This series contains Gay Sex, Nudism, Exhibitionism, Bareback Sex, Double Penetration, CMNM, Gangbangs, Sex in Public, Fuck Machines and Toys. If material of this nature offends you or you are underage then you should not read this story.
This story is a work of fiction and any resemblance to persons living or dead, or to events that may have occurred, is purely coincidental. The author claims all copyrights in this story and no duplication or publication of this story is allowed (except by the websites to which it has been posted) without the consent of the author.
Even though the characters in this story do not practice safe sex, you should.
This story was written in the nude and you should get naked now before reading it. Feedback, recommendations for upcoming chapters, and nudes (aslong as you are of legal age) are much appreciated at: [email protected]
Please follow me on x @nakedderrick
Gus and I woke up at our usual time, well before 7 AM. Needing to rest my hole, I had worn my large butt plug to sleep—ironically, it’s my smallest.
Turning to look at Gus, I saw he was on his phone. Confirming what Chief Alvarez told us last night, he showed me the official press release.
"Entire city goes clothing-optional," read the major headline, with further details specified below. Every citizen or visitor had the right to be naked anywhere they pleased, both in private and public spaces within the city limits. Public sex was not allowed, except in private establishments that permitted it.
I asked Gus to hand me my phone, anxious to text John to check on him and confirm our next event. Thinking it was too early; I decided to email him instead.
"Hey John,
Hope you and Michael are recovering after the party. I wanted to check in and see if we’re still on for the next event. Do we have a date set? I want to be ready.
-Derrick
P.S. I got double fucked as soon as I got back to the hotel, and it was amazing! Thanks for the great idea. All that cum in my ass felt incredible, and the plug really prepared me for the two monster dicks I took."
I was about to give Gus his morning blowjob when, to my surprise, I received an email notification right away.
"Derrick,
I am so jealous you got double fucked. Michael and I are recovering and hope you are too. We’re on for the next event.
Actually, I’ve been emailing with the client. He wanted me to tell you he loved your hole. He said you were nice and open, yet still so tight, and really good at milking his dick.
He also mentioned your oral was the best he’s ever had. I debated whether to tell you that since I didn’t want to inflate your ego. But having fucked your throat myself, I must admit it’s hard to argue with him.
I’ll get in touch with you soon. Please don’t forget your hole training. I gave you two challenging dildos you need to use daily. Remember to practice squeezing them while taking them in. I know it can be challenging and painful at first, but it will get easier with practice.
-John"
I replied instantly:
"John,
Thanks for your quick reply. Yes, my hole is recovering, and I’m glad yours is too. To be honest, since I left your shop, my hole hasn’t had a break. But as of today, I’ll follow your instructions, rain or shine.
I’m pleased to hear the feedback and will make sure to continue making you proud at our next event. Looking forward to hearing from you soon.
-Derrick"
Taking a moment to reflect, I realize that two nights ago, I was gang fucked by a room of about 30 men who I never saw and fucked my ass and throat at least 41 times. Most of them were above average in size, making it a challenging and intense experience. The relentless fucking lasted over four hours, nearly five. I was tied up, blindfolded, and fucked mercilessly—and here I was, daydreaming about the next event.
It was my first time being a hole for a group of anonymous men, and I think I handled it well. Knowing John and Michael do it regularly, I was surprised to hear them complaining. John often screamed and begged for mercy, and even Michael occasionally told whoever was fucking him to take it easy.
I never complained, though there were many moments when I was pushed to my absolute limit and could have used a break or at least a normal fucking. Every single guy was extremely rough at all times and since there were so many of them, they would never get tired. What a night, I thought.
I reach over and kiss Gus. He smiles and instantly pushes my head down to his shaft. His dick is already hard, covered in a significant amount of precum, which I savor as I get to work.
"Since we have such a great deal back at our apartment, we should look into renting it for the going rate and use that extra money to supplement our income," Gus begins. "We can rent it furnished and since most of our personal belongings are just clothes, we can get rid of them. Charlie and Victor could help show the place for a commission, so we could do everything remotely."
