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It all started around that time of the year when people would contemplate their plans for the summer. Somehow, my little sister and my parents came up with the idea of going on vacation together. For me, a guy in my mid-20s, it was shocking news. At first, I was hoping those plans would fall aside but that didn’t turn out to be the case. And by the beginning of summer, it was clear that the four of us would spend an entire week in August in and around a small apartment near the beach.

Following a 10-hour drive from central Europe to the Mediterranean coast of Italy, we were greeted by an almost cloudless sky and pleasantly warm temperatures as we parked next to our accommodation and unloaded our luggage. The sun was already well beyond its zenith and a cool breeze coming from the sea made it really comfortable outside. Still, I wasn’t in the mood to soak up the vacation vibe. We were given the key for the apartment and started dragging our suitcases inside. The apartment looked nice and clean but it was far from spacious. There was really only one room, a kitchen corner and a sleeping area with a double and two single beds that were barely separated from the rest of the apartment. The bathroom was also very small and only contained the most necessary equipment: a sink, a toilet and a shower.

After having inspected our accommodation, we decided to explore the area where we would spend most of the coming days. We also needed to get ourselves some basic food before gonna the beach to watch the sunset and to relax from the long drive. I had to admit that we could have ended up in much worse places, yet most things about this vacation kept feeling wrong for me. I spotted couples who were kissing each other lovingly and girls in tight bikinis attracted my eyes, only to realize that I would be stuck with my family for the next week with almost no privacy to myself in our little apartment. I figured out that it would be better not to give in to those sort of temptations that were presenting themselves right before my eyes, since being horny always would certainly not help improve my situation. Frustratedly, I trudged through the sand towards the beach bar and ordered myself a cocktail.

Obviously, my grumpy behavior was noticed by the rest of my family. When we returned to our apartment around 10:30 at night, the inevitable question came up. “What is wrong with you? It’s so nice here and you’ve been in a bad mood all day” my mum asked me. For a brief moment, I wondered about saying something like “I’d rather hit on hot girls instead of hanging out with my parents” but I quickly dismissed that idea. “I’m just not feeling it. I told you in advance, this was not a good idea” I replied instead and tried to break out of the conversation. “We’re all tired from the trip. Let’s not discuss that right now, please.”

The next day began like the previous one had ended. The joyful voices of my family and the exuberant mood that was in the air felt like pinpricks in my body. Still half asleep, I realized that my sister was trying to convince me to go to the bakery with her and our parents to get something for breakfast. “I don’t care, just get me anything and I’ll be fine” I mumbled and buried my face deep into my pillow. But my sister was having none of it. “I was already talking to Mum about you this morning” she said as she angrily ripped the blanket off my body. “We won’t let you spoil our vacation like that.” I wasn’t keen on risking big trouble on our first proper day so I gave in. While getting ready and dressed, I looked at my phone screen in disbelief. “It’s seven o’clock! Are you guys alright?” I asked. But no one bothered to react to my opinion. “Come on, let’s go” my dad urged me as we went out into the streets.

There was a small bakery only a couple of blocks away. Sluggishly, I followed my family inside. Two other customers were standing in the narrow space between the door and the counter. One of them was a woman about my age. As she walked out of the door, our eyes met for just a brief moment but that was enough to completely change my mood. It was as if time stood still when I noticed her admirable beauty. She was just a tad shorter than me, with shoulder-length light brown hair and bright green eyes that enchanted me at first glance. Her outfit was casual and revealing but not unusual for a warm day on vacation at the beach. She was wearing short jeans which barely covered her well-rounded butt and her turquoise, low-cut top clung tightly to her perfect upper body, emphasizing a sizeable cleavage as well as a breathtaking waistline.

