As told in an earlier story, my husband, Jeremy, and I were on our Jamaican getaway at a glorious clothing optional beach resort. We had intended to spend two relaxing weeks on the nude beaches (sans bathing suits, of course) and wandering through the shops in town. Unfortunately the first week had turned into Jeremy basically locked in the hotel room dealing with work issues, which left me at the hotel pool – naked – and without Jeremy to pay attention to me.
Fortunately for me, a local hotel worker, Toby, had taken his breaks by the pool, and had proven to be very attentive, with a big black cock, and totally nude. On the first day I saw him, he had approached me on my chaise lounge and introduced himself, with his hands on his hips, a big smile on his lips, and a massive prick dangling between his legs, just inches from my face. Before long I was stroking his shaft and sucking on the head of his dick. He fucked me right there on the chaise lounge while two other couples sat on the other side of the pool watching. One couple fucked, with the woman riding her husband’s cock in reverse cowgirl, while staring intently at Toby’s impressive cock. The other woman was also mesmerized by his hug rod, and jerked her husband off with one hand, while rubbing her clit with the other, her eyes never leaving Toby’s beautiful, back dick, as it pounded my pussy mercilessly.
Anyway, Toby made me cum several times that first day, then left to take a shower before returning to work at the hotel. I exchanged smiles and waves with the other wives as I left the pool that day. Since Jeremy was tied up for a few more days, this became a daily routine for Toby and me. We’d meet by the pool (no bathing suits, of course), I’d admire and stroke his cock for a few minutes, then suck it until it reached its fully erect 12 inches. Then he’d plow my pussy until I climaxed several times, and he emptied his nut sack deep inside my dripping wet cunt.
My husband knew about Toby. He enjoyed watching me get fucked by other men, and if he couldn’t watch, he liked to hear about it. So every evening over dinner, I’d tell him about my afternoon fucks with Toby while I stroked his cock under the table at the hotel restaurant. Then we’d quickly head back up to our room, where he’d fuck my brains out over and over, as I relayed all the details of Toby’s big black cock pounding my eager pussy, and Toby blasting loads of cum deep into my cunt.
On the fifth day, Jeremy finally finished working, and we were able to head out to the beach behind our resort for some relaxation. The beach was also clothing optional, so we were both completely nude as we lay on our big beach blankets enjoying the sand, surf and sun. I occasionally looked around us and noticed that virtually all the couples on this beach were nude, and many were in varying stages of sex…..many handjobs and blowjobs were underway around us. Some were even fucking. I couldn’t help but watch a few of them, and it was making me horny as shit.
I also noticed that there were waiters and waitresses – also completely nude – moving from towel to towel, taking orders and returning with drinks on a tray. Occasionally I’d see a guest stroke or massage a waiter’s cock, or squeeze a waitress’ boob, which sort of surprised me. But it also made me even hornier, and my pussy was getting seriously moist.
Jeremy was on his towel right next to mine, and I was casually stroking his semi-hard cock as he read a book, and I observed everything going on around me. As we lay there like this, a waiter approached me, squatted down next to me and asked if we’d like anything. As he squatted by my towel, with his knees spread, I couldn’t help but notice that he had a very long, and impressive cock. It reached almost to the sand between his legs, and it swayed back and forth like a pendulum as he waited for my response. Without even thinking about it, I spread my legs slightly, and reached my left hand out to gently stroke his dangling shaft. He noticed my spread legs, and gave me a toothy smile, as he moaned a little in response to my fondling his prick.
I ordered a chunky monkey, which is a chocolaty blended drink made with rum, then looked to my husband to see what he wanted to order. He was smiling at my spread legs, and my hand toying with the waiter’s black rod, then ordered a cuba libre, which is essentially a rum and coke with lime. The waiter said, “No problem” and, reluctantly, left us to retrieve our drinks.
Jeremy and I exchanged glances and smiles, and I knew what I was going to do when the waiter returned. Sure enough, the waiter came back with our drinks about 10 minutes later, and squatted in the same spot as before. He took my husband’s drink from his tray, and leaned over me to hand it to Jeremy. When he did, I again reached for his dick and began stroking it as it wobbled between his legs. He shifted forward from his squatting position onto his knees, which gave me a better angle for gripping and pumping his dick. He knelt there, balancing my drink on his tray with one hand, while he fondled my breasts with the other, and moaning as I worked my hand up and down his shaft. Meanwhile, as I pumped his cock with one hand, I had moved my other hand down between my spread legs and was rubbing my clit and slipping my fingers into my dripping wet pussy.
I glanced over at Jeremy, and was not surprised to see him lying on his back, watching me whack off the waiter, while wanking his own rock hard prick with his fist. As I watched Jeremy pounding his pud, a pretty black waitress squatted down next to him, and offered to help him out. In her squat position, with her knees spread wide, we could both see her beautiful red pussy lips poking out between her legs. Jeremy eagerly accepted her offer, and she took over stroking his stiff erection, as he began squeezing her beautiful tits and pinching her nipples.
I returned my gaze to the majestic prick I was jerking, and almost immediately I could feel myself building up to a massive orgasm. With a little squeal, I launched into an electrifying climax that made my whole body shake. I kept pumping the waiter’s big black cock, and before long, he blasted a huge load of cum all over my stomach, never dropping a single drop of my chunky monkey drink on his tray.
I heard a grunt from Jeremy, and I looked over just in time to see him shoot a massive load of cum about 2 feet into the air, as the waitress continued to pump her fist up and down his shaft. She slowed down her strokes as his big dick began to soften, then smiled at him and released his now flaccid dick. She let him have one final squeeze of her boob, then stood up and carried on with her other customers.
I was still slowly jerking the waiter’s beautiful ebony cock, trying to pull out every last drop of cum from his ball sack. I finally finished, leaned up and sucked off the last drop of cum from the tip of his dick, then gave it a little peck and released it from my grip. He smiled at me, handed me my drink, and stood up….his softening prick still glistening from his cum and dangling between his legs. Then he was off to serve his other customers, his long shaft and nut sack swinging back and forth as he walked away.
Jeremy and I looked at each other and smiled. Then we cleaned all the cum off of our stomachs, and – with drinks in hand – went back to what we were doing before. I thought to myself with a smile, “Eight more days of this before our Jamaican vacation is over…….not bad.”