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]
If you enjoyed this story please visit my buy me a coffee page coff.ee/nakedderrick - it helps me write more stories.
____
While still asleep, I felt Daniel’s dick fully penetrate me. Instinctively I tried pushing away. His hard dick was almost nine inches and penetrated me deep, and I was still almost completely asleep.
To my surprise, Daniel placed his hands on my shoulders, which meant I could not escape. Even though I was the one who had come up with this idea, his dick in my ass felt intense, and my hole being stretched felt painful, like he was opening me up for the first time. I couldn’t believe I had set the whole thing up the night before.
Still half-asleep, I moaned and half-tried pulling away. Following my instructions, Daniel was determined to fuck me awake. I must admit the pain was pretty extreme, but once I got used to it, Daniel got into a really good rhythm, fucking me as I lay flat on my belly. My dick was hard as a rock from my morning wood, and I was pretty sure I was cumming hands-free.
As I started becoming more fully awake by the minute, the experience was intense but turned out to be a very pleasurable fifteen-minute fuck.
Afterward, I was extremely turned on and shaking. Daniel kissed my back and neck and held me as I shook from the pleasure.
After taking a moment to rest in each other’s arms, we knew it was probably late and time to get downstairs. I was still thinking and feeling everything that went into being fucked awake when Daniel spoke: “Your hole looks a little puffy and a little stretched, baby,” he said, rubbing his finger around my hole. I could feel what he was referring to.
To my surprise I saw Daniel reach for the phone which was on one of my small tripods and had captured everything. I could not wait to see my fans' reactions to this video and this made me get even harder.
My dick was still hard as a rock because I couldn’t stop thinking and feeling the intense fuck I had just had. The thought of being half asleep while getting fucked had been so hot. I was full of cum, and my hole was probably visibly wrecked and swollen. I was a little embarrassed and hoped not many guys were downstairs. My exhibitionist self, on the other hand, thought maybe more men seeing me hard and with a stretched hole would be hot.
Heading downstairs, it was unusually busy for the time. At 11:30 a.m. most people were usually gone for work, but being Saturday must have been why the place was still packed.
With my erection throbbing, I thought of heading for the bathroom to take care of it, or maybe heading to my bed, covering up, and discreetly waiting for it to go away. My third option was to walk directly toward Angel and Tom, who were standing by the coffee machine where about eight other men were having breakfast at the table.
Option three it was.
I could feel the looks from some of the men having breakfast. Angel acted completely normal, making eye contact with me, while Tom was visibly uncomfortable. We stood there having coffee, and we had so much to talk and joke about from last night. Tom was chatty and fun, although he would occasionally look down at my dick and make awkward faces.
My dick stayed hard for about twenty minutes and a drop of precum would occasionally hang down towards the floor until it tore off, Tom was not alone. Angel would also look at my dick from time to time, although he was completely unbothered and not embarrassed about it. On occasion he looked exclusively at it for a while. I caught some of the other men looking too. The ones who approached the coffee maker were unable to not look. Some stared the entire time, some tried to be discreet, but most of them managed a good poker face compared to Tom.
Overall we had a great time, filling Daniel in on all the guys we’d met, the drinks we’d gotten for free, and all the inside jokes we now had from the night. We also discussed some of the funny nicknames we’d assigned to certain characters. We had such a good time and just went on and on about it, laughing.
After a while we decided we should probably hit the gym soon. Angel and Tom went to get ready since they had already showered that morning, while Daniel headed for his towel and some toiletries, leaving me to walk directly to the showers where about five men were showering and a few more fully-dressed stood in the vanity area shaving, combing their hair or brushing their teeth.
While I was showering, I could feel a bit of murmuring behind me when my puffy hole became exposed as I slightly bent over to wash my thighs. The murmuring increased when I fully bent over to wash my ankles. At one point a moderate amount of cum shot out of my hole and started running down the side of my leg. Daniel had cum inside me multiple times last night and once this morning, and again I could unmistakably hear the other guys murmuring.
Rubbing my hole with my soapy hands to wash it, I could really feel what the fuss was about. Just as I was trying to wash it, my finger accidentally slipped in.
After awkwardly trying to air-dry myself by my locker (Daniel’s used towel hardly worked), I was bent over slightly, trying to decide what to wear. I put on a string, but I could feel it did absolutely nothing to conceal my puffy, open hole, also it was a little uncomfortable since it was so thin and tight. Angel approached me naked, holding a pair of shorts, and said, “Don’t think I didn’t notice that wrecked, stretched hole. It would be a shame not to let all the men in the gym see it.”
Acting surprised, I bent over further into my locker, spreading my legs and opening my cheeks with my hands. I could hear Angel snapping a few photos. Then I told him everything that had happened last night, and by the time I described in detail how I’d been fucked awake, we were both hard. Seeing the pictures of my hole did even more to get me hard, and I immediately AirDropped them to myself.
