Hailey's POV
"How about I share an embarrassing story?" Ian suggested, but that felt too simple. Whatever he proposed would be something he'd only be slightly bothered by. I need something better, something to push him further. He's on the edge right now, revealing more than I expected, yet not enough.
"Hmm," I hummed, pretending to consider his offer. "Nah, too easy." I finally shook my head at him, noticing the worry in his eyes, which only made me smile. I don't know why I enjoy teasing Ian so much. Maybe it's because he's so innocent. Well, somewhat innocent, anyway.
"Okay, then what?" he asked, his tone tinged with concern.
"It has to be challenging and make you uncomfortable; otherwise, it wouldn't really be a punishment, would it?" I asked, revealing my mischievous side.
"Does it really, though? Couldn't it just be something small?" he almost pleaded. I think he could tell that I was being a bit too playful for his liking, but that only made me savor this moment even more.
"I think I've got it," I smirked, thinking of something great.
"What is it?" he asked, almost panicked, as he saw the excitement on my face.
"Skinny dipping. There's a pool on the roof, and since it's late, no one should be up there." The look of horror on his face was priceless, confirming that I had chosen well.
"You can't be serious?"
"Oh, I'm dead serious. Let's go, Ian. You should have just told me what you were thinking about." I winked at him as I walked towards my door.
I watched, surprised to see him actually get up. He was truly going to do it, even though I had no means to force him if he had chosen otherwise. The fact that he was willing to follow spoke volumes about his character. I led the way to the roof, taking the short flight of stairs. Being on the top floor, my penthouse made the journey to the roof quite brief. I stepped through the doorway first and held it open, allowing Ian to step out before shutting the door. I then decided to block it with a chair, preventing anyone else from coming up.
"There- I can't have anyone else seeing," I winked. "Now, strip and get into that pool, sir."
I chuckled, noticing a faint blush tint on his cheeks. His gaze averted from mine as he began unbuttoning his shirt, revealing unexpectedly well-toned muscles. He neatly placed his shirt on one of the lounge chairs, kicked off his shoes, and removed his slacks, carefully folding them. It was intriguing to witness his meticulous treatment of his belongings. Next, he removed his watch and socks, leaving only his boxers. His beautiful blue eyes briefly met mine, perhaps to check if I was watching, which I most certainly was, being a woman and all.
Although my curiosity was piqued, I decided to grant him some privacy, turning away before he slid off his boxers. I only turned back when I heard the splash of water.
"Jesus, it's cold!" he complained, hugging his arms to his chest in an attempt to keep warm.
Deciding not to be too cruel, I swiftly unzipped my dress, effortlessly sliding out of the heavy fabric. I left on my black, strapless bra and lacy black underwear, then jumped into the pool after him.
"Ay, Cielos!" I exclaimed as the chill of the water hit me harder than expected. "I thought you were just exaggerating, but it's freezing!" Ian chuckled at my reaction, causing me to smile. I found his laughter infectious. I watched him for a moment, submerging the lower half of my face in the water as I paddled closer to him.
"It's your turn," I reminded him gently. "Remember, I'll answer anything you want to know, even if it's about Liv."
"Why do you push me so hard?" He asked, surprising me once again. Sometimes I think I can easily read him, but then he throws me off with unexpected questions.
"Because Liv asked me to," I replied, shrugging. That's why I initially started doing this, but it's evolved into something more. There's a side of him that keeps emerging, and I can't quite explain it, but it intrigues me. It's like he's a hidden gem waiting to be discovered. I saw it with Liv, and now I see it with him. Whatever challenges life has thrown at him have caused him to bury that side of himself deep down. Is it all because of Liv? Or is there something more?
"That's not true," he said, shaking his head.
"What? You don't think Liv asked me to?"
"I can imagine her asking you to look out for me or something like that, but skinny dipping in your rooftop pool or starting a fake relationship doesn't seem like things she would have in mind," he pointed out accurately. "Want to try answering that again, or do you want to join me fully naked in this cold pool?" He looked amused, watching me decide. While I wouldn't mind either option, I knew that if I wanted him to be honest, I should be honest too.
"It's difficult to put into words," I began, choosing to float on my back and gaze at the stars as I spoke. "In simple terms, I see a side of you that I want to bring out because it seems truly amazing."
"I'm not buying it," he said, shaking his head, causing me to frown.
He didn't believe in his own amazingness. I didn't want to argue, so I removed my wet bra and underwear, tossing them out of the pool. I heard the soggy sound as they hit the concrete. He tried not to stare, but his gaze wandered more than once. I couldn't deny that I enjoyed the attention more than I probably should have. It's Ian, Hailey. Calm your ass down.
"Perhaps we should leave the pool before we freeze to death," I said, shivering from the cold. I noticed him looking at me with concern before giving a nod of agreement.
He hopped out of the pool before me, and I couldn't help but notice the size of his manhood, even in the cold. I didn't want to imagine how big it would be when it wasn't. I quickly slipped back into my dress and grabbed my soaking wet undergarments, squeezing out some of the water before balling them up in my hands. We left the pool area and quietly made our way back to the penthouse. Once in my room, I grabbed towels for both of us. Without hesitation, I shamelessly changed my clothes in front of him. After all, he had already seen it all on the roof. There was no point in hiding now.
"So, what would you like to do now? Or are you ready for bed?" I asked, trying to keep things simple.
"I'm not ready to sleep, but getting under the covers sounds nice. We should warm up," he suggested, already kicking off his shoes.
"Alright, take off your shirt and pants, dry off, and get into bed. We can cuddle for warmth- unless that's too much for you?" I teased, hoping to get him to agree.
"That's fine," he nodded, unbuttoning his shirt.
Oh God, I can't let myself be consumed by desire for this guy. I climbed into bed and watched him until he got in beside me. I wasn't sure how he wanted to cuddle, but he grabbed me and pulled me close to his chest, answering that question for me. I rested my head on his chest, listening to the steady beat of his heart. It was calming, like my own personal white noise. My eyes closed involuntarily.
Ian began gently rubbing my back, further relaxing me. He was so comfortable, which was a new experience for me. Previous attempts at cuddling had always been so awkward. Somehow, Ian made it feel right and safe. How did he do that?
"You know, Ian, I really was telling you the truth earlier. There's this part of you that keeps showing up that is really amazing and fun. You should let him out more often," I said in my relaxed, half-asleep state. He remained silent, continuing to rub my back, and before I knew it, I had fallen asleep earlier than intended.