I took a quick shower, fixed my hair, and put on a polo and shorts. Shortly after, I heard a knock on the door: "Hey Timo, can I come in?" It was Nina.
I opened the door. "Come in," I said. Nina looked strikingly hot. She wore a black dress that hugged her figure with a low-cut back. She greeted me with a big smile, walked into my room, and sat on my bed.
"Omg, it was hot watching Olivia and Manuel fuck at the beach! I couldn’t keep my eyes off of them. Gahhhhhhhhh, I feel giddy. Did you know I almost came from just watching? Then seeing you jerk off… wow! Ohhhhh, and you played with Olivia's tits! For a second, I thought you were going to join them!"
Nina was clearly still excited about our beach adventure.
"I don’t think Olivia would have allowed me to go that far. I think she let me touch her because she was so riled up and horny," I said.
"Yeah, that’s true, but it seems things are getting better between you two. Also, don’t you agree she is fucking hot?" Nina asked.
Yes, of course; I’ve never denied that, but I still think she doesn’t like me. Also, is your boyfriend still okay with all this?" I asked back.
"Yes! Even better, actually. Every time I do something of this sort, we FaceTime after, and he really gets into it. We even spoke about adding new rules, but I’m not ready for that yet," Nina replied.
That was when Nina received a text from Isabela. "She’s ready; let’s go to her villa," Nina said excitedly.
We made our way, and we were the first to arrive. Isabela opened the door, and Nina and I were stunned by how good she looked. Isabela was wearing a tight dark dress with a low-cut back. It showed off and complimented her beautiful body. Additionally, it was nice to see her in a dress instead of her normal work clothes.
We greeted her with a hug, and she immediately requested that we sit down; she was still preparing dinner. Nina and I sat on her couch and watched Isabela move around in the kitchen. We continued to admire and stare at her back while she was cooking. There was something about her; she had this whole sexy aura around her. Even when she walks around the resort, you can see the guests looking at her and admiring her beauty. She was toppled with an amazing body, a friendly personality, an open mind, and a kind heart. I noticed Nina was checking her out as well. Nina looked at me and mouthed, "Wow."
The doorbell rang; we assumed it was Sofia and Luca, but it was Nathalie and the man from the pool—her husband. He was tall (6'4) and incredibly muscular. He was wearing a tight black polo, and he gave off the vibe of being someone you don't want to mess with. Nina was impressed by his height, dark complexion, and handsome features.
Nathalie was wearing a sexy red dress. It was hot to see her amazing body wrapped in such silky fabric. Her dress also revealed an ample amount of cleavage. It was a spectacle.
Nathalie’s husband greeted Isabela with a smile and a kiss on the cheek. Nathalie gave Isabela a hug and a kiss. They walked over to us, and Nathalie introduced her husband, saying, "Hey guys, you both look lovely! This is my husband, Ramiro." Nathalie hugged us both, and Ramiro gave me a firm handshake. "Nice to meet you," he added.
"Likewise," I replied.
Isabela came over with a tray of drinks. "Sofia and Luca are running a bit late," she said. Nina and I gave each other a look and giggled. They were always late, and we both knew why. We didn’t comment on the matter, but instead, we grabbed our drinks and sat on the couch.
Ramiro and Nathalie joined us, and we all sparked a conversation. Ramiro's tough-guy demeanour was not his personality. He was soft-spoken and super nice. We also learned he was a personal trainer and a semi-professional boxer.
After some time, Luca and Sofia arrived. Just in time for dinner. Everyone exchanged pleasantries, and we all sat around the dinner table.
Isabela served her amazing homemade Albondigas, paired with Patatas Bravas. This dish quickly became one of my favourites here in Ibiza. We chatted some more, ate delicious food, and drank our drinks. Upon finishing, we thanked Isabela and helped her clean and wash the dishes.
We retreated to the living room, where Isabela grabbed two bottles of wine and poured everyone a glass. She didn't want us to drink too much since we all had work the next day. But it kept our conversations going, which eventually led to the topic of our sexual experiences, or rather, lack of them.
