⁕ Disclaimer:
This story is strictly fictional and contains male-on-male (gay 🏳🌈 ) sexual content, both implied and explicit. 🔞 Reader discretion is advised. The names, ages, circumstances, parties, and locations mentioned in this narrative are entirely fictional. Any resemblance to actual individuals is purely coincidental. This story is a product of the author’s imagination. The author does not endorse any products or entities mentioned herein.
⁕ © Copyright:
All copyrights to this story remain strictly that of the author. No other publication, use, or reproduction of this story or parts of this story is allowed without the author’s written consent. It is published on www.gaydemon.com. Under the pseudonym of StrykerJ.
⁕ Thanks for reading:
👍 LIKE or RATE IT. That is appreciated. Or Leave a comment or a question after you’ve read this story. Thank you very much.
Curious Club Cruise - Part 2.
Shopping for a new look.
The very next day after school, I picked up the phone and dialed the hairdresser Tony had suggested. The moment Armando, the owner, answered, I felt a mix of anticipation and nervousness. I explained that I was looking for a complete makeover, hoping to spark some enthusiasm in his voice. Initially, his response felt lukewarm, almost as if he were trying to brush me off with polite indifference. However, everything shifted dramatically when I mentioned that Lieutenant Tony Jackson had recommended his salon and that I was TJ’s younger brother. A spark of recognition seemed to ignite our conversation, and we fell into a casual banter, easing the tension in the air.
When Armando asked me to send a recent picture to get a better sense of my style, I eagerly emailed him the upper half of one of the kinky dick pics I took last night. I had shared it with my brother the previous day, showing myself off, confidently clad in my leather jacket and gloves. Before I knew it, an appointment for Saturday morning was confirmed. To my delight, Armando followed up by sending five images to my email, all striking photos of handsome young men, each with stylish hairstyles that seemed to radiate confidence. The excitement of choosing a new look began to bubble within me as I imagined the transformations that awaited.
Tony had reached out to me through a couple of texts that day, suggesting some shops where I could go to buy myself some hip clothes. Mom would certainly never take me shopping there. He feared his old stuff would not fit me properly. However, his things fit me surprisingly well. I am a few inches taller than my brother’s 6 feet, yet a lot less muscular, of course.
Heck, Tony playfully hinted that I should head out to pick up some ‘pharmacy’ essentials as well. Telling me to buy lube, condoms, an anal shower, and some ‘training toys’ of my own. However, much to my surprise, his suggestion led me straight to an adult store, leaving me both amused and bewildered by his choice of apothecary recommendations.
That Saturday, I arrived a little early at the entertainment square on the east side of town. I looked around the square for a bit. Most clubs and bars had just closed, but the retail shops and a few lunch rooms had already opened. This part of town was off-limits, according to my parents. They warned me, “... What goes on there is no use to anyone... Filth and buggery awaited the unexpected visitor there. They will rob and murder you if you go there!” they said.
It was a vibrant Saturday morning, and the air buzzed with the thrill of freedom as the school exams were almost done. I was ready to indulge myself in a fun-filled day of adventure! Hoping this will alleviate my exam nervousness. As I strolled around the bustling square, I was greeted by a lively array of nightlife and entertainment spots that pulsed with energy.
Tucked away in the side streets were a few quirky adult stores and some shadowy alleys that sparked my curiosity. Contrary to my parents’ warnings, nothing felt overly daring or dangerous here. The crowd was diverse and lively, bustling with laughter and excitement, far from the muggers or perverts I had been led to believe would be lurking about. It was a day ripe with possibilities, and I was ready to embrace them all!
I settled contentedly onto the sun-drenched terrace of a café. The warm early summer breeze tousled my hair. I ordered myself a steaming cup of coffee and a slice of fruit cake. With a leisurely hour ahead of me before my appointment at Armando’s, it was the perfect opportunity to indulge in the vibrant surroundings.
I soaked in the lively atmosphere, observing the bustling crowd as they did their shopping. At the same time, watching the remnants of last night’s bleary-eyed party-goers meandering tipsily on their way home. A blend of laughter and chatter filled the air.
