Here's another of my stories. I've had a fantasy of living in a sexual paradise in Florida and here is the first of that series. It is entirely fictional.
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A Friend from Connecticut by James Wilton jimofct@gmail.com
Money may not buy happiness but it sure lets you have lots of fun. And, don't I know it. At the age of forty I managed to win the New York State Lottery and give myself a very comfortable early retirement. I moved here to Florida and live in a sprawling house that wraps around a pool. I have a housekeeper and caretaker for tending to my basic needs and I only have to cook or garden if I want to. I have also managed to collect hangers-on to take care of my sexual needs.
This place has seen a parade of two or three handsome young men at a time who live here for a few months and then move on. They flop in one of my guest rooms, loll around the pool, and have open use of my kitchen and bar. We occasionally take shopping trips to keep them attractively dressed, on my plastic, of course. And, someone periodically slips fifty-dollar bills into their dresser drawers. My only expectation is that they are always receptive to my urges. Knowing what a good deal they have, they are usually more than attentive to my friends, as well. It's nice.
One week, a particularly handsome and horny friend named Dan came down from Connecticut to escape the February cold. He's in his early forties, blond, big-boned, and thick-necked; a real football player type. At the time of his visit I had Jack, Greg, and Larry keeping me company but I hadn't told Dan about them or my general situation.
On his first morning, Dan got up early, still being on hypertime, I guess. We sat clad in poolwear, eating breakfast and enjoying coffee by the pool when the first of the boys showed up. Dan's eyes bugged out at this cute youngster plopping down on my patio. Before long, numbers two and three joined the circle. Dan was obviously enjoying the scenery but was too polite to ask me "what's the fuckin' story?" The three boys were groggy, in their morning fog, and were only partially aware of the attention Dan was giving them. They were dressed only in their Speedos and, without doubt, Dan was enjoying the delicious view of three young men exposing almost all of their attributes.
When my guest went inside to use the bathroom, Greg asked who that was sitting by "their" pool. When I told them it was a friend from the North they asked if he was fair game. Upon hearing that he was, Greg began whispering with the other boys and I suspected that Dan was in for an interesting morning.
Upon his return poolside, his excitement was about to be significantly increased. Each of the boys pretended to be dosing. Jack lay on his stomach and began to very slowly grind out an erotic humping of the inflatable raft. Greg lay on his back with his legs spread and ran his right hand over his chest and stomach, absentmindedly. The gently brushing of his nipples and the idea of what he was doing to our guest caused his bathing suit to fill and eventually tent up. Larry was probably the sexiest of the three. He lay face up on the patio with his hands behind his head and his legs spread wide with Dan facing right up that arousing vee. He didn't move or touch himself in any way yet his dick rose up in his pouch and worked the head out of the elastic until it was fully visible to any lookers. Meanwhile, Larry acted oblivious to the rest of us.
Dan couldn't miss the sexual heat displayed before him. He began to squirm and adjust himself shyly. Soon he realized the ridiculousness of his modesty and arranged his growing erection so it could rise with a minimum of discomfort, decorum be damned. He ogled one and then the next of the boys. Without saying anything he looked over to me for an explanation but I wasn't going to let him off the hook that easily. I played dumb to the whole show but did let on that I was enjoying it, too. My own growing woody would have made any attempt at indifference an obvious lie.
Finally I broke the silent tension by asking Dan how he liked the boys who were staying at my place. With a crack in his voice he said the thought they were real cute. At this, Greg slipped his hand down lower than before and rubbed it back and forth along the length of his erection. Jack peaked out of his closed eyes at Greg to see what the stirring was all about. Larry, though, did not break his demeanor and really seemed to be asleep, though having an erotic dream.