Gus holds my head firmly, fucking my throat rougher than usual. I don’t know if he’s avoiding giving me a chance to speak or if he’s just horny. Either way, I enjoy pleasuring him. He’s right about our place—we could easily rent it without traveling back.
"The discount Jake gave us for eight weeks here is great, but we’ll need to talk to him. If he removes it after the agreed period, we’ll have to find a way to afford the full rate. I really love it here and would hate to find another place," Gus continues.
Gus pounds my throat deep and relentlessly. I struggle to keep up with his dick, let alone focus on these life-changing decisions.
"I start stripping at the restaurant tonight, and they say I’ll probably make decent tips plus a nice performance fee. I was also offered a stripping job at the nightclub, but I have to go later this week to work out the details with the owner," Gus says.
I know Gus’s mind is racing, and he’s doing his best for us. I also know he’s nervous about how I will respond. After sleeping on it, I’ve decided a few things. First, I never want to wear clothes again. Second, having sex in public is a lot more fun. Third, getting paid to have huge cocks fucking me up the ass and mouth is the best thing that’s ever happened to me. Moving here permanently is definitely something I want to do. Plus, there’s no way Gus would willingly go back to wearing clothes.
“Derrick, I was looking at our X account statistics, which I had neglected recently, and our followers have increased by tens of thousands. It looks like we've been tagged in countless videos from our week here, and most of them have gone viral.
There's a news report about us walking around town in our cock socks, with pictures and videos. There are many random clips of us in the city center surrounded by clothed men, you getting fucked by your massage therapist, and plenty of us naked in the nightclub. The most popular ones seem to be your double fuck from just yesterday.
We should definitely take advantage and start an official fans account. That alone could guarantee our financial stability for years. Also, it would be totally hot," Gus adds with a laugh.
Pushing my head down on his dick with both hands, Gus finally releases a huge load that almost chokes me. I guess he wanted to say everything without interruptions, or maybe he was too horny at the thought of never having to wear clothes again. Either way, I happily swallow his cum and lay my head on his legs, my tongue casually stroking his balls. Looking him in the eye, I tell him I'm down for moving here full-time and suggest that my sex work money alone could help us pay for this place, even at the full rate.
"I know you enjoy it, but at the end of the day, it's serious sex work. Taking that many dicks for hours at a time can't be easy. I also know the constant training and preparation you have to do for it, so I'd feel better if that money went into your savings," Gus says.
I tell him I understand where he's coming from, but sex work is something I enjoy so much that I feel like I should be the one paying for it. "Just think of your stripping—you get off on being seen and touched. It's the same way I feel about getting fucked," I explain. "Having a fans account is a great idea and will be a huge moneymaker for us, considering how fast we've gained followers. Once that takes off, we can quit our tech jobs. Hopefully, your stripping takes off, and I can continue doing my sex work as a fuck hole for rich men," I say with a smile.
"We've only been here a week and already have several sources of income to pull from. We've been naked 24/7 and loving it. I'm sure more financial opportunities will come our way," I say. Lifting my head off Gus’s crotch, I lay my body on top of him and reassure him that everything will work out. "We’ll get in touch with Charlie and Victor and find time to talk to Jack today," I assure him as we kiss.
"I love you," Gus says.
"I love you more," I reply.
Eventually, we quietly make our way to the vanity area, careful not to wake our roommates. Looking around, I notice there's not a single empty bed. Even Rodrigo’s bed is occupied by a couple. I reach into the locker under our bunk and grab my two biggest dildos and the gatekeeper butt plug Charlie gifted me. I also take a second to remove my butt plug and put it away. I've decided that while at the gym, I should work out not just my body but also both my holes—and who better to help me than Ricky?
