A long, long time ago, in a land…. well, it WAS a while ago, but things like this stick in your mind.
I was about twenty-three, in the Navy and stationed at a base right next to one of the premiere resort cities of the Caribbean. It was long before AIDS and all the other little “nasties” became so dauntingly prevalent, and I was – as usual – on the town and at the casinos, my regular Friday visit spots when I didn’t “catch the duty” or if some poor schnook would stand it for me.
I was a lucky player and usually could support my champagne tastes on the winnings…. God alone knows the “Big Eagle” shit very thinly in those days, and without my “luck” I’d have been condemned to the “shot and beer” scene at the local bordellos. Eccchh.
This nite I was playing craps, when a lovely young woman squeezed in next to me at the table. I was used to being hit on by single women and thought that this would be yet another interesting evening.
She stood by me for a few minutes and contrived to nudge her breast into my arm several times, all the while flirting with her dark and exceptionally beautiful eyes. I reciprocated and, having won enough to fund the next month-or-so’s lifestyle, turned to her and asked if I could buy her a drink. She seemed pleased to accept, but said, “I’m not alone here. My husband is with me.”
I was a bit non-plussed, to say the least, but sensing my confusion, she hurried on, “He’s been watching us ever since we spotted you. He likes it when I find someone whom I think attractive enough to try to pick up.”
Involuntarily, my head came up and scanned about, seeking a perceived source of threat, but I found a remarkably handsome and quite dapper gentleman of about fifty, with a fine Imperial goatee (of all things!) and a full head of matching silver and charcoal hair. The way he was smiling immediately dispelled any sense of threat I may have had and this was reinforced by the warm handclasp he offered me.
I was now totally bemused by the situation and sought refuge (of course, towing these two with me) in the bar. Actually, I sought a large Glenfyddich, followed by it’s sister and cousin.
The woman, Elisa, and her husband, Andres, were from another of the Islands and in town on business. She was about twenty-six and, while not ostentatious in any particular, was so pleasingly formed as to immediately be “The Woman We Love To Hate” for any other female in the immediate vicinity. Andres was, as I said, fifty (ish) but was as trimly made as someone his wife’s age. She, about 5′ 3″, he about my own 5′ 11″. She a lovely shade of Caribbean honey-gold-brown, with long black ringlets, coral lips and whiter-than-white teeth. He was probably of French decent, slender (about 170 to my 200 pounds) and dressed like a gentleman of “the old school” of Paris.
We all had a more leisurely drink while, like a Greek chorus, they explained that Elisa was a connoisseur of males and whenever they were away from home and fairly anonymous, they loved allowing her to exercise her gourmeterie (which once in a while became gourmanderie) when the opportunity arose.
It appeared that the opportunity had, indeed, arisen (as had I by this time) when she saw me and so….. The only thing they thought I might have a problem with was that Andres would like to also join in the affaire, and did I think I could handle that?
By this time, Elisa was leaning toward me, the scoop of her shell revealing that she needed no brassiere to hold that exquisite pair of breasts, with her hand upon my thigh, affecting an intense concentration but effecting a raging hard-on for me.
I’d never had any sort of experience with this sort of thing, but another Scotch certainly dulled any hesitation I might have had, and so, after a bit of rubbie-dubbie with kissie-mouth, the lady stood and we, like good little puppies, followed her to their rooms in the hotel. I think we scandalized the help a bit (I didn’t think it was possible at the El Convento), as we took the grand staircase up (only one flight, damn it) and both Andres and I were rather overt with Elisa on the way up.
Once we got to the rooms, Eliza flounced over to the stereo (no cd’s back then…. hell, we were lucky to have Stereo!) and plopped on something moody and blue, proceeding to sway about the room, while Andres made me another drink (!) which for some reason really didn’t seem to be affecting me. Eliza danced over to where I sat and began shedding diaphanous pieces of rainment…. the bodice went first, followed by the skirts, leaving her in a filmy chemise which whirled about her thighs, contrasting with the Creme-da-cacao colour of her skin. She’d sway and swirl to the music, sometimes raising her hem to wriggle, and I struggled out of the chair and began to dance with her.
Andres came over and we formed a triad, dancing in quiet time to the music,while I ran my had over Elisa’s breasts and down along her side to her hip. She faced me a little more and I slipped my hand under the chemise to find no panties and a very sparsely-curled pubic thatch, which was as wet as a sponge. I stroked her belly and then ran my hand back to her cunt, only to find Andres’ hand there before me.
Elisa was beginning to have a problem keeping her feet, so, with a glance at Andres, I swept her up and carried her into the bedroom, kissing her breasts through the chemise as I did so. I placed her on the bed and, as I let her settle back, stripped the chemise from her, leaving her clad only in thigh-top stockings and her shoes.
