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
We step into the sex shop, laughing while I try to get Gus’s phone to turn off the vibrator.
Once inside, I immediately feel more relaxed. The store is a large rectangular room with the cash register on the left and the other three walls covered in merchandise from floor to ceiling. In the center, there are various slings, fuck tables, and similar items. There are also fuck machines and a few black leather ottomans, likely for customers to sit on while trying things or waiting for someone shopping. Every inch of space is packed with merchandise.
Behind the glass counter stands a beautiful young man wearing only a jockstrap, showing off the most perfect bubble butt. His warm, welcoming energy makes me feel at ease as he smiles and greets us.
Unable to hold the dildo in any longer, I walk up to the register and push it out.
“I’m sorry. I stupidly wore this giant dildo on a long walk, and I desperately need a break from it. Would you mind if I set it on the counter while we shop?” I ask.
With zero judgment, he replies, “Of course, no problem.” He takes the dildo and wraps it in a paper towel.
“Hi, gentlemen,” a voice says from behind us. “I’m John, the owner here. Welcome.”
“We’re sorry, we didn’t see you,” we reply.
The man looks to be in his late 40s or early 50s—very attractive, with black hair and a black beard. He gives off a sexy “daddy vibe,” his deep voice adding to the effect. He wears a tank top and cargo shorts. You can see there is a sexy body under those clothes, the result of years of going to the gym.
“This is Michael, my partner.”
“Nice to meet you both. I’m Derrick, and this is my boyfriend, Gus. We’re here on an extended vacation at the Nudist House Hotel and have heard great things about your shop.”
“We’ve heard about you too and have been expecting you,” John says.
“Really? We’re only on our fourth day here.”
“Well, you’ve made quite an impression on the team and guests at your hotel. And looking at what you’re wearing now, I can see why,” John replies.
“Can we get rid of these?” Gus asks.
“Of course,” John says.
With that, Gus unbuckles his cock sock, wraps it around his wrist like a bracelet, and starts browsing.
“Derrick, I hear you are hole training and may need some toys and help?” John says as he walks over, evaluating my dildo. Meanwhile, I take off my swimsuit and wrap it around my wrist.
After sharing my history, the toys I use, and my goals, John asks if he can make a recommendation.
“Of course. That’s why I’m here,” I reply.
Guiding me to a sex table, he asks me to get on all fours. He puts on a glove and slides one, then two fingers inside me.
“I can feel you’re well-lubed, which is great. Hold on here,” he says.
“Gus, would you mind coming over? Have you ever worn a cock ring?”
“Not really,” Gus answers.
Digging behind the counter, John grabs a small transparent item and gestures to Gus.
“Would you mind getting on top of the ottoman?”
For Gus, the more exposure, the better. He happily hops on, positioning his dick at John’s eye level.
With one swift move, John slips the cock ring on him.
“This is a vibrating cock ring. It should be quite pleasurable and get you hard in minutes,” he explains.
“Or seconds,” John adds, surprised as Gus stiffens almost immediately.
Reaching for a tape measure, John checks Gus’s size.
“6.9 inches around, 9.6 inches in length,” he announces. “Thank you, Gus. You can get down now. And congratulations on a beautiful dick.”
“That cock ring should keep you aroused and feeling good for a while.”
Reaching for a dildo from the shelf, John asks me to breathe and relax my hole as he pushes it in about 9 inches deep. I feel very stretched but quickly relax.
"How do you feel? Do you think this is comfortable for you to wear for a couple of hours?" he asks.
"I feel quite full and stretched, but I think I could do a little bit bigger," I reply.
"Good," John says. Grabbing another dildo, he asks me to relax, and before I know it, it is 9 inches deep.
"This one is really stretching me out. I don’t know if I can keep it in for long," I explain.
"Let’s try leaving it in for ten minutes," John says.
Turning back to Gus, he asks about the cock ring. Gus says he loves it. They talk about how cock rings can make his dick a little bigger while he’s wearing it and that he should consider using the vibrating one while fucking me. John thinks we would both enjoy it.
He also recommends another one that Gus can wear for a few hours a day when he wants to show off a bigger soft dick with pushed-forward balls.
