From Old to Young

Leo stepped out of the shower, dripping on the mat, and walked over to the sink, looking at his naked image in the mirror. He ran his hand through his wet hair, moderately thick on the top, crew cut on the sides. He smiled as he rubbed his hand down his trimmed light brown beard. It felt so good under his fingers. His green eyes glittered with the stare of youth as he studied his image. He then moved his hand down onto his chest, fondled his nipples, button-sized and pinkish, feeling them harden under his fingers. He rubbed the patch of hair in the middle of his chest, following the trail down, feeling his defined abs, rippled. He circled his index finger around his belly button then down to his black, curly pubic hair, giving out a low moan as he ran his index finger down the long cock shaft hanging over his fuzzy balls, shuddered.

The young Leo took a couple of steps back to look at his crotch. His hand went down onto his cock again, rubbed slowly and gently down the shaft. He cupped his fuzzy, low-hanging ball sack, then onto his hairy thighs. Another moan. He grinned. “Fucking sexy fucker.” That was what the old man had called him: fucking sexy fucker. Oh yes, Leo thought to himself, the grin widening to show his almost perfect white teeth; I am a fucking sexy fucker.

He was born Leonardo. His dad was “fond” of da Vinci. But everyone knew him as Leo, sometimes as Lenny. He’d had a good life so far. He had immediately found a job editing manuscripts upon his graduation two years ago. As an English major, he enjoyed the work as well as the pay, affording him a small apartment and independence from his father, who was loaded. He had refused any help from his rich dad although he had often noticed that his bank account was being fed every now and then from discreet “donations” made by his father. He was an only child and before he left home to live on his own, he parents had doted on him. Yes, Leo had it good: economically, academically, and, as he studied his naked image in the mirror, physically.

Leo caught the image of his naked shoulders and back in the wall-sized mirror behind him. His torso tapered down to his narrow waist in a v-shape, and his butt cheeks stood out, fuzzy and bubbled. He squeezed the muscles of one cheek, making it ripple, then the other cheek, then both cheeks, and laughed. Sexy fucker indeed. His balls tingled when the image of the old man came to his mind, the old man’s tongue licking and slurping on his butt and into his hairy crack hungrily, lustily, admiringly. Leo called the old man: Oldman. As if that was his name. They both laughed when Leo called him “Oldman”, although Leo thought that the old man was not very excited about the name but was too horny and eager to please Leo to object.

Leo’s dick elongated to a semi-erection, not yet to its full size of 7 inches, as he thought about his affair with Oldman. It had started in a chance meeting in the street in front of Oldman’s apartment suite. Leo did not have a “come-on” look that advertised his sexuality, but Oldman somehow knew that Leo was a possible prospect, and he was not too shy about asking Leo if he would accept a beer invitation. In the bar, Oldman grabbed Leo’s crotch under the table unabashedly, making it clear what the beer was for. Leo had never been with older men, but he was excited about the attention he was getting from Oldman. When Oldman suggested that they move up to his penthouse, Leo didn’t hesitate. He even grabbed Oldman’s butt as they walked down the corridor from the elevator to the penthouse. Instead of feeling horny, Leo somehow felt naughty; Oldman was almost his dad’s age.

Once inside, neither of them wasted any time. Oldman was immediately on his knees, yanking down Leo’s jeans and briefs, and gulping the engorging young cock down his throat, desperately lustful for the erecting rod in his mouth, pulling back on the skin as he worked the pink knob and the glistening slit. A few minutes later, Oldman was rewarded with a full nut, creamy and thick, squirting down his throat.

Leo had thought that that was what Oldman wanted, a quick cock sucking session, as Oldman smacked his lips, a gratified smirk on his face. However, Oldman hadn’t yet realized that Leo was the kind of guy who could sustain an erection after he unloaded and could go 4 or 5 times in a row if things were right. Therefore, when Oldman licked out the last drops off Leo’s cock slit, he was amazed that the man tool in front of his face didn’t start to droop down to a limp state. Instead, it angled up majestically, making Oldman take in a deep breath and worshipfully fisting it, looking up at Leo’s staring eyes and handsome face.

Leo had picked up Oldman and laid him on his back on the couch in the middle of the penthouse seating area, spreading Oldman’s legs wide, kneeling between them as he spat into Oldman’s exposed butt. He didn’t wait for Oldman to prepare himself but rammed his throbbing cock inside the twitching hole, bare and hard. Oldman’s scream was muffled by his arm as he bit into it to take in the sudden pain of the thick cock raping his hole. Oldman had desperately grabbed Leo’s muscled thighs with both hands, digging his fingernails into the skin, trying to ease the pain of the invading cock.