Although we hadn’t exchanged a single word, I couldn’t stop thinking about her. As I spent the morning at the beach with my family, I was careful not to let my sudden change in mood show to them. Instead, I tried to make it seem like I was slowly acclimatizing and beginning to like this vacation more and more as time went on. But in fact, for most of the day my thoughts revolved around how to see that woman again and maybe even talk to her. In the evening, I finally managed to put a plan together. My family must have noticed that my mood had improved significantly over the course of the day and I was looking to take benefit of that. I apologized for my grumpy behavior and offered to get everyone’s breakfast from the bakery as compensation so that they could sleep later the next morning. It worked out as intended but I knew that this was just the easier part of the plan. I still had to make sure to be at the bakery around seven o’clock and hope that the woman I met there would stick to her daily routine as well. Just to be safe, I set an early alarm on my phone before gonna bed.

I had a rough sleep that night and woke up well before the alarm. Trying to calm my nerves, I spent a few more minutes in my bed and listened to the steady breathing of my family members which all appeared to still be asleep. Then, I snuck into the bathroom to shower and to brush my teeth. I grabbed a fresh shirt, some money and left for the bakery. My timing was pretty much on point. “There is no way this is going to work” I kept telling myself until I reached the bakery and saw her inside. My heart was pounding when I nervously opened the door and lined up in the queue behind her. Just moments later, she turned around. Her friendly smile assured me that she recognized me after our brief encounter on the previous day.

“Good morning. You’re alone today?” Immediately, I noticed her distinct British accent. “Umm, yes, I woke up early so I decided to get breakfast for my family.” I enjoyed that I could present myself as the dutiful and accommodating son that I absolutely wasn’t. “Honestly, I didn’t expect a guy your age would go on holiday with his family but when I think about it, there’s something appealing to it.” “Well, I wouldn’t call it appealing and I’m not really thrilled about it, but I was outvoted on that idea. Let’s put it that way. Who are you here with?” I asked. It felt like I was just waiting for the word “boyfriend” in her answer as I already began to think about the best way to get her out of my head over the next days. But her response turned out to be a positive surprise. “I’m here with my best friend. She likes to sleep late so it’s on me to get the breakfast.” I was even more surprised when she appeared to be waiting for me after being handed her pastries. “What is it that you don’t like about spending time here with your family?” she asked me while I grabbed my bags from the counter. “There’s nothing specifically bad about it” I said. “It’s just the thought that it might be more fun to do something else.” “Ah, yeah, I see. Do you have any plans apart from what your family is up to? Maybe I could join you” she said with a smile. At that point I was just scrambling for the next best thing to say in order to keep the conversation going. “Hmm, I saw that there is a karting track nearby, …” I paused. “What am I doing here?” I wondered to myself. “Why don’t I invite her to a restaurant? Or go shopping with her? Buy her clothes, shoes, jewelry or whatever she wants. But no, I have to talk about karting instead!”

Once more, she reacted very differently than I would have expected. “Oh, cool, I didn’t know that.” “Are you really into such things?” I asked her a little confused. “I’m not super into it” she admitted. “But most men in my family are. So maybe it would be a great opportunity to try it out.” “How long will you still be here?” I wanted to know. “Just three more days” she said. “But on the third day from now, we have to leave really early for our flight home.” “Oh, that’s not a lot.” I was struggling to hide my displeasure about her response as she took the initiative. “Yes, I guess we shouldn’t waste any more time then. How about we go karting this afternoon?” “That would be great” I responded, slightly wondering how I was still able to talk. “But what about the friend you’re here with?” I asked cautiously. She was quick to brush my concerns apart. “Don’t worry about her, we’ve done enough activities over the past few days. I’ll find an excuse to spend a few hours with you.” “Okay, so we could take the bus to get there, it’s only a 15-minute ride” I suggested. “Let’s meet at the bus stop at 3 pm. Would that work for you?” “Sure” she responded. I felt my tension ease and a smile spread across my face. “Great, see you later, umm, what’s your name?” We both couldn’t help but laugh about the fact that we hadn’t properly introduced ourselves. “I’m Chloe” she told me. “Alright, Chloe, I’ll see you at the bus stop!”

