tagGay MaleTony's First Time

Tony's First Time


Tony had a crush on this guy at work. Mark was a confident, dominant, and out bisexual guy. He had carefully tousled black hair above blue eyes. The girls at the office fawned over him, and he'd been with many of them. The gay guys at the office were jealous of him because he was so fit without having to work out. He'd been with many of them, too. Tony was closeted and fantasized about Mark all the time, but he couldn't bring himself to do more than make small talk with him.

One day at the copier, Mark mentioned he was tired because he spent all night at the 501. "That's a great place," he said. "Have you ever been?"

Tony blushed, knowing that to admit he'd been to the gay fetish bar would be admitting that he was gay, or at least curious. But he assumed that Mark already knew, so to deny it would be a shy step back into the closet. "Once or twice," he mumbled.

"You have? You should hit me up next time and we can go together." Mark gave him a pat on the back that was much too close to his rear end. Extremely flustered now, Tony grabbed his copies and pointed himself toward his desk. "Sure," he said, scurrying away.

It was Friday after Tony's embarrassing run-in with Mark, and Tony was looking forward to going home and relaxing in front of the TV. Maybe he would search on Craigslist's Casual Encounters and imagine meeting one of those guys for a night. It was always a fun segue into watching porn, where he imagined one of the guys being real and there for him.

Someone called his name, and he turned to see Mark standing at his desk. Tony was seated, and couldn't help stealing a glance at the bulge in Mark's pants before meeting his eyes. "Tony, some friends and I are going out for drinks tonight. Want to come?"

Tony swallowed, thinking of the possibilities. They could have a few drinks, maybe have a rendezvous the bathroom—but he mentioned friends. Surely there would be other guys vying for Mark's attention as well. Tony sighed. Well, at least he could be among the admirers. "Sure, sounds like fun."

And he did end up having fun, despite the crowd. Some of the men he knew well enough from work to discuss some projects or common interests. After an hour and a few drinks, Tony was able to stop worrying about his secret love. The after party was at Mark's house, and he was a great host and bartender. Tony knew he was drinking a little too much, but he could always call a cab if he needed to. Eventually things started winding down, but just as Tony started judging his sobriety, Mark called him over.

"I heard you speak some Russian," he said.

"Yes, I studied it in college." Mark waved him toward the bar and pulled a beer mug from his collection.

"This one has Russian on it, right? What's the alphabet?"

"Cyrillic." Behind him, Tony heard some of the others saying their farewells, and Mark waved to them.

"What's it say?"

"It says Baltika. That's one of the big beer companies in Russia. And there's a quote on it: 'A glass for the vodka, a mug for the beer, and good company for the table.'"

"Cool! We know about good company, don't we?" Mark gave him a beautiful smile. Tony blushed and turned away to hide it. Looking around the room, he realized it was empty. Tony's mouth suddenly felt dry.

"It must be late," he said. "I should get going."

"Why don't you stay a little longer?" Mark's hand stayed firmly on his should as he rounded the bar. "We didn't get to talk much tonight."

"No, but that's ok. You're the host and all." He felt his stomach tingle as Mark guided him to the couch and sat him down. He let go of his shoulders, but their thighs were still touching. Tony directed his eyes to his feet so he wouldn't see the mischievous look in Mark's eyes. Maybe he just wanted to talk more about Russia.

"I've always wondered about you," Mark said as he stretched his arms and leaned back on the couch. His right arm was tantalizingly close to Tony's neck. What would it feel like to have his hands in his hair or giving him a neck rub? Tony exhaled and tried to focus on what he was saying. "Not much into the scene?"

"Well, not really. Not really out, especially not at work."

"Oh, I understand about work, but what about having fun? Hanging out? Hooking up?"

Might as well just admit it, Tony thought. "Well, I haven't really done anything with a guy before." He forced himself to look up. Mark's eyes were not just mischievous, but lustful. Tony felt his cock twitch a little. "I'm kind of shy."

"I could tell." Mark started rubbing his back in slow, heavy circles. "Never took the plunge? Pun intended." Tony shook his head, feeling himself getting more aroused. There was no doubt about where this was going. Mark said in a lower voice, "Maybe I should fix that."

Tony could only nod his head, lost in those eyes. Mark leaned toward him and gave him a simple but insistent kiss. He grabbed Tony's hand and put it on his cock, rigid under his pants. Tony felt a wave of heat going up his arm, through his chest, down to his own hardness and up to lips. Mark's mouth was the sweetest thing he had ever tasted, completely different from anything he'd ever felt with the unfortunate women he'd experimented with. It was sweaty, salty, and hairy. Tony loved it.