It struck me how free and openly the lovers wandered arm-in-arm around the square. Not only the straight couples did that, but also the gay men and women. And no one seemed to mind me watching them. I even got a few compliments from some older twinks. Saying I looked cool wearing Tony’s leather biker jacket. They, too, wore leather gear. The guys had clearly just left one of the gay clubs after an all-night party. So, I reciprocated the compliment on their outfits. And that made the older twinks grin hornily at me. The thought occurred that I was doing the right thing. I smiled back at them.
I strolled along the clubs, bars, and shops on the square. Looking at the information posted at the clubs that Tony had suggested. The Cottage was a nightclub for 18 years and over. The Mountain, however, was a full-on gay club, bar, and restaurant. You had to register to go to this club at the back. I chatted with the doorman at the Mountain’s bar and decided to get a membership after asking what it cost.
He said grinningly, “... For you, sexy? Nothing, but are you sure you can handle it?”
“I can,” I replied confidently. “... What’s it you need from me?” I answered boldly. However, I started to feel a bit nervous at his steady gaze.
“Just your name and address and a check of your ID,” he answered warmly, saying, “... We can do that now if you want. That saves the hassle of having to wait in line tonight. The diner is open around five. The private men’s club is open from ten to two AM. After that, the doors are locked until nine AM, when we close and clean up. We constantly look for cleaners... If you’re interested?” asked the doorman.
“Not right now... But sure. Sign me up,” I said happily. Somehow, the job offer had me interested. Me working at a gay club? Mom and dad would go ballistic.
With the membership card in hand, I left for my hairdresser’s appointment. It appeared that Armando had been following my progress around the square. He sat in the sun on the window sill outside his shop, drinking a steaming mug of coffee. When I approached, he jumped up to greet me as if we were old friends. Apparently, his brash reaction had shown some fear or apprehension on my face. Because he quickly explained that TJ had told him all about me. He said he was delighted to finally meet me. Armando looked me up and down a bit and pushed me happily into his shop.
One and a half hours later, I exited the hairdresser with a sexy new look. Long and spiky at the front. But much shorter at the back with trimmed-up sides. The few blond highlights on top added just that bit of extra. It was very different from the sleek, brown, boyish hair-do I was used to all these years. I grabbed a quick lunch at a bar Armando had suggested. Spending the rest of the afternoon shopping for clothes. I also got my eyes measured for new glasses and bought extra contact lenses. I picked out a pair of Ray-Ban frames that accentuated my face. It was a totally different look from my old-fashioned horn-rimmed glasses — Much more macho.
I ended the day out at the adult store my brother had recommended. I had half expected it to be one of those dingy adult places. But it much more resembled a well-lit pharmacy. Well, a pharmacy specializing in sex toys. Luckily, the staff were accommodating. They even gave me some leaflets on how to use the things properly and safely. Practical instructions like these were not even provided in the sex-ed classes at school. The very mention of anal sex in those classes was very much off-topic. I left with a couple of training toys, rubbers, lube, and assorted items for a safe night out or a steamy one-night stand.
At home, I eagerly tried on the array of new clothes I had purchased. I mixed and matched each piece with Tony’s vibrant party attire, allowing my imagination to run wild. Eventually, I settled on three potential outfits that made me feel like a completely different person — no longer the nerdy kid draped in my mom’s outdated choices. A more daring, eclectic style had replaced the second-hand old office slacks and button-up shirts that dad used to wear.
TJ’s spirited party clothes had been an incredible boost, infusing me with a newfound confidence that I never thought I could possess. I relished the thought of stepping out in these sharper, more rugged leather and denim looks. They indeed banished the fear of embarrassment that my parents had instilled in me. Rather than feeling ashamed to dress this way, I embraced a bolder version of myself, ready to take on the world.
On my brother’s guiding hand.
I took a few hot photos of the clothes. Sending them to Tony’s phone. But the asshole did not reply. This made me a little angry. I had expected him to answer promptly as he usually did. But after two hours, I still had not heard back from him. I even double-checked if I had sent them to the correct phone number.
A little later, around dinner time, the doorbell suddenly rang. Two figures were discernible through the frosted glass. When I opened the door, Tony and another tough-looking muscle guy greeted me.
