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Curious Club Cruise - Part 1.
The bragging and smack-talking nerd.
At the beginning of the year, I hit the big one-eight. Like most guys around 18, I could only think about sex. However, unlike some of my classmates, I was finding it hard. The pesky problem — my relentless sexual desire made it nearly impossible to focus on my studies. And that was highly inconvenient around exam time. It was kind of ironic, really, because I had never been that into girls. At school, the girls saw me as the shy, nerdy guy in outdated horn-rimmed glasses. And the guys joked that I was scared of my own shadow.
But honestly, it wasn’t all that grim. Sure, I might have lacked experience compared to my classmates, but I still found my way into a few pants over the last few years. Heck, in these past couple of years, I butchly jerked off with some guys in the school’s locker room. During the latest get-together, the guys started bragging about their nasty conquests. Gabbing about with whose daughter and down what dirty alley they did what. And if it weren’t for the size of my member, I would not be included in these sneaky jack-off sessions. I look nothing like those muscle jocks.
I felt like an outsider, wishing I could join in their smack-talking. It was clear I needed to catch up to them. I just didn’t have those kinds of experiences. No, my lovemaking was limited to taking a girl home after a school dance. Or picking up a neighbor to fool around with her at her place. My mother would have killed me if she knew that.
One of the guys noticed my reluctance to share my tall tales. And like a good little nerd, I made stuff up on the fly. I think they saw right through me, though. Because, after we had nutted, Mark Edwards took me aside and softly asked, “... Was that real, Jackson?... Or did you make that up? You don’t seem the type to nail a girl behind the bike shed at school. And, Brian, you certainly never called any woman a bitch like that!”
My story was relatively hotter than the actual fact. I had been approached by this particular slut. Wanting to get it on with the next guy she laid her eyes on. This happened to be me. And it was behind the bike shed at school. But that’s where reality ended.
I braggingly lied that I had dragged her behind the covered bike rack and nailed her up against the wall. Choking her with one hand as I fingered the wet slit open. Whipping my cock out one-handed and penetrating her cunt from behind like a boss.
The fact of the matter was that she took control. She made me kiss her. Pushing me forcefully behind the shed. She drove her hand into my short slacks and whipped my dick out. Roughly pulling and tugging on my meat behind the building. But when I couldn’t get hard fast enough, she humiliatingly laughed in my face. She kicked me in the balls and left disappointedly. I just stood there, watching her horny ass wiggle away.
When I told my well-honed classmate this painful truth, Mark did not laugh. Instead, he laid a hand on my shoulder and said understandingly, “... Dude, you just need to go out and get some for real. It’s worth the effort. Sure, most girls will brush us off. But keep at it... There is one out there for you. Dress up in something cool and just go to a club or something. Make yourself available. Without those glasses, you’re not bad-looking.”
Mark stopped talking for a second and looked at my crotch for a fleeting moment, saying, “... And that thing of yours, B... Well, it’s the biggest one I’ve seen so far.”
He faltered and shyly whispered, “... If I weren’t with my girl, I would do you myself, Jackson.”
He blushed scarlet as he said it. But I knew what he meant. Ever since the first time we met, my 10-inch slender dick got his attention. Although he only saw it fully erect in our senior year. That’s when I knew he was into men as well. We kept up the pretense for the other guys. Yet still, he did not do more than look in amazement. The jock’s he hung out with became my ‘friends’ too, as if my size rubbed off on them.
The dream that woke me up.
This night, Mark’s words still echoed through my horny mind. With my parents gone, I lay stark naked on my bed that warm summer evening. Was Mark really into guys, too? Would he really make love to me? Until now, the notion of doing it with a guy was just a cockamamie idea. Looking between my legs, I noticed the whole kinky thought had turned on some part of me. My hand had a firm grip on my shaft, and my mind was racing with images I had only seen online by accident. I let my brain wander as I stroked my cock vigorously.