“Here’s a pair of white shorts,” Angel explained. “They’re a bit see-through when you bend over, they ride up right inside your crack, and they feature a pouch where you can put your balls and dick, acting as underwear. You don’t have to worry about wearing any underwear with these, and I’m sure your wrecked hole will be visible if you bend over at any point.”
Once I had them on, I could tell how tight they were, especially in the back. They gave me a permanent and unavoidable wedgie. Bending over a bit, I looked at Angel, who was hard, and gave a smile and confirming thumbs-up. I was so lucky to have made this special group of friends.
By the time I finished putting on my shoes, the rest of the guys were ready.
Daniel’s shorts kept getting shorter each day. Tom was in his usual baggy sweats and T-shirt, while Angel, to my surprise, was in dark grey leggings. They must have been the same brand as the shorts he’d loaned me, because the back was completely inside his crack, displaying his ass perfectly. It was as close as you could get to practically seeing him bare-assed, and I got a bit hard admiring his body and thinking my ass was just as exposed, if not more.
After our usual banter with the owner and our workout and abs routine, we had all finished showering. The only unusual thing during the workout was the looks I could see in the mirror as Daniel, honoring Angel’s request, had exclusively assigned us exercises that required us to be bent over in one way or another.
Reaching for my phone, I saw a message from Kai, who I’d be escorting tonight: “The opera and the restaurant we will visit tonight have a very strict formal dress code. Although I have negotiated our nudity, we are required to wear formal shoes and bow ties. Go to 6151 Richmond Street anytime before 5 p.m. Being one of the places I occasionally shop means nudity is allowed, and in this case expected, since I want them to get ALL of your measurements they will of course provide you with your shoes and bow tie. In return for your time I will offer you a special tip and will pay an additional $300 per friend who accompanies you completely naked. This means I expect you to arrive there naked and not carry any clothes or bags with you. We will make it $500 per friend if they also get their measurements. Remember I will be watching and will send the payment as soon as all of you are done with your measurements.”
I had planned on being naked indefinitely after the gym and felt so relieved removing my shorts, the last thing I planned on wearing for a while. In fact, I had not brought any clothing with me. We would rest from the gym on Sunday and had no plans that day. Tom and I would move into our new place Monday afternoon, where I’d try to avoid clothing and hope he’d be graceful on our first day. Maybe I’d tell him I was superstitious and thought it was bad luck moving into a new place wearing clothes or I would just ask him for a break on our first day.
Once Tom was in the bathroom stall changing and the guys were finishing drying off, I showed them the message, after telling them about my second escorting service today with a nudist who was extremely wealthy. After reading (and probably re-reading) it to make sure they understood, they both turned to look at me.
“Of course I’ll give you guys the full $500 if you decide to go and get measured,” I said. “This guy has paid me very generously already for my time and plans on tipping me well and offering to double my hourly rate if our time goes longer than expected. Since his payment has already hit my account, I can tell you he’s legit.”
We decided we’d go there after lunch. Looking up the address, we found it was about an eight-minute walk from the bar. Even though I was the only one with plans of walking naked to lunch, the guys opted out of clothing too, zipped up their gym bags, and draped them over their shoulders. When Tom walked out of the bathroom stall fully clothed and carrying his gym bag, looking confused and annoyed at the same time, he spoke: “Why aren’t you guys ready?”
Walking toward the door, I said, “We are. Come on, I’ll explain everything on the way.”
With three naked men and one fully dressed one, I must admit we garnered a lot more looks, and even a few whistles, honks, and banter from both pedestrians and drivers. I got my fair share when it was just me naked, but this time it was a lot louder.
Walking in, the first thing I saw was “Harness Guy” sitting at a big table alone. He looked surprised to see us, did a double take, and his eyes opened wider. “Why are all of you naked?” he asked.
As we all took seats around him, some of the waiters walked by to look at our bodies. Even though none of them were surprised, they were certainly impressed.
“How would you like to make an extra $500 in only one hour today?” I asked.
Harness Guy seemed quite intrigued, and I began explaining all the details for both him and Tom, since the naked walk had been so hectic.
After we learned Harness Guy’s real name, we immediately told him we’d be calling him Tom Two since we already had one Tom in the group.
Tom One had a look on his face like he’d just heard a meteor was headed directly toward Earth, although he wasn’t expected to be naked nor go and had no stake in the matter.
Tom Two began to speak: “Listen, ND, you’ve made me more money in the past couple of days than I’ve made in weeks, and I have no problem getting measured naked, but I do not want to get arrested for public nudity.”
“Nudity is not illegal in this city,” I explained carefully. “I’ve already verified it with the bar owner, who has studied this subject meticulously, and I’ve checked the laws myself. The law states that sexual activities in the nude and in public are illegal. However, it does not make any other reference to nudity. Technically, public nudity, as long as you are not engaged in sexual activities, is legal.”