While I get my stuff together, I glance over at Rodrigo and Sebastian as they sleep peacefully. I can never get enough of admiring their beautiful bodies. My dick gets a little hard watching them sensually spoon each other, knowing they are brothers.
Stepping into the sunlight, Gus and I embrace. We don’t need to say it—we’re privileged to enjoy this perfect weather, the ocean view, and, most importantly, not having to bother with clothing. Entering the gym, we notice it’s packed. I’m thrilled to see Ricky since I missed him yesterday, and the last time I saw him, I gave him a very sexy blowjob we both enjoyed.
Welcoming us with a smile while ordering us to warm up, Ricky takes my breath away with his beautiful body and handsome face. The gym is fuller than usual, with more naked men who appear to be trainers.
"I’ve been told I’ll only be training hotel guests from now on. Visitors can bring their own trainers as long as they pay the fee—and are naked, of course. This means I’ll have more free time for guests like you," Ricky explains.
Perfect. More time for Ricky to help with my new training routine. I glance around, noticing some very hot new trainers roaming the gym floor.
Looking at my bag curiously, Ricky asks, "I know you don’t wear clothes, so what did you bring?"
Handing him the bag, I begin explaining, "My naked body is one way I please men. That’s why I train my body. Most men, however, like to fuck me in the ass and throat once they’re done admiring my naked body. So, it only makes sense to work out my body and my holes while I’m here."
"What do you think? Can we incorporate some hole training into my workout?" I ask with a kinky smile.
Ricky, hard as a rock, says, "Well, I’d have to research some safe exercises, but I don’t see why not."
A huge drop of precum falls to the ground as he analyzes the dildos and butt plugs, I brought while eyeing my ass. Almost in disbelief those huge toys can fit in my ass.
"I’ve seen some videos online. Leg day is perfect for hole training. Squats alone make it easy to take a dildo or a butt plug as I squat. I can also take a dildo on some other leg machines. We just need to figure out how and where to secure them," I tell Ricky.
"Do your elliptical for 15 minutes, and I’ll do some research," Ricky orders, taking the bag.
Honestly, I’m a little nervous. These dildos are huge. John gave me one that’s 8 inches around and another that’s a real monster—9 and a half inches around and 14 inches long. The smaller one was challenging, but the bigger one was nearly impossible the time I tried them. The butt plug, which I hadn’t measured exactly, was probably around 9 inches thick at its widest point— ‘thickest part’—and the same length as the smaller dildo—8 inches.
After finishing our warm-up, Gus and I head to the leg area, where Ricky is waiting. He asks Gus to start on the hamstring curl machine and then move to deadlifts, he has already preloaded the barbell for him. He assigns him four sets of twelve on each machine—pretty standard.
I notice Ricky has also preloaded the Smith machine with weights, placed a bench underneath, and secured the butt plug to it with resistance bands. Very clever, I think to myself.
He instructs me to start doing a standard squat while he adjusts the bench to align with my hole. Sure enough, as I squat, I feel the tip of the plug pressing against me.
The plug is a challenge. I hesitate, but my legs start burning, so I have no choice but to push down, taking it all in. I can’t help but let out a painful scream both when the plug fully enters me as well as when it comes out since my hole is stretched on both occasions equally.
Ricky is right behind me, his hand on my shoulder. "You got this, Derrick. Great job. Let’s go for eleven more reps," he says.
I’m not sure I can do it, but Ricky’s encouragement helps. The plug is massive, and I cry out in pain every time. When I finish my set, I catch Ricky’s reflection in the mirror. He’s hard as a rock, precum flooding the floor. I also notice that most guests and trainers have stopped what they’re doing, staring at me in disbelief. When they see me looking, they quickly go back to their workouts.
"Great job, Derrick. Now let’s head to the leg press," Ricky orders.
Using a yoga block and another resistance band, he’s secured the 8-inch dildo to the center of the footplate. He suggests I take a wide stance to accommodate the dildo. Without adding weight, we test the position. The dildo, positioned at just the right angle, slides fully inside me thanks to the careful arrangement of the yoga block.