In my dream, a fierce biker dude would corner me and gruffly push me down a side street and into a dirty alley. Out of sight behind a dumpster, he would rough me up a little. I would try to struggle away from him, but he was much too strong for me. Forcing me to my knees, he presses my face into his leather crotch. Using both his hands, he rubs my lips over the swelling shaft.
Ordering me in no uncertain terms, “... Lick it, Boy! Taste the leather.” I did, and this would make his cock even stiffer.
“Now, Take it out...” would be his following command. And with trembling hands, I would do that, too.
“Suck it down deep, Boy!...” he may scream ruthlessly. As his hips thrust forward, both his hands prevented me from pulling back. In a blink of an eye, the big mushroom cockhead lodged itself in my throat. What happened after that, I can’t recall. I would probably pass out. What a dream!
Suddenly I woke up and felt my cum dripping off my face and torso. I had never, never ever, cum this hard in my entire 18-year life. But it felt marvelous. Out of breath and slightly confused, I lay in bed playing with myself for over an hour, thinking about what my brain had concocted for me. The roughness of it all was something I had missed while I made love to the five girls I had done over the past three years.
The kinky leather that the guy was wearing made it even more exciting. I don’t have any of those kinds of clothes. Heck, I doubt I can even pull off that look. I felt just too skinny. With the horn-rimmed glasses, my mother made me wear, I looked like a true nerd. My schoolmate, Mark Edwards, had told me to wear something cool and to go clubbing. Well, something in leather would undoubtedly fit the cool category. And I could get contacts or titanium-rimmed glasses. Maybe I really should try to butch up before I go to college.
“It can’t hurt,” my inner voice told me excitedly.
My older brother, Tony Jackson, was the only guy I had seen wearing leather stuff like that. He is six years older than me and works in the Marine Corps now. But he had run away from home when he was 18. And I lost contact with him. He and my parents did not see eye to eye. Tony was sexually active from a very early age. However, anything to do with sex was, and still is, taboo in our household. At 18, our dad had caught Tony having sex with one of the neighborhood girls in our garage. By the sounds they made, Tony had died and gone to heaven. On the other hand, dad’s fury sounded like he would bury my brother alive. Not long after that, Tony left us.
I often wondered how my parents managed to have us. They must have had sex at some point. But according to their weird look on life, even holding our dicks to pee was a filthy thing to do. No, sex was not for their sons. But I knew, years before Dad caught him, my older brother was having sex with our neighbor’s daughter or the girls at school. He just lived for sex. Well, that... and fixing up his motorcycles or hanging out with his butch mates.
Reconnecting with my estranged brother.
Tony is everything I am not. He is a good-looking squad jock into anything that would annoy our parents. And Tony loved to wear his leather and denim gear when going out with his friends. Again, this was to the annoyance of our parents. By the time he turned 18, Tony was a buff bully. A mix of a muscle jock, a punk-rocker, and a player. Man, he was so cool. I looked up to him. And I still do. I still sort of miss having him around. If only for his brotherly advice about girls and shit like that. Our parents are no help there either.
And on the whole, I am not that outgoing. I never have been. Certainly not the way Tony was. That is why opportunities to make out with someone are few and far between. And to be honest, after that dream, I don’t even care if it is a woman or a guy. So, I decided I needed to get Tony’s advice. If only to ask him if I could borrow some of his much cooler clothes. After all, you never get a second chance to make a first impression.
I dialed his number on the landline, but I got his voicemail.
“Hey Tony, pick up, man. I know you’re there. I need a bit of advice about... Well... Umm... mom and dad are gone. And I want to go clubbing and maybe get...”
I stopped talking a second and said, “... Well, call me if you got this message. I really need to talk... Bye, TJ. Brian.”
I had to leave Tony a voice message because he never answered my parents’ phone if he could avoid them. Within seconds, he called me back.