Still looking a bit concerned, and seeing Angel and Daniel were interested in my explanation too, I continued, “We can talk to the bar owner if he’s here and he can confirm it, but if you don’t believe me I’ve been averaging about 23 hours a day naked the past few days and have walked to many places naked and never had a problem. As a matter of fact my last extended streak was only cut short because I had to wear that cop uniform, which I’m still finding a way to avoid.
Actually, after taking off my gymwear a short while ago I think I’ll be naked for at least the next 48 hours and have plenty of places I still need to go.”
“Gymwear!” Tom One sarcastically shouted. “You were in the shortest, most see-through white shorts that left nothing to the imagination. Every man in that gym was stalking us and many of them were secretly recording you, not to mention they were unable to avoid staring at you. I think your see-through g-string covers you more than those shorts.” Tom managed to deliver the last line clearly as a joke and made us all laugh out loud.
“Count me in, and yes, the owner is here. Today is payday. Did you not know? That’s why I’m here. Guest strippers get paid ahead of time but us regulars have to come in on Saturdays between 12 and 4 to collect, unless you have direct deposit set up,” Tom Two explained. “Here, let me take you to the office so you can get paid, then we can go to the locker room for me to put away my clothes and money and for you to put your payment in your locker.”
“Would you mind ordering lunch for me?” Not intending to address anyone specifically, I somehow managed to direct the request to all three of them and they unanimously agreed. I didn’t know who would decide my lunch order, but I trusted all three equally.
“Derrick, that was some show last night. My social media team got so many comments, tags, likes and reshares all at once their phones nearly crashed. I’m sorry I forgot to tell you about payday, but speaking to you, especially when you’re usually naked, feels so casual I often forget my responsibilities as your boss. I’m so happy Tom was here to tell you.” He handed me another envelope full of hundreds for the second day in a row. “I assume we can count you in to fill in as a go-go dancer on Thursday and we can have you as the headliner again on Friday?”
“Yes, you can count me in. However I have some ideas for my stripper act I’d like to discuss with you. What do you think about discussing these ideas in detail during my next photoshoot? When do you need me?” I replied.
“The sooner the better. How about tomorrow?” the owner suggested.
“Perfect,” I replied.
After thanking him and telling him not to worry about forgetting payday, I said I was happy he felt as comfortable around me as I did with him. I also thanked him for always letting me be naked and finally asked him to explain to Tom the stripper (as well as the guys at my table) that nudity was legal in town. Luckily he agreed and came out with some documents, which made everyone feel at ease. I could see Tom One especially relaxed, even though he was the only dressed one and not at risk.
In the locker room, I put my envelope in one of the bags of cash I was still keeping in my work locker for safekeeping. Tom Two stripped naked and put his clothes in my locker since he didn’t have his key. Once naked he said, “One of the strippers from last night just left after getting paid about ten minutes ago. Let me text him to come back right now.”
Back at the table the five of us finished lunch, and the stripper from last night rushed back. After Tom Two filled him in, he went to his locker and soon joined us naked.
“I am going with you. There is no way I’m going to let the five of you walk naked to this crazy measuring session,” Tom said in a non-negotiable tone. Even though he wasn’t the oldest, he was definitely the most proactive and wisest. He was a natural leader and we rarely argued when he appeared to be parenting us.
“Tom, thank you so much for wanting to look out for us, but let me check with the client first. He’s very particular with his requests. I need to make sure he’s okay with a clothed guy joining and that our pay isn’t affected,” I said, hoping Tom One would understand.
I texted Kai: “Hey Kai, I’m looking forward to my naked measuring session and have four more guys who are naked with me now getting ready to head over. My friend Tom wishes to accompany us however he is not comfortable being naked at all. On the contrary he is terrified of nudity. Would you mind if he joined us dressed? Five of us will walk there completely naked and get measured. Please let me know ASAP as we are planning on walking over soon.”
To my surprise I got an instant reply: “Tell your friend Tom I do not mind if he comes in dressed. However even though the five of you guys will get measured in front of the whole store naked and will be recorded, I will make Tom a special deal. He can be dressed all he wants however if he agrees to go to a private measuring station with only the tailor and his assistant where he is not seen by you guys or other clients and free of cameras. If he can strip naked and have his measurements taken I will pay all 6 of you $1,000 USD.”
Not wanting to speak anymore, I just handed Tom my phone. He read it and got quite nervous. After handing it back I showed the screen only to Angel and Daniel.
I could tell Tom One was having a complete breakdown. He even looked a bit pale. However Daniel, to my surprise, addressed him. While holding his hand he spoke: “You can come if you wish to see us through this. However even though we would all enjoy having our payment doubled, it is not your responsibility.” He whispered the last part so Tom Two and the other stripper wouldn’t hear.