"I don't know how you can go here without sex for so long, especially with your husband away." Nina questioned Isabela.
Isabela let out a small laugh. "It’s hard, isn't it? Especially for you, Nina, since you’re still young."
"But it sounds like you’ve been enjoying yourself here. I’ve heard the stories." Isabela winked at Nina.
Nina blushed. "Yeah, it’s nice watching, and frankly, I really enjoy it. However, you have to admit, it's hard NOT to join in with all the crazy hot people around. It's impressive that you managed to do so the whole time you’ve been working here."
The rest of us were all intrigued by their conversation and listened attentively.
Isabela sipped some wine. "Actually, I have joined a handful of times." Everyone was shocked. We all stared at her in silence, eyes wide open.
"My husband consents to the idea of me joining others if I want, but I’ve never gone the whole way. I don't feel too comfortable with that. But believe me, I've been tempted many times and invited to join more than I can remember." Isabela takes another sip.
"Now we want to know the details!" Sofia said daringly. The rest of us nodded.
Isabela smirked and fell under peer pressure. "Okay, okay. I've been eaten out by a few women and some men. I received a massage from Ava and Martin, who both ate me out after; that was amazing. I gave some men quick handjobs."
She sipped some more wine. "The last handjob I gave, some of you were there, so I don't have to tell you about that." She winked at Sofia and me.
Isabela added, Oh, and I’ve given two blowjobs; one was short, 5 seconds long, to a friend of my husband because I lost a bet. The other time … well, that was kind of a weird story. A few years ago, there was a guy working here. He was a virgin and had no prior experience, but he was excited to work here. I learned he wanted to feel what it was like to receive a blowjob."
She paused to sip her wine, and we all sat on the edge of our seats, waiting for her to finish the story.
"After two months of working here, the poor lad failed to hook up with someone. He had no luck. I felt bad for him. On his last day, my husband said I should give the boy a blowjob. So, the young fellow and I talked about it; he agreed, and I gave him one in my office. He lasted 30 seconds, but yeah, that’s it."
We all stared at Isabela in awe. Ramiro probably questioned what kind of crazy staff Nathalie was working with. Nathalie looked stunned but excited after hearing the story.
"That was so nice of you!" Sofia said it enthusiastically.
Luca whispered to me, Damn, that dude is so lucky! Imagine getting your first blowjob from Isabela?!"
Isabella responded, "But that is all I've ever done in the eight years I've managed here. I’ve never had sex with anyone other than my husband. And you know, it’s actually great because when we rejoin, especially after not seeing each other for a while, the sex is amazing. And besides, as you ladies know, we have many toys available to fill the void."
She sipped her wine again. "But you know … I'd like to get more involved. My husband really wants me to, so you never know." Isabela giggled and winked at everyone.
"You can always join us!" Sofia exclaimed.
"I will keep that in mind." Isabela said while raising her glass of wine at Sofia and Luca.
Luca blushed instantly, and I could tell he was turned on by the thought of Isabela joining them.
The conversation continued and lingered mostly around the topic of sex. I noticed Ramiro touching Nathalie's inner thigh as they became increasingly turned on. "Sorry guys, but we have to go. I have a few early appointments tomorrow." Ramiro said.
I was slightly disappointed because I wanted to hang out with them for a while longer. However, judging by how touchy and affectionate they were towards each other, I’m sure they had other plans once back in their room.
We said goodbye to them, and Isabella walked them to the door.
Isabella turned to us and said, "I would love to join you guys for a night of drinking, or am I too old for you all?
"No, we’d love for you to join!" I replied.
"It’s a great idea, and we should plan a day for it." Nina added.
Luca and Sofia weren’t paying attention, as they were practically all over each other. "Sorry guys, I'm super horny, so I think we are going back to our room." Sofia said it bluntly.
Luca looked at Nina and me and said, "You guys can come over and watch again if you want."
Isabela interrupted, "After all those stories I've heard, I'm actually curious. If you two are comfortable, you can do it here if you want."
