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I woke up from a knock on my door. "Timo, are you coming? We're heading to dinner," I heard Nina say. I looked at my phone and it was 18:55. I quickly got dressed and opened the door. Nina gave me a kiss on the cheek and I went back to my room to get my things. Nina looked at me and said, "Thank you for today. I really had fun. I can't wait to tell you about my conversation with Luuk". We met up with Sofia and Luca downstairs and walked into the restaurant. Some time later, Julia and Mattheo also joined us. They told us that they had been having fun. They did a little hiking and Mattheo had been exploring the nearby city for some sightseeing.
"Hey, so I know you guys had a fun day yesterday. Do you mind if I ask you something about it?" Mattheo asked us. We all looked at each other, not sure what he was going to ask.
"So, I heard the four of you had, like, an orgy with your boss," he said. I could tell that he was really curious about it, and it didn't surprise me that he knew. "It wasn't really an orgy, as only Sofia and I had sex," Luca replied. "Yeah, we only watched," Nina said. "You guys are crazy," Mattheo said, laughing. We told him about what happened and he seemed really intrigued. On the other hand, Julia seemed a bit uncomfortable.
"Sounds fun, maybe we should try it sometime," Mattheo said to Julia, who looked at him with a surprised face. "I'm not sure if I'm ready for that yet," she responded. "I was only joking," he said with a smile. He grabbed her hand and squeezed it.
"Timo, you remember Mila and Ivan right? The hot athletes?" Sofia said. "Of course, they are great. What about them?" I responded. "Luca and I had a foursome with them today, it was really fun," she said. "We did a full swap, so I fucked Ivan and Luca fucked Mila. It was so hot". Luca nodded. Mattheo stared at them with huge eyes. "You did what? You fucked his wife while you let him fuck your girlfriend?" Mattheo said to Luca, who just nodded again. "Yeah, it was so hot, Mila is so hot. It was amazing," Sofia continued.
I felt proud of Luca as I knew how hot Mila was. I also had a tiny bit of jealousy as I really wanted to know how it was to have sex with her. Julia had a surprised look on her face. "Wow guys, that's crazy. Are you okay with this Sofia?" she asked. We remembered that Julia and Mattheo didn't really understand what kind of relationship Sofia and Luca were both in.
"Yeah, we are. We love each other, and we don't see this as cheating but more of a fun experience. It's a very liberating and open relationship," Sofia said. I noticed that Mattheo seemed really intrigued, and that he was looking at Sofia a lot. Julia seemed to think a bit about what she heard, but then went back to eating her food.
"We also had some fun," Nina interrupted and looked over to me. "Wow wow wow, wait, you did what?" Sofia said to her. "No, not like that, but I watched Timo have sex with Daniela today and Carlos was also watching," she said. Sofia looked at me surprised. "Did you have sex?" she asked Nina. "No no, we didn't," she immediately replied, "But, I may have joined in a little bit," she said with a devious smile.
Sofia and Luca looked stunned at Nina as they were also surprised about this. Julia was ignoring the conversation, but Mattheo looked at me with a huge smile. "Man, that's wild. You guys are like, really really wild," he said to us. "What did you do, you dirty girl?" Sofia said to Nina.
"Soooo... Daniela asked me if I wanted to join, but I told her I couldn't do that. Then, she offered to go down on me," Nina said. "So, I called my boyfriend for permission, and he told me to go for it. And it was so hot". Sofia, Mattheo and Luca's jaws were on the floor.
"Daniela went down on you? Fuck, that's so hot," Sofia said. "Bro, Timo, you watched that?" Mattheo asked. "I did, it was so hot. I even fucked Daniela from behind while she was eating Nina out," I said, with a proud smile. "Jesus Christ, and you didn't even call me to watch," Luca said disappointed. "Sorry man, I'm just really lucky to have experienced it," I responded. "You never told me your boyfriend was okay with girls going down on you," Sofia said to Nina.
"Well, we talked about it some time ago, and he was not sure at first, but I think he really enjoyed it," Nina said. "So when can I go down on you?" Sofia asked her with a smile. "Sofia! Not in front of everyone," Nina said. I could tell that Luca was already imagining it in his head. Julia was still ignoring the conversation and Mattheo looked at me and smiled. "You are one hell of a lucky dude," he said to me, but I looked over at Julia and thought the same of him. We continued our conversation a bit longer.