“You do not need to decide now, and I know you are afraid of being naked in public. However if you went into a private room with a professional to take your measurements it does not seem so bad. None of us nor anybody else would see you naked. Just think of it like going to the doctor for a physical. Finally, it would be nice for you to have your measurements. Since you enjoy being dressed you could know your exact sizes and get clothes that fit you perfectly.”
Tom seemed pretty at ease after hearing Daniel. He felt he owed us nothing and wouldn’t affect us by coming along. He decided he would go with no promises of getting measured, but he was feeling more comfortable and seemed to be seriously considering it. Angel, using only body language, let Tom know he would be happy collecting just $500 and there was absolutely no pressure.
Once we were done, we took the walk to the address provided. To our surprise, seconds into our walk, rain started pouring like a monsoon. This somehow made the fellow pedestrians and drivers even more rowdy with five of us being naked and wet. Being naked, and neither of us carrying anything besides our waterproof phones, we did not care; Tom One, however, was getting his clothes drenched.
Upon arriving, both the tailor in charge and the assistant were fully clothed in very fancy suits and were waiting for us by the door with towels. The place was a lot bigger than I expected and extremely fancy. This shop had elegant carpeting, and every wall was covered by mahogany wood closets and shelves from floor to ceiling, with tons of very luxurious suits hanging by the walls. In the center there was a nice sitting area; small couches were spread throughout the entire place.
There were maybe about twenty male customers who were all dressed extremely elegantly. Worried about our health, they immediately welcomed us and handed us towels, taking special care of Tom. One man quickly ushered him to a fitting room.
“Sir, we know you are not comfortable naked. Please get out of your clothes and hand them to us so we can put them in the dryer, and we will provide you with a robe and a towel. We know your preferences, so on top of the robe here is a pair of boxers and boardshorts. Please get out of your clothes immediately and hand them to us and get into these,” the store manager said.
Tom rushed into the private room while the five of us naked guys used the towels to dry ourselves from the rainwater. Some of us laughed at the ridiculous situation we were in with the unforeseen extreme rain. Being naked was all in good fun, as we really didn’t care.
After Tom exited, dressed to his normal self and in a robe, the six of us sat down at a very beautiful sitting area.
“You brought the hottest guys; of course none of them compare to you,” Kai texted. I replied with the prayer emoji, showing gratitude for the compliment.
The fancy sitting area was very comfortable, and an employee brought out a bottle of champagne for us and a charcuterie board. After settling in, I noticed there was a big platform in front of a wall full of mirrors. There were some overhead lights, and on top of the usual surveillance cameras, I could see extra cameras directed towards this platform, which was at the center of the store. I could tell this was not the usual measuring area and had been exclusively set up for us.
After allowing us some time to calm down from our walk, the tailor politely instructed me towards the platform. The guys let out some laughs and playful whistles, which made me feel at ease. The tailor instructed me to stand still as he began taking all of my measurements while the assistant wrote them down.
The width of my bicep, my shoulder length, the width around my ass, my waist, my chest, thighs; then, after what I assumed were standard measurements, they measured both the thickness of my soft penis as well as the length, including the head.
After this, they asked me to get hard, and the assistant offered me a blow job in order to help me, which I accepted. Once hard, they measured my dick again, including shaft, head, length, and girth. I held my hands behind my head most of the time to make sure the measurements went along smoothly and were as accurate as possible. I could again hear my friends laughing, and when I would occasionally look at the mirror, I could see most customers were carefully looking at me, as well as a few men who were looking in through the large glass windows.
To my surprise and terror, they had been instructed to measure my asshole, where I had to mention the current state of my asshole was unusual since I had not only been fucked for hours throughout the night but I had also been fucked first thing. Although my asshole seemed to be getting slowly back to normal, it was still a bit swollen and open.
The manager had no problem sticking his finger up my asshole, and it seemed a lot tighter than it was this morning. “You are recovering quickly; however, I was asked to take your asshole measurements, so let me take those, and if you want to come back after a regular day and get new measurements, we can do that for you,” the tailor added.
I could not believe how hot this was. Once hard, I could not help but think I was standing naked, getting measured for a stranger who would know every inch of my body in front of my friends as well as plenty of strangers, not to mention we had not discussed the footage. I assumed it was exclusively for Kai, but I didn’t know for certain what he intended to do with it. Luckily, none of the other guys had thought to ask, but it was definitely something on my mind since that is how I made my living. If Kai did share it, it would probably benefit me, and the more content of me being naked for men to see, the better.
