Jim's Boys

by Gaystoryman

27 Dec 2018 2955 readers Score 8.6 (38 votes) PDF Mobi ePub Txt


He wasn't a pervert, least he didn't think so. Okay, so he was nearing retirement age, and he liked his men young, now that didn't make him a pervert, just selective. He had put in his 35 years, and this was the time when he believed was the time to enjoy the fruits of those 35 long hard years. Some of his colleagues didn't quite agree, but then they were so stuffy that it was suffocating at times.

Jim wasn't a doddering old fool either. Just grazing his sixth decade of life, he had no regrets. His life had been full, and while he never had found that special man, he had no trouble keeping his bed full of warm bodies. When he wanted solitude, he simply didn't bring anyone home. It was an ideal life, as far as he felt, despite the constant meddling of his associates.

Many were surprised last year when he took his retirement from the school. He could have stayed on another five years, but after doing the number crunching with his accountant, he realized the pension he would get now wasn't all that much less than in another five years. So why spend five more years putting up with Government bullshit? Ever since the conservatives had taken power with Bush, things had gotten worse, in his estimation. A resurgence of the Democratic Party didn't look like it would be any better, so he took his pension and didn't look back.

While at times he missed going to class, to stand before all those pimply faced teenagers, he didn't miss the blank stares many had plastered on their faces. He didn't miss the endless bickering with the administration on lesson plans, or on what he could or could not discuss. In truth, he was glad he left and besides, now he didn't have to worry who saw him go in or come out of the Gay bars. And he did enjoy the bars.

When he walked away from the 65 year old cement & brick building for the last time, he didn't feel any regret. He was excited, because now he could enjoy the fun. He had saved, scrimped and tucked it all away for 35 long years. He had put up with administrators who couldn't add one and one, let alone figure out how to fill a classroom, or how to organize a staff schedule. He had put up with the bullies, with lackeys who were using their administrative position to jump start their own agendas. He had done what he had, did the ass kissing when left with no other choice, but as he had walked away from the school for the last time he felt free to finally be himself.

It hadn't taken him long either, to realize that he had missed out on a lot. Being Gay was different than it had been almost fifty years ago when he first realized he was Gay. Still he had had his moments, but always had that caution holding him back from enjoying life to the fullest. Now there were no restraints and he had the boys to prove it.

Over time he realized he liked his partners young. They at least could keep up with his sexual needs and his own insatiable sex drive. No Viagra for this sectarian. He could get it up without any trouble, and keep it up too. Unlike some 40 years his junior, he could keep erect for long stretches, naturally.

There were some who said he'd hate retirement. Man were they ever wrong, because he had it all planned out. After all, teaching sciences for 35 years you learned how to plan things out. He had no family, no obligations that kept him tied to where he lived. So he plotted his trips carefully, making sure they would be a learning experience as much as a trip to relax.

That was all fine, but when home, he also liked to have fun. He wasn't sure when or how it had all begun, but as he began to pack his bags for his latest adventure, he realized that he had a pretty interesting routine and collection of young men.

Monday was Richard. Whenever in town, he would meet Richard for a late lunch, usually about <em>two ish</em>. It was generally at Richard's small little apartment, and there always was a good meal ready for him. Richard was learning to be a chef, and worked nights at a local bistro. He also was gorgeous.

He wasn't tall, maybe about 5ft 9in in stocking feet. He had dark hair, rather sad looking eyes and because he was in a kitchen, his face was always pink and dotted still with pimples. It was the grease in the air, or so Richard had said. However Jim didn't care, as Richard was a sweetie. He liked to cuddle, but his best attribute was he loved to suck cock. Richard might have a talent at cooking, but his real talent was how he could take a dick, and make your whole body tremble as he sucked on it.

Every Monday that he was in town, he started his week off at Richards. The lunch would be light but filling, then they would go to the living room area, where Richard would always do a little strip tease, dropping his shirt and pants and showing off his own firm and full basket. He would tease Jim a little, then somehow manage to undo his shirt, and warm him up by some kissing and hugging.