“Hey, bro!” said Tony happily, “Long time no see, Brian... What’s up? Are you finally ready to chase some pussy then? I guess you’ve not told dad this... hahaha,” Tony joked.
“Hey there, TJ... ha... No! Mom and dad are gone for a couple of weeks. And... Umm... Yeah, I’m ready for some pussy.”
And half under my breath, I muttered swiftly and quietly, “... Or some dick.”
It went quiet on the other side of the line for a while. I swore I could hear the cogs turning. Had I just offended my brother? I gave Tony some time to respond, but he didn’t.
I added, more to break the awkward silence than anything else, “Tony, I want to go on the pull but don’t know what to wear. And if you have any advice on cool clubs or bars, that would be welcome too... Heck, any advice would help me out... Tony? Are you still there?”
I knew the man still lived in the area. I saw him going about his business in the city a few times. Even though we never spoke.
“Umm... sure... I think I can help you out. So, what’s your plan, B? Just looking to get pissed drunk? Or hoping to get laid?” Tony replied hesitantly.
Now, it was my turn to get my thoughts together. How could I explain my predicament to my older brother? I know I can tell him anything. He would certainly not inform our parents. So, I decided on the whole naked truth.
“Man, Tone, where to start?... One of my schoolmates told me I needed to dress up in something cool. And go clubbing to pick up someone. Man, I am about to explode. I am so horny all the time! And well, I just have to get laid, Asap! Maybe that will help with my exam nerves, too.”
I stopped talking and cleared my throat. Thinking my brother would need the whole truth. “... Umm, Tony, I had a dream about sex with a guy. A wet dream... And, well, I have never been with a guy. But... But... Maybe,” I faltered.
After a second, I added, “... Oh well, forget it —... Can I wear one of your old jackets, Tony?”
Again, it went quiet on the other side of the line. But when Tony replied, he quickly said, “... Brian... Go upstairs to my attic room. I expect my stuff is still there, ain’t it?... Open the wardrobe and remove the bottom shelf. There is a hidden panel on the left. It leads into the crawl space. That’s where you find some things that might interest you. Go exploring... Maybe you’ll like it too. I sure did... If you do, then call me back later. If not, leave it out. I’ll drop by to collect the last of my belongings later this weekend or the next. See you then, bro!”
Prowling, and eye-opening discoveries.
With that, Tony hung up rather suddenly. Wide-eyed and with excitement coursing up and down my spine. I got up out of bed. After a quick piss and a wash, I snuck up to Tony’s attic room. Only wearing a pair of tight black boxers. I am not sure why I kept up the secrecy. I was alone in the house, after all. I wondered what I would find. The whole thing made me somewhat nervous. The bedroom was the way he had left it six years ago. No one had been in here besides Mom’s occasional dusting and vacuuming. The room still had Tony’s scent on the air, though.
The built-in wardrobe stood between the attic’s crawl space and the door to the landing. I opened it with trembling hands. The first thing I noticed were TJ’s cool studded belts and artfully ripped denim shirts. Unlike Tony, mom bought all my clothes for me. I think it was her way of keeping me from following in TJ’s promiscuous, horny footsteps. She turned me into a nerd, alright. A wussy without a backbone. Too scared to stand up to my parents.
I pushed Tony’s gear aside to get to the lower shelf. It had an extensive collection of rugged-looking boots and sneakers, with some boxes on and under it. It cleverly concealed access into the crawl space from my parents. As I peered into the dark space, I saw some old, empty cardboard boxes. But behind them, I found Tony’s private porn stash. However, these were different from the books and magazines I had seen all those years ago. These were all graphicly illustrated gay magazines. Finding these sort of confirmed my suspicions about my brother. But was he really into guys? I knew that Tony was an oversexed fucker who did every hole he could seduce.
