An Afternoon to Remember

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Darrin entered the bar and sat down at an empty barstool. He ordered a whisky and water and sipped at his drink. He was extremely peeved that his customers had all cancelled his appointments, but decided that he would just forget work and try to have some fun. His plane reservations were for the next morning’s flight home and all other flights were booked which meant he was staying here overnight. He looked about and saw that there were only three people in the bar, the bartender, another customer at a table and himself.

He ordered another drink and struck up a conversation with the bartender. Darrin asked if and when the bar would get busy and what time should he expect some women to show up. The bartender smiled and told him that it would get busy around five o’clock, but he doubted if any women would show up. Darrin looked puzzled at the bartender’s response then realized that he had entered a gay bar. The bartender confirmed that he was indeed in a gay bar, but not to worry because no one would bother him. It was too early in the day.

Darrin shook his head as he smiled at the bartender, “Just my kind of luck,” he said.

“Don’t knock it if you haven’t tried it,” the bartender replied with a smile as they both chuckled.

Darrin decided to finish his drink before leaving. As he sipped his whiskey Darrin thought back to several years ago when he had attended a wedding here in Youngstown, Ohio. He had met a married couple at the wedding that ultimately led to a three way encounter including his first bisexual experience. Scott and Beth were their names and he had told them that he would call them when he was next in town. Unfortunately, he had forgotten their last name. ‘Too bad,’ he thought, ‘it would have been fun seeing them again.’

The door opened, interrupting his thoughts, and he turned to see a man come in to sit down a few barstools down from him. As the man‘s eyes adjusted to the bars dim light, Darrin saw that he was a young man in his early twenties, casually dressed. The man ordered a beer and nodded to Darrin as he took a long pull on the beer bottle. He smiled at Darrin, then turned to mind his own business as they both sipped at their drinks.

After several minutes had passed, Darrin heard the man ask, “Like another?” Darrin turned to see the younger man offering to buy him a drink. He nodded and accepted the young man’s offer. The bartender brought the drinks and returned to his duties as the young man picked up his drink and moved to sit next to Darrin. “Do you mind?” he asked. Darrin smiled and said ‘no’, inviting him to sit next to him. “Thank you, I’m Tommy,” he said offering a hand shake. Darrin told him his name and shook his hand.

They engaged in mutual small talk about jobs, home location and what each was doing here etc. Darrin told Tommy that it was only his second trip to Youngstown and inquired if Tommy knew a ‘wild’ couple whose first names were Scott and Beth. Tommy replied that he didn’t and asked if they were friends of Darrin. “No, they were not friends, more like acquaintances,” Darrin replied, “But they sure were wild.” He related the story of his escapade with Scott and Beth, but left out the bisexual episode with Scott.

Darrin bought the next round and the conversation turned more personal as they drank. Tommy admitted that he was gay and that Darrin turned him on. For some strange reason, Darrin felt himself becoming aroused as his cock stiffened and his pants bulged at the zipper. Tommy looked at the bulge in Darrin’s pants and asked him if he had hit a nerve when he admitted that he was gay. Darrin nodded then went on to tell Tommy all that had happened with he and Scott following the wedding.

To some extent, it was the whiskey talking, but additionally, Darrin admitted, he too was turned on by both the wedding episode and Tommy. Smiling, Tommy reached out and placed his hand on Darrin’s pants and squeezed his hard-on slightly. Darrin sighed and quivered slightly, but did not move to stop him from feeling his hard cock. “Wow, Darrin, that’s quite a package you’ve got there,” Tommy said softly. Darrin drew a deep breath and decided then and there to go along with the flow.

Tommy’s had unbuttoned the first three buttons on his shirt and Darrin quietly put his hand into the open shirt. His fingers butted against Tommy’s nipple and lightly began to rub it. Tommy sighed and his face flushed a little as he obviously enjoyed Darrin rubbing his nipple. Darrin gently tugged at the nipple until it hardened into a pointy cone. Tommy’s breathing became hard as Darrin grasped the nipple in his thumb and forefinger to roll and gently pull it.

“God, I love that,” Tommy gasped as Darrin continued to rub and tug at his nipples. Darrin quickly withdrew his hand from Tommy’s shirt as the bartender approached. He declined another drink and then brought out his pen. Darrin wrote the name of his hotel and his room number and gave it to Tommy who nodded as he read the note. Darrin rose up, tipped the bartender and walked out of the bar to his hotel across the street. He entered the elevator and went to his floor, then immediately to his room.