“Hey, buddy... Eaten yet?... I thought you’d like some Chinese... Damn, those new clothes looked so cool we had to come and see for ourselves,” said Tony. Showing three large bags of food.
The two muscular, macho Marines pushed me gruffly inside and closed the front door behind them.
“No need to let the neighbors know I have been here... But damn... Look at you, sexy,” laughed Tony naughtily.
In fact, the stud pushed me to the hallway wall and moved in to kiss me. His lips opened as he moved forward. Tony immobilized my head with one firm hand. His tongue directly licked my cheek before he kissed me. The incredible rudeness must have left my lips parted. Tony took this as a sign of lust and penetrated my mouth with his tongue as well. My brother gave me a French kiss that was hotter than I had received in a long time.
My eyes, wide in surprise, looked from my brother to the other guy. Tony saw this. He grunted and kissed me even harder. Letting his tongue play with mine for a long time. When he broke off, his buddy moved forward, saying, “... Hey kid... Mind if I...”
I just licked my lips. Tasting Tony’s saliva. The other guy took this as a yes and planted a wet kiss on my lips as well. He held my hips with both his hands. Our crotches pressed tightly together. He pulled back for a second and gazed straight into my eyes.
“Mmm, nice...” he muttered hotly. “I can see the family resemblance... My name is Captain Daniel Carter — TJ’s man. But I don’t mind sharing him. Damn, you look hot, kid.”
“Guys... are you here to eat me, or shall we talk over dinner first? I have so many questions. But fuck... Damn... Hell, that was a welcome and a half. I nearly dropped a load in my new pants,” I sheepishly laughed at the hot Marine studs.
“Language, Brian! Dad won’t like it when you talk like that!” laughed Tony. He grabbed me around the waist and walked us into the kitchen. Tony’s boyfriend was a fair few years older than him. I guessed he was about twenty-eight or twenty-nine. Very muscular and tall. Both studs were dressed in some casual combat gear. But they combined it with some of their civics. Daniel wore a frayed-looking black denim vest over his skin-tight green T-shirt.
Tony wore a buff black leather bomber jacket. He had pushed up the sleeves to his elbows. TJ had clearly been working out. His upper arms and neck were twice as thick as the last time I saw him. This noticeable transformation highlighted Tony’s impressive physique, making it difficult for me to look away from my sexy brother. It made me wonder if I could achieve that amazing look, too.
I set the table for three, and we ate, talked, and laughed until late that evening. My brain was swimming with all the details, suggestions, and valuable instructions about sex with guys. Their openness took me by surprise. It felt like a warm shower as I let their dirty-talking words wash over me. Apparently, Daniel had seen my confusion and pleasure mingle.
However, his offer to give me some practical cock sucking experience, right there at the kitchen table, took me by surprise. This was all a bit much and considerably too sudden. I choked up and felt my eyes well up with tears.
Jumping up, I quickly left the room. Making the feeble excuse that I needed to pee. When I came back, Daniel softly grasped my hand in his. “Sorry, mate, I did not mean to scare you,” he whispered.
A Marine instructor taught me close combat.
Tony laid a hand on my shoulder. “Dan was only trying to help, bro... Better to get some experience now than fumbling your first time out there,” said Tony quietly. Gesturing with his thumb to the outside. I looked from Daniel to Tony and back. Sighing heavily at the men.
“Just let your hand wander a bit, bro... Dan would love to give you your first mouth full. And we’re all friends here. What better way to learn than this?” suggested my brother.
Daniel looked me deep in the eyes, tilted his head, and softly kissed me. Guiding my hand over his cargo shorts. I liked how his hot, stiff prick felt, but I was glad the man helped me navigate my hand over the throbbing bulge.
“That’s it, Brian... Stroke that thing. Rub your thumb over the head. Grasp my balls. Feel them. Do you like it? That’s just as nice as yours. Damn, you’re a big boy... Why don’t you drop to your knees and... Ha!... Well, free Willy!”