"I’d recommend fully transparent ones—you wouldn’t even be able to see them," John adds.
"Of course," Gus says, all ears. "I’ll try another one when I’m done enjoying the vibrating ring."
After ten minutes, John asks how I’m feeling.
"I’m more relaxed, but I feel like I’m at my limit," I say.
John explains, "This is 8-inches in circumference, which I believe is your baseline. I recommend wearing an 8-inch wide by 8-inch-long dildo for at least a couple of hours a day when you can sit and relax. The feeling will be intense at first, but over time, you’ll get used to it and be able to wear it for longer."
He then pulls it out, grabs a huge dildo with balls and a suction cup, and asks me to relax my hole and slowly back up onto it at my own pace.
Being a complete monster, it takes me forever to get the head in. I manage to take it less than halfway. He then pulls it out slowly, places it on the table, and asks me to sit on it.
This time, it’s a little easier. I go down about halfway.
"Hold it in place," John instructs. "If you can get further down, go ahead and do so with no pressure."
"This is 9.5-inches in circumference and 14 inches long. Since it’s 1 and a half inches above your baseline, it’s what you should always be working towards. I want you to sit on this dildo at least twice a day for 20 minutes each time and take as much as you can."
I am so turned on hearing the dimensions and the progress John wants me to make.
"You don’t have to ride it—just get it in and hold it in place. I believe you’ll quickly get comfortable with it and start riding it. Hopefully, we can advance your baseline to 9 or 10 inches around," John says.
After a few minutes, I lower myself about three-quarters of the way. The intense sensation makes me start precumming.
Gus is so turned on by the vibrating ring that he asks if he can fuck me. John tells him to give me five more minutes on the dildo.
After the time is up, I get off the dildo and lie on my belly, spreading my knees and opening up my hole for Gus with my hands. John comes over, sticks two fingers in, and explains how my hole is open but still tight enough for Gus to have a great fuck.
As Gus pushes his full length inside me, John holds his hips in place and asks me to squeeze my hole four times. He then asks Gus how it feels. Gus only moans in response.
John instructs me to squeeze every time Gus is all the way inside. He tells Gus I should be squeezing harder each time, making it feel even better. I can feel the vibrating ring in my hole and it does feel extra pleasurable. Sure enough, Gus begins moaning louder with each squeeze. Within minutes, he shoots an unusually large load.
John congratulates me and explains that the purpose of hole training is to keep me open enough to take any dick comfortably while staying tight enough for pleasure.
As I thank him, I spot a dildo on the wall that looks exactly like Sebastian’s dick with its big head. I ask John about it and mention that I have a friend with a dick like that. I love how just the head going in and out feels amazing.
John nods and asks if I want to spend fifteen minutes on the fuck machine with that dildo. “With the right stroke length and position, we should be able to recreate what you’re talking about. It should feel great.”
After cleaning Gus’s dick, I ask if I can get on the fuck machine. “Of course, you can,” he says, bending over to kiss me.
As John sets up the machine, Gus tells him, “Your partner has a beautiful ass.”
“Michael has a great ass. I’m sure he’d love for you to fuck him,” John replies.
Looking into Gus’s eyes, I tell him he should. “I’ll be on that fuck machine,” I say.
By this time, Michael has approached. He starts stroking Gus’s dick, then lays down on a sling.
“Wow,” I whisper.
Michael has a beautiful hole. He signals Gus to wait while he pushes out what must be a ten-inch circumference by nine-inch-long dildo from his ass. He then puts it in his mouth, giving Gus a wink with his asshole.
John asks me to get on all fours again. I feel him fastening what feels like a seatbelt around each of my shoulders, preventing me from leaning forward. Then, I feel restraints around my ankles.
The full head of the dildo presses against my hole and then John pops just the head in. The sensation is amazing as my ass is around the thinner shaft, relaxing my hole. As I hear the loud motor of the machine powering up, I feel the dildo pull out so that only half the bigger cock head is inside me. Instantly, only the head pushes back in.
“Oh wow, this feels incredible.” Every time the head is fully inside, my hole relaxes, and when it pushes out, it stretches me again.
Only the head of the dildo is penetrating me, but the frequent stretching feels unbelievably good.