By then Jim would be on the chesterfield, his pants off to one side, and Richard would begin to work him over. He was a 22 year old who loved to play, but his mouth while looking tiny, seemed to be on hinges. Jim wasn't what you would call tiny and Richard never seemed to have any trouble in taking it all, with ease.

He would lick at the base, the balls, touching him elsewhere while his tongue worked its magic. Richard knew how to please, how to apply pressure at certain spots, when not to. His fingers would always probe, and touch. They would find their way up to his nipples, tweak them and excite them. All the time his tongue would be licking at his belly, or at his inner thigh. It would circle the base of his rather thick cock, that always seemed hard when around Richard.

The way he would run the tip of his tongue up and down the underside of his stiff cock always made him groan, made him shudder too. Just the tip of the tongue would lick at the throbbing vein underneath, and then it would curl up around his cock head, licking under the cap, then across the head. By then he would be oozing pre cum and Richard would quickly lick it up, make a sound of enjoyment, then suddenly engulf his whole cock. He would take it all, in one single motion, pressing his lips hard up against his groin. The hands would suddenly be down and cupping his balls, while the lips pressed hard.

Pulling his head back, Richard would let his lips press tightly against Jim's burning flesh. He could feel the taut skin being pulled by the pressure, and then, just when he would think Richard was going to let go, the mouth was racing back down his throbbing pole. His whole body would always shudder, and it would go on and on. Each time he thought he couldn't hold back, Richard would sense it, and suddenly the urgent press for his milk would ease. The lips would open, and suddenly his throbbing cock would be kissed and licked from all angles. The hands would release his balls, and rub his thighs, caress his belly. His lungs would be aching, and he would be panting as Richard would take him close two or three times, then when he was pleading for him to let him cum, he would just stop. He would climb up and cuddle, kiss him hard on the lips and keep on hand slowly stroking his cock.

There were times when he thought he just burst, but Richard knew him, knew how to keep him on the verge. After some kissing, some fondling, he'd work his body back down, to wedge himself between Jim's open legs. His head would rest on Jim's thigh, and he would know that this time, he'd get his wish.

That was his Monday routine now, and it was so much better than having to spend countless hours going over the week's plans with some dickhead administrator or department head. He rather looked forward to those Monday lunches.

He had found Richard shortly after his retirement, which was why Tuesday became Adam's day, after Jim found him. He was working at the local grocery store as a stock boy and bag boy. Now he was a cashier there, and he liked to think it was because of him. It was not just fun to have sex with Adam, but fun to watch him mature and grow.

Adam was tall, unlike Richard. He sported a crew cut type hair style, and the bristles were rather enjoyable when they had their little rendezvous every Tuesday after supper time. It was fun to meet him at the supermarket parking lot, and to smell his special scent as he climbed into his car. If no one was around, he usually got a very passionate kiss on the lips, and a quick grope of his crotch. He liked that, and yet when someone was around, he felt even more excited, knowing how it would be once they got to their special place.

One of the benefits of living where there was two seasons, hot and hotter. They had a small little spot among a grove of trees, just outside of town. It wasn't a popular spot for people, off the beaten track really but best of all, there wasn't any houses within miles. They could talk without having to whisper or worry about being stumbled upon by others. After their first time there, Jim did begin to make sure he had an air mattress and blanket in the trunk.

Unlike Richard, Adam didn't suck very well. He was okay, but that was about it. Adam's talent lay in how he worshipped bums. His dark eyes would bulge every time he saw some derriere that was firm and had just the right wiggle to it. Obviously he thought Jim had one of those, which was rather flattering for a man his age. Nice to know that even at his advanced years, a 20 year old could admire his tushie.

Strange too, that a guy like Adam who had a nice wide fat tongue wouldn't be good at sucking cock, but at licking an ass, the guy was unbelievable. The way he would spread his cheeks, kiss him on either side, always made his body quiver. The way he would work his tongue up and down his crack, and yet avoid his hole until just the right moment, was always a thrill.