Luca turned red, and Sofia was shocked. They were both extremely excited by the idea of Isabela watching them.
Luca looked over at us and said, "Are you guys okay with that?" He asked.
Nina bit her lip, contemplated for a second, and replied, "Yes, it would be nice to watch here."
I agreed with her.
Sofia and Luca wasted no time, and they began making out and undressing each other. Sofia was wearing a sexy black lace thong and matching bra. Her body was absolutely amazing as always, showcasing her perfect breasts and a toned tummy. Luca was wearing black boxers that did not stay on for long.
"Oh wow!" Isabela was surprised by their eagerness and speed.
Luca pushed Sofia onto her back and rubbed her nipples with his fingers.
Isabela sat between Nina and me, and I could smell Isabela’s perfume. She smelled expensive with a tropical twist, and combined with the sight of Luca and Sofia going at it, I was completely turned on.
"Oh, you two look so beautiful," Isabela said to them.
She turned to us and asked, "So do you guys like to pleasure yourselves while watching?"
We nodded, and Isabela smiled.
The three of us turned our gaze back on Sofia's breasts while Luca squeezed and pressed them together.
"Omg, Sofia, they are so big!" Isabela exclaimed.
"Thanks, \[Sofia moaned\] I like yours too."
"Don't be shy, guys; you can play too." Isabela said to Nina and me.
We were a bit reluctant with our boss sitting between us, but slowly, our hands travelled south and we began rubbing ourselves. Isabela sat there with her arms crossed, observing the action slowly unfold.
Sofia flipped over and pushed Luca onto the couch. She began sucking his cock, and Luca pulled her close to eat out her pussy. They were in a 69 position and really going at each other. Small, muffled moans barely escaped their mouths.
Sofia got up and went on all fours, protruding her big ass in the air.
"Jesus girl, your ass is amazing," Isabela said. Isabela saw Sofia’s ass when I was fucking her by the pool, but just like me, Isabela was impressed to see it again.
Luca was lining up to enter Sofia but was having some trouble with his erection. With all the excitement, the wine, and probably the nerves from Isabela watching, He stroked himself vigorously in hopes of getting hard, but it wasn’t working.
Isabela sprung from her seat and walked up to Luca. "Can I help you with that?" she asked.
Luca looked at her, surprised and speechless, and just nodded. She spat on her hand, firmly grabbed his penis, and started jerking him off. Luca was stunned.
Nina and I looked at each other in disbelief. We were both impressed by Isabela’s soft approach and daring confidence. Isabela was hot, but this elevated her status.
Luca was enjoying the feeling of Isabela's soft hand around his cock. He began to moan, and Isabela smirked. She then grabbed Luca's hand and placed it on her amazing ass. Luca’s eyes shot wide open, and I’m sure his mind was on the verge of exploding.
He caressed her ass through the thin fabric of her dress. I was slightly jealous of Luca because he got to play with Isabela’s ass. But she did jerk me off by the pool, so I couldn't complain too much.
Nina was rubbing herself faster, and I could see the excitement on her face. She pulled her dress off, revealing her sexy matching black lingerie. Isabela looked back at her and said, "Wow Nina, you are so beautiful."
Isabela continued rubbing Luca. He was super-erect. She stopped stroking and guided his cock towards Sofia's wet pussy. In one swift and effortless motion, he entered deep into Sofia.
Sofia let out a loud moan.
Isabella said, "Have fun," before returning to her seat between Nina and me.
Luca thanked Isabela and began thrusting in and out of Sofia. Sofia’s moans echoed in the room alongside the slapping sounds of their bodies.
Isabela watched Nina pleasure herself. Isabela quickly darted to her bedroom and returned with a vibrator. She handed it to Nina. Nina thanked her and placed the vibrator on her clit.
Isabela admired all of us. "I get why you do this. Watching this is so hot!"
By this point, I was jerking myself off, full cock on display. Isabela looked at me, smiled, and asked, "Are you enjoying yourself, Timo?"