Sure, I suspected him of having sex with guys too. But I never caught him at it. All I saw or heard was him and his muscular mates talking and bragging. Their favorite subject was rude and rough sex with other guys. Not unlike the sessions my ‘friends’ and I had in the school locker room. But we mainly talked about sex in general. However, jerking off with them didn’t mean I was gay! Or was I? I started to doubt and struggle with my own feelings for a while.
Then, I dove back into the crawl space. Porn magazines were surely not the only thing that lay hidden back there. It certainly wasn’t. Hidden under a tough-looking classic biker jacket, I found an army-green duffle bag and a huge black dagger in a leather belt sheath. Man, I knew Tony was into anything army. But no, I would never have imagined this. I pulled the heavy bag and fucking cool jacket out and looked at them for a moment. After placing them on Tony’s bed, I crawled deeper into the enclosed space. Pulling out a couple of black plastic toats. I could not see what lay inside them, but the heavy boxes were laden to the brim.
I carefully moved all the gear onto the sprawling expanse of Tony’s king-sized bed. My eyes were immediately drawn to the ominous knife, its blade glimmering menacingly in the dim light. I quickly set it aside, recognizing the allure it must have held for a hardened bully like Tony. My attention then shifted to the classic leather biker jacket. It looked the way I remembered.
As I pulled the sturdy vintage black coat over my shoulders, a shiver ran down my spine. It fit me like a second skin. The contours hugging my form just right. Though the well-worn leather was a tad dusty. It had languished in the neglected crawl space for the better part of six years, after all. I could envision myself cleaning it, reviving the leather to its former buff glory with a bit of leather oil and elbow grease.
Peering into the mirror tucked inside the wardrobe, I couldn’t help but admire the cool reflection staring back at me. This was the look I had been aiming for. A combination of ruggedness and rebellion. This classic leather jacket infused me with a sense of confidence and toughness. Something I had always been missing.
The leather smelt, felt, and sounded amazing. I was getting hard just looking at my butch leather-wearing reflection. But, when I looked at my excited face — with the horn-rimmed glasses — my stiff cock quickly withered again. Mark Edwards had been right. These glasses did let my look down. A lot.
Going through the biker jacket’s many pockets, I found some thin leather gloves and a kinky leather cock strap with metal studs. As well as an old tobacco packet and some ancient gay-safe condoms. My 18-year-old bro must have been gay, I thought. Or at least bi-sexual to be carrying this shit around with him. To me, this was just another piece of the curious puzzle.
Snapping out of my deep thoughts, I wandered back to my brother’s king-sized bed. Opening up the first large toat marked ‘toys’, I got a pleasant shock. It was full of leather bondage items and sex toys in various shapes and sizes. By the time Tony turned 18, he had already bought up half the inventory of a sex shop.
Man, he had everything. From leather harnesses and cockrings to dildos and mastrubators. And whips and paddles to bottles of lube and poppers. I didn’t know he was into this kinky shit. And the discovery of more bondage gear, handcuffs, and rope made it clear Tony liked to tie up men.
I quickly looked through the other toat and the large army duffle bag. The duffle bag had more punk, leather, and camo army clothes. There was nothing too kinky, just some ‘normal’ daytime wear. But definitely stuff our parents would never have approved of.
I smiled as I pulled out a leather jockstrap and a harness from one of the toats. Wondering how the leather posing-jock would look on me, I slipped off TJ’s biker jacket and my shorts to try them on. With some difficulty, I put my dick through the hole in the leather jock. Snapping the leather pouch closed over it. I draped the sturdy X-harness over my naked shoulders and put on the leather jacket again. I pulled Tony’s leather baseball cap on my head to complete the look. Watching myself in the wardrobe mirror. This stuff was amazing!
The more I rummaged in the toat, the more excited I became. At the very bottom, I found über cool party clothes, including an old pair of ripped light blue button jeans. I put it on over the leather jock. It appeared that the seam around the buttocks was held close with Velcro. I usually hated button jeans. But I could see the appeal. “Easy access front and back,” I laughed.
