Trying Something New

Story Info
A straight man’s fantasy leads to sexy, man-on-man fun.
6.6k words
4.7
30.6k
49

Part 1 of the 5 part series

Updated 12/23/2023
Created 09/10/2023
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Darren, 36, was on his couch and casually looking at various porn galleries on his phone. Wearing only a white tee shirt, he scrolled through the pictures with one hand while his other hand was rubbing his cock.

As he opened a new gallery, he was excited to see a sexy, large-breasted woman on her knees, sucking off a group of horny men.

"Lucky whore." He thought to himself. "Look at those beautiful dicks."

These thoughts hadn't always been the norm, but they had become much more frequent lately.

Darren had always identified as straight, and still did, but his curiosity about the male body had been triggered several years prior. Almost ten years prior. Although he had never acted on these curiosities, he had noticed that brief moments of homosexual fantasies would creep into his mind when he was looking at porn.

What triggered his curiosity all those years ago was a night in which he was hanging out with two good friends: Jeff and Josh. They were both the same age as Darren. Josh had been Darren's best friend since high school and was also straight. Darren met Jeff while working a part-time job in a grocery store.

From day one, there was no mistake about Jeff's sexual orientation. He was gay and proud of it. Almost as if he wanted to make sure the world was certain of it. Jeff would constantly make dirty comments to customers and coworkers. There were several times he would point out customers to Darren and mention that he had sucked them off, or made love to them anally.

Back in those days, the three of them would hang out together and smoke weed. On that particular night, they were at Jeff's waiting to hear from their source to buy more. They had just finished smoking their last joint and it was taking longer to hear back on getting more, so they were starting to get bored.

Josh joking had asked Jeff if he had any porn to look at while they waited. Jeff didn't miss a beat, grabbing his stack of gay porn magazines and proudly offering them to his friends. They all chuckled, but then Josh went ahead and picked up one of the magazines.

Darren wasn't sure what to do, but decided if his best friend was okay with checking it out, he should too. He slowly grabbed a magazine and then Jeff did the same.

"It won't hurt to have a look." Darren thought to himself.

As he began looking through the magazine, he was surprised at his lack of apprehension. There was no feeling of weirdness as he paged through the pictures of various men. It was a genuine curiosity.

The first picture that caught Darren's attention was a man in the process of undressing, his pants lowered to reveal a rather phenomenal buttocks. Darren had always been an ass man, preferring a girl with a nice butt over a girl with large breasts. Apparently, he was now able to acknowledge that he could find a man's ass attractive as well.

"I wouldn't mind putting my face right in that crack." Darren thought, before realizing he was thinking that about another man.

He turned the page and continued to study the various naked men. He was noticing that his manhood would occasionally twitch as he looked at more pictures, but he tried to ignore it.

The next picture that made Darren pause was a close-up of one man bent over with another man's thick, hard penis buried deep inside of his anus. As Darren took in the view, he felt his dick twitch again. He glanced up to make sure his friends didn't notice, but they were busy looking at their own magazines.

Continuing through the magazine, Darren observed several more tone, well-hung, muscular men. The last picture he stopped on was another close-up, but more simple. This picture was simply a solo male, with his jeans pulled down and the focus of the picture was clear: the man's semi-erect penis, accompanied by two plump testicles.

Darren couldn't seem to look away. He was fascinated. As he stared at the cock, there was no denying the blood rushing to his genitals. The dick he was looking at wasn't the only one that was now semi-erect. Darren started to get nervous.

"Shit. What if they notice I'm getting a boner?!" Darren wondered. "Knowing Jeff, he'd probably offer to blow me. Josh would never let me live down getting turned on by gay porn."

As Darren ran through scenarios and came up with excuses in his head, he was saved by Josh's phone vibrating. It was there weed source, letting them know they could swing by. With a deep breath of relief, Darren closed the magazine and set it aside, avoiding an awkward situation.

Later that same night, when he was back home and alone, Darren couldn't help but remember being turned on by the magazine. He grabbed his phone and Googled "big white cock". He quickly found an image that caught his fancy and began stroking himself, achieving orgasm within just over a minute. It was one of the largest ejaculations he could remember.

"Did I really just jerk off to a cock?" Darren asked himself, fully aware of the answer.

He closed out the browser on his phone, smoked some weed, and went to sleep.