Everyone was clearly turned on by our conversation as we all left the restaurant and went to our rooms. When we walked upstairs, I could see Julia getting handsy with Mattheo. Although she felt uncomfortable with the conversation at dinner, it seemed to have turned her on a bit. Sofia and Luca were almost in each other’s pants when they entered Sofia's room and didn't even close the door.
"Timo, can I talk to you for a second?" Nina asked me. We went over to her door and went in. We talked for a while on her bed again. "So, when you left, I was having fun with Luuk. He really liked that I played with Daniela, and he would allow me to do it more often". I was happy to hear that as I really enjoyed watching her get eating out by another woman. "He even told me he would allow my friends to eat me out," she said, "But I don't think I'm ready for that yet".
I was wondering if "with friends" also meant me, but I was too afraid to ask. "Shit, I’m still super turned on from dinner. I wish my boyfriend was here. Julia and Sofia are probably getting their brains fucked out right now," she said and looked at me with her big, beautiful eyes. "We can go over and watch Sofia and Luca. They probably left their door open for a reason." I said to her, and she agreed.
We walked over to Sofia's room, both very excited, but to our surprise, they were asleep in bed. We were disappointed, as we were both horny and wanted to watch, but we didn't want to wake them up. I thought about Julia and Mattheo for a brief second, but they definitely wouldn't let us watch. Nina even tried calling Olivia, but they were still in town.
"Do you want to watch a porn together or something?" Nina asked me. "What did she just ask me?" I thought to myself. In reality, it wasn't that different from watching our friends have sex live, so I said yes.
We sat down on the bed as she turned on her tv and connected her phone with it. We were both super turned on, so we dropped our pants and underwear. She was now only wearing her bra and I was completely naked. I felt a bit weird laying here naked with Nina on her bed, as normally there were more people when we did this.
We tried to browse for some porn, but we didn't really find anything, and honestly I didn't need it. Looking at Nina playing with herself would do the job for me, so eventually we forgot about the tv and we just started watching each other.
I couldn't keep my eyes off her beautiful body, and also, I was really turned on seeing her play with her pussy. Her long, slim fingers playing with her pink clit was mesmerizing. She too was watching me as I had my cock in my hands. As we were masturbating in front of each other, we looked into each other's eyes. At that moment, I would have loved to touch her and feel her soft skin against me, but I didn't want to cross any boundaries. I tried to speak to her, but I couldn't. I just continued to masturbate as she was still staring into my eyes. I tried to get her attention as she looked down and then back up, but she kept her eyes on my cock. She started moaning and it was so erotic. Her moans were echoed in my head. She's so beautiful when she's horny. I felt my legs start to shake as I was about to cum. I stopped moving my hand as I felt the orgasmic sensation in my balls. Nina continued to rub her clit as I shot my load on my chest, and some landed on her.
"Aw shit, I'm sorry. I should have asked for a towel or something," I said and felt a bit bad for her. She looked down at my mess and smiled. "It's okay. I'm glad I got you to cum," she said with a devious smile. She continued rubbing her clit with a bit of my cum on her legs. It looked really sexy. I couldn't help but stare at her fingers going up and down on her pussy. She was still looking at me as she was pleasuring herself. She started moaning really loudly. The eye contact we made was so sexy as she came all over her fingers. I felt like I was in heaven right then.
She kept her eyes on mine as she cleaned her hands off with some tissues and she wiped the cum off her legs. I asked her to hand me some over too, but she crawled over to me and cleaned me up herself. "That was amazing," I said to her after she was done cleaning my chest. She laid down next to me, "Yes it was".
"You sure that your boyfriend is really okay with this?" I asked her. She looked at me with a smile, "After what we talked about, I think this isn't even as close as he would allow me to do and wants me to do. He will love hearing about this". We just kept looking at each other for a while, as we were so comfortable in the moment. "Thanks again for today, it was soooo amazing," she said and gave me a kiss on the cheek. We talked for a while and I gave her a big hug.