I opened the Velcro and started playing with my butthole. Rubbing my hand over my bulge and fingering my ass. After a while, I even picked up a giant dildo and sucked on it a bit. Wondering what it would be like to suck a real cock. Smacking it against my naked butt a few times, I tried to put it inside my ass. It hurt like hell. So, I disappointedly abandoned the attempt.
It was well past midnight when I called Tony back. This time, I used my cell phone. Because Dad constantly checks the phone numbers I called. Tony and I had not spoken much over the past six years. He was a Marine now. But based near our hometown. I met him in town a couple of times. The last time we spoke, I had given Tony my new phone number. But he never called. We only texted back and forth a few times. I had kept it quiet from mom and dad that I had bought myself a cell phone. Just so they would not keep asking awkward questions.
I moved a couple of Tony’s sex toys to my room. I had not bothered to take off his incredible clothes. As I slipped into the snug fit of the kinky leather, I rapidly started to embrace the sensation against my skin, the weight and texture both thrilling and comforting. The classic black leather jacket, with its smooth, slightly glossy surface and subtle fragrance of well-crafted leather, had particularly captured my imagination. I felt like a million dollars in them, confident and bold.
These clothes formed the basis for the look I was going for, envisioning myself when heading out clubbing. Ready to take the night by storm and make an unforgettable impression. Discovering that I had a gay friend in the family turned this journey of self-discovery into something more exhilarating rather than daunting. Now, with Tony by my side, I felt empowered to explore my gay-curious feelings, knowing I had someone to turn to for advice and support as I navigated this new and exciting chapter of my life.
Ways and means.
“Ah, Brian?... I was wondering how long it would take you to call me back. Find anything... Umm... Interesting? Anything you would like, little bro?” answered Tony elatedly when I called him.
I just had to confront him. I had to know.
“Tony... Hi... Yeah, sort of. But... Umm... are you...? I mean — How come you got all those...?” I faltered.
I did not want to sound accusatory. I just could not find the right words. But Tony understood my question.
“Ha... Yeah. I am gay, Brian. Well, I was bi when I left home. But I got a boyfriend now... In fact, I just moved in with him. Nice guy... Nice and rough... Just the way I like it.”
Tony had a dirty grin when he talked. But I sensed he was just out to shock me a bit. Hoping for a response.
“Ah... Congrats buddy. It’s good to hear you’re doing well. Anyone I know?” I asked offhandedly, even though I knew full well that I did not know any of Tony’s friends.
“Glad you are taking this well, Brian,” my brother said. Relief oozing from his voice.
“Not fair, TJ... I am not our father! Why should I care whom you fuck. It’s none of my business. But hell yeah. I do like the stuff you’ve stashed away. Well, some of it, anyway. I am wearing your Velcroed stripper jeans and the leather biker jacket: some gloves, a leather jock, and a harness. Kinky stuff... I didn’t know you were into that shit. I didn’t even know you had it before you left us.”
This time, I could not keep the accusing tone out of my last remark.
“Ah... Umm... You’re right, Brian... I should have kept in touch with you. Sorry, bro... But back to the task at hand. You’re looking to get laid. Did you find the toy box?” asked Tony openly.
“Yeah... But my ass can’t handle shit like that. How the hell do you make them fit?” I asked worriedly.
“Awe, Brian, baby steps!... And plenty of lube — But are you really going to join my team? Thought you’re more of a womanizer,” laughed Tony, dirty.
“Well... Umm?” I blushed while the thought struck me, saying, “... I may as well try a guy. And if I don’t like it, I can always go back to the dark side,” I laughed back at my brother.
“... Anyway, Tony, do you know of any good clubs to get picked up at... Umm... No, wait!... Let me start at the beginning: What should I wear?... What should I do?... What should I say?... I have never been all that comfortable around women. But I really like to get laid. And if that’s a tough guy, like you, then that’s okay too. But I could not even get that black dildo to fit in my butt,” I replied worriedly.