Once done, I playfully walked back to the sitting area. Being hard from the blow job, I stroked my dick and laughed as the other men continued to smile and giggle as well, of course with the exception of Tom, who still seemed a bit apprehensive. I sat down and took some champagne, although limiting myself to one glass in preparation for my service tonight. The energy was quite fun with the rest of the guys as they all eventually made their way to have their measurements taken in the exact same way. By this time, even the shoppers were admiring the show while becoming more playful and relaxed. When I had gone first, it was very quiet, and the tone of the room was quite serious, and mostly everybody was surprised at what they were seeing.
When Daniel’s turn came, and he was at the point of needing to get hard, I got jealous and shouted I would be the one fluffing him up. I got up, gently directed the assistant out of the way, and I blew Daniel’s dick to full hardness within seconds. My tongue carefully caressing his cockhead and a couple of sucks down to his base got him as hard as I thought he could get.
Taking a careful look at his dick, I was not surprised my asshole was in the shape it was, since Daniel was pretty long and girthy.
After getting back, I continued to enjoy a little champagne. Eventually, all of the naked guys went in for their measurements, all of them accepting a blow job from the tailor’s assistant.
I received a message that read: “You are all doing a great job; now it's time to see if Tom will double your pay,” Kai texted.
To my surprise, I think Tom had gotten a little buzzed from the champagne, and when we were all done, the tailor spoke: “Mr. Tom, we are ready for you in our usual private measuring room. Are you ready?”
To my surprise, Tom got up and followed them. As he did, we all began teasing and cheering him, which made him visibly uncomfortable. The measurement time was the same; however, when the door opened, we were expecting Tom One to come out. However, it was the assistant; he rushed over to another backroom, and we saw him rushing back to the private dressing room with an ice bucket.
After a while, both the tailor and the assistant came back out. With us being puzzled as to why this had taken so much longer, the tailor spoke: “Your friend was hard as soon as he removed his clothing, so we were unable to take the measurements of his soft dick. Since his dick would not come down, we had no choice but to dip his dick and balls in ice water, which worked for the most part, although I think he was still a bit hard. We had to move really quickly, as seconds after getting his measurements, he was hard as a rock again.”
I was handed a bag with my shoes and bowtie, was asked to go back to the mirror to try them on, and when we verified they fit perfectly, we all left naked, of course, with the exception of Tom One, who had had his newly dried clothes. Luckily, this time the sky was clear. Before I left the shop, 6,000 dollars hit my account.
After I took Tom Two to my locker and handed him his clothes, Daniel and I were overdue for a serious talk about Kai. After getting back to the bar and Angel, Daniel, Tom, and I were alone, I explained to Daniel my client just seemed like a rich dude who was looking for nudists just like him to hang out with, and he had said sex with him was optional and not important. If we did have sex, I promised I would picture I was having sex with Daniel the whole time. I had to admit I was not being completely sincere, as I had enjoyed spending my time with Dave (my first escorting service). I was not only looking forward to being naked in front of Kai, but if we did have sex, I would put my all into it.
After my first escort service and hearing Angel discuss how my videos made him feel, I had realized not only was I a nudist and exhibitionist, but I was placed on this earth to satisfy as many men as possible. I did not care what they looked like; I just wanted to leave them happier than I found them, whether it was just casually looking at me naked, touching me at the strip club, or having sex with me through Rentmen, also following me on my fans page where they had so much content they could watch of me being naked or engaging in sexual activities.
Daniel managed to put on a strong face, although knowing him, I could tell he was a bit upset but was coming around to my lifestyle. By now, he knew my body was for everyone to see and appeared a bit more relaxed, although I could see he was really falling in love with me. When the time came for me to leave, and even before that, I could see he was getting anxious, even more than me that had to get through the service.
With both of our schedules being the same today, Daniel walked me out with me wearing my shoes and bow tie and him in his short uniform, shirtless and in sneakers. Stepping outside completely naked, Daniel kept me company, and I soon saw a black luxury vehicle pull up next to me, and knowingly, Daniel opened the door for me and kissed me on the lips, saying his goodbyes.
The driver was wearing a classic chauffeur hat, tie, and driving gloves; besides that, I believe he was completely naked. I could not believe I was so close to meeting Kai. Even though I have never met him before, I felt completely at ease thanks to our correspondence. I was actually looking forward to meeting this handsome nudist.
If you enjoyed this story please visit my buy me a coffee page coff.ee/nakedderrick - it helps me write more stories.
After a long drive, we arrived at what appeared to be a very fancy part of town I had not been to before, not that my gay neighborhood was not as fancy, but this just seemed to be the fanciest of all places I had been so far in this new city. Well, actually, in all of my life, there was nothing like this in my hometown. We pulled up to a restaurant; there was a long line of fully dressed people waiting to get in, and after stopping the car right at the entrance, my naked driver stepped out, opened the door for me, and marched me right up to the receptionist, accompanying me.
I don’t know who drove the car out of the way. My driver had removed the hat and gloves, leaving him in his tie, fancy shoes, socks, and sock garters.