Andres indicated I should sit on her right side as he took the left, and we proceeded to kiss her neck and breasts while first one, then the other of us would stroke her cunt and lips, occasionally dipping into her deeply with a finger. Her nipples were long and a light brown, and as hard as drill-tips. A sheen formed on each one and as I kissed it, it leaked into my mouth a bit, which excited me intensely. Andres slid his hand up under her and began to stroke her ass-pucker, using the copious vaginal secretions flowing from Elisa as lubrication. The next time I put a finger into her, I felt Andres finger through the thin membrane separating our flesh.
Elisa went ballistic. Her hips came off the bed as though launched and she turned to stone for a few seconds as her orgasm hit, then flopped bonelessly down and began to shake and shudder in it’s throes. Andres and I just remained in place until she was almost done, then withdrew from her body together, which sent another orgasmic shock through her.
Elisa was obviously a wipeout for a moment, so Andres, after surveying (with justifiable pride) the “spoils” of our endeavours, asked If I’d like to get out of my clothes while he got our drinks from the other room. I disrobed quickly and stretched out beside Elisa while she recovered her breathing.
She rolled toward me and proceeded to kiss my face a hundred times, all the while seeking and finding my rampant 7 inches with her lily-soft hands. She broke from my face and pushed me over on my back, trailing down my chest and stomach with little nips and kisses until she could engulf my cock with her mouth, her black ringlets allowing me only a glimpse of the sensations I was experiencing.
No matter, she swirled around the head of my cock and then simply dropped her mouth onto me until I was buried in her throat, then had only the head in her teeth and then buried me again…. I just shot off like a cannon. She squirmed and slapped her cunt across my leg as I unloaded into her mouth and throat, then she came off me as she orgasmed again and I shot my last cum on her face and breasts. Andres had also stripped out by now and knelt on the bed behind Elisa, supporting her as she continued to orgasm and then gently laying her down beside me. He immediately lowered his head to her pussy and began to lick up all the wonderful juices she’d been emitting, paying special attention to her ass and clit. Elisa was rolling about on the bed, making is hard for Andres to stay connected, but experience will tell, and she never managed to shake him free until yet another stiffening and collapse told us she had spent again.
By this time, I was like a granite monument again and, tapping Andres on the shoulder, I rolled so that I covered Elisa in the missionary position, scooped her thighs up with my hands and just penetrated her to the full. My cock hit bottom on her cervix and she convulsed as though shot. I thought at first I had been too rough, but her legs scissored around my back and her arms clutched at my head and neck as she tried to force more of me into her. I obliged but getting my knees a bit more under us and really ramming my cock into her as hard as I thought she could take. We kept this up for several moments until she once again stiffened and drooped, while making the most amazing cross between a cry and a purr deep in her chest.
It was then I felt Andres kneel on the bed behind me and suddenly felt his head pushing between my thighs. He began licking us where we were joined, licking Elisa’s asshole, then coming back and licking the bottom of my cock when I drew back and my balls when I thrust forward. I was in Heaven. I never thought that sex, as wonderful as I knew it to be, could EVER be this good!.
Andres began to neglect Elisa for me, licking and sucking my sac and moving around to the rear, stroking and then licking my (’till then, Virgin) pucker. The sensations were astounding. I’d never felt such a hot, wet, sensual sensation such as that before, and I leaned forward and moved my knees up to allow freer access. Andres pulled his head out and began to lick my asshole with abandon, reaching under and cupping my balls and shaft with his hand.
Elisa, feeling what was going on, slowed and then stopped, allowing me to fall out of her and then quickly swung around under me so she could suck me while I was presented with her freshly-fucked and wide open cunt.
I fell forward on her body as she took me dick into her throat and began to lick and nip at her labia and clitoris as Andres still licked and fingered me. He evidently had some lubricant close to hand because I suddenly felt something cool on me and them his finger began a slow insertion into my rectum. Elisa also ran her hand up alongside Andres’ and when he withdrew, she joined their finger for a double penetration of my asshole, which just drove me more deeply into Elisa’s cunt.
Elisa then scooted out from under me and knelt on the bed in front of me, asking if I’d fuck her “doggy-style”. Suiting action to intent, she wiggled back until my cock was touching the folds of her distended cunt, and I proceeded to fill her from that direction.
Andres held my hips and lifted me so I could have an optimum angle for penetration and lightly “urged” my rhythm in Elisa. Then I felt it. Andres cock was moving around on my ass. Here was the moment of truth, when I had to decide if I was going to dooooooo….. Too late.
Andres’ cock slowly opened my ass and began to penetrate it, and I LOVED it. It was so damn hot and hard, and this was so Hot and Nasty, I swear I grew an inch in Elisa.
Andres’ cock kept slipping into me – it felt a foot long! – and it was getting even better than at first, then he withdrew all but the tip and I felt empty and hollow. I actually moved my hips back to recapture that shaft, but Andres was already coming back. The satiny feel of his cock slipping into and out of my asshole was indescribably wonderful…. It was all sex, bottled up and dispensed and once huge dollop, it was like nothing I could ever describe in words, but the sensation was mind-boggling. Andres kept a nice slow stroke in me and I just allowed his motions to govern my motion in Elisa while I pinched and pulled at her nipples.