Ever since that night, Darren would occasionally have thoughts about how things might have turned out differently if Josh hadn't heard back from their dealer. Would they have teased Darren? Were they perhaps getting aroused as well looking at naked men having sex? What if they would have all gotten undressed and fooled around? Darren would never know.

The three of them were still friends and would hang out at times, but it was much less frequent as adult responsibilities increased as they got older.

So now, as Darren stroked his erection, those familiar thoughts once more crept into his mind. The only difference this time is that he pulled up his phone contacts and scrolled to the J's. His heart skipped a beat as he paused on Jeff's name.

"Should I finally do it?" He wondered. "Should I finally tell him it turned me on to look at those dicks all those years ago?"

Just the idea was thrilling to him, but also made him nervous. What if Jeff didn't react the way Darren imagined he might? But then... what if he did?

"Fuck it." Darren said, tapping Jeff's name.

Darren continued to grip his shaft as he held the phone and listened to it ring. It felt like it was ringing forever.

"What's up?" Jeff asked, answering the phone.

"Not much." Darren answered. "Just seeing what you were up to."

"Trying to find some dick to suck, but everyone is busy." Jeff told him with a laugh. "I don't suppose you'd like to donate yourself to the cause?"

Darren's eyes rolled back as he stroked his erection, briefly contemplating Jeff's offer. On the one hand, Jeff was joking. On the other hand, if he agreed then Jeff would absolutely make good on the offer.

"Maybe one of these days, man." Darren joked back.

"Such a cock tease."

"Actually that does remind me of something I wanted to talk to you about."

There was a brief pause, which gave Darren a moment of panic.

"You called to talk to me about finally sucking you off?" Jeff asked jokingly.

"Not exactly." Darren replied anxiously. "But I've had something I've wanted to tell you, but just never had the courage."

"Please tell me you're coming out of the closet." Jeff said.

Darren laughed, his cock twitching in his hand at the brazen suggestion.

"Nope. Still straight." Darren informed him. "But if I tell you something, you have to promise me you won't tell anyone."

"What's up?"

"Well... do you remember that night a long time ago when Josh and I were hanging out? And we all started looking through your porn while we waited on the dealer?"

"Of course I remember!" Jeff said. "My two so-called straight friends looking at my porn stash."

"There's something I've never told you. Or anyone." Darren added, continuing to try and slowly stroke the nerves and anxiety out of his erection. "Truth be told... I kind of got turned on. Like, really turned on."

"Hell yeah. That's awesome!"

"If we didn't get that call, I was on the verge of having a full-on boner." Darren continued. "I even jerked off to a picture of a cock later that night when I got home."

"Welcome to the club." Jeff told him jokingly.

Darren laughed as he squeezed his shaft. Finally making his confession was only making him more turned on.

"So like I said, I'm straight." Darren said. "But when I look at porn now, I sometimes have gay thoughts and fantasies. Like imagining I'm in the girl's place, sucking a fat dick. I can't explain why, but it just turns me on sometimes."

"Sounds like you're at least a little curious."

"Maybe." Darren admitted. "It seems to be happening more often now. It's pretty much anytime I jerk off, I have at least one moment of thinking about another dick being there."

"Makes sense. That night was what, a decade ago? So you've been letting these lovely, gay desires build up this whole time." Jeff explained. "When was the last time?"

"A few minutes before I called you."

They both laughed.

"Okay. So did you finish? Did you come thinking about a big, sexy penis?"

"I actually haven't finished yet." Darren admitted.

"Wait wait wait. Are you jerking off right now?!"

Darren took a deep breath.

"Yeah." He added in a soft, shy tone. "Sorry."

"Don't apologize. That's fucking hot and kinky." Jeff told him. "Calling up your gay friend to tell him you jerk off to gay stuff, while stroking your penis. I love it! Maybe you should come over and let me finish you off?"

"Ha." Was the best Darren could offer. "I don't know if I can do that."

"Why not? You've been fighting these urges for ten years. You owe it to yourself to give it a try." Jeff suggested. "I promise I give excellent head."

Darren's mind raced as he briefly considered the idea of experimenting with his friend. He was certainly horny enough at that moment to give in, but his nerves were still winning the fight.

"I don't know..."