All eyes were on us; not only did it appear we were cutting in line, but both my driver and I were the only ones completely naked. After we reached the receptionist desk, my driver told me he would also be driving me home after the opera and rubbed his cell phone against mine, causing it to offer me the option of adding him as a contact. His name was “Your exhibitionist driver.”
The receptionist looked at us puzzled for a second but then realized why we were there. I was not only in a busy part of the city but fully naked except for my bowtie and dress shoes; at least a hundred people could see me naked. “Mr. Derrick, I am sorry for the wait time. Please follow me,” the receptionist spoke kindly as my driver gave me a surprisingly warm hug and disappeared out of the restaurant.
Following him inside the restaurant, which was by far the fanciest place I had ever been to. On birthdays, my dad would occasionally take Jeremy and I to the local Applebee’s, and we felt like it was the fanciest place on earth; this place, on the other hand, was extremely luxurious, and I could not believe I was here.
We eventually made it to our table, which was in a semi-private area. Kai stood up to greet me, and he was so handsome. I could not believe how lucky I had been to have such handsome men hiring me. He was a bit taller than me, in perfect shape, large uncut dick, beautiful blonde hair, brown eyes, and was truly captivating. I was quite impressed.
Even though he probably had a better command of the English language than me, he did have a slight accent which I could not recognize; however, I knew right away English was not his first language, which made this whole evening a lot more interesting. Even forgetting about the money, the incredible restaurant, the incredibly looking naked driver, and our plans for the evening, his accent was super captivating.
Kai’s looks would have anybody guess he was in his mid-twenties, but his demeanor was commanding. I knew for sure he was at least in his mid-thirties since I had read he was a self-made millionaire, and he carried himself in such a sophisticated fashion.
His smile was amazing, and while he was up hugging me and asked me to sit down, I hugged him a bit longer before obeying him. Even though he had been bossing me around today, the moment our bodies touched, actually, the moment I saw his playful smile, I felt like we were long term friends.
I had never met a man that looked like this, especially since I don’t think I had ever met a foreigner; his body was impeccable, and the tiny blonde hairs covering all of his body made me begin to chub up before I reminded myself I was a professional and he was my client.
Once the both of us were sitting down, Kai began: “I came across your fans page and X profile pretty much as soon as you launched it. I have watched all of your videos religiously and almost exclusively as I jerk off. You are so comfortable naked, and I love that about you.”
Feeling like I had to say something, I said: “Thank you, Kai; you are very handsome yourself,” I spoke sincerely. “I appreciate your kind words.”
Our fully clothed waiter poured me a very small amount of wine and then stared directly into my eyes. I was very confused at first but then, probably thinking of a movie I must have seen, I took a sip and gave him an approving look, which caused him to pour me half of a wine glass. After this, he began explaining the specials, which I would be lying if I said I recognized more than a couple of ingredients. I gave Kai a look which expressed to him I was a little bit confused and said I would have whatever Kai was having, trusting he would probably order something healthy judging by his prominent abs.
Once we were alone, Kai began speaking. “I was raised in a small town just like you, and I was a nudist from a very young age. I was always naked since I can remember, and then when I hit puberty, my parents had a talk with me about it. They approached me very delicately, telling me it was not a bad thing if that was my preference; however, it was not the norm, and if I wanted to be naked, some decisions would need to be made to accommodate me. I replied to them instantly: I prefer being naked, which they accepted. Testing me, they said even though I would need to continue wearing my uniform to school, nudity would be mandatory for me the entire time I was at home without the option of clothing. This included if they had family over for dinner or to use our pool, also if I decided to have some of my friends over for sleepovers or to swim. I of course accepted immediately.”
Kai continued talking about a conversation his dad had with him during this same exchange: My dad spoke: “One more thing: your nudity will also be mandatory during weekends and family holidays. Nudity is not illegal in Germany; however, some establishments may require you to wear clothing. Therefore, we will only visit clothing-optional resorts and camping sites from now on for vacations. We will look for dining and entertainment options which allow you to be naked, and the same will go for when we visit family during special occasions and holidays. This agreement will not change for the next six years until you are eighteen and attend college, where you will be old enough to make your own decisions. Are you absolutely sure?”
“Yes,” I agreed, even though at this point I had become a bit hesitant committing to being naked without the option of clothes for the next six years. Nevertheless, I agreed, and that same day, all of my clothing was removed from my room and thrown out; my school uniforms were moved to the closet located in the foyer for me to put on while leaving.
Not only did I completely relate to Kai wanting to be naked, but his commitment to nudity was impressive. Even though my dad was supportive and I was probably equally naked as Kai growing up, it was by my own accord. Learning Kai was not allowed clothing and had agreed to surrender it definitely made my dick chub up, and I was entranced.