"Very much so! It was hot watching you help out, Luca," I replied.
Isabela blushed.
Nina turned up the vibrator setting and began moaning louder. Isabela put a hand on Nina’s inner thigh. "Is that okay?" she asked. Nina just nodded and continued playing with the toy.
Sofia started shaking and gushing as she reached her orgasm. She fell flat on her stomach, and Luca continued to thrust into her.
Isabela placed her other hand on my thigh and gently began rubbing it. The touch of her soft hand felt unbelievable and made me even more erect. She wasn’t done yet, though. Isabela leaned slightly forward, arching her back and protruding her ass. She grabbed my left hand and placed it on her ass. She encouraged me to caress it like Luca did before.
It was soft but firm and honestly indescribable. Words cannot do it justice. I grabbed, I squeezed, and I traced the curvature. It was all too much, and I nearly erupted. However, I slowed my pace and enjoyed the moment.
Nina continued moaning louder and louder as she hit her peak and began cumming.
"Omg that's so hot," Isabela said while squeezing Nina’s inner thigh.
"Thank \[Nina moaned\] you; it feels so \[another moan\] good," she said in a weak voice.
Luca slowed down, looked at me, and asked, "Do you want to join Timo?" Isabela smiled at me, but I was too busy caressing her ass, so I declined, saying, "No you continue; it’s nice to watch."
Isabela was surprised I rejected the offer, but she continued massaging my thigh. Her touch sent a wave of tingling sensations through my body. It felt forbidden. The more she rubbed, the closer I came to finishing.
"I'm close." I muttered. Isabela quickly grabbed tissues from the table and placed them on top of my cock. She then took over and began jerking me off. Nina watched with excitement.
Her hands were magical. She stroked me up and down and caressed my balls in her palm, all the while I played with her ass. I groaned, I moaned, and I fought the best I could to hold off from cumming. Isabela was too good with her touch, and I came so hard!
She caught it all with the tissues and wiped my cock clean. "That was hot!" Isabela said before getting up to throw away the tissues. I could barely process what just happened.
I look across from me and see Luca fucking Sofia like a rabbit. He pulled out and came on Sofia's back and ass. It all felt too good to be true.
"Thank you, guys! I felt like I was your age again. \[Isabela sighed\] That was incredibly hot!''
She was smiling and was so happy. She genuinely had fun and enjoyed watching us.
We all slowly came down from our orgasms. Luca and I were in disbelief; Nina was filled with excitement but exhausted; and Sofia was practically smitten cheek to cheek.
Sofia ran to the bathroom to clean up, and we all got dressed. It was getting late, so we tidied up and prepared to leave. We gathered and shared a big group hug. Isabela thanked us again for the amazing night.
Sofia and Luca left first. As I was about to leave, Isabela said, "Daniela and Carlos are leaving in two days; they would love to have you over tomorrow before they leave."
I was excited to hear that and would love to see Daniela again. I thanked Isabela. We embraced for another hug before saying good night.
Nina and I went back to our rooms, and before I entered, Nina gave me a big, tight hug. "That was incredible! I really love doing this with you guys; it makes me forget about the sex I'm not having," she said while chuckling.
I smiled and hugged her back.
"You are a lucky guy, Timo. Having a second experience with Isabela, ow, ow," she howled with a teasing smile.
I blushed.
"And sorry if this sounds a bit weird, but can I ask you something?" She said it nervously.
"Go ahead," I responded.
"Mmmm, well, can I join you tomorrow when you go to visit Carlos and Daniela?
I was surprised by the question but thought it was a great idea. I smiled and said, "Yes, of course, but only if they're okay with it."
Nina gave me a big smile, followed by a bigger hug, and thanked me. "Yay! This will be great. I can't wait for tomorrow," she said excitedly.
I stepped into my room and went directly to bed. I reflected on the surreal day I had. The whole thing was unbelievable. If someone told me a month ago that I would be jerking myself off to my friends having sex while my boss watched sitting next to me, I’d call you delusional. I’m in utter disbelief but also having the time of my life.