"Goodnight Nina," I said. "Goodnight Timo," she responded. I went back to my room, took a shower and went to bed. The connection I've built up here with all these people was getting bigger and bigger. I was so fortunate to have such good friends around me and I really felt at home here. I fell asleep thinking about the day. I woke up early the next morning because I promised Carlos and Daniela that I would meet them before they left. I walked over to their villa and saw Isabela talking to them. They had all their luggage packed. "Timo, you came! I can't believe you woke up early just to say goodbye to us. We are really lucky to have you," Daniela said.
She gave me a big hug and a kiss. Carlos gave me a hug too. I helped them with their luggage and put it in the taxi. "We will miss you guys. Have an amazing trip," I said to them as they got in. They said their goodbyes to Isabela and told her that they would see each other again soon. Isabela smiled at me and we both waved them goodbye as the taxi drove off.
I was very sad to see them leave. They were so nice to me, but I was also happy to have the opportunity to meet them. This was all thanks to Isabela, who introduced me to them in the first place. "Thank you," I said to Isabela, "You are a really amazing boss". Isabela was flattered by the compliment. "They really seemed to like you, and most of the guests do, so I'm glad I hired you". She looked me in the eyes and smiled.
We went back inside and I headed to the restaurant for breakfast. I saw Nina sitting with Olivia and Manuel, so I walked over and joined them. Manuel told us about the date they had yesterday. They went to an Italian restaurant in town and had a lovely dinner. They went to see the sunset at the beach and then back to the resort.
"Wow, sounds like you had an amazing day," I said to them. And although I still don't like Olivia, I couldn't deny that she and Manuel were such a beautiful couple. It was great to see them both so happy together. They really loved each other.
"Man, this year has been so good! Last year I had a fun time too, but everything seems a bit wilder this year. Maybe because Olivia and I finally decided to join in a bit too," Manuel said. "And you know, Timo and Luca have been a great addition to the team. Last year, there was a guy from Switzerland working here, but I couldn't stand his ass, so I was glad he didn't return this year".
After breakfast, I went outside as I was on bar duty again. In the morning, I worked behind the bar with Nathalie and Chris for a while. The mornings are a bit quieter as people don't order a lot of alcohol before 12. In the afternoon, I was serving the guests as usual. It was fairly busy around the pool, and I noticed a lot of new couples. I saw Mila and Ivan talking to another couple. The people who had been here for some time seemed to have made friends as I saw a lot more people in groups. I also saw a few people in the water and they seemed to be having a great time. It was such an amazing place and I really felt like I belonged here. When I was bringing guests their drinks and food, I noticed one group looking at me for a while. They laughed and it seemed they were talking about me. One of the women really stood out. She had an enormous chest and she was really hot. I guess she was about 40 and she reminded me of Sofia Vergara. She was the person who was looking at me the most and she even pointed at me for a second.
At some point, one of the men in the group waved me over. I was a bit concerned about what they would say, but I walked over to them anyway. "Can I help you guys?" I asked them. "Hey kid, we need to settle a bet," he said with a clearly American accent, "My wife here thinks she can make you cum in under 5 minutes". I was shocked by his sudden remark. He was interrupted by his wife, the big chested Latina woman, "Of course! I can just look at him, he is so young and inexperienced. He would probably burst even thinking about it". The rest of the group was laughing. "She never made any of us cum in under 5 minutes with her mouth," one of the other guys said. I was very confused and didn't know what to do.
"Look at his face! He is scared," his wife said. The group all laughed, and the man continued. "Come on kid, if you can last for more than 5 minutes, we'll give you a big tip". He was clearly a very arrogant man as he was looking at me as if I was a dumb kid. "So are you down?" they asked.
"Sorry, I can't during working hours," I said. They all started booing me and the wife put her hand on my leg. "I think you're just scared," she said. The man looked at me and said, "Kid, I bet you $50 you can't last longer than 5 minutes with her mouth. I think you'll burst after a couple minutes". "I'm really sorry but I have to serve the other guests around here too". As I found myself in a really awkward situation, Isabela came to me.
"Here, give me the tray. I can take over for 5 minutes," she said to me, having overheard the conversation. "Really?" I asked her. She nodded to me and took the tray. The group started to cheer up again as the woman grabbed my hand and said, "Come on, let's do this. I can't wait to see that face of yours when you cum," she said with a devilish smile. Although I found it uncomfortable, she really was hot, and I didn't want to reject a blowjob from her. "Okay," I said as the group cheered harder. "Okay, this is the deal: You can't touch her, and she can only use her mouth," the husband said to me. "Sounds fair," I said, as she started to undo my belt and reached down my pants.
