A gay story: Trying Something New 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?”
“It’s different, but in a good way. Hard and soft at the same time.” Darren admitted. “And it’s so warm.”
Jeff laughed.
“That’s because of all the blood rushing there.” He said. “You seem to be getting quite the bulge in your jeans. I’d love to get a look at yours.”
“I think I’m ready to get naked, but…” Darren started. “…everything today has been kind of a whirlwind. Before I came over I didn’t get the chance to do any… ya know… prep.”
“Would you feel better if you took a shower?”
“Probably.”
“Then let’s head to my bathroom.” Jeff suggested. “I don’t mind if you wash up.”
Darren released his grip on Jeff’s shaft. They both finished off their wine and headed to the bathroom. As they entered, Darren was surprised to see that Jeff also had a luxurious jacuzzi tub.
“Damn that’s a nice bathtub.” Darren said.
“You’re welcome to take a bath if you’d rather. And there’s plenty of room.” Jeff offered. “I could join you if you’d like some company.”
Darren blushed, throbbing again at the suggestion.
“Some company might be nice.”
“Fabulous!”
Jeff walked to the tub and started to get the water running, giving Darren the chance to check out his ass once more. Then he turned around and knelt down in front of Darren.
“Time to finally get you out of these clothes!” Jeff announced.
Darren didn’t fight it, taking off his shirt. Jeff unbutton and unzipped Darren’s jeans, tugging them down. The boxers beneath didn’t offer much resistance to Darren’s erection. Jeff grabbed the boxers and tugged them down, finally freeing Darren’s genitals.
Jeff helped Darren out of his pants and underwear and set them aside. Getting back to his feet, they now stood facing each other, completely nude.
“You have a nice penis.” Jeff said.
“Thanks.”
Jeff briefly took Darren’s hand once more.
“Remember. Don’t be scared.” Jeff told him. “We’re just two horny, naked friends taking a bath together. There’s nothing weird about that.”
“Shall we?”
“After you.”
Jeff helped Darren step into the tub, also offering a supportive hand on Darren’s ass. Darren then made way for Jeff to step into the tub. They both eased themselves down into the warm water, facing each other.
“This tub is amazing.” Darren reiterated.
“You are more than welcome to come over any time and use it.” Jeff replied. “Although I prefer if you do so when I’m here.”
“So you can pull down my pants for me and look at my cock?” Darren joked.
“I might want to look at your balls, too.” Jeff teased. “Or maybe that ass.”
Darren blushed as he flirted with Jeff.
“Speaking of your ass…” Jeff said, reaching for some body wash. “…would you like me to help get you nice and clean?”
“Sure.”
Darren shifted around and stood up in front of Jeff, exposing his ass. Jeff squirted some body wash into his hand and started to get it lathered up.
“Cute butt.” Jeff pointed out. “Have you ever tried exploring yourself back there?”
“A little bit.” Darren said as he felt Jeff’s soapy hands on his cheeks. “I had the most success with some anal beads. And an occasional plug can be fun. I bought a dildo once, but for the life of me I couldn’t even get the tip of it inside. I swear I have an abnormally tight asshole or something.”
Darren felt Jeff push his buns apart, obviously taking a look for himself.
“Looks normal to me.” Jeff informed him. “We’ll get that hole opened up properly. I promise you that much.”
Again Darren’s cock throbbed as he felt Jeff’s hands washing his backside, and now hearing Jeff basically confirming that anal sex was on the menu.
“Does this feel okay?”
“It feels really nice.” Darren confirmed.
Darren felt Jeff’s soapy fingers washing up and down his ass crack, occasionally paying specific attention to his special entrance. Jeff even went so far as to pop his fingertip into Darren’s anus briefly before his hands made another pass over Darren’s cheeks.
“Alright. All clear back here.” Jeff announced. “Let’s wash the front now.”
“Really?”
“Absolutely.”
Darren slowly turned to face Jeff, his penis fully erect. Jeff smiled when he saw the dick, squirting more body wash into his hands.
“I guess you really did enjoy having me wash your little bottom.” Jeff teased.
“In all honesty, yes it felt nice having your hands caressing my bare ass.” Darren admitted. “But I also think part of me being turned on is that I’m finally trying something new. Something I’ve thought about for so long but never had the courage to do.”