“Did we hit the nail on the head, Derrick?” John asks.
I can’t even answer. I’m in ecstasy.
He places the controller under me. “We’re at 30/100,” he explains. “You’re free to increase the machine speed.”
He also tells me that even though I can’t pull away, he encourages me to push back and take the full dildo to the base every few minutes. “That way, you’ll work your second ring, which can be even more pleasurable.”
I’m in heaven, fantasizing about Sebastian, moaning, and precumming like an open faucet. Then, I hear Michael moaning. Even though he’s out of my field of vision, I know Gus is enjoying himself.
I ask John to come in front of me. He shows me a video on his phone of my asshole taking the fuck machine.
“Wow, it looks great. I love the way my hole looks when it is getting stretched.”
I tug at John’s pants, and he happily pulls out a huge cock, which I immediately take down to the base. Taking a little time to notice, John’s body is incredible with washboard abs and muscular legs.
I’m completely lost in pleasure when John suddenly pushes me back. In the same motion, the cockhead penetrates me deeply, making me shake in ecstasy and precum even more.
After a few minutes, I return to my original position. John adjusts the speed to 50/100. The difference is intense. When I push back, I start cumming hands-free, caught in an endless orgasm for most of the session.
After about twenty minutes, I reach 70/100 speed. As John cums down my throat, we turn off the machine. I’m shaking uncontrollably, my open hole on fire.
When the machine stops and I come back to reality, I see an audience—Taylor, Gus, and the two chefs—all naked and stroking.
I turn to my right and see Steve fucking Michael on the sling.
“Wow, what an experience you had there, my friend,” Taylor says.
“Oh, it was incredible, Taylor. You have to try it sometime.”
The chefs speak up. “Can we each have a go at your ass and mouth?” they ask Gus and me.
They explain that since they’re both verse, they’ll let Gus fuck them in return.
Being as much exhibitionists as us, they each bend over, spreading their cheeks to show off their beautiful holes.
Gus manages to say, “Sweet.”
I guess they’re each about eleven inches hard, with a seven to seven and half-inch circumference.
“What do you say, guys?” one of them asks.
Their cocks are stunning, and they’re incredibly sexy. Dining at their restaurant every night and seeing them naked, I’d be lying if I said I hadn’t fantasized about them fucking me.
So, I ask, “What are you waiting for?”
As the guy’s approach, I notice John, Gus, and Taylor heading over to Michael. Knowing they will keep his ass and mouth busy; I focus on Carlo’s cock in front of me while Tony gives me a rim job. The feeling of his tongue working my asshole is incredible—a much-needed treat after all the punishment my hole has endured in the past hour.
Wow, these dicks are beautiful, and I am in ecstasy taking Carlo’s dick down my throat. Being Italian, he is very verbal, and that sexy accent is a huge turn-on. Although, the beautiful dick alone is enough to make me commit to giving him some great head.
As the rim job comes to an end, I remove the shoulder restraints to lay flat on my belly. Since my ankles are still restrained to the table, my legs remain wide open. This position is my favorite—I feel dicks penetrate me deeper, and I have zero control, which feeds my submissive side.
Reading my mind, Carlo grabs my wrists and stretches them to each corner, where wrist restraints are readily available. Now fully stretched and tied to the table, I can’t help but feel both nervous and excited at the same time.
Soon enough, I feel Tony climbing onto the table. His cockhead presses against my asshole, catching me by surprise as he aggressively slams his dick all the way in. I scream in pain, even with Carlo thrusting in and out of my throat.
Regret washes over me. Tony remains fully inside, pressing his body against mine until the pain dulls and slowly turns to pleasure. Then, pulling all the way out, he slams into me again. I scream, unable to hold back. He fucks me mercilessly at a slow pace, and just as I regret agreeing to this and putting myself in such a vulnerable position, an intense wave of pleasure builds inside me. I orgasm hands-free for the fourth time today, my hole tightening around his cock.
Feeling more relaxed, I can now hear them moaning and talking. Even though this fuck is intense, I’m starting to love every second of it. I fear Tony will cum soon, but to my surprise, they switch places. I secretly hope Carlo will be just as merciless.