"I promise we can go at your pace. I'm not going to force you to strip and bend you over." Jeff explained. "If you just want to talk, we can talk. If you want to fool around a little bit, I can be your source of exploring yourself and these lovely urges you've been having."

"It has been a while since we've hung out." Darren noted. "But I'm not sure I'm ready to go through with it yet."

"No time like the present. You've denied yourself for far too long as it is." Jeff told him. "How about this? If I can get you to cum on the phone, you agree to hang out this afternoon?"

Darren couldn't believe he was contemplating this. The confession had really made things much more real.

"Fine."

"Perfect." Jeff said. "Now lean back, close your eyes, and play with your cock while you listen to me."

Darren closed his eyes and began giving his shaft slow but full length strokes.

"Imagine I'm right there with you as you play with yourself. Imagine I'm telling you how sexy your penis looks with your hand wrapped around it." Jeff told him. "Imagine I take off my pants and show you my 7.5 inch dick and how turned on you've made it. You keep stroking as I walk up beside you, casually brushing the head of my cock against your cheek."

Darren's breathing got heavier as he pumped his shaft.

"I run my fingers through your hair as my erection makes contact again." Jeff continued. "This time brushing against your lips."

Darren could tell he was getting close, most likely because he had already been fondling himself for so long.

"Unable to fight your curiosity, your mouth barely opens." Jeff told him. "Your tongue is shy, but it extends just enough to swipe along the tip of my cock. It is rewarded with the taste of precum."

With a sudden moan, Darren felt himself erupt in a powerful orgasm. Several large ropes of cum landed on his shirt and chest. Darren took a few more breaths as he recovered from his ejaculation.

"Fuck."

"Was that it? Did you nut already?"

"Yeah." Darren said. "Probably because I was edging before I called you."

"Wow. I didn't even get to anything like me sucking your cock, or rubbing our dicks together." Jeff added. "I'm impressed."

"I made quite a mess of my shirt." Darren said. "I suppose I should get cleaned up."

"Sounds good. I'll see you this afternoon."

"You were serious about that?" Darren asked.

"Dead serious." Jeff told him. "But don't be nervous. I won't make you do anything you don't want to do."

The friends said their goodbyes and Darren hung up the phone. Darren took a moment to realize what had just transpired. He had finally told his friend about his gay fantasies and then masturbated over the phone. And now he had agreed to go over to Jeff's place that afternoon.

***

Darren took a deep breath as he stood in front of Jeff's door. He hesitated briefly and then gave it a knock.

Jeff promptly opened the door, welcoming Darren inside. Darren noticed Jeff was wearing shorts and a tee shirt.

"Given his personality, I'm shocked he isn't completely naked." Darren thought to himself.

Jeff led Darren down the hallway and into the kitchen. Darren could feel his nerves getting worked up again as the reality of why he was there kicked in.

Once in the kitchen, Jeff grabbed a bottle of red wine and two glasses.

"Care for some liquid courage?"

"Are you just trying to get me drunk so you can try to fuck me?" Darren jokingly asked.

"That's just one part of the plan!" Jeff joked back.

Jeff filled the glasses and set one in front of Darren, who took a sip to try and calm his nerves.

"You're free to take off your pants whenever you're ready."

Darren laughed nervously, taking another sip of wine.

"There's the Jeff I know." Darren said. "I think I'll work on this wine first and see where things go."

Jeff took a gulp of his wine as he winked at his friend.

"In all seriousness though, why did you wait so long to tell me about your gay fantasies?" Jeff asked.

"I don't know. I still consider myself straight, like I said." Darren responded, taking another sip of wine. "It's just sometimes I have the urge to suck a cock."

"There's nothing wrong with that. And whatever does or doesn't happen here today, it doesn't make you gay or any less straight." Jeff explained. "Getting a blowjob doesn't make you gay. Giving a blowjob doesn't make you gay. Fucking someone in the ass doesn't make you gay. Getting fucked in your ass doesn't make you gay."

Darren nodded in agreement, once more taking a sip of wine. Jeff's words, and the wine, were beginning to help calm Darren's shyness. The candid conversation, however, was beginning to impact Darren's arousal.

"Besides, you wouldn't be the first straight guy I've had sex with." Jeff continued. "Far from it."

"Really?"

"Oh yeah. You'd be surprised how many straight guys have similar fantasies. It's pretty easy to talk them into at least getting some head." Jeff said. "Especially married guys. After a few years their wife stops going down on them and they're more than happy to let me suck them off."