On the surface, Adam was a typical kid. He wore those stupid baggy pants, loose fitting shirts and acted like he was about to run and hide. To say he was a nervous insecure kid would be an understatement, until he was behind a butt that he liked. Then he was like a Tiger, the way he would lick and kiss and spread those cheeks. He had ways to work his tongue deep inside that made Jim cry out each and every time. It truly was amazing at how he could lick him, and control him too.

That was one thing he liked, the ability to not cum before it was time. Adam, like Richard, could sense the timing, and always managed to find ways to hold him back. The touch of his hands or fingers would make him tremble one second, then cool down the next. He always sweated buckets Tuesday nights, and he enjoyed the shower afterwards too. Adam wasn't exactly cute, but he had a certain charm that had attracted Jim and now made Adam one of the boys.

Wednesday was different. That was when he would generally just take a deep breathe, stay home and enjoy an extra glass of wine. He'd maybe read a book or too, but come Thursday it would be time for his standing dinner date with Dale.

Like Adam, Dale wasn't a raving beauty. He was 23 or 24, Jim couldn't quite remember, however Dale was thin, tall and in his own way attractive. He had piercing dark eyes, that didn't quite match his body, which was thin and rather bony. Yet he was full of life, once he was aroused. Hence the dinner first, as it took Dale a bit of time to get warmed up. He still wasn't all that comfortable in his 'gayness' but that was okay, Jim was working on that.

Dale was shy and had a habit of always looking down at his feet. They were rather large for his body, but he was also a clean freak. It was strange, but Dale preferred to spend time in water, mostly a tub with a shower attachment. He liked to play and Jim had a nice pool in his backyard. The biggest attraction was the high fence that surrounded the backyard too, because it gave him the freedom to enjoy Dale, to the fullest.

Dinner was nothing fancy. It was afterwards when they would go back to Jim's home, off in a rather secluded neighbourhood. There they would sit and chat for a bit. When he'd notice Dale beginning to look out the patio door, he knew it was time to suggest an evening swim. After all, the pool was heated and it was never cold outside. That was always met with a rather sly looking grin, and a quick hop of the chesterfield to race outside.

There Dale would quickly strip totally naked. Jim was always a bit slow on that, but he enjoyed the flash of Dale's white cheeks as he would race to jump in. He would bop up and wipe his hair out of his eyes, stare up at Jim and watch as Jim undressed, also forgoing any swim gear. Once naked, he would casually walk to the edge, enjoying how Dale would stare at his body, at how his eyes would fix on the hard cock that always stuck out. He would look down, smile and dive in and then the fun would begin.

Dale had one unbelievable quality, he could hold his breathe for amazing lengths of time. They would swim and every now and then, he would suddenly find Dale under him, playing with his cock and balls. He would actually take his cock into his mouth, while under water. It was amazing, at how good it felt too. The sudden sensation of being taken, and sucked for what seemed minutes made him always tremble. They would splash and chase each other across the pool, and every now and then he'd be surprised by Dale grapping his ass, then wrapping his legs around Jim's waist, as they would kiss while treading water. At times he'd find himself sinking, but it didn't matter. Kissing under water was still a weird sensation, but damn exciting.

Every now and then, they would climb out, lay on the side and have more fun. Dale would usually suck him off, lick him and on the odd time, let him return the favour. He enjoyed sucking the young man off. He had a nice uncut cock, and it had taken him a bit to realize that. It too, like his, was always erect. At first he had thought he was on something, but it was simply that Dale was a horny guy, just like he was. That realization always made him smile, and reach down to give his own dick a squeeze, just like now.

He enjoyed playing with Dale's equipment. The cock was one of those that had a slight bend near the cock head. It was natural but gave the appearance of being hooked. It certainly tasted good, after their horseplay in the pool. It had a nice taste, and the pubic hairs were always trimmed. One of those nights, he'd have to ask him who did the trimming. It was pretty good and each time he would slide his mouth down Dale's throbbing pole, he would stare at the V shaped pubic hair.