Leo watched Oldman’s face, squeezed in a mixture of pain and pleasure. Leo knew that his cock was prone to do a lot of damage when he fucked hard. But Oldman took the pounding under Leo’s forceful thrusts, his small penis flapping from side to side, his chest heaving, his breathing coming out in pants and bursts.

Leo’s second load squirted deep inside Oldman’s guts. He noticed the shiny droplets on Oldman’s belly, a sign that he had cummed as Leo was ramming into him.

This was just over three weeks ago.

Until now, Leo had spent the whole time enjoying the lavish delicacies and amenities of Oldman’s penthouse. He didn’t have to report to work. As a junior editor in a publishing house, Leo received the material over the Internet and did most of the work outside the office. He only had to report in whenever there was a meeting or for verbal instructions and discussions with the senior editor in the firm.

During those three weeks and as Oldman left for work in the late morning, Leo had spent the time idling, showering, working, surfing the net, simply enjoying a life he had never experienced before. When evening arrived, Oldman would walk in with some package in his hand, a gift, every day, with a smile on his face and a twitch in his ass. The gifts were a sign of appreciation of the young sex Oldman was getting: A set of Calvin Klein tight boxer briefs, a Hilfiger polo shirt, a diamond ear stud for Leo’s pierced ear, a bottle of Armani Code, and such.

At first, Leo had felt like a kept guy, but he couldn’t resist the gifts although he could have afforded buying some of them for himself. He definitely wouldn’t have accepted any money, but a gift was a gift. And Leo had been fulfilling Oldman’s sexual urges to the maximum.

Leo gazed at the mirror as he fondled and pulled on the diamond ear stud, the jewel glinting under the lights. His cock started to move from its semi-state to full erection. He moaned and grabbed the shaft pulling down on the skin to reveal the pink knob. He closed his eyes and stroked, the image of Oldman squirming under his pounding hips still so vivid in his mind. He could actually see the glistening of sweat sprinkled into Oldman’s graying chest hair, Oldman’s pinkish nipples and his protruding belly. Not exactly a David, Leo smiled, but definitely a body that had taken Leo’s punishing fucking bravely. Leo quickly let go of his hard cock as he felt close to squirting, reminding himself of the date he had arranged for tonight.

Actually, Oldman’s ass had not been the only exclusive sex that Leo had during those weeks.

One morning, a couple of days after meeting and hooking up with Oldman, Leo had walked out of the shower with the inevitable erection and a towel around his waist to open the door for the breakfast delivery he had ordered: 2 croissants (one chocolate, one cheese) an orange juice and a pot of black coffee. The delivery boy’s chin fell as his gaze spotted Leo’s tented towel. As Leo took the delivery bag from the boy, his towel came loose and dropped onto the floor exposing his big hard cock. The boy, who couldn’t have been more than 17 years old, or perhaps 18, emitted a loud moan, his eyes glued on the erected man meat. Leo had noticed the interest and immediately acted on it.

“I can understand why Reginald has not been around much,” the boy smirked, nuzzling under Leo’s pit, his sweaty body pressing on Leo’s and his ass seeping cum onto his thighs. The fucking had been awesome for both young men. The sheets were covered with new cum added to the loads that Leo had shot during the night.

“Reginald?” Leo raised an eyebrow, smirking.

“Yeah, the man you’ve been fucking for the last couple of days, dude,” the boy said.

So, Oldman’s name was Reginald.

“Oh? You’ve been with him too?”

The boy laughed. “Yes, you bastard, I was fucking him almost every day, but with you here, my livelihood is shot to hell.”

Leo laughed and smacked the boy’s butt hard. “Now get going. You will get your Reginald back soon enough.”

“I love your cock, though,” the boy murmured, fisting the still hard cock in his hand, feeling it slimy with cum and throbbing.

“Suck it,” Leo grunted.

The boy soon received another thick load down his throat. His instructions had been to bring breakfast to Leo every day and in return get both a mouthful and an assful of Leo juice.

Leo smiled to his image in the bathroom mirror. Fucking sexy fucker. Oh, yes, that’s definitely me: a fucking sexy fucker. He had never learned the delivery boy’s name, but the boy kept delivering breakfasts and getting fucked almost every morning after Oldman left for work.

It was not that Leo was particular about sex. His simple preference was that his partner enjoyed what they were doing. That enhanced his eroticism. When the woman’s tits under him hardened and his cock slipped into her flooding pussy, when the guy’s throat bobbed up and down as he thrust deep into his mouth, when the man ass ring clamped hard on his invading cock, all of this would set Leo up on new heights of sexual gratification. Old or young, smooth or hairy, busty or flat, whoever showed Leo signs of appreciation would make his sexing worthwhile.

