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First Time With A Man

Leigh reluctantly loses his anal virginity.

Instead of going straight home, Leigh decided at the last minute to grab a beer at the local watering hole. His shift ran long and he was dog tired, but recuperating at the bar sounded much more pleasant than just plopping down in front of the tv.

Leigh was in his early thirties, tall and cut lean. His muscles were tanned from working outside all day and on this particular evening they still faintly glistened with his sweat. After arriving, he quickly found a seat at the bar and ordered his drink. He checked out the scene - there was a group of three giggling women in the corner booth.

A pair of guys sat at the other end of the bar. And a lone man sat two seats away from him. An old fling was also busy playing pool with someone he didn’t recognize. He resigned himself to his own company and nursed his drink.

“Hey,” said the stranger who sat two seats away from him.

“Hey,” Leigh replied. He looked back at his beer.

“Do you come here often?”

“Do you always use the oldest line in the book?” Leigh shot back.

“I’m just trying to make conversation, mate, no need to be rude.”

“Shit, you’re right. Sorry. Long day. Hey, where are you from anyways, I couldn’t help but notice your accent.”

“Australia. The chicks here throw themselves at me whenever I open my mouth.”

“Well, not me!”

“You sure about that?”

Leigh raised an eyebrow and took a moment to check out this stranger. He was attractive by anyone’s standards. He had short blonde hair, a sharp chin that was covered with three-day-old scruff, and a seemingly strong body. He looked tall and sat up straight. But, Leigh wasn’t into guys. He had kissed a male classmate in high school, but... he pushed that thought away…

“I, I.. I am straight,” Leigh finally said.

“You don’t seem so sure about that.”

Leigh blushed and signalled the bartender for another beer. He quickly threw down the back of his throat and ordered another.

“Woah, if I didn’t know any better, I’d say I’m making you nervous.” The stranger declared.

“Shut up, mate,” Leigh replied, emphasizing the word ‘mate’.

The stranger laughed and turned back to his own drink.

“I’m Leigh. What’s your name anyways?”

“My name is Joe. And I have a room over at the Lodge. Room 219,” He replied as he finished off his cocktail and stood up. “I hope I’ll see you there later.”

Leigh didn’t say another word as Joe walked out of the bar. He did glance up and take a final look at his ass though, just as the door closed behind him.

After finishing another beer alone, Leigh walked to the parking lot. He swayed a little and realized he shouldn’t drive home. Just as he resigned himself to walking, he remembered Joe’s invitation to room 219.

Leigh played with the idea of hooking up with a stranger - a man, no less - and felt turned on. It intrigued him as much as it disgusted him. He wasn’t gay. He rarely found men attractive. But there was something about Joe, the way he was so sure that Leigh was going to come knocking on his door that pulled Leigh to the Lodge like a magnet.

Five minutes later he found himself outside of room 219. Before he could talk himself out of it, he knocked.  

After thirty seconds, it became obvious that no one was there. Or that he was being ignored. Leigh cursed under his breath for being so stupid and turned around to walk away. That’s when he saw Joe walking towards the room, ice bucket in hand and shirt off.

“I knew you’d come a-knocking,” Joe said in his funny accent. “And I’m glad you did. I hope you haven’t lost your nerve.”

He then slid past Leigh and opened the door and went inside without looking to see if he was being followed.

“Well, are you coming?” Leigh heard Joe call from inside. “Don’t want to let all of the bugs in!”

Leigh was tongue-tied. And nervous. He thought about making a run for it, but, instead, he reluctantly went inside and closed the door behind him.

“I’ve.. I’ve never done anything like this.”

“That’s okay. I have. Trust me. You’ll love it. Here, have a drink. It will help.”

Joe poured Leigh a glass of whiskey on ice. It burned Leigh’s throat but he was grateful for a drink that would make his head spin and push him over the edge. His palms were getting sweaty and his cock stirred in his pants.

Without saying anything, Joe sat on the bed next to Leigh and turned on the television with the remote. He and promptly put on some pay-per-view porn - two guys and one girl. Leigh relaxed a bit and let himself get lost in the scene in front of him. His penis started to get hard and he instinctively went to rub it over his jeans.

“Listen, mate. We don’t have to do anything you don’t want to do. But... I would sure love to see that cock of yours,” Joe explained.

Leigh looked right into Joe’s eyes and decided right then and there that he would do whatever this man said tonight. He pulled down his pants and kicked them to the side. He took out his semi-hard dick from his boxers and started to stroke it softly.

Joe watched for a minute and then he got down on his knees in front of Leigh. When he put Leigh’s cock in his mouth, Leigh initially tensed before realizing that Joe was an expert at sucking dick. Never had a woman given him a blowie like this - Joe was swallowing him whole and enjoying every minute of it. He didn’t even gag, even though Leigh was equipped with a seven-inch shaft.

Joe continued to lick and suck on his member, playing with his balls and taint ever so softly. Leigh felt like he was going to blow at any second. Joe pulled Leigh’s legs to the very edge of the bed and he started to slide his free hand up his thighs, around his butt, before he reached his tight virgin star. He tickled the entrance there, before bringing his finger back to his mouth, sucking on it, and then, just as quickly he pushed it back inside of him, right up to the knuckle.

