of her hair, her hands massaging her scalp so that her pretty tits framed by the bikini tan line are uplifted, her slim sun-kissed legs, and most enticing, her bald pussy mound, the fair skin tone set off by the tanned belly and thighs. Fuck, she's hot. As an old Gen X'er, I still love a trim muff on a woman, but bare is very hot, especially for licking. And of course, rimming a slick backside is beyond compare.

Plus, she's a total fox. Dark hair dipping past her shoulders, her facial features well-defined, full lips. My cock is already half hard. I'm going to have to go back through the front door and take a cold shower. What a sight, but I almost wish I hadn't glimpsed her like that. If I ever actually meet her, it will be hard to forget what I had seen.

[End of Part I.]