The grin still on his handsome face, Leo toweled off the remaining beads of water and walked out into his room, a small bedroom in his two-room apartment. He missed Oldman’s huge penthouse and all the amenities, but after 3 weeks, he had started to feel cooped up. Now he was back “home” and free. And he had a date, sort of.

Leo had met Jimmy online two days ago, when he was still in Oldman’s keep. They skyped. Jimmy looked sexy and was around Leo’s age. The second skype session, Jimmy was sitting with his naked torso visible, smooth and silky looking. Leo had pulled down his jeans and stood up, revealing his hard cock. A few seconds later, Jimmy squinted his eyes, opened his mouth, grunted, and squirmed hard. Leo saw the drops of cum hit Jimmy’s laptop screen. Jimmy had cummed just by looking at Leo’s hard cock through virtual space. Leo’s balls tingled at the thought that by merely seeing his cock Jimmy had shot his load. He wondered if while getting pounded in the ass, Jimmy would shoot his nuts without touching himself. That would be awesome, the ring spasming wildly around Leo’s cock, milking him for every drop of man cum. His cock throbbed almost painfully.

Oldman had been very appreciative of Leo’s sexy body and sexual prowess. Would Jimmy dote on him in the same way, he wondered? He pulled on the pair of Calvin Klein briefs that the Oldman had given him, tucking his erected cock inside, stretching the cotton sideways, bulging deliciously. Jimmy would like that, Leo smirked. He dabbed some Armani Code on his chest hair. And then he sprayed a little into his pubes, knowing that by the time Jimmy’s face buried in there, it would be a mixture of man musk and expensive perfume filling his nose. Would he ejaculate as he sucked and inhaled Leo, his throat vibrating on Leo’s knob, his jizz hitting Leo’s hairy legs and feet?

Later that evening, after a pizza dinner with lustful looks and suggestive body language between the two young men, Leo pulled Jimmy into his apartment, grabbed him around the waist and planted his tongue into Jimmy’s moaning mouth. The two young men pressed on each other, both erected, both hungry for each other, both making out. As Leo grinded on Jimmy pressing him against the door, he felt wetness on his crotch. He stepped away and looked down, noticed Jimmy’s crotch spotted wet through his light-blue linen pants. He stared up at Jimmy whose look of embarrassment said it all.

“I couldn’t help it, Leo,” Jimmy whimpered.

“You cummed just by making out?” Leo said incredulously.

Jimmy hung his head down and nodded.

Laughingly, Leo grabbed Jimmy’s waist and pulled him in and onto the couch. Slowly, he pulled off Jimmy’s pants and sodden briefs. He leaned and kissed Jimmy on the mouth, his hand caressing the slimy limp cock.

“Undress me,” Leo told the whimpering Jimmy, whose red face clearly signaled his embarrassment at his premature ejaculation.

Jimmy sighed deeply, running his hands on Leo’s hairy chest, fingering around the nipples, tracing the trail down to Leo’s waist. Leo smiled as he noticed Jimmy’s limp cock spring back to life. He leaned and fisted it. Jimmy, however, immediately pulled back.

“Oh, please Leo. I would shoot.”

Leo patted Jimmy’s face as he let go of the erecting cock, pulling Jimmy’s mouth onto his chest. Jimmy licked and moaned, undoing Leo’s pants, his hands shaking as he traced the huge hardness inside the Calvin Kleins. Dragging down the briefs, Jimmy pulled back as the hard cock sprung out and almost hit him in the face. Hungrily, he went down on Leo. As he gulped trying to get as much shaft inside his mouth as possible without choking, Jimmy shot his second load all over his smooth chest.

“Oh, Jimmy, you’re so hot,” Leo moaned as Jimmy licked the underside of Leo’s cock, still throbbing, still hard.

“This is your first time, Jimmy?”

Jimmy looked up, blushing, and nodded.

“Ever?”

“Yes. You are my first, Leo.”

“Incredible, buddy. You’re so hot. How come?”

Jimmy’s eyes got wet and he blinked moving away, sitting on the couch.

“I jizz fast, Leo. I can’t hold back. A minute or two and I’m shooting. It’s so… embarrassing. I almost cancelled coming here today. But you looked so hot and sexy and fucking nice, that I couldn’t walk away and not have sex with you. Besides,” Jimmy added in a whisper, “I only care for your juice inside me.”

Leo laughed, sitting next to Jimmy and hugging him.

“Let’s fuck, Jimmy,” Leo bit Jimmy’s ear playfully.

“Oh, God, Leo, I want that so bad.”