“That makes sense.”
Jeff’s soapy hands found Darren’s inner thighs first, slowly washing their way up to the pubic area. Darren gasped when he felt Jeff softly begin to soap and fondle his balls. It wasn’t long after that and Jeff was soaping up the length of Darren’s cock. It almost felt like Jeff was giving him a slow handjob.
“Don’t blow your load just yet.” Jeff told him.
“If I do, it’s your own fault.” Darren replied. “Stroking me like that, I’m liable to spray you in the face.”
Jeff chuckled as he continued to delicately wash his friend’s penis.
“Okay I think we’re set.” Jeff said. “Rinse off and I’ll take a closer look to be sure.”
Jeff rinsed his hands in the bath water as Darren squatted down, rinsing himself off below the waist. He then stood back up, Jeff’s eyes never breaking away from Darren’s dick.
“Oh yeah. That’s one clean penis!” Jeff said with a laugh. “I do have a request though.”
“What’s that?”
“I would like to suck your dick.” Jeff added bluntly. “Would that be okay? If I put your cock in my mouth?”
Darren took a deep breath. It was time to make a decision and his erection was telling him it was time to give in.
“Go for it, dude.”
“Lovely!” Jeff said, taking the base of Darren’s manhood in one hand.
Jeff began by kissing the tip of Darren’s cock, followed by his tongue licking and teasing his dickhole. Opening his mouth, Jeff wrapped his lips around the head of Darren’s dick. Darren moaned as Jeff’s tongue swirled all over the tip.
“Fuck that feels really good.”
Jeff’s free hand moved between Darren’s legs. His middle finger slid between Darren’s buns, quickly finding his anus and beginning to rub it while he sucked the cock.
“You weren’t kidding about being good at this.”
Jeff briefly slipped his mouth off the dick.
“I’ve had quite a bit of practice.” Jeff noted. “Just let yourself enjoy it. And whenever you need to cum, just let it happen.”
Darren nodded in agreement as Jeff resumed his oral duties. As he sucked, Jeff pushed his fingertip into Darren’s ass, keeping it there and letting the sphincter tighten and wrap around the finger. Jeff bobbed up and down the penis as his finger explored deeper into the depths of Darren’s puckered love tunnel.
Jeff felt the cock throb in his mouth as he inserted a second probing finger into Darren’s ass. He could feel the sphincter squeezing his fingers as he expertly maneuvered his mouth all over his friend’s erection.
“I’m about to cum in a guy’s mouth!” Darren thought.
Darren arched his back as Jeff massaged his prostate. Jeff took the entire length of the penis into his mouth and suckled the base. Darren moaned again, unable to hold back, ejaculating into Jeff’s mouth. Jeff was unphased, continuing to suck as his mouth filled with fresh spunk.
After Darren was sufficiently drained, Jeff finally pulled back. He held his mouth open for a moment, showing Darren the semen inside. Then he closed and swallowed the load in one gulp.
“Yummy!” Jeff said with a big smile. “That was quite a delicious treat.”
“That was amazing.”
Darren stood there for a moment, enjoying the moment, as his penis softened.
“I’m not sure what the proper etiquette is here.” Darren said. “Am I supposed to return the favor? Do I need to suck your dick now?”
“There are no rules.” Jeff told him with a chuckle. “We’re just taking things at whatever speed you’re comfortable with. For now, I think we should head back to the living room and spark up another joint.”
“Sounds good.”
Jeff stood up, his cock still very much erect. Darren couldn’t help but stare at it as it swayed with every movement.
They got out of the tub and dried off together. Jeff put on a bathrobe and handed a bathrobe to Darren. Leaving the robes open and untied, they returned to the couch, once more sitting beside each other. Jeff picked up one of the joints and lit it. He took a long drag and passed it to Darren.
“How do you feel?” Jeff inquired. “Any shame or guilt about letting yourself cum in another man’s mouth?”
“I actually don’t feel bad at all.” Darren answered, taking a puff from the joint. “You’re fantastic at sucking dick, and really I’m just glad I’m finally allowing myself to explore this side of my sexuality.”
“That’s awesome.” Jeff told him. “I’m really proud of you!”
The two friends sat in silence for a while as they shared the joint. Once they were finished, Jeff broke the silence.