Inside he removed his tie and hung his suit coat in the closet. The encounter with Scott and Beth raged through his mind as he waited for a knock on his door. Finally, there was a knock at the door and Darrin quickly moved to the door to look and see who it was through the small viewer in the door. It was Tommy. He opened the door and Tommy quickly stepped inside. Somehow Tommy sensed that Darrin wasn’t into kissing and he quickly undressed to stand naked. Darrin quickly removed his clothes and stood naked as Tommy embraced him.

An electric shock coursed through both of them as their cocks touched and rubbed while the contact of their hard nipples against each others chests made each of them quiver with lust. Tommy, more experienced though younger, clasped his hand around Darrin’s seven inch cock and led him to the bed by the cock. Darrin eagerly followed him, enthralled that Tommy pulled him along by the cock. Tommy laid Darrin down on his back and climbed on the bed next to him.

Tommy straddled Darren’s waist with his knees as he bent to kiss and lick Darren’s nipples, first one and then the other. Darrin gasped with desire as the tongue swirling and licking his nipples swelled his arousal. Tommy was expert in suckling male tits and nipples as Darrin could feel the young mans’ hard cock pressing on his stomach as his nipples were pleasured. Darrin reached out under Tommy’s chest searching for his nipples too, finding them hard and pointy.

Tommy quickly moved his upper body over Darrin’s head to lower his nipples to Darrin’s mouth. Darrin twitched with desire as Tommy lowered his nipples to Darrin’s lips as he continued to lick, suck and nibble the older mans nipples. Both moaned with pleasure as their mouths surrounded each others nipples as they sixty nined one another’s nipples. Nearly simultaneously they each grabbed the others cock to fondle and stroke it while continuing to lick and suck their nipples.

Darrin estimated that both their cocks were about equal in length and thickness. Tommy had been circumcised, while Darrin had an ample foreskin surrounding his purplish cockhead. Both of them felt that they could and would cum just from having their nipples sucked. Finally, Tommy stopped and rose up stopping both of them from cumming. Thick clear pre-cum oozed plentifully from their cock holes and Darrin scooped up pre-cum from both cocks, offering his to Tommy, as he licked Tommy’s pre-cum into his mouth. The smooth salty texture satisfied them both.

Tommy moved forward over Darrin until their cocks stared one another in the face. Tommy rotated his hips as he lowered his cock and balls to Darrin’s face and rubbed them all over it. Darrin moaned in pleasure as the softness of Tommy’s balls rolled over his forehead, nose and mouth. Tommy teased him by not allowing Darrin to lick either his cock or his balls, try as he might. Finally, after a few moments of teasing, Tommy lowered his mouth over Darrin’s cock and took him deep inside.

In turn, Darrin happily took Tommy’s balls into his mouth and licked and sucked them. Both of them moaned with pleasure as their tongues swathed over their cocks and balls. Darrin could feel his orgasm rapidly building deep within him as his cockhead was repeatedly bathed with Tommy’s tongue. He erupted in a powerful orgasm spewing his cum deep into Tommy’s mouth, splattering against his cheeks and drowning his tongue with cum. Tommy continued to suck Darrin’s cockhead hard. He swirled his tongue over and around it until Darrin could hardly stand intense sensations the tongue bath was giving his cockhead.

Finally, Darrin slumped on the bed, drained and spent from the powerful orgasm. Tommy continued to suck hard on Darrin’s cock until he milked it free of cum. He swallowed Darrin’s cum and looked over at his exhausted lover. Darrin’s eyes were shut and he was gasping. After a few minutes, the effects of Darrin’s orgasm began to subside and he opened his eyes. “Wow, Tommy that was incredible! Now it’s my turn to make you cum,” he said.

“Later, Darrin,” Tommy told him, “I want to fuck your ass. Do you mind?” Darrin smiled as he shook his head no. Tommy rolled Darrin over onto his stomach as he placed his face on Darrin’s asscheeks. He began to lick Darrin’s asscheeks while his lover sighed and gasped with pleasure. Tommy drew his tongue down Darrin’s asscrack and swirled it around his puckered asshole. Slowly, but surely his asshole relaxed as Tommy’s tongue bathed it with his saliva. “Have you ever been fucked in your ass, Darrin?” Tommy asked.

“Yes, once…by Scott, at the wedding I told you about.”