When I made my way back to the apartment, her pleasantly soft voice was still echoing in my ears. “Just three more days.” It was as if she had activated a countdown in my head with these words. A countdown which was now ticking down inexorably. I tried to assess the situation realistically. “There is no way I’m going to lay her.” Furiously, I tried to push the wondered that started creeping into my mind apart. I could feel that this encounter had changed the whole context of my vacation. No matter how it would play out, no matter my chances, now I had at least something to work towards. I had set myself a target and I was determined to do my best in order to achieve it.

As it was to be expected, the rest of the morning wasn’t really eventful. After we had eaten our breakfast, me and my family visited some nearby sights and strolled through the market that had been set up in the city center that day. Shortly after noon we chose a small restaurant for our lunch break. From there on, I could really feel the nervousness building up in me. I was struggling to finish my meal and decided to head back to the apartment, telling my family I was feeling a little unwell which technically wasn’t even a lie. Without further enquiries, my dad handed me the key and I left.

Back in the apartment, I tried to calm myself down which turned out to be nigh-on impossible. Chloe was all I could think of and she was driving me crazy. Nervously, I tried to prepare myself for our encounter by acting it out in my mind. What could we possibly talk about? What would she think of me? And how did we end up naked in my bed all of a sudden? I jumped up from the couch and had to take a deep breath as I looked around to reassure myself that I was still alone. I realized that my imagination had pointed out a weakness in my preparation that needed to be addressed. If just thinking about Chloe already made me lose my mind, how would I handle it if she actually made a move on me? I certainly wasn’t keen on emptying my balls with the first sensual touch or kiss she would give me but I could totally see this happening if I didn’t take appropriate precautions. So I went for the bathroom, took my phone with me and locked the door although none of this would have been necessary. I was on my own anyways. No one could enter the apartment without me opening the front door. And neither would I need my phone to search for any nudes or porn as thinking about Chloe was probably more than enough to get me off.

Since I was so stressed out, I just wanted to get it done quickly without unnecessarily exhausting myself. I recalled the fantasy of being with her in my bed. Imagining her hot naked body next to me got me hard in no time. In my mind, she would encourage me to touch her sensitive spots while telling me how good that made her feel. I didn’t have to go any further than that. It only took a couple quick strokes for me to blow a big load into a paper tissue which I quickly disposed of. A feeling of deep relief spread through my whole body and all of a sudden, I felt much more confident and prepared about meeting Chloe than before. With my nerves settling down and my head somewhat cleared, I decided to spend the remaining time in my bed in order to get some rest.

A knock on the door scared me out of my doze. Quickly, I reached for my phone to check the time. It was twenty past two. I breathed a sigh of relief before opening the door to my family. They appeared to have brought some souvenirs from the market. Luckily, they hadn’t taken more time to get back, otherwise Chloe might have waited for me in vain. “Are you feeling better now?” my mum asked me. “Yeah, I think I’m alright” I responded. “We were planning to go to a shopping center in the major city nearby” my sister explained. “Do you want to come with us?” “Ugh, you know I’m not into shopping at all. But don’t worry about me. I could use a little more rest and then I might as well explore the area here a bit more on my own” I lied hoping the three of them would set off as quickly as feasible. To my great delight, that was exactly what they did. “Take care of yourself and the key” my mum said with a serious expression. “And don’t get lost anywhere, otherwise we can’t get back into the apartment” my dad added with a laugh. “Of course, I’m not going to do anything stupid” I replied as I watched them leave.