Exchanging a wink, the two boys got up and approached Dan. One stood on each side and pressed their aroused baskets against his sizable biceps while they ran their hands down his chest, causing his nipples to rise in excitement. Dan sat enjoying the stimulation while he watched the glory of the hot vista at his feet. He reached his hands up between the legs of the two boys and grabbed their asses, pressing them harder into his shoulders. In reply, they leaned down and began nibbling at his neck and ears. This was turning into a midmorning orgy. Dan became so turned on to the work on his neck that he began to ignore the view before him and rocked his head from side to side as the boys turned up his sexual heat. As if on signal, the two of them reached down beyond his waist and massaged the tubular basket that held his dick. At first they worked the member through the fabric but soon their hands were inside the cloth and were manipulating his cock and balls. This drew serious moans from Dan as he arched his back and pushed his erection up into the hands playing with it.
Without any of the three of them noticing it, Larry had figured that the sleeping ruse was up and he was missing some action. He crawled the short distance from his spot on the concrete to between Dan's legs where he began licking the thighs from knee to crotch. This had the obvious effect of furthering this man's excitement. As the other two began to uncover Dan's equipment, Larry was there to lick the newly exposed genitalia. First, he performed the needed task of laving the precum off the head of Dan's dick. Next he licked the length of his shaft, to the delighted response of my guest. Finally, as the entire package was exposed, he treated the balls to an oral massage, leaving the pulsating erection to Greg and Jack's attention.
At this point, Dan stood up and called an end to the proceedings. He announced that he was too close to cumming and wanted to wait until later to spill his seed. At our age, the excitement can be phenomenal but there is a limit to the number of ejaculations in a day. He pulled up his trunks, dashed across the patio, and dove into the pool, followed by the three boys. They weren't about to give up on this hot man even though he had managed to cool down his equipment. They cornered him in the deep end and pecked at all parts of his body like feeding guppies. This foolishness got him laughing and the tension of the morning was broken. The five of us turned the episode into a splash and dunk fest.
After lunch, Dan got me aside and worked out the lay of the land. He wanted my permission, freely given, to dally with any or all of the boys. So, when we returned to poolside, I had the three line up and gave Dan his choice for a companion during his siesta. He took over and had them pull down their bathing suits and work up an erection.
First there was Jack, a tall, slim, brown-haired boy with smooth skin. He was the cutest of the three; a real boyish look to him. His cock was long and thin, to match his build. His balls hung real low in a nice, silky sack. Greg was the shortest of the three. He had that Latin, seductive look about him. He was also the darkest and the only one with much hair on this body. He had the classic triangular body with broad shoulders and narrow hips. His dick was quite big and curved noticeable upwards. Last was Larry. He was medium in height and also smooth. His dark blonde hair was cut very short and his heavy beard always looked like he needed to shave. He had a broad jaw and a dimple in his chin. His body was like a hockey player's. He had broad shoulders, big arms, a barrel chest, big buns and powerful thighs. His dick was not as long as Jack's but was the thickest of the three.
Dan enjoyed handling the three of them. Their bodies were all hard and well defined so the testing was as good as the selection. All three of them had nice hard ons and my friend pulled each of them down and released them to snap back up to the hard stomach above. The boys were thoroughly enjoying the event. They were exhibitionists to begin with and they were also getting turned on by watching this hunk enjoy himself so much.
The final choice was Larry. Jack, Greg, and I lay back on our lounges as Dan proceeded with his matinee. Later on, he told me all about it: He wanted to get fucked and took Larry because his thighs promised a power fuck and his thick dick would fill him up without punching in too deep. His instincts had been right because Larry truly was a fuck machine.
After the preliminaries, Dan had the boy grease up his hole and then he sat on the dick. This gave him the chance to ease down on it and open himself gradually before the real assault began. Once Dan was comfortable with the equipment, they rolled into a doggy fuck. Dan said that Larry rammed him so forcefully that they actually moved across the bed. Finally, they changed to a classic missionary position where Dan could enjoy the hunk's body above him. He felt his way over the huge chest and caused extra hard jabs with each tweak on those erect nipples. He said he especially liked looking up into that sexy face as it was contorted with the agony of sexual arousal. As he sensed the stud above him approaching climax, Dan reached down to his own hard erection and brought himself to ejaculation just as he felt the dick up his ass filling its condom with jism. After that came the real siesta and the two of them finally reappeared late in the afternoon.