With the same intensity as before, he shoves his dick down my throat. I feel Carlo’s cockhead press in, and sure enough, he slams his dick deep inside my ass. The pain returns—his dick must be slightly longer. Not only is it longer, but he is rougher and faster than his boyfriend.
The intensity is overwhelming, so I focus on Tony’s dick. Completely immobilized, I can’t push him deeper down my throat, so I use my tongue and tighten my lips around the base to signal I want him deeper. Luckily, he catches on, leaving his dick deep in my throat for a few seconds each time he thrusts.
This comforts me, momentarily distracting me from the brutal fuck I’m receiving. Eventually, my hole adjusts, and I surrender to the pleasure once more.
The chefs switched again, and Tony now felt fantastic compared to Carlo. After switching a couple more times, Tony came deep inside me, and I tightened my asshole around his shaft to squeeze every drop of cum. He then switched with his partner, and I cleaned his dick off properly, savoring the sweet taste of his cum, keeping his softening cock in my mouth. I felt Carlo was close, and sure enough, he slammed deep one last time, and he came so much I felt some of the other loads I had collected overflow.
When he pulled out, he rubbed his dick around my asshole, collecting the cum that overflowed so he could feed it to me when I cleaned his dick. Tony collected more cum from my asshole with his fingers and rubbed it on Carlo’s still-hard cock, then gave me a very soothing and much-needed rim job, licking my hole clean.
When the cock was clean, and the guys finally finished with me, they released me from my restraints. I noticed Michael was no longer on the sling. I guess I lost track of time. As I got up from the table, I noticed Taylor and Steve lying on an ottoman, completely spent and satisfied after fucking Michael. Then I saw Michael and John by the cash register, handing Gus the big bag of toys and his receipt.
The chefs, returning to the polite manners I knew them for, helped me up. Each gave me a kiss on the lips and told me I was the hottest fuck they’d had in a long while. They hoped we could do it again.
Without bothering to stand up, Taylor said, “If Derrick is not available, I will happily take his place. That was super-hot.”
The chefs started putting on matching speedo-style swimsuits, a very sexy European cut. Taylor put on a white speedo, and Steve wore a green and yellow string bikini that exposed most of his ass and barely covered his manhood. Gus and I put on our cock socks, and Michael handed me my dildo. I said, “There’s no way. I definitely need to put something in my ass to hold in the cum loads, but I can’t walk with that thing.”
John hands me a very comfortable-looking butt plug with a tiny clear base. The base consists of two curved ¼-inch by one-inch sides that fit vertically. When the plug is positioned deep inside, they are practically undetectable to the naked eye, even more than my swimsuit. John says I can borrow it, or if I like it, I can pay for it later. It is probably close in size to what I would normally wear, but it has a weird shape I’ve never seen before. However, my asshole swallows it in fairly easily. I bend over completely in front of the guys to make sure everyone agrees I can get away with it.
I hear five “perfects” simultaneously. After we all say our goodbyes to John, the six of us leave. Of course, within seconds of stepping onto the street, Gus and I became the target of teasing from the guys, especially the chefs, who in this setting were showing their true personality.
I blushed and felt exposed because of the teasing. It probably made me feel more embarrassed than the tens of people on the street who stared Gus and me down when they walked by. Gus was for sure loving every second of the attention from both our party and the people on the street. I’m sure he was looking forward to crossing the main street, which at this time would be packed. Some of the jokes about our suits were really funny, especially the ones from the chefs. Eventually, the six of us were laughing out loud.
Reaching the door to our hotel, the chefs said they needed to go prepare for dinner and asked us to come by at 7 for a special dinner on the house. Rushing inside the property, Gus immediately took off his swimsuit as we were still discussing our plans. Today was Thursday and we had agreed to go to the gay nightclub. We agreed to come to the restaurant at 7 and decided we all needed naps before dinner. The chefs went towards the restaurant, Taylor and Steve to their private room, and Gus and I headed for the showers before heading to our shared bedroom space.
Gus put all my toys away and asked me to remove the plug to replace it with his dick for our nap. As we were drifting off to sleep, Gus told me he was so proud of me for everything. He kissed me gently on the neck and said, “I love you.” Without even thinking, I said, “Me too,” and again fell asleep to Gus kissing my neck.