Without wasting any more time, I got dressed, grabbed the key of the apartment as well as my phone and my wallet and headed for the bus stop. The parking lot next to the apartment was empty, so my family was traveling by car. On my way to finally meet up with Chloe my nerves got back at me. For some reason, I kept looking around as if someone was following me and was about to ask me where I was going. When I walked around the last corner before my destination, I saw Chloe already waiting for me. She was waving at me which made me quicken my pace. Upon arriving at the bus stop, Chloe greeted me with a warm hug. As we started chatting, my concerns quickly vanished into thin air since we got along really well. “You’re from the UK, am I right about that?” I asked her when we were already on the bus. Chloe gave me a slightly reproachful look. “Is my accent that telling?” she laughed. “Hmm, I’m not sure. Maybe I just have a good feel for it” I replied a little apologetically. “Okay, I’ll let you get away with that excuse” she said smilingly.

“So, what’s the best way to approach this for someone who hasn’t done anything like that before?” Chloe asked me when we were walking towards the karting track. “Take it easy but also don’t be scared” I replied. “The first thing you want to do is to memorize which way the track is going so that you always know what turn is coming up next. That’s the most important thing and shouldn’t be a big problem. Once you are familiar with the track, you should figure out where and how much you have to brake and what the best lines through the corners are. That might sound a bit more complicated but don’t worry, I can help you with that” I concluded my basic introduction.

We needed to attend a short safety briefing before we were finally allowed to hit the track. Right from the begin, I enjoyed the flowing and varied layout of the circuit and it didn’t take me long to come to grips with it. After a few laps that felt reasonably quick I decided to wait up for Chloe and stick behind her to see how she got along. For a beginner, she was actually doing pretty well. Time flew by and it felt like we were just getting started when the track staff were already ordering us back to the pit lane. The marshals helped us out of our karts and handed out bottles of water which was a welcome refreshment given the scorching sun and the thick racing suits that we were in.

“Wow, that was so much fun!” Even through her helmet, the joy in Chloe’s face was unmistakable. I was thrilled by her positive reaction. “Can we go again please?” she asked. “Of course, we can” I replied. “You were doing great but I also spotted some sections where you could improve your driving. So, if you’re really keen on going out on track again you might want to listen to what I’ve got to tell you.” “Sure, go ahead” she accepted smilingly. I signaled to the marshals that we would like to do another session before turning to Chloe. “So, think about the last two turns that basically merge into each other. Hit the brakes a little bit more there, that way you can keep a tighter line through the first part which opens up the last corner for you. This allows you to carry much more speed onto the start-finish straight.”

To my great astonishment, Chloe had absolutely no trouble implementing my instructions on track. I gave her a thumbs up when I passed her and set off in pursuit of the fastest lap I could possibly achieve. The track was really fun to drive and my focus on maximizing every corner helped me to finally clear my mind of the insecurities and doubts I had about being with Chloe. And just like the first one, the second session ended far too quickly as well. After getting out of my kart, I had a look at the timing screens which showed that I had missed the lap record by about half a second. Instinctively, I recalled my best lap to find out where I might have left some time on the table but Chloe’s voice brought me back to reality.

“You’re a genius!” she cheered. “It worked out exactly as you told me in the final turn.” Then, she also directed her eyes towards the timing monitor. “Wait, you had the number 14 kart, right?” she asked me. “That’s correct” I confirmed smilingly. “Wow, so you were actually in a league of your own” she said appreciatively before asking me “How can you be so good at this?” “Well, I’ve got quite some experience. However, not so much in real racing, but rather in virtual racing.” “Oh, I’ve seen something like this. My cousin has one of those fancy cockpits with a steering wheel and all that stuff at his home.” “Yes, I have something like that too.” She seemed genuinely impressed. “I could have gotten my driver’s license within three days with you as my instructor” she joked as we headed back to the bus stop.