“Do you want to look at another magazine?”
“That’s okay.” Darren replied. “But… would it be okay if I held your penis again?”
“Of course! Just let me get this robe off.”
Jeff discarded his robe and Darren did the same. Jeff opened his legs a little and Darren looked down at his genitals. Jeff was no longer erect, but his soft cock still looked very nice. Darren reached between Jeff’s legs and took the penis in his hand.
“Would it be okay if I did the same?” Jeff asked.
Darren nodded, and quickly felt Jeff’s hand wrapped around his dick. Again there was a moment of silence as both friends appreciated and enjoyed the simple gesture of holding each other’s privates.
“Isn’t this nice?” Jeff suggested. “Two friends. Hanging out naked. Holding each other’s cocks.”
“I’m definitely enjoying it.”
Both of them were enjoying the attention between their legs, each of their dicks beginning to expand. The friends encouraged this expansion further by way of occasionally giving each other a friendly squeeze. It wasn’t long before they were each holding a fully erect cock in their hand.
“I think I’m ready.” Darren announced. “I think I’d like us to fuck now.”
“We can certainly do that!” Jeff told him. “Do you want to give or receive?”
Darren pondered his options for just a few seconds.
“I think I’d like to experience being on the receiving end.”
Jeff smiled and suggested that Darren get on the couch on his stomach. Once in position, Jeff parted Darren’s cheeks again and softly kissed him directly on his anus.
“What was that for?”
“Just kissing your anal virginity goodbye!” Jeff explained with a laugh.
Jeff took a moment to admire Darren: on his stomach, nude, his fully erect penis pointing down between his legs against the couch cushion. Jeff straddled his friend, his balls making contact with Darren’s balls, his hard dick resting on Darren’s ass crack.
“You’re sure about this?” Jeff asked. “You’re ready to have your ass fucked?”
“I’m not sure I’m ready for that entire cock up my ass.” Darren admitted. “But I’m ready to know how anal feels.”
Jeff squirted a very generous amount of lubricant over his dick as well Darren’s crack. Jeff worked the lube over his shaft with his left hand while his right hand massaged it between Darren’s cheeks and ultimately his virgin anus. He then continued to tease Darren, slowly thrusting his thick penis along his crack, before finally pulling back so that the tip was resting against Darren’s fuckhole.
Gently, Jeff began to push his cock into the tight hole. Darren moaned as his anus attempted to resist the intruder, but Jeff persisted and managed to pop the head inside.
“Holy shit.” Darren said.
“Don’t worry.” Jeff told him. “There’s plenty more to go!”
Darren bit his bottom lip as Jeff eased another inch inside. Jeff pulled back to the tip and then pushed back in, this time going another inch deeper.
“Doing okay?”
“So far, so good.” Darren replied.
Darren tried to relax as he allowed Jeff to sink even deeper into his ass. Just when he thought he couldn’t take any more of Jeff’s cock, Darren felt his friend’s testicles once again brush against his. Jeff paused momentarily, letting Darren enjoy the sensation.
“You did it!” Jeff told him. “My entire dick is inside of your ass!”
Jeff slowly began sliding his penis back and forth, in and out of Darren’s anus. Darren moaned with pleasure as the thick tool glided in and out, stretching him open.
“Would it be okay if I speed up a little bit?” Jeff asked. “If I fuck you a little harder and faster?”
“Go for it, dude.” Darren answered without hesitation. “I’ll let you know if it gets too intense.”
Jeff put his hands on Darren’s hips and started to passionately make love to his rear. He started with slow, full length strokes back and forth, but quickly worked his way up to a nice, steady pace of humping the warm, welcoming hole.
Darren’s erection throbbed against the couch cushion as he took his anal dicking.
“This honestly feels better than I ever imagined.” Darren admitted as Jeff’s penis pumped in and out of him.
“Good.” Jeff said. “It feels great to me, too. I like the way your asshole is gripping my cock.”
Jeff continued to give Darren’s ass a proper, hard dicking. Darren’s penis twitched each time Jeff was balls deep between his cheeks.
“I think I’m about to cum.” Darren said.
“Be my guest!” Jeff encouraged, steadily thrusting into his friend’s rear. “After you cum, I’m going to fill up this adorable little butt of yours.”