I was completely at the mercy of these two, but honestly, the chaos thrilled me. My mind was ablaze with thoughts, and I could almost feel the steam pouring out of my ears! The intensity of it all sent my heart racing, and I relished every electrifying moment. I was that hot and horny.
Tony had pushed me to my knees, and I felt Daniel’s hand press on the top of my head.
“Quick, unzip me, Brian... Take it out before it rips a hole in the cloth! Man, I am so hard for you. I am going to make you eat my dessert,” moaned Daniel hotly.
Just as in the wet dream, I had a few days back, I silently obeyed the command. Though I gasped in shock as I saw the size of Dan’s manhood. The 9-inch dick was a bit shorter than mine but nearly twice as wide. It’s a genuine handful. I shuddered when I realized that TJ took this thing up his ass. I thought I would not be able to do that. No way in hell!
“Take a firm hold of it, boy. That’s it. Don’t be afraid of it. You can’t hurt me.” Captain Carter said, aroused at my touch. I curled my hand around his throbbing 9-inch fat pole. Moving the uncut foreskin up and down, looking intently at the beautiful shaft and moist glans.
“Lick your tongue around the head a few times. Then, take it into your mouth a little. Make the head nice and wet,” said the Captain instructively after a few minutes. His deep voice hypnotized my brain, and I did as instructed.
But as I got into my stride, he moaned hotly, “... That feels really nice. Oh, shit, yeah! He’s a quick study, TJ... Fuck he’s doing it. Suck me down, Brian. A little faster. Up and down. Hell yeah! Blow me, boy... Blow me hard.”
My brother kneeled beside me and watched me closely as I blew his man. Tony instructed me, “... Move your hand up and down as well. His dick is big enough. And it makes Dan shoot even harder and faster.”
“Fuck guys... I want to enjoy this a while longer. Slow down!” barked the Captain. “TJ... Show the boy how to deepthroat!”
Tony slowly took the cock into his mouth, but he expertly made all the 9-inches disappear into his throat. Daniel held my brother down a long time as Tony looked lovingly up at his man. Dan relinquished his grip on TJ’s head and gave him a few seconds to breathe before ordering him, “... Gag on it, TJ... Choke on that cock!”
My brother quickly gobbled up the big dick again and made the hottest gurgling and choking sounds I have ever heard a man make. This wasn’t lost on Daniel either. He simply loved this. He was in total control as he face-fucked Tony. Between mouthfuls, Tony told me to play with Dan’s swinging balls.
After a while, Tony released the hot cock from his mouth and asked, “Want to try that, Brian?”
“What?... Deepthroat a monster cock like that? I don’t think I can,” I said sheepishly.
“Sure you can... Just tilt your head back a little more and open your throat. Dan knows not to hurt you. He’ll guide it down. And if you do your best, he’ll feed you a big load straight into your mouth,” said Tony, dirty.
By then, I was so horny that I would have let them rape my holes without any more prep. Heck, the muscular Marines could have double-dipped my ass without any worries. I was putty in their hands. After repositioning myself, I felt Daniel guide me over his fat dick. It went in much more deeply than before. I started to gag, but Tony told me to breathe through my nose and let Daniel take control. I did, and before I knew it, I had nine fat inches pumping in my throat. The hunky Captain pushed me off his dick for a few moments.
I gasped for air as Tony breathed into my ear, “... He is nearly there... Expect a fat load to splatter in your mouth. It doesn’t taste half bad. Just don’t spit it out and make a mess. Swallow what you can. Here he comes again... Prepare yourself and enjoy it, Brian!”
Dan wasn’t as soft and gentile the second time around as before. He stood up and face-fucked me gruffly. Grunting dirty at me, telling me what a good little cocksucker I was. Daniel grabbed the top and back of my head when he was ready to explode. Forcing himself relentlessly down my throat as he let the orgasm well up from his balls. I had barely understood Tony as he instructed me, “... Breathe through your nose and receive his load like a man. Start making swallowing movements with your throat. Dan likes that!”