I looked around the pool and everyone was watching us. Isabela was looking at me and gave me a wink and thumbs up as she kindly took over my work for me. The group cheered for us. The wife pulled down my pants and underwear. My cock was semi-hard as she put her amazing, big lips around it and started to suck. She looked me in the eyes and I felt her tongue on the tip of my cock. She didn't hold back and was sucking the soul out of my body. She kept making eye contact with me. I had honestly never had a blowjob this good before.
This older woman really knew what she was doing. I looked around the pool and saw many people staring at us. I noticed Nathalie at the bar looking at me and she started laughing. The people around the pool started to cheer me on, as the woman was sucking my cock faster and faster. "2 minutes," said the man, as he looked at his watch. The woman began sucking harder. Her spit was drooling over my cock. She continued to look into my eyes and it was super hot. I honestly forgot about all the people around me and just focused on her beautiful face and her warm, wet mouth.
Her tongue was dancing around my cock and I felt my balls tighten up. I knew I wasn't going to last much longer. "1 minute," the man said as I felt my balls tighten even more. She was now going into overdrive. I felt my legs shaking. The woman kept looking at me and she started to play with her tits. She continued sucking me like crazy. I saw Nathalie and Chris looking at us and I also noticed Isabela looking at me too. "30 seconds," the man said. I felt my knees go weak. "Oh fuck," I said to the woman as I couldn't hold it in any longer. My legs gave in as I shot my load deep inside her mouth. I could feel her swallowing all my cum and it was so overwhelming. I couldn't even say anything as she swallowed and then let go of my dick.
"Wooooaaaahhh!" she let out. "I told you guys," she said. Half of the group looked disappointed as they lost the bet. The husband gave me a high five. "Good try kid, but I had more faith in you. Guess my wife is just too good". I saw the people exchanging some money with each other. They returned to their conversation as if nothing happened. The rest of the guests also just continued with what they were doing.
Sometimes I forget almost all people here are swingers, so this was really normal for them. I felt the woman's saliva on my dick as I put my underwear and pants back on. Isabela came to me and gave me back the tray. "Timo, I'm disappointed in you. I thought you were going to do it," she said teasingly, as I smiled and went back to work. As I walked back to the bar, Chris came to me and gave me a fist bump. "Nice work dude! Yeah, you lost the bet, but you just came inside that hot woman's mouth, so I think you won," he said and laughed.
I was in a trance after that experience. Nathalie looked at me and smiled, "I guess she was pretty good. I don't think I would be able to do that in under 5 minutes," she said. I was surprised by her comment as she normally never talks about thinking like this. I laughed with her and continued working. Every time I went over to people, the guests started teasing me. It was a bit annoying, but just like Chris said, how can I complain? I just had an amazing blowjob from a super hot wife and I came in her mouth. As it was getting later, it became quieter around the pool. Isabela told me that I was done for today.
"By the way Timo, tomorrow there is going to be an orgy again. This is going to be a lot smaller than last time, and only 8 couples have signed up yet. So, I won't need your help in the evening. You are free," she said to me with a smile.
I went to my room and changed into my normal clothes to go to the restaurant. The whole group was there. When I arrived, they all started to tease me. "Damn Timo, only 5 minutes?" Manuel said. "Pfff, you can't talk. You came in like 2 minutes yesterday," Olivia said as we all started laughing. Nina even teased me, "It's not that bad, but sometimes I forget how inexperienced you are," she said to me jokingly.
"I reckon I could have done it in under 2 minutes," Sofia said. "No way. You are amazing with your mouth but not that good," Luca responded. "Hey!", Sofia looked at Luca as she pouted her lips. "I mean, there is only one way to find out," Manuel said. I couldn't tell if he was serious or not, but he and Luca laughed.
We finished dinner and hung around the restaurant for a while. "You guys want to hang out in one of the hot tubs?" Luca asked us. Everyone agreed as they seemed really in the mood for some fun.
"Yeah, and maybe we can find out what we talked about," Sofia said with a devious smile.
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This part was edited by urgin_virgin, so special thanks to him. Let me know if you like his editing style.
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