Jimmy turned on his side letting Leo spoon him from behind. The hard rod pressing on his fuzzy butt cheeks made Jimmy shudder. Leo knew that he was big, too big for virgin ass, which made him even more horny to fuck. He rubbed his cock head inside Jimmy’s crack, between the pressing thighs, humping, leaking, making the hairy crack slippery. He reached down and wiped the hole with some spit. Jimmy’s moans came out as pleading.

Naked, the two young men lay on the bed, making out. Leo avoided touching Jimmy’s cock. But when he pushed his own hard erection between jimmy’s thighs and humped under his balls, Jimmy shot for a third time. Using Jimmy’s cum, Leo thrust into the panting and eager Jimmy, driving deep and fast, taking advantage of Jimmy’s after-jizz relaxation.

The fucking was intense, with Leo pounding and grunting on top of Jimmy. Leo needed to unload quickly so as not to embarrass Jimmy even further. When he did ejaculate, his squirts shot deep. It was so unlike his fucking Oldman or the delivery boy. Although gratified, Leo felt that he was doing Jimmy a favor instead of enjoying the love making himself as well. He wasn’t sure whether Jimmy shot any more loads while he was fucking him.

“You’re still hard, Leo, inside me. You cummed, didn’t you? I felt your dick get thicker and the squirts sliming me. But you’re still hard. I can feel it, still stretched, still sore,” Jimmy whispered as he pressed back onto Leo’s hairy crotch.

“Yea, Jimmy,” Leo grunted, grinding on the pressing butt cheeks, his cock flexing inside the wet tight hole.

Jimmy couldn’t believe his ears.  This stud had just shot a huge load and he was still hard. As Jimmy turned his head around, Leo grabbed him by the waist pulling out his slimy cock and rubbing it on Jimmy’s butt and up his back spreading the seeping cum. Slowly, he then pressed on Jimmy’s back, bending him over. He knelt behind Jimmy, and, spreading the fuzzy butt cheeks with both hands, Leo started to lick up and down the crack, his tongue pressing on the twitching hole, tasting his own cum and slobbering on the stretched hole. He barely heard Jimmy’s moans, begging him to fuck again.

Straightening, fisting his shaft, Leo pressed the knob at the ring. When he thrust and penetrated, Jimmy screamed. Leo held the knob inside the rim muscle.

“You ok, baby? Hurts? Should I pull out? Is this worse than the first time?”

Jimmy grunted, gritting his teeth to be able to take the searing pain in his sore ass.

“Oh, oh,” he finally managed to say. “Just gimme a second. My ass is so sore, Leo. Fuck!  It’s so big. And you’re so beautiful.”

Leo stayed, his hand grabbing Jimmy’s cock, feeling it leaking into his hand. He stroked it slowly, feeling the ring muscle press hard on his cock ridge. Nudging slowly, as he had done when he was feeding Jimmy’s mouth, Leo was able to force a couple of inches into the tunnel. Jimmy reacted by pushing his butt back onto Leo, as more inches of cock shaft invaded his hole. Grabbing his own legs as he bent over, Jimmy whimpered, taking hard cock deep.

“Fuck me, oh my god, yes, please fuck me Leo. I love you. Oh,” Jimmy managed to say, his whole body taut with the force of the man cock invading his ass.

Leo buried inside his new lover, grinding on the hot butt. He grabbed Jimmy’s shoulders with both hands and started a slow and long fuck. Increasing his tempo, clutching hard onto his lover’s shoulders, he fucked, grunting, starting to sweat. He bent and licked up and down the bent back, fucked harder, fucked faster. Suddenly, Jimmy’s ring muscle tightened on the thrusting cock, Jimmy’s head jerked backwards, and Jimmy lost another load, squirting hard without touching himself.

With a loud growl, Leo exploded inside Jimmy’s guts, dumping his thick load. Jimmy almost collapsed.

Panting and sweating, the two lovers lay next to each other, Leo’s arm under Jimmy’s head, Jimmy’s face buried inside Leo armpit.

“That was awesome, baby. But I think you will be walking sideways for a few days,” Leo snickered.

“I love you,” Jimmy responded, pressing his shivering body onto Leo’s sexy body. “I fucking love you.”

Leo laughed, kissed Jimmy’s lips. “I love you, too, hot stuff.”

“So I count as your boyfriend now?”

Again, Leo laughed, and licked the sexy lips. “Yes, Jimboy. You are officially my boyfriend. You can feel my sperm inside you.”

Jimmy moaned into Leo, his ass sore and throbbing. Leo pulled Jimmy harder to him, his cock wonderfully erecting again. And, in spite of the pain, Jimmy guided the hard thick cock back to his twitching hole and took the initial thrust and penetration, rewarded by a full-sperm load minutes later.