Mark broke away to take off his shirt and slide off his pants. Tony admired his muscular chest and arms. He was more hairy than the porn he had watched, but still very sexy. And his cock. What a beautiful piece of art. Long, straight, thick, bulging with veins. Better than anything he had seen on the Internet. He looked up at Mark again, who was leaning back and watching him expectantly. Tony cautiously reached his hand toward the cock. No surprises when he touched it: a head, shaft, hairy base, and a ball sac. He looked back at Mark, who had closed his eyes in anticipation. Shaking with excitement, Tony knelt between his knees and rubbed it some more. Mark sighed, and Tony decided to take the plunge.

He placed the tip in his mouth, then slid his tongue underneath. It tasted slightly salty and musky. He pushed his mouth further down and got another sigh from Mark. Things seemed to be going well. He pushed the cock as far back in his mouth as it could go. When it touched the back of his throat, he almost gagged, and he pulled back. He tried again, this time closing his lips around the shaft. The member jumped and thickened. Encouraged, Tony started sliding his mouth up and down in a familiar rhythm. Mark pumped his hips to meet him. The fact that he was bringing so much pleasure to another man aroused Tony, and he started to stroke his own hard cock. Tony didn't want to come up for air. He didn't know what to do with all the spit, though. He pulled back, swallowed, and asked, "How's that?"

"A good start," Mark said, pushing his head down again. Tony resumed with gusto, guided by Mark's hands on the back of his neck. Before long his mouth was aching, filled with spit and precum, but it tasted so good he didn't want to stop. Mark had other plans in mind. "I'm going to fuck you now," he said, pushing him away and standing up. "Take of your clothes."

Tony was too horny not to obey. He stripped off his shirt and pants while Mark got some lube from a side table. Mark pushed on his shoulders so he was on his knees in front of the couch. He ran his hands down Tony's back, and Tony shivered. When he reached his ass and his tight hole, Tony started to breathe quicker. He had watched a lot of porn of guys getting drilled by huge cocks, but he had never put anything more than a few fingers in there. That's what Mark started with, lightly playing around the rim, then slowly entering him with two fingers. Tony immediately clenched up and was lightly admonished by Mark.

"Relax." Tony exhaled, and the two fingers continued exploring on the other side of the tight hole. They exited and then reemerged, covered in cold lube. Tony liked the sensations as they massaged and stretched his insides. Then the fingers left for good, and a larger mass poised itself at his entrance. Tony tried to breathe, but nothing could prepare him for the abrupt breaking of his seal as the tip passed through. Mark let it rest there for a second, then slowly pushed his way inside. Tony felt a stretching pain that made him moan, and it was all he could do not to pull away. He arched his back, and Mark steadied him with his hands. The pain continued as the cock went deeper, and eventually Tony felt a tingling of pleasure behind it. He moaned again, pushing his hips back to meet Mark's body.

The cock was now completely in his ass, and Mark paused while Tony got used to the fullness. Then he started sliding in and out with slow, shallow thrusts. Tony enjoyed the feel of Mark's body pressing against him, the wet stretching inside him, and the pressure building in his own balls. Mark quickened his pace and started to come all the way out, and Tony savored the cold emptiness followed by painful fullness. He grabbed his cock and started pumping in time, pulling back his head and closing his eyes.

"Do you like getting fucked?" Mark asked him.

"Oh God, yes," Tony said.

"Tell me you like me fucking your ass."

"I like it! I like you fucking my ass," Mark continued slamming into him at a wild pace. Tony felt delirious in a mixture of pain and pleasure, and he knew he was going to come soon. "Please, please fuck me. Oh God!" As he reached the point of no return, he felt Mark groan, and streams of warm fluid started to fill his ass. It sent Tony over the edge, and he frantically pumped his own cock until it was empty. Mark stayed inside for a few blissful minutes, then left Tony empty and weak.

"Might make a mess when you stand up," Mark said, slapping his back. Tony was content to lay his head on the couch until Mark returned with a towel. When he stood up, feeling the slimy remnants of their activity running down his leg made him shiver. A secondary wave of embarrassment flooded him as he looked over at Mark, who was now at the bar fixing a drink.

"I guess I'll go...clean....up..." He staggered toward the bathroom and washed himself off. He felt tired, drunk, and happy. His senses were returning by the time he got dressed. Mark was reclining on the same couch, drinking calmly.

"Do you want some water or something?" He asked, as if they were back to a few hours before.

Tony shook his head. "I gotta....I guess I'll go." He felt conflicted, not sure if he wanted to stay and converse. He was afraid the bubble would break and he would be back to his old self, closeted and lonely.

"Ok man." Mark was just as casual as ever. He winked at him. "Give me a call tomorrow. Good night." Tony smiled and nodded. He felt like whistling as he left the house. When he got in his car, the soreness reminded him of exactly how good the night had been.

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