I let out a painful moan but am excited by how well Ricky is getting the hang of setting everything up. After adding my usual weight, Ricky tells me to go for twelve reps. I struggle but manage. By the last few reps, I’m even able to squeeze the dildo as it enters my hole.
Ricky stands to my side, his dick throbbing, more precum dripping to the floor.
“Great job, Derrick. Let’s go for three more rounds of these two exercises,” Ricky says.
As I get up again, I notice a lot of eyes on me. Most men are hard, and some are recording me. They quickly go back to what they were doing, trying to be discreet. I’m so used to it that it doesn’t bother me. Honestly, the attention gets my dick a little hard.
As we walk back to the Smith machine, I tell Ricky, “Remember, we’re training both my holes, and there’s no rule that it has to be a dildo. So, I should probably take care of this during our next set.”
I give his throbbing dick a playful tug as I speak. Then, I grab some paper towels, spray them with cleaner, and hand one to Ricky while taking one for myself. “We need to clean your precum before somebody slips,” I say with a playful smile. We both laugh as we head to the stations I’m using.
I continue my exercises. The dildo is manageable, but the butt plug is tough. I cry out in pain every time, but Ricky keeps encouraging me.
“Derrick, the blowjob you gave me last time was incredible,” Ricky says hesitantly. I notice him blushing, unsure whether to continue.
“Please, go on,” I say, placing a reassuring hand on his shoulder.
“I was actually hoping this time I could fuck you in the ass,” he says, unable to meet my eyes.
“Of course, Ricky. I consider you a friend, and you’re a great trainer. Look at the amazing job you’re doing with this crazy idea I threw at you. Actually, why don’t we do both? We can figure out another exercise where you can fuck me, and then I’ll blow you during our stretching session.
Honestly, I enjoy it. As my trainer, don’t hesitate to come to me anytime you want to fuck a hole or get a blowjob. I mean it, Ricky,” I say, looking into his eyes.
Ricky removed the dildos for Gus and set him up on the smith machine as well as the leg press assigning him four sets of twelve reps.
For the deadlifts he moved the preloaded barbell inside a standard gym cage and added a very thick resistance band horizontally at the exact height of my waist.
¨You will be doing normal deadlifts except I have added this resistance band to give you some stability while I fuck you, I will also be holding your waist to keep you still and if at any point you begin struggling with either my dick or the weight just let me know.¨ Ricky says
As I bend over with the resistance band right on my waist I can already feel the difference, it's almost like I am laying down on a bench. To my surprise, Ricky penetrates immediately before I even get a chance to grab the barbell.
“It may take me a while to cum, so I wanted to get started. You’ll do four sets of twelve, one after the other, with two-minute rests in between. My dick, however, will keep fucking your hole even during your rest,” Ricky says, now sounding more confident.
Ricky’s dick feels great as he thrusts in and out of my ass. He grabs my waist tightly, and I have no trouble maintaining my stability. He’s clearly a skilled top, hammering into me like a pro. I start moaning in pleasure, pre-Cumming. For a moment, I forget what I’m doing, then finally grab the barbell to start my deadlifts.
Once I finish my first set and put the barbell down, Ricky goes to town, fucking me like a jackhammer. Being so fit and strong definitely gives him an edge. The fucking is so intense in the best way possible and I feel an anal orgasm building. Ricky slows down a bit while I do my second set. As soon as I drop the barbell, he fucks me even faster, pulling almost all the way out before slamming back in—like a fuck machine set to 100.
Even though his pace is overwhelming, something inside me makes me look at him through the mirror. For reasons I cannot explain, I scream, “Faster, harder, deeper!”
He has no trouble obeying. The intensity sends me straight into orgasm, and I start Cumming.
During my third set, as Ricky fucks me with less intensity, I glance around the gym. About five men are filming, and most—including the trainers—are blatantly staring.