“Good…I’m going to loosen you up a bit so it won’t hurt…as much.” He added. Darrin nodded as Tommy went to his pants and withdrew a small tube of KY lubricating jelly from his pocket. “Just relax, Darrin.” Tommy spread the jelly all around Darrin’s asshole then he gently pushed his finger into it. Darrin moaned as he recalled how Scott had once pleasured him in his ass, long ago. Tommy moved his finger in and out and around the sphincter to loosen and stretch it.

Darrin began to enjoy the finger in his ass as the initial discomfort subsided. Then Tommy added another finger and both of them fucked Darrin’s asshole as he moved them around to loosen and stretch it even more. Again the discomfort changed to pleasure as Tommy demonstrated his expertise. Darrin’s sighs of pleasure quickly changed again as Tommy inserted a third and final finger inside his lovers’ asshole. He could feel his asshole really stretching wide and it was now hurting. Tommy took his time as he slowly opened Darrin’s asshole in preparation for his cock.

Tommy continued to explore Darrin’s asshole with his three fingers as he told Darrin to rise up slightly and he placed a pillow under his now flaccid cock. Darrin lowered his body onto the pillow and realized that his ass was up higher in preparation for the impending invasion of Tommy’s cock. A last swirl of Tommy’s fingers in his ass preceded their withdrawal. Darrin realized that it was time. He tried to relax as much as he could, but he could feel his asshole begin to pucker.

Tommy lubed his cockhead and placed it on Darrin’s asshole. The cold KY jelly startled Darrin, but he took in a deep breath and exhaled deeply. He could feel the pressure on his asshole as his sphincter was being challenged by Tommy’s cock. He began to feel pain as his sphincter involuntarily resisted the intrusion of Tommy’s cock. Darrin tried to relax, but the effort was useless, the pain was still there. Tommy began to increase the pressure, slowly at first, but with increasing force while Darrin gasped as he felt his asshole spreading wider and wider.

After an initial burst of pain, Darrin felt the invasion pause as Tommy declared that his cockhead had just slipped inside. Tommy could feel Darrin’s sphincter closing just behind his cock rim and he paused to allow Darrin to become accustomed to the thickness. “Are you ok with this, Darrin?” he asked. “Do you want me to stop?”

“No…it’s ok…I want to feel your cock inside me, Tommy.”

“Try to relax…It will go a bit easier now that my cockhead is inside.” Tommy told him as the pressure to grow again at Darrin’s asshole. Darrin could feel the cock slowly sliding into his ass. Although it was about the same size as the cock that had first fucked his ass several years ago, it seemed exceedingly huge. The pain resumed as the huge cock drove deeper and deeper into his bowels. He held his breath until he felt Tommy’s pubic hair touching his asscheeks and then knew it was pushed ‘home’ as Tommy’s balls slapped at his balls.

“Good boy,” Tommy said as his cock had impaled itself deep into Darrin’s asshole. Again Tommy paused to let Darrin become acclimated to his cock. After a few moments Tommy backed his cock out until only his cockhead remained fast behind Darrin’s sphincter. Darrin sighed as he struggled with the pain, but would not tell Tommy to stop. He was determined to give his lover the pleasure he sought. Again Tommy slowly drove his cock deep into Darrin’s ass. After several initial thrusts, Darrin sensed that the pain was dissipating and being replaced with pleasure.

The change was not lost on Tommy as he began to thrust his cock faster and even deeper into the tight asshole that surrounded it. He reached under Darrin to grasp his cock and stroke it as he fucked him. Darrin responded with an approving moan as he began to move his ass back into Tommy’s forward thrusts. Now the pain was gone and Darrin reveled in the pleasure that was being bestowed upon him. Tommy realized that Darrin was now in pleasure and he grasped a half inch wide rubber band and looped it around Darrin’s balls. He twisted the rubber band into a figure eight and looped the other end around his own balls.

Now each time Tommy pulled back to withdraw his cock up to his cockhead. The rubber band pulled at each of their balls to enhance their pleasure! “Oh my God, Tommy!” Darrin cried out, “That feels fantastic!” Encouraged by the pleasure Darrin was receiving, Tommy began to thrust in and out faster and faster. All thoughts of pain had been erased from Darrin’s body. He lusted for release as Tommy continued to fuck him furiously. His balls responded to the pull of rubber band that encircled them with each withdrawal of Tommy’s magnificent cock as it churned the sperm within them.

Tommy was breathing hard and Darrin could feel his cock throbbing deep inside him in preparation to fill his ass with his cum. Darrin pushed back until he was on his hands and knees responding to each of Tommy’s thrusts with thrusts of his own. Both men were groaning as they fucked, spurred on by the relentless pull and release of the rubber band that held their balls captive. Darrin felt Tommy’s cock as it seemed to swell within him until it erupted in cascades of warm thick frothy cum deep inside him, filling his ass with cum. Tommy grunted with each spasm of his cock and continued to spew his cum into Darrin’s ass.

