Chapter 2

The rest of the afternoon passed in a blur of nervous anticipation. I couldn’t stop thinking about what was to come. The party, the charity cards, the idea of losing my virginity to someone I didn’t know well ... It was all too much. I found myself wandering the beach, the waves lapping at my feet as I tried to make sense of the situation.

Ella found me there, her own swimsuit barely covering her ample assets. She had an air of confidence about her that was both infectious and intimidating. “Hey, Mike,” she called out, her voice like a siren’s song.

I turned to face her, my heart racing. “What’s up?”

Her eyes searched my face as if looking for something. “You seem troubled,” she said, her voice full of concern. “Is everything okay?”

I sighed, feeling the weight of the world on my shoulders. “I don’t know who to give my charity card to tonight,” I admitted, the words feeling like a confession.

Ella’s smile grew knowing. “Come on,” she said, coming closer. “But remember, it’s just for a sex party. On this island, you’ll have many more opportunities to explore with lots of girls.”

“It’s not just a party. It’s also my virginity.” I asked, my voice cracking.

“Haven’t you lost it during the orientation?” she asked.

I shook my head. “Were you a virgin when you had your orientation?” I asked.

Ella’s smile grew wider. “No,” she said.

“When was your first time?” I asked, my curiosity getting the better of me.

Ella’s eyes twinkled with mischief. “Well, my first time was actually during my very first night here,” she revealed, her voice low and sultry. “I just hit a legal age, and it was with a very experienced man, someone who watched me grow up and knew me very well.”

The thought of a man watching her grow, knowing her, and then taking her virginity was both repulsive and fascinating. “Your dad?” I asked, unable to keep the shock out of my voice.

Ella’s eyes sparkled with a hint of amusement. “No, not my dad,” she said, her voice teasing. “But close enough. It was your dad, Mike.”

The revelation was like a punch to the gut. I stared at her, unable to comprehend what she’d just said. “My dad? How?”

Ella’s smile grew as she sat down beside me on the warm sand. “You know, on my first night here, I was just as confused as you,” she began, her eyes twinkling with a memory. “But let me tell you what really happened.”

Her voice grew softer, and she leaned in closer. “I had too much to drink, just like you did last night. I was stumbling back to my villa, and I couldn’t find my way. I was just about to pass out when I heard something that woke me up. It was coming from your villa,” she said, her eyes dancing with a mix of mischief and nostalgia.

“I followed the noise, and do you know what I saw?” she continued, her voice dropping to a whisper. “Your dad was fucking my mom. They were so into each other, so raw and passionate. And when your dad’s cock slid out of my mom, it was ... huge.” She licked her lips, the memory clearly arousing her. “I had never seen anything like that before. I knew I wanted it. So, I just walked in and they didn’t even stop.”

“They let you join them?” I managed to ask, my voice barely above a whisper.

She nodded, “It was my first time, and it was incredible. I came twelve times that night, Mike. Twelve times on his cock.”

“How many times did he ... you know, fuck you?” I asked, my voice hoarse with shock and a strange mix of arousal.

Ella leaned closer, her voice a seductive whisper. “Five, Mike. He cum in my pussy five times that first night.” She paused, a wicked glint in her eye. “And when I woke up the next day, my pussy was sore but satisfied, and I could not walk straight to the orientation,” she said, her voice thick with remembered pleasure.

I was speechless, the image of my dad fucking my childhood friend playing on repeat in my head. The idea of losing my virginity to someone I had known for years was suddenly not so daunting. It was as if the island was trying to show me that this was normal, that I should just go with the flow.

“What about the others?” I asked, finally finding my voice. “Did you do it with anyone else?”

Ella leaned back, her hand absently playing with the strings of her bikini top. “Oh, Mike,” she said, her voice filled with a knowing smile. “By the time I left the island that summer, I had been with more than ten guys. And let me tell you, our dads were one of the best.”

“Our dads?” I echoed, my mind racing with the implications. “So, there’s ... family sex?”

“It’s a sexual freedom island, Mike.” Ella’s laugh was like a melody of pure sin. “Your dad has been fucking my mom, my dad has been fucking yours. They’ve been sharing for years. So, when we join in, it’s like they’re just ... continuing what they’ve been doing?”

My mind reeled with the implications of what she was saying.

I stuttered, “What do you mean?”

Ella’s smile grew wider, and she leaned back on her elbows, her breasts pushing against her bikini top. “Well, it’s only fair, isn’t it?” she said with a wink. “After all, your dad took my virginity, so they thought it would be a nice gesture for my dad to do the same for your sister.”

“What about Alex?” I managed to ask, my voice barely audible.

“Ah, Alex,” she said, her voice dripping with a hint of nostalgia. “Last year, your sister Penny took his virginity. It was quite the night because he managed to fuck all pussies in the families. He’s quite the little stud, isn’t he?”

My mind reeled with the images she painted, the thought of my sister and my childhood friends losing their virginities in our families sharing, doing the deed making my stomach twist in a confusing mix of emotions.

Ella said, her eyes never leaving mine. “But losing virginity to whom actually doesn’t matter much because, in the end, we could fuck one another as much as we want in our families sharing.”

Her words hung in the air, and the implications of her statement began to sink in. I was still trying to process the revelation about my dad and hers when she leaned in closer, her breasts brushing against my arm. “So, Mike,” she whispered, “have you decided who you’re going to give your charity card to?”