“Did your parents follow through with your mandatory nudity till your eighteenth birthday, or was it just a bluff?” I had to apologize for interrupting him, but I needed to know.
Kai continued: “They did follow through. They were pretty strict with me, not only when it came down to my choice of being naked but also with making sure I had good grades as well as enrolling me in plenty of extra-curricular activities, not only in sports but also in the arts, having regular trainers and tutors teaching me a variety of sports and even piano, dance, and etiquette. Thanks to my strict parents, at eighteen I was accepted into a highly prestigious college. I had to get clothing for the first time, and at this point, my parents would no longer be involved, although whenever I came home during the summer and holidays, I would stick to being naked as usual.”
I was completely impressed, occasionally interrupting Kai to ask if he knew how to play the piano and the sports he had practiced. I couldn’t help but occasionally stroke my semi-hard cock. Even though every so often I would feel stares from the restaurant patrons and even the wait staff, who did their best to maintain eye contact while serving us, I was solely focused on Kai and his extraordinary story.
Kai continued: “During college, I opted for a dorm room. My first roommate was a complete prude, but he could not stop me from being naked the entire time I was in the room. After that, I began developing a community of nudist boys from college who would not only be my friends but we did so many naked dares outside of being fully naked every chance we could, which included our rooms with our roommates as well as the open showers.”
“I never went to college, but I have fantasized about being naked there,” I added.
“I left college nearly ten years ago, although I still am in touch with some of my friends and will reunite for naked vacations at least a couple of times a year. I have a couple of degrees, and in the past ten years after graduating, I have built an empire with a wide portfolio of investments. However, my main business are naked-mandatory resorts worldwide, flights, and tours exclusively for gay nudist men. Once I opened up my first resort and acquired my first jet, which was pretty much right after college, I have not worn a stitch of clothing for the past 10 years. I also have a fiancé who is not only a nudist but also exhibitionist,” Kai continued.
After this, I was blown away by Kai’s lifestyle. I could not help but feel inspired by this guy’s commitment to nudity, and hearing he did not own any clothing nor had worn any for the past ten years gave me hope that I too could accomplish this dream lifestyle. Not thinking about the money and solely focused on the nudity, I wish I too could one day get rid of the few clothing I owned permanently.
“Seeing your videos back when you launched your fans' page, I immediately felt a connection to you. Seeing you so free and what I imagine to be pretty much permanently naked besides the gym, where you did a great job wearing as little as possible, I really wanted to meet you. When you first started sharing some videos in the very city I live in, I was blown away. Then, seeing some videos surfacing of you from people secretly filming you, I could not believe my luck. I not only decided to hire you straight away, but I was in a private booth during your first strip show,” Kai said.
After thanking Kai for his kind words, I realized how truly exposed I was: any man could follow my naked journey, and due to how accessible I was at this time being a regular stripper at the local gay bar, as well as having people secretly filming me naked for the most part, any man who was in town could practically see me in person or hire me on Rentmen.
My mind was racing. I was still in shock picturing a young Kai agreeing to mandatory nudity for 6 years, having managed to keep with his nudity during college, and now being a successful businessman who had been naked for the past ten years alongside his fiancé.
I was also thinking of what I had accomplished and how men like Angel, Dave, and Kai had so much access to me. I could not imagine how many more men were following my journey and they too felt like they knew me.
At this point, Kai began enquiring about why I was in town, and just like Tom and Angel, Kai too had a way with words which made it super easy for me to express myself. Within very few minutes, Kai was completely up to date on every single person I had met the past week and what they meant to me, my jobs, my school schedule, my teacher’s name, my very young relationship with Daniel, and my future living arrangements.
“I am really enjoying your company. I am looking forward to the opera alongside you naked, and I would very much like for us to have a sexual encounter if we decide to. Even after the opera, we can just spend some more time together at the hotel I got for our date without having to have sex and just continue talking. I am sure whatever happens tonight we will have a great time; however, I have to confess spending tonight with you was not the only reason I hired you,” Kai said in an intriguing tone.
I didn’t need to speak; the look on my face portrayed my confusion perfectly.
“Please interrupt me if I am wrong, but I have a feeling you are feeling great right now. You have managed to remain naked most of the time since your arrival, have found the loophole in the city’s law, and have probably been seen naked by hundreds or maybe even thousands of men than would have ever seen you naked in your hometown. You will probably continue successfully headlining as a stripper, and it is only a matter of time before you will get recruited for additional shows in bigger venues. All of this is exciting for now, but deep down you are worried since you will soon be moving in with a roommate who, although very accommodating, will not allow you to be naked all the time. You are also dreading school, and even though you will probably continue your seminars where you will pose nude and will probably spend a lot of time naked in class, you will still have to get dressed for it,” Kai said.
He was absolutely right. I was riding high right now, but deep down I was worried about my future, and after hearing the option of nudity 24/7/365 was possible, I was even more scared of having to continue dressing for school, the gym, and even worse, at home. I wish I could permanently get rid of all of my clothes as soon as possible.
