NUMBER 1: A week with Olivia! (day 1)

DAY 1

The next morning, I said a warm goodbye to Sydney and Chloë and, almost giddy with excitement, waited for Olivia to arrive.

Thankfully I didn't have to wait very long, as soon enough, the door, which I had been watching unwaveringly, finally swung open to reveal the drop-dead gorgeous dark caramel haired chocolate eyed singer, in a short sky blue dress. As many times as I had now experienced something similar, I couldn't believe this was real - Olivia Rodrigo was right there, standing in front of me.

Clearly I must've taken a little bit too long admiring her out-of-this-world beauty, because I was woken from my trance by her saying: "Hi, Luke...Luke? Are you okay?"

I shook my head lightly and said awkwardly: "Y-yeah, I'm okay. Hi, Olivia. I'm sorry, I was just kind of instantly blown away. You're absolutely beautiful. I hope that's okay for me to say right off the bat, I'm sorry," - I finished, realizing what I was saying and blushing.

She smiled sweetly and put her hand on my arm gently. "Don't worry, Luke, it's not a problem at all. You're really handsome too, if you don't mind me saying" - she said, her cheeks turning a little red this time. I nearly fainted right then and there at her calling me handsome. However, I tried my very best to contain myself, and said: "Do you want to go have breakfast? And then after that I can show you around, since you are going to be staying here for the next week," - said, laughing a little at the end. She giggled a little too and nodded before replying: "Yeah, let's do that!"

So we went off to do just that. We were hitting it off straight away - all the other girls had been really nice and fun, but Olivia blew everyone else out of the water - I was thinking that she may just be the nicest and most amazing person I'd ever met. At the very end of the tour of the mansion and the grounds, I went to show her the bedroom.

Once we got to the bedroom, as I was showing everything in the room, I suddenly felt the lovely singer's hand take mine and squeeze lightly. I turned to her, and she kissed me gently, almost...lovingly? No, I was just imagining things. She then said, seductively: "Since we're already here, should we...kick the day off properly?"

I couldn't get any words out, so I just nodded. Seeing this, she began a slow, swaying motion, slowly slipping her dress off, eventually revealing her beautiful body to me. I was spellbound, and almost automatically took my own clothes off and embraced her tightly, before we moved to the bed with her straddling me as we started making out. My arms moved over her back, eventually going lower and squeezing slightly, as she pushed herself closer to me, her chest rubbing up against mine, allowing me to feel her pert nipples get harder. Something else was also getting harder behind her, and she quickly realized this, and, without waiting too long, reached behind herself and slid my erection into her entrance, gasping as she did so. She slowly, blissfully lowered herself further and further, beginning to rock back and forth gently. Our lips didn't part the entire time, tongues intertwined, sinking into the passion of the moment.

Once Olivia reached the very base, she picked up the intensity of her riding, but kept the slow, measured pace, her hands on either side of my face as she continued to kiss me. Her walls gripped my length incredibly tightly, making me feel like I had died and gone to heaven as she went up and down slowly - it was absolutely blissful. I separated myself from her and buried my face in her chest, breathing in her sweet scent and rubbing up against her soft, silky skin; eventually I went to "work on" her breasts, resulting in her throwing her head back and moaning out loudly: "Oh yes, Luke, right there, keep going, yes, oh Luke, oh Luke, yes, YES!"

I loved the way her body moved, each motion so unbelievably graceful, so full of passion. I was trying my very best to replicate this, and judging by her ecstatic reactions to my every move, I was succeeding. All of a sudden, her walls constricted and she screamed out "Oh yes Luke NEVER STOP!!!!", as she bucked harder and harder on top of me, her lips now returned to mine as we united in our joint, ever brighter burning passion for one another as our bodies connected. Her second climax came much faster than the first because of how in harmony with one another we had become. When she finally came down, I gingerly rolled her off of me, onto her back, before plunging myself back into her, this time from above rather than below. The incomparably beautiful singer's dark caramel hair messily covered her face as she buried her head in the pillow, she wrapped her toned legs around me and grabbed my face to pull me closer to her and deeper into her folds, her feet crossing on my back and her hands on my cheeks when she made out with me. I had established a stable rhythm by this point, so close to her that we were almost one as I passionately moving in and out of her increasingly wet sex.

I wished that I could keep this up forever, but at the same time I didn't want to deny myself the pleasure, especially considering we still had almost the full week ahead of us. Funnily enough, Olivia seemed to have a similar idea, as she broke our kiss and whispered sexily into my ear: "I'm on the pill. Fill me up, Luke."

I didn't need any more encouragement than that, and I sunk my gaze into her beautiful chocolate eyes as I orgasmed powerfully, shaking a little as I exploded a big load of semen into her vagina. She moaned at the top of her lungs at the warm sensation, and once again pulled me in for a kiss as I slowly came down. Once we broke apart, I whispered in her ear: "Here's to a week of feeling this good." She nibbled on my ear affectionately and replied: "Here's to every day feeling as amazing as that just did."

We washed off then went to lunch. Lunch was delicious as ever, but I never could've anticipated what happened afterwards. I turned away for a second to get something, but when my head turned back, Olivia had vanished from her place across from me. I looked around, confused, then suddenly felt hands unzipping my pants. I looked under the table to...obviously see her there. She winked at me seductively, pulled out my penis and promptly went to work on it. I sat back in bliss, and Olivia used her hands and mouth masterfully to very quickly draw yet another orgasm out of me, this one ending up all over her face. "Mmm...dessert" - she purred sexily.

For the rest of the day, we just chilled together, listening to music, playing board games and video games like we were teenagers at a sleepover. She was so lovely, and I was loving each minute she spent by my side more and more. We made out for a little while before going to bed. As I fell asleep, I couldn't wait for the six other days ahead of me.