I swallowed hard, my eyes darting from her breasts to her eyes. “I ... I still don’t know who should be my first,” I admitted, feeling a strange mix of excitement and dread.

Ella leaned back, a knowing smile playing on her lips. “You don’t have to use the charity card for your virginity, Mike,” she said, her eyes sparkling with mischief. “You can always lose your virginity before the party starts.”

“Thanks, but I think I’ll go for the party plan,” I said, hoping she’d understand. I didn’t want to follow in the same footsteps as Ella and our siblings.

Ella’s smile was understanding. “Why don’t you go out and make some friends?” she suggested, her eyes glinting with a hint of mischief. “You might find someone who’s perfect for your first time.”

The words hung in the air, and for a moment, I thought of Kiera. “Actually, I already have a friend,” I said, the image of her sweet, eager face flashing in my mind. “Kiera from the orientation, she’s ... she’s still a virgin too.”

Ella’s smile faltered for a fraction of a second before it returned, this time with a hint of mischief. “A virgin with a virgin,” she mused, tilting her head to the side. “That’s ... not the best idea, Mike.”

Her words stung, but I couldn’t ignore the excitement that coursed through me at the thought of being with Kiera. “Why not?” I pressed, feeling a sudden urge to defend my decision.

“Well,” she began, her voice taking on a patronizing tone, “you’re both inexperienced. Your first time should be with someone who knows what they’re doing. Someone who can show you the ropes, so to speak.”

Her words lingered in my mind but now I couldn’t stop thinking about Kiera. The way her pussy had felt around the vibrator. And how she’d looked at me when I came on her face. She’d been just as nervous and cute. Maybe she was the one.

“Ella, I think I’ve already made up my mind,” I said, my voice firm. “I want it to be with Kiera.”

Ella’s eyebrow arched, a look of surprise flashing across her face before she schooled her features. “But Mike,” she began, her voice laced with a hint of concern, “you’re both so inexperienced.”

“I know,” I said, cutting her off. “But we both made each other cum, during the orientation. And it was...” I paused, trying to find the right words. “It was beautiful.”

Ella studied me for a moment, her eyes searching mine. Then she nodded. “Okay, if that’s what you want,” she said, her voice softer. “But you better find her and ask her what she wants before the party. You don’t want to assume.”

Her advice was wise. I had to find and talk to Kiera. I had to know if she felt the same way about me. If she was willing to share this moment with me.

The sun had begun to dip below the horizon, casting a warm glow over the island as I searched for her. The beach was bustling with activity as the families and guests prepared for the night’s festivities. I wandered through the crowded pathways, my eyes scanning the faces for a glimpse of her. The anticipation was driving me wild.

As the shadows grew longer, and my search grew more desperate, I finally spotted her. She was sitting alone on the beach, her legs folded beneath her, watching the waves. She looked so small and vulnerable, and yet so incredibly sexy. Her youthful curves were outlined by the setting sun, and the light played with the strands of her hair like a lover’s caress.

I approached her tentatively, my heart pounding in my chest. “Hey,” I called out, hoping she’d look up and smile at me.

But she didn’t. Instead, she looked up with a frown, her eyes clouded with worry. “Mike, we need to talk,” she said, her voice serious.

My stomach dropped. Did she give out her charity card? Did she have someone else in mind?

“What’s up?” I asked, trying to keep my voice casual.

“Look,” she began, her voice shaking slightly. “I know we’re both new to this, and I enjoyed what we did earlier, but I’ve been thinking...” She took a deep breath. “I don’t think we should go to the swinging party together tonight.”

“Why not?” I asked, feeling a mix of relief and disappointment.

“It’s just ... I think we should utilize our charity card to pick an experienced partner for the party, so we can fully explore our sexual needs,” she said, her voice trailing off.

“But...,” I protested, feeling a desperate need to convince her. “We’re the only virgins on this island and I think it would be memorable to lose it together.”

Kiera’s gaze searched mine, a hint of regret in her eyes. “I’m sorry, Mike,” she whispered. “That’s not true anymore. I ... I found someone today. He’s really good, and we had sex all afternoon.”

The words hit me like a punch in the gut. I felt my heart shatter into a million pieces. “Who?” I managed to ask, though I wasn’t sure I wanted to know.

“It doesn’t matter,” she said quickly, placing a gentle hand on my arm. “What matters is that I’m not a virgin anymore, and I’m going to the party with him.”

The waves crashed against the shore as I struggled to process her words. The image of her virgin pussy, that I had just seen this morning, was now tainted by the thought of another man’s cock pumping away at it all afternoon.

I nodded numbly, trying to keep the pain from showing on my face. “It’s okay,” I mumbled, not knowing what else to say. “Now, I think it’s a stupid idea. Just ... forget it.”

With that, I turned and walked away, my heart feeling heavier with each step. The sand clung to my feet like a weight, pulling me down. I didn’t know where I was going, I just knew I needed to get away.

As I wandered through the crowded beach, trying to find a quiet spot to lick my wounds. The path grew narrower as I ventured further from the beach, the trees closing in around me like a lover’s embrace. The sounds of the party preparations grew distant, replaced by the gentle whispers of the wind through the leaves. I found myself in a small clearing. It was peaceful here, unlike the tumultuous emotions raging inside me.