I calmed down and let my throat tickle his cockhead. Captain Daniel Carter’s cock grenade exploded in my throat. Slowly, he pulled it back, and stream after sticky stream filled my mouth. I had never tasted anything like this. It was salty, sweet, a little bitter, sticky, and hot. Damned hot. And there was a lot of it. Dan just kept on cumming. After his massive orgasm eventually subsided, the Captain finally pulled out. I fell to the floor on my ass as I looked up at Tony and Daniel Carter. Breathing hard and smacking my lips.
Going for round two.
I tried to get up after a while, but my knees were too weak. Not knowing if it was the prolonged kneeling position or the sheer lack of oxygen. Both guys pulled me off the floor and started to lick and kiss my cum-covered face. Their hands wandered over my body as they began to undress me. With my new jeans with designer rips around my ankles, I felt Dan’s fingers starting to play with my butthole. Tony had unsnapped the old white denim shirt, revealing my torso. My brother had roughly torn the sleeves off this shirt years ago. But the butch look went well with the new jeans, I thought.
“Guys, why don’t we go to Tony’s room and continue this there? I need to clean my ass out first, though. Maybe we can... Umm,” I started to ask.
But both guys looked at each other with dirty, sympathetic grins.
Saying, “... Nah... We can play with some toys, jerk off a bit, and watch an instructional porn or two together. But you’re a bit too young for me.” said Daniel warmly, “... And well, TJ is your brother... Best leave your first time for an actual lucky guy,” said Daniel calmly. I understood these two would only take this so far. And I knew why, but I still looked pleadingly up to the hunky gay Marines.
“Oh, don’t look so disappointed, Brian. We’ll make sure you’ll enjoy this, too,” my brother told me reassuringly.
“Okay... but I had hoped for a bit more. Are first times always this scary? I... I am... I am nervous as heck,” I stuttered as I said it.
“We are friends... No need to be nervous. It’s just a bit of instructional fun. And I heard that TJ told you to buy some toys of your own. Did you? We can christen them tonight,” smiled Daniel warmly as he followed Tony upstairs. Dragging me along in his wake.
I broke off to go to my room to take a toilet break. I took the new anal-douche tube with me to flush my ass out. I had read the pamphlet that came with it on the bus home. I cleaned myself and took my training set of buttplugs and a large vibrating BBC toy with some lube upstairs to TJ’s room.
Rim with a view.
When I entered Tony’s room in the attic, I saw the two guys lying on TJ’s bed. They were already playing with each other. Oblivious that I had arrived. The guys were butt-naked and fully aroused. The two of them looked fabulous together. I set my toys and lube on the bedside table and walked back to the foot of the bed. I crawled between the two guys, breaking up their foreplay. And they did not seem to mind this one bit. I was only wearing Tony’s old leather posing jock accentuating my boyish buttocks.
Daniel grinned at me and pulled me over his chest. Pressing my lips to one of his pierced nipples. I took the hint and started licking and sucking on it. I felt Tony move away from our side. But what he did next made me scream in pleasure. TJ hooked his massive arms under my legs and lifted my hips in the air, spreading my cheeks with his calloused hands. The man buried his face between my buttocks. Rimming my asshole deep with his tongue.
After spitting at it a few times, the thing loosened up and allowed a full tongue penetration. I had died and gone to heaven. TJ ate me out like a pro. Daniel lifted my head and gazed into my eyes. Watching me experience my first intense ass rimming. My brain had gone to mush. When Captain Carter broke his gaze, he looked at my toy collection — picking out a medium-sized buttplug from the training set of four sizes.
“Wanna try this?... Boy?” he softly asked. I nodded, and Daniel said, “... Let us get it nice and wet then.”
The Captain took it into his mouth and licked it all the way to its base. He made me do the same before applying a liberal amount of lube over the tip. Smearing the goo around, he told Tony to make some space. His two lubed fingers drove deep past my sphincter. When I winced a bit, he pulled out. After applying an extra dose of lube on his hand, Daniel Carter started to finger fuck me for a while. Letting my hole make sloppy slurping noises as he pounded my prostate. By now, the three of us were thoroughly turned on. Even though, no cock had penetrated my virgin butt.