“Excuse me for a moment, I have to call my friend” Chloe said when we were on the bus again. Curiously, I tried to follow the conversation. “Hey Florence, would you mind having some tea? And, yeah, take your time.” Chloe ended the call with a mischievous laugh and noticed my questioning look. “I think Italy isn’t really known for its tea or am I missing something here?” I asked carefully. “You’re right” Chloe said with a big smile on her face. “That’s why having some tea is a code for when one of us wants to have the pension room for herself.” Suddenly, all the alarm bells started ringing in my head. “Did she really just say that?” “Surely, this can only mean one thing.” Those were just two of the countless thoughts that shot through my head while I was trying to keep my cool and hold on to the conversation. “What were you laughing about at the end of the call?” I asked her trying to sound casual. “Florence said she was surprised that I made it this far into our vacation without making use of our code.” “Uhm, assuming it’s because of me, wouldn’t it have made more sense to ask me if I would come with you before chasing your friend away?” “Technically, yes. But now you can’t really say no, can you? And either way, I simply wouldn’t have accepted a no from you” Chloe replied grinningly.

I couldn’t believe how this day was looking to continue. As we got off at the same bus stop where we had hugged for the first time just a few hours earlier, Chloe grabbed my hand and was almost dragging me through the streets. Neither of us could wait to finally get to her room. With shaky hands, she turned the key and we rushed inside. Our lips met before the door had fell shut. Tightly entwined we enjoyed our passionate kisses but it didn’t take us long to realize that we were all sweaty and smelled of dust, gas and tires from the karting track. “Surely, we’ll need a shower before anything else” Chloe sighed. “Who’s going first?” I asked with a flirty smile hoping she wouldn’t figure out it as a serious question which she didn’t. “No one is going first, obviously!” Chloe replied firmly as she grabbed my hand once more to drag me into the bathroom.

We were quick to help each other out of our clothes and jumped in the shower. The water felt pleasantly cool on my body which was glowing from the heat of anticipation. We paused for a moment, holding hands and looking deep into each other’s eyes as we enjoyed the water gently pattering down on us. Her wet and messy hair only enhanced the naughty, lustful look that Chloe was giving me and her spectacular body proportions had me gasping for breath. We leaned in for a long, passionate kiss and as our hands began to explore our bodies, we knew that it was time to let our desires take command of the situation.

With great enthusiasm I realized that Chloe’s big, firm tits were looking even better when covered in shower gel and I could feel her nipples harden as I went on to tease them with my hands and lips. Chloe wasn’t at a loss to return the favor. She squeezed a large portion of shower gel into her palm, dispersed it all over my hard, throbbing cock and started stroking me eagerly. The sensational feeling of her hands gliding over my wet and soapy shaft made me moan but I was a little concerned whether I could handle the crazy pace she was going at. “Oh, that feels so good! But please go a little easier on me! I would like to enjoy this for as long as possible” I pressed out. Chloe immediately slowed down which made her strokes feel even more sensual. “Mmhh, I like your approach to this and I’m all in for it” she said with a voice that made me twitch between her fingers.

“So, are you going to fuck me really slowly?” Chloe asked. “Not yet” I replied as I pulled out of her hand, got on my knees and started licking her pussy. Chloe responded with a sharp scream that sent shivers through my body. “Oh, wow! I wasn’t expecting to get that kind of treatment” she moaned at me. Despite the neutralizing effect of the water, I noticed her incredible taste as I continued to eat her out. Chloe’s heavy breathing, her arching body and her hands running through my hair told me that I was doing the right things with my fingers and my tongue to give her what she desired. Soon enough, her legs were shaking wildly and she forcefully pressed my face against the wet and pulsating mess that I had turned her pussy into. With loud and deep moans, she orgasmed all over my face.

I stood up to kiss Chloe who was leaning against the glass pane of the shower, her body still trembling. She reached out to grab my cock again and froze. I couldn’t believe how hard I was when Chloe looked at me in disbelief. “Wow, how could you still take the time to please me when you’re that hard?” she asked me. “You must be desperate for a good release.” “Well, this is as much about you as it as about me” I replied as relaxed as I could. “I think you deserve something special for that. Something I’ve only let a few men do to me before. I’d be happy to have you cum inside my pussy. How does that sound for you?” she asked in that sensual tone which I had quickly become familiar with. “That sounds amazing” I moaned. Chloe threw me an encouraging smile. “Well, what are you waiting for?”