Not needing me to reply verbally, my face told Kai he was absolutely right about everything.
“I currently have well over one hundred employees in all of my businesses, all of them who are required to be naked 24/7/365 while working for me. Most are located worldwide; this includes hotel staff and tour guides who get to live in resorts which are naked-mandatory for guests and employees. Other staff members, like pilots and administrative staff members who live in town, must also be naked with no exception. I provide my local staff with naked housing, legal representation 24/7 should they ever get in trouble for being naked, as well as access to a small gym. With my local team growing, I am thinking of either purchasing or partnering up with the gym you currently go to, depending on the deal. It will probably be clothing-optional or nude-mandatory. The housing I provide is also in the gay neighborhood, and it is located in the sister tower to the building you will be moving into next week. It is identical, and I currently own a couple of floors which of course are naked-mandatory,” Kai continued.
I was so impressed, and this all seemed like a dream come true. Even though I was super excited and jealous of all of Kai’s employees, I could not help but imagine where I would fit into all of this.
“You do not have to decide anything today, but I would love to continue renting you on Rentmen at least a few times a month. Taking note of your schedule and knowing you are only required at school a couple of times a week, I would love to take you to all of my resorts worldwide. This alone would grant you employee status, where you would qualify for nude-only housing, legal support, clothing-optional gym access, and I could have Mr. Collins, your school teacher, agree to you being naked at all times during your school with one simple phone call,” Kai spoke so clearly and made such a compelling offer I was ready to agree to it on the spot.
The look of hesitation on my face was unmistakable; I could not help but feel like this was too good to be true.
Sensing this, Kai continued: “I would have loved to have somebody like me who understood my need to be naked when I was young. I dreaded all of my school uniforms, and adjusting to college was tough. I wish my full-time nudity had begun a lot more than 10 years ago, and I am able to make that happen for you. Not only will I enjoy taking you around the world naked, but I will enjoy giving you the opportunity to be naked permanently as I wish somebody would have done for me. I myself am happy just being naked; however, please correct me if I am wrong, but I think your need for nudity goes above and beyond. You have a need for as many people as possible to see you naked; every time a large crowd sees you naked, you want more, and I can also help you with that. You could be the lead model for my travel company; this would mean constant photoshoots at every location. You would be in thousands of worldwide gay magazines every month, paid ads online, social media, as well as be prominently featured on all of our websites.”
“You are absolutely right about me, and your offer sounds like a dream come true; however, I already have living arrangements, friends, and even what appears to be something very close to a boyfriend,” I said firmly while also looking completely entranced at the opportunities Kai was offering me.
“From what I hear, your boyfriend and friends, with the exception of Tom, would probably be delighted agreeing to permanent nudity. I can make a deal with them for photoshoots, and they could join us when we travel. I can easily get Daniel the tech job of his dreams and also work out a deal where he is allowed to be a naked employee. I can also get Angel admitted to the most prestigious dance academy in town, also with a nude agreement,” Kai said.
My mind was racing.
“I would really like to give living with Tom a chance,” I said.
“It is such a shame he is so uptight; his measurements reveal he has an incredible physique and an incredible cock. Maybe living with you can make him feel more comfortable in his skin, as I would love to photograph him nude alongside Daniel, Angel, and you, of course,” Kai said.
“This offer has no expiration date, so please think about it carefully and give Tom a chance. I know even though you may have to wear underwear occasionally, Tom will probably have so many friends over you will enjoy being the only naked person in the party, and that too can be fun,” Kai said almost with a cheerful smile.
I felt like he was reading my mind at this point.
“Let us finish dinner before we head for the opera,” Kai said with a wink.
I had almost forgotten the beautiful restaurant I was at with all this talk and the delicious food Kai had ordered. I was really excited about everything Kai had put on the table for me to think about; however, after having agreed to take some time to think about it, I needed to focus on being a great escort, and at this point, I began paying all of my attention to Kai, holding on to his hands, reaching under the table to rub his thighs dangerously close to his manhood, and continuing to inquire about his nudist adventures growing up, this time a bit more flirty and keeping constant eye contact with him.
This was a lot of fun, and before we knew it, we were in the car headed for the opera. Before getting in the car, I reached for Kai’s chin and pulled him into an intimate kiss which lasted a lot longer than either of us expected. Once we were in the car, the kisses continued as we both did not shy away from exploring each other’s bodies.
It was only a matter of time before I would experience the opera for the first time which excited me but I was mostly excited about spending some alone time with Kai.
If you made it this far please write to me with your story ideas at [email protected], follow me on X @nakedderrick or visit my buy me a coffee page coff.ee/nakedderrick - it helps me write more stories.
To get in touch with the author, send them an email.