Finally, Elisa did it again, but it was rather more spectacular for being so deeply inside her when she came. I felt the muscles in her abdomen tense and lock and then the muscular contractions hit her vagina and milked the length of my cock like a Vaseline -covered fist. At the same time, Andres sped up and I could feel his erection getting larger and harder, until he suddenly let go a stream of heat deep inside me that was so electrifying I began to shoot into Elisa as though I’d never come earlier.
We all clung to one another as we shuddered through our orgasms then, as one person, we all collapsed onto the bed in various poses of experienced rapture.
A time passed in which we all just lay there and recovered ourselves. One thing I couldn’t recover, though, was the fact that I’d just been fucked by a man, and that I loved it. That cherry was gone and I wasn’t sure how I felt about that. I wasn’t sure until Andres’ hand encircled my cock and Elisa’s mouth began to work her magic on me again. By the time Elisa came up and began kissing me while another mouth began sucking me, I was pretty sure that I wasn’t gonna miss that particular cherry very much.
Elisa kept kissing me and then moving up a bit so she could hold my head up to her breasts, which had started dripping a little bit. I fastened to one nipple like a starving infant and, like that infant, was rewarded with a hot, thin spray of milk from her breast. Andres said he knew the instant it happened because my dick got stiff as a board and I thrust up into his mouth with some force. I continued nursing on Elisa’s breasts but suddenly my cock was cold and untended for a moment. Not long, as Andres slowly squatted himself down onto my dick, which then said goodbye to another cherry as it penetrated up into Andres’ bowels.
Ass-fucking a woman is a wonderful thing, and if you find a lady who favours it, consider yourself fortunate. Ass-fucking a man is a totally different feeling… his balls slap your abdomen, his asshole is tighter and harder and the internal plumbing is such that a completely different series of obstructions confront the aspirant penetrator.
Worth it, though.
Elisa had swung around to rest against the headboard and to support my back and head on her abdomen and between her breasts. She stroked my chest and could just reach down to Andres’ cock, which I now saw was at least 8″ long, with a fat head and thinner shaft than mine. He leaned forward until he could put his hands on Elisa’s shoulders and kiss her deeply, all the while moving himself up and down on my cock. The sensations were so incredible that when Elisa suddenly pushed against my shoulders, curling me towards Andres’ abdomen, I simply opened my mouth and took the head of his cock into is whenever it was close enough. It was coated with cum and pre-cum and tasted just super to me, but it was tantalizingly out of reach most of the time as was yet a third cherry for the night!
I decided, in for a penny, and pushed Andres off me and onto his back. Getting to my knees in front of him, I picked up his thighs as I had done his wife’s earlier, and slid my length into his ass in one smooth motion. He arched his back and found Elisa’s cunt coming down on his face for some attention. Burying his face into her, and with my cock deeply in him, I saw that if I leaned over I would have something within range, and so bent as far as I could and sucked him deeply into my mouth.
Too much, again! Andres stiffened and let out a muffled cry as his cum spurted up into my mouth at the same time I began to spurt into his ass… it were as though we were one great electrical circuit as Elisa also began coming again.
This time, when we collapsed, it was for good for the night. I awoke some hours later with a sensation of having taken the world’s largest shit and still being open back there, while my body was entangled with various delightful portions of two other people. I went back to sleep.
The sun found us all cuddled spoon-fashion together as though we’d been at this for centuries. We all acted as though this was our norm, also, waking, kissing, cuddling and stroking like experienced lovers. We took showers, repeated the evening’s entertainments in several variations and generally enjoyed the morning. Especially nice was when I was fucking Elisa with her atop me and Andres slid his dick up her asshole. I could feel the entire length of his cock as it moved past mine and we all three came as one again, Elisa’s muscles milking the cum out of both of us at once. Glorious fucking!
I borrowed a shirt and trousers from Andres while I returned to base, reported my whereabouts and the fact that I’d be back for muster on Monday, “Don’t bother looking for me until then”, got a change of clothes and the other tux and hightailed it back to the hotel….. only to find that Andres and Elisa had checked out while I was gone.
I’d forgotten anonymity was their watchword and, for a while, I felt terribly used, but then I realized that while we’d all used each other and the results had been fabulous, the results were really due to the novelty of it (for me) and the intensity wasn’t something that could be sustained. Wise people that they were, they knew from experience (I hope not bitter!) that such encounters were best left to a single experience, lest the emotions become jaded after a while.
In all, I spent four and a half years on that Island, had many sexual adventures there and other places in the Caribbean and generally lived the life of a roue-in training (and was quite good at it, thank you) but I never had another encounter of such intensity again. I instigated several other threesomes and, while they were intense in their own ways, then never quite hit that peak of orgasmic energy that I had discovered that night.