I knew for a fact that I was already close when I excitedly entered her tight pussy. This was my moment. This was what I had been working towards over the course of this crazy vacation. A vacation that I initially didn’t even want to go on. This was what I would have missed out on. After already having made her orgasm, Chloe wasn’t expecting anything more from me besides filling her up. She was fine with my load inside her so I didn’t even have to worry about pulling out at the right moment. All this made me feel unbelievably light. And somehow, I managed to withstand the urge to cum right on the spot. I was certainly pushing my limits in order to enjoy that amazing feeling of my cock deep inside her and ready to explode for a just a little longer. Her question whether I would like to fuck her slowly came back to my mind. “No way” I wondered to myself. I’m about to cum no matter what. So I might as well just give it all I’ve got.”

I made sure to have her body tightly pressed against the pane of the shower before I started fucking her. And I was fucking her hard. Her loud moaning was unmistakable but somehow it didn’t really reach my consciousness. I was only thinking about holding on for the next thrust to extend this as much as I possibly could and it worked out surprisingly well. With my focus so much on myself, it was only at the moment when my orgasm was imminent that I realized something unexpected was happening. As I finally came and blasted my load into Chloe’s pussy, her body was shaking again. Her incredulous look solved the puzzle for me. “Did I just, …” I was unable to sort out my words but Chloe still managed to answer my unfinished question. “Yes, you did just make me orgasm for a second time” she said as she supported herself against my shoulder. “I need some rest now” she sighed and I could have said the exact same thing.

We dried off and snuggled up in her bed. Chloe seemed to be thinking about something while I simply enjoyed holding her in my arms. A few minutes later, she broke the silence. “I think I found out about your secret” she whispered. “What do you mean?” I asked a little confused. “I was wondering how you were able to make me feel so good today” she replied. “Don’t get me wrong, the way you fucked me was amazing but I couldn’t find anything overly special that would explain how you made it that good for me. So, I guess it must have been because you made me feel so special. And I think that’s pretty rare, especially for guys who can get any girl they want.” “Wait a minute” I interrupted her. “First of all, you are special. The way I am treating you is simply down to that fact. “And secondly, do you really think I can get any girl I want?” I asked her perplexed. “Of course, why wouldn’t you? It worked out just fine with me. I’d say that is quite some accomplishment” she replied.

Despite her bright smile, I could see a hint of wistfulness in Chloe’s face and I immediately knew what she was thinking of. “Tomorrow is essentially the last day we can spend together” I said and noticed that I sounded a little depressed myself. The countdown that Chloe had started in my head with our first conversation at the bakery in the morning had turned into an hourglass for me. An hourglass the top half of which didn’t contain much sand anymore. And the little sand that was left at the top was relentlessly trickling down towards the bottom. “You sound like you haven’t had enough of me yet.” Her voice appeared to be flirty and untroubled which didn’t really reflect the mood we were in. “But don’t worry, I definitely haven’t had enough of you either” she added. It didn’t need any more words since our looks were enough to assure each other that we were both determined to make the most of the little time we had left together.

The ringing of my phone put a harsh end to our carefree togetherness. “Oh, shit, I totally forgot about that!” I cursed before explaining the problem to Chloe. “My family went shopping and left me the key to the apartment. They must have returned by now and they can’t get inside without me.” “Well, then you better run and sort that out.” Chloe was laughing about the situation while I hurried to put my clothes on. But of course, I wouldn’t leave without kissing her goodbye. “We’ll meet again at the bakery! Tomorrow morning, same time as usual” I stammered. “I’ll be there” Chloe promised me as I rushed to get back to my apartment.

NSFW: yes

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