When I put the barbell down for the third time, I can’t imagine Ricky fucking me harder. But I’m wrong. Every time. You can hear his low-hanging balls smacking my thighs even through the loud gym music.
He somehow manages to push me into another orgasm, and I shoot a huge load. Once I finish my sets, Ricky keeps fucking me for another five minutes before blasting a massive load up my ass. The force feels like a fire hose shooting into my intestines.
As soon as Ricky finishes inside me, the men in the gym go back to what they were doing. We move on to more leg exercises, incorporating the smaller dildo and butt plug.
Reaching into the bag, I grab the giant dildo and tell Ricky, “I need to take this one for at least 20 minutes.”
Amazed by the size, Ricky asks, “How can you take a dildo so big?”
“Well, I haven’t taken it all the way,” I admit. “Last time, I only managed about three-quarters. But I’m not expected to fuck myself with it. I just need to get it in for at least 20 minutes a day and take as much as I can.”
Being black, very heavy, thick, and incredibly long, the dildo immediately caught the attention of the gymgoers. Ricky held it in his hands, carefully analyzing it.
“Since we’re done with legs, how about we try attaching it to the treadmill?” Ricky suggests. “You can start walking closer to the front of the machine, and as you’re able to take more of it, you can gradually shift toward the back. You can rest your arms on the handrails and bend over slightly—you’ll probably need to take it at an angle if you manage more than half.”
“Oh, my goodness, Ricky, since when did you become a hole-training expert? This sounds like a great idea!” I say excitedly.
“Since today,” Ricky laughs. “If you want to take it to the next level and really push yourself, we can increase the speed a little bit every minute. That way, by the end of your workout, you’ll be doing a light jog, and the dildo will stimulate your prostate nicely. It makes sense—your ass will get more used to it the longer you spend with it. What do you say?”
“Deal,” I reply with a huge smile.
“Okay, have a rest and drink some water while I figure out how to secure this monster to the treadmill,” Ricky says before taking off.
By now, the gym has emptied out a bit. I watch Ricky struggle to figure it out and after several failed attempts, he calls over two of the new gym trainers for help. As they gather, I take the opportunity to admire them—both are in fantastic shape, looking like they belong on the cover of Men’s Health. One is extremely muscular, while the other is just as sexy, beautiful brown skin and completely hairless from head to toe.
Gus comes over, letting me know he’s done and will be waiting for me at the spa. He gives me a big kiss on the lips and congratulates me on a great job before heading off.
Finally, using a tower of 45-pound weight plates and a barbell, the guys create a makeshift stand behind the treadmill. With the help of resistance bands, they secure the dildo in place. For added stability, they wrap more resistance bands around the base of the dildo, fastening it not only to the barbell but also to the treadmill’s handrails.
Ricky proudly slaps it to test its security, then calls me over with a grin.
I am a bit nervous, but I have taken this dildo before, and I can take it again. My hole has been getting stretched all morning, not to mention the pounding Ricky gave me along with what seemed like a week's worth of cum that will make for great lube.
As I approach the treadmill, the two other trainers stick around. I guess helping Ricky gave them the right to see this through. Ricky introduces them. The muscular one is Mike, who looks to be in his mid-30s. The sexy one is Tony, who is in his early 20s. My dick plumps up as I admire their sexy naked bodies.
I get on the treadmill and start backing my hole onto the dildo, but the pain is too intense. I try several times, but I can’t even get the head in. On my fifth attempt, Mike instinctively starts rubbing my nipples while Ricky rubs my thighs from behind.
"Come on, champ. I know you can do this," he says.
Taking a deep breath, I push back. The head finally pops in. I let out a huge cry and continue to cry in pain, the pain is so intense but instead of pulling away, I grip the handrails and focus on breathing for a couple of minutes until I adjust and finally quiet down.
"Okay, let's do this, boys," I say confidently.