"Wow." Darren said, feeling his manhood twitch. "That actually sounds hot."

"It's very hot." Jeff agreed.

They both paused, consuming more wine. Jeff grabbed the bottle again.

"Let me top you off." Jeff said, refilling both of their glasses. "There's something in the living room I want to show you."

The two friends made their way to the living room. Darren took a seat on the couch and Jeff took a seat right beside him. Darren noticed what Jeff wanted him to see: all of those same, gay porn magazines were on the coffee table. There were also three freshly rolled joints next to them.

"I remember we were high that night." Jeff said, picking up one of the joints and lighting it. "Do the magazines look familiar?"

Darren took a sip of wine, his mind starting to race as he looked at the porn.

"Of course they look familiar." Darren admitted, reaching out and grabbing one. "This was the one. This is the one I was looking at that night."

"Go ahead and have another look." Jeff suggested, taking a drag off the joint and passing it to Darren. "I'm curious which specific pictures got you all hot and bothered."

Darren took a long puff from the joint, handing it back to his friend. He then began paging through the magazine as he had so many years ago. Jeff put his arm around Darren's back, looking at the pictures over his shoulder.

They shared the joint together as Darren slowly made his way through the magazine. He took his time to examine each set of pictures, not worrying about the excitement growing in his jeans. He turned the page and paused.

"Here's one." Darren said, showing Jeff the close-up of a cock buried in another man's ass.

Jeff handed Darren the joint for a final puff, before putting it out.

"Mmm. Nice." Jeff told him. "Imagine how great that must feel for him. Bent over with a big dick deep inside of his ass. Stretching him out like that."

Darren continued through the magazine. He took a sip of wine as he turned the page and stopped once more. There it was, the close-up of the man with his pants down and his semi-erect penis on display.

"This was the one." Darren said. "This is where I had to put the magazine down because staring at this picture was causing me to get really horny."

"Awesome. That's a pretty sweet dick." Jeff encouraged. "Why do you think it turned you on so much?"

"I don't know. There's just something mesmerizing about it." Darren admitted, the wine and the weed having lowered his inhibitions. "It makes me wonder what it would feel like to feel it and just inspect it. Would it continue to get erect if I held it in my hand? If it did get hard, would I want to play with it? Offer to put it in my mouth?"

"That's really cool." Jeff told him. "Is it happening again? Are you getting turned on by his penis?"

"Oh yeah." Darren said. "I'm getting pretty hard."

"Me too!" Jeff added. "Would you like to take off your pants? I'd love to see how hard you are."

Darren blushed.

"I don't know if I'm quite ready for that yet. I'm sorry."

"No need to apologize!" Jeff assured him. "I'm happy to go at your speed. Whatever you're comfortable with."

They each took another sip of their wine.

"Would it bother you if I took off my shorts?" Jeff asked. "Would that make you uncomfortable?"

"Not at all. Go for it!"

Darren continued to look through the magazine as Jeff stood up facing the other direction. He discarded his shirt first. He then unbuttoned and unzipped his shorts, dropping them to the floor.

Darren couldn't help but glance at Jeff. A lack of underwear left Jeff's backside exposed, and Darren couldn't help but admire his friend's buttocks. Jeff, now completely naked, sat back down right next to his friend, unashamed of his fully erect penis sticking up in the air.

Darren did his best to focus on the gay porn, but he couldn't help but be distracted, stealing quick glimpses of Jeff's cock.

"It's okay to look at it."

Turning his head, Darren took the opportunity to get a good, long look at the rock hard dick. It had a great shape, with a well-defined tip. Jeff smiled as he watched Darren's curiosity and facial expressions.

"You're welcome to touch it, too."

"I don't know, man." Darren protested.

Despite his hesitance, Darren could not deny that he was throbbing in his jeans as he admired the penis. Jeff took Darren's hand in his own, resting them on his bare thigh.

"It's okay to explore." Jeff told him. "Embrace your desires. Don't be afraid of the cock."

Jeff slowly guided his hand further, until it was over his lap. He then placed Darren's hand directly on his penis, and pulled his hand away. Darren tentatively wrapped his fingers around the base, essentially holding his friend's penis.

"See? Nothing to be scared of." Jeff said. "What do you think? Do you like it?"

12