Tony had also grabbed some lube and started to help prep my ass. Ending up stretching the outer ring open with a finger from each hand. Daniel drove the plug very carefully inside. Nice and slow. Pumping it a little and letting my butt get used to the feeling. I had nothing up there before but a few fingers of my own. I quietly let the guys toy my ass. Only making the occasional pleasurable sound to let them know my ass was enjoying this attention. But I wanted more. I needed the real thing.
Apparently, Tony had read that thought in my expressions. I was eyeing his 8-inch cock with great lust. But he calmly said, “... Dan... I think Brian wants something bigger... Don’t you, B?...” I nodded as Daniel watched his man. Tony bent over the two of us to pick something out of his toy box. Out popped the enormous 16-inch black dildo. My brother slapped it on my ass and laughed meanly. “This is what you want, isn’t it?... Fucker.”
I just looked worriedly over my shoulder. Daniel pulled on the medium-sized buttplug still lodged deep in my ass. The thing was long but not too wide around the base. And even that had been quite painful going in. So, that enormous 16-inch dong? No, I wasn’t quite ready for that.
Toy Story.
Daniel moved to my backside. I was still lying on my stomach as he started fucking me with the buttplug. Pulling it out and sliding it back in. Stretching my sphincter wider and wider. Loosening it up for whatever came next. The longer he did this, the easier it became. The sneaky bastard had secretly taken the largest of the buttplug training set with him as he repositioned himself. Once he had pulled the medium-sized plug out. I let out a scream of genuine pain.
Daniel had roughly slammed the biggest one in my ass without any warning or additional lube. My instinct was to poop that thing out as fast as it had forcefully penetrated my boy-cunt. But Daniel did not allow that. His fist was preventing me from doing that. Holding the base of the plug firmly against my ass. As an added measure, he had slid his considerable body weight on top of my back. I could feel his leaky cock slide against my buttock. Man, that large plug was something else. It was nearly as wide as Daniel’s cock.
“Shush, boy... Let your ass get used to the size, Brian. Sorry... That was a bit rough. I know. But you’re okay. Lay still. Feel my body on yours. TJ... Give the baby boy his pacifier. That’s it. Suck on that dick for a while.”
My sphincter grabbed hold around the base of the plug. And my eyes started to roll. These Marines had broken my resistance.
As instructed, Tony had sat himself on the pillow and moved forward so I could take his cock in my mouth. Adamant as I had been before not to make out with my brother, as eager I was now. Ignoring this was wrong on many levels. Captain Daniel Carter was right. It did shut me up nicely.
“See... not so bad now, is it?” whispered Daniel in my ear.
And damned if I know, but it wasn’t. It actually started to feel good. Daniel had removed his fist from between my buttocks. He had begun to grind his hot 9-inch manhood up and down the crack instead. It had the same effect, though. The buttplug could not escape. But by now, the sphincter had given up. My ass stopped trying to remove the foreign object.
And the three of us lay there, grinding, licking, sucking, kissing, and talking dirty. Daniel was whispering in my ear as if he was actually fucking my brains out. Tony gave me all kinds of dirty suggestions as well. His cock was lodged deeply in my mouth. I could only grunt and moan. This was the best feeling I had while having sex. This did not even come close to the sex with girls. It was much hotter and dirtier. I loved it!
When I moved my head a little, my eye caught the 11-inch BBC vibrating dildo I had bought. The veiny thing had realistic, supple skin and was colored to resemble the real thing. It was roughly the same width and shape as my own prick. My hand made a grab for it, and I smacked it against Dan’s face on my back. Tony released his cock from my mouth and laughed out loud. Daniel slid off me and started to laugh, too.
The guys made me roll over. Sitting behind my head, my brother held my legs in the air as Daniel removed the large buttplug from my ass. Without a word, he squirted some lube on my pink butthole. Greasing up the big black dildo, as well. Lovingly stroking the realistic dong, distributing the lube along the shaft. He was ready to show me what a man-sized tool would feel like in my virgin ass.
< Continued in part 3 of 7 >
Thank you for reading this story.
Please give it a 👍 Like or a Comment if you are inclined to do so.
And if your hands are not too dirty from all the spilled cum! 😋
© StrykerJ - August-2022. Original series: Night-time Club Cruise
Edited, renamed, and re-uploaded: March-2025.