Now Tony really started to laugh, “... Dude... That 16-inch fat dong is much too big for a virgin hole like yours! Start with something smaller. I left enough stuff to pick from. And as for where, what, how, and when... Well, that’s easy. Do you know the entertainment area at the south end of town? All you’re looking for you can find there,” my brother suggested hotly.
“... First, get yourself a haircut there. Don’t go to mom’s old hairdresser anymore. Go to Armando’s and tell Armando that TJ sent you. He’s an ex of mine, but we’re still good friends. Tell him you want a completely new look. He may act brutally tough, but he’s not... He’s a pussycat without the claws. Just let him do his thing,” Tony paused and waited for my reply.
“Okay... but why?” I stupidly asked.
“Brian, Look at yourself!... Mom picked your look. You’re eighteen now. Not the eleven-year-old boy she sees you as. It’s time to go for something appropriate for your age. I would say shaved up back and sides. And a butch comb-over-look with a side parting. And that new look needs to go with new clothes. If that leather jacket fits, you can keep it. But I would like those fuck-jeans back. Although... They do look nice over a pair of cowboy boots I left upstairs. You know, the black pair with the tough metal points. And as for the underwear. Go commando. No underwear saves much wasted time undressing,” gasped Tony, a bit more hornily. I knew he was picturing me dressed in his favorite leathers and jeans. But I had to hand it to him. I did need a new look.
Tony thought momentarily and continued, “... Oh, and be a good little nerd, Brian... Study!... Read every porn magazine and watch as many online vids as you can find. Take the box of toys and start playing to your heart’s content. If it hurts... More lube... Slowly work your way up to the real-sized man toys. I’ll be over Sunday after next to pick up my stuff. Oh, as for where to get picked up at? I suggest you go to ‘The Cottage’ or the ‘Mountain’... Best start at the Cottage. It’s a busy dance club for young men and women looking for some fun. There are multiple dance floors and a makeout area in the basement. The Mountain is a private men’s club with a dungeon. Not sure if you’re ready for that yet!”
“Okay... Got that... Thanks, mate... I am all excited. Tony? — Can I really keep this cool leather jacket?” I said shyly. Lovingly stroking the leather, making it creak.
“Does it even fit you?” asked Tony hotly.
“Yeah, I think it looks fucking cool on me,” I answered wheezily. Although it had room enough for me to grow into it.
“Fuck it, why not... I think I’ve outgrown it anyway. But I love to see you wearing it, bro,” Tony said.
“Ha... I’ll send you a picture,” I replied softly.
It went quiet on the other side of the line again. Longer than the other times. I knew what he was doing. Tony’s breathing became a little faster. It made me grin. I heard his grunts and something that suspiciously sounded like something wet hitting his skin. Apparently, Tony had been playing with himself while we talked. And the idea of me in his leather jacket and boots must have turned my brother on.
I asked him softly, “... Was that good for you, TJ?”
“Hell yeah!...” he replied, slightly out of breath.
“Well... Thanks for the chat, Tony. We need to do this more often. Don’t go to sleep just yet, though. I’ll send you a dick pic soon. Love you, big bro... Thanks for everything.” I said lovingly.
I had planned on taking only one photo. But after the first, I whipped my stiff dick out and took a few more. Heck, I even posed with the knife, wearing the gloves and Tony’s sunglasses.
The new look was impressive yet scary at the same time. However, this wasn’t me. Well, this wasn’t me yet. But I could see that I really needed to work on my appearance to stand any chance with the girls.
“Or the boys...” corrected my inner voice. I smirked as I shot my load over Tony’s bedroom mirror.
I sent Tony 3 of the hottest pictures. Tony instantly texted me back: “—Damn bro, That’s a hot look!... Have fun exploring this weekend. But be safe! Plenty of weirdoes out there... Text me if you have any more questions... Love, TJ.—”
< Continued in part 2 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.