Finally, Tommy’s cock ceased cumming and his cock spasms stopped as he drove his cock deep into Darrin’s ass and held it there. At first Darrin felt the cock in his ass begin to soften, but then it assumed a semi-hard state. Tommy was lying on Darrin’s back breathing hard, his hard nipples pushing into Darrin’s back. Darrin too, was gasping with pleasure as the cock in his ass seemed to refuse to return to a flaccid state. Tommy began breathing more normal and his fingers reached around to find Darrin’s nipples. He rubbed them lightly with his fingertips as Darrin responded joyously to the sensations in his nipples and the semi hard cock still embedded in his ass.

After Tommy rubbed his nipples, Darrin’s nipples responded again hardened and aches with passion. He moaned as his lover began to grip them with his thumbs and forefingers to tug and squeeze them. He felt maddened with desire and reached under his legs to lightly rub and tug at both of their balls still held tightly by the marvelous rubber band. Then another sensation stirred deep inside him as Darrin felt the cock in his ass begin to swell and harden again. After a few moments Tommy’s hard-on had been rejuvenated to a full state of erection and began to renew its wonderful assault on his ass.

Tommy continued to rub and pull at Darrin’s sensitive nipples as he resumed fucking him with long deep strokes. Darrin marveled at Tommy’s resurrection and he clenched his sphincter as hard as he could around the amazing cock deep within him. He clenched and released it with the muscles in his ass in rhythm with the deep thrusts and withdrawals of the splendid cock. Again the rubber band held both of their balls captive as it stretched and released them with renewed vigor.

Tommy continued to fuck Darrin’s ass for nearly twenty minutes as he continued to pleasure his nipples as well. Darrin’s cock had swelled into a huge hard-on and he felt it drip a nearly continuous stream of thick clear pre-cum onto the pillow beneath him. Soon he felt Tommy’s cock throb and swell as before. In a deep thrust, Tommy stopped fucking him and cried out as once again he blasted huge volleys of thick pearly cum deep into his ass. His bowels warmed to the welcomed intrusion of Tommy’s cum. He felt his ass filling with the warm sticky fluid as he gasped with pleasure.

Again Tommy’s cock seemed to soften just a little as its owner groaned with pleasure, still deep inside. Darrin squeezed his own cockhead to prevent cumming to save it for his lovers pleasure when he felt Tommy’s cock stirring again deep inside him. He couldn’t believe that the cock was hardening again, but his asshole told him different. The huge cock stiffened yet a third time and soon was pummeling his ass again with its delicious intrusions and withdrawals. “Oh God, yes!” Darrin gasped as Tommy’s remarkable engine fucked him deeply once more.

Darrin could feel Tommy’s cum leaking from around his cock onto the bed or running down his thigh. Tommy gathered some of his cum from his thigh and wiped it on Darrin’s lips without even missing a beat in his relentless fucking of Darrin’s ass. He licked it into his mouth and swallowed as Tommy offered him another dose of his leaking cum. Darrin consumed that too as he resumed playing with both of their balls held closely by the rubber band. After many minutes of unyielding fucking of his ass, Tommy’s cock exploded a third time with another load of warm satisfying cum that filled Darrin’s ass to the brim.

Darrin’s body slumped on the bed and he lay still as Tommy’s cock spasmed then slowly became flaccid. Tommy lay on Darrin’s back, his breathing labored as he tried to recover. After a few minutes Tommy reached under himself and removed the rubber band holding their balls together. He rolled off Darrin’s back to lie next to him as he struggled to resume normal breathing. Darrin felt cum flowing from his asshole to flow down to coat his balls. It still felt as warm as it did when Tommy’s cock deposited its cum deep in his ass.

“Oh Tommy, I don’t believe what you just did,” Darrin said. “I can’t believe your cock stayed hard enough for you to fuck me three times in a row.”

“Don’t ask me how I did that,” Tommy said, “it seems to always happen.”

“That’s marvelous, Tommy, I’ve never even heard of that being possible.” Tommy didn’t respond as he got up from the bed and walked to the bathroom. Darrin could hear water running for a few seconds then Tommy returned and lay down beside him. Darrin turned over to face him to see him with another superb hard-on. “I don’t believe it.” Darrin stated flatly and reached over to grasp the hard cock in his hand.