Cocktails and dinner were times for Jack and Greg to openly flirt with Dan and try to be the next to win his affections. Neither of them was very subtle and Dan didn't mind a bit. He was eating up the attention. By bedtime, which was unreasonably early since the three of them were so horny, Dan couldn't decide on a bedmate so he took both of them. That left me with studly Larry.
After his experience with my northern friend, I didn't want him too self-impressed so I took the mega-top role. I had been turned on several times during the day but had not yet gotten my nuts off and I was ready for some heavy action. Once we were in my bedroom I had Larry remove his Speedos and kneel at my feet with his hands behind his ass - my boys know this as the submissive pose. As soon as my order was given I saw Larry's cock jump and begin its hardening. He knew what was ahead and it obviously excited him. Without using his hands, I had the big boy mouth my dick through the shorts and get me even more turned on. Next, I had him lower my shorts using only his mouth. As my jockeys were pulled down my thighs Larry was hit in the face by my very aroused dick. This got him even more into the action and he went for the spot he knew would turn me on: my balls. After a long tongue-massage, he worked his way up the length of my erection and eventually gave me the blowjob I had expected.
Being near to an explosion, I had him stop pretty quickly. While I got a condom, I had Larry kneel in the supersubmissive pose; face and shoulders on the floor, ass in the air, and hands spreading the cheeks for easy viewing or access to the rectum. I got quite a bit of pleasure out of seeing this little toughie presenting himself so meekly to me but, my cock wouldn't let me savor the view for long and I soon mounted him. In spite of his top demeanor, Larry did enjoy bottoming, too. As I inched my way into his tight anus, he moaned and gasped in pleasure. When I finally hit bottom he bounced back against me as if to force that extra millimeter into his hole. As I fell into a steady rhythm of fucking I reached around and felt his hard fire plug jutting out from his belly. I could barely grasp its circumference but its size was truly a turn-on. While I humped his ass, I jacked that hot piece of manmeat. The nearer I got, the nearer I sensed he was. Finally, I arched back and rammed myself as deep and as hard as I could while I blew out my seed and I felt his erection stiffen even more and blast his cum over my fist and the floor. Without wanting to dismount, I collapsed over this broad back and let my dick slowly shrink in its warm crevice. Eventually it was ejected my Larry's strong ass muscles. Both of us were sorry the coupling was over and we rolled onto our sides in a long back-to-front embrace.
The next morning, Dan told me that his experience had been totally top, too. Both boys had such enticing asses that he couldn't decide between them so he became a pig and used both boys in turn. At first he had both of them kneeling on the edge of his bed, presenting their asses to him. He played with both at once and the two of them competed for the more satisfied reaction. At this point he decided to sample each. He had Greg lubricate Jack's slim ass as he sheafed his own cock. Then, as he mounted the taller boy, he had Greg climb under him and suck his cock to keep him aroused. This was no burden for our dark friend who was an inveterate oralist. Before things climaxed, Dan chose to reverse their roles and had Jack sucking that dark, big dick as Greg got his ass plowed. This time things did not end prematurely and my friend shot his load inside Greg's ass, sending the dark boy over the top as he sprayed Jack's face with his love juice.
Once they recovered from the intensity of their eruptions, Dan realized that Jack was still erect and ready to blow. Wanting to watch a rut, he had Greg roll onto his back and throw his legs up for Jack to enter him. Dan took hold of Jack's throbbing cock and guided it into Greg's recently used entrance. Things were loosened and lubed for that long, slim tool and it gently slid its full length to the bottom of Greg's love pit. With direction from this finger tips against Jack's thighs, Dan was able to choreograph an ever intensifying mating. Quickly he had a powerful rhythm going as Jack's long, thin dick drove deeply into Greg. At the bottom of each thrust, Jack's lowhangers bounced off Greg's tailbone. As the end approached, Dan reached between Jack's thighs and felt the root of the boy's dick as it pulsed out the staccato of an ejaculation. After such an intense session, all three of them slumped into a heap and slept the night away.
With this stable of willing sexualists at his disposal, Dan had the vacation of his dreams. He has since come down every year for a break from the New England winter and to sample the latest delights Florida has to offer.