Ricky starts the machine, setting it to a program that automatically increases the speed every 60 seconds. The sensation is intense, and I begin screaming. Ricky, supervising the dildo from behind, rubs my abs and whispers words of encouragement.
Both trainers, trying to comfort me, begin sucking on my nipples, one on each side of me. I really appreciate it, and I must admit—it helps calm me down.
"Ricky, can you grab the eight-inch dildo for me to suck on?" I ask. "Having a dick down my throat while getting fucked by a big one always relaxes me."
I start deep-throating the dildo. Ricky’s sensual touch, along with his words of encouragement and the trainers teasing my nipples, help my hole relax around the massive dildo.
Soon, I start taking more of it in. "Ricky, do you have your tape measure?" I ask. "I want to know how much I have left to take."
"Ten inches," Ricky replies.
Wow. I thought I was at least halfway, but I only have four inches in me. I let myself go a little more on the treadmill. The speed continues to increase every 60 seconds. We’re not even five minutes in, and I’m already struggling to keep up.
"Ricky, update?" I pant.
"Eight inches."
The pain slowly starts to turn into pleasure. I back up a little more.
"Four inches," Ricky reports.
I’m happy with that. Ten inches is a lot, and I’m satisfied. But now, almost ten minutes in, I’m really struggling to keep up with the treadmill’s high speed. Mind you, I am in my flip flops. I’m power walking, and the constant motion forces the dildo—ten inches deep inside me—to repeatedly stimulate my prostate.
Soon I start going into orgasm and barely manage to catch my cum. The orgasm emboldens me to take the dildo deeper, making my whole body shake as I enter a constant state of orgasm.
"Two inches," Ricky reports.
By the 15-minute mark, the machine is going so fast that I can’t keep up. Eventually, I push my ass all the way back using the dildo for leverage to keep up with the machine speed.
"Zero inches!" Ricky cheers.
The feeling of those last two inches is so intense that I keep Cumming, orgasming nonstop. Taking a moment, I put the dildo I was sucking down and looked around. I notice a crowd of at least eight gym goers jerking off—all of them filming.
Deciding to give them a show, I temporarily rest my feet on the treadmill’s sides. I push the dildo almost all the way out, letting them see how big it is, before taking it all the way back in. As soon as the last inch slides up my asshole, I start orgasming again. When I resume jogging, the sensation is overwhelming—almost like being on a fuck machine. Ricky’s touch, the trainers sucking my nipples, and the eight men watching me feels incredibly erotic. All eleven men are jerking off, watching me ride this gigantic dildo.
At minute 19, the machine is moving so fast that I can barely keep up. The dildo is so far up my ass that I can practically feel the fake balls against my hole almost penetrating me too.
When the machine finally stops, I slowly get off the dildo. I move to the treadmill next to mine, place the eight-inch dildo on the treadmill and sit on it, taking it all the way up my ass.
"Come around me guys, let me take care of those dicks for you," I tell the three trainers.
Taking Ricky’s dick in my mouth, I start sucking while stroking the other two. Eventually, I alternate, sucking each one. Tony cums first, then Ricky, then Mike. I take all their loads, carefully clean their dicks, and thank them for their help.
The men watching me start taking off as they begin cumming. I clean my cum off the treadmill while the guys dismount my dildo setup. I decided to keep the eight-inch dildo inside me for a bit longer.
I thank the trainers and turn to Ricky. "Tomorrow’s chest day. Maybe warming up with some push-ups while your dick is in my ass would be a good idea."
He smirks. "I’ll do some research."
After stretching with Ricky I head off to meet Gus for some spa time before we go to the lobby to discuss business with Jack.
After such an intense workout, I feel amazing. You know that good pain you feel in a muscle after a workout? That’s exactly how my hole feels—stretched way beyond what I expected, sore in the best way possible. My legs are equally sore. I Never thought I’d take 14 inches up my ass, but here we are—another milestone I proudly think to myself.
If you enjoy this story don’t forget to rate, it really helps me get more readers, especially chapter one.