While he considered himself pretty good at sucking cock, he was no Richard. Most times he didn't quite sense when he was going to fast, or that Dale was close. He didn't have that down, but he didn't really care because he was always lost in the moment, just enjoying the taste of the hard dick. He liked the scent of the young man, that mingled with the pool water. It was intoxicating, and once he got started on that hard dick, he felt his own cock aching.

Dale was a moaner too, which he liked. Each lick of his tongue, each gobble of that cock deep into his throat would make Dale groan. It was all part of the moment, that made him forget to watch out for that time. It was why he generally was surprised when Dale would scream out that he was coming. And he could cum too.

Rarely did he managed to take it all. Lots of that sticky salty mix found its way out of his mouth. He just couldn't swallow fast enough, but the way the cockhead would rear back and fire outwards so fast, was amazing. It always took him by surprise, as one second the head would be lodged deep in his throat, then suddenly it would jerk back, and before he could process the thought, it was digging deeper than before. It was also pouring out a steady stream of hot cum, that always made him gag.

His throat was never ready but he managed to always take the second stream without letting a drop escape. It tasted great, and once the cock had finally emptied, had finally stopped its jerking, he would pull back, letting it out slowly. He would lick the head, kiss it and even lick under, tasting as much as he could.

Leaning back, he'd stare at Dale's heaving chest, feel it rise up and down, as his own head had just finished doing with Dale's cock. It was then that he would get up onto his knees. He would lean over the still panting chest, and begin to grab hold of his own cock. It was rock hard.

He would look down, to see Dale staring up at him, his eyes wide open and showing their desire. He would not close them once during the few minutes it would take him to stroke his cock and shoot his own cum all over the young man. He would start slow, but the way Dale looked at him always got his hand moving faster with each stroke. The ache in his own body helped spur him on, as well.

Jim would feel the ache in his own chest, feel himself begin to pant as he stroked his hard cock. His own pole was hot to his touch, as his hand would go faster and faster, until he felt his balls slinging upwards. At that moment, Dale would reach out and run the back of his hand across his taut thigh. It was like being hit by lightning, and he would close his eyes, as his body would quake and shake as the cum began to flow through his penis. It would come exploding out in a second, and he would catch the last of his first load splattering across Dale's heaving chest.

The sight of his thick cream hitting that tanned body would only make him cry out more, and this time he would manage to keep his eyes open, as his second stream would already be flowing out, striking the young man in his upper chest, and into the hollow of his neck. Dale would be watching, his eyes like huge saucers as Jim would shake his cock, feel the last of his cum dribble out. He would lean back on his legs, feeling the numbness begin to disappear. His own chest would be tight and constricted, as he would be panting a little, and he would look down.

Dale would be rubbing one hand over his whole torso, wiping the cum all over him, and once finished he would lift both arms up, spread open so that Jim could fall down and be held by him.

They would kiss and he would feel his cum drying between them. His body would be sticky, his skin melting into Dale's own flesh. It really felt good, and then it would end, and Dale was off to once more jump into the pool, with him following quickly. They would splash each other, like a couple of kids would do, and it would begin all over again.

It was like being a kid all over again. They would splash, play, and climb out to have their special fun. Then back into the water they would go, and it would go on until midnight most Thursdays. After Dale would leave, Jim would be exhausted, and his cock would be totally limp. Heading to bed on Thursdays, would always end with him smiling, knowing how totally spent he was.

Looking down at his suitcase, he realized he was all packed and ready to head off on his trip to Brazil. He wouldn't have Richard on Monday, Adam on Tuesday or Dale on Thursday, but he had an idea that he would find something in Brazil to help make him not miss them too much. After all, he had seen a picture of his tour guide. It looked very promising as he grabbed the suitcase to go wait for the taxi.

by Gaystoryman

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