Leigh let out a soft groan. He had never felt this turned on before. How was a man doing this to him?

Leigh laid back down on the bed so Joe would have better access to his privates. Joe took this opportunity to start licking his asshole. It felt sensational! As Joe’s tongue probed his asshole, Leigh was sure he was going to explode, so he tried to think of the least sexy things he could think of. His thoughts were no match for Joe’s tongue though, and as he started fucking his firm hole with his tongue, Leigh couldn’t help but scream…

“I’m cumming, oh God, I’m cumming!!”

He shot a hot load onto his chest. Joe peeked up from in between his legs and gave him a nasty grin before he started to lap up all of the warm cum from Leigh’s hard and smooth stomach.

“That. Was. So. Fucking. Hot!” Leigh said, out of breath and fully relaxed.

“I thought you’d like that. And there is plenty more where that came from. Now, on your hands and knees.”

Leigh was nervous about this part, but he was still so turned on he didn’t really think about what was going to come next. He heard Joe strip down his pants and pull down his underwear, before going to the nightstand where he grabbed a giant bottle of lube and a pack of condoms.

“I’m not sure, Joe. I’ve never had anything in my ass before.”

Joe laughed and smacked his ass hard. “You’re gonna love being my little cum bucket, tonight.” And then he put his face in between his cheeks and started giving him another rim job.

Leigh relaxed again, especially as Joe’s tongue felt so warm and soft on his hole. After a few minutes, Joe grabbed the bottle of lube and put it directly on his star. Then, he pushed in a finger deep inside of Leigh. Leigh let out a soft mewl.

After pulling it in and out for a minute, Joe put in another finger and Leigh was surprised at how turned on he felt and how good it felt having something foreign in his ass. Joe kept working the tight hole with his fingers, stretching and stretching it so it could eventually take his mightily thick cock.

“Relax, Leigh. Relax,” he said as he gave him a swift spank on the bottom.

Leigh tried to go to a tranquil part in his head - but it was hard to concentrate when his virgin hole was getting finger fucked for the first time by an Australian stud. He realized that his own penis was hard again and that all he wanted was for this man to impale him with his cock.  

“Fuck me, Joe. God, please, fuck me now.”

Joe didn’t think Leigh’s ass was ready for him, but he was horny as hell and wanted to teach this so-called-straight boy a lesson in ass fucking. He pulled his fingers away and admired how Leigh’s ass was slightly gaping. It made his cock twitch with pleasure when he thought how stretched this little hole would soon be. Joe slipped on a condom and poured more lube onto Leigh’s ass and on his own dong. He lined it up against the rim of Leigh’s asshole.

Leigh gasped as he felt the mixture of pain and pleasure as Joe pushed into him. For a second he started to panic, thinking that he would never be able to take Joe’s entire dick into his ass - for God sakes, he didn’t even catch a glimpse of it to know how big it was!

It was a big cock. Joe’s uncircumcised wang was six inches long, hard as steel, and monstrously thick. Joe slowly pushed it further into Leigh’s rosebud. Eventually, he got past the rim. Leigh let out a scream, so Joe stopped, waiting for him to urge him on further.

“It hurts too much, please, stop... I can’t do this.”

“Shhh, relax. Loosen your muscles. It’s going to feel great, I promise.”

It took him a minute, but Leigh eventually started to calm down a bit. Stroking his cock helped.

Joe started to push further and further into him. Finally, his entire shaft was in Leigh’s virgin hole and his balls were pressing firmly up against him. Joe started to pull out again, pouring more lube on both of them. Leigh winced in pain but Joe began to grind up against him in earnest, ignoring the protests coming from Leigh’s mouth. Eventually, they were both moaning in pleasure.

When he realized how much Leigh was enjoying this assault, Joe really started to fuck his tight little hole. Ramming into him again and again, his balls slapped up against Leigh’s taint. He reached forward and started to jack him off while he found himself closer and closer to orgasm. Eventually, Joe put his hands back on Leigh’s hips to steady himself and he bucked against him quickly.

“Oh yeah, fuck me! Fuck me harder!” Leigh urged. “Fill my ass!”

Joe continued to plough into him. Leigh’s ass muscles were milking his dick. It felt so good - being inside such a warm and tight hole. It also felt powerful, knowing that he seduced a man who claimed to be straight, a man who was reluctant to this entire experience just an hour before. Now, he owned this man’s ass.

Joe pumped for a few more seconds but this realization, combined with Leigh’s moans and his obvious pleasure from having his ass claimed by another, caused Joe to release his load. He allowed his dick to go a bit softer before he slowly pulled it out of Leigh. He flung the condom in the bin as he admired how Leigh’s previously tight star was now gaping and used before him.

Joe collapsed on the bed beside Leigh.

“That was fantastic!” Leigh exclaimed. “God, I have never felt so full. Is it always like that?”

“Oh, it gets better. You just wait... I am going to be playing with you all night.”

“Just give me five more minutes…”

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