As if the passionate buttfucking wasn’t arousing enough, Jeff’s announcement of his intention to finish with an anal creampie sent Darren over the edge. With a moan, Darren began to ejaculate as he was being pounded. Several spurts of warm, sticky sperm coated Jeff’s couch cushions.
“My turn.” Jeff told him.
Jeff administered a few more powerful strokes before plunging his cock deep into Darren’s ass. Darren could feel the thick penis throbbing and twitching against the walls of his rectum, as well as the generous deposit of cum Jeff was making.
Jeff left his dick in place for a few more moments, making sure every drop of semen made it inside of Darren’s anus. He then slowly retracted his shaft from Darren’s freshly fucked hole.
“Wow.” was the only thing Darren could think to say, staying put on the couch as he took in the various thoughts and sensations he was feeling.
“So I guess you really enjoyed that?”
“Very, very much.” Darren answered. “Sorry I nutted all over your couch.”
“No problem at all.” Jeff said. “You’re not the first to do that, and you won’t be the last.”
Darren could feel Jeff’s cum start to leak from his hole, trickling down his taint and over his testicles. He finally shifted from his state of bliss and stood up from the couch.
He turned to face Jeff, both men nude and spent from their fantastic sex.
“Any regrets?”
“None.”
“And did me fucking your ass like that make you stop liking women?” Jeff asked. “Did me sucking you off earlier make you detest the thought of a wet pussy in your face?”
“Not at all.” Darren answered.
“Then congratulations!” Jeff told him. “Having sex with a man didn’t make you gay. And now that you know that, you’re free to have sex with as many men as you like.”
“Wow, you’re right.” Darren said, more sticky sperm leaking from his asshole. “That’s pretty cool.”
“Let me go get a towel to wipe off the couch.” Jeff told his friend.
As he walked away, Darren reached behind his back and ran his fingertip over his wrinkled hole, scooping up a dollop of Jeff’s semen. Without giving it a second thought, Darren put the finger in his mouth, tasting the special treat.
“Did you just taste my cum?” Jeff asked, carrying a towel and beginning to wipe off the couch.
“Yep. I couldn’t help it.” Darren admitted. “Pretty tasty.”
Darren helped himself to another fingertip of sperm as Jeff finished wiping the couch, setting the towel on the coffee table.
“Would it be too forward of me to ask you for another favor?” Darren inquired.
“I just came in your ass. You can ask me whatever you want.”
“I was just thinking… I’ve had some wine, we’ve smoked some weed… it might not be smart for me to try and drive home.” Darren said. “Do you think maybe I could spend the night?”
Jeff smiled at him.
“Of course you can stay the night!” He answered. “There’s just one rule… whoever sleeps in my bed has to sleep naked. Can you handle that?”
Darren smiled back and nodded, confirming his willingness to remain nude.
“Perfect.” Jeff said. “And then maybe we can fuck again in the morning?”
“Sounds good to me.” Darren replied. “I think I’d like to try sucking your cock next time.”
“That’s fair. You should try fucking my ass next time, too. It’s important to find out what you enjoy most when you’re having sex with other guys. Sucking or being sucked. Fucking or being fucked.”
“Thanks for helping me with all of this.” Darren said. “I feel like I’ve learned a lot from this experience already. You’re a good friend.”
Jeff put a hand on Darren’s shoulder.
“It’s been my pleasure.” Jeff told him. “I’m glad you finally worked up the courage to admit your fantasies to me. And also the courage to explore us fooling around together. It was really special to take your anal virginity.”
“Mind if we smoke your last joint?”
“Not at all. I can roll more tomorrow morning.” Jeff said.
The two friends remained completely naked as they shared the final joint and conversed about the sex they had, as well as options for more sex in the future. This of course led to both of them getting turned on again. Rather than having another round of sex, they instead agreed to sit on the floor in front of each other and masturbate together.
They both enjoyed their final orgasm of the evening, each watching the other stroke their hard penis as they flirted, and eventually each watching the other one orgasm, ejaculating even more cum into the air.
When they got into bed, they fell asleep in a spooning position, with Jeff’s soft dick nestled snugly against Darren’s bare ass crack. Darren smiled to himself.
“I finally did it.” He thought. “I finally had sex with a man.”